Annual Planning Amid Uncertainty: 4 Things Every Entrepreneur Needs
Annual Planning
There are only a handful of topics I hit with this newsletter every year, and Annual Planning is at the top of the list (although our holiday Elf Yourself videos are up there as well).
Once a year, you have dedicated time and space to step back, think about where you’ve been, and decide where you’re going for the next 12 months.
The decisions you make during Annual Planning, along with your ability to execute on them effectively, are critical to whether you succeed or fail in the coming year.
If you aren’t already doing Annual Planning…look, please just give me a call ASAP. I mean that. We are a Help First company, and we can at minimum have a consultant walk you through a framework for running your first Annual Planning meeting.
But if you are accustomed to Annual Planning, then I don’t need to rehash all the core best practices (although you can find them here).
Instead, let’s talk specifically about annual planning in this, the chaotic, AI-fueled, uncertain landscape of late 2026, as you think about 2027.
Four Areas to Emphasize During Annual Planning Sessions
1.) Risk
Every leader who has ever been in a SWOT analysis has spent time talking about risk. Though, to be fair, risk is a topic many of us prefer to avoid. It’s easier to bury your head in the sand, wait for things to improve on their own, and pretend you don’t see the problems right in front of you.
Not gonna fly this year. There is likely some risk to your business—changes in your competitive set, commoditization of your service because of AI, diminishing returns on marketing spend, a vulnerable supply chain, the instability of an election year…need I go on?
Many companies right now are operating on tighter margins with less room for error. They can’t afford to ignore their risks, and they can’t “wait and see” which way the wind will blow. Acknowledging risks head-on, and at minimum building contingency plans should the need arise, is more important than ever.
2.) AI
I know you’re already talking about AI ad nauseum, but I can almost guarantee that one of your goals for the year should be related to AI. Specifically, what your business is doing about it. You could be doubling down on your human capabilities, building AI add-ons into your offering, adjusting your messaging to meet the moment, or building the next great AI-enabled widget that we all don’t know we desperately need yet. But in some way, AI will inform the trajectory of your business in 2027.
I like John Sanei’s Defend/Extend/Upend paradigm for thinking about AI. You can find more on that here. In general, you should already be exploring, and ideally standardizing, how AI can improve efficiency in your business. Not every company is AI-first, but I’ve yet to work with a client who isn’t moving toward being at least AI-enabled.
3.) Focus
I’ve probably written this at least a dozen times over the years. My most successful clients set the fewest goals. 1-3 top priorities for the entire year, including our client who was recently acquired by a Fortune 500 company (yes, there’s a connection). Strategically selected, relentlessly executed.
One of our Guiding Principles at Crews & co. is: Keep It Simple. You and your team are not the exception to this rule. The more focused you are when setting your goals for the year, the more disciplined you can be about achieving them.
4.) Pre-planning
Planning before you plan is already a tenet of the Annual Planning process. You shouldn’t walk into an Annual Planning session expecting a brainstorm. So why call it out again for this year?
Because #1-3 on this list are going to ask a lot of you. You’re going to need your critical thinking skills, your entrepreneurial spirit, and a ruthless internal editor to accomplish them. You’ll be making choices amid uncertainty, and decisions that don’t have guarantees. All that takes brains, heart, and guts—and no small amount of courage, because you will be afraid.
Contend with all that when you sit down with your leadership team to map out the next four quarters? No thank you. This year, I implore you to pre-plan for Annual Planning. Get the information you need: take a look at what your competitors are doing, research the latest AI capabilities. Then schedule a Think Session or two to really connect with yourself, and what you want for the business, what opportunities you have and what might get in the way.
Your one-year-older-and-definitely-wiser future self will thank you for it.
