At a growing startup we once worked at, there was guy who’d been amazing, been with the company since the earliest days, but who had somehow “lost the tune”. We’ll call him Rocky. Rocky had done a bit of everything, from programming to sales to customer support to graphic design. He’d been one of the first hires (though not the first, and amongst his many talents was his unerring recollection of the employment records of everyone who’d ever worked there), and the company owed a substantial portion of its entire existence to him. He was cheerful and intelligent and incredibly hard-working.
And he was failing. He wasn’t getting his job done, and had started… not exactly complaining, but expressing a certain amount of dissatisfaction with his role.
The company’s leadership were astounded. All this time Rocky had been, well, the rock upon which so much of the company depended. We were only twenty or thirty people at that time, but Rocky knew everything about the product, the business, the customers. It was hard to imagine a world without him. But the reality was Rocky was becoming toxic, a drag on everyone else.
What Got You Here Won’t Get You There
Many startups will face this challenge. People who were utterly essential, who you couldn’t imagine succeeding without back when it was just a handful of you, can sometimes become a drag on the whole team. It can happen quite suddenly.
People burn out, they get lost in the shuffle, sometimes they’re just better suited to a smaller team. Lots can happen as you’re growing.
With Rocky it was hard to tell. He was still cheerful, still evincing enthusiasm for the company. He just didn’t seem to be executing the way he used to, and leadership were getting tired of excuses.
How Do I Handle This?
A lot of leadership texts will talk about the need to be tough, to remove under-performers. Well, that’s true, but it pays to take a softer touch with the old guard.
Remember that everyone in the company is watching. How you handle an under-performing ex-rockstar will be seen by others as a model for how they can expect to be treated should they find themselves struggling.
The truth is that often, for a growing company, this can be the first real test of your ability to manage performance. But with a long-time employee, hopefully you’ve got a lot of trust built up. You should be able to sit down with them and be honest about your disappointment and worry.
This is what happened with Rocky. He didn’t actually report to me at the time, but the CEO asked me to speak to him on account of Rocky had mentioned being interested in joining my team. So we chatted. He was clearly down, lacking his usual energy and confidence. I mentioned it and he agreed that he was off his game, so I asked him what he would LIKE to be doing at the company. Since he knew everything and everyone, he was in a great position to see what was going on, and he mentioned he’d heard we were hiring a project manager and could he move into that role?
It was a tough call. Project management is a specialized set of skills — a set I don’t myself possess. So I wouldn’t be able to mentor Rocky in his first shot. I also had the feeling that project management wasn’t really going to be his bag. Rocky was best at dealing with inter-group communication, improvising responses and making sure that our customers always felt like they’d been treated well. Meticulously tracking priorities and timelines, following up with developers and predicting the impact of schedule mishaps were not likely, in my opinion, to give him a lot of job satisfaction.
Put A Box Around It
There’s a common canard that it’s better to not hire than hire the wrong person. That may be true for total strangers, but not for someone who’s worked hard and helped build your company’s nascent culture. There was no question that Rocky fit in. The question was how much risk we were willing to take on his behalf.
I resorted to one of my favourite management tricks: the time box. Rocky and I agreed that we’d try him out as a project manager on one project for three months. We’d review at that time and see if we thought it was worth proceeding. Hiring a new project manager was probably going to take a couple of months anyway, and I told Rocky I would continue to interview candidates in the meantime, so we weren’t really risking very much if it went sideways.
And with a three-month vision, Rocky could get energized about what he needed to deliver. He charged in like his old self and got to work. We checked in each week, counting down to the end of the trial period.
Sometimes A Happy Ending
It may not work out. But taking the effort to find a new place for an old rockstar is almost always worth it. They’ve given you their best, and it’s not unreasonable to show some patience when somebody like that struggles. And being clear about expectations, especially in a new role, is a good way to set things up for mutual understanding.
Rocky was not cut out to be a project manager, it turned out, but maybe he just needed a few months away from the grind, or perhaps to get used to the new size of the company. After our trial period he decided project management wasn’t all that he’d hoped, and he moved into a new position helping lead our customer support team. He’s still there, still killing it, still making the company’s customers feel valued and respected.
I’m not. In the end, I was the one who had a harder time adjusting to new realities.