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Dare to Ask the Ultimate Question

Mar 4, 2025 | Business, Communication

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Dare to Ask the Ultimate Question

(This content was originally published on Joe McCormack’s Just Saying LinkedIn newsletter.)

In marketing, the ultimate question is “how likely are you to recommend us to a friend or colleague?” Pretty straightforward. It gets to the heart of customer loyalty and brand advocacy and is called a Net Promoter Score (NPS). Scores of 9 and 10 are the sweet spot. Less than that and there may be customer experience problems lurking.

Recently, I started asking my clients a different “ultimate question” that’s equally pointed and powerful.

“What’s a big challenge that you and your team face right now?”

Why ask someone this? Simply because I liked it when someone asked me. It made me stop and think. It showed me their interest and concern. It helped me focus. What’s more, it would help me better understand my clients.

What makes this question work is it asks for a challenge, not the challenge that you face right now. Maybe you immediately know the biggest issue you face, but chances are you have a few. You may not have thought a lot about it. Or nobody ever asks you.

It got me thinking.

Two executives engaged in conversation in a bright office.

It’s Better to be Interested (than Interesting)

If driven from genuine interest, questions like this can really help. For me, I not only began to think about my current challenges but also about why I don’t ask my clients and contacts better questions like this.

Could I ask this one more often? Why not? It could help deepen a relationship by identifying their source of struggle, show that I care enough to ask and get them talking about it. It was s a small risk worth taking, so I started.

You Won’t Know Unless You Ask

Often, the best conversations start with a question. Maybe it’s a client or colleague. Family member or friend. Everyone has issues and getting them to open up might be exactly what they need.

Or they may not want to tell you. That’s fine too. But they may be dying to let you know and haven’t had anyone that cares enough to ask.

An Agenda-less Conversation

Over the past month, I started asking my version of the “ultimate question” more often. At first, it felt a little weird. Maybe too direct. I needed to remind myself that by asking the question I wasn’t looking for anything in particular. I was just asking.

I had to practice “present listening” myself. It was a term I coined in my second book “Noise: Living and leading when nobody can focus” that means both being in the present moment and giving the gift of my undivided attention. (For more on this topic, listen to a past podcast episode – “Present listening and preaching to the choir” #108).

The conversations got better. I started seeing that asking it once wasn’t enough and began asking it again to uncover another challenge. The more they wanted to talk about it, the bigger the issue was.

Asking Much Better Questions

So what do you do when you get the answer? Initially, nothing. Now is not the time to solve the problem, but just understand why it matters to them.

Conversations like these will motivate you to learn to ask better questions. It’s a rare skill but feels so good when someone asks it. It shows they care. (For more information on this topic, listen to another past podcast episode – “Asking much better questions” #63).

Don’t be afraid to ask. Just sit tight and listen to understand (not to fix). #justsaying

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