Don't Start With Why
Simon Sinek’s “Start With Why” is one of the most influential business ideas of the last decade. If you’ve been told to paint the vision first and work backward from there, to inspire people with the future before worrying about details, you’re following advice that sounds transformative but often paralyzes organizations in practice.
I tried this approach for years as a leader, believing deeply in it. What I discovered is that vision-only communication creates problems that aren’t obvious until you’ve lived through them long enough to recognize the pattern.
What I Watched Unfold
I worked in an organization with an ambitious vision: make technology investments demonstrably profitable for clients. It sounded inspiring in all-hands meetings, the kind of transformative goal that should energize people and align everyone toward building something meaningful.
As one of the leaders pushing this vision, I gave people the big picture constantly. The why. The transformative future we were building toward. Then I tried to help them get there, mostly with hypothetical instructions and abstract guidance about how to achieve something we’d never actually done before.
What unfolded over the next several years taught me something uncomfortable about vision-first thinking.
People who needed more structure couldn’t bridge the gap from abstract vision to concrete action. They started asking increasingly lost questions, proposing things like workshops to figure it out which just burned money without creating clarity. When your vision is too far from current reality, people who need clear direction just spin their wheels trying to generate ideas toward a hypothetical target.
But the strong performers, the ones I expected would thrive with this kind of big-picture thinking had it worse in a way that took me longer to recognize.
They did generate initiatives. Big, ambitious ones that all seemed aligned with the vision when you looked at them individually. The problem was that these initiatives often contradicted each other, and nobody could see it happening because the vision itself was too abstract to serve as a useful filter for decision-making.
Each initiative required engagement across different parts of the company. After several rounds of this, everyone was exhausted, including the top performers who’d been driving these efforts. And we had no measurable results to evaluate against the vision because you can’t really measure progress when your goal lives entirely in some future state.
Years of this. Same pattern repeating. No meaningful progress toward that inspiring vision we’d articulated so clearly.
What I Eventually Understood
When you start with the distant future, with the why before the what, you make everyone work in abstraction. The vision becomes what I now think of as corporate decoration. It’s beautiful to look at, inspiring to talk about in meetings, but fundamentally useless for making the hundreds of small decisions that actually move an organization forward.
If you’re weaker at your role, you don’t know what concrete actions align with this abstract vision, so you generate activity that feels vision-aligned but doesn’t actually go anywhere useful.
If you’re stronger, you generate initiatives that all sound right when you present them individually but end up contradicting each other in practice. You burn yourself out because big visionary goals seem to demand big exhausting initiatives, and because the vision is so far from your current reality, nothing ever feels like measurable progress.
The alternative isn’t abandoning vision entirely. It’s reversing the order you build from.
Start with something concrete, something you’ve actually done successfully, or something you have real evidence you can accomplish. Then build toward the bigger vision from there, using what you learn from those concrete wins to refine what the vision even means in practice.
This is closer to what Dave Snowden talks about with the Cynefin, or what Simon Wardley describes with his mapping approach. Both start with understanding your current context, what actually exists and works today, and then evolve from there rather than trying to work backward from some aspirational future state.
The difference isn’t just semantic. It’s practical in how it affects what people actually do.
Compare “Our vision is to make technology investments profitable” with “We successfully helped three clients measure real ROI on their technology investments. Let’s figure out how to do that for twenty more, then use what we learn to define what ‘profitable technology investments’ actually means at scale.”
The second version requires you to have those three wins first. You can’t start with abstraction. You start with concrete evidence of what’s possible, and build your vision from there.
What Actually Builds Momentum
If you’re leading with vision-first strategy, ask yourself one question before your next all-hands meeting where you’re planning to inspire people with the big picture: do you have concrete evidence this vision is actually reachable?
Not hypothetically. Actually. Have you done even a small version of what you’re describing successfully?
If the answer is no, you’re probably starting too far in the future. Find something smaller that you can point to as proof of concept. Start there: what’s actually working right now? What could you accomplish next quarter that’s concrete and measurable rather than aspirational?
I understand why “Start With Why” resonates with people. It sounds deeply inspiring, and the desire to give people meaning and purpose in their work is genuine and important.
But I’ve watched it create years of contradicting initiatives, exhausted teams who burned out chasing abstractions, and strategies that sounded transformative in presentations but never actually left the whiteboard.
The leaders I’ve seen actually make progress do it differently. They start with what’s real and proven in their current context, then build their vision from there rather than trying to work backward from some imagined future state.
That’s the order that actually works.