Why Most B2B Tech "Strategies" Fail (And How to Fix Yours)
Every year, as planning season kicks off, B2B tech leaders flood boardrooms with extensive decks outlining ambitious growth goals, market opportunities, and tactical roadmaps. Yet, despite all the effort, a familiar gap emerges when the conversation shifts from what they want to achieve to how they’ll win.
This is where most strategies falter. Companies often mistake a vision statement and a list of tactical initiatives for a real strategy. They define outcomes and activities but skip the critical part: how they'll outmaneuver competitors in their specific market.
It's a dilemma playing out across the industry right now, especially with funding becoming more selective and competition fiercer than ever. So, what separates a winning strategy from just another PowerPoint deck?
On our recent Marketing Execution Podcast, I broke down Jason Cohen's six-pillar framework, a proven approach helping tech companies bridge this gap. These principles turn strategic theory into actionable plans that drive results.
What Is Strategy, Really?
Real strategy answers one simple question: How will we win?
That's it. Not what you hope to achieve. Not a list of tasks. But a clear, decisive framework that explains exactly how your company will succeed in a competitive landscape.
Cohen's framework identifies six essential characteristics of great strategy. As you read through them, I invite you to mentally score your strategy against each one.
The Six Pillars Every Winning Strategy Needs
1. Simplicity That Clarifies Complexity
A strategy that tries to address everything ultimately accomplishes nothing. The most powerful strategies strip away complexity to reveal the essential core that drives success.
Look at Stripe's strategic foundation: "Increase the GDP of the internet." This concise statement guides complex decisions across their entire business. Engineers building payment infrastructure, sales teams targeting new markets, and product managers prioritizing features all understand how their work connects to this core strategic idea.
The power lies in the filtering function: When faced with multiple opportunities, Stripe's teams can quickly determine which options best serve their mission of increasing internet commerce.
Quick Test: If you stopped five random employees in your hallway, would they all articulate the same core strategy? Can your strategy fit on a Post-it note while still providing meaningful direction?
2. Candor About Brutal Realities
The market doesn't care about your feelings. Strategic candor means staring unflinchingly at the most frightening truths about your company and then building them directly into your strategy.
Generic concerns like "competitors might build a similar product" reveal nothing. Real strategic candor identifies specific, data-backed threats already affecting your business. Perhaps your user engagement metrics show that even paying customers don't value core features. Maybe your sales cycle has lengthened by 40% in the last six months. Or your once-dominant market position is eroding at an accelerating rate.
When organizations acknowledge brutal facts, they create space for solving them. Those who avoid uncomfortable truths eventually get blindsided by them.
Quick Test: Does your strategy document contain specific, measurable challenges that make stakeholders uncomfortable? Does it name the elephants in the room that everyone privately worries about?
3. Decisiveness Through Clear Choices
The essence of strategy isn't what you choose to do; it's what you deliberately choose not to do. Most "strategies" fail precisely because they attempt to pursue every opportunity rather than making the hard choices that create focus.
Cohen offers a razor-sharp test for strategic decisions: The "Opposite Test." If the opposite of your choice isn't also a viable option that some successful companies might choose, then it's not a strategic decision. "Being customer-focused" fails this test because no company would choose to be "customer-hostile." However, "offering high-touch premium service at premium prices" passes because some companies successfully choose "providing self-service affordability at lower margins."
True strategic choices create consequences you must willingly accept. When you target enterprise clients, you'll inevitably attract SMB customers who will request features you won't build. Your strategy should explicitly acknowledge these tradeoffs so teams remain aligned when these scenarios arise.
Quick Test: Can you name five significant opportunities you've intentionally declined despite their apparent value? Does your strategy document anticipate and accept the negative consequences of your strategic choices?
4. Leverage Through Amplifying Strengths
Mediocrity comes from trying to fix weaknesses. Greatness emerges when you double down on distinctive strengths until they become insurmountable advantages.
Consider Zappos in its early days facing an impossible challenge: convince people to buy shoes online without trying them on first. Instead of attempting marginally better product photography, they created a system of interlocking strengths: a 364-day return policy, customer support representatives empowered to go to extraordinary lengths, and a corporate culture that turned service into competitive weaponry.
This approach didn't just address customer hesitation; it redefined the entire shopping experience. By amplifying their service excellence rather than fighting the inherent limitations of online shoe shopping, they built a billion-dollar business that Amazon eventually acquired.
Quick Test: Does your strategy primarily leverage distinctive strengths your company already possesses? Or does it depend on successfully developing capabilities you currently lack?
5. Asymmetric Opportunities for Outsized Results
The best strategic moves create situations where potential gains dwarf possible losses. Cohen uses the sailboat analogy: a well-designed sailboat moves forward regardless of wind direction because of its asymmetric design. Great strategy functions the same way.
This principle manifests in creating a portfolio of initiatives where upside vastly outweighs downside. Amazon exemplifies this approach through Jeff Bezos' philosophy: "If you're going to take bold bets, they're going to be experiments... A few big successes compensate for dozens of things that didn't work."
This isn't recklessness—it's mathematical intelligence. When you structure initiatives so that successes create disproportionately more value than failures destroy, you build inevitable forward momentum into your strategy.
Quick Test: If half your strategic initiatives failed completely, would the remaining successes still create enough value to achieve your objectives? Have you structured bets with limited downside but substantial upside potential?
6. Long-Term Competitive Advantage
The difference between tactics and strategy is time horizon. Building features customers request is tactical. Creating capabilities that secure your market position for years is strategic.
Google's acquisition of YouTube demonstrates this perfectly. They established a goal of one billion daily views when such scale seemed unimaginable. Their analysis revealed that internet capacity at the time couldn't support this ambition, so they invested billions in global network infrastructure years before immediate needs required it.
Without this long-term perspective, Google might have optimized for short-term metrics. By investing against future scenarios rather than current conditions, they created a video distribution platform that competitors still haven't matched a decade later.
Quick Test: Does your strategy explain not just how you'll win today but how you'll maintain a competitive advantage three years from now? Are you investing in capabilities that won't pay off until future years?
Signs Your Strategy Won't Deliver Results
After analyzing hundreds of strategy documents, we've identified these telltale warning signs that your "strategy" is just wishful thinking:
? Excessive Complexity: The strategy contains so much detail that no one can recall its key points. Documents running dozens of pages or presentations with hundreds of slides often indicate an absence of strategic clarity.
? Avoiding Uncomfortable Truths: The strategy glosses over genuine market challenges or competitive threats. It paints an unrealistically positive picture rather than confronting harsh realities.
? Reluctance to Make Trade-offs: The strategy attempts to pursue every opportunity rather than making clear choices about what to prioritize and what to ignore. It fails to specify what you'll deliberately say "no" to.
? Focus on Fixing Weaknesses: Instead of leveraging distinctive strengths, the strategy concentrates on improving areas where you're behind competitors. This approach typically yields mediocrity rather than excellence.
? Perfect-World Planning: Success requires everything to go exactly according to plan with no allowance for setbacks or changing market conditions. There's no resilience built into the strategy.
? Quarterly Mindset: The strategy prioritizes immediate results over building a durable advantage. It focuses exclusively on the coming months rather than establishing a foundation for years of success.
Put Cohen's Framework Into Action Now
After sharing these concepts with tech founders, I've seen immediate shifts in strategic thinking. Here's a practical approach to transform your strategy this week:
1. Conduct a Brutal Self-Assessment
Set aside 90 minutes with your leadership team. Rate your current strategy against each pillar using specific evidence, not gut feeling. Where most companies score themselves 8/10 on decisiveness, objective assessment typically reveals 4/10 at best.
2. Identify Your Strategic Blind Spots
For your two lowest-scoring pillars, list concrete examples of the symptoms. Are you pursuing too many "strategic" initiatives simultaneously? Do board presentations gloss over emerging competitive threats? These patterns reveal your strategic vulnerabilities.
3. Reframe Leadership Conversations
In your next executive meeting, introduce the underperforming pillars as discussion topics. Example: "Our strategy lacks asymmetry. Here are three opportunities where we could create outsized returns relative to investment. Which should we prioritize?"
4. Create a One-Page Strategy Reset
Forget 50-page strategy documents. Craft a single page addressing each pillar with specific commitments. Under "Decisiveness," you might write: "We will focus exclusively on the enterprise healthcare vertical through 2023, declining opportunities in adjacent markets."
Cohen emphasizes that "a mediocre strategy that's actually used is better than a perfect strategy that sits in a drawer." Start with these practical steps this week rather than waiting for the perfect strategic revelation.
Listen Now: The Strategy Framework That's Changing B2B Tech
Want to hear a deeper analysis of these six pillars, including specific implementation stories from tech companies that have transformed their approach? Listen to the full episode here.
Your Turn: What's Your Strategic Challenge?
Now I'm curious: Which of these six pillars presents the biggest challenge in your organization? Have you seen a specific strategic shift that dramatically improved results? Your insights could help others in our community tackle similar challenges.