· 25 mins · Management Skills

What we learned during season 1 of the People Leading People podcast

We can hardly believe that only a few weeks ago we were introducing the world to the SoapBox podcast, People Leading…

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We can hardly believe that only a few weeks ago we were introducing the world to the SoapBox podcast, People Leading People! Now here we are, hundreds of listens (and plenty of five-star reviews – thanks guys!) later, and we’re finishing up season one. In episode seven, the final episode of the season, we’re talking about all the wonderful things we learned from our guests.

The full episode and transcript are below, but here are a few of our favourite insights from the season.

What we learned from Paul Teshima, co-founder and CEO of Nudge.ai

In short, how to make sure strategic priorities are being communicated across all levels of the organization. Paul says it’s about getting people leaders to get their employees to ask the questions they (the people leaders) are asking the CEO.

What he means is, as a manager, your job is to give people context about the business and make sure they understand how the work they’re doing impacts the bigger organizational goals. If you’re doing that right, they’ll inevitably start asking you the questions you’re asking the CEO because you’re all marching to the beat of the same drum and have the same understanding of what’s important to the business.

It’s about getting your team to the same place you’re at in terms of information and understanding about the company’s vision, mission, goals and strategy.

Listen to Paul’s episode to hear more about how he has inspired managers to become some of the best people leaders in the Toronto tech scene.

"It’s about getting your team to the same place you’re at in terms of information and understanding about the company’s vision, mission, goals and strategy." – recapping @paulteshima of @NudgeAI on the #PeopleLeadingPeople podcast Share on X

What we learned from Alyssa Furtado, CEO of Ratehub.ca

Alyssa gave us some awesome tools to communicate information from top of the organization to the front line. One of our favourites was Rock Setting.

The idea here is to decide on a small number of “rocks,” or priorities, that the company determines are the most important things to focus on to achieve success. The process of setting – and sticking to! – rocks helps everyone prioritize their work and ensure only the most important things for the business are being focused on.

Listen to Alyssa’s episode to learn how they set rocks at Ratehub.ca.

What we learned from Derek Marshall, CTO of Flight Network

With Derek, we took a bottom-up perspective – how an individual contributor can better understand the system they’re working within.

We talked about the “bureaucracy hacks” people can use to if they’re struggling to get their work passed through the bureaucratic system in their organization. This could mean building strong personal connections in the workplace. This could mean removing roadblocks for people. And it could mean being vulnerable and sharing your growth needs, so that others feel comfortable doing the same with you. 

Listen to Derek’s episode for all the hacks, and tips for building trust with your team.

"We talked about the bureaucracy hacks people can use to if they’re struggling to get their work passed through the bureaucratic system in their organization." – recapping Derek Marshall of @FlightNetwork on the #PeopleLeadingPeople podcast Share on X

What we learned from Mike Katchen, co-founder of Wealthsimple

With Mike, we talked about job mapping at Wealthsimple, and his philosophy about letting people remain individual contributors if that’s what they’re really passionate about.

Mike knows not everyone wants to be a manager. And when you think about it, it’s not surprising. Being a manager is a career change: suddenly, instead of focusing on the skills you’ve worked so hard to master, you’re being asked to coach others to do that skill. Essentially you’re being asked to be a psychologist, a motivator, a people leader. So, Wealthsimple has created alternative career paths that allow people to move up in seniority, title and compensation, without having to move into the management track.

Listen to Mike’s episode to learn more about Wealthsimple’s career paths, and how Mike scaled people management at a rapidly growing company.

What we learned from Johnathan and Melissa Nightingale, co-founders of Raw Signal Group

A big thing we learned from Johnathan and Melissa is that if you’re looking for ways to coach managers, understanding where they fall on the relationship versus results scale is helpful.

Every manager falls somewhere between the two extremes. Do you care more about people’s feelings than giving them clear feedback? Or do think personal conversations get in the way of getting sh*t done?

Neither is necessarily better than the other, but it’s definitely not a good thing to be at either end of the continuum (100% relationship or 100% results). Whether you’re on an extreme or right in the middle though, the important thing is to be self-aware and intentional about the way you manage.

Listen to Johnathan and Melissa’s episode to hear more about the relationship versus results spectrum.

Check out our final season one episode below – and scroll down for a full transcript. And stay tuned for season two of the SoapBox podcast, People Leading People! Be sure to subscribe in Apple Podcasts or wherever you listen (and we’d love for you to give us a ⭐️⭐️⭐️⭐️⭐️ rating!).

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Happy listening!

People Leading People episode 7 | What we learned in season 1 of People Leading People (transcript)

Jillian: Okay, cool guys. Welcome to the last episode of season one of People Leading People. Today, Brennan and I just want to have a chat about the things we’ve learned this season. Hopefully, our learnings are helpful for you guys. We’re just going to talk through the different episodes and the things we liked from each of them.

Brennan McEachran: I would love to invite you to do the same. Reach out to us, and share what you’ve learned or what you’ve applied. I think that’s what I’ll try to do. What have I applied to SoapBox based on these conversations?

Jillian: Yes. Also, cool new idea too. If you wanted to leave a comment with your favorite episode, even if you just say the name of the person who was in the episode, so that we can be directing people to the best, the top episodes of the season. That’d be great.

Love it. Well, we interviewed a lot of great leaders this season. I think we learned a ton from all of them, but let’s talk about Paul Teshima. We interviewed Paul a little while ago. One of the things we talked about with him was as a CEO, what he thinks about a lot, is how does he get his leadership team? To get the people that they’re leading, to ask them the questions they are asking him.

They come to him with questions about the business and contextual things, and he always says, “Well, you need to get your team to ask you those questions.”

Brennan: That’s the one that stuck out for me too. The other thing is just reflecting back. Paul’s a great storyteller. The stuff that sticks out is these personal experiences he was able to share with us. That’s the one that stuck out for me too, is him saying in his one-on-ones, and he says this over and over again, “You’ve got to get your team members, you’re going to get your employees to ask you the same questions you’re asking me.”

When you think of it that way, and you think of all of the work that would take in order to get your individual team members to be at the same state your brain is at currently. To ask all of these different questions to your boss, then that’s really kind of scaling yourself or scaling leadership or scaling the context and spreading the information you just read. I think the reason why that resonated with me so much is that’s such a daunting ask of somebody. In such a really simple way to say, “What do I have to do in order to get my team to be at the same place I’m at, in terms of information and understanding?”

I love that. That’s the one I use now all the time, not only internally, but also when I’m out in talking with managers. With time alone, once you start talking about, “What do you want to get at? How do you want to scale?” You really want to get them, I think up to the same level you are at, in terms of context and understanding. That’s the goal.

Jillian: Totally, and it is like you said, it is daunting. One of the things that pass through my mind when I was thinking about that was, “Don’t you want the people on your team, as a leader, to be really focused on the things that they need to accomplish? How do you balance making sure that they keep their head in the game with what they’re meant to be focusing on, versus understanding the greater context?” All these kinds of things.

I think when we were chatting with Alyssa Furtado, she had a really great tool. She talked about a really great tool called rock setting that really brought that home, at least for me. Maybe you can talk a little bit about it. That was interesting.

Brennan: Alyssa’s great. We actually follow– and if you actually listened to the episode, she said she brought in a facilitator. You don’t really have to do that in order to start taking some of these learnings. There’s great books out there that basically talking about the same thing. Traction is one that she used, we use.

Scaling Up is another one, that’s the kind of like Rockefeller Habits 2.0. It is complicated, but I think step one is to recognize that that’s now your job as a manager. Then, step two is to bring that context. To break some of these problems down into understandable chunks that can be spread.

The EOS system or these different systems are really a smart, helpful way to think about it. When you think about, “What am I going to talk about one-on-one, what I’m going to talk about at the team meeting? How are we going to do these quarterly plans?”

As first time managers, you look at all of these discrete events, and you’re, “Wow, this is a lot of time in meetings and stuff.”

Jillian: It’s a lot of work. It’s like, “Do I have to start from scratch each time we start thinking about all these different things?”

Brennan: “What do I do here? What do there?” The helpful thing for me that those tools provided is just a way of thinking about that as a system. Your vision and mission statement is helpful because it’s something far away that’s really ambiguous. But it helps you set, “What does that look like in 10 years? What does that look like in five years or three years?” Those three year plans help you break down to, “What’s my quarterly goals? What are the big things I want to accomplish this year? How do I break that down into four discrete chunks?”

Call those rocks, call those OKRs. We call them OKR’s, even though we basically follow Traction. Call them whatever you want to call them. Those are the four things or the four unmovable goals that you’re going to try to accomplish this quarter.

Then your weekly meeting, if it’s a level 10 meeting or however you want to think about it, is really just 12 opportunities to check in on the progress of those goals. Would you rather check in on the progress of those unmovable, very important goals, once a month? You get three opportunities to see if you’re going to hit them, or do you want to do it 12 times? Or if you going to do it biweekly, do want to do it six? For us, or the way I think about it is like, “Well, that’s just 12 opportunities to reset course and fix problems before they become problems.” I love those books. I think she did a great job of describing how it works within her organization.

For thinking about, “How do I break out these really important, dense goals, objectives and things into discrete events, that all, I think, connect and ladder up and share knowledge?” Really create this feeling of momentum and progress towards that, which is really important for a team.

Jillian: Exactly. It’s kind of, “How do you project manage your business strategy? How do you take this big thing that you’ve got, this huge project you have to do–? It’s a huge goal. How do you break it down into individual tasks that you can check on regularly?” That’s really what it is.

If you’re looking for a way to scale your strategy or learn more about different systems like EOS, the Alyssa episode is great. You should go back in the feed in and have a quick listen.

Brennan: Exactly. And I think that the other thing is that sometimes when we talk about these things, we talk about them company-wide, just because of who we’re talking to. That doesn’t mean that they have to be company-wide. You can do this within your team. You can do this within any project or any goal that’s longer term.

Even some of the things that are– say, you have a shorter term project. Some of the shorter term things they do, like the weekly meetings, you can bottle that off at the same thing and get very similar to that.

Jillian: Another thing that we talked about in that episode is that systems like this help relationships between teams and help people understand the way their work impacts everybody else’s work. How everything is connected as a system also within the organization, which makes me think of the conversation we were having with Derek. All about win-wins and bureaucracy hacks. And how shifting your mindset from just being an individual contributor in your box, “I need to complete these tasks.” And kind of taking that step out and saying, “How do my tasks impact the success of everyone around us?”

Brennan: No, it’s almost like it’s a different look at the same system. A top down look is like, “Oh, we have these EOS systems. We follow these methodologies.”

Jillian: How do we get something from the top to everybody?

Brennan: Then, Derek was great at like, “Hey, here’s how I discovered that in reverse.” I got my head out of my task list and started looking at, “Okay, I’m actually a part of this system, but instead of code, it’s now people. What are the hacks that I have at my disposal in order to get work done faster, but more with management hacks versus just typing code faster?”

I’ve used a few of them. I shared a few of those that I think are super valuable. The one that sticks out, all other than food, which is I think really important–

Jillian: Yes. Derek talked a lot about how important food is. If you’re into food and meetings, check out that episode.

Brennan: Yes, but the one I think is really valuable for new managers is just thinking about win-wins. You’re thinking about your goal. Someone’s giving you this goal. You’ve got to lead a team to achieve this goal. Sometimes there’s frustrating things that appear. I’m like, “I can’t do this because this person’s doing that, or I really want to do this, but these people are telling me–“ All these parties are shifting.

To think about like, “Okay. How do I create a series of win-wins throughout the organization?” I remember I was chatting with a lady here in Toronto, and her task was making user onboarding better. She was having a hard time because success wanted something, sales wanted something else, founders wanted something else. She was pulled in all these different directions.

Jillian: It happens all the time.

Brennan: All the time. The CEO comes in and squashes things.

Jillian: Where’d you come from?

Brennan: What was neat with her and chatting with her, it’s just thinking about it with win-wins was, it’s not just her little micro world of each individual user. “How do I onboard each individual user?” It was thinking about onboarding. Breaking those users up into different segments and then creating win-wins.

How does she create a win-win with her team, and the sales team, and the CS team. When we talked about it that way, I think it became really clear for her: Oh, user onboarding includes those sales sandboxes or those sales trials. If I can set up a trial to be super successful without the salesperson doing anything, the sales team’s going to love it. That’s going to help us make more money. The CS team as long as it’s set up properly, it’s going to love it as well because that whole customer is going to come to them basically set up, 95% properly. That was a great thing for her to go off and tackle right off the bat. For sure, great onboarding better, but create a bunch of winds up in the process.

Jillian: The great thing about something like that too, with that specific example is that it gives people from these three teams that perhaps are working in silos, a chance to come together and work on something together and really put the customer first. I think it highlights the fact that a customer’s experience– I think when we work for companies that build apps, it’s very easy to get lost in the– a customer experience is their experience in the app.

Really for a lot of at least B2B software, there’s a ton of stuff that goes on outside of the app that lends to the customer experience, and at the end of the day lends to whether or not they’re going to be renewing. I think when you can find projects in moments like that to bring all of those teams together, the ones who are directly high-touched, talking to customers, and the ones who are the more low-touch experience. When you can find ways to melt those together, I think that’s when you really are putting the customer first because you’re trying to think end-to-end, what are all the touchpoints this person or these people have with our organization?

Brennan: And I think Derek, to me anyways, put it in a really good way in my brain. Which was, connecting these people in meetings, at first you’re like, “Uh, more meetings,” but the way he was thinking about them as, “Sure, meetings, but meetings are hacks.” That’s a way you can connect these two people who otherwise aren’t connecting. Bring them together and get your work done faster. If you didn’t do that it would take three months. If you can sneak away to hack a room full of the right people, get them talking about the right thing and get agreement really quickly, by the end of that meeting, like “Wow.” You can save yourself tons of time.

Jillian: Totally. It was cool to hear, like you were saying, his stories about starting as an individual contributor and working his way up to management. Lucky for him, he loves being a manager and it really was where he shines, but for a lot of people the move from individual contributor into manager is a really, really stressful time. It’s something that not everybody takes very well, because if you’re a great coder, doesn’t mean you’re a great psychiatrist or a great coach or a great whatever, which is what you’re being asked to do when you become a manager. I think Mike Katchen from Wealthsimple had a lot of really cool things to say. I was really intrigued by the way, sort of the philosophy around job mapping at his company. How he lets people continue to be individual contributors if they’re crushing it and that’s what they’re meant to do versus forcing everyone down this management path.

Brennan: Yes exactly. And I think, every time I think back to Mike. Mike is the most thoughtful person. When he thinks about career progression, he’s really thinking about it being as thoughtful as he can to each individual employee. That just shows through the company he’s created, and the systems that exists there. What’s best for the person and what’s best for Bob in engineering might not be this fast-paced, charismatic, extroverted management path.

It might be, let’s give him the responsibility, and give him the authority, and give him the pay raise, and all of these things that normally come with management, but put it to the skills that he or she wants to develop. That’s not something that we I think necessarily can implement today here, but it is something that we’ve talked about. When the time is right, that’s exactly how we’re going to do it. There’s a few books that talk about it deeper like Radical Candor actually does talk about rock stars and superstars.

If you are thinking about, “Okay, how do I set some of these things up?” You can do it within your team too. It doesn’t have to be this company-wide effort. When you’re thinking about coaching employees you’re thinking about, who do you give projects to, or who do you give a little bit more autonomy to? Think about it in, what’s going to be best suited for their skillset, or I put on my cap, just be incredibly thoughtful on the person.

If they’re great at management, awesome, let’s let them flex that muscle, but if they’re really great at their core skillset, let’s let them flex that muscle and not necessarily force them into this muscle they don’t want to be in.

Jillian: Totally, it is so interesting too. I mean, obviously, we’re always thinking about strengths and weaknesses and where do you fall on this spectrum and that spectrum and the other spectrum. When we were speaking with the Nightingales, Melissa and Johnathan, we talked about the relationship results. I thought that was so much interesting and still I think I think I just fall in the middle. I’m usually like a very gray area person, but it’s an interesting way to think about a person, whether they’re on your team or they’re your manager or whatever.

It’s a new avenue if you’re looking for ways to coach, and coaching to me is a very daunting thing and understanding like, “How do I even dissect what to coach in someone?” To me that shifted my perspective a little bit and gave me another thing, “You could coach on relationship versus results.” I thought that was interesting.

Brennan: I think it’s also, for me, it was really easy to go like, “Oh shit, where do I sit, how do I get better?”

Jillian: Yes, what are things I can do?

Brennan: I’m probably more leaning towards this side, so that means I have to work a little bit harder to actually go a little bit farther over here, but probably that’s where I should be. The interesting thing right off the bat, I remember like a week after that episode I had a reference call. And I think the interesting things with reference calls are – one, I think reference calls are important like you should do them. You’re hiring people, you’re not doing reference calls, it’s not only shame on you, but man, you’re missing out on so much key information. Even if you’re like already set, I’m going to hire this person, think about like, “Hey, interviewing that person’s previous managers on how to manage them better.” At least do that.

Jillian: At least so you can have a leg up when they start working with– You already know.

Brennan: You immediately get them into a productive state.

Jillian: You wouldn’t want it to cloud your vision. So sidetracked: you wouldn’t want them to be like, “Now I’m going to paint you with this brush,” just putting that out there.

Brennan: Yes. What I think is hard about reference checks and we definitely should do an episode on it because there are some hacks within reference checks to make them useful and not just stupid. The hard thing is everyone there is trying to sell the candidate. You have this personal relationship with a candidate. They want them to do good. They want them to get the job. They’re purposely to like, not say bad things. How do you get them to say potentially bad things that you want them to raise the red flag and be like, “Don’t hire this person.”

I thought what was really interesting was talking about the relationship to results spectrum. Not saying either one is bad, but I loved how Johnathan and Melissa labeled the farthest of the relationship side of the spectrum being, “Oh, you’re basically just a big teddy bear.”

Jillian: I think they said huggy bear, which I think is adorable, “You’re a big huggy bear.”

Brennan: The results side of things is basically you’re just a big a**hole.

Jillian: Just a mean person.

Brennan: You’re just mean. You’ll burn the relationship bridge in order to focus more on the results. Obviously, that’s not great. Same with the huggy bear, you’ll ignore the results in order to have a huggy bear feelings.

Jillian: Which doesn’t help the business?

Brennan: Doesn’t help the business at all. The reference call happened just after that. I got the sense that this person could get themselves in situations where they were mean and the team just doesn’t like them. I was trying to get a sense–

Jillian: Please don’t hire that person.

Brennan: –of like, “Am I being crazy, am I being insane thinking this? Am I reading between the lines correctly?” It got to the point where I was like, “Okay.” I had this great conversation and they said people fall in this relationship to results spectrum. Results is all about caring about results and not necessarily caring too much about the personal relationships have happened around that, “Where would you say this candidate falls?”

They said like, “As far on results as possible.” This person is 100% results. I was like, “Okay, confirm the person’s an a**hole.” That might not entirely be fair, but it confirmed some of the twinges I got.

Jillian: Yes, you had other things in the conversation that were red flags.

Brennan: Yes, and I was like, is this it? Turns out to be it, and they would have worked with Jill and that would’ve been awful.

Jillian: I don’t like mean people.

Brennan: The thing for me was that doesn’t necessarily mean don’t hire results-oriented people or 100% results oriented people. It came down to, “Do we have the energy as managers to coach that person from being a 100% results to being something more balanced?” I think in the state that we were in for this particular role I didn’t feel comfortable that we had enough energy to devote to managing.

Jillian: This is not the time for our company, we don’t have time for that. I think it’s interesting too because if you think about it from what’s the team we’re trying to build and there will be cases, I’m sure, where you need to balance out your team with someone who is very result-oriented. In that case, that would be the right choice for the team. Like you said before, they’d be working with me and with other people like you were, “That’s not the vibe that we needed. That’s not the vibe that’s going to make that role successful. It’s like that just isn’t what is needed in that role.”

We had a lot of great conversations this season. I feel like there’s tons of stuff to learn. If you haven’t had a chance to listen to the other episodes in the season, go back. Subscribe to the podcast or download the different episodes, the ones that you’re most interested in.

We’re also starting to think about season two. If anybody, if anyone out there has topics you’d like us to cover next season, if you know of leaders that you’d really like to hear from, there’s some information in the episode notes of this episode of how to contact us, to let us know about that. You can also let us know in a review. If you want to leave a review, five stars is always welcome, but be truthful, be honest.

Brennan: I’ll jump in on that point. Like most companies out there experimenting and trying, this podcast is an experiment for us. We’ve heard from a lot of people especially as we’ve been doing this that, “Hey, podcast can really catch on.” No idea if ours will. We’re really treating next season one as an experiment. Reviews are going to be the way that we judge it. If you do like it, do you do want other people to listen to it? You did get value out of it, please do. I know, I’m a person who listens to podcast and hears the plea for review all the time.

Jillian: All the time and sometimes they’re funny and cute.

Brennan: I very rarely do it, but–

Jillian: I do it for the ones that I love. I do.

Brennan: –please do review this one. Five stars is great. Give us your honest review because we might end up doing a season two.

Jillian: Helps us prioritize our work, quite frankly.

Brennan: Yes. Let’s make it better.

Jillian: Make it better. Great, well thanks for tuning in, guys and hope to hear from you in the reviews forum. Cheers.

Brennan: Thanks.

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