Dear SaaStr: What Do You Do When a Top Employee Slacks Off?
It’s a tough one.
Taking a bit of a break, needing to collect yourself, needing to even vent a bit — that’s OK. But what do you do when a top, trusted resource slacks off … for months?
I’ve found this is especially common in sales. One of your top reps gets really, really good at the playbook. Nails it. Makes $400k, $600k, sometimes even a stunning $1m a year (!). And then … things change.
Competition changes. A new CRO comes in. More investment comes in. You go upmarket. You go into new verticals. You split territories. They don’t get as many leads as they used to. The old playbook stops working as well. It just changes.
And when it gets a bit harder, that top sales exec sometimes starts to check out. Sometimes, even resent that it’s changed. Even if they are still making good money.

I wish I had the answer. But you have to try. Treat them the way you’d want to be treated:
- Cut them some slack at first. A rough month or two is not the end of the world. Sometimes, they just need time. They’ve earned it.
- Make sure comp isn’t the root issue. It rarely is for your truly top performers, but if it is, just fix it. Today.
- Be honest and have the conversation. Tell them you want them to keep crushing it. But be prepared to not love the answers you get back.
- Find them another role. This often doesn’t work in this situation. But you gotta at least try.
- Stall a bit until you hire their boss. Sometimes, a new VP or CXO above them can find a way to make it work. I’ve seen this. I’ve seen a new leader reboot someone that used to be one of the best. They can’t always get them all the way back to S-tier. But the best leaders try to maximize the top performers on the teams they inherit.
I wish I could say you can magically get them back to being … one of the best. I’d say 50% of the time, maybe 66% of the time, when an S-tier employee stops being one … they just aren’t in a place to get back. At least not at your start-up. And often, nowhere.
And especially if they become a bit toxic, and start to undermine others, it’s almost always too late to get them back. IMHE.
But give it a real shot. Sometimes, things just change so much in a start-up, there is no way back. Then thank them, tell them you love them, that they did an amazing job. Give them some more time. And then help them find the next thing.
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