Ten Questions to Close the Year With Clarity

The final weeks of the year have a way of compressing everything into a short window. Budgets are due, teams are tired, and leaders are trying to close out results while also planning for a year that already looks uncertain. In the third-quarter AICPA and CIMA Economic Outlook Survey, only 36% of senior executives felt optimistic about the U.S. economy, and 46% said it was already in a recession or would enter one by the end of 2026, with inflation, rising costs, and geopolitical uncertainty still weighing on their outlook (AICPA & CIMA, 2026). Even so, 48% of those same executives remained optimistic about their own organizations, which suggests that many leaders are holding two very different stories in their heads at once.

For executive coaches, this is the moment when a well-placed question can do more than a polished plan. The questions below are designed for coaches to use with clients, and for coaches to ask of themselves, as the year comes to a close. Each one comes with a short explanation of why it tends to open up a more meaningful conversation.

Why the Wording of a Question Matters

Organizational psychologist Tasha Eurich found in her research on self-awareness that people who ask themselves “why” they feel or act a certain way often end up with less insight, because the question pulls them toward justifying themselves and replaying the past. Questions that begin with “what” tend to move people toward clearer thinking and practical next steps (Eurich, 2018). Most of the questions that follow are built with that finding in mind, so they invite honest observation and lead naturally toward action.

The Ten Questions

1. What decision from this year would I make differently with what I know now?

This question turns hindsight into a usable lesson. Leaders often move past their decisions quickly once the year gets busy, and this gives them permission to look back at one choice with fresh information. Coaches can follow up by asking what signal was missed at the time, which helps the client notice patterns worth watching for in 2027.

2. Where did I react when I could have chosen?

A volatile year pushes leaders into reaction mode, often without their noticing. This question helps a client separate the moves they made under pressure from the moves that reflected their actual strategy. The answer usually points to the areas where a little more structure, or a short pause before acting, would have produced a better outcome.

3. What am I still tolerating?

Every leader carries a few unresolved issues, such as a role that is not working, a process everyone works around, or a conversation that keeps getting postponed. These problems tend to roll into the new year unless someone names them. The word tolerating gives clients an easier way to admit what they have quietly been living with.

4. Which assumption about my market turned out to be wrong?

Plans for 2026 were built on forecasts about inflation, tariffs, demand, and hiring that shifted throughout the year. This question invites a client to update their thinking openly and to check whether next year’s plan still rests on an outdated belief. It also models the kind of honesty that teams notice and tend to copy.

5. Who on my team grew the most this year, and have I told them?

Year-end reflection can easily become a review of numbers alone. This question brings people back into focus and often prompts a simple, meaningful action, such as a note of thanks or a conversation about the next step in someone’s career. Recognition offered in December also tends to carry real weight as teams decide how much energy to bring into January.

6. What would I stop doing if no one were watching?

Leaders accumulate meetings, reports, and habits that look important but no longer produce results. Removing the audience from the question helps a client see which activities they keep mostly out of routine or for appearance. The answers often free up time and attention for the priorities that matter most next year.

7. Where is my optimism about my own company running ahead of the evidence?

The survey data showing leaders more hopeful about their own firms than about the broader economy makes this question especially timely. Confidence is valuable, and it deserves a check against facts like pipeline strength, margins, and customer behavior. Coaches can help clients keep their optimism while grounding it in numbers they could comfortably defend to a board or a lender.

8. What did I learn about how I handle uncertainty?

Very few leaders had a predictable year, which means nearly every client has fresh evidence about their own behavior under pressure. Some discovered they tend to move too fast, and others found they wait too long for clarity that never arrives. Naming the pattern now gives the client something specific to work on before the next disruption.

9. How has AI changed the way my organization works, and where am I avoiding it?

Artificial intelligence moved from experiment to everyday tool for many companies this year, and leaders vary widely in how closely they have engaged with it. This question acknowledges that reality without making it the center of the conversation. The second half tends to be the most useful part, since avoidance often signals a skill gap, a worry about roles, or a decision the leader has not yet been willing to make.

10. What is the one result that would make 2027 a success?

Year-end planning tends to produce long lists of goals that compete for the same time and money. Asking for a single result requires a client to choose, and the choice itself reveals what they believe matters most. Coaches can then work backward with the client to identify the few commitments that support that one outcome.

Putting the Questions to Work

Coaches will get the most from this list by using it selectively. Choosing three or four questions for a single session usually leads to deeper answers than working through all ten at once, and clients often benefit from receiving the questions a few days ahead so they can reflect before the conversation. It also helps to write down the client’s answers and return to them in the first session of the new year, which turns a reflective exercise into a starting point for accountability.

These questions apply to coaches as well. A coaching practice faces the same economic pressure as any other business, and coaches who take the time to answer them for themselves will bring more credibility and more empathy to their client conversations.

A good question asked at the right time can help a client see their situation more honestly than any report could.

References

AICPA & CIMA. (2026). AICPA & CIMA economic outlook survey: Third quarter 2026. Association of International Certified Professional Accountants. https://www.aicpa-cima.com/professional-insights/download/aicpa-and-cima-3q26-economic-outlook-survey 

Eurich, T. (2018, January 4). What self-awareness really is (and how to cultivate it). Harvard Business Review. https://hbr.org/2018/01/what-self-awareness-really-is-and-how-to-cultivate-it

Copyright © 2026 by Severin Sorensen. All rights reserved.