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People ask me all the time what to do when somebody they employ isn’t working out. It’s one of the most common pain points I hear from founders, creatives, and anyone who has tried to build a team around themselves.
I’ve never run a big team, but I have dozens of freelance contractors who work with me, and rarely have problems with them. I have an uncommonly high success rate in getting projects done, and I think that’s mainly because of the way I set up the relationship between us from the jump.
Whenever someone tells me one of their workers isn’t cutting it, before giving advice I ask:
- Have you recorded your process and created a standard operating procedure (SOP)? If the only place your process lives is inside your own head, you haven’t really handed off the work, just the label.
- Has this person actually done this kind of work before? Experience matters and enthusiasm doesn’t replace it. Be honest about whether you hired someone ready for this role, or someone you hoped would grow into it.
- Do they have a priorities list? Not a vague sense of what’s important written on a napkin, but an actual written list that tells them what to work on, in what order, and what done looks like.
- Do they have a benchmark for how long this work should take? If they don’t know what good looks like on the clock, they can’t know whether they’re falling behind.
In my experience, most people aren’t struggling because they are “bad at their job” so much as out of their depth and don’t want to admit it. You hired somebody to take a burden off your shoulders, but before they can you have to provide them the resources they need to do so, including training.
Employees don’t come with your context pre-loaded. They are not you, and the gap between what you expect and what you explained is almost always wider than you think. It takes them time to get up to speed and take over a task at your speed and your level.
The single best thing you can do is open a path of communication before there’s a crisis. Let your employees know early that you welcome questions, that asking is safer than guessing, and that silence is the one thing that will actually cause problems.
Most people are more willing to ask when they know the door is already open, especially if you walk the walk and don’t just talk the talk.
With my own team, everyone knows there is essentially one rule: the only time I will get cross is if you deliver something that isn’t good enough without asking questions first.
If you need help, ask for it. If you don’t, then I assume you don’t need help. When I find out you do, that vexes me.
I pay for taste. I hire people who can look at their own work and know whether it clears the bar. That is their only real job. When someone delivers something that misses, it doesn’t just mean the work is wrong. It means their taste is off, and if I can’t trust their taste, I can’t trust them to work independently. At that point, I’m not getting what I’m paying for, which is freedom.
So when that happens, I send some version of this email. It might be useful to you too.