We’re launching episode four of People Leading People, the SoapBox podcast! Listen to the episode on Apple Podcasts, Google Podcasts, Stitcher or wherever you get your podcasts (be sure to subscribe and give us a review!).
In episode four, we’re chatting with Derek Marshall, CTO at Flight Network, the largest travel agency that is both owned and operated in Canada. Before landing at Flight Network, Derek spent time at various startups and enterprises including Bitstrips, ClearFit, Syncapse, CBC and Rogers. growing high performing technology teams and coaching them through the challenges of scale and cultural change.
We talk to Derek about hacking the bureaucracy and inheriting teams.
The episode and full transcript are below, but here are a few of our favourite things Derek had to say:
“I was able to get approvals on projects that, in some cases, surprised people how quickly we could actually get results. Taking a techie view of a large enterprise, I came to look at it as a large machine to hack and debug and some of my ideas and stuff they trained me on. Achieving results in a large enterprise, you have to learn how to hack the machine.” (Skip to 5:00 to listen to this part!)
"Achieving results in a large enterprise, you have to learn how to hack the machine." – Derek Marshall of @FlightNetwork Share on X“I think the main thing to do, and now I try and have as much discipline as possible, is articulating and understanding what the objectives are. Like, what needs to be accomplished? Why are these people here? Why are you all there? What does success truly look like?” (Skip to 11:20 to listen to this part!)
“I’d say one of the best skills you can develop is just writing and communicating crisply and clearly. I was lucky to have a boss who at the time, I was like, ‘Oh my God I feel like my homework’s getting marked.’ He would teach me, taking out this red pen and marking up what I’d written. I was like, ‘What the hell is going on?’ That again was also a good thing about being at the CBC surrounded by people who were journalists. They know how to write. The best managers there can communicate like crazy.” (Skip to 12:30 to listen to this part!)
Check out the episode below – and scroll down for a full transcript. Be sure to subscribe and review us in Apple Podcasts or wherever you listen (and we’d love for you to give us a ⭐️⭐️⭐️⭐️⭐️ rating!).
Happy listening!
Jillian Gora: Hey, everyone Jillian and Brennan here from SoapBox, welcome to People Leading People. Today we’re chatting with Derek Marshall, CTO at Flight Network, the largest travel agency that is both owned and operated in Canada.
Before landing at Flight Network, Derek spent types of various startups and enterprises including Bitstrips, ClearFit, Think Caps, the CBC and ClearFit, growing high-performing technology teams and coaching them through the challenges of scale and cultural change. Welcome, Derek.
Derek Marshall: Nice to see you again.
Jillian: Nice to see you too.
Brennan McEachran: Awesome. We were just chatting, we went deep into a bunch of things and I’d love to pull some of them out for the listeners, but maybe just quick to introduce some of your trajectory. Do you want to give us the highlights of some of what you’ve done in the past, and how you got to CTO of FlightNetwork.com?
Derek: A bit of background on me. I started in new media as it was called then at CBC. I had come from a bit of a technical background working in 3D animation, and quickly got thrust into helping scale that team from being new media in a corner to being the centre of attention for the entire CBC, and our audience is there. Lots of good technical challenges, many more people challenges, and took a lot of those learning’s and helped grow a digital media division at Rogers Media.
From there had a bunch of different startups that I got to help at who were at various stages of product delivery. Was super proud of the work we did at Bitstrips to help them transform into what is now their emoji. Seems to be the centre of attention versus inside snapshot. It was super great and really great people in there.
On the side looked at– Incubated my own startup on the side, because I like to scratch my technical itch every now and again, but I have a family and being precariously employed is not a thing. Rather than take that on full-time, I had the opportunity to join FlightNetwork.com a few years ago. It was a good challenge to help them figure out how to continue their growth as we started expanding into different countries around the world and different markets.
Brennan: Awesome. We’re going to get back to Flight Network, but I want to move to the start of your career where websites were considered new media and a side project that you put some young kids on. One of the things we were talking about earlier was CBC is a big place, and you were a young hungry problem solver. We got into a little bit of talking about politics and is politics is bad thing and a good thing. You came up with this term or I don’t know if you came up with it, but you used this term bureaucracy hacker. What’s a bureaucracy hacker?
Derek: I think probably what we’re seeing is politics has a bad name, and it’s not necessarily, if you think at more of a philosophical view of it. All your working life is centred around getting people to agree to agree in important things. Taking a techie view of a large enterprise, I looked at it as a– Or I came to look at it as a large machine to hack and debug and some of my ideas and stuff they trained me on. They gave me the toolkit and the training to learn how to actually achieve results, achieving results in a large enterprise you have to learn how to hack the machine.
Brennan: Hack the system, hack the machine and you became a brute force of getting things done.
Derek: I was able to get approvals on projects that in some cases surprise people how quickly we could actually get results.
Brennan: So much so that you said you ended up being the guy who got known for being able to get things done, you became– That’s how you first came–
Derek: Yes. I have called myself a bureaucracy hacker. So when I showed up at Rogers, they had been trying to — The media team had been trying to negotiate with a supplier who’s the leading web content delivery platform. I think the negotiation had gone for 18 months, and within two months we were able to cut through all the tape, get a deal done and get moving. That took a lot of bureaucracy hacking. It was extreme bureaucracy hacking.
Brennan: I think that the interesting thing– I don’t know we haven’t gotten too deep into it, but the interesting thing is unlike other hacking which gets bug fixes and security patches and the technology changes. Bureaucracy hacking probably doesn’t change too much. What are the hacks you learned throughout? What are the hacks people should take home tomorrow?
Derek: I’m sorry; I think I should make a bureaucracy hacking list and talk about–
Brennan: Yes, let’s do it right now
Jillian: Yes. That’d be a great loss. We’ll write it for you.
Derek: Okay, great. I don’t currently have that, but a couple of top things we talked through, and that you see the patterns that people who can get stuff done in companies, you see the patterns over time. If someone who I have a lot of respect for in our current team, who’s the project management group, he shows up to most meetings with food. Especially meetings where he needs to develop urgency around getting things done. Also often he will surprise people and delight them by dropping off a bottle of wine. I still have a little bottle of Sake sitting on my desk, he just wanted a vacation approval.
Jillian: Didn’t see him for two months.
Derek: There was a negotiation program that I had been on early in my career. The CBC was great for that because he had access to lots of training and support. One of the key things for successful negotiations was to build a personal relationship. A good tactic is to break bread with people and have lunch, share some food. It opens up and you were saying, it’s a good sales tactic.
Jillian: Yes, from a customer experience perspective. My whole history is working with clients and customers, and I always love when I have the opportunity to sit down and have a meal with them. It totally just changes the dynamic of the relationship, and you feel somehow just, “Oh, now we’re friends. Now we’re friends who are trying to help each other out,” versus “I’m the person, you’re my client and I’m your whatever.”
Brennan: Yes. I think developing that relationship goes a long way. We talked about this a little bit too, and my default pattern is to just inherently trust people. But we’re weirdoes and a lot of people don’t inherently trust everyone, and that trust is earned. A learn thing for me was I’m going to earn the trust of people, and a great way to do that, you have to sit down, catch up, eat food, which to me is like let’s do it.
Derek: Yes. That’s not a normal – for me it’s not – Like I’m just a nerd and it’s not something I easily do, but you can force yourself. Generally, maybe something else to be self-aware of and actually, in general, you’re going to be more successful leading people to more – From where I am I become, but that’s so you have to, one, recognize that that’s a tough thing to do, and then you have to actually go out of your way to start in many situations, recognize that you’re feeling uncomfortable, and therefore are probably stretching yourself and therefore are probably learning. Then it’d be okay with that, and then be able to look in.
Brennan: Yes. I think the reflecting is key. One of the ones that I’ll throw in there that’s been interesting, we talked about one. I think we’ll do in another podcast, but one that’s been interesting for me is just being vulnerable first. It really helps build trust. If you do want to get feedback out of someone, you do want to get– And part of that is being reflective enough on yourself to know what feedback you’re currently working on. You have in your own management skill, but to say “Hey, here’s something I’m trying to get better on, where else do you think we could work on?”
Jillian: So bureaucracy hacks, we’ve got break bread, be vulnerable. I think there are two good ones, and that’ll help you build the trust that you need to move up. What about building trust? You’ve had an interesting trajectory with your career where sometimes you’re building teams and sometimes you’re inheriting teams. I think a lot of our listeners would be interested to learn a little bit more about inheriting teams. That’s a huge exercise in building trust. Can you talk to us a little bit about your experience high level to start of inheriting teams?
Brennan: Maybe even break it up too, because you’ve done inheriting a team, but then you’ve also done coming in as an executive and inheriting your team.
Derek: For most of your listeners, maybe there’s probably two patterns that would probably be most common. One is getting promoted above your peers, you have some peers, and then also going in from the Sun. I get someone saying, more is like, “I’m from the Sun and I’m leaving this.” It’s different on both sides. I think the main thing that you, and now I try and have as much discipline as I can as possible, but articulating and understanding what the objectives are. Like what needs to be accomplished by it? Why are these people here? Why are you all there? What does success truly look like?
And don’t try and bite off the 12 months from now. In the very short term, especially when you’re dealing with a group of people, you have a short window of time to prove to them that you can– And how do you help them. Being crystal clear on the goals running them down, talking to the team, I can only offer that advice because I should have been given it in previous lives.
Brennan: Even walk through those experiences where you feel like you should have been. What went wrong there? What happened, and how would you fix it, I guess, if you go back?
Derek: It’s just like writing things down. I would say earlier in my career, and even to this day, I’d say one of the best skills you can develop is just writing and communicating crisply and clearly. as I was lucky to have a boss who at the time, I was like, “Oh my God I feel like my homework’s getting marked.” He would teach me, taking out this red pen and marking up what I’d written. I was like, “What the hell is going on?” That again was also a good thing about being on CBC surrounded by people who were journalists, they know how to write.
The best managers there can communicate like crazy. The best lawyers that I’ve worked with over time are monster writers. They can take a lot of information and distill it down, and quickly get that message across. Anything you can do to develop that, and I had people who were beating me with a stick about how I was communicating, and I find most of what I do these days is helping people articulate, trying to accomplish on paper. Projects and teams go off the rails when they don’t have that articulation.
Jillian: Yes. I’m guessing it also helps you build that trust. If you could clearly articulate here’s what my understanding of our goals are.
Derek: Yes and here’s how you can help. Is there anything in your way? I guess another key theme and bureaucracy would have to be removing roadblocks, but you can’t remove the roadblocks–
Brennan: If you don’t know what they are.
Derek: –if you can’t see them, and you don’t know which direction you’re trying to go.
Brennan: What questions then do you use with your team to understand, what is success look like for them? What are they trying to accomplish? What are the roadblocks? What are your go-tos?
Derek: It depends. Depending in every organization and it changes over time, so I don’t think there’s a template that you use to do that. What I was saying at the beginning, I think if you’re in the early days, you have to look at very short-term, how can you drive improvements on results. Figure out what the roadblocks are, what’s getting in the way.
That’s why things like the practices that have come out of the whole agile project movement. That’s how they help because it’s like you get those rituals in place where if you’re listening, they’re people saying they’re blocked and you can look at the patterns, and you’re doing retrospectives and talking. You can find those things and try and figure out what is in your control to help change and improve.
Jillian: Things like the morning stand-ups, the one-on-ones, the project retrospectives overall.
Brennan: Yes, and its making space as a manager to– I think we talked about when you first become a manager, it does become your job to make time and make space to make sure those things happen.
Derek: Yes.
Jillian: That’s precisely your docket.
Brennan: Yes, it’s hard the first time you do it.
Derek: You’re going to screw it up all the time, and you’re going to have some people where– I have a list of people who would sing my praises I’m sure, and I know there’s many people I’ve let down over the years. I still feel bad about it and regret most things. But at least I try to not repeat, I try and find new mistakes to make with people.
Jillian: Great. We’ve learned a lot of cool stuff, and now it’s time for our favorite segment, the secret question, I love so much. If you want there are three cards in front of you, pick one up. He’s going to pick up at random, you can’t see the questions. You could read the question out and then give us your best answer.
Derek: I’m terrified.
Jillian: He picked number two.
Derek: What’s the most important decision you’ve made as a leader? I’ll give you the toughest decision that I’ve had to make a few times. It’s a regular pattern that comes up for technical people. There’s been several instances where you’re new to the team, and everyone hates the software they’re working with. They all want to rewrite it, it’s the worst idea in the world to say yes to that. If you’re a technical leader you’re going to have that.
I’d say the most important decisions as a CTO that I’ve been involved in have revolved around what to do with the– Enabling the legacy environment, when in fact it’s the wrong way to look at the question. You should be thinking of what’s the best way to improve through– What’s the best way to improve the output of the revenue engine of the company? That’s where you should be focused on.
Jillian: Let’s rephrase this question.
Derek: I say the first times I was involved in that, we screwed that up and watched it go sideways.
Jillian: Is it because you said, “What would you like to change?” And then let them go.
Derek: Worse, we need to rewrite that.
Brennan: Yes, you were telling them let’s do that. How much work is involved.
Derek: You’ll end up in an incredible pressure cooker. There’s actually an amazing book called Soul Of A New Mission that I think everyone who works in technology should read, because it’s a war story of computer development from the 1970s. Everyone thinks their challenges these days are like new and art. The guy who’s at the centre of that story is trying to get a 16-bit computer into market in time.
He actually goes through this whole process, and he builds an amazing team, and he finds the way to actually get something which is how to adapt the existing 8-bit and just extend it. It was an incredible idea at the time, but if you read the whole book there’s tons of gems in there including how did it actually do project management that scale and stuff. If I had read and understood that, I would have been able to recognize the pattern.
It’s in front of me, and so coming into Flight Network which has 10-year history, I call it an overgrown start-up, then there’s a lot of pressure to rewrite and rebuild systems, but you got to figure out which one is going to– You have to make sure you’re asking the right question and you’re solving the most valuable problems.
Brennan: If you get someone in there that’s adamant. We talked about this too with inheriting teams. Sometimes you’ll be competing with someone to inherit the team and you’ve been out, or you come in from the Sun and inherit the team, and this person might already have formed opinions, strongly formed opinions about–
Derek: That’s everywhere.
Brennan: How do you handle that person?
Derek: You have to talk to them about data, and you have to make them understand the right question to be asking. Time pressures and everything else kick in, and you are more than likely not going to be successful. It’s very hard to get people to change their minds, and you have to find different ways to show results. I had variable amounts of success, but I still believe pretty strongly that it’s absolutely the right thing to do to make sure you’re asking the right question, and putting the energy into the right things. Often the diagnosis of what’s at the root is probably wrong. You’re looking at the wrong bottleneck.
Jillian: Interesting.
Derek: As a technical leader that’s the biggest one that comes up.
Jillian: Before we leave you, we just want to pass the mic over to Derek for his quick pitch.
Derek: Hey, thanks for listening. At Flight Network, we have an exciting team to work on here in downtown Toronto now. We just moved to downtown from Oakville. We’ve got shiny new offices. You get to work on most of our projects, and customers are actually international. We’re dealing with payments in every currency you can imagine, and flights and airlines from all over the planet. It’s pretty fun, challenging stuff. Check out our job worth. If anyone wants to reach out on LinkedIn, as long as you put in one of those little messages that explains–
Jillian: [laughs] And add a note.
Derek: –I accept it because otherwise then it’s someone trying to sell you services from in the area of Ukraine.
Jillian: Yes, that happens.
Derek: If you want to ask any questions or some suggestions on books to read and stuff, I’m happy to chat.
Jillian: Great. We all heard my meeting minder come up, which means that we’re almost out of time. Thanks for joining us though. That was a really great chat.
Brennan: Thank you.
Derek: Thanks a lot guys.
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