Why Strategy So Often Fails And What Leaders Can Do About It
Every leadership team wants its strategy to succeed.
The hours of debate, the offsite workshops, the carefully worded vision statement – all of it is meant to set the organization on a winning path.
And yet, most strategies don’t quite land as intended. Some stall quickly. Others lose momentum slowly, fading into the background as daily operations take over.
Why does this happen so often?
One reason is that leaders tend to focus on the bright side of strategy – the inspiring success stories, the bold bets that worked. But if you only study success, you miss the deeper lessons. Failure, uncomfortable as it is, often teaches us more.
Why failure is the better teacher
Think about your own career for a moment. Which moments taught you more – the projects that went exactly to plan, or the ones that went sideways?
Most leaders will admit it: the hard lessons, the mistakes, the setbacks, are what shaped their judgment. Yet when it comes to strategy, we tend to bury failure.
Annual reports highlight the wins. Keynotes celebrate the bold bets that worked. Business school cases study the companies that got it right.
Meanwhile, the far more common outcome – a strategy that fizzled, drifted, or collapsed quietly – is rarely analyzed in public.
That’s a missed opportunity. Because if failure is the baseline, then studying it is the only way to improve the odds.
Strategy is not chess
Too often, strategy is portrayed like chess: study the board carefully, anticipate every move, execute with precision, and victory is assured.
But real-world strategy looks nothing like that. It’s closer to poker:
- You’re making decisions with incomplete information.
- You can make the “right” move and still lose to external factors.
- The best players win not by brilliance, but by avoiding the most common mistakes.
Executives who treat strategy like poker – a game of probabilities, not certainties – are the ones who consistently beat the odds.
Where strategies break down
In our work with B2B organizations, we’ve seen that most strategies fail in predictable places. Four stages in particular:
- Problem formulation – Leaders jump into solutions without agreeing on the real issue.
- Strategy development – Ambitions stay high-level because no one wants to make the painful trade-offs.
- Planning – Roadmaps balloon with dozens of initiatives, each competing for scarce time and resources.
- Execution – The day-to-day reality of the business swallows the strategy whole.
Sound familiar? These aren’t rare slip-ups. They’re recurring patterns.
Why leaders underestimate the odds of failure
When executives hear that most strategies fail, many think:
“Yes, but that won’t be us. We’ve got sharper people. We’ve got better insights. We’ll be in the successful minority.”
It’s a comforting thought. But it’s usually wrong.
Failure is not an unlucky outcome that only happens to weaker competitors. It’s built into the way most organizations design, plan, and execute strategy.
In other words: failure is systemic, not accidental.
Three shifts that improve your odds
1. Reframe the question
Instead of obsessing over “What does success look like?” ask “What usually causes failure in situations like this?”
That single shift forces teams to confront blind spots, biases, and inconvenient truths early.
2. Think in portfolios, not silver bullets
Every major strategy is really a portfolio of bets. Some will flop. Some will pay off big. The point isn’t to avoid failure altogether – it’s to ensure the wins outweigh the losses, and to double down quickly when traction appears.
3. Make failure discussable
In too many organizations, raising early signs of trouble feels risky. Teams downplay bad news. Leaders double down on weak initiatives to “give them more time.” The result? Small issues snowball.
The companies that learn fastest do the opposite. They normalize conversations about what isn’t working. They set “kill switches” for initiatives upfront. They treat failure not as embarrassment, but as useful data.
Why this matters now
Strategy is harder today than it was even a decade ago.
B2B buying is more complex, with multiple stakeholders and hybrid digital–physical journeys. Competitors can pivot faster. Regulation, technology, and customer expectations shift constantly.
That makes the old playbook – annual strategy retreats, long static plans, vague growth slogans – dangerously out of touch.
In this environment, the companies that survive and thrive aren’t those with the flashiest visions. They’re the ones that treat strategy as discipline: systematically eliminating failure risks while staying agile when reality shifts.
Closing thought
Strategy will always involve uncertainty. But uncertainty doesn’t mean helplessness.
By studying where strategies fail – and designing deliberately against those failure modes – leaders can radically improve their odds of success.
In our latest white paper, we outline 32 recurring sources of failure that derail strategies, and how to build systems that counter them. If you’ve ever felt your strategy was strong on paper but fragile in practice, it’s worth exploring.
Written by Sixten Schultz, Jonathan Bellinger, and Leonie Schröder
