January 12, 2026
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I’ve been flooded with questions about annual company kick-offs recently (it is January, after all).
→ How can I nail mine this year?
→ What should the agenda be?
→ Anything I should avoid?
An annual company kick-off is a special all-hands meeting to kick off the year. It usually happens in January (if you’re on calendar year), and every person in the company gets the invite.
It’s a big moment. Turning the page on 12-months of hard work and getting people rallied around the next 12. If done right, it can shape the behavior of your entire company for many months, if not years.
But most CEOs waste the moment. Why? Because they don’t realize how high stakes it is. They think B- work is ok. Check the box. Get back to the “real work”. I mean, you do have lots of shit going on. Carving out a half day for a company kick off can feel like a waste of time.
This line of thinking hits at what separates average leaders from great ones: the average ones don’t understand that investing more effort in select situations can make their lives 1000x easier. Nailing your company kick-off is exactly one of these moments because it has a ripple effect throughout the organization that is tough to replicate.
Andy Grove calls this concept “managerial leverage” in High Output Management. What you put in is nothing compared to what you get out, especially in the weeks, months and years following.
So, the first-time-founder, or inexperienced operator, wants to enter the year by putting their head down and getting back to work. But this is exactly the wrong thing to do. Pick your head up. Bring your entire team together. Get them ready to do their best possible work in the year to come.
Your team needs three things from you:
Without this context, they can’t reach their full potential in the year to come. The annual kick-off delivers all three at once. It’s a shot in the arm that gives everyone the clarity to do their best work. Skip it and you put your team at an information disadvantage and make your own job infinitely harder.
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5 deadly sins of annual company kickoffs
Putting the kick-off on the company calendar is the first step. Now you have to execute at an A+ level. When a Highland CEO asks me how, here are the 5 things I tell them to avoid at all costs… with actions for each.
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1. CEO isn’t fully bought in
Weird right? How can the CEO not be bought in to their own company kick off? This happens when the CEO doesn’t think the kick-off is the most important thing they could be doing. And it shows through the agenda, the material and their energy. If the CEO isn’t dialed in and energetic about the coming year, no one will be. So, first thing’s first, get your head out of your ass and treat this like the super bowl moment it is.
ACTION: Treat your company kick off like the most important meeting of the year. Start your annual planning early (September of the prior year) so you’re 100% ready. Spend a lot of time on the agenda, flow, content and message. Do not hand this off to someone else.
2. Skips the big picture
Most CEOs dive into the weeds too early in their kick off. They’re all numbers and no mission, values or vision. Remember, you need equal doses of Purpose, Direction & Progress when building the agenda. Don’t skip the Purpose content, which answers the fundamental question: why are we all here doing this together? Don’t assume your ‘why’ is the same as every person in your company. You have to create ways for them to connect their personal ‘why’ to the company’s.
ACTION: Make sure your company’s Northstar is complete and refreshed where needed. Find ways to tie the company’s mission into the agenda. Retell the founding story in a way the company hasn’t heard before. Invite a customer to speak. Have members from the team talk about which company value is their favorite and why.
Want the Highland Northstar template for your company? You can access it here for free. Simply make a copy of the google slides and fill it in for your own company.
3. Skips honest reflection
It’s easy to think, let’s focus on the future without any reflection on what didn’t work last year, and what you learned from it. Always make room in the agenda for “how we did last year”. Skipping this is a big mistake. It will make the team feel like you’re trying to sweep results under the rug. Trying to move the goal posts or hide something. It’s the opposite of how you build real trust with your team.
ACTION: Go through last year’s annual goals honestly. What did you hit, what did you miss? Why did you miss and what did you learn from it? How did your successes and failures last year inform the plan this year? How is the company progressing overall? What are the highlights? What are the areas for improvement? Rally the team around both.
4. Lacks direction
Most CEOs I start working with aren’t clear enough on where the company is headed. This includes your longer-term vision (10 years), medium-term vision (5 years) and shorter-term vision (3 years). It also includes the strategy behind the 3-year: what’s our unique approach to accomplish our vision? How are we 10x better? And lastly, it includes your top 3 priorities for the upcoming year as a company. Not the goals, but how you plan to measure the success of each. These should be challenging but realistic for the team to accomplish in the 12-month span!
ACTION: Make sure your vision ladder is dialed in BEFORE you do your company kickoff (3, 5, 10 yr vision that ladders up). Get buy-in from your leadership team so everyone is aligned. Then create your top 3 annual goals for the year, with measurable outcomes. You can use the Highland goal framework, or something else. Either way, focusing the team around annual priorities is critical.
Want the Highland Goal System? You can access the free article here. I also wrote about the 7 essential rules of goal setting here. And I go into much more detail in Highland Academy.
5. It’s boring as F
If the entire company kickoff is the CEO presenting material to the company, then you’re losing. You need to mix it up. CEO should absolutely lead and be the facilitator throughout. But you should include other voices in the agenda. Senior leaders weigh in on reflections from last year. You could add breakout exercises for the whole team. Or invite a guest speaker to inspire the team.
ACTION: Think of your company kick off more like an entertaining event than a boring meeting. Manage the agenda flow wisely. Mix up high energy sections with lower numbers-based sections. Then create a theme for the event (and the year). A rallying cry that everyone remembers and references throughout the next 12-months. Have it tie everything together. What’s the big thing you’re all trying to do this coming year?
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Don’t treat your company kick off like an afterthought.
When you start having “culture issues” mid-year, it could be a direct result of your shitty company kick off in January. Your team needs a shot in the arm of Purpose, Direction & Progress. This keeps everyone aligned and fired up for the year to come. Skip it at your own risk.
Till next time,
Never say die 🏴☠️
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P.S. Holy shit! We crossed 1,000 students in Highland Academy – the 100% self-service version of Highland. Since opening it up, we’ve had CEOs, executives and managers from around the world signing up!
See what all the hype is about. Start your own 7-day free trial right now. You literally have nothing to lose. And who knows, it might even make you a better leader!
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