Friends,

I’m coming back from Sydney where I’ve been the past few days at the amazing Generate summit for B2B marketers.

Lots of people asked my why I would go to something like that, and the answer is that, increasingly, the time I spend on my brands FNDN, Startup People Summit, and this FNDN Series is spent doing marketing.

And while the conference was helpful for those things, what it ended up helping me realise is how similar the job of marketers and people professionals are to each other.

For marketing it’s brand, for People professionals it’s culture, and they’re both trying to do the same thing. They’re trying to create trust, an attachment, and an emotion to a company that ultimately solicits action (whether it’s buying something or working on something).

For many of us, our leader is one of the primary interfaces through which organisational culture is built. And in this edition, we uncover the 5 kinds of conversations leaders can have, to help build it effectively.

Enjoy this week’s edition ✌️

Matt

A roundup of the most interesting stuff from the week:

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This piece is based on one of the many insightful sessions that took place at Startup People Summit last year.

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Most managers in startups got the job because they were good at a different job.

Then we hand them a team, leave them their IC workload, and act surprised when their people leave citing "my manager" in the exit interview.

Damon Klotz has spent a decade watching this play out. 

He joined Culture Amp pre-Series A as one of its founding team members and stayed 10 years while it grew past 1,000 employees, building the Culture First podcast into the top 1% most downloaded in the world along the way.

His argument: the gap between managers and their people is mostly made of unknowns, and five conversations can close most of it.

Damon's starting point is surface area.

When he landed his first HR role at 19, everyone told him he was lucky, and he was. He'd also been increasing his surface area for luck: HR meetups, blogging, early Twitter, connecting with anyone who'd talk to him.

Startups have the reverse problem, a surface area you want to shrink. Unknown market conditions, unknown org design, unknown impact of every go-to-market bet, and above all, unknowns between managers and employees.

A manager can't do much about the market. The unknowns between people are removable, and good conversation is the tool.

Damon leans on Rachel Botsman's definition of trust here: "a confident relationship with the unknown." A team with trust can sit with open questions and still back its collective ability to work them out.

In most startups, people management is the only promotion path, so people take the job for the pay rise rather than the craft.

Then comes the gap: told to run a team, still expected to ship code or close tickets as an IC. Gallup's research backs this up: 97% of managers still carry individual contributor work alongside leading their team.

Teams are getting bigger too.

Gallup has the average span of control growing from 8.2 direct reports in 2013 to 12.1 in 2025, well past Jeff Bezos' famous two-pizza rule (if two pizzas can't feed the team, the team is too big). Damon's read: past eight people, a team becomes a magnet for ambiguity and dysfunction.

The same research is blunt about what works. Employees who get weekly meaningful feedback are engaged at nearly triple the rate of those who don't, roughly 68% against 22%. Most managers get no training in how to have those conversations.

Timely conversations are the cheapest performance lever your managers aren't using.

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

Damon's caveat up front: templates and software for weekly one-on-ones already exist, and these five don't replace them. Each is a moment-in-time conversation, used when the moment arrives, that builds what he calls relational intelligence between a manager and each person on their team.

1. The unpack. For new starters. Author Minda Harts writes about unpacking your suitcase at the door of a new workplace rather than carrying old workplace trauma through it, and Esther Perel makes a similar point: we bring a personal and professional CV to every job. The question: "What did past managers do that made things easier or harder for you?" People rarely volunteer this in an interview, they're too busy impressing you. Build it into the first fortnight of onboarding.

2. The feedback preferences. Ask each person how they want feedback: in the moment or saved for a one-on-one, written or spoken, in front of the group or in private. Damon ties this to Priya Parker's rule that the first 10% of any gathering shapes everything that follows. Get the feedback relationship right early and you never have to renovate it under pressure.

3. The clarifying success. Sarah Walsh, head of women's football in Australia, told Damon that for years the Matildas' bodies "were treated like tiny men": generic sports science, economy flights between games, no laundry stipend, players washing training kit in hotel sinks. Elite athletes, denied the conditions for high performance. So ask: "What does great work look like for you in this role?" and "Do you have the right tools and resources to perform at the highest level?" Unspoken expectations are resentments waiting to happen.

4. The why are we here. From Damon's interview with Simon Sinek: when someone says they want a promotion, ask "to what end?" Then ask it again. The first answer is usually money or recognition. Ask again and you get to things like growing up with money scarcity and wanting the next generation never to feel it. And some people want work to end when work ends. That's worth knowing, and worth respecting.

5. The healthy conflict. Patrick Lencioni calls a team with no disagreement "artificial harmony": everyone nods, nobody changes anything. Damon's bigger worry is ambivalence, where people stop caring enough to push back at all. "Any questions?" No. "Feedback?" All good. A team that cares enough to be disengaged can still be won back; a team that's gone quiet is much harder. Amy Gallo's book Getting Along is his recommended playbook for making conflict safe to have.

Your managers can't shrink the market's unknowns. The unknowns between them and their people are a different story, and five conversations is a small price for removing them.

Pick one conversation and brief your managers on it this month. Ask them in four weeks what they learned about their people that they didn't know before.

If you want the full thinking, start with Damon's Culture First podcast. His own pick for a first episode is the Priya Parker one.

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

1. Tools & resources
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