The Most Useful Question Is Often the Awkward One
I sat down with a business owner who was three months into a new venture. He was still finding his feet, making decisions about where to spend his time, and working out what he needed to say no to. That is a familiar stage of building a business: there is plenty to do, plenty to learn, and no shortage of things that look important. What stayed with me was what he wanted from our conversation. He did not want reassurance. He wanted to know what he could not see yet. Reassurance might have made him feel better about the decisions he was making; understanding a blind spot could help him make the next decision differently.
Nick Clift
9/18/20263 min read
I sat down with a business owner who was three months into a new venture. He was still finding his feet, making decisions about where to spend his time, and working out what he needed to say no to. That is a familiar stage of building a business: there is plenty to do, plenty to learn, and no shortage of things that look important.
What stayed with me was what he wanted from our conversation. He did not want reassurance. He wanted to know what he could not see yet. Reassurance might have made him feel better about the decisions he was making; understanding a blind spot could help him make the next decision differently.
When you are busy getting a venture off the ground, looking for problems can feel like a strange use of time. Surely there are enough already? But there is a difference between creating unnecessary worry and being curious about what might be missing. The owner was not asking someone to list everything that could possibly go wrong. He wanted another perspective on the business he was trying to build.
That is a sensible instinct. We do not have to wait until a problem becomes urgent before giving it our attention. Sometimes a calm conversation now is more useful than a frantic conversation later.
Looking for a blind spot is not a sign that you lack confidence. It can be a sign that you are willing to learn. That willingness matters at the beginning of a business, and it matters just as much after years of running one.
An established business comes with history. There are reasons for the way clients are handled, the way work is passed between people, and the way decisions are made. Often those reasons made perfect sense at the time. The difficulty is that a sensible decision can become a permanent habit without anyone revisiting it.
We keep doing something because we know why it started, but we do not always ask whether that reason still applies. After a while, explaining the history can become a substitute for examining the present. An outside perspective has value here, not because the person outside knows your business better than you do, but because they have not learned which questions everyone inside has stopped asking.
“What makes this necessary?” “Does this still fit the business you want to build?” Sometimes those questions reveal that nothing needs changing. That is useful too.
This is the approach I want to bring to my role as Governor of Growth at Morphability. Particularly in sales and operations, the first description of a problem is a starting point for a conversation, not necessarily the final explanation. Before discussing what to change, it helps to understand what is happening and why.
That does not require turning every issue into a lengthy investigation. Nor does it mean the owner has to defend every decision they have ever made. It means staying curious long enough to avoid rushing into an answer that feels tidy but does not quite fit.
The owner was also working out what to say no to. That deserves attention because an early business can become complicated remarkably quickly. Each opportunity may look reasonable on its own, but put them together and the business may start moving in several directions at once.
There is no prize for having the busiest calendar and the least clear idea of what matters. A useful growth conversation includes focus: does this opportunity fit, can the team deliver it sensibly, and is it helping build the business the owner actually wants? Those questions connect sales decisions to operational reality.
We all need encouragement at times. Running a business can be demanding, and there is nothing wrong with wanting someone to acknowledge a difficult week. But we also need conversations that go beyond encouragement: conversations with someone who will listen, challenge an assumption respectfully, and help explore an answer without making us feel foolish for not already knowing it.
You do not need to arrive with a polished explanation. “Something here does not feel quite right” can be enough to begin. What is one part of your business you would like someone to look at with fresh eyes, before it becomes the next urgent problem?