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

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!

Know someone who would enjoy this newsletter?

Share Thinking in Quarters

I’m not talking about the one-off stuff — like those of us afflicted with never-ending illness in our households, or the other calamities we’ve all faced for the past few years.

I’m referring to the “I’ll set up time with you” person who never does. The, “sure, I’ll send that over by end of week“ line followed by crickets.

I've found that people who regularly break commitments fall into one of four camps — and this applies to all levels of seniority in an organization.

The first two are fairly straightforward and typically improve with skills development (training), as long as you can get your finger on where the challenge is.

These types include …

Type 1: Poor Systems

They struggle with time management, and tracking of commitments. It’s a genuine “yes,” but poorly supported.

Type 2: Task x Skill Mismatch

They may not have the skills required to do the job in the timeframe needed. This is tricky to navigate – because sometimes, there are real and perceived repercussions (loss of credibility, reassignment, loss of role) if uncovered. Overconfidence makes this worse.

The next two get a bit more nuanced, and typically require feedback and coaching.

Type 3:  Operate on Default

They are issuing a “sure” that should be a “no” out of a belief that other people won’t notice or care when they don’t come through. This bad habit of defaulting to “yes” is really an issue of integrity and becomes a self–fulfilling prophecy.

Type 4: Not Onboard

They are pushing back. These are veiled “no’s” – ie. commitments with no real intent behind them out of a belief that saying “no” is not worth the discomfort. In this case, the person is not onboard with some part of the ask, and instead of saying so, they issue a “sure” and do nothing.

Note: the desire to please pours fuel on all four fires ( 👋 People Pleasers).

In order to dig out of the missed commitment trap, it’s really helpful to know what’s behind it. Here’s how I might approach a conversation, always in a 1:1 setting.

For direct reports:

For peers:

One thing that will help these conversations go well is a strong overall relationship to begin with. I’ve written here about the three things to focus on when building those.

Here’s a quick story to illustrate how things aren’t always what they seem with peers:

I once rolled out a new planning process across a very senior group of leaders. After a good initial discussion, I started getting some engagement from all leaders except for one. My initial assumption was that he was pushing back on the process, so we sat down and I went into full persuasion mode on why the process would help for specific problems he had. 

It wasn’t until a few one-on-ones later that I realized that it was actually a skills gap. He was very seasoned, but was in a very specialized senior role. The process of budgeting and strategic planning was actually new to him, and not something he was comfortable jumping into without some support. 

Once I realized this, I was able to lean in and work directly with him as a thought partner, instead of as a taskmaster. It shifted the dynamic of our relationship too, and became a really productive partnership.

Special note on your Type 1 Commitment Missers (Poor Systems):

• If the person is your direct report, the best option is training (especially versus micromanagement): My first manager at PayPal had me take “7 Habits of Highly Effective People” and “Getting Things Done” — look into any available stipends at your company and strongly suggest they make the investment. 

• If the person is your peer, and I’m saying this to the former project/program managers in the audience: try to contain yourselves. It’s very easy to slip into project management mode in service of others. This is a slippery slope that blurs accountability. Stick to the above structure, suggest training (or an admin), and keep moving. 

Here are some general tips on how to navigate these conversations:

• Consider this a discovery conversation, not an interrogation. Seek to understand before assuming they are acting out of disrespect for others or their time.

• Watch body language closely and look for signals that you may be hitting on something (arms crossed, leaning back – not it; leaning in, shifting in chair – you’re probably close.) 

• Practice active listening (play-back to ensure you’ve heard correctly) and be grateful for any candor – giving and receiving feedback respectfully is an act of trust. Treat it that way.

• No need to solve all problems in a single discussion. Feel free to acknowledge and sit with feedback before coming back with a response.

• Demonstrate that you respect and value their word by holding them accountable to it (key for your Type 3s!) — this doesn’t mean checking in constantly, or unnecessarily escalating. It means that if they miss going forward, you’ll: 1) notice, and 2) make the adjustments needed to keep the effort on-track.

When someone continues to miss commitments, it’s easy to jump to the wrong conclusion, get frustrated and frankly, want to give up. I’ve found that it’s sometimes possible to dig in, get to the heart of what is happening, and why – and then work your way out of it. 

What is your experience with any of these four Types?

I would love to hear any examples of how you all have worked through missed commitments, and anything above that I may have missed!

Leave a comment

Got an embarrassing question?

Your responses to my recent “advice column” prompt (answers coming soon!) got me thinking: What is your strategy, ops or leadership-related question that you’d only ask your most trusted mentor?

Respond here and send it over. I’ll publish with a response — all anonymous.

That conflict of priorities? It’s on you to resolve.

That big idea you have? Rarely something you and your teams can execute alone.

That complaint about how we’re working? Good luck fixing it with just ideas.

Gone are the days of brilliantly working from your own page, or kicking conflict upward when things fall out of alignment.

So it’s probably no surprise that 80% of what I work on (as a coach to startup execs) centers on working effectively with peers. I’ve found that there are a few things that really matter, especially in the early days of a peer relationship, so I thought I’d summarize here.

Three things to focus on when building peer relationships

Thing 1: Work on Something Together

Nothing helps you figure out how to work with someone like… working with someone. Don’t wait for that business-critical priority to pop up. Create some space to wander into a problem together, and test-run your working dynamic on something low-stakes. 

Some tips:

• Pick something that you can learn together – or a problem you can join forces on solving quickly. Choose something that takes about 2 weeks, end-to-end, to prevent burnout and increase the chance of completion. Nothing overly complex. 

• Create space for divergence and convergence. Don’t just rush into execution mode – take some time to explore the bounds of what you each know about the opportunity, problem and possible solutions. Try establishing some common ground, kick off a few debates, brainstorm a bit, talk to others and reconvene.

• Pick something that is in the white space (not obviously one person’s job) or help your chosen partner with something important on their plate that you are confident you can add value to with little friction.

The Why:

• Get to understand how one another thinks – What do they value? How do they approach problems? How do they communicate? What cool ideas do they have? 

• Build trust – this is less about proving what you know, and more about showing that you can be a trusted partner. Make and keep commitments to demonstrate accountability.  Express yourself freely but show that you’re open to feedback. 

Thing 2: Get to Know One Another 

Amidst the day-to-day demands of working together, try to spend some time getting to know one another as humans. Find out about hobbies, kids’ names, favorite band. Take notes so that you actually remember! This is not meant to be a surface-level box-checking exercise – it’s an opportunity to really understand more about them, and authentically connect. 

Some tips:

• Make a long-term investment: Some of my closest professional contacts are peers from former leadership teams. Because we really invested in the relationship, our friendships persist beyond roles or companies. 

• Tack social rituals on to work things: add the dinner after the offsite, or the coffee before the meeting. Do the quarterly happy hour reunion to get the gang back together. It’s worth it!

• Create space for non-work banter: on one of my favorite leadership teams, we’d consume ourselves with travel, grilling and photography just as much as payments, commerce and crypto. Most of this was on Slack and made for a nice break in the day.

Note: This is not a replacement for Thing 1 above – and this cannot be rushed. I think we’ve all been in the situation where rapport-building happens, but trust never forms. I’d attribute this to skipping #1 above, or flubbing it.

The Why:

• Build empathy – The goal here is not to force friendships with every single one of your peers. That would be artificial and exhausting. One ideal outcome you’re hoping for is empathy: understanding of where that other person is coming from, and a bit more about what makes them tick. 

• Connection – One of my favorite things about being on a team is the shared experience of it: the highs, the lows, the mundane. I’ve found that connection can be cultivated on work-related or non-work related topics – and sometimes there’s crossover in either direction. For example, with one peer, our connection as hip hop lovers helped us break the ice when we were at odds in a debate. With another, our connection as mothers to young children helped us relate to one another during a particularly challenging period.

Thing 3: Have Regular 1:1s

I think of 1:1s as a way to maintain relationships vs build them. With some foundation in place, a 1:1 can be a great forum for checking on and correcting misalignment, resolving conflict, and building understanding.

When there’s a strong interdependence between the functions/teams that I manage, and theirs, I prefer a weekly cadence of 1:1s. When it’s less strong, but we’re on a leadership team together, I prefer bi-weekly (or monthly). In all cases, the frequency can adapt to the need. 

Here are my typical focus areas for 1:1s with peers, shown across a spectrum of trust (low-trust conversations require little trust to go well, high-trust requires high trust to go well):

The Why:

• Exchange insight – there’s typically a difference between what you believe happened on a project, and what really happened. This delta tends to be more about interpersonal dynamics, some of which are helpful to understand for the next go-around. With enough trust in place, you can learn more about what’s really happening – both in and around your organization.

• Resolve Conflict – when alignment is tested, support is needed, or internal handshakes need to be adapted between two teams, this is typically where it happens. The safety of a 1:1 meeting (and the removal of distraction and other personal dynamics) allows for a higher likelihood that you can both get to the heart of what’s needed, and solve it. 

Some tips:

• Try to group these – I like to do my 1:1s with direct reports on Tuesday afternoons, and with those as input, I head into 1:1s with peers on Thursdays. 

• If I plan to present something at our exec staff meeting, I make sure to bring it into a few of my 1:1 meetings with peers the week prior. This preview allows for helpful feedback, questions and importantly, a heads-up (especially critical if there are any areas where I’m depending on the support of others for something to happen). This ultimately strengthens the proposal and increases chances of follow-on impact.

• When I start a new 1:1 series, I set the “repeat” duration for 3 months, max. That way, we can naturally re-evaluate the frequency after some time, and prevent the sync from becoming an obligation on either end.

Quick note: An anti-pattern that I typically see with first-time ops people or newer execs is the over-scheduling of 1:1s. This tends to be in service of making sure they stay on top of everything. Aside from over-running your calendar and eating into work time, this tends to lead to burnout. Find other ways to get information (ie. what’s happening, when, how’s it going) – and instead, rely on 1:1s for real insight and alignment. 

Why this matters

A foundation of mutual respect and understanding is key in working well together. On any leadership team, you’re bound to face tricky, and sometimes excruciatingly painful times — and its in those moments that you’ll be thankful that you invested in your peer relationships.

Question for you:

How do you go about building strong relationships with peers on your leadership team? I’d love to hear from you!

Leave a comment