Yaniv Preiss

The end of the year invites reflection. Hopefully, goals get reviewed, and leaders are encouraged to look back and learn.

And yet, some end-of-year reflections don’t produce learning, but comfort, and not because leaders are dishonest. It’s because reflection is often done in a way that quietly protects identity, reputation, and effort already spent.

If you’re a manager or leader, the risk at this time of year isn’t that you’ll be too harsh on yourself. It’s that you’ll explain the year in a way that makes sense – justification, and therefore makes change unnecessary.

Why reflection might fail leaders

Many do not regularly journal, and at the end of the year, fall into the Peak-End-Rule – remembering the past two weeks and something big that happened in the middle.

Most end-of-year reviews focus on questions like:

• What went well?
• What didn’t?
• What should we improve next year?

These sound reasonable, but they’re also structurally flawed. They invite storytelling, not pattern recognition. The human mind is very good at turning an eventful year into a coherent narrative:

• Externalizing failures, like the market, the reorg, lack of resources, AI disruption
• Internalizing successes, like strong execution, great teamwork, perseverence
• Smoothing over contradictions, like it was a challenging yet rewarding year

The result is a version of the year that feels complete, and therefore closed, but learning requires additional effort.

Reflection vs. learning

Reflection may ask: What happened?
Learning may ask: What kept happening, even when we tried to change it?

Learning may uncomfortably expose recurring patterns, not just isolated events, including your own role in it.

For example:

• How many times did you step in “just this once” to unblock things?
• How often did urgent delivery override agreed principles?
• Where did the same tensions resurface under different names?

If the same issues appeared and reappeared, they’re not incidents, but signals of a pattern.

Note that the same goes for positive developments, like “which area kept growing and creating impact?”

On many occasions, extracting the learnings is easier with the help of others, such as a peer, a coach, or an online questionnaire.

The danger of closing the year nicely

There’s a tendency to wrap the year up with meaning, acknowledging wins, lessons learned and expressing gratitude. None of this is wrong, but when reflection becomes only a closure, it eliminates the tension that pushes for learning.

If you end the year feeling relieved, justified and resolved, check with yourself whether you’ve actually learned, or simply explained the year well.

Questions to avoid self-deception

If you want an end-of-year reflection that may actually create movement, bridging from the past to the future, try these:

What conversations did I keep postponing, and what did that preserve?
Avoided conversations are rarely about courage. They’re about what the system gains by staying the same: harmony, speed, approval, or temporary stability.

What did I already know by mid-year, but didn’t act on?
Leaders may not lack insight, but rather agency – the permission from themselves or the system to act on it.

What will I regret 6 months from now that I should look into today?
This is a call to deliberately set direction.

Between 1 and 10, where am I on a specific topic? How can I move half a step up?
The number on the scale is your own interpretation, and invites you to think of the next small step you can take.

For this specific issue I am having right now, was it somehow better in the past? How so?
This invites revisiting past successes and what contributed to resolving them, either by internal or external forces.

If I could create a miracle to solve a single problem overnight, what would it be?
This helps focus on the most important issue. Now that it’s been clearly identified, what action can you commit to taking?

Rest

By all means, please celebrate success and enjoy the time off!