When it comes to strategy, we crave data and rigor.
In the search for answers, we get addicted to digging up more questions. The more questions we ask, the more rigorous we feel — optimistic that more data, discussion, or research will unlock the answer. The sure thing. The path forward.
I've seen leadership teams filled with the brightest minds — minds responsible for much of our digital world — sense a strategic decision on the horizon and begin to thrash, laying down on the tracks just to avoid an uncertain choice.
But the more information you dig up, the path just seems to disappear.
What we're really searching for in all that rigor and analysis is not necessarily a clear choice, but something more human.
The Bakery Example
Let's imagine you want to open a bakery.
You have to decide whether to invest your resources in cakes, cookies, french pastries, or something else. You could do all of these, of course, but that comes with its own set of headaches. At this point, a savvy founder will jump into the data and ask:
- What will sell?
- How many bakeries are there in my area?
- What are the highest margin products?
AI can get you pretty far with this research.
But there are still more questions to be answered:
- "What am I comfortable risking?"
- "What's my value proposition?"
And when the market questions run out, there are good internal ones:
- "What am I uniquely good at?"
- "What's my vision for the future of baking?"
And then what started as a strategy exercise takes a turn toward existential crisis:
- "What difference do I hope to make in the world through baking?"
- "Is baking really the impact I want to make?"
Then we freeze and lose hope.
In the search for strategy, we can get lost asking bigger and bigger questions until they become hopelessly unanswerable. We wade through research and define a point of view, hoping to glimpse a direction that carries a particular feeling of rightness.
In the search for data, what we're really after is confidence. Confidence that we have seen the future and know how it will turn out.
Even when we feel confident, most of the big decisions we make in life and business are inherently unpredictable. We can't know the answers.
3 Ways to Make a Strategic Choice
Research and data are valuable things. They help us make decisions much more effectively. I'd like to know if there's a 75% chance of rain when I head out in the morning, even if that doesn't end up being true — it gives me a reasonable boundary for the decision I need to make.
But what I see more often are executives who, believing they've predicted the weather accurately, are shocked and in denial when their plans fall apart upon bumping into reality.
So how do you know when you've gathered enough insight to get moving? How do you move forward in the face of uncertainty?
Here are three reframes that help you break a strategic gridlock.
1. Shrink the Risk
In most cases, the intensity of research gathering is directly proportional to the risk of doing the thing. The bigger the risk — financially or reputationally — the more we look for evidence to resolve the tension.
In the case of opening a bakery, signing a lease, building out a storefront, buying ovens and commercial-grade equipment — that's a risky bet. The wrong choices could prove financially fatal.
But the answer isn't more research. It's to reduce the risk to a point where the option would be foolish not to try.
Richard Branson famously started Virgin Atlantic Airlines against all advice. Instead of dropping millions on a fleet of new airliners, he rented a single used Boeing 747 from British Airways to get started. No one had ever asked to do that before.
Thinking this way requires creativity, patience, and a reframing of your goals.
Here are a couple examples:
- Big risk strategy: Find a space and build out a traditional bakery storefront. Research and data needed to decide the right location, size, equipment, staff, etc.
- Small risk strategy: Ask a local coffee shop if they'll carry your pastries for a couple of months to gauge the response.
The small-risk choice is so simple it almost seems like a waste of time. But if you can't sell pastries inside an established coffee shop, how can you do it full time in a store?
- Big risk strategy: Launch a design-forward rebrand of your classic chain restaurant — refurbished buildings, new swag, updated menus.
- Small risk strategy: Create a pop-up version of your new restaurant inside a warehouse and invite your most loyal customers to experience the new assets, menu, and feel.
The best strategy is the one that involves the most learning in the shortest period of time — not the one backed by the most research.
2. Add a Third Choice
The toughest choices we face often involve two doors — Door A and Door B. Right or wrong. This way or that way.
Major in finance or become a lawyer? Take the job that pays more but has a commute, or the one that pays less and is remote? Italian or Mexican for dinner?
Two options are always framed as a choice between winner and loser. And more than we like being right, we really hate being wrong. Our fear of being wrong is what makes a binary choice so difficult.
The solution? Add a third option. Choosing from three options allows us to let go and decide more freely, thanks to the psychology of loss aversion.
3. Remove a Variable
A freelance friend of mine was weighing whether to travel to a conference. He was stuck evaluating the return on investment. The conference was expensive, the hotels and flights were expensive, and the value of being in a room with other eager networkers was a big, fat unknown.
I asked him: "If the trip were free, would you be excited to go?"
"Oh yeah, that would be a no-brainer."
"Ok, so is there some way to reduce the cost to a point where it feels much easier to say yes?"
Pretty soon we had some ideas. He checked his credit card and found untapped airline points. He found more affordable hotels a little further from the venue. He decided he could stick to cheap dinners.
Does any of this make the ROI better? Who knows — you can't really know the ROI. What you can do is adjust a variable to a point where the prospect of a wasted trip feels much more tenable. By the end of our mini ideation session, he was even thinking about applying as a speaker the following year, which could make the ticket free.
The strategic choice is rarely about the choice itself. It's usually heavily dependent on one or two factors that, if different, would swing the whole decision.
Ready to try out a strengths-based strategy? Download the free Strategy Canvas to guide your next strategy meeting.
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