I've run over 60 quarterly planning sessions in the last two years - across my portfolio companies, leadership teams I advise, and our own internal operations. I've seen them go exceptionally well. I've seen them fall apart by 10am. And I've noticed the same patterns repeat often enough that I'd call them rules at this point.
A couple of years ago, I was running one of these sessions for a portfolio company. We had an outside advisor sitting in - someone with roughly 30 years of business experience across multiple companies and industries. The kind of person who's been in more conference rooms than most of us have had jobs.
About two hours in, he pulled me aside. He told me he'd never seen a team run a meeting like this. He asked if he could steal the format for the other companies he advises.
I've thought about that moment a lot since. Not because it was a compliment - but because of what it said about the norm. A team of people in their 20s and 30s, working through hard conversations together, aligned on where the business was going and why - and a 30-year veteran had never seen it. That's not a good sign for the average leadership team.
What made that room work wasn't the agenda. It was that they'd been paying down their debts.
Every business accumulates three kinds of debt over the course of a quarter. Almost none of them track it.
Conversation debt. The hard conversations that don't happen because the quarter feels too busy. A performance issue that gets ignored. A tension between two leaders that everyone agrees to step around. A client relationship that's fraying but no one wants to own. You tell yourself you'll address it when things slow down. They don't. Ninety days pass, and the balance is higher than when you started. These conversations don't disappear - they just get more expensive the longer you wait.
Strategy debt. This one builds when you're executing without stopping to ask whether what you're executing still makes sense. Your products, your services, your pricing, your customer - all of it deserves a room and a hard conversation at least once a quarter. Are we solving the right problem? Is what we're selling still what the market needs? Most teams never ask these questions during a normal week because the week is already full. So decisions that should take 60 minutes of focused conversation get deferred indefinitely, and the business drifts in the direction of inertia rather than intention.
Direction debt. This is the quietest one - and usually the most expensive. It accumulates when the team stops talking about why the business exists at all. Not the what, not the how - the why. Mission, values, what you're actually building and for whom. These things don't feel urgent on a Tuesday afternoon when there's a client deliverable due. So they don't come up. And over time, without anyone deciding it, the business stops being a mission-driven organization and starts being a task machine. People clock in, cross things off, clock out. Not because they don't care - but because no one's reminded them what they're working toward. Direction debt is what turns a company with real purpose into a company that simply exists.
Eight hours a quarter is how you pay it down.
Not a weekly standup. Not a Slack message. Eight hours, in a room together, phones away, with the right questions on the table. That's the only mechanism I've found that reliably clears the balance across all three.
The teams that do this well don't come in to vent. They come in to battle-plan. They handle the small stuff during the week and save the quarterly for the conversations that actually move the business. The teams that struggle treat it like a grievance session - everyone arrives with a list of qualms and the meeting becomes a negotiation instead of a strategy session.
The difference, almost every time, comes back to whether the founder has walked in with a clear picture of what the next 90 days need to produce - and whether the team trusts that vision enough to build around it.
Hope is not a strategy. Neither is a busy quarter.
Working Theory: Run The Session
If you're not running quarterly plannings, start. If you are but they feel flat, the issue is usually one of two things: the wrong conversations are taking priority, or the rocks you're setting aren't actually connected to the founder's vision. Or worse, they’re performative.
Rocks are worth calling out specifically. Most teams set rocks that feel interesting or manageable - not rocks that actually move the business forward. The only way to close that gap is to start with where the founder wants the company to be in 90 days and work backwards. If that anchor isn't in the room, the rocks are just a to-do list with a fancier name.
We put together a full guide on how we structure these sessions - the agenda, the prep work, the IDS framework, and how to set rocks that matter. It's the same format that earned that advisor's request two years ago.
Extra Ask…
I gave a chapel talk at Wabash College recently, titled "Why You Should Hate Wabash, At Least Once." The talk covers a lot of the same territory this newsletter does - what real challenge builds in you, and why avoiding discomfort is a losing strategy. If you have a connection to the college, give it a watch. If you don't, swap "Wabash" for anything hard in your own life and I think it still lands. I skip the intros and get into it a few minutes in if you want to jump ahead.
