October 12, 2025
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This was incredible…
Last week, 50 founders (and their teams) came to my place in Montana to workshop their 2026 annual plan. Today I’m sharing the exact framework we used…
Kicking off Highland Workshops in Whitefish, Montana
It took me a while to realize how important annual planning really is. It’s the difference between starting the year ahead of the curve, or behind the eight ball.
On your front foot, or your back foot. Proactive, or reactive.
But, I gotta admit, the process can be painful. All those meetings, back and forth, buy-in, friction, approvals. Skipping seems a lot easier.
But that’s a bad idea, trust me. You’ll pay the price later in misalignment, conflict and poor results.
The extra work up front is well worth it.
⁂
Most CEOs don’t know how to lead their company through annual planning. I didn’t either, at first.
Today I’ll show you how I perfected it after nearly 20 years of trying. Seven simple, but very important, steps. Ready? Let’s go…
I. Draft your 2026 Northstar
When: September of prior year.
Who: CEO + 1-2 closest colleagues (i.e. a co-founder)
What: Your Northstar is the company’s central document for absolute clarity. A company-level roadmap for everyone to align to. Your Northstar includes:
→ Mission
→ Values
→ Vision
→ Strategy
→ Annual Goals
→ Annual Outcomes
→ Annual Health Metrics
You should revisit or redraft each component annually. Start the process in September of the prior year. Then launch the final Northstar at your company kick off in January (see step #10).
Don’t have the Northstar template? Click here to get it (free). Make a copy for your company and fill out every section for 2026 (use the expanded version). Once its finalized you can give access to the entire company. Feel free to brand your copy, just give us some love 🙂
II. Get leadership feedback & buy-in
When: October of prior year.
Who: Leadership team
What: Involve your leadership team in drafting your Northstar. Ask for feedback & questions. Focus on your vision, strategy and annual goals. Make sure everything is clear & the team is aligned. Keep numbers in brackets until they’re finalized.
III. Draft your financial plan
When: October and/or November of prior year.
Who: CEO + Head of Finance
What: Draft next year’s financial plan: a 12-month forecast that outlines how you expect to do next year. It typically includes a sales and revenue forecast, an expense forecast, and a profit & cash forecast. Make sure it aligns with Northstar.
Need help building your financial plan? I wrote a free article here to check out. I also created an hour-long masterclass on building financial plans, plus a financial plan template. Both are available through Highland Academy (you can start with a one-week free trial).
IV. Draft team-level goals
When: October and/or November of prior year.
Who: Functional Leaders
What: After the leadership team reviews the company-level goals and outcomes, they can start drafting their team-level goals for next year. These are the top 3 things they can focus on to help the company achieve its goals. Each leader should be specific on what company-level goal/outcome theirs align to.
V. Review & approve team-level goals
When: December of prior year
Who: Leadership team
What: First, the CEO meets with each functional leader to give feedback on their team-level goals. Focus on difficulty level (challenging but realistic), and strong alignment to company-level. Next, each leader presents their goals to the full leadership team. Best done during an end-of-year leadership offsite. The team gives feedback & refines as a group. Iron out cross-functional misalignments – this is key!
Need a goal system that actually works? I wrote about my struggles with OKRs here. Also, the system I switched to, here. And last but not least, I created an hour-long masterclass on rolling out the right goal system in Highland Academy (you can start with a one-week free trial).
VI. Get financial plan approval
When: Mid December (review), Early January (approval)
Who: Board of Directors
What: Send your near-final financial plan to the Board of Directors for review and approval. The BOD waits for the year to end before giving final approval, but (usually) lets you start executing to plan by Jan 1st. If you don’t have a BOD, the main owners of the business need to align on the forecast.
VII. Host an annual company kick-off
When: January of new year
Who: Entire company
What: Get the whole company together for a special all-hands in January. Present your updated Northstar to the entire company. Each functional leader presents their team-level goals. Include a heavy dose of mission & values. Make it uplifting, inspiring and impact-centric.
⁂
Annual planning is a leading indicator of next year’s results.
Stop winging it. Follow these 7-steps and your team will enter the new year more aligned than ever.
Till next time,
Never say die 🏴☠️
~~~
P.S. I want to give a big thank you to all of the Highland members who made it out to my place in Montana this past week! It was an incredible experience…
My wife, Carrie, and I built our property to host events just like this one. So it’s incredibly rewarding to see it come to life and be able to host Highland members throughout the year!
Who knew annual planning could be this fun?
Music, food, drinks… what?!?! Private dinners around town. Hikes in Glacier National Park. Yoga in the morning.
We took things to the next level this year…
But, we actually got shit done too. Two straight days of creating our 2026 Northstar together. Revisiting values, vision, strategy. Creating annual goals, outcomes & metrics.
We all came out stronger at the end!!!
This is where FOMO kicks in. Bu you don’t have to keep missing out…
Join us at my future events by applying to Highland today.
We do a quick (and painless) call to determine the fit on both sides. Zero strings attached. No sleazy pitches.
See you at the next one!
🐐🏔️
