A CEO told me recently: “We always end the year with good intentions, but by the time we finalize our plan, Q1 is already slipping away. We spend more time catching up than leading.”
That’s the danger of waiting too long. If you want to create enterprise value in 2026, you can’t afford to coast through the final months of 2025. You need clarity, alignment, and foresight now — not later.
Here are ten questions every mid-market CEO should be asking to prepare their organization for the year ahead:
- Do we have the right Vision for the company? If your vision sounds like “the #1 provider” of something, push deeper. Reed Hastings didn’t say Netflix would be the best DVD rental company. He dreamed 20 years ahead: “To be a global entertainment distribution company.” That’s the kind of vision that builds value.
- Do we have Vision Clarity around our priorities and values? Gallup found that 78% of employees believe leaders don’t provide clear direction. Clarity isn’t about writing words on a wall — it’s about CEOs and their First Team living and communicating the vision daily.
- Is your First Team focused on the right things? If your senior leaders are more loyal to their silos than to you and each other, alignment is broken. And broken alignment kills execution and drains enterprise value.
- What are your top strategic priorities for 2029 — and are they still valid? Review the three-year plan. Markets shift. Competitors adapt. Use new insights to refine your 2026 priorities and fill the gaps in talent, infrastructure, and resources before January.
- Is your culture driving productivity and innovation? Culture either accelerates growth or quietly blocks it. Reflect on whether your culture in 2025 fueled agility — or stifled it. Decide what must evolve for 2026.
- What’s the state of your Talent? What got you here won’t get you there. Do you have the right people in key roles to support your growth strategy? And do you have a succession plan — including for your own role?
- What changes in customer behavior matter most? Customers decide the value of your business. Have their expectations shifted this year? If so, your 2026 strategy must adapt to meet them where they are.
- How has the competitive landscape changed? Your competitors have been moving too. Which of their moves affected your positioning? What adjustments do you need to make now to stay ahead in 2026?
- What operational inefficiencies are dragging you down? Growth creates complexity. Complexity creates inefficiency. Identify the slow, outdated, or overcomplicated processes today — and fix them before they slow you next year.
- Does your organizational structure support your strategy? The right design creates accountability and agility. The wrong one creates confusion. As you prepare for 2026, make sure your structure is fit for the growth you’re chasing.
These aren’t just planning questions. They’re value questions. The answers shape whether your organization enters 2026 with clarity and confidence — or stalls in confusion and reactivity.
CEO Call to Action: Block time before year-end to walk through these 10 questions with your First Team. Push for honest answers. Where you hear hesitation, that’s where enterprise value is at risk. Where you find alignment, that’s where value is created. Because preparing for 2026 isn’t about checking boxes — it’s about setting the foundation for sustainable, repeatable, transferable growth.