The Why Behind the Why: What Most Entrepreneurs Get Wrong
Why Your Team Can't Tell You Why They Work Here
Most entrepreneurs I know can talk about what they do for hours.
Ask them why they do it, and the room gets quiet.
Not because they don't care. Most of them care deeply. But caring deeply and being able to articulate it simply are two very different things. And the gap between those two things is costing you more than you think.
The Why Doesn't Have to Be Grand
Here is something that took me a while to accept.
Your why doesn't have to be original. It doesn't have to be the most noble purpose anyone has ever heard. Tim put it well in a recent conversation: the why could be as simple as making a cupcake. What matters is not the uniqueness of it. What matters is whether everyone in your organization can see the higher calling inside it. The noble purpose. The greater good.
John Maxwell used to say that when you have clarity around the why, the how, and the what are not easy, but they are easier. That line has stuck with me. Because in my experience, most of the operational chaos inside a growing company is not actually an operational problem. It is a clarity problem. Teams grow arms and legs, chase opportunities, hold on to things they no longer need, and sprint toward goals nobody can quite articulate, because the why was never simple enough to act as a filter.
When the why is clear, the filter works. When it is fuzzy, everything feels equally important, and nothing gets the focus it deserves.
Why Entrepreneurs Avoid This Conversation
I get it. There is never a good time to stop and ask the big question.
You are delivering value. You are moving the ship forward. You are growing. And somewhere in the back of your mind, you know that if you really sit down and examine the why, you might have to kill something you worked incredibly hard to build. A product line. A market. A version of the company that made sense three years ago but doesn't anymore.
That is heavy. It is not a small ask.
But here is what I have seen happen to the entrepreneurs who keep running without stopping to examine it. They find themselves on a road to nowhere. Or they look up one day and realize their team cannot articulate the thing that is supposed to be driving all of them forward. And at that point, fixing it is much harder than it would have been if they had stopped to ask the question earlier.
The why is not a one-and-done exercise. It requires repetition, realignment, and a willingness to keep asking at every level of the organization. Why does this exist? Why are we doing this particular thing? Why does this activity ladder up to what we are actually trying to build?
Five levels deep. Every time.
Don't Dismiss the Naysayers
This is something I want to sit with for a moment, because I think entrepreneurs get this wrong.
Every organization has skeptics. People who push back, who ask uncomfortable questions, who refuse to just get excited along with everyone else. The temptation is to dismiss them as obstacles. People who don't share the vision. People who need to get on board or get out.
That is a mistake.
The naysayers are the ones God has placed in your orbit to point out the potholes. When your enthusiasm is running high, and your glass is not just half full but overflowing, they are the ones asking how. And that question, asked honestly, is not a threat to your vision. It is what sharpens it into something real.
Welcome them. Give them a seat. Let their skepticism make your why more precise.
Seasons of Growth Are Dangerous
One more thing worth naming directly.
When things are going well, when you are growing, when the momentum is there, it is actually harder to do this work. Not easier. The pressure to define the why is less acute when the numbers are moving in the right direction. So you keep running. And running. And the why gets softer and softer until it is barely there at all.
The entrepreneurs who do this well are the ones who build the discipline to examine the why, regardless of the season. Not because they are in crisis, but because they know a season is coming when they will need to know it with precision. And you do not want to be trying to find the essence of what you are uniquely built to do when you are under pressure to survive.
Do it now. While you have the space.
Try This Today
Take the most important thing your team is working on right now and ask why five levels deep. Write down the answers. If any level produces a complicated answer, that is your problem to solve. The goal is simple: aligned answers all the way through. If you can not get there, you have found the work.
- Nick Madden
CEO, SENT
At SENT, this is some of the most important work we do with members. If you are an entrepreneur trying to get to the bottom of your why, we would love to be part of that conversation.
