CEOs: The Three Questions That Will Define Your 2026

If you're a growth-stage CEO you don’t need another article telling you how difficult the past five years have been. You lived it–pandemic, market whiplash, AI disruption–all while trying to keep your teams and investors aligned and fight for your numbers every quarter.

What you might need, however, is space to think.

So over the holidays—while everyone else is distracted with their own lives—take a moment to sit with the questions you’re avoiding. The meeting you keep rescheduling, the struggling initiative that no one will cut, the underperforming executive you’re working around. Confronting them will transform your year. If you need a place to start:

1. Are we focused or just busy?

2. Do we have the team for where we are going?

3. Are we leading with AI or just experimenting?

We work with dozens of leadership teams on these questions. In these discussions, there are trends that separate teams that break through from the ones that stay stuck. The difference is not experience or resources. It’s willingness to explore uncomfortable truths and act on them.

Question 1: Are we focused or just busy?

Here's a conversation that has played out multiple times in my career:

Me: What are the non-negotiables for your company to deliver in the next 12 months?

CEO: We have multiple spreadsheets outlining our OKRs with supporting metrics that my CFO maintains and can walk you through.

Great that you have OKRs, but if you can’t list 3-5 things everyone understands without a spreadsheet, your team is not focused. Decisions are made on the ground at a million miles an hour, not in Excel. Let me give you an example.

Before a recent offsite, we asked each executive to independently list the company's most important initiatives for the next quarter. When we combined the lists there were 30+ items with little overlap. They had company OKRs and the CEO had assumed the team was aligned. However, in practice they were far from it.

After a difficult afternoon working through every initiative the team aligned on three non-negotiable priorities, two opportunities to explore, and ten things to stop doing. It took trade-offs, and it was uncomfortable, but that same team is moving faster today than ever.

A list of 10+ priorities isn’t a strategy, it’s a wishlist. It’s imperative to help your team focus in order to accelerate.

Signs that you are not focused:

• The list of executive-level priorities is 10+ items long.
• Decisions take too much time, debate, and socialization.
• Your team says you “chase shiny objects” to your face (or behind your back).

What to do about it:

• Work with your team to prioritize three outcomes that must be delivered to grow the core business (e.g., a product release, fundraise, or acquisition target).
• Identify 1-2 additional bets to future-proof the organization. These are future sources of revenue or moat expansion that won’t pay off for 12+ months.
• Assign accountable owners for each priority and communicate them over and over (and over) to the organization.

Question 2: Do we have the team for where we’re going?

This one's hard because it's personal. The team that has been with you since the beginning–given nights and weekends, believed in you–will not be the same team at your exit.

In my experience, as teams grow from $50M to $250M in revenue, CEOs often change every executive role at least once and reorganize their team structure twice or more. This evolution is not failure—it’s normal. The “builder” who gets you to $50M is rarely the “scaler” who gets you to $250M. In 2025 alone we added 47 new executives across 35 portfolio companies as needs changed. Reframing this discussion is critical for teams to evolve with dignity rather than blame.

If you’re a CEO, you are likely dealing with a situation like this right now. You know the one I am talking about. You’re telling yourself “they’re a culture carrier,” “too much institutional knowledge,” or “they just need more coaching.” When I hear these justifications, I mark my calendar for six months and ask again. Nine out of ten times, the situation is the same and we've lost half a year.

The cost of delaying talent decisions is real. You need to build a team for where you're going and the longer that evolution is avoided the harder it is to catch up.

Signs it is time to evolve your team:

• You have more than 10 direct reports.
• More than 70% of your executives are in the largest role of their career.
• You haven’t stress-tested your organization design for where you will be in 18 months.

What you can do about it:

• Start with a blank slate. Without discussing specific people, sketch out the organization you would design today to drive focus. Stick to 8 or fewer direct reports.
• Honestly assess your current leaders against the deliverables required for the next 3 years of growth. Identify future leaders and gaps.
• Work with your People Leader (CPO, CHRO, or VP People) to plan your team’s evolution over 6-12 months to avoid disruption. Start now.

Question 3: Are we leading with AI or just experimenting?

The difference between companies that lead with AI and those that don’t often comes down to one issue: ownership. If AI strategy sits only with a “Head of AI” instead of with every functional leader, you're likely falling behind. The companies pulling ahead see AI as everyone’s job and have function-specific goals and measurable outcomes. AI isn’t just an innovation initiative–it’s how they are building their businesses.

Today, we work with organizations to achieve goals unheard of just two years ago. Engineering teams driving AI-generated code above 60%, HR teams deploying agent companions for every employee, and GTM functions running marketing campaigns pre-tested on synthetic data.

Many of our companies are moving beyond experimentation into focused P&L impact. We saw a company launch an AI-enabled product that contributed nearly 10% of revenue after just three months. Another doubled customer support capacity and cut time-to-resolution by 80% without adding any headcount. These were not moonshots; they were practical applications of readily available models and tools.

Across our portfolio, nearly all companies are now using GenAI in their workflows. It doesn’t work perfectly, but neither do people. As models evolve, employees are finding creative ways to use them and sharing those learnings. These companies haven’t just committed to a culture of AI; they have committed to a culture of transformation and they’re getting ahead.

Signs you could get more from AI:

• You’re running dozens of AI experiments but cannot point to one that has impacted your P&L.
• You delegated AI to a "Head of AI" working in isolation, rather than holding functional leaders accountable.
• You could not fill a one-hour all-hands with examples of ways the team has increased efficiency with AI.

What you can do about it:

• Set aside a specific budget for AI tooling and require that adopters share their learnings at the next all-hands.
• Pair your executive team with junior, AI-savvy employees as reverse mentors. This upskills the execs and gives high-potential talent exposure to leadership.
• Incorporate AI innovation into individual goal setting and performance reviews.

The Opportunity Ahead

An honest reflection on the questions above will surface endless opportunities. Sit with them. Stack rank them. Then cross off everything but the top two. Not the easiest, or the most urgent, but the two that will prepare you for where you are going. Write them down and revisit them. Then bring them to your team and commit.

The clarity you build this month will set the tone for the year ahead.