Two Questions for December

Every December, I ask my clients the same two questions.

They're simple. They take about ten minutes. And they almost always surface something important.

Question 1: Where were you a year ago — what had you planned, and what actually happened?

Question 2: If you were sitting here a year from now looking back, what did you accomplish in 2025?

The first question is humbling. Plans rarely survive contact with reality. The promotion you expected didn't come. The transition you dreaded turned out to be the best thing that happened to you. The goal you were certain about quietly stopped mattering.

Looking back with honesty — not judgment — shows you what you've actually learned. Not what you intended to learn. What you actually learned.

The second question is clarifying. Not because you'll predict the future correctly — you won't. But by putting yourself in that chair a year from now and looking back, you're forced to name what actually matters. Not vague hopes. Concrete accomplishments. Things you can point to and say, "I did that."

Your answers today will be different than they would have been twelve months ago. That's the point.

The gap between those two answers is where the real insight lives. It's where you see what's shifted, what still matters, and what you're finally ready to let go of.

If you're a leader heading into the new year, I'd encourage you to take ten minutes this week. Write down your answers. Be honest. No one has to see them but you.

Sometimes the clearest path forward starts with an honest look back.