December is when you finalize budgets and polish board presentations. It’s also the month most leaders skip the one audit that actually predicts next year’s outcomes: your own leadership capability.
The gap between where you are today and the leader you’ll need to be in 2026 will determine more of next year’s outcomes than any financial model or market forecast. The Conference Board’s recent CEO survey reported that 89% of executives say leadership complexity has increased dramatically, while 73% feel underprepared for emerging challenges.
That gap isn’t about intelligence or experience.
It’s about whether you’re willing to take an honest look at your leadership before volatility forces the issue.
Below are the five questions that most accurately predict whether you’ll enter 2026 prepared, or struggle to keep up. And if you struggle, imagine what your teams will experience.
Questions to Ask Yourself Now
1. “When did you last make a significant decision without having all the data you wanted?”
This isn’t about recklessness; it’s about decision velocity and confident action in uncertainty.
Disruption is no longer episodic; it’s the operating environment. If you’re waiting for perfect clarity to move forward, you’re not making thoughtful decisions. You’re making late ones. Leaders who thrive next year won’t be the ones who can see further into the future; they’ll be the ones who have developed decision-making frameworks and practiced learning fast, deciding quickly, and course-correcting without losing momentum.
If you’re waiting for perfect information, you’re not making timely decisions. You’re making late ones. Your competitors aren’t waiting, and neither are the opportunities that will define 2026’s winners
Ask yourself: How many strategic decisions have you delayed in the past 90 days waiting for more clarity? What did that delay actually cost you — time, opportunity, or credibility?
2. “Can you articulate your top three strategic priorities without looking at your notes?”
I ask executives this question regularly. The ones who pause or stumble are usually the ones whose organizations are drowning in competing initiatives.
Clarity starts at the top. If you can’t immediately name your top three priorities — along with what you’ve deliberately chosen not to pursue — your team will struggle to align their work.
When leaders lack priority discipline, organizations experience:
- Competing or redundant initiatives
- Scattered accountability
- Strategy that never becomes execution
- Teams constantly asking for direction rather than running with it
Every leader believes they have priorities. Few can articulate them cleanly enough that their teams can act on them without escalation.
Ask yourself: If I asked my direct reports right now to list our top three priorities for 2026, would they all give me the same answer? Could they tell me what we are intentionally not doing?
3. “How much time did you spend this year building capabilities versus managing crises?”
This one reveals whether you’re leading or just keeping up.
Crisis management is part of every executive role. But if firefighting dominates your time, you’re not building leadership capacity. You’re falling further behind on strategic capability development.
Companies that consistently invest in leadership development through economic cycles achieve 2.4 times higher revenue per employee and 1.9 times higher profit margins.
The executives entering 2026 strongly aren’t the ones who avoided the flames. They’re the ones who built long-range leadership and decision-making capabilities while navigating daily crises.
Ask yourself: What percentage of my time in 2025 went to developing leaders and strengthening systems versus responding to immediate problems? If I continue that ratio, where will my organization be in three years?
4. “Do you have genuine peer relationships in which you can admit uncertainty?”
Leadership isolation is real. The higher you go, the fewer safe spaces you have to say, “I don’t know,” test ideas, or get candid feedback. Your team needs you to project confidence. Your board expects decisive leadership. Your shareholders want certainty.
But isolation erodes decision confidence. The executives who navigate complexity best have deliberately built relationships where they can be transparent with peers who challenge assumptions, widen perspective, and provide unfiltered insights.
This isn’t about therapy. It’s a performance advantage.
Ask yourself: When did I last admit uncertainty to a peer and get genuine help thinking through a challenge? If the answer is “I can’t remember” or “never,” what is that costing my decision quality?
5. “What did you learn about yourself as a leader this year that surprised you?”
This might be the most important question of all.
Most executives can tell you what they learned about their market, their competitors, or their industry in 2025. Very few can clearly articulate what they learned about themselves. Yet your leadership patterns — how you respond under stress, how you make decisions, how you communicate, how you develop people — have more influence on your organization’s trajectory than any market trend.
Notably, 88% of directors say they could personally take steps to improve their effectiveness, with 45% prioritizing ongoing education or training while others focus on improving interpersonal dynamics.
Where are your blind spots? If you don’t know, your leadership style might limit your organization’s performance.
Ask yourself: What feedback did I receive this year that made me feel defensive? If I assumed that feedback was accurate, what would I change?
Why This Audit Matters More Than Your Financial One
Nine out of ten CEOs say they’d like to replace one or more directors on their boards to best meet the needs of their businesses. When board refreshment isn’t possible, many CEOs pivot to investing in their own development, upskilling themselves to meet evolving needs of their organizations and industries.
Your board, your team, and the market are all evaluating you.
But the most important evaluation is the one you conduct yourself. Your organization’s execution, culture, and business outcomes will reflect the quality of your leadership.
The executives who enter 2026 in the strongest position aren’t the ones with the biggest budgets. They’re the ones who’ve honestly assessed their leadership capabilities and invested in developing the ones that matter most… before they need them most.
The pattern I see in executives who consistently outperform isn’t complicated:
They treat leadership development as strategic investment, not discretionary expense. They actively seek opportunities to learn and strengthen their capabilities by pursuing coaching, joining peer forums, engaging in structured reflection, and deliberately honing their skills.
The capability you need next gets built now.
The relationships that will help you navigate uncertainty need to be cultivated before you need them. The self-awareness that prevents catastrophic blind spots requires continuous work.
As you head into year-end planning, ask yourself this: Are you investing as much in developing your leadership capability as you’re investing in your strategic plan? Your ability to execute the plan depends entirely on the quality of your leadership.
The five questions above aren’t comfortable. But discomfort is the price of growth, and growth is the price of leadership that can handle what’s coming.
Audit Assist
If you want a simple, structured way to run this audit, I created a comprehensive Year-End Leadership Audit tool that expands on these questions with diagnostics, scoring rubric, and development recommendations. Message me and I’ll send it to you so you can prepare to enter the new year with clarity about your leadership readiness.
If you’d prefer a brief, confidential conversation to talk through your answers and identify your highest-impact leadership focus for next year, set up a short call.
Which of these five questions hit closest to home?
I’d love to hear what surfaced for you.
