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Seven Ways Strategy Goes Wrong

More often than not, investments in strategy pay huge dividends to teams, senior leaders, customers, and funders. But there have been times when that’s not the case.


Years ago, I was invited to participate in a weeklong strategy conference for a team of senior leaders invited from all over the world. Impressive titles, big ambitions, real energy in the room. But something was off. I raised concerns on day two: there had been little discovery, prep work, or competitive analysis prior to jumping into strategy development, and no honest answer to the hardest question: What makes this team irreplaceable? 


The final strategy was published and launched with much fanfare, but it was dangerously generic. Within a year, the team was dissolved.


The strategy hadn't failed at execution. It had failed to identify what made the team worth continuing to fund and support (aka, Strategic Differentiators… more on this in a future blog).


To get strategy right, it’s essential to have a firm grasp not only on what works, but what doesn’t.


The Research is Clear (but... uncomfortable)

Harvard Business Review reports that 67% of strategies fail. Kaplan and Norton put it even higher: up to 90% of strategies are never successfully executed. For mission-driven organizations, the stakes are even greater, because failure isn't just organizational, it's a setback for the people and causes they serve.


Here's what research (and, frankly, lived experience) tells us about why strategies fail:


1. No clear differentiator. If you can't answer "Why us, and not someone else?" neither can your funders, your board, or your team.

2. Strategy lives in a document, not the work. Most plans are vague, complex, and nearly impossible to execute. Boards feel good making them. Frontline staff are left wondering what any of it means for Monday morning (if the strategy was shared at all).

3. No way to measure what matters. Without impact measurement, you can't prove value to donors, to leadership, or to the people you serve. Most donors look for impact evidence before giving.

4. Financial fragility. Even a brilliant strategy collapses without resources aligned to priorities. Good intentions don't pay for program delivery.

5. Leaders who aren't actually behind it. When leaders lack genuine conviction in the strategy, it arrives dead on arrival. You can feel it in a room.

6. Culture that wasn't ready. A team can have the best strategy on paper and still fail if the culture doesn't support it. Misalignment, low trust, or even one or two individuals quietly corroding momentum can stop execution cold.

7. People were excluded from the process. When strategy is handed down rather than built together, you get compliance at best and quiet resistance at worst.


The Good News

These are solvable problems. None of them require a bigger budget or a longer planning retreat. They require honest assessments, a proven strategy development framework, inclusion, and a willingness to ask the harder questions before the week is over.


Research Sources

 

 

 

 
 
 

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