Leadership Conversations
Are you helping people think, or are you doing the thinking?
“Whoever asks the questions does the leading, because they set the context.”
John C. Maxwell
Business owners are often very good at solving problems.
That is one of the reasons they become business owners in the first place. They see gaps. They make decisions. They take responsibility. They find a way through when other people are still trying to understand the issue.
In business, that ability is valuable.
But in leadership, it can also become a blind spot.
In Peer Board conversations, and in coaching conversations with business owners, I often notice the same pattern. When someone brings a problem into the room, the natural instinct is to get to the answer as quickly as possible.
Find the gap → Offer the solution → Move on. At first, that feels efficient. It feels practical. It feels like the shortest route from problem to answer.
But fast answers often come from narrow questions. Narrow questions can close down the very thinking the person needs most. And I bet you’ll be asking those questions again in the near future.
Mindset: Your first answer is not always your best contribution
Business ownership teaches to decide, fix and move.
That is understandable if you’re an Owner carrying payroll, customers, suppliers, deadlines, cash flow and people issues, you cannot sit around theorising all day. Sometimes you need a clear decision and a strong hand on the steering wheel.
But not every leadership moment needs your fastest answer.
Sometimes the most useful thing you can do is not to solve the problem for someone. It is to help them understand the problem properly.
That requires a shift in mindset.
Instead of thinking, “ag come on, isn’t it obvious…?” the better reflection is, “What does this person still need to understand?”
That small shift changes the whole conversation.
When you jump straight to advice, you often give the person your answer based on your experience, your assumptions and your view of the situation. That may be useful, but it may also miss what is really going on and you’ll never be free of the mantle of problem solver.
You’ll always be the go-to person. A bottleneck.
An employee might, “I don’t know how to do this.”
The quick answer might be, “Pull this report, check that number and call that person.”
But a better question might reveal that the real issue is unclear standards, poor follow-up, weak accountability, low confidence, or a manager who avoids difficult conversations.
The first answer may be practical. Better question gets closer to the truth, solving problems for the long term.
Exasperated, Owners and Managers tell me, “but I don’t have the time for that! The deadlines will be missed! I’ll just do it myself” – I can literally feel their blood pressure rise …
“Uh huh …. How’s that working for you?”
Skill Set: Learn to ask questions that open the conversation
Business owners often ask direct, leading or closed questions.
Direct questions sound like:
“What is the problem?”
“Who did it?”
“Why not?”
Subconsciously these cause anxiety and trigger defensiveness.
Leading questions sound like:
“Don’t you think this is really a sales issue?”
“Isn’t this just poor timing?”
“Shouldn’t you replace the part?”
You’ve given the answer and disguised it as a smart question (guess what it’s not).
Closed questions sound like:
“Have you checked?”
“Are the parts in assembly?”
“Did you try switching off and on again?”
Yes / No answers don’t leave much room for growth.
These questions are not wrong.
There is a place for them. Sometimes you do need facts. Sometimes you do need clarity. Sometimes a simple yes or no is enough.
The problem is when these become the default and your people know that you will be their personal ChatGPT assistant.
Direct, leading and closed questions often steer the person toward the answer already sitting in your mind. You are not really exploring anymore. You are guiding them toward your conclusion.
Coaching questions work differently.
They create space.
They help the person slow down, look again, and think more clearly.
A good question opens up context, assumptions, root causes, options, consequences and ownership.
Instead of asking, “Why don’t you just delegate to someone?” ask:
“What are you struggling with?”
Instead of asking, “Is production the problem?” ask:
“Where is the pressure showing up most in the business right now?”
Instead of asking, “Have you spoken to them?” ask:
“What conversation are you avoiding?”
These are not softer questions. They are sharper questions. They go beneath the first layer of the problem. They deal with the person, not the problem.
We play the man, not the ball.
Open questions create ownership because the person must think. They cannot simply agree or disagree with you. They must reflect, name what is happening, and start making sense of the issue for themselves.
That is where better decisions begin.
Activity: Practise slowing the answer down
I had a manager tell me this week she was super proud of herself for being patient. She tasked an employee to figure something out for themselves, and 3 excruciating hours later they came back with a solution.
Better questioning is not something most business owners learn naturally. Business rewards action. It rewards decisiveness. It rewards speed.
So the habit of asking better questions has to be practised deliberately.
One useful exercise is simple:
In your next leadership conversation, before giving advice, ask three open questions.
Not statements dressed up as questions.
Not advice with a question mark at the end.
Real questions.
Try:
“What makes this issue important now?”
“What have you already considered?”
“What are you seeing that I may not be seeing?”
“What pattern is repeating here?”
“What would happen if you did nothing?”
“What decision would move this forward?”
“What support do you need, and what part must you own?”
These questions increase accountability.
Because when someone must think properly, they also must take more responsibility for what they see, what they avoid, and what they choose next.
That is useful in a Peer Advisory Board.
It is useful in a management meeting.
It is useful with a senior team member who keeps bringing you problems but no solutions.
It is useful with a family member in the business who wants your answer but needs to build their own judgement.
And it is useful for the owner too.
Because sometimes the owner’s speed becomes the team’s ceiling.
If every problem lands on your desk and you solve it quickly, people learn to bring you problems rather than develop their own thinking.
Better questions help break that pattern.
They move the conversation from dependence to ownership.
Reflection
Better questions do not make leadership slower. They make thinking clearer.
There will always be moments where a business owner needs to decide quickly. That is part of the job. But if every conversation becomes a race to the answer, you may solve the immediate problem while missing the deeper issue.
The quality of the question often determines the quality of the thinking.
And the quality of the thinking determines the quality of the decision.
So before you give the answer, pause.
Ask one more question.
It may be the question that changes the whole conversation.
Three Key Learnings
- Fast answers often come from narrow questions.
- Better questions create clarity, ownership and better thinking.
- The best leaders do not solve problems. They help people think better about the solving the problem themselves.
If you liked this newsletter, please like, share, and comment.
If you want to learn more about joining a Peer Advisory Board or simply have a conversation over coffee about it, feel free to send me a message.
You can send me a DM or contact me here.
Coach Colin at the Alternative Board
I guide Overwhelmed and Frustrated Business Owners and their Management Team from Chaos to Clarity & Control using the Business Builders Blueprint™ to Improve their Business & Change their Lives.
Join The Leadership Conversation and subscribe to my newsletter https://www.linkedin.com/build-relation/newsletter-follow?entityUrn=7150733264989655041 for the mindset, skillset and activity needed to be a great leader.
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