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Hot: Wired for Connection 3: Advice on Leadership and Equality from Andrew Wallace

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May 26, 2025 2 min read
Hot: Wired for Connection 3: Advice on Leadership and Equality from Andrew Wallace

Andrew Wallace leads the team at Smileback, which is now part of ConnectWise. He’s an IT Nation Evolve facilitator and SME and helps drive the broader product management practice at ConnectWise.

An Interview With Andrew Wallace

Why You Need to be in the Room to Talk About Equality

The first time Vera and Andrew met was at a side event at DattoCon – one of his colleagues invited him to a roundtable discussion about women in tech. The attendees were talking about their experiences and challenges.

Andrew says it was important for him to be there to better understand how men can support women to advance in the industry: “I believe we need to be involved in the cause and see how I can contribute.

“For me, equality and diversity isn’t only the right thing to do, but it makes us all stronger. It makes the industry better. So if I can support, learn and find out more about how I can support women and minorities in the community, I should be there. It benefits all of us.”

A High Point and a Low Point in Andrew’s Career

Andrew admits that he doesn’t pinpoint moments in his past in that way, but definitely a low point for him was when he made the decision to leave his career in journalism. “I like the act of writing, but I don’t like the business of journalism. I didn’t feel that I fit in culturally.

“I had different interests and a different orientation, and it just wasn’t ‘my people’. It was tough, because I didn’t know what else to do.” Andrew finds it easier to identify a win, though: “Early on in my career I worked for a Canadian charity called Athletes for Africa, where we organised a fundraising football game.

“Even though we were a tiny organisation, we got a roster of ex professional footballers and professional musicians to talk part. It was such a success and we raised so much money. And the winning team got to go backstage at a show by Arcade Fire. It was super cool!”

Why High Fives are a Sign of Good Leadership

Andrew admits that he’s not somebody who feels the need to celebrate small wins – he’s on to the next task as soon as the previous one is done. “I don’t care about the high five, physically or metaphorically.

“But I do know that others do, so I need to remember that my staff and those around me appreciate it when we make time to acknowledge success. A friend of mine does this really well – he takes the team out for drinks at the end of a project, so I try to support it in the workplace.”

As Vera points out, people need different kinds of interactions and support, so some want to celebrate and others prefer not to. “It’s a good leadership quality to identify the traits and preferences in each individual, and praise them in the right way.”

What can leaders do to better support their teams and champion diversity? Andrew Wallace of Smileback tells Lenka and Vera how he does it. Click to Tweet

Show Strong Leadership in the Way You Support Your Staff

Imposter syndrome happens in all industries, and the tech space is no exception. Sadly, both Andrew and Vera have had staff second-guess themselves. “I think what happens is they compare their progress to someone else’s.

“So rather than doing that, take time to do some self-reflection. Ask yourself, ‘What do I want? How can I achieve it?’ Think about the practical steps, and ask your manager for help. A good leader will support you with your growth and signpost you to learning opportunities.

“Your success in work is not your whole identity and it doesn’t reflect your worth. Be really clear about what’s important to you and focus on that instead. And if you have an employee who’s struggling, ask them the questions to prompt them. Don’t just give them answers that might not be right for them.”

The Best and Worst Parts About the MSP Industry

The part of the industry Andrew loves is the community, particularly when they come together for events such as IT Nation Evolve. “I think the sharing of best practices and how willing and open everyone is. It’s a nerd ethos that that underpins all of it.

“I have to share two things about the industry I’d like to change. One is diversity, because obviously there’s a diversity issue. We would see much better and more interesting outcomes for everyone if we were more diverse as a whole.”

Second, Andrew thinks the industry could benefit from being more professional. “That’s in how you talk to your clients, your customer service, how you support them. And internally, consider how to scale and what best practice looks like. How can you be a better MSP leader? Can you take inspiration from other sectors?”

How MSP Leaders can Drive Change for Equality

As a leader, you need to engage with the issues that some of your team, your colleagues and suppliers are facing, says Andrew. “This is the reality of the world we’re living in, and it’s having an impact on people in the industry now.

“And as leaders, we have both a responsibility and an opportunity to drive that change. To me, that’s the place to start. There aren’t enough people going out and working to drive change, although you guys are with this podcast. So this is a good starting point!”

Andrew, Lenka and Vera agree that these are challenging topics, but as the owner or a senior executive in an MSP, it IS up to you to lead the change. If you’re in a privileged position, acknowledge it and then look for ways to use it to improve the industry.

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