The Three Things Most Owners Wait Too Long to Fix
Most owners can list the things slowing their company down. Three keep showing up: a leadership team that's been left alone too long, a set of financials that arrives too late to act on, and a meeting rhythm that never quite became a rhythm. The companies that move forward make those three moves. The ones that don't, don't.
Owners want to grow the company. They forget that means growing the people who will grow it with them.
The Three Things That Keep Showing Up on the Whiteboard
After more than twenty years of sitting in leadership rooms with owners, I've stopped being surprised by how often the same three things show up on the whiteboard. Different companies, different industries, different sizes. Same three things.
A leadership team that doesn't function the way it needs to. A set of financials that tells the owner what already happened but doesn't help them change anything before the next thing happens. And a meeting rhythm that's either nonexistent or so loose it might as well be.
They're the moves I see owners delay the longest. They're also the moves that have the biggest payoff when they finally get made.
The Leadership Team Question Nobody Wants to Ask
Most owners can list the people on their leadership team. Far fewer can answer the next question, which is the one Jim Collins built a whole chapter around in Good to Great. Why is this person on the leadership team? What value are they adding? Are they in the right seat?
That question gets avoided because the answer often means a hard conversation. The bookkeeper who was perfect five years ago is not the controller you need today. The sales manager who built the company in the early years is now the gravitational pull keeping the room from moving forward. Every other meeting circles back to why we can't do something instead of how we will.
I used to think the answer was simpler than it is. I'd sit across from an owner, see the obvious problem, and assume we'd just have to deal with it. The longer I do this, the less naive I am about that. You can't move a 25-year employee out of a leadership room the way you'd close a vendor account. The right answer isn't to ignore the problem and it isn't to push someone out without honoring them. Both fail the company and both fail the person.
So the first conversation we have with the owner isn't about firing anyone. We ask one question: what does finishing well look like for this person? Sometimes the answer is a six-month off-ramp. Sometimes six years. Sometimes it's a different role where their experience is an asset instead of a brake. What it can't be is the status quo, because the status quo is what brought us in.
Veterans and the Next Group Have to Work Together
The other side of leadership development is the gap between the people who built the company and the people who are going to take it forward. Not always an age gap. Sometimes it's a tenure gap, somebody who's been in the room for twenty years and somebody who's been in it for two.
Both groups want the same thing and both groups misread each other. The newer leaders assume the veterans will shoot their ideas down, so they stop bringing them. The veterans feel pushed out by people who haven't earned the right to push, so they dig in. Nobody talks. The room stops producing.
The way through is a project. Pick something the newer leader cares about: a software rollout, a process change, or a new measurement, and have them go to the veteran with a specific posture. I want to do this. I think it's going to help us. I can't do it without your influence and your experience. I'd like to ride shotgun on this so I can learn how to drive it next time. Watch what happens to the veteran when someone humble walks in with that ask. Their posture changes. Three weeks later those two are sitting next to each other in the leadership meeting, cracking jokes, disrupting the agenda because they're having too much fun. Four weeks earlier, they were on opposite sides of the room talking about their own departments and nothing else.
Camaraderie doesn't happen by accident. Knowledge transfer doesn't either. Both have to be planned, even when the plan is just lunch.
Financials Tell You What Happened. A Scorecard Tells You What's Happening.
Here is the problem with running a business off financial statements. It's May. You'll get April's financials about halfway through this month. You'll look at them, decide something needs to change, and put that change in motion. By the time the change takes effect, it's June. You just spent two months reacting to a problem you could have caught in week two of April.
A scorecard fixes that. Three to five leading indicators, tracked weekly, that tell you where the business is heading before the financials confirm it. Not a dashboard with fifty things on it. A scoreboard. Nobody watches a football game on a scoreboard with fifty things. They watch a couple of numbers that tell them whether they're winning or losing in time to do something about it.
The leading indicators depend on the business. For a company with a normal sales cycle, leads and conversion rate get you most of the way there. For a custom home builder on a four-year project timeline, sales is too lagging to be useful, but cost is the input to revenue. So we built a weekly bar chart of production costs: red for below break-even, yellow for above break-even but below goal, green for hitting goal. Now the team is looking at a leading indicator they can adjust against, every week.
Building the right indicators takes thought work, and most people don't like thought work. That's why so few companies have a real scorecard. It also takes pruning. The first version is always too long. Fourteen things on the whiteboard, four of which matter. The job is to figure out which four and let the others go. The scorecard is a living thing. What you measured three years ago is probably not what you should be measuring now.
Fifty-Two Versus Twelve
A leadership team that meets once a month gets twelve chances a year to adjust. A team that meets every week gets fifty-two. That's not a small difference. That's the entire game.
The pushback when we introduce a weekly rhythm is always the same. Another meeting. Don't we have enough meetings? Then we ask about the current meetings. Usually, they're an hour of everyone going around the room sharing what they're working on, information that could have been a Slack message. The first ten minutes of the new weekly meeting are for the status update. The other fifty are the issues discussion. What's not working. What needs to be decided. What's actionable? Who's going to do something about it before next week?
If nobody leaves a meeting with a to-do, the meeting didn't need to happen. That sounds harsh until you sit through a few where the same issue gets talked to death week after week and nothing moves.
Weekly is the engine. Quarterly is where you set priorities. Annually is where you step back and ask whether the focus from the past two or three years is still the right focus or whether it's time for something new. Each cadence has a job. The weekly one is the one most companies skip, and it's the one that compounds.
Accountability Starts at the Top, Or Not at All
Almost every CEO I sit down with tells me they want a culture of accountability. They mean it. They want people raising their hands, owning their commitments, doing what they said they'd do by when they said they'd do it. The follow-up question I always ask is what they're willing to be held accountable to themselves. And whether they're willing for the people whose paychecks they sign to hold them accountable to it.
Picture an owner with a forty-foot fishing boat in the driveway. Tuesday morning, the seas are flat, the wind is down, it's a perfect day. There's a leadership team meeting on the calendar. Is that owner willing for one of their team members to say, “hey, we had a meeting today and you bailed to go fishing, what's that about?” If the answer is no, the culture of accountability isn't going to happen. Not because the team doesn't want it. Because the leader hasn't decided they want it for themselves first.
John Maxwell's leadership lid principle says your team will only reach the level of leadership you're capable of. Jocko Willink puts the same idea more bluntly: there are no bad teams, only bad leaders. Different vocabulary, same point. The horsepower in your leadership room is there. The question is whether you're willing to be the one who unlocks it, including the parts of it that will hold you accountable too.
If you are, the rest is work, but it's work that pays. The owners I've watched make these three moves don't just grow their companies. They fall back in love with the work.
None of this is complicated. It is, however, work. And you don't have to figure this out alone.
The Leadership Guide that goes with this piece walks through the key concepts and a worksheet step by step. Keep growing with purpose
Key Takeaways
Three moves show up over and over: leadership development, a real scorecard, and a planning and execution rhythm.
Honoring a long-tenured employee and removing them from a leadership room are not opposites. The question is what finishing well looks like for them.
Financials tell you what already happened. A scorecard with three to five weekly indicators tells you what's happening in time to do something about it.
Fifty-two chances a year to adjust beats twelve. The weekly meeting is the one most companies skip and the one that compounds.
Accountability starts with the owner. The team will only reach the level of leadership the owner is capable of.
Frequently Asked Questions
How do I know if someone is in the wrong seat on my leadership team?
The clearest signal is meeting dynamics. If most conversations route around one person, or one person is the consistent reason a decision gets reversed or delayed, that's a seat problem. Tenure and loyalty are not seat-fit answers. They're the reason the conversation feels hard, not the reason to avoid it. The right next step is to ask what finishing well looks like for that person, not to plan a removal.
What's the difference between a KPI and a financial metric?
A financial metric tells you what already happened, like last month's revenue or last quarter's margin. A KPI is a leading indicator that predicts the financial result before it shows up. Leads and conversion rate predict sales. Weekly production costs predict revenue for a cost-plus builder. The right KPIs let you adjust during the period instead of after it.
How many things should be on a scorecard?
Three to five. Five is the ceiling, not the target. If your scorecard has fourteen things on it, the first job is pruning, not adding. Start with the indicators that the leadership team has the most influence over and that move soonest in response to a decision. Everything else can live on a deeper dashboard the operators look at.
Our weekly meetings feel like a waste of time. How do we fix that?
Three changes. Cap the status update at the first ten minutes; that part can usually be a written check-in. Spend the rest on an issues discussion that ends with named to-dos and deadlines, not talking in circles. And measure success by what changes between this week and next week, not by how the conversation felt in the room.
How do I get my long-tenured employees and my newer leaders working together?
Put them on a project together where the newer leader explicitly needs the veteran's influence and institutional knowledge. The posture matters: the newer leader asks the veteran to drive and rides shotgun, with the understanding that they want to learn how to drive it themselves next time. The dynamic shifts when both people see they need each other for the project to succeed, instead of competing for who's in charge of the room.
References and Downloadable Resources
Jim Collins: Good to Great
Referenced for the chapter on getting the right people on the bus and in the right seatsJohn C. Maxwell: The 21 Irrefutable Laws of Leadership
Referenced for the Law of the Lid (your team's leadership ceiling matches the leader's own)Jocko Willink: Extreme Ownership
Referenced for "there are no bad teams, only bad leaders"Grow With Purpose podcast
More conversations for owners and leaders on building a healthy company
Listen to the full conversation: Episode 190 on the Grow With Purpose podcast