The Most Important Question in Business and Life

About 12 years ago, my consulting firm helped a networking association put on an annual conference. The conference had started about 10 years earlier — before the Great Recession — and had been well received for years. But attendance had gradually declined, and despite our best efforts, that year's event drew its smallest crowd yet and lost money.

I was sitting with the organization's leadership, including its president, after the conference concluded. We were having a celebratory drink for a job well done when the conversation turned to next year's event and what we could do differently. A couple of us started throwing out ideas, lamenting how people's attitudes toward traditional conferences had changed since the recession.

It was at that point that one of the group's leaders, who had been quiet until then, finally spoke up.

"Wait a minute," he said.

"Why are we doing this?"

The organization's president and I looked at each other in stunned silence.

"Why are we doing this?" he repeated. "There's nothing that obligates us to have this conference. If we're losing money and it's no longer meeting the needs of our members, why would we do it again next year?"

We never held the conference again.

It turned out that wasn't a failure.

It was one of the smartest strategic decisions the organization ever made.

I've carried that lesson with me ever since. Whenever I find myself stuck — in business or in life — I start with the same question.

Why are we doing this?

For starters, it's an excellent heat check. It forces you to become more present in the moment and evaluate whether your decisions are actually moving you toward the outcome you want. It helps expose assumptions, identify wasted effort and catch mistakes before they become habits.

Perhaps most importantly, it reminds us that strategy isn't always deciding what to do. Sometimes, it's deciding what not to do.

The question also reminds us that time is our most valuable resource. Every decision to continue doing something simply because we've always done it is also a decision not to spend that same time, money and energy somewhere else. Asking "Why are we doing this?" forces you to make those tradeoffs consciously instead of by default.

It also keeps strategy front and center. The answer to "Why are we doing this?" should always connect to a larger purpose. It should support your mission, advance a meaningful goal or improve your organization in some tangible way. If it doesn't, that's valuable information.

Sometimes the most important realization isn't that your strategy needs to change.

It's that you don't actually have one.

Those moments are an invitation to step back, return to first principles and spend time thinking about what really matters—professionally or personally.

Most of all, "Why are we doing this?" becomes a lens through which you view the world. It encourages curiosity instead of routine, intentionality instead of momentum for momentum's sake. Sometimes the question leads you to improve what already exists.

Other times it leads you to ask a much more important question: Should we be doing this at all?

I've found that asking "Why are we doing this?" has made just about everything better — from solving complex business problems to something as ordinary as watering my plants. It reminds me to be intentional instead of automatic, thoughtful instead of reactive.

It's a remarkably simple question. But I've found it's one of the most powerful strategic tools we have — in business and in life.