In recent years, I’ve begun having a one-on-one meeting with each of my direct reports every week. Sometimes these are twenty to thirty minutes; sometimes they’re a bit longer. The agenda is mostly driven by them; it’s a time when they can bring questions, challenges, opportunities, and ideas. We can discuss them, and they have my undivided attention. It’s also the time when I can ask them questions like the following:

  • What are you learning right now?
  • How did that last initiative work? What did you discover? What would you repeat (or not)?
  • What are you working on?
  • Is there anything you need my input on that’s keeping you from moving forward?
  • Are you currently running at a sustainable pace? If not, why not?

Over time, as trust is built, we can dive deeper than operational questions:

  • What are your greatest struggles or joys in your current role?
  • What was your best day at work in the last two to three months? Why?
  • What was your worst day at work in the last two to three months? Why?
  • If you could do anything, what would you do?
  • What role do you see yourself in next?
  • How can I help you to develop and grow as a leader to get there?

It’s a time I can ask for feedback from them and share feedback with them. That helps our team grow stronger intentionally.

It’s also a time when we can discuss (and I can evaluate) if someone is appropriately challenged, under-challenged, or dangerously over-challenged. That’s crucial information for every leader to know about their direct reports and senior leaders. It helps us know where to best deploy organizational resources like people, time, and finances.

Through these conversations, I’ve discovered far more about the hopes, dreams, struggles, and expectations of the team members I work with, and I’ve learned how I can pray for, equip, and encourage them in their current role and beyond. It also helps me discover if their pace is sustainable or if our team is over-demanding of them. I believe that’s part of shepherding them well.

Evaluations are then ongoing, not just once a year. Having a once-a-year meeting where you attempt to recall all the good, bad, and ugly for an entire year never made good sense to me. I do evaluations while things are fresh. We provide accountability through our weekly one-on-one meetings. “What are you working on?” “Did you do what you told me you would do when you said you would do it?” This is when excuses begin to go lame; having an excuse every week for why you didn’t do what you committed to gets old fast.

Accountability means people will either get things done and improve or leave, but there are never any surprises about performance issues.

How are you thinking about and executing evaluations these days? What have you learned about this in the last few years? What advice would you give you five or ten years ago if you could?

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