Executive Coaching: How to Choose the Right Coach as a Tech Leader

Welcome to Building Better Developers, the Developer podcast, where we work on getting better step by step, professionally and personally. Let's get started. Well, hello and welcome back. We are continuing our season. We are getting ourselves moving forward. It's the beginning of a new year and sometimes that's a hard thing as you come out of the prior year, but that's what we're focusing on for this season. This episode, we are actually going to start a new conversation and we will give you a little more about that soon. This is the Building Better Developers podcast, also known as Develop-a-Nor. Actually, it's always backwards. It was Develop-a-Nor also known as Building Better Developers because Alexa and those ladies in the box. That being said, I should introduce myself now, Rob Broadhead, one of the founders of Develop-a-Nor, also the founder of RB Consulting, where we help you leverage technology to get your business unstuck and moving forward and look for a successful 2026. Good things, bad things. Good thing is, well, I'll start with the bad thing. Bad thing is we had a slight health emergency yesterday and it turned into something. Being in a new town, a new city and stuff like that, it turned into a little actually new country, new continent, a lot of things like that, turned in a little bit of a challenge. The good thing is, is that even though Apple Maps is not always exactly up to date and steered me to a couple of places that didn't even exist anymore, I was able to finally find all the places I needed to. The good thing is, is like public travel when you're in a big city these days is really easy, whether you're an Uber, a Bolt or whatever the heckin' it you're using, it's easy and fast. When you're like huffing and puffing and sweating too hard, you can hop in a car and get a cab on the way home essentially. One guy that is not going to be heading home anytime soon, because he's already there, Michael, go ahead and introduce yourself. Hey everyone, my name is Michael Miloš, I'm one of the co-founders of Building Better Developers, also known as Developmenter. I'm also the founder of Envision QA, where we design and test software that fits your workload. That way you can stop fighting your tools and start to run your business. Good thing, bad thing. I'll start with the bad thing. Wintertime, Tennessee, wonderful weather. It can be 70 degrees one day, freezing the next day, some of that going on, which unfortunately just makes it for a dreary season. Good thing though, today's a nice sunny day, things are drying out again and it looks like it's going to turn out to be a good week maybe, although they are talking about snow in the next two days, so we'll see. A white Christmas just a month later or so. And today we have speaking with us, Andrew. Andrew, go ahead and introduce yourself. Yeah, hey guys, thanks for having me. I'm Andrew Hinkelman and I'm a certified executive coach and founder of a company called Priority One Group. We focus mostly on executive coaching, one-on-one coaching, team coaching and training with engineers. So my background in the corporate space was in running engineering teams, was a CTO for about eight years at a global financial services company. So yeah, we focus on the human side, so leadership skills, what you call soft skills, those kinds of things that we all need to get a little better at. I'm going to steal from Michael for the good, bad here. The bad in Seattle is a lack of daylight. So people talk about the rain. I'm going to say it's not really the rain. It's not seeing the sun for long stretches of time and that wears on you over time. Good thing, get a couple of trips coming up in the near future. So this is the time of the year where we go south as much as possible, probably make a couple of trips to Mexico if possible. Excellent. Yes, I know that was one of the things years ago that made me leave the Chicago area is it wasn't the cold. It was just that I didn't see sunlight for about eight months and it was just not, that did not work for my psyche or my physique or anything else. I was like, time to go. I need some sun. Let's dive right in because what I want to jump right into like as an executive coach, I think there's something that people sometimes get a little confused about like what coaches can do and when they can come in and things like that. So you're talking to people that are already to some level successful. You know, people would look at them and say, oh, you're successful because you are an executive or you're a leader or something like that. So what is one of the common things that maybe the common themes that would light a fire on or somebody at that level to say, you know what, I need to, I need to get with a coach and see how I can get moving. Yeah, great question. First, I want to dispel a little bit of the executive part of executive coach. In reality, it's just, we don't have a better modifier. We don't have a better adjective. You know, sometimes I'll say leadership coach, which is as confusing, you know. So in some ways it's sort of like corporate coach. It can be anyone at any level, but the main thing really is that someone has something going on. Like maybe they got kicked in the teeth a little bit and a project went south really badly. Maybe they're getting laid off. Maybe there's a merger and you know, they're redundant. So usually there's something, right? Because you know, the reality is you don't need a coach if you are making good progress, if you're happy with where you are. Not everyone needs to work with a coach, but if you have high aspirations or some sort of event going on is probably the indicator where it's a good time to get some confidential, you know, another set of eyeballs on things. Does that mean that you tend, is there, I'm trying to say how to phrase it, but does it mean that there are situations where just that extra set of eyeballs where it's sort of like just come in and do like a, you know, we'll call it like a session or two or something and get somebody to just sort of point in the right direction? Or is it typically going to be something that's a little more of here's the direction and here's how we're going to get you moving forward. So it's more of an ongoing, you know, checking in kind of a relationship. It's usually more involved. So a successful coaching engagement is like, you have some very specific goals and you have some things that make it hard to get there. And it's usually, you know, hidden blocks, things, old habits that you should have let go of already. Takes time to get there, right? Because we're really not that good at knowing what we're good at and bad at and where we're blocked. So you need feedback. So most of the time we start off with some type of like 360 at the very beginning because that's super, super powerful. And that's a great way to make sure that you have a tie into what other people are saying about you. That leads to a good point too. I think some people are like, I need to get my house in order a little bit before I actually have somebody try and coach me. It's like I need to be, I need to be able to go play the game before I could have somebody coach me on how to do it. Is that something that if somebody's just like, I don't even know where to begin. Is that still something that you guys can help with? Or is there something that they should, it helps to do a little prep work before they walk into talking to a coach? No, I don't know that a bunch of prep work is really a good use of your time. Like you, no matter what you're going to come in kind of messy and you're going to, you're going to think I just need to build better relationships or I just need to learn the business. Right. Because people tell you that all the time. But the reality is just like, you know, you need to open up and start, you know, communicating more or, you know, it's, you're going to come in with something either way. So you may as well just come in messy, you know? So how do you kind of find your, find the people that need coaching? What is your like ideal customer that would come to you for coaching advice, for coaching help? Yeah, that's a great question. The ideal really is someone who's new in a role. So you, you're vice president of engineering, you change jobs or you went and got a CTO, CIO role somewhere or something. Right. And you got into that seat and now it's been a month or two and you're like, wow, what did I just step into? Right. This is really great and this is great, but this is not. I'm going to have to focus over here. You know, so it's usually some sort of event like a job change, massive opportunity or something that makes you look at things a little bit differently. Okay. So if, so say I'm falling into one of those roles and I come to you, how do we, or how do you define the coaching role with your customer? Like how do you help them first identify, okay, they're coming to you because there is an issue that, you know, they've gone into a new role, they're struggling with a problem. Lerk, some of the things that your customers would expect from you to kind of, how would you help them? How would you start this process? The reason I'm asking it this way is for instance, you know, for entrepreneurs starting their own business, we have lots of struggles, lots of questions, but how do we know, how do I identify when to come to a coach or look for coaching and what to expect, you know, what would we get out of the coaching if that makes, if I'm phrasing that right? I'm trying to compose this in a way that makes sense. Yeah. Yeah. If we take a founder, for example, a lot of times it's you're, you know, you're spending all of your time on the idea you're building, right? And you're building, you're building, you're building. And then at some point, the operational part kind of creeps in. You're like, we're doing this by hand again, right? Like, or like, why are we living in spreadsheets? Those kinds of things creep in and you start to see some issues, some balls get dropped. The guy who was, you know, brilliant at writing code is also kind of a jerk, right? So you wind up finding out you have some brilliant jerks, your operational maturity is holding you back. You know, there's probably some flacks. And what I like to do with people is just kind of break it all down and kind of say, look, for you, what do you actually want? Right? Do you just want to get out? Do you just want to quick, as quick as possible exit? Maybe it doesn't make sense to clean up everything. Or is this your, or is this your, your 30 year plan? It's time to bring in some operational maturity. But another answer to your question, Michael, really is that it's going to come down to the person. So the thing that we have to remember is some things are going to be easy for you and some things are going to be hard for you and they're going to be different for someone else. And if you say why, there's some sort of belief in there. Some people hate public speaking, but for other people, it's super easy and natural. Like what's going on in there? Right? There's some sort of belief that we want to uncover. And that's, that's the real value of coaching. Okay. That makes a lot of sense. And we talk about a lot about the why, you know, why are we building the companies that we're building? You know, what is it that the customers want? Always that why. In your experience with coaching, what are some of the most common mistakes that you see people make that a coach could help them correct course quickly? You know, because a lot of us as business owners, we have blinders on, you know, we get in our business and we stop focusing on the business or vice versa, and we kind of get stuck. What are some tips or advice that you could offer to say, hey, you know, you need to reset or you need to pause or hey, go look for help from like a coach. Well, I think, you know, I'd be curious to ask you guys this too. You know, in my experience, the most common area where we get stuck is that comfort zone. Right? So if you're a technical person and you start a business, you know, of course you want to wake up early to build and do and, you know, create the new customer journey you dreamt up and whatever it is and build and produce and have something to show people. You might not want to pay attention to cash flow. You may not want to pay attention to this person you got on Upwork, which is just draining your bank account. Those kind of things that creep in are probably where people get held back the most because at some point, the thing you're really good at winds up kind of taking over and can become a bad thing. Right? So I'll give you a really concrete example. I do an emotional intelligence assessment with pretty much everyone that I work with. And for your typical engineer, problem solving and reality testing are super high. It probably doesn't surprise you that a lot of times interpersonal relationships can be really low. So if you're super, super into problem solving, you may not want to mess around with people. And that can be the kind of thing where like your comfort zone, your strength, your superpower is actually depressing other skills that you need. Similar to the comfort zone thing, it can get in your way. Yeah, we had early on in my career, we had a pseudo joke that we had in a development team. We were building software, small company that we get a lot done if the customers would just get out of the way. It was one of those that was like, we had a product, we were supporting customers and that was a large portion of our time. We're like, wow, if they would just let us work, we could get some stuff done. And it was a little tongue in cheek, but there's also, I think that is a common challenge. I agree 100%. I think the most valuable way anybody can get themselves moving forward and expand out of that is that whole idea of like eat the frog every day. Start with the thing you don't want to do and get that thing done and out of the way. And one, a lot of times you find it's not as bad as you thought it is. And two, at least now you've gotten that out of the way. And for me, I love it because then it's like, that's my reward is I get to go do the stuff I like because I got the stuff done that I don't like, got that crap out of the way. If somebody's thinking about, because you touched on a couple things about the person and being, we'll call it, you didn't say it, but I'll call it like being coachable. And if you think of famous coaches, there are some that get along really well with certain people and some that didn't with others. So if somebody's looking for a coach, what would be some, maybe some questions they would ask or some things they would want to look for in trying to find somebody that is a match for them? Yeah, that's first of all, I mean, it's a great topic and you want to shop around, you know, for lack of a better phrase. You definitely want to talk to as many people as you can because you want to find someone who's going to challenge you. You don't want someone who's going to agree with you and sort of placate you. You can use chat GPT for that, right? It'll agree with you plenty. But you want someone who's going to challenge you and push you out of your comfort zone. And so I think you want to talk to as many people as possible and talk to people that have worked with them. There are some core questions that you probably want to ask. And the main one is just, hey, can we just do a coaching session? Like I just want to experience it because there are some coaches who will kind of funnel you right to sales discussion. And you know, it's like with all people, sales becomes a thing, right? And some coaches are really good at it, but it may not be what you need. What you really need is like, hey, can we just take an hour? Hey, I'll have a topic that's important to me. And that's right. And then, you know, hopefully you can get a good feel for whether they challenge you and push you. And if you hang up or you get off of Zoom, you're like, whoa, that was tough. That person just like, you know, almost made me cry. So based on that, that kind of brings up an interesting point. So what are some of the ideal coaching experiences you've had and what are some of the bad experiences you've had? Can you give us an example of each end of the spectrum? Yeah, the bad ones are that a lot of my clients, I have corporate clients who, so let's say I come to an agreement with like CTO and he's like, hey, I want you to coach five of my people. And they hand me someone that I don't have, I don't necessarily know or I haven't screened. So this used to happen to me a lot more. And I've come to find out later that they're like on their last leg, like they're on a pip there and that the company was thinking about this as a rescue. And I'll tell you that for coaching, hiring a coach to rescue someone who is already a poor performer is a complete waste of money, 100 percent waste of money. Like it's not going to happen. And I've gotten on to Zoom or on the teams before and the person doesn't show up, come to find out 20 minutes later they got fired. So those are the tough ones right there. The amazing ones are people who are already in personal development. Right. So the winner, the great sort of box top to the right, the way I'm sort of doing it, is like someone who is already working on themselves. I don't have to convince them that, you know, that you need to read more books about, you know, personal professional development. I don't have to convince them to go by a journal so that they can write out their thoughts and see all of the crazy thoughts going through their head. It's like they're already there, you know. And then from there we can go a lot further, but there's a bit of a perfect client and there's somebody who's already working on themselves. What about those that are kind of in between that those that have been going through a lot of self-improvement or improving, trying to grow, but they kind of burned out. They're not like at the bottom end. They're not trying to walk away, but they're just spinning their wheels. They're not going anywhere or they just kind of plateaued. And you get into like that hyper burnout tentative where it's like you're hyper focused on something, but you're not going anywhere. Yeah. So there are a couple of things around that. One is, so Rob alluded to this eat the frog concept, which Brian Tracy wrote a book about. He's a he's a guy that kind of made a popular error. He also Brian Tracy also has some other books where he talks about a keystone goal. And the idea there is like you have all these goals, but which one of them is going to make all the other ones easier. Right. So when you're spinning your wheels and you're getting up early and staying up late and working weekends and all that kind of stuff, and you're not seeing progress, a lot of times you're doing all the work, but you're not doing the work. You're not doing the thing. And it can be hard to identify what that is, but you kind of need to pause and take and take a beat and kind of go. Of the things I should be doing, if I could only do one, look, what's going to make everything else easier. So that's one, one piece of that. The second piece I'll add is a lot of times when we get stuck, we especially in the corporate space, because we're caring too much about stuff that's out of our control. And this was one of the things that drove my what I got really burned out like 10 years ago. And and I why wasn't I invited to that meeting? Don't they know I need to be there? You know, why did someone have that tone in their email? You know, why do I have to go and fix this? Like, it's sort of like caring too much about all the other stuff and especially stuff you don't control. That was a sure that was like a fast path to being unhappy. And that is part one. Thank you for hanging out with us. Don't worry. We have a part two coming. Andrew is some really good. It feels like a coaching session. This whole like this this interview feels a little bit like it is very to me, very calming, very like, hey, here's some cool things to think about. Here's some things that may be, you know, your some blockers or things like that. So hopefully this is helping you as well. We will have links as always. We'll have links in the show notes. So reach out to him. He offers a free coaching session. If you don't you're like, what is this coaching thing about? Connect with him. Give him a call. Check it out. See where it goes, because I will say personally, I've done some of these in the past and you will. I don't think if you haven't done it, I don't think it's going to be what you expect it to be. It will probably be far better than you expected. Even if you find yourself not thinking that you're in a situation where you're going to be able to talk about your work with them to get a good coach, it is amazing what they can do for you and what they can they can take you to. And I definitely know a lot of people that will sing their praises and their coaches day in and day out and how they have turned stuff around. That being said, it is time for me to coach you to get on out of here and get back to your day. Go out there and have yourself a great day, a great week, and we will talk to you next time. Your next step forward, also sponsored by Envision QA, they help businesses take control of their software by focusing on what matters most quality, reliability and support you can count on. Find out more at EnvisionQA.com. Thanks for tuning in to the Develop the Newer Podcast, where we're all about building better developers and better careers. I'd love to hear your thoughts or feedback. So drop a note to info at DeveloptheNewer.com. Be sure to subscribe on Apple Podcasts, YouTube, or wherever you listen. And remember, a little bit of effort every day adds up to a great success. Keep learning, keep growing, and we'll see you in the next episode.