The 20 Questions Every Leadership Team Should Ask at Year-End
As the year comes to a close, most teams move straight into goal-setting mode for the year ahead. But the most successful organizations pause first. They reflect. They evaluate. And they extract the lessons that determine whether next year will be a repeat—or a breakthrough.
A thoughtful year-end review doesn’t just recap what happened. It clarifies what worked, what didn’t, and what truly matters moving forward. Whether you lead a company, a department, or a growing team, these 20 questions will help you close the year with insight and intention.
1. Strategy & Vision: Did We Move the Needle?
Strategy only matters if it translates into action and outcomes. These questions assess whether your vision drove real progress—or stayed theoretical.
What were the three most important goals we set at the start of the year—and did we achieve them?
What strategic decisions had the biggest positive impact?
Where did we fall short of our strategy—and why?
What opportunities did we miss or postpone that should be priorities next year?
Is our long-term vision still the right one based on what we learned this year?
Why this matters: Clarity at the strategic level prevents reactive decision-making and keeps leadership aligned.
2. Operations & Execution: Did Our Systems Support Our Growth?
Growth exposes cracks. This section evaluates whether your operations scaled—or strained.
What systems or processes worked exceptionally well?
Where did bottlenecks or breakdowns occur most often?
What operational problems did we permanently solve this year?
What should we stop doing next year because it no longer adds value?
What should we simplify to improve efficiency?
Why this matters: Complexity kills momentum. The best teams get better by getting simpler.
3. Financial & Business Performance: Did We Invest Wisely?
Revenue is only one piece of the performance story. These questions examine how well resources were allocated and risks managed.
What revenue streams, services, or client segments were most profitable?
Where did we underestimate time, costs, or effort?
Did we invest our people, money, and energy in the right places?
What financial or business risks did we manage well—and which surprised us?
Why this matters: Smart growth depends on knowing not just what earned money—but what earned it efficiently.
4. Clients & Relationships: Did We Deliver Real Value?
Client satisfaction is often felt before it’s measured. These questions reveal whether your service experience matched your intentions.
What patterns did we see in client feedback this year?
Where did we clearly exceed expectations?
Where did we disappoint—and what can we learn from that?
Why this matters: Retention, referrals, and reputation all stem from the client experience.
5. Team, Culture & Leadership: How Did We Show Up for Each Other?
Culture is built through behavior, not slogans. These final questions assess leadership, communication, and team health.
What roles, decisions, or individuals had the greatest positive impact on our team?
Where did communication, ownership, or accountability break down?
What would make next year feel like a true success—not just financially, but culturally?
Why this matters: Strong cultures outperform strong strategies when things get hard.
How to Use These Questions Effectively
Use them as a facilitated leadership session
Turn them into an anonymous team survey
Break them into quarterly reviews next year
Or use them in one-on-one leadership check-ins
The goal isn’t perfection. The goal is awareness, alignment, and momentum.
Final Thought
The companies that grow the fastest are not the ones that avoid mistakes—they’re the ones that learn the fastest. A powerful year-end review doesn’t just close the chapter on last year. It sets the tone for everything that comes next.
