We’ve covered leading a team of experts and setting goals at the right altitude. Now the unglamorous part: actually running the business, day to day. It’s bigger and faster than it used to be, the leaders are excellent, and they need two things that sound contradictory — your guidance and your absence. The way you give them both is a structured meeting cadence.
Without one, you default to the worst version of yourself. You get a nagging feeling about sales, so you drop into a meeting and start grilling people. You hear something about the roadmap and fire off a Slack that sends forty people scrambling. This is pigeon leadership — you swoop in, cause chaos, shit all over everything, and fly off, leaving the mess for someone else. A cadence is what keeps you from doing it. It gives your attention a place to land on a schedule, so you stay connected without stepping on everyone’s toes.
Participant leadership
People talk a lot about “servant leadership.” I prefer what I call participant leadership. You’re the CEO — you’re in charge — but being in charge doesn’t mean controlling everything. It means building a set of meetings where you can show up, get real value from your experts, and keep the business aligned, without turning every appearance into an interrogation.
And remember your time isn’t neutral. When you ask a pointed question, the whole org reorganizes around it overnight. Structured meetings channel that — they aim your influence at the things that actually matter, instead of spraying it wherever your attention happened to land this week.
Here’s the model I run.
Weekly and bi-weekly: cross-functional touchpoints
- Forecast call. My CRO runs it. I’m there to listen and support the deal discussion — not to ask the hard questions or challenge the team live. If something’s off, I take it up with the CRO separately. That keeps the call theirs, and it gets me a raw, unfiltered view of what’s really going on.
- GTM strategy. Small and focused: CRO, CMO, RevOps, CFO. Depending on the topic I’ll pull in someone deeper — head of demand gen, product marketing. Enough people to decide, not so many it turns into a town square.
- Product strategy. Same shape, product side: CPO, CTO, head of design, and whichever PMs or CS leaders the topic actually needs.
- G&A. HR and finance are usually tangled together, so I put the CFO, HR lead, GC, and COO in one room.
- Pipeline. This one’s mine to run — sales and marketing, focused on pipeline generation, blockers, and what’s coming next.
The job across all of these is the same: stay connected, back your leaders, and keep everyone aligned — without coaching the CRO on how to sell. You’re not teaching people their function. You’re making sure they’re pointed at the strategy you set, and pointed at each other.
Monthly: keeping everyone aligned
You don’t need weekly all-hands at scale, let alone daily ones. You set the year’s direction with your V2MOM, and your leaders are running the business. Monthly is the right altitude.
- Managers meeting. Every people-manager in one room. It’s the pre-read for the all-hands and where I handle HR topics — briefing managers on what’s coming and how to lead their teams through it. These are the people who field the questions and hold things steady when something changes, so aligning them on the message first isn’t optional.
- All-hands. I rotate the format across the quarter. Month one: a 90-minute QBR — sales numbers, renewals, launches, the real metrics. Month two: a 60-minute town hall, pure Q&A, questions live or submitted ahead. Month three: a short broadcast — key updates and the big messages I want to land.
Quarterly offsites
The offsites are some of the highest-leverage time on the calendar. Thirty or so people in a room — the exec team plus a rotating cast from the next level down, depending on what we’re tackling. The point is to align and realign on strategy, chew on the big topics, and build the team.
Two days, and the shape barely changes:
- Day one morning: V2MOM review, so we’re sure everyone’s still aligned on where we’re going.
- Day one afternoon and day two: strategic topics, each led by a different leader — retention, a new market, whatever’s live. No breakouts. The value is in the whole group arguing it out together.
A note on 1:1s
Regular 1:1s keep you connected to your team, and skip-levels keep you honest about what’s really happening a layer or two down. Use them to build the relationship, understand what drives someone, hear concerns early, and give direct feedback — criticism or praise, both land harder in private.
But 1:1s are not a venting ground about other people, and they’re not where you solve cross-functional problems. If a fix needs two functions in a room, it doesn’t belong in a one-on-one — it belongs in your strategy meetings, where the right people can actually settle it. Keep the 1:1 for the things that are genuinely between you and that person.
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