Cultivating a productive complainer

Tom is on your team. Tom complains all the time. He complains about the sprint planning process, the way tickets are written, the architecture, the makeup of the team, everything. Tom is never happy about anything.

We’ve all worked with Tom. You can probably think of a few Toms right now. There are two ways Tom can go:

1. The bad apple way: everyone gets sick of his nonstop whining and they flip their bozo bits on him.
2. The productive complainer way: everyone listens when Tom complains because they know from experience that it leads to valuable change.

Coaching Tom towards option two and away from option one is a hard management problem. It takes a lot of guts to say that something sucks. And it takes a lot of wisdom to identify a problem worth solving. The overlap of those two traits is small, but that’s where you want Tom to set up shop.

A few pointers that have helped me here:

• Ask Tom to constrain venting to 1-1s, not team discussions. Be very clear that whining without a productive mindset is not ok in team discussions.
• Maybe even create a separate weekly “vent session” 1-1 with Tom if it starts to monopolize your normal 1-1s.
• Ask Tom to write down every time he’s annoyed with something so that patterns can emerge, and his complaints can be prioritized.
• Take his highest priority annoyance to retro each week to open it up for discussion and agree on an experiment that may fix it.
• Whenever Tom’s complaints are about his coworkers, coach him on giving feedback and make sure he does it.
• Remind him that being upset at someone’s actions without giving them feedback guarantees things will never change. Coach him on becoming a visionary of people.

If Tom resists coaching, PIP him. A bad apple cannot be tolerated.