I started my professional career giving advice in highly technical roles. I learned a lesson that stuck with me through every sales and business role since.
The usual “know you, like you, trust you” mantra espoused by so many sales books is simply not applicable.
People follow your advice and buy when there is respect, credibility, and trust.
Respect is earned by asking questions that demonstrate you understand their world. By naming the problem they haven’t been able to articulate. By showing you’ve seen this pattern before and know where it leads.
Credibility follows when your diagnosis is sharper than what they’ve heard from anyone else. When you challenge a comfortable assumption with evidence instead of nodding along.
Trust comes from those two things compounding over time. It’s an outcome, not a tactic.
You don’t manufacture trust by being agreeable. You earn it by being consistently useful and willing to challenge your prospect’s thinking.
I’ve seen plenty of highly experienced business owners fall into the “know you, like you” trap.
Great conversations. Your prospect listens attentively. They nod. You send them a proposal. You follow up politely, and then everything goes dark.
You assume the prospect wasn’t ready, the timing was wrong, or they went with another option.
Usually, none of those things are true.
The prospect never felt the weight of their own problem. The conversation was comfortable, so the problem felt manageable. And when a problem feels manageable, the status quo wins. They do nothing.
Which means you actually did them a disservice. You let them walk away feeling fine about a situation that isn’t fine at all.
All selling is a form of leadership. You’re helping someone see the real issue, acknowledge it matters enough to act on, and commit to doing something about it.
That requires you to stay centred. To ask questions that go deeper than comfortable. To push past vague answers until you reach something specific and concrete.
It means being direct about whether you can actually help, rather than trying to stay in every conversation just in case something comes of it.
None of this requires you to be aggressive or cold or transactional.
It requires you to care more about your prospect’s outcome than about whether they like you in the moment.
Here’s the paradox.
When you stop trying to be liked and focus on being genuinely helpful, even when it’s challenging, you end up being liked more.
People remember the person who told them the truth. They refer the advisor who challenged their thinking. They come back to the consultant who made them slightly uncomfortable but turned out to be right.
They don’t remember the ones who nodded along and sent a nice follow-up email.
If any of this sounds familiar, it’s worth asking yourself which version you’re showing up as.
