View from the Street: I was asked to interview my boss (in front of everyone I work with). Here’s what I learned.
Published
Aoife Hollywood
For one week only I am the office guinea pig.
We are trying a new work thing where team members interview each other about how they got here. The rest of my colleagues will sit around, possibly in a horseshoe, and listen, hopefully enjoying but probably quietly critiquing how it’s going.
I am slightly terrified, especially as my interviewee is the founding partner, Malcolm Robertson.
In my head this could be career-ending. I hope you see that.
We are calling it The Backstory. We work alongside each other every day, but there’s still so much we don’t know beyond the “how was your weekend?” enquiries or quick chats at the lunch table.
A few weeks ago, when our senior partner, Frank, asked me to lead the interview with Malcolm to kick off the series, I panicked.
An ‘In Conversation With The Founder?’ What? The person helping shape my professional career and, well, paying my salary? Instead of thinking about crafting thoughtful questions, I was focused on only two things: how not to make it a complete flop and where to get some beta blockers.
This was classic out-of-your-comfort-zone stuff.
But as I started preparing, something shifted.
I realised that jumping in where you would never normally do so, is sometimes the greatest teacher of all. A deadline. Peer pressure. The risk of failure.
I realised this isn’t just about one internal interview. It is about the craft of interviewing itself.
It’s tempting to think this should be straightforward. I have known Malcolm for 18 months. I see him every week. We sit in the same meetings.
But familiarity isn’t preparation.
My job isn’t to have a blether. It’s to uncover something worth hearing. After all, our team is giving up an hour of time. They should leave with something new – a deeper insight, a different perspective, a clearer understanding of Malcolm.
This takes distance, reflection and intent.
I don’t want it to feel like a firing squad of predictable questions – where did you grow up? What was your first job? Nor do I want it to be a brisk canter through his CV.
The real preparation lay in doing a pre-session discussion:
- What moments shaped how he thinks?
- Which decisions carried uncertainty?
- What failures still stay with you
- Was it all worth it?
That’s where the depth lies.
Framing matters more than you might think.
A flat question can feel blunt; a thoughtful one invites reflection.
Compare: “Why did you do X?” versus “I’m curious about that decision, what led you there?”
It’s a subtle shift, but tone changes everything. One can feel accusatory, the other opens space. In media interviews we see this every day. The way a question is framed can determine whether you get a rehearsed line or a revealing answer.
If preparation sets the foundation, listening builds the house.
My instinct, when nervous, is to cling to a script. Having questions written down feels safe, it gives me something to fall back on.
But the most interesting moments rarely sit neatly on the page. These surface in passing comments or unexpected reflections.
Active listening lets a conversation breathe – and it requires restraint, resisting the urge to interrupt or move things along too quickly.
The power of silence cannot be overstated.
Silence is uncomfortable for me. I have a habit of rushing to fill the gaps before they become awkward. But watching strong interviews has changed my view. A well-timed pause allows a story to land. It can give the other person room to go further, and that’s often where the real insight lies.
When you resist the urge to fill every gap, you demonstrate control, not anxiety.
Then there’s hierarchy.
Founder. CEO. Boss.
Titles loom large. It would be easy to let that shape the tone and avoid the uncomfortable question.
Hierarchy only matters if you let it. The dynamic is yours to create.
A strong interview doesn’t diminish authority. It creates a space for ideas to take centre stage.
Turning the tables is still intimidating. But it’s also an opportunity to have a conversation where curiosity outweighs hierarchy, reflection outweighs performance, and something real might surface.
The interview hasn’t happened yet. But it’s already taught me this: interviewing is far more than asking questions. It’s preparation. Framing. Listening. Pacing. Restraint. And perhaps most importantly, it’s about creating the conditions where someone feels able and willing to say something that matters.
That’s a craft worth practising, no matter who’s on the other side of the mic.
The real test for me comes next week. I’ll let you know how it goes.