“Why are we doing this?”
It’s a small question, but one I’ve returned to constantly. In boardrooms, in backlogs, in strategy decks and stand-ups, it’s the question that has clarified more confusion than any framework or KPI ever could.
I’ve used it throughout my career not to obstruct momentum, but to ensure we’re doing the right thing at the right time, for the right reason. To check whether the project, process, direction, or decision we were about to build, fund, launch, or measure was still tied to the problem we thought we were solving.
And I’ve encouraged every team I’ve worked with to do the same. Ask why. Ask early. Ask even when the room is moving fast. Especially then.
Why is the most powerful question in business. It helps us uncover root causes: of actions, behaviors, breakdowns, and results. Whether I’m managing, coaching, selling, negotiating, or re-engineering, asking “why” is the fastest way to get underneath the surface and understand what’s actually driving things.
Not everyone welcomes the question. In some environments, it’s seen as friction. But I’ve found that the best work doesn’t come from people who are quick to say “yes.” It comes from people who pause long enough to ask, “Why this? Why now? Why this way?”
Asking “why” isn’t about slowing things down. It’s about making sure we’re moving in the right direction. It’s a simple guardrail against wasted effort and strategic drift. It keeps ego, inertia, and assumptions from quietly steering the ship.
Too often, people mistake a clear plan for a sound one. They inherit goals without revisiting the reasoning behind them. They chase metrics that once mattered, or adopt processes that no longer fit. Without “why,” it’s easy to look busy and still end up nowhere useful.
Sometimes the learning helps you repeat what worked. Sometimes it shows you what to avoid next time. Either way, the path forward starts with the courage to ask.
Of course, “why” can make people defensive. Some hear it as a challenge rather than an inquiry. That’s understandable. Many of us learned to guard ourselves against tough questions and to offer polished, partial answers rather than reveal the messy reasoning underneath.
But half-answers are rarely useful. Worse, they can be misleading. And when they go unchallenged, they prevent progress. You end up solving for symptoms, not causes. You move forward on shaky logic because no one was willing to slow down long enough to get real.
Sometimes, people avoid asking “why” not because they don’t care, but because they’re afraid of what the answer might reveal. About the idea. About the process. About themselves. That’s human. But clarity doesn’t come from avoidance. It comes from inquiry, even when the answers are uncomfortable.
So ask “why.” And if the answer is vague or incomplete, ask again. You may need to peel back a few layers. The first “why” reveals what someone thinks. The second starts to reveal what they believe. Ask a few more, and you’ll get to what actually drives the behavior or decision.
There’s a reason so many operational thinkers talk about the “Five Whys.” It’s not a magic number. It’s a mindset. One that refuses to accept surface-level explanations in place of genuine understanding.
A strong “why” is also an anchor. When a team has clarity on why something matters, they can better navigate the how, what, who, and where. Execution becomes easier. Tradeoffs become clearer. Even resistance becomes more manageable.
Some of the most productive conversations I’ve been part of didn’t start with a solution. They started with a thoughtful, sometimes quiet, “why?” Like: “Why are we prioritizing this now?” or “Why are we assuming that approach still makes sense?”
Used right, “why” doesn’t slow things down. It clears the fog. It sharpens decisions. It strengthens alignment. It’s not a power move. It’s a clarity move.
In fast-moving environments, clarity is an edge. And clarity rarely happens by accident. It comes from people willing to ask the one question that’s easiest to skip when things feel urgent: Why?