In Conversation with Duncan Finlayson | Partner, Product, Data, Technology & AI · Calibre One · Based in London
Candid with Calibre One is a series of conversations with our partners – honest, unfiltered perspectives on leadership, hiring, and what’s really happening in the world. No set agenda, just questions worth asking. For this feature, we sat down with Duncan Finlayson, a partner at Calibre One who leads our Product, Data, Technology & AI practice. One of the early European founders of True Search, he went on to lead the firm’s EMEA and APAC product, data, technology and AI practice before joining Calibre One.
What are you seeing in the market right now that leaders aren’t talking about enough?
Duncan Finlayson: “Our whole industry used to be order-taking, especially in technology searches. It was, ‘I need A, B, C, D, E.’ Now, with this layer of AI and no shortage of buzzwords, it’s, ‘We think we need A, B and C – can you help us with D and E, and maybe F too?’
The interesting and more exciting thing is that we’re having to be far more consultative and clients are leaning on us as true function experts more than ever before. It’s great when clients trust you and let you do your job, and when the board and investors are genuinely engaged with the hiring team in the portfolio.
But there are more stakeholders now than ever who are cautious about making the wrong hire, especially in AI and technology.
What used to be a fairly defined set of skills and requirements is now – well, the whole world is just trying to figure this thing out with AI, especially agentic engineering and AI enablement. We’re asking one executive to have four or five different skill sets rolled into one, and then be an expert in AI on top of that. From an AI perspective, especially agentic engineering, this has really only been in production and R&D for the last ten months.”
That shift – from order-taking to consultative partner – changes what a good search conversation even looks like. Which raises the obvious follow-on: what does Duncan actually ask to get past the scorecard?
What’s the one question you always ask that tells you more than anything else?
Duncan Finlayson: “It’s actually my favourite two questions, so I’ll allow myself both. The first is: tell me about your upbringing.
I find it really interesting, because we’re so used to getting on these calls after a screening call and an interview, and going straight into sales mode – assessing someone against a scorecard. Instead, I ask about their childhood. Not in an invasive way, just: what are you intrinsically motivated by? What excites you? What was one childhood experience which has influenced your career to date?
Some candidates run with it more than others. I had one candidate spend forty minutes of an hour-long interview on his upbringing. I had to remind myself it wasn’t a therapy session, and that I still needed to assess him against the role.
I think the best thing you can do in this job is build close, genuine relationships with candidates. I’ve been fortunate in that respect. I’ve been deep in one function, product, data, technology and AI hiring, for fifteen years, and done over 250 of these searches. You get to know a lot of candidates incredibly well over that time.
The second question, which tell you a lot about them as an individual is: describe yourself in three words.”
What’s the one thing your clients consistently underestimate when making a senior hire?
Duncan Finlayson: “How much actually goes into an executive search. I’ll spend a good hour just on kickoff templates and documents before we even get going – and that’s after the BD process and signing the contract, which is its own set of conversations.
Then there’s building a comprehensive job brief, a comprehensive scorecard, a search criteria and a target landscape that the client signs off on. That’s my process, because I want to make sure I’ve spoken to every key decision-maker – and that alone can take four or five business days. Then you have to move quickly, because every client wants to hire someone yesterday.
There’s also just the sheer volume of it – the hours on LinkedIn, the outreach, moving between systems like your CRM, mobile phone messages and emails, making sure it’s all balanced, whilst managing internal teams and client expectations etc.
I think what I love about this industry, but what’s also underestimated, is that you can do the exact same thing one week and the next, and get completely different results.”
That operational intensity raises an obvious follow-on: with so many moving parts, what actually separates the clients who make the process easier?
What skill do your best clients all seem to have in common?
Duncan Finlayson: “They listen, and they’re happy to take guidance on who the best candidate is for their opportunity – not necessarily the best candidate in the market generally.
A good example: we recently placed a Chief Technology & Information Officer at, a large-cap PE-backed business, reporting to a CEO who was making his first technical hire at this level. He told us, ‘I like all five of these candidates, just tell us who we should offer.’ I found that stressful at first, because we’re the ones giving the guidance, but it’s ultimately his decision. It was also empowering, though – it meant we’d done the work properly and had the right data on the candidates.
Without trying to play God, or let ego get in the way, it was nice to be a true consultant in every sense of the word. Sometimes in our industry it’s just ‘give me some candidates – nobody reads the interview reports, nobody logs into the CRM.
I think that’s both the beauty and the challenge of this industry: it’s multi-billion dollar, and it’s unregulated, which makes for a very interesting dynamic.”
From the operational to the personal – the conversation shifts gears for two wildcard questions.
What would you be doing if you weren’t in executive search?
Duncan Finlayson: “Probably lying on a beach somewhere in Ibiza, hosting retreats. Ibiza is my spiritual home – I’ve had some incredible experiences there, and I’ve only ever been sober for all of them, which isn’t exactly the norm for the island. There’s a beauty to the place like nowhere else, something about really connecting with the universe. I’d love to have a little farm there one day.”
What’s the most amusing – or humbling – story from your career you’re willing to tell?
Duncan Finlayson: “This actually came up again just today, funnily enough. Do you remember GMass – the mass-email tool, a bit like Mailchimp but for Gmail? At a previous firm, we had an associate – who obviously won’t be named, for GDPR reasons – who accidentally sent 400 people’s personal, confidential information out to all of our clients and candidates in one go. The emails came flooding in. He went white.
We had to spend the next six months ringing round, apologising to every client and candidates making sure everyone had properly opted back in to our system and wanted to be contacted in by us in the future. But actually, it turned out to be a great learning experience for him. He’s now one of the most successful people in the business. Good things can come from chaos, I suppose. It goes back to one of the harder lessons of this job: if you’re not diligent, if you don’t have the right processes and structure in place – there are so many moving parts in executive search, and it only takes one click to send confidential information to 400 people.”
A good reminder that in executive search, the details are the job – and that even the worst day can become the best education.
This conversation has been edited for length and clarity.