Some years ago I needed to step away from the business I had co-founded. Not gradually, and not on a timetable I chose. I needed someone to run it, and I needed them soon.
So I did the sensible-looking thing. I engaged an executive search firm, ran a proper process, and hired an experienced expatriate operator to be my Integrator — the person who would run the company day to day. She had done the job before, at a larger company than mine. I paid her more than I had ever paid myself.
Within months I was close to losing my senior leadership team.
She was not a bad leader. She was a good leader in the wrong culture, and I had not thought seriously about the difference. Her instincts had been formed in a different kind of company, in a different part of the world, and the way she made decisions and gave feedback did not land the way she intended in a Philippine business with a team that had grown up together.
The team did not complain loudly. That is the part I want other founders to hear. In a high-context culture, people do not tell you it is going wrong. They go quiet, they stop bringing things forward, and then one of them asks for a conversation about their future. By the time you get the signal, you are already several months into the damage.
I had hired for the résumé because I was in a hurry. What I needed was someone the team would follow, and that is not something a search firm can assess for you.
We had an honest conversation. To her credit, she agreed the fit was not there and resigned gracefully. She could have made that far harder than she did, and she did not.
Then I spent about three years rebuilding the leadership team from within. Promoting people who knew the business, teaching them what they had not had to know before, and being patient in a way I had not been patient the first time. That team is the one that took the company through to its acquisition in 2023.
The search took roughly three months. Recovering from it took three years.
That is the real trade in succession, and it is almost always presented backwards. Hiring from outside looks fast and building a bench looks slow, so founders under pressure choose the fast option. But the outside hire is only fast if it works, and the odds are not as good as the search firm’s presentation suggests.
Succession is not a hire. It is a bench you built earlier. The founders who transition well started developing two or three internal candidates years before anybody needed to move.
A leader who cannot read your team will not get the chance to demonstrate their expertise. Especially in face-saving cultures, where you will not be told what is going wrong until it has already gone.
I was genuinely under time pressure. That was real. What was not real was my assumption that the fastest-looking option was the fastest option.
Hers was, and it mattered. A leader who leaves well leaves a team that can recover. A leader who leaves badly leaves a team that learns not to trust the next one.
Three months saved, three years spent. That is the exchange rate nobody quotes you.
I now spend a good deal of my working life helping founders build the leadership team they will eventually hand things to. Not because it is a tidy business model, but because I did it the other way round once and I would rather other people did not.
