Annual Planning Amid Uncertainty: Feel Your Way Back to the Light

It’s annual planning season.
And right now, some business leaders feel like their annual plan looks like this:
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Been there? Me too.
Is annual planning still relevant when every day, you seem to wake up in a different landscape? Like things have transformed overnight while you were sleeping?
Yes. I think so.
But planning is different now, no doubt about it. If you want to plan effectively for 2026 and beyond, you have to come to terms with that fact.
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AI is obviously a huge disruptor that is making future planning extremely difficult right now.
The questions about AI go well beyond, “How can we use AI to create efficiencies in our business?” and “How could AI augment our offerings or improve our margins?”
Those are the table stakes conversations. The bigger questions are more existential:
- How could AI impact our business model and pricing?
- Will AI commoditize our offering in the market?
- How fast will these changes happen, and how long do I have to prepare?
(If you haven’t read it, I suggest revisiting my newsletter on the extend/defend/upend approach to thinking about AI.)
Even at Crews & co., AI has forced us to ask questions like: “Who are we? What do we really do for a living? Where do we provide the most value for our clients?”
I’m not too proud to admit that an advanced GPT of Eric Crews that was basically a download of my brain could go a long way in giving companies sound advice. What gen AI can’t do right now is build trust, create accountability, and navigate company dynamics in a way that ensures businesses set the right goals and put in the work to get them done.
So with that theory of the case, we are anticipating how AI may affect the coaching and consulting industry at large. And we’re placing bets and making assumptions accordingly.
Yes, these are assumptions. Yours will be too. Because in a time of uncertainty, you have to live in the messy middle.
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There are plenty of other factors creating uncertainty and instability right now; I bring up AI specifically because it seems to be the most universal across our client base.
So here’s the thing. If the future is opaque, how do you build a plan for it?
What you will need most is resilience. You’ll need the ability to respond quickly as new developments, recover from unanticipated losses, and pivot into unexpected opportunities.
That last point shouldn’t be overlooked: uncertainty always creates opportunity for some. Usually, the ones who are taking action, even if they’re moving ahead with imperfect data, clinging only to the few facts they know.
The majority who decide to “wait and see” and don’t adjust their trajectory? They’re the least likely to turn the potential of an uncertain moment into opportunity.
Lately, this image keeps popping into my head. I’m in a dark closet, so dark I can’t see a thing. I’m trying to feel my way through to the exit.
If I panic and thrash around, I stay locked in the closet. If I close my eyes and pretend I’m somewhere else, same outcome.
But if I calmly, slowly, tune into the environment around me, I can make some progress. I can feel the clothes on their hangers, the shoe rack on the floor, the tennis racket resting against the corner.
I can feel the seam of the door and eventually…the knob that will spill me back out into the light.
There’s an old saying of mine (according to me): be specific when you can be, and general when you can’t be.
Now might be a moment when your plan for the future needs to be more general than specific. That’s okay.
Keep feeling your way forward.
PS - If you need help figuring out how general or specific your annual plan should be, contact us here.