Career Shaping Conversations: Ed Conolly

Who are you and what do you do?

I’m Ed and I’m a VP of Engineering at Cloudflare. We’re on a mission to build a better internet, and we’re both accelerating and protecting internet traffic today.

I focus on the protection side of what we do, leading teams that build products that shield websites, APIs and apps from security risks.

My dad was a technologist so I grew up around software, and was really into science when I was young, but I didn’t really want to follow in his footsteps.

However, I studied mathematical physics and found that I enjoyed the computational side of it which made me think that programming could be a good intersection of my skills and interests. And so that’s where my career led and I’ve worked for a bunch of companies building technology.

I also run a lot, and play the guitar and piano, although my repertoire is mostly nursery rhymes these days!

A conversation that changed my approach

Early on in my leadership journey I knew I needed to have a chat with a direct report who was really underperforming as a new manager.

I was convinced that the right course of action was to tell him it wasn’t working out. I felt that was what leading was - having to make tough choices. And I assumed my straight-talking boss would agree.

But he didn’t. He suggested I pause and think about how to approach things differently. He asked if I’d asked my direct report how he felt and how he thought things were going. I hadn’t.

So that’s what I did. I met with him and asked a lot of questions about how things were going, about how he thought the team felt, that sort of thing. The chat ended with no real conclusion so I felt a bit frustrated.

But a week later he came back and said he’d reflected on it and wanted a non-managerial role which would better suit him. By asking questions I’d let him come to the right decision on his own, and that was a real moment of realisation for me. Leading wasn’t just about being tough, it was about coaching others and creating the right conditions for them to succeed.

A conversation that built trust

I was convinced that my organisation was making a big mistake in deploying a new piece of technology, but the decision had already been made and I wasn’t sure how best to voice my opinion.

I went for a long walk with a colleague to discuss my thoughts and found out that he shared my viewpoint. We spent hours walking round a London park hashing out the various pros and cons of speaking up and challenging more senior team members about a decision they’d likely defend.

It was a really involved, deep conversation where we considered every option, including how our own careers might be affected by taking any action. And we started to build a real trust and understanding between us. knowing if we took on the issue together, we’d stand a better chance of being heard. And we workshopped an alternative solution there, together.

Having that conversation, and spending real time talking it through, gave us the confidence to act, so we did. And our views were eventually heard, and changes were made.

What that conversation really taught me, though, was the power of finding an ally, building a trusted partnership, and investing real time, not just snatching 30 mins or something, to collaborate and find a way forward.

A conversation that opened my eyes

’d been asked to lead a particularly challenging project and as we got into into it was clear that there was a major problem with a specific database my manager had chosen. I had a conversation with him, and he dismissed the team’s concerns and told me I was wrong, and to just make it work.

So I tried. The team tried. It was getting clearer that the database was the problem and we would fail if we didn’t change course. So I tried again and even documented my concerns, and was again told that I was wrong. But the project did eventually fail because of that database.

It was an eye-opening moment for me. It made me realise that I never wanted to be ‘that’ leader. I never wanted to be someone who wouldn’t listen to my team and at least consider things from their point of view.

As leaders we often get removed from the day-to-day and our teams amass better, more relevant knowledge. It’s our job to recognise that and to hear them out, to consider what they’re saying even if that makes things tough for us or we have to admit we’re wrong.

So those conversations really did give me a clear idea of what not to do, and it’s something I always try and keep in mind now, to trust my team and to listen to them.

Someone I’d like to have a career conversation with...

I’d like to talk to Bill Gates.

Not about technology or building Microsoft, but about how he made the transition from leading an incredibly successful company, from the corporate world, to having this very purpose-driven career.

Obviously he’s brought of what he learned through Microsoft to what he does with the Bill & Melinda Gates Foundation, but I think what I find most interesting is the decision-making process that goes into finding what you really care about, what you want to sink your time into.

Financial freedom provides the opportunity, of course, but you’ve also got to figure out where you can actually make an impact. So, yeah, I’d love to get into that with him.

I also think the way the Gates Foundation is so rigorous with data and analysis and measurement of impact is a reflection of his mindset. So ruthlessly analytical...

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