When I first moved into sales from a technical background, I thought I had to know all the answers. I genuinely believed that was the job. Know the product, know the specifications, know every possible objection and be ready with the perfect response before it even happened.
So I did what felt logical. I talked.
I explained features, processes, technical details and benefits because I thought if I could explain things clearly enough, people would naturally see the value. Looking back, it made complete sense at the time. If somebody needed help, surely giving them more information was the answer.
The problem was that something always felt a bit off.
The conversations felt heavy, and I was doing most of the work. I would leave meetings feeling like I had delivered a presentation rather than actually had a conversation with someone. I wasn’t really learning much about the person sitting opposite me because I was too focused on saying the right things.
Over time, I realised something interesting. The conversations that felt easiest, and usually led somewhere, were never the ones where I had all the answers. They were the ones where I asked better questions.
I still remember noticing the shift because it surprised me. The meetings felt lighter. People opened up more. Conversations stopped feeling like something I had to manage and started feeling much more natural.
Not because I suddenly became brilliant at sales. I just became more curious.
One of the first questions that changed things for me was:
“Can I ask what’s prompted you to look at this now?”
It sounds incredibly simple, but it stopped me from making assumptions.
Instead of trying to work out the problem myself and fit my solution around it, I was hearing directly from them. Sometimes the answer was exactly what I expected and sometimes it wasn’t even close. People often tell you far more than you think they will when you simply give them the space to do it.
Another question I started using was:
“What happens if nothing changes?”
I still love this one because people will often tell you what they want, but not necessarily why it matters.
The answer might be money. It might be time. It might be frustration. Sometimes it is pressure coming from somewhere else entirely. Occasionally, what appears to be a practical problem turns out to be a confidence problem or a resource problem.
You only really uncover that when you go a little deeper.
Then there is probably my favourite question:
“What would a good outcome look like for you?”
I love this because it takes the pressure out of sales completely.
The conversation stops being about proving why your product or service is brilliant and becomes something much more useful. It becomes about understanding whether you can actually help.
That subtle shift changes the whole feel of the conversation. Instead of trying to sell something, you start exploring something together.
The funny thing is that none of these questions are particularly clever. They are not secret persuasion techniques or hidden sales tactics that only experienced salespeople know about.
They’re really just curiosity.
Curiosity takes pressure away because suddenly you are not trying to think of the perfect thing to say next. You’re listening properly, understanding what matters and connecting with another person.
I used to think confidence in sales came from having all the answers. Now I think it is almost the opposite.
Confidence comes from trusting yourself enough to ask good questions and allowing the conversation to unfold naturally. Because selling isn’t about having the perfect script. It is about helping people feel understood.
And that’s where better conversations really begin.
If this feels familiar…
Inside Confident Selling™ we spend a lot of time working on conversations rather than scripts. The goal isn’t to sound like a salesperson. The goal is to sound like you… just with more clarity and confidence.