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.

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

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!)

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.

I had the privilege of gaining quite the subscriber base after publishing this piece about fear. In my coaching and advisory practice, I work daily with founders and startup execs on many of the fear-mitigating tactics outlined in that piece — and I know, firsthand, that these tactics and practices are never as easy or simple as they sound.

So, we’re going to try something:

What thorny leadership or operational challenge are you suffering through at your company?

I know you have stories, and there might be one thing that you could use some advice or outside perspective on.

Maybe it consists of a wild concoction of motivations, quirks, fears and alliances (they always are) — or maybe its just your usual startup chaos stuff.

Either way, I’d love to hear from you.

Click here (or reply to this email) and tell me what’s going on, and share a problem that you’d like some outside perspective on.

I’ll pick a few and will do my best to share some guidance, tactics, tools, encouragement, maybe a bad joke — and will publish it (with all aspects completely anonymized) in a future newsletter.

Think of it as a strategy, ops and management advice column that helps land practices in the context of real-life. But career advice for COO-types is on the table too.

At a minimum, we’ll get to know each other. At best, we’ll all benefit from the understanding that we’re not alone.

I’m thrilled you’re here!

If you haven’t already, take a look at this prior piece on distilling your guiding thesis. It’s a helpful companion exercise for anyone preparing for planning or goal-setting at a startup.

Please consider sharing this newsletter, especially if you have a friend who:

• joined a startup and is attempting to "fix all the things" with tools/process/unicorn hires

• has cracked a code with their product, but now has a company to build

• wants to go down the treacherous road of being a startup COO and wants a friend along the way <3 

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Until next time,

Amanda

Learn more about me here

Today’s Track of the Day:

While it’s fun to jab at how everything nowadays is a “flywheel” (or how we need to constantly “unpack” things 🙄) – there is one buzzword that I’m going to keep using until the cows come home, and that is “alignment”.

It’s not just that I love using the word “alignment” (though I do). It’s that I think the importance of it is highly undervalued in startups. 

So, in this piece, let’s talk for a moment about alignment – what it is and what it isn’t, and why it matters in a fast-moving startup.

First, a quick definition via analogy – (my father-in-law is a long-time mechanic and I’m going to attempt to make him proud here – so buckle your seatbelts, I’m going for it…)

If you’ve ever owned a vehicle before, you know that a car regularly needs its alignment checked.

Mechanics hoist your car up on a rack and make adjustments until all four wheels are parallel. When a vehicle’s tires are in alignment, a car moves straight ahead and all tires wear evenly. But the more you drive, the more your alignment starts to slip.

It happens in tiny increments over time, so slowly you may not notice it at first — and when you do, you may excuse the issue as an uneven road, or nothing to be concerned over. But eventually, if not corrected, you start to really notice your car veering to one side of the road. As your tires and wheels incur damage, the once-simple process of driving becomes more difficult and dangerous.  

The same thing happens within startups, and within companies of any size. 

Just like in a vehicle, when teams fall out of alignment:

• You hear it – a below-the-surface grumbling, or loud shrieking (depending on your culture). Sometimes it sounds like “who even knows what marketing is up to…”

• You see it – a team may be burning out, not getting the support they need while the demand on their function continues to grow

• You feel it – you need to constantly intervene to weigh in on priorities, resources, commitments.

It’s exhausting – and after some time, it’s a terrible drain on resources and worse, morale. 

Alignment is not about the “stars aligning” (it’s more than luck!), or seeking uniformity in plan or approach across teams (no way). It’s about ensuring that when you hit the accelerator, you don’t fly off the road. 

What Alignment Looks Like 

Ultimately, alignment between two teams (or broadly, across a leadership team) boils down to two things:

1: We can agree on where we're headed and what paths we’re willing to explore

This agreement is not just about the “final destination” but also about the few critical pit-stops along the way. Vision is easy to latch onto, and we’re all pretty clear on what’s happening this week and next – but what assumptions are we making about what happens in between? Can we agree on 2-3 paths that give us the best chance of getting there? 

This shared medium-term perspective in a large company might be referred to as “strategic alignment” where the pinnacle of alignment looks like teams and resources lining up beautifully with a declared strategy.

In a startup, this level of alignment happens when you can agree on a thesis. Here is a quick exercise to help you start to align on yours.

2: Along the way, we will make hard decisions that keep us moving forward, together 

As we work alongside one another, and learn what actually happens when we start to build / test / grow this thing – how likely are we to support the right efforts, and importantly, de-prioritize the right distractions? 

Note: this is the collective “we,” not the local “we.”

When seeking alignment across teams, it tends to come down to prioritization and resource allocation. When two teams are well-aligned, they generally can agree on how to deploy resources (both time and budget) at a high level:

• Product and Engineering can tell you which 3 releases are the most critical this year, and what work should come before anything else.

• HR knows how to allocate recruiters to their hiring pipeline, and will prioritize hires that are tied to critical efforts.

As you scale, and you have multiple products in the market, or multiple units that are growing concurrently – this becomes really hard. This tends to be when you see people playing with org structures or incentives to address this.

For most startups, especially those with teams over 30, I recommend a set of company-level goals with regular checkpoints for discussion (monthly or quarterly) as a way to drive alignment across teams. 

What Alignment Doesn’t Look Like

• We agree on everything, all the time – nope. Productive divergence (like debate, brainstorming) is exactly what you want to see on a team, and why you build diverse teams to begin with. But you want to then be able to converge back into agreement on the big things (ie. where we are headed and what paths we are willing to explore to get there)

• We talk everyday or produce detailed internal reports – not necessarily. Regular communication (both live and async) helps ensure your teams are adjusting expectations and views on where you’re headed, but be careful: detailed reports or regular status meetings do NOT equate to alignment. 

• We share an air-tight plan – no need, but integrity and follow-through go a long way toward helping to keep teams in alignment. If one team is flailing and another is consistent, they’ll naturally fall out of alignment.

• We had one good goals discussion – yeah right. Head-nodding in one goals discussion rarely means true alignment. It’s when the reality of the following Monday comes around (and teams are faced with re-balancing their existing and new commitments) that you get a better sense of where things stand. 

Alignment needs to get checked and re-checked often 

Just like with your car, alignment needs to be checked and rechecked regularly. And if you take speed bumps at 40 mph (like me), you’ll regularly find yourself in situations where alignment is thrown off. 

These can be significant external things like: 

• A competitor preempts your launch and ships something better and cheaper

• Macro conditions cause a swift drop in demand for your flagship product

Or, internal things:

• Team 1 is blocked and needs something from Team 2, but Team 2 is over-capacity

• Team 3 launches something, learns a ton, and wants to explore a new path forward that impacts Teams 1 + 2

• A team member who is critical to a launch leaves and now dates are at risk 

All of the above represent bumps in the road, and call for a check in alignment. 

Alignment matters

As your team starts to scale, your collective impact will depend on your ability to keep your teams working in unison. True alignment across teams can supercharge you towards your goals, and misalignments can grate on a team to a point of burnout. In a startup, where every bet counts and surprises lurk around every corner — it’s critical to check and re-check your alignment.

I’d love to hear from you

How have you found success in getting to (and staying) aligned at your fast-moving company?

Leave a comment

I’ll be digging into all aspects of strategy and operations while scaling here — if that interests you, subscribe!

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Many startup leadership teams feel like this. They have impressive talent and energy but lack mutual understanding and cohesion. This is dangerous when existential risk and distraction are constant threats.

It's crucial for leaders to get on the same page about their focus, purpose, and vision for success. To do that, you have to set in motion a practice to achieve alignment. 

Document and share your founding thesis

If you're a startup, your team is likely guided by each members’ unproven assumptions, supported by signals, instincts, and maybe some first principles. It's common for founders to keep these assumptions in their heads, like a treasure trove of earned insights. 

Writing these down might sound like your worst nightmare. And it has to be done. 

Tap your co-founders on the shoulder, reach out to trusted early advisors, or bring in someone like me to help — just do it.  

And then, invite your team in to scrutinize it. This move, while vulnerable — Ah! the emperor has no clothes! — encourages collective ownership and builds a stronger thesis. 

A well-documented thesis will help your team identify the biggest risks and focus their efforts on the right things. It ensures an intense, shared focus over time, reducing the chances of costly missteps. I know you’re busy with the day-to-day. Set aside specific time to view things from 5,000 to 10,000 feet to gain perspective. 

Start by answering these questions:

• When we founded this company, what opportunity did we see, and why did we believe this company needed to exist?

• What have we learned since then about our customers, our offering, and our opportunity?

• Today, what do we believe is most valuable about what we are building — to both our customers and our company? Be specific.

• What are the 2-3 things we need to absolutely nail in order to create this value? What must be true for us to achieve our goals?

To bring this to life a bit, here's a fictional case study:

There is a five-person founding team (with a number of teams behind them) working feverishly on a prefabricated ADU startup. Everyone will tell you they’re working around the clock, but it’s unclear to what end:

• The Head of Marketing is working on a rebrand exercise

• The Head of Finance is building complex pricing models

• The CTO and Head of BD are working on a partnership to integrate a voice-enabled product owned by a big tech firm

• The CEO is fundraising

Then, on a whim, the team reads this newsletter and decides to step back and land their thesis (below):

Here’s a simple template for building your own.

Some callouts:

• The above view is a speculative thesis. These assumptions are a great starting point for a debate. Check if your team shares the same understanding of the world and the opportunity, and how we arrived here. 

• A thesis is not a “strategy.” It’s a set of assumptions that precede it.

Use your founding thesis to drive focus and execute

Now, with the thesis drafted and agreed upon, you might find yourself curious about the following:

• How important is that big partnership half of our team is working on?

• How complex do we really need our pricing models to be?

• Are we doing enough on the marketing end?

• What is the biggest risk and are there bets we can take today to help mitigate this risk?

You should treat your document as a living, breathing guide and use it often for reference. Here are some other things you can do once you have your document drafted: 

• Update it as your thinking evolves. Your document is not a one-and-done deal. Let it be a hub for new ideas and bold bets. Work on it with your team to drive cohesion. 

• Let this thesis guide your thinking on goals and priorities. 

• Use the document as a tool for onboarding newbies. Distribute a neat, one-page version to everyone in the company. 

The days of easy funding are gone. No more free rides for whitepapers and Power Points. Only teams that can execute will stand out and survive.

Most people think about "execution" as going heads-down and shipping products or closing deals. That’s not enough. You also have to: 

• Stay grounded on a thesis and work as a team to get smarter over time.

• Say no to countless distractions and focus on making the right few bets.

• Bring in and properly utilize new skill sets to expand the team's capabilities over time.

It’s always worth the time and effort to get and keep your leadership team on the same page. It’s key to focus on the problems that will move the needle.

This post was first published on the Awesome People Substack, with editing support from Julia Lipton. Join their awesome crew now!

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