Why 80% of strategy retreats fail
You can’t pull what isn’t there out of your executives’ heads
When running strategy retreats, leaders expect a sudden explosion of openness and creativity. They think that if they drag the team away from the office and lock them in a room without phones or laptops, brilliant ideas will just pour out like a fountain.
Sadly, good ideas are usually in short supply. Does this sound familiar?
Creativity isn’t a cactus—it won’t grow in a desert. You have to cultivate the right environment for it to thrive.
Inside the Club today:
1. Brainwasting – why brainstorming doesn’t work
2. Why we’re looking for the wrong elephant in the room
3. Strategic retreats done right
4. CEO Uncomfortable Questions
Brainwasting
“Sua… Sva… Sla…”
The man on my laptop screen is struggling with my Slavic name. I get it. For most people on planet Earth, pronouncing it is a challenge. But my mother loved her father—my grandfather—dearly, so she named me after him.
“It sounds like Svyatoslav,” I say with a smile. “But please, don’t worry about it. I know it’s a toung-twister. Some days, even my wife struggles with it.” The man smiles back. “Just call me S.B.”
“Deal!” he says, looking relieved. “So, S.B., we’d like to invite you to facilitate our strategy retreat. We want a big brainstorming session about our future strategy.”
“Hmm,” I reply. “When do you want to do this?”
“How about next month?”
“Hmm,” I say again. “It’s not just about my schedule. I’m afraid one month isn’t enough to prepare your team for a strategy discussion. And tell me—why are you talking about brainstorming?”
He looks surprised. “I thought we were ready. We know the numbers, we watch our competitors. Our marketing team sends out a market insight memo every month. Besides, isn’t brainstorming the best way to get new ideas?”
“That’s good, but it’s not enough. You can hold a retreat without the most important data, but I wouldn’t recommend it. It’s a waste of time and money. And brainstorming? It’s a very bad method for generating ideas.”
“Bad?”
Don’t whistle indoors!
The history of science is packed with “zombie theories”—ideas that were debunked ages ago but still roam the halls of our minds. Take Maslow’s hierarchy of needs, the 10,000-step rule, the myth that habits form in 21 days, or the brainstorming session.
My grandmother believed that whistling indoors would blow all your money away.
God has a wicked sense of humor. Some amateur comes up with a theory, professionals prove it’s nonsense, and yet it stays stuck in our heads like a Last Christmas song.
That’s exactly what happened with brainstorming. Alex Osborn, a co-founder of the legendary ad agency BBDO, cooked it up in the 1930s. He wrote a book called Your Creative Power.
(If he’d seen the royalty checks Simon Sinek or Jim Collins pull in today, he would’ve ditched the ad business to become a full-time guru.)
The first doubts appeared as early as 1958. Since then, scientists have proven time and again that reports of brainstorming’s effectiveness are greatly exaggerated.
I ran my first brainstorming session back in 2004. I was a young, green CEO looking for breakthrough strategic ideas to drive our business forward.
We tripped over every classic hurdle:
The loudest voices dominated. Brainstorming is like a bazaar—the person shouting the most isn’t necessarily selling the best goods.
The “no criticism” rule is easy to declare but difficult to enforce. Just because you’re sitting in a circle in a hotel conference room doesn’t mean your boss stopped being your boss.
The larger the group, the lower the individual effort (the so-called Ringelmann effect).
The more Post-it notes we stuck on the wall, the more complacent we felt. We didn’t realize we’d fallen into yet another trap: brainstorming sessions often yield a high volume of low-quality ideas. Five dollars in pennies may look like a fortune, but it doesn’t make you rich.
And the irony? We were so busy looking for the ‘elephant in the room’ that we missed a whole herd of elephants grazing nearby, just out of sight. Since I moved from the CEO’s chair to becoming a strategy advisor, I’ve realized that many business leaders are experts at ‘missing the herd.’
The herd of elephants
Many CEOs still believe strategy is about finding the best path through the market’s stormy seas. But that’s like Hansel and Gretel trying to find their way home by following someone else’s breadcrumbs.
We’ve covered this before—for example, here and here.
As a quick refresher, here are the two core pillars of The Customer-Axis Framework:
There is only one way to build a successful business: first, create a customer; second, establish Customer Value as the axis for every process, asset, and decision.
Creating your own customers—Patrons—allows a company to transcend competition and focus entirely on its own evolution.
Searching for the “elephant in the room” during a strategic retreat usually turns into a debate about internal headaches—excessive bureaucracy, the cash conversion cycle, or why the coffee machine is always broken.
But the real “herd of elephants” is roaming outside. These are your non-customers, and you probably know far less about them than you think.
Plants don’t grow by watering themselves with their own juices. They need water from the outside, and so do businesses. And the source of the water? Your non-customers. These are the people who can become your future customers and, eventually, your Patrons.
Non-customers—your future clients—should be the star of the show at your strategy retreat. Forget the “business model” or debating who is the most toxic person on the team.
But talk is cheap. You need to know these non-customers better than you know your old college buddies. That’s why I use a different playbook for retreats —and the results are something I’m genuinely proud of.
My playbook for strategic retreats
80% of a strategy retreat’s success is decided before you even book the conference room—it’s all about the preparation. We touched on this briefly last week.
Proper preparation usually takes one to two months. During this time, every top executive and key expert must have at least 4–5 online conversations with potential customers. They also need to meet them twice in their “natural habitat” to see how they actually live and work. We arm them with custom interview guides and run a quick briefing before the work begins.
We analyze competitors and scout business models in adjacent industries. But we don’t do this for the sake of “market analysis”—because, as we’ve established, “the market” doesn’t actually exist. Our goal is to soak leaders in context and wake up their creativity.
There are endless books on the nature of creativity, but they all share one core thought: you can only be creative if your brain is a well-stocked “library” of data. To “connect the dots,” you first need to have enough dots to work with.
During the prep phase, we pack the participants’ mental libraries with as much information as possible. But we couldn’t care less about the company’s last year’s wins or losses. We care about the outside world—the reality that is usually invisible from behind a comfortable office desk.
I never use brainstorming, only its smarter alternative—brainwriting. I use group discussions to debate ideas, not to hunt for them.
When the ideas run dry, we switch to structured scenarios. Experience shows that people are surprisingly bad at generating ideas without a script.
My favorite scenarios:
Foresight games (like the Futures Wheel or the Four Horizons).
Lateral Marketing—stripping your core products down to their basic parts and rebuilding them from scratch.
TRIZ—the “Theory of Inventive Problem Solving,” a unique Soviet method for finding non-standard solutions to “impossible” problems.
Design thinking
But no amount of clever techniques can pull something out of your team’s heads that isn’t there to begin with. That is why preparation remains the most critical part of any retreat.
My schedule for the first half of 2026 is filling up fast. If you want your next strategy off-site to be a turning point rather than just another hotel dinner, drop me a line. If the chemistry is right, we’ll find a way to make it happen.
CEO uncomfortable questions
Are you actually tackling the issues that matter at your strategy retreats—or just rearranging the deck chairs?
Is everyone in the room—including HR, Finance, and Logistics—ready to talk about the customer?
Are you giving your preparation the time it deserves, or are you just winging it?
If your last retreat fell flat, what exactly are you changing this time to avoid a repeat?
Conclusion
You certainly have internal ‘elephants’ too. But you don’t need a fancy retreat to talk about them—handle those today.
If you insist on heading off-site to talk about the things that actually matter, keep your agenda down to just three questions:
Which Big Customer Problem are we going to solve?
What Unique Customer Value will we offer?
How, specifically, are we going to make it happen?
Keep it simple. Your team (and your ROI) will thank you.
Next Tuesday, we’ll dive into the "hidden leaks" in your business—and how to fix them using the Growth Metabolism approach. Stay tuned!
Svyatoslav (S.B.) Biryulin
Just a reminder: upgrading to a paid subscription pays for itself. Last week, my paid members received a complimentary guide on cost-cutting through a process-driven approach. If you aren’t ready to subscribe yet, you can still buy your copy here.
Loved this one S.B :)
I find that leadership teams use brainstorming sessions to get input from others that they can't (or are too lazy to) generate themselves. Let's see what everyone else comes up with. This is why structured prep makes a huge difference. It will be apparent to everyone when a few members of the team arrive unprepared to fully contribute.