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Coaching for Leaders

20 Aug 2026 · 21m · 9 chapters

Episode artwork

The Power of Learning from Peers, with Dev Baldwin

In short

How learning from peers accelerates leadership growth, especially when challenges shift from technical work to people skills like communication, delegation, accountability, and tough conversations. Dev explains how the Coaching for Leaders Academy uses cross-industry peer groups, trust, and structured “accountability” to create small, consistent actions that compound over time.

Guest background

Dev Baldwin is a Coaching for Leaders Academy graduate and long-time podcast listener (~12 years). Professionally, he was Director of Technology at Letterfest for three years, brought in to make the tech stack scalable, leading a transformation that moved from technical issues to marketing and growth.

Key claims

Peer learning works best when peers are outside your sector; accountability is support, not finger-pointing; small daily actions (“consistency over intensity”) drive lasting change.

Notable examples

A 90-day plan with weekly action check-ins; refining an action from “after lunch” to “before a meeting”; using community support after redundancy for connections and interview coaching.

Written by AI. May contain mistakes.

Chapters

0:25

Dev Baldwin's Journey to Leadership

Dev shares his experiences and how he found the podcast.

“I'm here today talking with Dev Baldwin.”
3:36

Leveraging Peer Relationships

Dev discusses the importance of peer relationships in leadership.

“What did you hope to gain from this experience when you were considering it originally?”
6:15

The Value of Diverse Perspectives

Dev explains how diverse perspectives from peers enhance problem-solving.

“It doesn't matter how great a group of colleagues you have, it's just really hard to be objective, as objective, when it's someone you work with every single day and you always have to be mindful of the politics.”
8:16

Behavioral Challenges in Leadership

The discussion turns to common behavioral challenges leaders face.

“And I think it's really a powerful combination, those two.”
10:04

The Role of Accountability in Growth

Discussion on accountability and its importance in the Academy.

“The key difference generally is the type of organization you're working in and what you need to do to affect change.”
11:15

Practical Steps for Sustainable Growth

Dev shares insights on making small, sustainable changes in leadership.

“And what accountability really is, it's another, in our context, it's another word for support.”
14:00

The Importance of Small Changes in Leadership

Learn how small, incremental changes can lead to significant improvements in leadership effectiveness.

“aspirations like actually get in the way of them getting started because they want to do so much.”
18:08

Dev's Transformative Experience

Discover how Dev changed his perspective on change through his experience in the academy.

“Thanks for taking the time to share your story with all of us.”
18:34

The Role of Community in Leadership

Explore how relationships and community support can accelerate leadership growth.

“Dev used the word shortcut a few times in this conversation.”
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Transcript

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0:06Hey, it's Dave from Coaching for Leaders. Today I'm bringing you a quick chat about the power of learning from and through our peers. I sat down recently with one of our Academy graduates, Dev Baldwin, to talk about how he leveraged peer relationships to move forward as a leader. Here's our conversation. I'm here today talking with Dev Baldwin. Dev is one of our graduates of the Coaching for Leaders Academy, has also been a longtime listener to the podcast. Dev, so wonderful to have you on. Thanks for having me, Dave. I'm really excited to be on. I've listened to this podcast for about 12 years now.

0:44I know. Very surreal being on it. It's so much fun to have you on because we've known each other for so long and we've had so many conversations. And I'm just feeling so joyful about getting to share a little bit of your story with our broader community. How did you come across the podcast originally? Do you recall 12, 13 years ago? So, yes, I was in a role where I was slightly frustrated and I knew that I needed to be the change. And I was looking around for leadership podcasts. this would have been around about 2014 or so and and i found your podcast at the time i found one of your earlier podcasts episode 49 i looked it up six ways to lead people without a formal title oh wow that was a while ago yeah in those days the leaders weren't born well they weren't made either there was that part of the intro wasn't there right it was you chatting away about six different ways that people could sort of shape their leadership style.

1:54And there was no guest, which, you know, massive respect talking for 30 minutes on that. It was really a good podcast and led me into the rest of your library. And from there, yeah, contacting you to ask just for advice. Yeah, which is a great lead into where we're going to start this conversation too. Tell me a little bit about your more recent work and yourself and just what's been happening professionally. So recently I was the director of technology at a company called Letterfest and I came into the business when the technical stack needed some attention. The previous owners had built a really good, solid business from, you know, kitchen table up to a large business, but needed to scale it.

2:48And the problem there was technology needed to be scalable. So the CEO brought me in to do that task. And I led that work for the last three years. And we helped that business scale. It became what was a technical problem, became a marketing issue. And that transformation was absolutely fantastic professionally. So many things that were involved in the season of, as you mentioned, it started with a technical question, but so many aspects of marketing and people and growth. And I know some of that is what led you to consider the Academy. And you did decide to reach out to me and apply to the Academy.

3:36What did you hope to gain from this experience when you were considering it originally? So what I was looking for was some other professionals to talk to and learn from. Throughout my career, having worked with some really incredible people, most recently at Letterfest, some incredible people there, I realized that learning from peers is such a powerful tool. And what's more, I think, more helpful about the academy is those peers aren't necessarily in your sector. In fact, you do purposely make it so that they're not. And from there, everything becomes like a management issue rather than like necessarily a technology or sort of ways of building something.

4:31thing. It is all about everybody having these common threads throughout their leadership journey, which is, I have this problem. How can we solve it? And that's been incredible. I'm so glad. And I remember when you and I talked originally of you saying it would be really helpful to get out of just these great group of peers, as you mentioned, and all these wonderful people who have supported me, and it would be helpful to get out of just the organization, even the industry, to get additional perspective. And you said something really big a moment ago, I think, of gaining new peers. Tell me more about that.

5:12What was driving your desire to want to have more of those relationships in your professional work? I worked for myself for a long time at the start of my career, and I was responsible for a lot of the networking so that was going to networking events and talking to people and I started to make some really good professional friends there who you could you could chat to and I found a much more refined version of that in the academy where part of the way the academy works is you get put into a group of your peers and you end up knowing them incredibly well and one of those peers I still talk to today we'll have a phone conversation every two or three months and she'll talk me through things that are going on in her business and I'll talk through things going in my professional life and it's just such a trusted she's such a trusted advisor to me and the same for anyone in that group if they were to contact me we could have a great chat because we built such trust and having people outside of the business you work in to talk to in a confidential environment is just so powerful you can speak in in more in more of an honest way than you would in a professional environment where you're sort of tempering what you say and that's not to say being disrespectful but being purely honest about how you feel things are and what type of help you need and you know that that will be taken as oh let's it's a strength they're asking for help whereas in a professional environment you may feel that you're sort of exposing a weakness which I wouldn't consider it to be a weakness to ask for help but some people will feel that way so having that peer group to rally around and they've got such a wide range of experiences as well it's worth just mentioning that in my group we had someone from a massive company down to somebody who was just thinking about you know starting up a business and we had such a wide group of people that that advice is so varied and you really do get like a full 360 approach to any issues that you're facing.

7:25It's one of the things that I've noticed as well too over the years is there's something really powerful about building relationships and building trust, as you said, with a group of people who have not the same industry background, but have similar experiences or at similar places in their career. And the combination of that, along with them not at all being in the day-to-day, like they're totally disconnected from the politics, from the organization, is actually really, really valuable because you get an objectivity that I think it's just not... It doesn't matter how great a group of colleagues you have, it's just really hard to be objective, as objective, when it's someone you work with every single day and you always have to be mindful of the politics.

8:16And I think it's really a powerful combination, those two. Yes, definitely. People also being a fresh pair of eyes will give you some really obvious solutions that once they've said them, they're incredibly just, why didn't I think about this? But because they're not stuck in the weeds, so to speak, they can come at it from some other angle that you just had not considered. And a lot of people have lived these situations already. And so they've got really great advice. And you'll get such a wide variety of advice. Some of it won't be for you necessarily, but some of it will really stick. And it's just incredible.

8:59One of the things you experienced, and I have so many times too, is when we get to the place in our career that almost all of our Academy members are at, So many of the things that we're struggling with really are not so much the technical things anymore. Like the technical training we've all had, whether it's clinical and healthcare or technology in your case or in a nonprofit world, like all of the work that goes into supporting donors and clients, that work's still really important. But oftentimes there's other people in the organization that are really charged with doing the day-to-day. it's the behavioral stuff that becomes challenging.

9:38It's the people aspects of it. It's the communication, the delegation, the accountability, the tough conversations that leaders are in the midst of. And it is really interesting when getting to this spot in our careers, how many of those things become really similar across industry, across even geography and country, that when you get down to the core people stuff, we share a lot of the same struggles. Yes, definitely. The key difference generally is the type of organization you're working in and what you need to do to affect change. And depending on the scale, obviously, that might be a different thing.

10:17But generally, you are dealing with exactly the same kind of issues. And it's just great to be able to talk it out with other people and feel heard and understood. One of the words that comes up in my work and the academy a lot is accountability. and accountability is one of those words that I think a lot of times many of us have a negative connotation to. I know I have for a while of like, okay, accountability is the kind of thing where you have to sit down and have a really difficult conversation with someone, which is one aspect of accountability. But we talk about that also in the academy and you've shared with me that accountability was something that was really helpful to you during this process.

10:56How did it show up for you in this process and what was helpful to you? So accountability, in the peer group, we put together a plan of what we would like to focus on for the next 90 days. And part of that is refining a plan for things to do throughout your week that can help move the needle. And what accountability really is, it's another, in our context, it's another word for support. you every time you go into the group you will say how's how's your action been how's your action gone have you managed to do it there's no like you have to have done it but have you been thinking about it what's changed we'll all talk about it and then you can sort of change that action everyone can have a chat and say okay maybe you've taken a bit too big of an action but what you're trying to do you should maybe help sort of hone that in and the other part of this accountability slash support is you get paired up with somebody as well and then you can you'd have a reg between the groups you'd have a regular dialogue that you can you can have with that person and if you've getting into any issues or you need some support they're there for you and it's it's so much more than sort of accountability from a finger pointing perspective it's more of like I said just support and knowing that someone's going to ask you about it means that you're definitely going to focus on it it's going to be in your mind if not top of your mind and actually one thing that the accountability does is people ask questions which if you were working in a bubble on your own because you're not going to be able to ask yourselves those like questions that don't come from your own mind they will challenge you as well and that has been really helpful for me Certainly, I think early on, I made a little bit too big of an action for me to do.

13:00And we just honed it down. I kept trying to do something after lunch. And then my lunchtimes were quite variable. And that just did not work. So we refined it down to before a meeting. And that was really effective. We get really tactical in this process, as you mentioned, of trying to make it really simple for each one of us of finding a particular moment in the day where we'll take an action. And the intention behind that is to have consistency over intensity, right? Like nobody in our community has hours a day to work on our development as leaders. I wish we did. Like, I wish we all did have that kind of bandwidth, but just the reality of almost every role that everyone in our community has, it's small actions done consistently that are going to get us there.

13:46And we have all of us like really high aspirations. And sometimes the high aspirations get in our way. Like we want to take on too much. And I've had so many times, Dev, over the years, and you've seen this too, where someone's aspirations like actually get in the way of them getting started because they want to do so much. They have such good intentions of wanting to take on a ton. And then they don't really know where to start. Or they do start over a couple of days, but they put so much time and effort into it that they can't keep it sustainable. And that's one of the reasons that we work together in a community to really help each other to take those small steps because that ends up being so much more sustainable over time.

14:25Yes, definitely. Small steps are so achievable. It's the same as anything, really. You know when something's too big a task when you can't start it because you've made it so broad, it's not very easy to understand where you're meant to start. Whereas with the accountability in the groups, we're asking for something quite small that you would do, a small change at a time that you can remember as a good trigger. And it does make a massive impact over time, even just being aware of it. And to your point about having time to learn leadership, large blocks of time, there's not really a better way to learn leadership than doing it, actually doing the leading.

15:07And if you were to do it isolated in your own time trying to read books, it's great reading the books having knowledge but applying that knowledge is really where the where it comes and the only way that you become a good leader is to be in a lot of situations that go either well or not so well and take that learning and part of what the academy is giving you is a group of people who have done all of this so in a lot of ways you're taking some shortcuts um people have done this with they've they've gone through hiring gone through performance reporting they've gone through structural change in a business they've changed roles into the areas that they're not so sure on they've managed particular types of workers that may need motivation in different ways you've got such a broad range of people that can instantly shortcut at you and want to actually mentor and want to give you the knowledge and time because somebody else has given them the knowledge and time so that's one of probably the biggest i think the biggest win with the academy is not just the sessions which get you into a good rhythm but also the massive community of people who are all so freely giving of their advice and will post questions and you can answer and if anybody wants to jump on a call i've had such great support from from people.

16:32I mean, just recently, I was made redundant from my last role as they downsized the business to improve cash flow. And then from there, I've had so much support from the community, help with connections, help with interview techniques for the kind of roles I'm looking at. So it's been really massive. And everybody in that community is somebody who's trying to improve constantly. And they were all obsessively, not in a bad way, but really like working hard to become better at what they do. And everybody is almost an overachiever in a lot of ways. They are incredible people in the community. You know, I ask people often what they've changed their minds on going through this process, the experience in the academy.

17:23What, if anything, Dev, have you changed your mind on through this? I think for me, the thing I've changed my mind on is the fact that a very, I think, I always thought change came in like a big flood of effort and you have to really push hard for it. But actually the change that sticks is the small change, the small bit of effort. I will just, this day I'm just going to do this a bit differently. I'm just going to make a conscious effort to do this small thing. And that small thing is more achievable. and so over time it compounds to a big thing if you try and do the big thing you will probably not get there and that is such a such a powerful thing i didn't i genuinely didn't think that could be a thing before starting the academy and being part of the community and it's a massive benefit and i would encourage anyone to start small it really will make a big difference just a two or three maybe five minute change you can make a day it's incredible david has been such a joy to support you all for all these years.

18:27Thanks for taking the time to share your story with all of us. And I'm so glad that you're a part of our community. Thank you, Dave. This has been brilliant. Dev used the word shortcut a few times in this conversation. Whenever people ask me about the work I do, I often say something really similar to them because I don't know a better shortcut than great relationships. My job is to help leaders thrive through inflection points. And a big way that works is by helping people move through those points way faster than they would on their own. How that happens really comes down to what Dev said throughout this conversation.

19:03Community, relationships, working with other leaders who also have high aspirations for themselves and also who care a lot about helping other leaders grow. That's because when you get to the inflection point in leadership where most of the job becomes about the people stuff and less about the training in your discipline, so many situations become similar for all of us. Managing the daily chaos of meetings and schedules and holding people accountable and navigating conflict and establishing a vision for change and getting people to buy into it and developing those people and defining roles and giving feedback.

19:40Those are almost universal challenges for most leaders, and we're all working together in our academy to help each other get better at all of them. If you're also at an inflection point right now, I'm inviting you to consider applying for the Coaching for Leaders Academy. We're opening applications in the coming weeks for just a brief window for the final time this year. Go to coachingforleaders.com slash academy to discover more. And if you get to that link before applications open, you'll see a place there where you can request an early application from us. And you're going to find lots of detail on that page as well about structure of the academy, how it works, and also the process for applying.

20:23The Coaching for Leaders Academy helps leaders thrive at key inflection points. Head over to coachingforleaders.com slash academy for more. Thanks as always for listening in and watch for the next regular episode this coming Monday. Take care.

From the publisher

Academy alum Dev Baldwin joins Dave to share how he leveraged the power of learning from peers.

Are you at an inflection point? Apply to the Coaching for Leaders Academy by Friday, September 11th.

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