Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

‍

Dear Quota Team,

‍

One of my reps is going through a rough personal situation. His fiancée called off their engagement a few months ago, and it really shook him. He’s been a consistently strong performer for over two years, regularly hitting or beating quota. I’ve tried to give him space to deal with it, and I genuinely empathize with what he’s going through (I'm divorced myself).

‍

But it’s been three months now, and he’s still missing his number by a wide margin. I know breakups can be brutal, but I’m starting to wonder: when does empathy turn into enabling? I don’t want to be heartless, but this is a performance-driven role, and the rest of the team is starting to notice. Should I keep giving him grace, or is it time to have a tougher conversation?

‍

Empathetic in Colorado 

‍

--

‍

Dear Empathetic

‍

Three months is more than fair. It’s time for a direct but compassionate conversation. If you want, you can share your own personal experience and how you overcame it. Let him know you care, but also remind him that if he just keeps focusing on it, he'll never feel better. He doesn’t need to be 100% right away, but he can’t mope around forever — getting back into rhythm might be exactly what he needs.