When was the Best Time to Plant a Tree?
This old proverb says the best time to plant a tree was twenty years ago. The next best time is now.
The same is true for your 2027 strategic plan and budget. If you have not started, today is the day. The leaders who finish strong in Q4 are usually the ones who already know where they’re headed in Q1.
As an executive coach, I am fielding more calls this fall from leaders asking the same question:
Where do I start?
Here are six simple steps to get the momentum going.
1. Put it on the calendar
Planning that isn’t scheduled does not happen. Block two or three 90-minute sessions over the next few weeks, away from email and, if you can, away from the office. Treat them like a board meeting and protect them. It could be a board meeting of one, just you, or collaborating with your team.
Turn your what’s into when’s, be it calendaring for budgeting, strategic planning, or fun things, when its on the calendar there is a MUCH higher probability that it will get done!
2. Dream before you budget
Resist the urge to open last year’s spreadsheet. Start with a blank page and one question:
What would going big look like?
Picture your organization on December 31, 2027.
- What has changed?
- Who have you hired?
- What are customers saying about you? Write it down before reality edits it.
3. Know three numbers: planned, needed, and possible
What growth is planned, the number that falls out of current momentum? What growth is needed to fund your people, your investments, and your vision? And what would 2x look like? You may never commit to doubling, but asking the question exposes the constraints, assumptions, and bold moves an ordinary plan quietly avoids.
4. Make AI part of the plan, not a footnote
Ask two questions. How will you personally use artificial intelligence to work better: drafting, analysis, meeting prep, decision support? And where can AI make your organization more efficient and effective: customer service, finance, sales, operations?
Then go beyond using AI as a “super Google.” Faster answers are the smallest win. The real gains come when AI helps you think through scenarios, draft first versions, and automate the repetitive work that eats your team’s best hours. Budget for it: tools, training, and time to experiment.
Once you complete your 2027 budget, AI can plan around it layers in things such as:
- What if interest rates go up next year?
- Is your business impacted by weather, what if it rains 20% more days than in 2026?
5. Choose a few big priorities
A plan with fifteen priorities has none. Narrow your list to three to five initiatives that matter most. For each, name an owner, a measure of success, and a first milestone for Q1.
6. Bring your team in early
Your people see what you don’t. Share your draft vision and ask what’s missing, what’s unrealistic, and what they would add.
Plans built with the team get executed by the team.
Plant the tree today!
You don’t need a perfect template to begin. You need one block of time, one bold question, and the discipline to keep going. The leaders who look back on 2027 as a breakthrough year are planting those seeds right now.