Friends,

As this lands in your inbox I’m wrapping up a week in beautiful Queenstown, New Zealand.

It’s been 7+ years since I picked up a snowboard, and this week I did 3 days of fun (but physically punishing) runs down the mountains here. I might have whiplash from have more confidence than skill, but the mountain is always good at putting that in check.

Speaking of whiplash, I feel like I used to get professional whiplash from the constant swing between some deep technical or human issue, to deep strategic issue across the function or business.

(can we all just pause to appreciate that segue?)

So it’s fortunate then that I was able to speak to Adam Weber, who specialises in working with People executives in achieving the altitude necessary to go from deep technical expertise to broad strategic executive.

That and he covers four other areas he says are critical for the successful transition from domain expert to successful executive.

Enjoy this week’s edition ✌️

Matt

In case you’re new here (or just missed it) here’s the past three editions of the FNDN Series:

Before AI, HR wrote requirements while vendors or internal engineering teams built the software.

That era is ending, because HR teams can build now.

Here's what I’m seeing:
→ A 4,000 person company built its own performance review tool, org chart, and internal talent marketplace.

→ A 1,500 person company on Workday priced an LMS, then vibe-coded one themselves instead.

Both had working versions in weeks. Engineers later helped productionise and harden them.

Thinking of vibe-coding yourself? Where to start.


You probably don’t build payroll or a HRIS first 😊 Build the employee experience layer instead. Career frameworks, recognition, pulse checks, 1:1 prep, performance reviews, onboarding, manager coaching.

I've built a few examples you can reference, adapt, or simply use for free.

Interested in sponsoring the FNDN Series?

Know a startup Head of People looking for answers 🙋 why not forward this to them for some instant karma? ✨

This edition is based on the latest episode of the FNDN Series podcast, with Adam Weber.

Adam Weber is an executive coach helping leaders navigate pressure, clarify priorities, and lead with authenticity. A two-time tech founder with 15+ years of C-level experience, he’s the best-selling author of Lead Like a Human and a recognized voice on leadership and culture.

The step up to Chief People Officer comes with an abrupt discovery. The expertise that won you the seat in the executive team meeting isn’t what ensures your success in it.

Adam Weber sees it in almost every people leader he coaches. He co-founded and was Chief People Officer of Emplify (exited to 15Five), wrote Lead Like a Human, and now coaches people executives and entire C-suite teams.

The problem, he says, starts with definition: the CFO's job is clear inside the meeting and out, while nobody defines the CPO's in-room role. And it’s that gap where imposter syndrome grows.

That feeling doesn't fade with seniority. The mastery that got you the seat is comfortable to keep leaning on; the growth, Adam says, is in a different set of muscles. 

He characterises the success he sees in effective executive roles, into five signals. 

This is what they look like and how they show up:

Rise above your function and look at the whole business over a long horizon. Adam's reasoning: "we are all working on the business together, not just our individual functions." This commonly shows up in how you, are you speaking as the head of HR or as an owner of the company?

Say hard things out loud. Challenge another exec's idea, surface the concern the room is dancing around. This shows up as ‘what's the thing everybody is thinking that nobody has said?’

Adam defines this by its absence: everyone has worked for an executive set in their ways while the world changed around them. 

You can check for this by evaluating which people process you’re still running only because it worked at half this size, vs today’s company.

Set ambitious goals, hit them, and carry the weight that's yours. The CEOs Adam coaches complain most about being handed problems without solutions; so step beyond the problem towards a set of solutions the CEO can be involved to edit, instead of just naming problems.

Your contribution to the collective energy of the team. The check for how this shows up is this: are you working on the business alongside your peers, or defending your own kingdom?

Adam sees two profiles show up the most in executive teams. One in the trait that’s most often missing from the executives around you, and another in CPO role itself.

Exec teams, Adam says, come in two varieties: "messy and super messy." The messiest is the executive who's strong on four signals and missing cohesion: Adam's term for this is the asshole executive.

This is the person who hits their numbers and thinks at altitude, meanwhile the room still dreads them. Worse, from Adam’s experience, the damage can often hide behind good manners: "We're all smiling, it seems pleasant, we're basically all just defending our own kingdoms."

The CPO is better placed than anyone to deal with this: no other executive shares the CEO's whole-business view as closely, so you see the behaviours that others might shrug off.

Adam gives clients two ways in. 

At the offsite, Adam has clients run what he calls an elephant conversation: a session with one agenda item, the things this team isn't talking about. His reasoning is that every executive, whatever their role, has sat in the smiling meeting where everyone quietly defends their own kingdom, so putting that shared experience on the table is the CPO's opening to a more transparent dialogue. Done well, it turns the cohesion problem into something the team can work on together, out loud. 

The exec who's poisoning the room gets discussed as a dynamic the whole team owns, which is a conversation people can survive.

Adam's favourite example is a CPO he coaches who treats truth-telling as part of her job description: she names the dynamics she's seeing one-on-one and says the hard things the rest of the team won't, with an explicit "I've got your back" attached. His view is that the CEO's seat is lonely for a specific reason: there's a general sense that nobody is being fully honest, and often the CEO's own reactions have trained the team to steer around the landmine topics. A CPO who breaks that pattern makes the loneliest seat in the company less lonely, and earns a collaborator for the messier problems ahead.

But there’s a trap to watch for: when one executive is poisoning the room, your instinct is to take the repair work on personally, coaching them on the side and smoothing things over after every meeting. 

Keep that up and you've slid out of your exec seat and become the in-house therapist.

Adam's rule is to protect the seat: bring a high-calibre facilitator in from outside so you can sit in the offsite as an executive like everyone else. You can lead the team in candour without becoming its counsellor.

Adam coaches every seat in the C-suite, and he says the Chief People Officer is reliably the nicest person on the team. He doesn't entirely mean it as a compliment.

At the exec level, over-softening reads as a lack of conviction. The pattern he sees on repeat is this: a CPO spots a real problem in the culture, knows how to fix it, pitches it to the exec team, softens the delivery, and then promptly watches it die.

The best people leaders say the quiet thing everybody else is thinking and put it on the table. And that instinct can be trained: Adam runs CPOs through the same preparation before any contentious meeting. 

It’s something you can easily adopt before your next one.

There's one more piece of preparation Adam gives people leaders specifically, because no other executive gets a call about a workplace tragedy or an HR violation, hangs up, and walks straight into a meeting that needs 30,000-foot thinking. The whiplash between those two heights is built into the role.

So Adam has clients build a ritual for that pivot, however small: before you walk into the room or join the Zoom, take a deep breath and say the word "altitude" to yourself, to remind yourself of the mindset you’re bringing to that meeting. 

Both actions do real work.

The breath is doing real work: a full inhale, then a slow exhale settles stress faster than mindfulness meditation. The word is simpler still, a one-word reminder of the perspective you're choosing at the exact moment the role is pulling you back into the weeds.

The self-talk hails from sports psychology, where athletes use a short cue word to call up the state a task demands. 

Together they're a ten-second reset, made at the exact moment the role is pulling you back into the weeds.

Adam leans on a line from Shake Shack founder Danny Meyer: "business is problems." They don't run out; the exec room is where they land.

Leadership, Adam says, is mostly a discipline, and the five signals are its shape. The colleague missing that cohesion is the hardest profile to sit beside; the people leader missing candour is the easiest one to become.

A call to action I was left with from this conversation is this: which signal is your strength, and what are you doing to keep it there? And then which one trails furthest behind it?

Bringing the second up to the level of the first is the development plan, and Adam's prep above is where it starts. Then test yourself, because self-scores lie: ask your CEO or your most trusted exec peer which two they'd have picked for you.

If you enjoyed this post or know someone who may find it useful, please share it with them and encourage them to subscribe.

A roundup of the most interesting stuff from the week:

When you’re ready, here’s three ways I can help you:

1. Tools & resources
Resources and tools that give you what you need to build your own startup compensation practices.

2. Comp consulting
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3. Startup People Summit
A 1-day annual event for People professionals in scaling companies. Creating the playbook for startup people practices. Grab recordings from past events, or subscribe to join the next summit.