🚩 What Exec Departures Tell You That The All-Hands Won’t 🚩

Author's note: Thanks for reading! I’ve been spending more time reflecting on how employees can spot (or build themselves) operationally- and culturally-healthy growth businesses, specifically through the lens of a CFO/COO. If these posts are helpful, I’d love to hear from you. And if there’s a topic you’d like me to weigh in on, feel free to shoot me a message.

Side note: BetterComp is hiring! Link at the bottom.

I’m geared towards working at companies where the mission feels alive. When you can feel the momentum in the hallway (or in the remote world, the slack channels). Where people actually believe in what they are building and are jazzed about the mission. I’ve also worked in the other kind, where the energy is off, the ones that still occasionally hold an All-Hands, still post the job openings, still say “the team is strong” even as the room gets quieter… and the space just feels more empty.  

Here’s some things I’ve learned along the way. 

When a Company Shifts from Building to Protecting

There’s a moment in every company where the energy just shifts. One day, it’s product reviews, pipeline calls, user interviews, and stretch hires. The next, it’s internal reshuffling, fewer metrics updates, narrower messaging, and less eye contact from the exec team.

You usually feel it before you can name it. While I’m a builder at heart, I’ve been a part of those shifts. It wasn’t fun.

Here’s what that shift looks like from an operator’s perspective:

• Headcount reorgs that don’t line up with any real strategy. Sometimes it’s about quiet cost cutting, sometimes it’s because the functional leader knows the existing org isn’t working so they shuffle the deck to see if something shakes loose. 
• Budget reductions in GTM and R&D. The roadmaps go quiet as the key subject matter experts leave and aren’t backfilled. Innovation stalls, but management still expects those price increases come renewal.
• Targets aren’t believable or achievable. Individuals are scapegoated for missing said targets. Departures get recast as “realignments.”
• Legal strategy becomes the growth strategy. While budgets get cut elsewhere, legal spend ticks up as the company increases their litigation efforts externally. 
• Risk mitigation replaces ambition.The loudest voices in the room start talking more about risk than opportunity

When you see red flags like this, just know the company is no longer building. They’re protecting. And protecting isn’t the same as leading.

Spin vs. Reality: Learn to Read the Pattern

Most employees aren’t going to be able to see the full picture of a business, but you can focus on employee turnover as a good proxy. 

Most companies are great at onboarding, but very few are honest about departures. Whether you’re assessing a new job or evaluating your current role, if you want to know what’s really going on inside a business, look at who’s walking out the door, and how leadership acts afterwards.

 A single departure means nothing. But the pattern does. You’ll hear things like: 

• “We’re evolving the org.” (what is this, Pokemon?)
• “This is part of a broader refocus.” (this is like saying “we sent the family dog to the live at the farm because he got too old”)
• “It was a mutual decision.” (Narrator: it wasn’t)

Here’s what you should be asking yourself:

• Why was this person written out of the story so fast?
• Are the departures stacking up in a specific team or is it pretty widespread?
• How are the departures talked about after they leave? How quickly do they become the scapegoat? 
• Why are you getting vague explanations about the people who helped build the company?

If the story doesn’t match the pattern, it’s not a communication problem. It’s a credibility problem.

CFOs Don’t Leave for Nothing

Pay particular attention to executive turnover. Those can tell you a ton about a company’s cultural and strategic health. I won’t scapegoat it, executive positions are high risk, high reward. They're also high stress, especially in a startup or growth stage. So when a key exec leaves, it’s rarely random.

I know I’m biased here, but let me be clear: CFOs don’t quit easily. We have an almost unhealthy level of tolerance for heavy workloads (that most consider boring). We’re embedded in every operational discussion. We know what’s being said in the boardroom and what’s being quietly edited out of the narrative. We have a deeper understanding of the leading indicators than even the CEO. We also know where all the bodies are buried.

The CFO is typically not a founder and they have different incentives in a business than the founding team. So when a CFO walks, it can often mean one of the following:

• Disagreement or misalignment on business strategy with the CEO
• Concern about cash runway, viability of the business, or likelihood/value of the eventual exit.
• Discomfort signing off on board-level decisions
• Loss of trust in the actual trajectory (not the public one)

These can all be boiled down to just one reason: if they don't think they're going to make any money on an exit, they won't stick around for long.

But what about other exec departures? But here’s some other leaders you should be looking at: 

• When a CHRO leaves, it can be a reflection of what’s happening under the surface of the culture.
• When a CRO leaves, it usually means the growth story is shaky.
• When a CPO leaves, it often means the product is no longer aligned with the company’s growth strategy. Or worse, that there is no strategy anymore.

In my role, I have access to both the strategic plan and the backchannel conversations. I’ve seen execs leave for many reasons, and a lot of the time, if they leave on their own they leave because they couldn’t stay aligned with what was coming next.

If leadership isn’t willing to explain executive exits, or worse, rewrites the story entirely, it tells you everything you need to know about what your experience will be working there.

Good leaders stick around when there’s something to fight for. But when the builders leave, and the story changes the moment they’re gone, you know something’s broken.

Culture Is What Happens After You Leave

Everyone loves to talk about company culture. But if you want to understand a company’s true character, look at how it treats people after they walk out the door.

• Do they acknowledge the contribution?
• Do they celebrate what was built?
• Do they stay in touch, speak with respect, stay proud of the time they shared?
• Or do they minimize, erase, pivot, and pretend?

It’s not just about retention, it’s about respecting the contributions of those who came before.

The Two Things That Always Matter

One of my main jobs as a CFO is to take the complex and simplify to make decisions. I try to do that everywhere. 

And at the end of the day, I think building a great company comes down to two things:

1. Build a great product.
2. Hire great people and get out of their way.

That’s it. The rest is noise. 

When a company starts doing neither, and starts blaming the people who left instead of reflecting on what’s changed, they’re not building anymore. They’re managing its decline.

If You’re Deciding Whether to Stay or Join

If you’re deciding whether to re-up for another tour of duty…

If you’re evaluating whether to join a new team… (side note: Bettercomp is hiring!)

Don’t just ask what they’re building.

Ask who’s still building it.

And see how they talk about the ones who aren’t.

You’ll know more from that than any mission statement they offer.