Your best manager has been weighed down and overburdened for two years. She runs her own department, covers half of another, and trains every new hire because nobody else can. She’s tired in a way a long weekend doesn’t fix.
Then she gives notice on a Tuesday, you look at the people behind her, and not one of them is ready to do what she did.
Here’s what that moment hides: the people who could have been ready are usually already in the building. We just don’t see them soon enough.
I sat with a lot of owners and executives on that Tuesday. I’ve also been the one not seeing.
The bill
A few years ago, I promoted a leader into a role she was built for. A few months in, one of her teammates asked her, “How can I get to do what you do?” Her answer: “Talk to Jeff. He can help you get there.”
When it reached me, two things caught me off guard. I hadn’t seen that teammate as ready, and I hadn’t realized I was the one who could remove the barriers in front of her. I’m glad to be that person. But it took her asking for me to see what was already there.
We were always going to pay for the leaders coming up behind our best people. The only question is when, and on whose terms.
The bill shows up in three places that we rarely trace back to the same source.
1. The first is the people we hire from outside, and the ones inside who stop waiting. When no one is ready to move up, we go to the open market. A search drags on for months, there is a recruiter’s fee, a salary above the posted range, and a year before the new hire learns how the company works. It teaches our best people a lesson we never meant to teach: the way to move up is to leave. Our most promising person watches an outsider land the job she wanted and stops waiting.
2. The second is the managers we set up to struggle. We promote our strongest doer and ask her to lead people, then hand her the title without the skills that make the title work. She figures it out on her own, or she doesn’t. Her team feels the gap first. On any given Tuesday, it looks ordinary: a check-in that turns into a venting session she doesn’t know how to close, a hard call she sits on for a week, a good employee updating a résumé nobody knows about. None of this lands on a report until it lands as turnover.
3. The third is the strategy that dies two layers down. The plan stalls in the middle, where a manager who was never developed to carry a vision lets her team settle back into how things have always been done. We announced the new direction in January. By March, half the company is still doing the same thing they did last year.
I see this pattern across Madison area companies, from 80-person manufacturers to employers with thousands. The team behind the top performers is one resignation deep, and nobody knows it until the resignation arrives.
Which brings me back to the people already in the building. What would happen if they didn’t have to ask?
The companies that get this right build a pathway that notices people sooner, maybe even before we think they’re ready (or maybe before they do), and helps them climb higher — on purpose.
It comes down to four plain organizational habits:
1. The business spots people with real leadership instinct earlier than they feel is necessary. Instinct shows up before the title does: the machine operator everyone asks when something breaks, or the one who asks how to do what someone else does.
2. It teaches the skills the title assumes, such as how to keep a check-in from becoming a venting session, how to give honest, kind feedback, or how to make a hard call without sitting on it for a week.
3. The organization lets people lead something real before they carry the
title, while the stakes are small.
4. It builds one shared language for good leadership so that operations and finance mean the same thing when they say someone is ready.
All four fit a normal budget and a normal week. Growing leaders is part of the work now, because the quarter where things settle down never comes.
We don’t get to choose whether we pay for the leaders coming up behind us. We only choose whether we pay on purpose, while there’s still time, or by surprise, on the worst possible Tuesday.
Pay on purpose, and Tuesday still comes — but this time when she gives her notice, we look at the people behind her, and someone
is ready.
Jeff Lovell is president of Leaders Rising Network, a Madison-based leadership and culture agency, and co-author of “Rising: How Leaders Help Organizations Thrive” (2026).
