Humans of Tech – Oliver Fisher

This month we had the absolute pleasure of chatting with Oliver Fisher, VP of Engineering at FreshBooks. Check out his insights on balancing commuting from Ottawa to Toronto 3 days a week, and his thoughts on inspiration based leadership. 

You have a very unique commute – flying from Toronto to Ottawa for 3 days at a time! How did you and your team figure out this arrangement? How do you make it work with your family and your team?

I have been working remotely for 16 out of the past 20 years, so I’m fairly used to its ins and outs. When I was looking for my next steps, I was looking for a company with a really great culture. That’s when Steph introduced me to Warren, Freshbooks’ CTO at the time. We really hit it off and I was upfront about the fact that I lived in Ottawa and wanted to continue to live here. Warren was hesitant to having the VP of Engineering work remotely but executives working remotely wasn’t something new in the company. With a little push from Steph, Warren brought me on.

My team and I manage like any other team figures out how to communicate. My team knows the best way to get a hold of me when I’m in Ottawa or traveling, and I make sure that I focus almost all my time in the physical office on talking to people. We also use video conferencing and, if I need to, I’ll use the office robot to act as my physical presence in the office.

As for my family, they’re just wonderful people. My wife and I have an 8 year old son and twin 3 year old girls and she runs her own law firm in Ottawa. We’ve been able to find a routine that works for us and I make sure that I make commitments to spending time with them. For example, a non-negotiable for me is making sure I attend my son’s Beavers’ meetings Wednesday nights. It means I have to leave the office a little earlier but it’s part of finding the balance. Luckily, my commute only is 2.5 hours door to door so I’m able to see my family in the morning, and then see my kids before they go to sleep at night. I’m really grateful for them.  


What are you most proud of professionally?

I’m most proud of co-founding and working for 5 years with Google’s anti-malware team during its early days in Montreal. We were really the first to do large scale malware detection across the entire internet and we made a big difference in the lives of millions of people. I loved having that kind of positive impact on the world.

That and we had an xkcd comic made about the work we were doing. I’m not sure there is a higher form of flattery.


What sparked you to pursue engineering leadership as your career path?

I was drawn to this path because of the possibility of building something. I’ve found this to be true on both the technical side and on the people side of things. Throughout my life, I’ve enjoyed bringing together a group of people to achieve a common goal and solving tough problems.

Bill Coughran, a former VP at Google, shifted my perspective from the technical to be more people focused when he said that computers are the easy part – it’s the people that are hard. It really is true. You do get a tremendous sense of accomplishment when you create a program that works but you feel far more rewarded when you see a person you’ve been mentoring succeed. It’s less about you and more about the person, but you see the real impact that you’ve had on that person’s life.


Working in the tech industry can be very demanding, what do you do outside work to maintain energy?

I workout fairly religiously but I eat too much as well, so that balances. Working out is critical to keeping the energy level up and stress down. During a particularly stressful bathroom renovation, I took up Zen Buddhism and while the Buddhism didn’t really stick, the meditation did.  Mindful meditation has helped a lot over the years.


What is your favourite book? Or what was the most recent book you read?

Honestly, I read a lot of fiction – science fiction or British crime drama are my go-tos. I really like the Expanse series. The Red Rising series – incredible series of books. Ready Player One (I read this before it was a movie, I swear!).

I recently read Accelerate by Nicole Forsgren, Jez Humble and Gene Kim about the science behind Agile teams and how they drive business success. It’s a pretty academic and technical book, but I love it. It’s the first time I’ve seen evidence of causation behind various practices and it can give you a map of where to start and why.

It also links success to Transformational Leadership. We’ve been bombarded by Servant Leadership over the past few years – personally I’ve always found it a bit simplistic. Transformational Leadership turns out to be my default style, so, of course, I love it. But Accelerate also finds that it ties much more closely with business success.


What advice would you give your 18 year old self?

Do what you’re doing. It’s going to work out ok. I’m really happy with how things have worked out. The only way to get to where you need to be is to make mistakes. I would just want to give myself a little more confidence that it will work out.


What advice do you have for leaders and entrepreneurs looking to hire great people and establish a strong culture?

Part of why I like working at Freshbooks is because of our strong culture based all around trust. Our approach is that trust is given to be earned.  And we phrase it very deliberately that way. The default is to trust people. It’s not going to be perfect, but trust that they’re working the best they can. When people make mistakes, that’s ok. Trusting that the person is trying to do the right thing is an integral part.

I want to clarify a little – our approach is different from the “I’m right. Just trust me” and more based on the idea that everyone trusts that the team is working toward our common goal.

When I’m hiring people – among all the standard things you look for like intelligence – I’m looking for people who are able to give that trust, not just benefit from that trust. You want people who feel ok making mistakes and feel ok letting other people make mistakes. Those two things don’t always exist together in a person. So my advice would be to hire those who trust and can be trusted.