The Secret Entrepreneur: Why you have to be Machiavellian sometimes

The wicked web of deceit is something every boss has to weave sometimes to keep business on track

Of all the growing pains that come with a business, it’s the people problems that I find the most draining.

It’s not that the problems are particularly unpredictable, at least once you have some experience. After many years of dealing with teams it’s quite easy to predict what’s going to happen and roughly when.

The issue is that that they’re fairly constant once your business gets beyond 20 or so people, and sometimes getting the right outcome for the business means playing things in ways that are quite Machiavellian and frankly feel uncomfortable, but which are ultimately necessary.

A while ago we had a very senior person leave (predictable), which was a huge relief for myself and many others as, well let’s just say relationships had broken down.

The problem was that this could have destabilised things for more junior staff, who don’t (and shouldn’t) know the full picture. All they see is someone very senior heading out the door.

So when another, less senior but long standing member of staff came to me to resign shortly afterwards for entirely unrelated (and again, predictable) reasons, I had to play things carefully. Two established players leaving in quick succession would definitely rock the boat.

The truth is, I was hoping that this person would move on as they were quite overpaid for the skills we needed them for, they were blocking the promotion of a more suitable candidate for their role (who I really don’t want to lose) and we didn’t have anywhere else to more usefully use them. Sometimes a company and a person just naturally grow apart.

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Having to announce their departure at this time was not going to be a good move though, so I had to do something I never normally do, and pulled out all the stops to make them stay. This is usually a big mistake, once someone has decided to go, it’s best just to let them move on with grace (the good ones usually come back).

After a few agonising days of secret courtship, we worked out a whole new job role to keep them on board. This suited them but was frankly not something which was going to work for the company in the long term. I wasn’t worried about this though, I just needed the role to keep them on board for a few months until the dust had settled, but be flawed enough that after that they’d likely decide to move on again anyway.

This role moved them away from their existing team and introduced just enough tension in responsibilities to make things slightly awkward but allow their former team mates room to step up and realise that they could do things just fine (in fact, quite a lot better) on their own.

It worked like a charm. Chaos was avoided, morale was maintained and teams were restructured without them really even realising it.

Months passed, the dust settled and the potential leaver started to see the flaws in their new role. So when I (subtly) arranged a new opportunity to be presented to them, they took it and came to me to resign (again).

This time I just took it gracefully and wished them the best.

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