Ask Better Questions
Phase 1 | Foundations
Session 2 | Ask Better Questions
Entrepreneurs are, by nature, problem-solvers. But most people don’t realise that problem-solving doesn’t start with having the right answers – it starts with asking the right questions.
And most of us, frankly, ask terrible ones.
We ask questions like:
"Why isn’t this working?"
"What if I fail again?"
"Why can’t I just be more confident?"
"What if no one wants this?"
And our brains, being the obedient search engines they are, go off and find all the reasons why we’re doomed.
Better entrepreneurs ask better questions. They ask questions that unlock possibility, clarity, creativity and action.
Try these instead:
"What would this look like if it were simple?"
"Who could help me with this?"
"What’s the tiniest next step I can take to test this idea?"
"What am I assuming that might not be true?"
When I changed the questions I was asking, everything changed.
Back when I was rebuilding after the collapse of The Money Gym, I spent a lot of time stuck in the wrong questions. Why me? Why now? Why didn’t I see it coming? And I stayed stuck longer than I needed to.
But when I began asking, "What do I still believe in? What could I build next that would matter more? Who do I actually want to help now?" – that’s when I started to move again.
Questions are direction-setting tools. They steer your focus, shape your energy, and determine what information you notice. Entrepreneurs who know how to ask better questions get better results – not because they’re smarter, but because they’re looking where others aren’t.
Another time asking a better question worked springs to mind!
When I was trying to buy the Acacia Hotel, I needed a £500,000 mortgage. I’d negotiated some vendor finance from the seller, Brian, but I still needed to raise £350,000 to complete the deal.
“Adrian, I need you to come and see an amazing opportunity I’ve found and tell me what you think! More importantly, what the bank would think!”
He cleared his diary and came to the hotel that next morning. He took one look and said, “Oh yes, vendor finance is standard practice in business. This makes perfect sense.” Then he told me to go away and write up a proper business plan.
Which of course, I did — I’d written dozens over the years. I got it to him and my accountant within a week.
However, after a week or so, I called Adrian and he was sorry to say it was a straight-up “no”.
At first, I took it at face value. But it didn’t sit right. Either something in his tone alerted me or my intuition was ringing bells again.
So I rang him again and said,
"Adrian, was that a hard no, a 'no, not now' or 'no, not that much'?"
Turned out it was a 'no, not that much' so I went back to the vendor and we renegotiated the deal.
But if I hadn't asked that question, I would never have bought The Acacia, because my Bank Manager wasn't allowed to tell me why they wouldn't lend, I had to actually ask him.
Today’s Action:
Start a fresh page in your notebook. At the top, write:“If I were a better entrepreneur today, what would I ask myself?”
Then write down the first 5 questions that come to mind. Don’t edit them. Don’t try to be clever. Just listen.
Then pick one and sit with it for 10 minutes. Let it work on you.
And if you want to go deeper, ask this one: “What question am I avoiding asking because I already know the answer?”
You’ll be surprised how much power is sitting quietly behind that one.
Better questions lead to better insights. Better insights lead to better actions.
That’s how we build.
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Photo by Ana Municio on Unsplash