Five Questions Leaders Should Ask Themselves Before Year's End

As we’re getting in the midst of end of year planning, strategy sessions and holiday busyness often crowd out something just as critical: self-reflection. Before setting 2026 goals, leaders should pause for three vital internal conversations.

Leadership isn’t just about setting direction for others — it’s about continually checking in with yourself. The strongest leaders are the ones who ask hard questions before external challenges force them to. That’s why, before the new year begins, it’s worth slowing down and taking stock.

Here are five questions every leader should sit with before turning the page to 2026:

1. "What did I avoid this year that I shouldn't have?"

Avoiding an issue isn’t the same as being patient…it just delays the progress you need to make.

Ask: What friction did I feel but not address? What feedback did I receive but not act on? The answers might sting, but they’re gold for growth.

This question digs up blind spots. Often, the things we sidestep — whether it’s a tough team dynamic, a misaligned strategy, or a nagging performance issue — are the very things that keep us from moving forward. Naming what you avoided is the first step to ensuring it doesn’t carry into 2026 with you.

2. "Am I still the right leader for where we're going?"

Organizations evolve, and so must leaders. This isn’t about whether you’re good, but whether you’re the right fit for the specific task at hand, in this moment.

Ask: What new skills must I step up to? What strengths should I double down on? Where do I need complementary talent?

This reflection isn’t about self-doubt — it’s about self-honesty. Every new stage of a company requires slightly different muscles. Sometimes that means expanding your own toolkit, and other times it means empowering others to lead in areas where you shouldn’t. Growth as a leader often looks like letting go as much as stepping up.

3. "What am I modeling that I don't realize?"

Your team notices the gap between what you say and what you do.

Ask: What culture am I creating through my daily actions? What do people say about my leadership when I’m not in the room?

Culture isn’t built in all-hands meetings or strategy decks — it’s built in the small, repeated behaviors leaders demonstrate every day. Whether it’s how you handle stress, how you give feedback, or how you treat time off, your team is watching and learning. The question is: are they learning what you intend to teach?

4. "Where is my AI strategy?”

AI isn’t just an efficiency tool—it can eliminate entire processes and redefine value.

Ask: Which processes exist only because of old constraints? What would we do if reporting, analysis, or planning took nearly zero time?

AI has already shifted from buzzword to business backbone. The question is no longer whether leaders should be thinking about it — but how. Leaders who wait risk being outpaced not just by competitors, but by the expectations of their own teams. A clear AI strategy in 2026 isn’t optional; it’s table stakes.

5. "What would I do differently if I knew my best performer was leaving in six months?"

What matters here isn’t a replacement plan, but building a team that isn’t fragile if someone leaves.

Ask: What would break if my top three people left tomorrow? Which roles or systems need redesigning so value isn’t concentrated in a few individuals?

Strong leadership is about designing resilience. If your organization depends too heavily on a few “irreplaceable” people, you’re not building for the long term. The best teams are those where knowledge, systems, and culture are spread widely enough that no single departure can derail progress.

The Hidden Pattern

Each of these questions forces you to uncover assumptions you’ve normalized. The leaders who thrive in 2026 will be the ones who challenge invisible defaults.

Action Step: Schedule a block of time to spend time with yourself. The clarity from these uncomfortable questions will do more for your leadership than any framework or productivity hack.

Even a single afternoon of reflection can set you up for a more intentional, resilient, and future-ready year.