At work, I have been set a challenge to try something a little different: asking the same question 50 different ways. Sounds a bit excessive? Maybe. But what I’ve uncovered has been surprisingly powerful.
This all started with a simple idea: the way you ask a question often matters just as much, if not more, than what you’re actually asking. So we set out to explore this. I asked the MorePeople team one underlying question:
"What do you wish you’d known earlier in your role?"
But instead of asking it once, I rephrased it - over, and over, and over again. Here's what I learned.
Small Changes, Big Impact
At first glance, questions like “What’s one tip you’d give a newbie?” and “What’s something you learned the hard way?” might seem almost identical. But the responses told a different story.
The first tended to prompt practical, bite-sized advice: “Jump on the phone. Learn by doing.” The second brought out vulnerability: stories of resilience, stress, emotional intelligence, and mistakes that left a mark.
That shift from general to personal, from helpful to human, was entirely down to the wording.
Tone and Framing Matter
Some of the most revealing answers came when I framed our questions around feelings, not facts.
“What do you wish someone had been honest with you about?” sparked confessions about the emotional rollercoaster of recruitment.
“What do you know now that would’ve made your start smoother?” brought out tactical insights about software, planning, and time management.
Framing a question as a truth, regret, or moment of realisation invites a different kind of reflection. The lesson? If you want depth, give people permission to go there.
Curiosity Builds Trust
Interestingly, asking a question differently, even when people had already answered a version of it, often led them to share more.
That’s something we can all apply. Whether you’re interviewing a candidate, coaching a peer, or leading a team, repeating a question with a new twist can open up a whole new layer of insight.
For example:
“What advice do you wish had come your way earlier?”
“What’s something you understand now that you wish you had earlier?”
“What’s a piece of wisdom you didn’t know you needed at the start?”
They all orbit the same idea, but they surface different memories, emotions, and lessons.
Patterns Point to Priorities
Across all the variations, some themes came up again and again:
Resilience – Nearly everyone mentioned learning to handle setbacks, rejections, and radio silence from candidates or clients.
Curiosity and learning – "Be a sponge" was repeated more than once. So was "ask the room."
Relationships over transactions – From building trust with candidates to forming real bonds with colleagues, connection was key.
These repeating patterns told us not just what questions worked, but what matters to our people.
Better Questions = Better Culture
Maybe the most important learning? Asking better questions isn’t just about getting better answers; it’s about building a stronger culture.
By creating a space for honesty, reflection, and sharing, we unlocked something bigger than advice for new starters. We built a deeper sense of community.
What We Now Ask Ourselves
If you're keen to try something similar, here are a few of our favourite rephrased questions to spark conversation:
“If you could go back to Day One, what would you tell yourself?”
“What’s one thing that would’ve saved you a headache?”
“What advice do you now give that no one gave you?”
“What caught you off guard when you started?”
“What do people overlook when they’re new?”
Try them in onboarding sessions. Use them in team meetings. Bring them into 1:1s. You might be surprised by what you uncover.
Final Thought:
The challenge was set out to improve questioning skills. But what I found was this: better questions lead to better conversations, and better conversations lead to better teams.
Sometimes, all it takes is asking the same thing... just a little differently.
