You can now book time with me for in-depth, ad-hoc working sessions. Session topics have so far included:

• We think we need to hire a COO, but we’re not sure. Help!

• I’m a new Chief of Staff and I’m drowning in AI-enabled chaos.

• Can you use stablecoins for [insert cool use case here]?

• I want to advise startups. How do I get started?

• I’m a new consultant (and former exec) — is my pricing right?

Book time today at amandasr.com and let’s get you moving. Any topic is fair game.

I announced a set of workshops a couple weeks ago, and as of this morning: I am officially blowing them up.

Here’s what’s up: my Name Your Expertise workshop focuses on helping you take your decades of hard-won experience, and from there, articulate unique and marketable expertise that you can offer to startups today. It’s for mid-career / exec folks who have spent most of their time heads-down, and now want to orient toward building portfolios of impact (vs just servicing one job).

So I launched it, and then I learned two things:

1. People want this.

2. Human coordination became an unnecessary bottleneck.

My hope was that I could channel everyone toward 1-2 preselected dates that work nicely with my calendar. What I learned is that I cannot :)

So, I’m pivoting.

Introducing On-Demand Coaching with Amanda

Screenshot of amandasr.com

At amandasr.com, you can now book time with me for any topic you’d like to work through together: Scaling / COO stuff, dynamics with your founder / CEO / management team, stablecoins, management / leadership and influence, on-ramping into advisory or consulting, pricing / proposals / client management…. you name it.

All sessions will have an AI-assisted intake that will help us jump right into working together and skip past the 30 minutes of context-setting. You’ll also get a clean and actionable recap from me that you can turn around and use right away.

For help in naming your expertise and positioning yourself for advisory and consulting with startups

Book a 50-minute session.

I’ll hand you my course exercises when you book, and we can either use our session together to work through the exercises, or we can spend the time on feedback and brainstorming. Either way, you’ll leave well on your way.

I’ve really enjoyed each and every on-demand coaching session to-date, and I’d love to work on something with you!

Do you have a meaty problem you’d like another pair of eyes on? or a goal that’s been sitting on your plate, mostly untouched? Set up some time and let’s jam.

<3

Amanda

Have questions? Respond to this email. I read each and every response.

Last week I announced that I’m coming out of a teaching hiatus to test a workshop format that I’m really excited about. You might sign up, and because you’ve been a longtime subscriber, I’ve included a nice promo code for you in this email.

Read on for more.

An AI sandwich

What do you get when you combine a coffee chat, AI jamming, and then relevant human feedback?

You get what I’m starting to believe is the future of skill-based learning: the AI Sandwich. Yum.

I’ve figured out that this is basically how I like to learn:

Hands-on, but not totally self-guided. Sufficiently grounded in recent market insight, not years-old assumptions. Fast path to momentum, but not solely riding on AI-generated judgment.

As you can tell, I’m excited.

So, say hello to my new workshop: Name Your Expertise. It’s for execs who want to figure out and properly name the expertise they’ve built over their long and interesting careers.

Why? Because doing so ties you less to your employer(s) and orients you more toward the opportunities you actually want.

It’s a yummy AI sandwich that will help you shape your non-linear career experience into concrete expertise that startups actually want. Not 3 years ago, but now. Even in this weird market.

If the format works well, I’ll convert it into tasty sandwiches focused on what I actually do all day: strategy and operations. We shall see.

More on the course

Format: live, ~3-hour half-day. Here’s how we build the sandwich:

• The bread, top slice. I frame what I’m seeing in the market — the pattern, the traps, what “good” looks like — and what I’ve learned doing this exercise countless times before pushes for more advisory, consulting, investing, teaching.

• The meat and veggies. You work with AI on your own material, mining your career history to uncover areas of expertise that you clearly and uniquely posses. (This is fast and fun, but also potentially wrong, which is why the next layer matters.)

• The bread, bottom slice. I sanity-check the output against what’s actually getting hired this quarter — live, in the room with you.

You leave with a concrete and credible blurb that you can send to 3–5 people this week, and a simple validation plan to further test the market against your new thesis. All things you can actually use.

A couple of things to know:

It’s pathway-neutral on purpose. Whether you’re weighing consulting, advising, angel investing, a board seat, or a new operating role, the articulation work is the same. It’s the prerequisite.

This is heavily oriented toward getting you relevant insight from the market, and is not a feel-good exercise. I’m a practicing COO and therefore on the buyer side of the exact founder conversations you want to be in this quarter. Your personal network is going to balance my view with theirs, giving you a better picture of what lands vs does not.

Dates, price, and your promo code

Two cohorts are open:

• Saturday, May 2, 2026 — if you’re ready to move now

• Saturday, June 6, 2026 — if you want a few weeks of runway

Both are $599. As an Amanda Thinks subscriber, use AMANDA100 at checkout for $100 off either cohort.

→ Register for Name Your Expertise

A few questions I’ve fielded since launching

Do I need to know what I want to do next? No. Most students will arrive weighing two or three options (consulting, a board seat, a new operating role, angel investing). This articulation work may serve as a starting point for any path.

Two cohorts are open, May and June. Will you run one in July or August? Probably not. If this sounds relevant for future exploration, I recommend taking it now.

What do I need coming in? Updated resume or LinkedIn profile (must-have). A list of recent accomplishments from prior roles (nice-to-have, even in journal form). Prior writing or speaking that demonstrates your expertise (nice-to-have).

Is AI fluency required? No. I’ll support you in using AI for the first time, if needed. Please do have the Claude Desktop app downloaded and a minimum-tier subscription locked in before we start.

I have a decent understanding of my positioning but would like 1:1 coaching. Do you offer that? Yes. Head to my instructor page and you can book time with me directly.

If this is landing, and you know someone sitting on 15 years of exec experience and a wish for the future, I’d very much appreciate you forwarding this. ❤️

More to come as I keep playing. Also, more writing and less promotion in future letters, I promise.

XO,

Amanda

After some positive feedback and questions about my personal journey coming out of last week’s newsletter, I thought it would be a good time to bring back a podcast that I did earlier this year with now friend, Limor Bergman Gross.

This became one of those conversations where we both forgot we were recording, and I hope it adds some more color to my personal story moving from operator to full-time consultant.

Limor is building “From a Woman to Leader”, a space for women navigating all of the mess of leadership transitions and career pivots. Check out the episode below.

We covered everything from my transition out of an intense operating role while pregnant, to why building a website before landing your first client is just procrastination in disguise. If you’re thinking about going independent, or you’re already a few years in and wondering if you’re doing it “right,” this episode is for you.

What you’ll get from this episode

My weird career journey (4:01)
I talk about my path from the music industry to tech to consulting, and how my core skill of being “backstage support for creative geniuses” translated across all of it. Spoiler: you don’t need a perfect background to make this work.

My “why” for consulting (10:30)
Being pregnant with baby number three while working insane hours was my forcing function. I did _not_ want to slow down, but I needed the model to change. Your “why” will be different.

Step away from your title and no-one will get hurt (23:59)
How to deconstruct your corporate roles to find what you’re actually good at versus staying boxed in by your title. This is where most people get tripped up when trying to position themselves as consultants.

The truth about your first contracts (26:41)
I reached out to my warmest network first, and those early projects were poorly defined at best. But here’s why that was actually okay and what I wish I’d done differently about contract length.

Why your website can wait (28:28)
This might be controversial, but building a logo and perfecting your LinkedIn before you have a single client conversation is procrastination that feels like productivity. I explain what you should do instead.

The joy of self-direction (29:43)
Freedom isn’t just about setting your own schedule. It’s about molding your work, pursuing what interests you, and collaborating with people you actually want to work with. Once you taste this, it’s hard to go back.

Should you actually do this? (31:09)
My litmus test: can you name 3 to 5 people who trust you and would sponsor you into opportunities? If yes, and you feel compelled, give it a shot. If not, maybe stay where you are and keep building those relationships.

I’ve written about several of these topics in more depth. Check out my piece on positioning if you’re struggling to articulate what you actually do.

Join me in January

And if you’re past the “thinking about it” stage and ready to build your consulting portfolio, I’m opening up a small group coaching circle in January. It will be limited in size and curated to allow for strong cross-group learning and networking. We’ll work through positioning, proposals, pricing, and all the tactical stuff that keeps you stuck. Join the waitlist below:

Join the waitlist

This podcast conversation reminded me why I love this work. After three and a half years, I’m still figuring things out, but I’m also more convinced than ever that becoming “unhireable” was the right move.

<3
Amanda

P.S. If you listen to the episode, let me know what landed for you. I’m always curious about what resonates.

New home, same me.

Welcome to my newsletter. It’s called Amanda Thinks, and it’s an all-encompassing place for me to write things.

You might be here because you found me through my course 👋, my recent article in the First Round Review, or because you’re a long-time subscriber of Thinking in Quarters 😘.

In all of these cases, you’re in the right place.

What is Amanda Thinks?

It’s a prompt — and a reason for me to mine my personal experience and think critically on a regular basis. In doing so, I hope to develop my POV on things like strategy, operations, consulting, advising, management and leadership. All thoughts are my own, typed with my own fingers.

I’m centralizing all of my writing in Substack, which allows for subscribing / unsubscribing to topic areas that you care about. Eventually, I’ll turn on subscriber chats so that we can really get to know one another.

How can you support, you ask? Share this newsletter with 2-3 people who you think it would resonate with. That would be very sweet of you.

Without further ado, some quick thoughts….

On staying unhireable

When I first started flirting with the idea of consulting, it was only supposed to be for 18 months. I was pregnant with our third baby (the other two were 5 and 2), and I couldn’t imagine keeping the pace that I was at.

I also remembered the feeling of going out and returning from maternity leave. My typical playbook was:

• work until I’m ready to burst,

• eat Chick Fil A daily while anxiously waiting to give birth,

• bask in the afterglow briefly before losing myself to seven seasons of Scandal,

• spend weeks anticipating work before finally returning at the peak of my baby’s predictable sleep regression.

I knew the drill.

I also had friends encouraging me – “just pick up a few projects” “you don’t need to have the whole thing figured out before you do it” “good thing you moved out of the Bay – time to be thankful for that low mortgage!”

All of this advice was good enough, and off I went.

And then: I fell in love with it.

The “it”?

1. Freedom: the feeling of being able to say “yes” for the first time in my career. No longer was I constrained by my employment relationship and therefore unable to advise that company, sit on that board, work in that friend’s startup, etc. I was a kid in a candy store. And then, when that wore off and the market went upside down, I was even more grateful to have….

2. Diversification: I had multiple clients in the middle of restructuring and layoffs, and others raising large rounds. I was working with CEOs who were being shown the door, and being called by others who were being hired. My fate wasn’t tied to a single company, and that really mattered.

Now, for me, this wasn’t just a work/life balance play. I did, and still very much do, value control over my schedule, and I did not want to work 80 hours per week.

But I wasn’t trying to go into cruise control or early retirement. I wanted to hustle, create opportunities for myself and others, stay on a steep learning curve, and drive real impact.

So I spent 18 months trialing self-employment. And then another 18 months loving self-employment. And now, I’m in my third 18 month inning and I’m thinking “how can I stay unhireable for another 3 years?”

By this, I mean: how can I keep enough meaningful opportunities on my plate that I wouldn’t dare walk away for a job? In doing so, I continue to optimize for my “it” above.

Will I always value Freedom and Diversification like I do today? Probably not. But for now, I sure as hell do.

Wanna hear me chat about this with another full-time consultant?

Click here to listen to my recent Lightning Lesson with Emily Hollender.

For those celebrating, Shanah Tova, and have an easy fast.

Amanda

Last week, I hosted a Lightning Lesson called "Position Your Expertise for Consulting in the AI Era" and it was so much fun. Missed it? Check out the recording and highlights below.

I also made an exciting announcement on the call:

I'm launching a group coaching circle! 🎉

This is a small, curated group that will dive deep into positioning and offer development, but also get tactical on proposals and pricing. I'll be your resource as you actually navigate the market. This is open to course alumni AND folks who haven't taken the course yet.

Click the button below to learn more and secure your spot.

Explore coaching

Lastly, many of you continued submitting your intro blurbs, and I've really enjoyed providing feedback! In fact, the last batch caught the attention of a VC and had broader amplification through the Fractional Jobs newsletter! In my next newsletter, I’ll highlight several more blurbs and share my feedback. Want feedback on your blurb? Click here.

Highlights from my lightning lesson

We had a great conversation and some of the questions were so good that I wanted to capture a few highlights for everyone. You can watch the recording using the button below.

Watch the lesson

What's your 10,000 foot view of the consulting market right now?

The market's completely different from when I started as an independent consultant in 2022. Back then, the idea that I could drop in as a part time COO and then leave was pretty novel. At cocktail parties, I'd say "I'm a part time COO" and people would go "What the hell are you talking about?"

Now? Fractional work is everywhere. That's not my hook anymore. Instead, I lean much more on my industry experience and functional expertise. And then there's AI, of course. Companies are dealing with business model transformations and workplace changes that weren't even on the radar in 2022. It's essentially a completely different market, and you need to contextualize yourself within that reality.

Do we even need human consultants anymore when AI can generate strategy decks and financial models?

Yes! The market for consultants is growing because companies are trying to understand how to leverage AI technology, not just adopt it. If you look at the P&Ls of major consulting firms, they're ballooning out of control. There's increased demand due to tech disruption AND due to downsizing of headcount.

Just like your favorite AI assistant, you could always drop questions into the minds of smart analysts and get answers. That's exactly how I started my business. But that was never what I handed the client. There was always contextualizing insight, applying judgment, framing recommendations. You're not outsourcing any of that to AI.

As a consultant, 95% of the value we provide is in aligning, influencing, and motivating people. AI does none of that. There's always going to be opportunity and need for wisdom and real insight versus just information.

How do we justify premium rates when companies are cutting spending?

There are a few must haves to make this work. First, you need real expertise in whatever you’re working on. It shouldn't feel like a stretch assignment. You should be able to jump in on day one and add real industry expertise and value through access, know-how, or functional value.

If it's specialized, incredibly relevant to the problem the company is solving, and you're flexible in your billing (not demanding 3,000 hours upfront at $4,000 an hour), you're probably going to be the “one of one” answer to this problem. You're coming without the baggage of a full time executive, you're there fast, you ramp quickly, you solve the problem.

If that's the case, you should be billing at the appropriate rate. Don't discount your rate, and don't go insane because OpEx is tight. If you're delivering in a credible and relevant way, there's no risk in billing appropriately.

I contributed to a piece in the First Round Review that talks about what real relevance looks like for startups of all stages. Click here to give it a read.

Where are most of your leads coming from?

85% of my business has come from people I've worked with before, or people who know those people. You need a list of people who are waiting to work with you, who would be happy to give you opportunities. Without that short list, all the strategy in the world won't translate.

Now that I'm in year four, I'm starting to see referrals from current and past clients. But qualified cold leads from my website? That's just not happening. It's really about cultivating relationships with folks you already know.

If someone's just starting out with positioning, what's one thing they can do today?

Go through your work experience and synthesize your expertise across industry and functional areas. If you've been in any career for more than 15 years, this is brutal but necessary. One mistake I see often is over generalizing.

You need that mix of industry experience, functional expertise, and what I call thematic expertise (relevance). The thematic part shifts as you pay attention to the market, but your functional expertise should be durable. You can't be shifting from product leader to finance leader every quarter, because then I'd wonder if you were either.

​

<3

Amanda

Honestly, it’s been the highlight of my week reading through them. Some of you clearly nailed it right out of the gate (impressive), others are wrestling with the classic “I do everything for everyone” trap (been there). There’s quite a range, and that’s exactly what makes this so interesting.

I’m still working through all the submissions, but I wanted to jump in here with some patterns I’m seeing and a few quick wins you can apply whether you submitted or not. Plus, I have some thoughts on why most of us struggle with this whole positioning thing in the first place.

Here are the blurbs

Here are 5 excellent blurbs I'd like to highlight (with names redacted for privacy):

#1

I help founders punch above their weight in fundraising and execution. As a former VC and startup operations leader I work with series A/B startups 12 months pre/post investment round — wrangling, launching, and executing on funding and growth plans to get the money and put it to work.

Amanda's Feedback

What really works: "Punch above their weight" is fun and specific, plus your VC background gives you strong credibility. The 12-month window is smart positioning. You clearly know your sweet spot.

​
​Some tips: Think about how a startup founder would actually describe their needs. Instead of "wrangling and executing", they're looking for someone who can help them nail their pitch, avoid fundraising mistakes, or deploy capital without burning through it. Tell the client what box to put you in. Don't assume they know what to do with you. Fundraising and execution are important but two distinct offerings. As a generalist, you may want to have different blurbs for different audiences.

#2

I help growing companies build AI into how they operate. Most companies see AI's potential but can't figure out how to actually make it work in their business. As Chief of Staff at [Company Name] who led AI integration during 20→500 scaling, I know how to connect people, process, and technology to build systems that get real results. Companies stop thinking about what AI could do and start using it to realize its potential.

Amanda's Feedback

What really works: You've identified a real pain point. Companies see AI's potential but struggle with implementation. Your experience during that growth phase is solid proof, and you're clearly onto something valuable.

​
​What could be improved: You have an interesting niche (AI-Fluent Chief of Staff), run with it. Focus on your concrete angle. Instead of "connect people, process, and technology," tell me you help companies automate their customer onboarding or build AI-powered sales forecasting.

#3

I'm an ex-founder turned fractional Head of Growth for pre Series A AI companies, building product-led growth engines that scale beyond founder-led sales. I've led growth at all stages from bootstrapped startups to VC-backed companies and Fortune 100s (ex Slack/Salesforce, Best Buy) and know where to apply outsized energy to drive systematic growth from <$2K MRR to $100Ms in ARR.

Amanda's Feedback

What really works: "Ex-founder turned fractional Head of Growth" immediately establishes credibility, and focusing on pre-Series A AI companies is nice and narrow. You're in a hot space with real expertise.

​
​What could be improved If the sentence jumbles in your mouth, you've lost the reader. I do this all the time. Don't worry. Break up those long sentences and resist the urge to prove everything at once. Your core positioning is already strong.

#4

I’m [Name]. After leading HR at high-growth companies like Headspace, Elemy, and F45, I launched [Company Name] to bring that same hands-on, scale-ready approach to startups. I work with founders who are growing fast and buried in people problems. Onboarding is a mess, comp is all over the place, and managers are winging it. I step in as a fractional Head of People to clean it up, build what’s missing, and help the company grow without falling apart.

Amanda's Feedback

What really works: This is the strongest blurb of the bunch. You paint a vivid, relatable picture of startup chaos, then position yourself as the solution. The problem description ("onboarding is a mess, comp is all over the place") makes founders nod their heads.

​
​What could be improved: Honestly, not much. Maybe tighten up that last sentence, but you nailed the positioning.

#5

[Name] is a fractional strategist and executive coach passionate about helping companies thrive at the intersection of profits and purpose. She works with first-hires to Series A+ startups to help them build strong systems, and cohesive teams. By working together, this talent stays longer and the company's heart stays intact.

Amanda's Feedback

What really works: You're addressing an important tension that many growing companies face, and the range from early hires to Series A shows you understand different growth stages. There's real wisdom here.

​
​What could be improved: Here are some questions to think about to make your blurb more concrete. Profits and purpose sounds like you're interested in mission-driven companies. Is that your focus? Do you focus on culture? If so, say that. Are you offering coaching or consulting or something else? From first hires to Series A, where do you specialize? Narrowing down and avoiding broad terms like "fractional strategist" would help people understand exactly what you do.

If any of these sound like someone you'd want to hire, let me know. I'd be happy to make the introduction!

Subscribe now

Join me: Lightning Lesson on August 6 – NEXT WEEK!

And speaking of positioning…

I’m hosting a free Maven Lightning Lesson on August 6th, 2025 (9:30 AM Pacific) called “Position Your Expertise for Consulting in the AI Era” where we’ll dig into:

• Mapping your expertise to find your actual consulting sweet spot (not the one you think sounds impressive)

• Crafting positioning that highlights what AI can’t do—your judgment, taste, and ability to read the room

• Getting clarity on whether this path actually fits your life (spoiler: it’s not for everyone)

Looking forward to seeing you there!

<3

Amanda

After brand new “nice to meet you” convos, there are a few things that help me keep other consultants top-of-mind:

1. A good conversation (I learned something & felt good vibes while we chatted), and

2. They followed up with a solid blurb

#1 is certainly more important than #2, but here’s what happens when I don’t have a solid blurb:

Let's assume you and I chat, I walk away smiling, and immediately get mauled by my children or my next meeting. While I hope we speak again, I’m on to the next thing.

And then, exactly 9 days later, my client mentions that he is interested in a CX expert with experience in health-tech (in this story, that’s you). Because I like connecting clients with other consultants, I tend to remember my conversations. I tell them, “I may know somebody like that.”

Then I search for your LinkedIn profile. I think, “Ah, got it. Let me share their profile, along with a few bullets on why they may be interesting to my client.” It goes on my long to-do list, and after my son stops screaming L-L-L-LAVA CH-CH-CH-CHICKEN in my ear, I’ll go ahead and craft a thoughtful intro to make the connection.

Ugh... this is a lot of time and effort for me, and all this friction costs you opportunities.

So what exactly makes a great blurb?

In writing a great blurb, you have a few goals:

• Establish relevant credibility: highlight your industry, sector, or stage-relevant functional experience.

• Be concise: make your most important points by sentence 2 or 3.

• Stay human: no weird buzzword combos or generic consultant phrases written by AI.

As consultants, we talk about “positioning” – essentially establishing that you have hard-to-acquire expertise in an area of extreme relevance for your prospective clients.

Go too broad and you’re a forgettable “generic consultant”. Go too narrow without relevance, and you’re a friendly face that gets filed away as another LinkedIn connection.

Want an example of a decent blurb? Here’s mine:

Amanda is a strategy & ops exec with a track record of standing up and scaling fintech businesses globally. While at PayPal, Amanda led incubation, operationalization and turnaround efforts for emerging units and corporate functions. After PayPal, Amanda joined Dapper Labs to lead business operations, strategy and corporate development. Amanda now runs Garden Labs, an advisory practice focused on refining strategy and operations for emerging tech & high-growth startups.

I have 14+ versions of this blurb. This one’s a bit jargon-heavy, but it works. I did manage to synthesize over a decade of work that creates extreme relevance for fintech COO advisory projects.

I called out specific companies (PayPal, Dapper Labs), concrete outcomes (scaled business units), clear focus (emerging tech & high-growth). I removed past fluff about “synergies” or “leveraging best practices.”

I adapt this blurb for different contexts: consulting projects, crypto advisory, board conversations—always positioning my expertise for credible relevance.

Subscribe now

Join me: Upcoming Free Lightning Lesson on August 6

Speaking of positioning…

I’m hosting a Maven Lightning Lesson on August 6th, 2025 (9:30 AM Pacific) called “Position Your Expertise for Consulting in the AI Era” where we’ll dig into:

• Mapping your expertise to find your actual consulting sweet spot (not the one you think sounds impressive)

• Crafting positioning that highlights what AI can’t do—your judgment, taste, and ability to read the room

• Getting clarity on whether this path actually fits your life (spoiler: it’s not for everyone)

Because here’s the thing: You’re craving freedom and impact. Many of us are. But in a world where AI can write strategy docs, your positioning better be sharper than “I help companies transform.”

Looking forward to hearing from you. I’m really excited to support you on your journey!

<3

Amanda

We ended up fleshing out a comprehensive guide that breaks down exactly how fractional talent can accelerate your path through product-market fit without the commitment (or cost) of full-time hires.

The full piece walks through exactly:

• when to bring in fractional help across different functions (sales, ops, product, you name it),

• how to structure these relationships so they actually work, and

• how to identify the red flags that'll save you from expensive hiring mistakes

Plus, we dive into some real examples of how this plays out in practice, which I think you'll find pretty useful whether you're considering going fractional yourself or thinking about hiring someone.

Read the full piece here.

I hope this guide provides a useful framework for founders and fractionals. Huge thanks to Julianna Marchant and the First Round team for their thoughtful questions and excellent work putting this together.

I was working with a CEO recently who astutely shared that her company values needed a subtle, yet thoughtful revamp. I gave some thought to how this is both natural, and incredibly important to stay on top of. Below are those thoughts. I hope you find some value in them!

Also, further below is an update on that course for Execs who want to advise / consult that I’ve been yapping on about. tl;dr — it’s open for enrollment!

Your Values Are Being Challenged All The Time

Have you ever worked with someone long enough that you don’t need to guess where they stand on an issue?

You’ve developed a shorthand that allows you to navigate situations efficiently. You share a sixth sense about things – and you can call one another out if something feels inconsistent or amiss.

I’d argue that, in many cases, this is because you share a set of values with this person, (whether explicitly stated, or not) – and these values serve as a foundation for your day-to-day assessments. 

Trust plays a massive role too – allowing both of you to engage openly, without clouded mystery or dancing around the bush.

Stating (and living) values as a young company is a way to scale this shared sense without bias and extra delay. When values are defined and clear, a team can quickly get on the same page and get to work.

How values drift

As organizations of people get larger and the context that you’re operating in gets more complex, things change in both big and small ways. Whether you realize it or not, your company values get tested.

And this likely happens more often than you think.

These tests can be small – like that “incredible candidate” that you have to swoop on who happens to be an asshole – or big, like that decision to hire a VP of Product. 

Both of these tests can either help you build conviction in your shared values, or rock them to their core. 

Over time, if you let your eye off of the ball, these tests will cause your values to unintentionally drift.

Dissecting forces that cause values to drift

When thinking about these tests, I started considering them as “forces” that are both generated within and outside your company.

Some internal forces:

• Team shifts

  • We’ve all seen this— leadership turns over and soon, the next level down does too. This undoubtedly changes how decisions are made: what is prioritized, who is hired, and how you connect across organizations all start to feel different.

• Strategy shifts

  • New product lines bring a new customer segment of focus to the center. New customers require different motions from the team (in terms of team responsiveness or product quality, for example), and internal practices begin to shift or conflict in response.

• Operational shifts

  • New processes or controls lead to new types of conversations. These conversations can reinforce existing values or require a new perspective to be meaningful.

  Because I love diagrams — I will now present you with one:

In the context of company-building and scaling, here are some examples of what this could look like:

• Poisonous leaders: you hire a new rockstar Chief Product Officer who you later learn is uncollaborative and breeds an “us vs. them” mindset between teams. Before you know it, your values of transparency and collaboration are gone – and information-hoarding is the new standard.

• Over-corrections: Leadership agrees there’s a cross-functional execution issue. The fix: a quarterly planning process to reinforce the importance of “intentionality” (a new value!) Initially, it’s beneficial — but a year later — “intentionality” has lost its original meaning, and the process no longer serves the purpose.

• Whale customers: you land a huge contract with a new enterprise customer. Your team over-indexes on servicing the whale, and a couple of quarters later, you realize it’s at the expense of the rest of your business (and maybe, your culture).

And those are the things that are in your control.

There are also external factors that deeply challenge the day-to-day of teams:

• Cultural shifts: a global pandemic, a natural disaster, or a war cause major disruption to your de facto work setup. Now, all collaboration and info-sharing mechanisms require immediate revamping—which can strain process and people, and in turn, your values. 

• Economic shifts: funding or labor markets shift, reducing growth, pipeline and / or runway. Morale follows. Before you know it, your team defaults need to change.

The Bottom Line

Your company values are your compass, and they exist to keep your teams calibrated with one another on which way is North. If properly utilized, they are there to reduce noise, speed up decision-making, and provide continuity as you scale. 

But scaling never happens in a clean silo. The journey of company-building is riddled with both self-inflicted (internal) and totally outside-of-control (external) forces that will test your values. Many will present you with an opportunity to reinforce and strengthen your values set, or they will provide an opening for unintentional drift.

As a leader, your role is to provide that continuity – and your values are worthy of your focus and intentionality. 

A best practice is to regularly check in to ensure congruence between your stated values, your everyday culture, and the needs and aspirations of your business. I have a framework for doing this that I’ll share in my next post.

<3

Amanda

Are you a leader interested in exploring a new chapter as a solo advisor or consultant? If so, I’ve got a course for you :)

This is essentially the course that I wish I had when starting Garden Labs. In it, I cover the fundamentals of defining a unique (and targeted) offering, building a pipeline of real opportunities, and setting up / managing a back-office. Everything will be infused with real first-hand examples, tools and insight.

Click here to learn more

My goal with this first cohort is to curate a group of seasoned leaders, and support them deeply in their transitions.

If you or someone you know is interested in making this shift — I'd love to chat!

I’m also leading a Free Lightning Lesson on Maven on Aug 14 to talk a bit about the transition, and will dig into how to evaluate the path for yourself. RSVP here.

Months ago, Gagan Biyani reached out to see if I’d be interested in becoming a featured instructor on Maven.

It was an immediate “hell yes” as it was a clear way to scale the COO advisory practice that I’d built over the last two years. It also centered on something that gives me energy — teaching — and felt like an opportunity to get smarter on the black magic that is “ops”.

So I jumped in and started developing the course that I wish I had earlier in my career.

And then something interesting happened…

I looked back on my calendar for the last many weeks and noticed a new theme: execs who were interested in transitioning into full-time advisory or consulting mode — and weren’t sure where or how to start.

These were all incredibly talented folks, with specialized skills and years of experience. All with loads of value to add to startups and large cos — at a fraction of the time, cost and risk of a full-time exec hire.

So I picked up the pen and started designing an offering that included: tactical resources, a private community of support, and access to coaching along the way — effectively, an on-ramp into the solopreneur world for the busiest people.

Today, I’m excited to share that both courses are coming along well, and I’m opening up the “transition to advisory” course for pre-enrollment.

To make sure this course is 10/10 valuable, I’d love your help in doing some customer discovery.

How you can help:

• If you’re an exec interested in transitioning into full-time consulting / advisory — please take 2 minutes to fill out this brief survey and help me get to the heart of what you need the most.

• Please share this course opportunity with anyone you believe may be interested. That would mean the world to me.

If you’re like me, and loving the flexibility, variety and impact of full-time advisory / consulting — I’d love to chat. I’ll be locking in great guest speakers for a session or two.

Excited to keep building with your support!… 🙏🏼

XO,

Amanda

PS: another course for emerging Ops leaders is also in development! Please stay tuned for more info on that front ❤️

But often, they feel like words on a page — established with great care, however easily forgotten.

At Garden Labs, we work with companies (some startups, some publicly traded cos) who are at inflection points. 

They are scaling after a major funding round, pivoting strategically, restructuring for more efficient growth, turning over leadership, transforming culturally.  These all have the potential to be company and org-defining moments, where teams emerge with renewed energy to continue the ever-winding journey that is ahead. 

Or, they have the potential to bring on immense churn, burnout and loss of momentum. 

One observation that’s jumped out at me over the last year is this:

Companies with a clear set of values navigate inflections with more clarity and conviction than those without. 

Here’s what I’m seeing…

Funding, labor and technical paradigm shifts have been the incredibly disruptive concoction of the last 18 months. Most agree that the next 24 months will be even more chaotic.

In many cases, companies are turning to advisors (👋) and investors to seek counsel.

While founder / CEO instincts define the map for how to navigate, I’m finding those with clear values also have a handy compass for navigating around the noise (bad advice), and grounding themselves in moments when the sky is raining down around them. 

In these tricky moments: 

• Are they being brave and principled? or fearful and reckless? 

• Are they executing with care and foresight, or are they creating more problems than opportunities?

• Are they taking input to guide them on their path, or allowing recency bias to determine their fate?

In all cases, these are risky turning points. But those leaders with strong compasses (i.e. values) seem to navigate these big decisions (and all of the small decisions that follow) in a manner that is more decisive. Less twitchy. They also achieve real alignment across their teams, even on intensely controversial topics — and they proceed with caution. 

So while you may not need a compass everyday – when you’re lost in the woods, I can bet you’re thrilled that you have one.

Generated with Llama 3

XO,

Amanda

When I was young – in fact, throughout my entire childhood – I followed my Dad to the office. 

In the Valley, we’d call him a serial entrepreneur. He started in construction, expanded vertically into building products, and now runs one of the largest window, door and building component manufacturing operations in the region. 

At 8, 17, 26, I’d tag along with my Dad and my Uncle (his co-founder) for lunch. These lunches were always the same – we’d go to Coco’s, and I’d sit there quietly while my Dad and Uncle ramble-discussed something ad nauseum.

• “Should we sell this building?”

• “How do we price that job?”

• “Is our factory manager working out?”

Some topics would get resolved between bites with a simple nod of the head, while others would stretch on for days.

From the outside, this looked both natural and grueling. But it’s been the method for most of their company decisions for the last 40 years.

While this may sound like “family business stuff” – it’s not. 

Every. Single. One. of the startups that I've worked with have some co-founder (or early team) dynamic that implicitly shapes their lasting culture.

These practices may be well-known and honored, or they may be hard-coded yet unspoken (like the pie in my story above). Either way, they are a part of the company’s DNA — its nature.

As an Ops Leader, sometimes you’re there on Day 1 and can directly shape the company DNA.

But many times, you are brought in later to help solve problems — and in that scenario, you may need to help nudge the culture forward.

But, before you can effectively do that, some simple advice:

Find the pie.

Hello, friends!

As you can see, I’ve taken a little writing hiatus. Life happened.

But also: hello perfectionism, my old friend….

In order to get back into the groove, I’m going to write shorter and sporadically, with hopes of getting some momentum again. The next few posts will be about values.

Overall, my topic area will continue to be company-building, especially from the POV of an Ops Leader — if that is relevant to you: please stay tuned!

By far: my favorite part about writing is hearing from you.

Do you have any hot topics that you’d like an outside view on? Just reply here and share your question / anecdote / mess. I’m here for it all.

With ❤️,

Amanda

To try and become good at this, I got my hands on any “executive communications” toolkit I could find.

Preparing for these meetings started to feel like I was Indiana Jones trying to crack the Dial of Destiny — I needed to solve this cryptic puzzle to report on my project in this magical way that got my team what they needed. It all felt so… hard.

But here’s the thing: execs aren’t mythical creatures that need to be spoken to a certain way, lest you disturb them and get chased out of the cave.

You’re dealing with someone who is relentlessly context-switching — and your ability to orient them to your topic efficiently is the unlock.

Georgia, on my team, offered a story to bring to life the opposite of what this looks like. :) 

I started out my career in finance, and quickly learned that my safest space was Excel. After making a pivot into early-stage tech (and GoogleSheets, ugh, IYKYK), I continued to crush at making spreadsheets my primary personality trait.

Tasked with a simple analysis to inform a tactical business decision, I meticulously prepared rows of confusing numbers and notes. (Amanda here: if you’re just joining us now, this is something I like to refer to as The Backslide.) Armed & loaded for my exec meeting, I hopped on and confidently shared my creation. After that typical 2 seconds of awkwardly waiting, my trove of heinous cells appeared — and before I could get past a “can you see my screen?” — I was quickly halted:

“Can you summarize the top takeaways, and drop them in Slack?”

But what about my journey through my reasoning? I certainly didn’t have the highlights to drop in Slack BEFORE that riveting adventure. Just like that, a week of work was skipped over “until I was ready.”

The lesson?

With most stakeholders (especially execs), the value of your work is in your translation — not in your demonstration.

Sure, your peers might want you to show your work. But in most cases, and especially with execs: bring them up-to-speed efficiently, deliver your key insight, make your ask, and listen. Here are some quick tips for doing that.

1. Cruise in at the right altitude. 

Anyone else live with someone who watches the Sci-Fi epic Foundation? Ever casually decide to join them, but on Season 2, Episode 4?

Yeah, good luck. You will frustrate yourself and everyone around you before retreating to your room to watch Love Is Blind: After The Altar.

Jumping into a complex topic with a flubbed tee-up evokes this same feeling (“wait, can we pause and rewind for second? What is happening here? Why is she turning green?”)

Instead of doing that – try this:

Envisage yourself a pilot.

I often think of altitudes. Depending on the other person’s familiarity with the topic, I typically start high, and then I slowly descend.

Some examples of what you’re covering at various altitudes:

Outer Space: “Why does this work matter?”

30,000 ft: “Things are going ok. Hitting some snags, but working through them.” 

10,000 ft: “Two work streams are struggling, and here’s what that could mean for the effort overall.” 

5,000 ft: “There are three things driving delays in those work streams. Here is what we’re doing [or would like to do] about them.” 

5 ft: “Here are the notes from our last meeting on this.”

Tarmac: “Here is what I need from you.” 

There are a few things that are worth calling out about where to start: 

• If an exec is familiar with the work, but you need to orient them quickly to where you are — here is your descent: 30k —> 10k —> 5k —> Tarmac

  • Don’t forget to land the plane. Hovering at 5k ft is a good update, but likely not the purpose of your 1:1.

• If an exec is brand new to the work, provide a couple of Outer Space remarks, just to gauge alignment – “this culture initiative matters because we have a retention problem” — if you don’t have obvious agreement here, you’ll likely get stuck down the road. Pay attention.

• Attempting to spend half of a 30-min meeting in Outer Space (exploring the “why” land) and then nose-diving to the tarmac will burn you alive. OK, that was unnecessarily terrifying, but it’s true. If you need to spend significant time aligning on the “why”, dedicate an entire meeting to that before cruising into next steps.

•  Preserve 5ft for the working team. Here is how I like to tee-up team-level discussions:

  • Outer Space (because regular reorientation on the “why” is helpful)

  • 10k ft (objective big picture on how we’re doing)

  • 5k ft (actionable paths forward)

  • 5 ft (who is doing what)

2.  Guide Their Descent (Don’t Free Fall)

My first manager at PayPal gifted me a helpful framework for teeing up conversations at the right altitude, and it’s something I still use to this day.

The SCIPAB Framework:

When done well: each bullet represents no more than 2 sentences.

• Situation: this is the current state; all facts (without controversy).

  • “The Summers are hot in California.”

    • You want complete agreement here before proceeding.

• Complication: something is hard or breaking.

  • “Our Air Conditioning is running all day, and that’s really expensive.”

• Implication: why does this matter? what is the consequence of not taking action?

  • “If we keep spending money on our energy bill, we won’t be able to afford tickets to the F.O.R.C.E. Tour.”

• Position: We need to do [THING]. 

  • “We should install a whole house fan, and swim more often at our local pool.”

• Action: This is what I need from you. 

  • “Can you please start calling around to get quotes? I’ll buy the kids new swim gear.”

• Benefit: This is the benefit to you / our shared goal. 

  • “We love swimming, and 90’s hip hop. I think this allows us to get through the Summer in a way that gets us both what we want, reducing our power bill and lots of fun activities.”

Here’s a SCIPAB that tees up what we do at Garden Labs:

S: Scaling a startup is hard — and in a rapidly evolving emerging tech space, it gets even harder.

C: While most scaling startups would benefit from a COO, finding the right one is daunting. You’ll want to take your time to ensure there’s a fit across vision, skillset and values.

I: But most startups don’t have the time to wait. The cost of continuing to execute without focus, or scale without intention, is too high. Also, the risk of rushing in and hiring the wrong COO is tremendous.

P: Drop-in the experienced team at Garden Labs. We support on both the strategy and operations front, as coaches and doers, to help you tackle today and plan for tomorrow.

A: Let’s have a conversation to see if the fit is right, and feel free to chat with teams we’ve supported before to understand where we excel.

B: Get the benefit of COO-support now, gaining not only strategy and operations project support, but an experienced thought partner to help you find your ideal COO and spearhead critical company initiatives.

✨ Pro Tip: Use the SCIPAB framework to organize slides for a presentation. One slide per letter. ✨

Some helpful call-outs on how I use the SCIPAB:

• Don’t. Forget. To. Pause.

  • After Situation – you want the “yeah, that’s obvious” head-nods. Nobody should be tightening up here.  

  • After Benefit – you’ll want to solicit input. If you’ve done a good job of being really concise with Position, Action and Benefit – you’ve tee’d up the exec (or group) for a real discussion. Let it happen!

• Don’t wander – get through the SCIPAB, avoid tangents.

Mastering the art of communication with executives is no sorcery - it's a skill that can be honed with the right techniques.

As with anything, the more you practice, the better you will be. Ultimately, when meeting with Execs, your goal is both to get through your message and to learn. Being really clear on your message will help you deliver it well, and will open your mind up to signals that you may be on the wrong path or have more to learn. 

<3

Amanda

Do you have other techniques or frameworks that you use to tee-up complex topics, especially with diverse or unfamiliar audiences?

Leave a comment

I’m really tickled by the responses that I’ve received throughout this series. Thanks so much to those who wrote in with your great questions. Stay tuned at the bottom of this post for a special offer! ❤️

Dear, New Ops Leader,

By now, you’ve done many things — and my guess is, given the elusive scope of your role and the pressure of today’s climate, that things have already gotten difficult.

You may have heard this before, but I want to point out an unfortunate truth:

“Under pressure, you don't rise to the occasion, you sink to the level of your training" - Anonymous Navy Seal

That’s right.

You might imagine yourself rising like a mythical Phoenix, achieving the unthinkable (and sure, it’s possible!)

But, it’s also possible, that without focus on your own development, you’ll show up like Kate Gosselin on Special Forces: World’s Toughest Test (IYKYK).

Source: IMDB

(Side note: I highly recommend this show. So many lessons in mindset > physicality, hubris, group dynamics. Tune in now on Hulu! and yes, that’s Scary Spice and Dr. Drew.)

So, today’s post is about investing in yourself. But first, a cautionary tale about sinking to the level of your training — quick story time :)

In one of my first Ops leadership roles, I was put in charge of a planning process for a 300-person organization.

After about 3.5 minutes, the pressure of the moment got to me, and I quickly defaulted to what I knew best at the time: relentless project management.

Going into a spiral. Anyone want anything?

Before I knew it, I had locked myself in a conference room and developed a Master Plan for how this planning process needed to play out for Optimal Success. My plan lived on a 300-row spreadsheet that thoughtfully (and neurotically) called out the discrete tasks that almost everyone in the organization needed to complete.

In short, I went insane.

What followed? Nothing better.

I, then, chased down the leaders in the organization (who were meant to be my peers, btw) for regular updates. I pushed that damn spreadsheet down not only their throats, but the gullets of their directs as well.

The outcome?

Not only did I create a situation where everyone ended up hiding from me — but I completely missed the opportunity to guide the process strategically, connect meaningful dots, find opportunities for acceleration (or cost savings). I missed the point of planning.

It’s a bit of being Heads Down (vs Heads Up), but really, it’s something I call: The Backslide.

Welcome to the Backslide.

I see this frequently with new leaders (and old): if not careful, in moments of pressure, we over-rely on our core competencies.

That’s not always a bad thing — especially since your core competencies are likely creative problem-solving, collaboration, and relationship-building. But it definitely becomes a problem when you over-rotate on functional competencies of yesteryears, or you lean on superpowers that are no longer fit for purpose, like:

• The product-focused-founder-turned-CEO who throws product feature ideas at an existential crisis, or even

• The Chief of Staff turned COO who defaults to a facilitation role when their leadership is really needed (👋)

In my story above, instead of assuming my strategic position (which is what the org needed most), I reverted to being a tactical task manager. 

So, how do you avoid this?

1. Cultivate self-awareness through coaching — more on this in a moment!

2. Invest in yourself.

Here is my quick Invest in Yourself List: 

• If you’re going to level-up in one area, make it your communication skills — Seriously. Let this become a superpower that you cultivate and you’ll find that you multiply your impact. Remember, it never stops! There are different subspecialties here that you can hone:

  • Communicating for clarity – what’s happening, what’s the cause, where are we headed

  • Communicating for action – motivating, inspiring

  • Communicating for influence –  persuading, enlisting support

  • Communicating in times of conflict - mindful, non-violent communication

• Take a pulse on your performance and perceived strengths — every 6 months or so, ask for feedback. Make the ask consistent (so people learn to expect it) and easy (just three questions):

  • In the last [quarter / half], when did you see me at my best? Why?

  • In the last [quarter / half], when did you see me struggle? Why?

  • What 1 thing can I do to drive more impact [on X-initiative, or at company]?

• Build your tribe — we talked about the value of relationships at other companies (huge for perspective); but these relationships can also be your support system and your link to other advisors:

  • Keep a log of Hard Things I’m Struggling With — there are likely 2-3 on there that are universal to all startups / companies. These are great topics for peer calls. Don’t limit yourself to other COOs either. Build relationships with CTOs, Product Leaders for even more perspective.

  • Here is a very standard agenda for these calls that you can start with:

    • How are things going? Anything new? (publicly available things come out here — new launches, new funding rounds, new leadership — learn about their business / world this way).

    • I have a thing I’d love your thoughts on… (have you observed / experienced anything similar? do you have any advice? know anyone who is best-in-class at things like this?)

    • Can I help you in any way? (find opportunities to offer support / follow-through and build the relationship for the long-term)

• Get a coach — coaches are NOT one-size-fits-all. You want someone who both has the unique expertise or perspective you need and someone you can see yourself opening up to. I always recommend speaking with 3-4 coaches in the same 2-week window before choosing one. That way, you don’t just land with the first, and you get a real feel for fit.

  • Ping me, if I can help. I coach and advise a small portfolio of CEOs, COOs and Managers (at companies as small as 15, and as large as 15k). Our focus tends to be on the things I talk about frequently here: navigating leadership team dynamics, managing your mindset… but also on company-building things like: scaling (or right-sizing) orgs, fleshing out your strategy, and more.

✨ I’m going to open up a couple slots on my calendar for a few quick hellos — if you would like to explore working together in some capacity, click here to book some time. ✨

Remember, new Ops leader: this is a marathon, not a sprint. You got this. You’re not alone.

I hope you all enjoyed this series as much as I did (impossible, but a girl can dream).

Sending all my <3…

Amanda

This series is 5 parts, find the other posts here:

Part 1: Dear, New Ops Leader...

Part 2: Pick Your Boulders

Part 3: Don't Lick the Cookie

Part 4: Stay Heads Up, While Heads Down

📣 Two quick things, before signing off (and on to our next series…):

1. I recently sat down with Caro Griffin of Opsy fame and we had a fun convo. Click here to give it a listen!

2. If this series was helpful: it would mean a lot to me if you would share Part 1 (now with all Parts linked) on Linkedin, Threads, Twitter, or with your favorite Ops leader.

Got a question? Just reply here! I’d ❤️ to hear from you.

Thanks for reading! If you know someone ramping into a new ops lead role, share this piece with them (they will thank you!)

Big thank you to the incredible Yoko Li for this original cartoon, which captures the spirit of this post perfectly :)

There’s a distinct feeling I’ve had in leadership meetings – a pounding in my chest – whether it’s a large in-person meeting, or staring at a dozen faces on a Zoom screen. It typically arises not as a response to what is being shared in the meeting, but from what I’m not saying. 

Because, instead of taking the leap and bringing up that concern about our launch plan (and risk upsetting Jon, who has been working nights and weekends on this), or surfacing that unaddressed risk in our financial model (and rabbit-holing the discussion for 20 minutes), I decide to just not go there. Maybe the issue will resolve itself naturally.

It’s a feeling that I now can identify as fear – and looking around, I can’t help but wonder who else in the room might be feeling the same way.

The problem is, going there is exactly what makes these operating exercises valuable. 

Rather than focusing on day-to-day execution, something most startups excel at, strong operating practices (like goal-setting, planning and business reviews) require something different. Teams must use a wider lens (much wider than the one they look through every day), deeply consider future states (possibly distinct from the one they are currently chasing), and agree on a concrete course forward (one rife with unknown-unknowns).

This requires that teams put all of their cards on the table, and enter a space of reflection versus reaction. That they express the underlying concern that is preventing them from buying in completely. That they sidestep fear, for even just a moment, in order to envision what could be true.

Slowing down to go fast

Now, before you start grumbling about how you don’t have time for this – you’re running a startup! You need your teams to just “move fast, break things!” (or insert your favorite mantra here) – please, hear me out. 

Behind these pithy slogans tends to be a dangerous assumption that everyone is on the same page – that they know what to move with urgency towards, and what can break; that they know how the company is performing, and that they are interpreting and processing the events of the market in a similar fashion.

But I’ve found that in most teams, especially those operating in complex environments while rapidly shipping, this is simply not the case.

And this problem compounds as teams start to scale. In fact, I regularly observe teams grow from 10 to 25 and completely lose the thread on what they are there to achieve. During times of change, execution is no longer about staying heads-down and building – instead, it becomes about:

Staying grounded on a thesis and figuring out how to get smarter over time as a team.

Saying “no” to countless distractions and focusing on making the right few bets.

Bringing in and properly utilizing new skill sets to expand the team's capabilities over time.

The above requires intentionality and real alignment on what you are going after, and what really matters along the way. To achieve this, as a leader, you need to acknowledge and help mitigate fear.

In this piece, I’ll cover a few common fears that plague all of us in the workplace, particularly around goal-setting, and I’d like to offer a few tactics for keeping them at bay. 

In most organizations, goal-setting tends to be a time when hopes and fears are translated onto a page.

These lessons were born from patterns that I started to recognize during nearly a decade leading dozens of leadership teams at PayPal, and now as a COO advisor to early-stage startups. 

Whether you’re considering H2 planning, or just navigating the difficult terrain of today’s market, I hope you pick up some practices that you can apply to help keep your teams aligned, grounded, and operating with less fear. 

5 COMMON FEARS (AND HOW TO KEEP THEM AT BAY)

So, let’s dig right in and go through a few scenarios that tend to undermine the very collaboration needed to get the most out of your operating practice (along with some fictional archetypes to help bring each to life).

THE FEAR OF FAILURE 

Julia is a seasoned SVP who refuses to set an aggressive target for her team. She’s learned from previous roles that if she sets a target and misses, it’s likely that her budget will be cut next year. So instead of buying in and going big, Julia goes for a modest target that she knows her team will over-perform against.

Tyra is gun-shy to agree to a target, and she’s gone silent on the email thread. Why? Because the last time she went “big” and failed, she felt like she lost vital ground with her peers and her CEO. The culture claimed to believe in “fail fast” – until Tyra did. 

Golden Rule #1: Set the tone.

As a startup executive, you are leading everyone through a grand expedition — what you're attempting has never been done before, and it's going to require that you utilize every ounce of skill and resources that you and your team have at their disposal. 

But at a fast-growing company, it's very easy to become hyper-focused on your piece of the puzzle, rather than how the constellation of pieces fit together. This is why team-building exercises, like ropes courses and escape rooms, are a favorite on leadership team offsite agendas: to remind you that you’ll accomplish much more together, versus going about it alone. 

The act of “team-ing” is a muscle – and if not exercised, it will atrophy.

So, at the start of a goal-setting exercise, or better yet, throughout the quarter – remind your leadership team that they are, in fact, one team. Reinforce the expectation that everyone works together to reach the summit. Also, state the rules of the game. Some tactical tips include: 

Read the full article here.

✨ Subscriber Question ✨

I’d love to know what you subscribe to or read on the Wednesday and Sunday reading breaks you mentioned. The outside in awareness is something that I’m working on getting stronger at this year so any suggestions would be very welcomed. 

— Amazing, Incredible Subscriber (in response to Stay Heads Up, While Heads Down)

Dear Reader,

It’s daunting trying to prioritize between the endless resources you can theoretically incorporate into your weekly routine, and I will confess, I switch mine up from time to time.

To shed some light on one way to approach things, here’s a bit more about what I do:

Wednesdays – “happenings”, things that are time-sensitive in nature. Information I might want to know mid-week, in case I want to show up smart somewhere…

• Twitter – I do a Twitter sprint first-thing in the AM (my feed is curated around web3, AI and any industries specific to my portco / clients — pick your poison!)

• Morning Brew (sent daily!)

• The Information – they tend to have helpful exclusives

• Linkedin headlines – I peruse the Top News 

Bonus: Fridays – roll-ups (this is an extra, when time allows)

• Find a roll-up specific to your industry

  • Crypto/Web3 – Bankless

  • VC-backed startups – TWiS (This Week in Startups)

• Let someone else curate the most important news for you! 

  (Hint: I’m currently testing some customized news roll-up platforms, stay tuned for my top pick)

Saturdays – for more blue-sky, interesting stuff. Less time-sensitive information to consume, the goal is learning / connecting dots.

• Stratechery

• Not Boring

• Invest Like the Best (podcast)

• Implications

• The Profile

For commutes – learn things from smart people:

• In-Depth (First Round Review)

• Lenny’s Newsletter 

• Masters of Scale

• TED

• The Knowledge Project

• Lex Fridman

There are endless ways to design your personal information-absorption strategy. Carve out dedicated, recurring, time (a crucial step) and pick a few resources that feel engaging and easy to read. Sample different things and don’t try to “fill your funnel” all at once—get in the groove and build up. Hope this helps!

<3 Amanda

Got a question? Want some free advice on a sticky situation you are facing? Just reply!

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This part is all about staying in tune with what really matters in that company you’re helping to build.

Let’s remind ourselves of something: you’re in this role because you’re great at solving problems, and we all know that you don’t half-ass nothin’. But when you go “all in”, you might (ok, you will) lose the forest for the trees. 

It’s easy to understand why — while everyone is heads-down on that new feature, or closing that big customer, you see opportunities to resolve issues and remove bottlenecks that surround them.  

This means you naturally start to focus on things that fall outside of what can be thought of as the “core business” — things that are:

• Really deep in the weeds – like quickly resetting your compensation framework globally.

  • The risk: you’ll be dissecting the bark on the tree, and will lose your view of the forest.

• Really meta – like helping teams work smarter across geographies.

  • The risk: you’ll be contrasting and distilling themes across “beings” in the forest, forgetting that they are trees.

• Really peripheral – like evaluating new vendors for that thing that costs you a ton of money every year.  

  • The risk: you’ll closely follow a trail, only to find yourself outside of the forest completely.

The best Ops leaders learn to balance their hyper-focus (heads down), with some perspective (heads up).

This balance helps them effectively filter signal from noise, make wise decisions (notably, on their Definition of Done), and roll-out the right things in ways that garner adoption. 

Let’s break down how to effectively do that… AKA:

Stay Heads Up, While Heads Down

1. Be a humble truth seeker - know the business, and the reality of how the team is performing.  

2. Know thy context - keep your finger on the pulse of market dynamics, industry trends, and what your frenemies are up to.

3. Stay grounded - know employee sentiment, and be led by first principles. 

Without these things, you’ll be off-balance and risk becoming out of touch.

1. Be a humble truth-seeker

It's easy for your view on the business to be developed by proxy - i.e. things are going well (or terribly) if the CEO / CPO / whoever, tells you they are.

I’m here to encourage you to develop your own view.

A humble truth-seeker hones in on the measures that matter most (using acumen and strategic context) and really watches them. If things look awry, they engage curiously - asking questions for the good of the group, in order to get to the truth of what's not working and why. 

Your truth seeking will depend on your stage. If your team is pre-product/market fit, make it your business to know the guiding thesis of what you’re building and how your team is viewing north star metrics. If you’re in “scale” mode, know how things are going across your funnel and be fluent on the rationale for your roadmap. 

How I’ve done this before: 

• I keep saying this, and will repeat it again: build strong peer relationships. The views of a diverse set of peers will be one helpful input for you.

• You’ll also want to regularly attend and engage in product reviews and finance rhythms. Discussions covering progress vs expectations are great place to learn, contribute, and stay close to what’s happening.

Pro Tip: don’t forget that, regardless of what you’re focused on at the moment, your primary focus is always on helping the company reach its potential. Wear the hat of someone with a shared mandate in these meetings. Whenever possible, offer solutions to bottlenecks that are within your sphere of influence. This will ensure you’re attending as a true partner at the table vs a critic or spectator.

2. Know thy context

Start-up land forces you into a perpetual state of survival, obsessing over the problems looming largest, before pivoting and tackling the next most urgent thing. For Ops leaders, the "problem stack" tends to be "internal" — meaning the de-bugging you do serves the inner-workings of the organization versus the market.

It’s really important, though, to remember that you’re designing and building systems within an ever-evolving organism, in an ever-evolving industry. Context matters.

When you find yourself endlessly doom-scrolling your emails or Slack, consider that you might be operating in an echo chamber of your own company.

To remedy this, create space for “heads up” moments & compare notes with others.

How I’ve done this before:

• Wednesday and Sunday reading: Have short blocks in your week for reading up on what’s happening in your market / industry. Some like to ingest from Twitter multiple times a day — I find concentrated sprints twice a week much more manageable.

• Friday calls: I hold time every other Friday for calls with other operators in similar roles at other companies and investors / advisors. These are informal opportunities to compare notes, brainstorm, you name it. I get a TON of mileage here on the state of the hiring market (something that is typically hard to gauge from the confines of your home office).

• Syncs with market-facing team members: when possible, I like to set up semi-regular and totally informal syncs with team members with a great pulse on the market. Super plugged-in BD managers, for example, are a great connection point to customer / market context.

3. Stay grounded

Lots has already been written about how easy it is for a leader to get out of touch with the ground-truth in a company.  

It’s really important for an Ops leader, specifically, to have a sense of team sentiment. This helps you to “read a room” more accurately and know how to navigate complex issues.

There are lots of ways to do this poorly — like the time I worked for a leader who did a lot of "rah rah culture stuff" right after a layoff; or the time I kicked off a cross-functional strategy project in the midst of a busy product sprint.

It’s actually laughable how easy it becomes to get so wrapped up in your stuff, your timeline, your tool that you forget there’s this whole company out there, doing things.

So, before you work yourself into a tizzy — try these things:

• When rolling out a new idea, start with principles and remain flexible on implementation details (especially tools) — allow the teams closest to the problem to have the loudest voice there. As you start to encounter bumps in the road (inevitable with anything new), stay close to key team members for the ground truth, and focus on aligning the team around key principles. 

• Build an informal board of employee-advisors. Compose your “board” with a diverse and mature group of truth-tellers who will give you the unfiltered facts. (note: not gossip — but truth on how your ideas are being received, how teams are feeling, and why).

• If you’re not in an office, randomize your encounters. Consistently schedule 1:1s with various members of other teams to broaden your vantage points on key company issues (here’s a Slack tool I’ve used for this in the past).

Your unrelenting focus is your strong suit — make toggling that focus between the weeds and the forest your superpower.

Thank you for reading. Until next time!

Click here for Part 5.

<3

Amanda

Find the rest of Dear, New Ops Leader here:

Part 1: Dear, New Ops Leader...

Part 2: Pick Your Boulders

Part 3: Don't Lick the Cookie

Part 5: Invest in Yourself

I truly do this for the DM’s. If anything above was helpful to you, or you have a question, or a joke — I’d love to hear from you. Just reply!

So, you're in your new role, you're staying calm while problems rain down around you, and you're attempting to pick your boulders. At the same time, you can't help yourself — you really do want to add value and get some wins on the board, and there are opportunities to do so everywhere.

This brings up a related, but distinct point that really matters: Don't Lick the Cookie.

Now, if you have siblings, you already know what this means. But, just in case: "cookie licking" is the act of — you guessed it — licking a cookie so that your brother / cousin / spouse (just for example) doesn't take it.

In software development, especially in large companies, "cookie licking" can look like a team putting something on their future roadmap (like "AI" or "new feature X"), effectively staking a claim over it and preventing other teams from working on it.

Cookie Licking isn't always a conscious, greedy act. It can be done by accident, by someone with great intentions… like you, new Ops Leader. ❤️

Let me share an example.

What it looks like to Lick the Cookie

One of the boulders that you take on is shifting how teams companywide communicate with one another. You and the rest of the exec team agree that everyone is over-utilizing meetings and too much time and knowledge is getting lost.

After a lively discussion, you all decide to test the use of video as a medium for asynchronous internal communication — so you get to work:

• You scour the market and select a tool that you'd like to test in one org. The test goes well, so you roll the tool out companywide.

• You then decide that modeling is important, so you shift a few high-visibility exec comms to video — that went well!

• And then you decide that expectation-setting might be a problem — so you get involved with new hire onboarding and interject a video there for good measure.

The boulder officially gets off the ground — adoption is picking up, and you're hearing good things. That’s a win!

But then 3 months go by... and you are still the de facto "Head of All Things Video." At this point though, the company’s video needs have shifted, you've moved on to more pressing issues, and video stuff keeps slipping further and further down your list.

Uh oh. You've licked the cookie.

What happened?

While you were making magic happen, stacking those wins, you forgot that your job is to actually work yourself out of a job.

And because you’re the COO, and you’ve associated this focus area with your name:

1. The general belief will be that you’re taking care of it, and…

2. It might feel high-stakes for someone to come and “take it away” from you, so…

3. Other teams or leaders will likely not work on it.

Having seen this movie a number of times, I’ve learned something:

After some time, your involvement in something (as COO) prevents others from stepping up to lead.

It could happen other ways too

If your mandate as COO is really broad, like “I’m here to make the company work better” — you might believe you should volunteer for every effort that lines up to that outcome:

• Our employee onboarding is outdated? That’s really important. I’ll fix it!

• Our internal reporting is lousy? On it!

• We need to retool customer support to better utilize AI? Got it!

Or you beat the drum of “we’re the process [or data] people!” You might create the belief that you need to be in every process flow, or data effort.

Eventually, you become a single-point-of-failure (sometimes, out of complete exhaustion) and you crowd out the potential leadership and contribution of others.

The result is just as pernicious as the greedy cousin licking the last Oreo (even while well-intentioned).

So, how do you avoid licking the cookie?

For 80% of the things you touch: your job is to test, iterate (or kill), and gain sufficient support and momentum for something... before you officially make it someone else's job.

In doing this, you are as much an internal talent scout as you are a problem-solver. Eventually, and especially when scaling, you want to become best-in-class at the motion of lining up talent with problems, resources and real ownership — and sending them on their way.

This is the game of handing out cookies, versus licking them.

There are a few aspects of this that really matter:

1. Know your Definition of Done.

Step back and ask yourself: how far do I need to take this before it becomes a nicely packaged problem (or validated solution) that can be handed to someone else?

Discuss this transparently with your peers in advance, so that there is no confusion.

This does not mean you’ll drop it like it’s hot as soon as you reach the point of “Done” — but it does mean you’re clear-eyed on your scope, role and intended outcome coming in.

2. Start to identify and enroll others early

I’ll be drafting another post on how to spot underutilized talent internally, but for now: scan for passion and aptitude before job title. If this project truly has the support of company leadership, it’s going to be an excellent growth opportunity for the right person. It helps, by the way, if that person has more ground truth than you — as they’ll likely do a better job of rolling out the right thing.

Important, though, is the “enrollment” part — it’s not enough to find someone and loop them in. You will need to help ensure they have the support they need to be successful. This will require buy-in from their manager / team, possible reprioritization of their workload, and maybe even budget. Lean on your peer relationships to make these happen.

Finally, if you truly need to hire for this thing going forward, engage the future boss of this potential hire early. Help with knowledge transfer, but leave ownership of the search to them.

3. Resist the urge to parachute back in

Ownership will need to be communicated, and reinforced over time, especially when things go wrong. Your peers may still look to you for updates, or bring you problems. When that happens, extend support, but don’t parachute back in. This is another chance to not lick the cookie.

Also, be helpful if / when ownership needs to shift again as the company scales. It’s likely!

Tying it all together

Sometimes, you see COOs that are great executors, but lousy at the transition part. This causes friction and shortens the shelf-life of the solution at-hand.

You sometimes also see the COO with the desire to “empire-build” (ie. accrue functions and direct reports for the glory — an anti-pattern, for the record). Instead of transitioning at “done,” they build teams (under themselves) to support the solution going forward. This tends to erode trust with peers and leads to an unwieldy organization full of shadow-functions and unclear mandates (like the COO who runs operations, legal, IT, comms and product marketing).

S/he may be in that position because that is what is truly best for the company right now — or, it may be because s/he licked the cookie.

By focusing on smooth (and timely) transitions, you’ll model that “wins” happen not by amassing resources or glory, but by solving problems in a way that is sustainable.

I will now accept my award for saying “lick the cookie” 23 times in a blogpost. 🆒

Ready for Part 4 in this series? Click here.

Thank you for reading. Until next time!

<3

Amanda

Find the rest of Dear, New Ops Leader here:

Part 1: Dear, New Ops Leader...

Part 2: Pick Your Boulders

Part 4: Stay Heads Up, While Heads Down

Part 5: Invest in Yourself

I truly do this for the DM’s. If anything above was helpful to you, or you have a question, or a joke — I’d love to hear from you. Just reply!

If you know someone ramping into a new ops lead role, share this piece with them (they will thank you!)

Part 2: Pick your boulders

Thanks to a former boss, I regularly think about the story of Sisyphus. If you haven’t heard it, in ancient Greek mythology, Sisyphus was a king, punished for his hubris. Hades sentenced him to push a large boulder up a hill, only to have it roll right back down, for ETERNITY.

(For all of you super productive Ops leaders out there, I know you agree that this might be our worst flavor of hell.)

I bring this up, dear new Ops leader, because throughout your tenure in this role, you will be punished presented with countless hills and insane boulders — and sometimes, you will have the opportunity to choose which are worth pursuing.

Some boulders will be worth it, and others won’t.

• That large effort to implement a new financial management system that will allow you to finally get a handle on your cash flow and runway? Probably worth it.

• That poorly-defined initiative to “improve how we work” company-wide? Slow down and think that one through.

But wait, isn’t that last one simple? Just a few templates and a wiki, right?

Sure, could be — but only under a few conditions:

1. Everyone you work with is a machine that can be reprogrammed with the flip of a switch.

2. The change is really simple, and you can just do it or …

3. The change requires some buy-in (and behavior change), but your entire leadership team is really aligned on following through, plans to model the new behavior(s), and will support their teams through the change. 

The problems occur when you confuse #3 for #2 — and that happens, a lot.

That’s because behavior change is often harder than we imagine it to be. Also, your peers (and CEO) might be — ok, probably are — underestimating the complexity of what they are asking for. They may also be neglecting to internalize what the change means for them, personally.

For example: “we should improve how we do meetings!” could sound like a set of tools or guidelines that go out to all teams with standards that everyone follows (simple enough, right?)

Quickly, it becomes clear that the worst meeting offenders are on the exec team 🤭 (less simple)

Or, “we need to improve our hiring process” could sound like process tweaks for recruiters (great!)

But once you dig in, you realize it actually means more upfront planning and preparation is needed before roles are even opened, and that is a more complex problem to solve.

Know the warning signs.

Don’t worry, new Ops leader, you’ll become a better boulder picker over time.

And soon, you’ll even be able to spot peak “Sisyphus roles” coming in. (You know, the roles that are set up to ensure you’re boulder-pushing on Day 1). It’s when you hear things from a CEO like:

• “I need an Ops leader to keep everything organized” (at our startup, where nobody knows which way is up)

• “I’d like to move all of my direct reports under my new COO, so that I can just focus on Product (versus all of this ‘management’ stuff).”

• “We don’t have anything documented, but we are going to scale headcount 5x this year. Our Ops lead is going to lead the charge.”

These are likely no-win scenarios – and do NOT let your confidence, optimism or excitement tell you otherwise (remember what got Sisyphus into this hell to begin with: hubris).

In all of these cases, things start off just fine. Some boulders actually get off the ground – but you know what happens next.

Boulders are everywhere — pick wisely.

No matter the ops role, it’s likely that by the time you arrive, the team is in some form of operational debt. You’ll see many opportunities to add immediate value, but before you jump in and start pushing — take a moment to ask yourself some questions.

1. “Will the effort I expend on this have the potential to return 10x the value?”

2. “Will this require unrealistic (or unsustainable) amounts of behavior change?”

3. “Are my peers (the exec team) really at the table here – engaging, owning pieces of this, stacking resources, getting curious?”

4. “Is this Initiative 3 on a list of things I’m going to try and do?”

Here’s a simple decision tree that you can use:

Misjudging the size of the boulder, or grabbing too many, is not the end of the world. But it tends to kick up lots of confusion and exhaustion around you, draining precious time and energy away from really important things.

So, focus. Your mental health will benefit from it, and your team will thank you.

And if you’re wondering what happens when you choose the right boulder: Yes, it comes rolling back down anyway, always. That’s startup life! 🤷🏻‍♀️

Don’t worry. You got this.

(Part 3 is here!)

<3

Amanda

Find the rest of Dear, New Ops Leader here:

Part 1: Dear, New Ops Leader...

Part 3: Don't Lick the Cookie

Part 4: Stay Heads Up, While Heads Down

Part 5: Invest in Yourself

This series was inspired by subscriber questions! Do you have one? Just reply here! I’d ❤️ to hear from you.

Thanks for reading!

Well, remember when I asked for questions from you all?

I heard from a few of you (very cool people, I might add) and learned that you’re freshly-minted Ops leaders. Congrats/secret handshake.

This series is for you. For the next few weeks, I’ll be sending notes weekly to relay a few things I wish someone would have told me about Ops leadership roles.

As always, I’d love your feedback, thoughts or questions — so reply, or hit the comments.

Part 1: Welcome — Don’t Panic

There are ops lead roles popping up everywhere – for good reason, too. Gone are the days of f*cking around until the next round of funding. Today, execution matters.

A strong ops lead is a company-impacting hire — but it’s also a really hard job. It’s generally poorly defined, and when a company is really young, its scope tends to be everyone else’s problems.

So, I sat down and wrote you (yes, you, New Ops Leader) a letter. It's going to be in multiple parts, because as it turns out, I have a lot to say!

1. Welcome to an incredible (but mostly thankless) job.

This role is all about enablement, which means you’ll be working mostly behind the scenes, problem-solving to make the company better. It’s going to be things like conflict resolution, process improvement, and digging into some really unsexy weeds to get things working that will be your “wins.” These things tend to be hard to measure and they tend to overlap with other people’s jobs, so attribution is damn near inappropriate. Get used to untangling things and exiting stage left, because that’s the job! 

How will you know you’ve been successful, you might ask? When Jill finally breathes that sigh of relief because her thorny, company-level blocker is now solved. Or when that backend eng team goes from massive gap in resourcing to stellar new hires onboarded, and fast. Or when you see nods and smiles in meetings instead of frowns. You start to become attuned to these things after a while – but catch the glimpse while you can, because the business moves on quickly. 

2. Don’t panic. 

You will see Everything. That. Is. Broken. Do Not Panic.

You’re in this role because you have a knack for spotting and then solving problems. But, fair warning: before you know it, it’s going to feel like Problem City, Population: 1 (you).

Before you go full Carrie Mathison, remember: this is going to be a marathon. 

Believing that every problem is existential and equal in urgency will burn you out faster than you can say “operational excellence”.

And while you’re swimming in the catastrophe of it all, try not to psych yourself out. Your conviction will bounce around, and that’s ok. If you’re looking for reasons this company will fail, you’ll find them everywhere. If you’re looking for reasons you’ll be uber-successful, you might find those too. Make Friends With The Monster Chewing On Your Leg by Molly Graham covers the mental struggle really well. 

How you handle problems will become a skill and eventually, a matter of style:

• Do you freak out? I once had a boss who lost her shit every time she learned something was awry (which was at least weekly). No matter when you encountered her, there was always something to panic about. I’ve never left a team faster. Not only did she create a culture of complaining and alarmism around her, but she quickly lost credibility with her peers (a la Chicken Little).

• Do you become the bad cop? Interrogating others on the presumption that they should have it all figured out by now? That’s not going to work.

• Do you avoid? That’s probably not the answer either.

Remember that when there is turbulence, passengers watch the flight attendants. If they are racing through the aisles with genuine fear in their eyes, start praying. If they are fine, keep sipping your Miller Lite.

• Can you calmly and objectively file the right things away under “not a ‘today’ problem?”

• Can you effectively elicit urgency and action, without defensiveness?

• Can you enlist support from managers and peers in a way that ensures the ownership resides where it’s needed (with the teams doing the work?)

These skills (prioritization and communication) can be developed, if you work at them. It also really helps to have the support of a coach, and some perspective from Ops leaders at other companies.

You’re not going crazy. It’s all normal. You got this.

(Click here for Part 2)

<3

Amanda

Find the rest of Dear, New Ops Leader here:

Part 2: Pick Your Boulders

Part 3: Don't Lick the Cookie

Part 4: Stay Heads Up, While Heads Down

Part 5: Invest in Yourself

This series was inspired by subscriber questions! Do you have one? Just reply here! I’d ❤️ to hear from you.

Thanks for reading!

There was a massive amount of confusion internally – who does what? – and that chaos was compounded by the fact that our CEO hated org charts. Publishing one was off the table.

I also once worked in an organization who cherished their prized org chart. When it changed, it was the talk of the town! 

In both of these cases, the org chart (or lack thereof) was not the problem. It was the culture. 

Org charts – the document-of-record that outlines who reports into whom at a company – stir up lots of feelings. They have a reputation as unnecessarily bureaucratic, fixed, antithetical to startup culture, and political. 

Because of this, I’ve seen startup leaders back themselves into a corner, believing they can get away with simply not having one. This is a mistake.

The Concerns

Let’s talk about what is scary about org charts, and what questions exist below the discomfort.

I’ve found that there are a few common reasons why startup founders bristle when you bring up the idea of an org chart:

1. They feel bureaucratic

Many org structure documents connote a “chain of command” and can feel very stifling. They also evoke a certain decorum that can feel dangerous.

Who needs to “approve” my thing? Am I allowed to talk to John, or do I need to talk to his manager first? If I talk to John’s manager, is that considered an escalation? If I have a good idea and go to my VP, is that going over my manager’s head?

From what I can tell, the core fear at play here is, the hierarchy, and its implied approval loops, will kill speed, experimentation and divergence. 

Instead of worrying about “the machine” and its impact on your culture, ask yourself:

Is it crystal clear who is directly responsible for our most mission-critical efforts? Does this person have the decision rights, resources and support needed to be successful?

2. They feel fixed

Every leadership team I’ve ever worked with (or on) has had gaps. It’s the nature of teams – they are fluid – and in the formative years of building something, you’ll be a long way from “perfect.”

This reality can make documenting your org feel like a step too far, and can trigger thoughts like:

• Can’t we get things dialed in a bit further before we commit this to paper? 

• Will this mislead Jason into thinking he’s the head of product? What happens when we hire Melissa as his boss?

• Eek, now that this is on paper, it reminds me that I really need to talk to my co-founder about his role … 

For many CEOs of young and scaling companies, this triggers another fear: am I locking in something that is fundamentally broken?

If this fear is coming up for you, consider asking yourself:

Am I prioritizing hard conversations, or avoiding them? Am I as focused as I should be on finding and closing the talent we need?

3. They create politics

There is this misconception that I’ve heard that org charts create politics. That the very presence of a leadership structure creates land-grabbing, power plays and prevents the right ideas from gaining traction.

This tends to lead founder CEOs into the belief that hierarchy is bad, and it’s best to be flat. 

Well, I’m here to tell you two things on this:

1. Whether you have it written on paper or not, you have a hierarchy. There already exists a small group of people, either formally or informally, who tend to influence the most critical company decisions. 

2. The leaders you hire – and how you engage them – will have more to do with how political the environment becomes than any org document.

If the above resonates, consider asking yourself: 

Am I being fair and consistent with how I engage my leadership team and make decisions? Am I hiring leaders that will advocate for the best ideas, regardless of source?

4. They feel antithetical to the startup ethos

If you’re drawn to startups for freedom, ownership and speed – the feeling of being placed in a box, under or over someone, just doesn’t feel right.

Especially in crypto/web3, where decentralization is core to the ethos of the space, the conflict is even more acute – how can we run our internal organization in a way that is inconsistent with the values we set for our external community? 

If this is a concern, consider asking yourself:

Are our values known, understood and reinforced internally? Do we operate in a manner that is consistent with our values?

The Cost of Not Having One

You may have figured it out by now, but this article is not about org charts :)

It’s about the unaddressed people, culture and operational issues that get projected onto one.

But when you decide you’d rather avoid those issues than face them, and worse — when you opt to obscure them — you create more problems for your teams:

Lack of Transparency 

For better or for worse, organizational charts provide a map of the terrain that guides organizational practices, like reporting. Absent this map, and especially once a team grows to a certain size (above 30), communication doesn’t just happen. It takes intentionality – an org chart is one way to identify who needs to speak to whom.

Where there is a lack of transparency, you’ll very typically find…

Politics 

Yep, that thing you were trying to avoid is now a problem. It tends to be out of survival that these things emerge: because there isn’t a formal and transparent organizational structure, information is not shared symmetrically and because of that, information becomes currency. Being “in the room” becomes evermore valuable and you’ll find managers forming alliances to get their decisions made and work done.

Those who “play the game” progress, and those who don’t tend to develop… 

Learned Helplessness

Without a sense of transparency or fairness, teams start to lose their sense of ownership. This starts with sluggish decision-making and can turn into a full-blown sense of helplessness, if left unchecked. Sentiments like “why even bother?” creep in and are hard to shake.

Now, before you all jump to a new tab to start updating your org charts – here is your takeaway:

Be explicit with decision rights and consistent with info-sharing. 

That is 80% of the battle.