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Senior Spotlight: October

Crimson’s Head of Customer Engagement, Chris O’Brien, interviews senior technologists across the UK. Discover what drives these individuals as we delve into their careers, most exciting projects, and tech predictions for 2023 and beyond. Be inspired by their stories and connect with your IT peers.

Dan Leese | Former Head of Technology Delivery | Halfords

Connect with Dan

Chris: Great to see you again, Dan – so let’s jump right in.

How did you get to where you are now? Obviously, you worked most recently at Halfords, heading up technology delivery there, but how did you get to where you are now?

Dan: Ironically, I’m not a technologist at heart. I studied Environmental Science degree, specialising in hydrology water. I used that to get onto Severn Trent’s grad scheme – and from that moment, what I’ve done all throughout my career is manage people. I journeyed through front of house, contact centres, back office, and finally, to managing big teams of 100 people.

Chris: What would you say is your greatest strength doing what you do?

Dan: I think my skill set lies in the ability to convert the technical detail of somebody constructing a sewage treatment works or building some code to plain English that I can communicate to a customer, a supplier, or an executive. And it’s easier said than done!

Chris: I can imagine that! Along the same lines, what has been your biggest challenge – or challenges – that you’ve faced throughout your career?

Dan: I think for me, it’s the work-life balance. I’ve got two kids – my eldest is 12, and my youngest is nearly seven. So, trying to run big projects while taking care of two kids is challenging.

My wife also works four days a week in the NHS, which isn’t your typical nine-five role. Trying to balance that whole thing is like a triangle – work, kids, and a relationship – and getting it right is exceptionally hard. Often, I find myself working from home with Peppa Pig in the background, which is absolute chaos, as you might expect.

Chris: Yeah, I’m with you on that, especially Peppa Pig. How did COVID affect that actually?

Dan: At the time, I was running National Grid’s cybersecurity transformation program, so thankfully, we weren’t furloughed. And in fact, it was quite a critical time for cybersecurity. There were a few regulatory changes we were trying to achieve, so it was absolutely foot to the floor – that was hugely challenging. But at the end of the day, you have to decide which corner of the triangle you’re going to invest more time in each week and somehow keep that balanced.

Chris: And where do the people you manage come into that triangle? Because, of course, as a manager, you’ve got workflows, appraisals, flexible arrangements, and more to take into account. How effectively can you do that?

Dan: You raise a good point. For nearly two decades, I’ve successfully managed teams in person, so the past few years have been an adjustment – but at the end of the day, it’s all about motivating your staff.

I was quite lucky because, during my time at National Grid, I had some staff in the States and some in the UK, so I learned some remote management skills before the pandemic. But you still miss out on ‘corridor conversations’.

Chris: How do you think that has affected people’s mental health? We’ve noticed more candidates dropping out of the interview process because they’re finding it tough.

Dan: It’s really difficult. When you’re in a virtual meeting, if you think someone’s struggling, you can’t just ask, “Are you okay?” in front of everyone like you can more subtly in person. So, you have to find a new way of communicating. The main thing is figuring out how to motivate your team.

Chris: So, extending beyond just personal challenges, have you ever had a project that made you think, “Oh God, how do I get around this?”

Dan: Oh, of course. So, in terms of what I’ve worked on recently, the biggest challenge has been replacing critical legacy systems. It’s always a huge piece of work – maybe estimated to take about three years or so, swapping out existing toolsets and bringing in another toolset. And as you might expect, timelines don’t always go to plan – you can find yourself a year behind plan easily. You’re constantly worrying, “Am I going to make any money out of this? How do you then get that over the line?”

It’s especially difficult when the work is happening between two or three parties. So, some things might have been signed off, but when you pick it back up and review it, it’s not good enough. And sometimes, you get to a point where you can’t even go backwards. So, that’s been a real learning curve for me.

It’s taught me that all that upfront stuff, like contracts and planning documents, have to be exceptionally good. In most cases, it might be fine to be a little loose around the edges – but if something does go wrong, then you need it to answer the question, “Is this a scope change or is this just additional work ?”

Chris: Looking to the future, what do you think the next five years will look like for technological change?

Dan: As you might expect, in my past roles we have been talking heavily about AI. I have run teams where there has been a huge amount of money invested in eCommerce platforms where my team has worked on two weekly sprints, enhancing the customer experience, putting products out there, getting sales on your website, etc. But will there even be a website in five years’ time? Would you even use a website? Would you not just use your AI chat machine, Alexa, or whatever the new version of that is to go, “I want a tire of this size to fit this car.” Who knows?

So, I think the conversation turns to how much do you invest in now versus how much do you invest in AI for the future. There will be a time – fairly soon, I think – when AI can automate everyday things, like Holiday bookings or car MOTs or tire replacements, so we’ll need to think about how we can adapt to that in the near future.

But in terms of where I see myself in all of this, my ambition is to not just be a tech leader – it’s to become a broader COO, CTO, or MD and use my breadth of knowledge as a good foundation in stakeholder and people management.

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