Aoife Hollywood
A few weeks ago, I declared myself the office guinea pig after I was nominated to interview my boss, our founding partner, Malcolm Robertson, in front of the entire team.
For context, this was the launch of something new for us: a series we are calling The Backstory. The idea is simple. One member of the team interviews another about their life, their career, and the journey that brought them here. Not the CV version, the real version.
In the lead-up, I was uneasy and mildly terrified. I even wrote my last View from the Street about my prep, just in case it all went disastrously wrong and you happened to see my job advertised. At least then you’d have the context.
But now that it’s done, I can confirm two things:
- I survivedand stillhave a job.
- It wasnotas terrifying as the version I’d created in my head.
Plot twist, it was… enjoyable.
More than that, it taught me a few lessons I thought I’d share.
Lesson one: having a script is both your safety blanket and the first thing to betray you.
I had what I thought was a safe, warm opening.
We’d been debating Type A versus Type B personalities in the office for weeks. Type A: driven, competitive, restless. Type B: more laid-back, reflective, creative. It felt like the perfect way in. Relatable. Light. Two possible answers. What could go wrong?
To ease him in, I even gave Malcolm the first question in advance, just the first, so he could prepare and settle into the conversation, and I could have a sense of how to steer the conversation.
Except I forgot to ask what his answer would be (not very type A of me).
So, I opened confidently: “Where do you think you sit, Type A or Type B?”
Malcolm paused, looked at me, and said he didn’t think he fits into either.
And just like that, I could feel my beautifully pre-prepared follow-up questions quietly dissolving in my hands.
Because, of course, I had follow-ups. Carefully structured ones. Based entirely on the assumption that he would pick one of the two options I had so neatly laid out.
When he didn’t, I had a choice: panic and drag him back to my script or lean in and explore why he rejected both.
From that point on, the conversation refused to behave exactly as I’d mapped it. Stories overlapped. A reflection in question two set up something better suited to question five.
And it was better for it.
Because of the prep, including an hour-long session with Malcolm beforehand, I knew the terrain. I’d heard longer versions of certain stories, sensed where emotion lived, and understood which threads were worth pulling.
That groundwork meant when the order shifted, I wasn’t scrambling for the next line on the page. I was listening.
Preparation, it turns out, is less about sticking to the script and more about having the confidence to abandon it.
Lesson two: don’t save the day.
There was a moment, the kind you cannot plan, when I felt the weight of what we were doing.
Every year, Malcolm posts about the Dunblane shootings. It’s something he marks publicly but, understandably, doesn’t talk about very often. I asked because it felt important to understand how growing up there, and going to Dunblane Primary School, shaped him as a person.
But as soon as I raised it, the tone shifted. His expression changed. The room went very still.
And everything in me wanted to jump in.
To soften it. To rescue. To move us along.
But some moments don’t need managing. They need space.
So, I didn’t interrupt.
Silence stretched. You could see him thinking in real time. The audience could feel it too. That pause did more than any perfectly worded follow-up question ever could. It signalled that this wasn’t rehearsed or polished. You could see the emotion in his face, and, for a moment, the team caught a glimpse of what this means to him.
Not saving the day was harder than asking the question. But it was important.
Lesson three: environment matters more than you think.
We deliberately stripped the room back. No boardroom table. No desks as barriers. Two armchairs at the front. Sofas around us. Drinks in everyone’s hands. It felt more like a living room than a leadership Q&A. The team even said it felt like they had been transported out of the office for a while.
That small shift in space made a big difference. It changed the tone and made the whole interview feel less intimidating.
Lesson four: confidence grows where it feels safe.
I won’t pretend the nerves disappeared. They didn’t. But starting in a space that felt safe, among colleagues that wanted it to go well, made a difference.
Interviewing your boss sounds intimidating (and it is). But knowing the room was rooting for me (Malcolm was too) changed how I felt.
The most rewarding part has been the ripple effect.
Since that first session of The Backstory, others in our team have said they’re keen to try similar conversations. And beyond our office, other businesses and organisations have told us they’re trying it out too.
This feels significant. Because this was never about one interview. It was about curiosity.
We work alongside each other every day. We discuss deadlines, strategy, targets. But we rarely pause to understand the decisions that shaped someone, the doubts they carried, the sacrifices made quietly in the background.
An hour of intentional listening changed that.
I was the guinea pig.
And I’d volunteer next time.