[00:00:15] Ghazenfer Mansoor: 

Hello and welcome to the Lessons from the Leap. I’m your host, Ghazenfer Mansoor. On this show, I get to sit down with entrepreneurs, founders, business leaders who talk about bold decisions, pivotal moments, and innovative ideas that shape their journey.

This episode is brought to you by Technology Rivers. At Technology Rivers. We bring innovation through AI and technology to solve real world industry problems. We do this in two ways. First, by helping businesses streamline and automate their operations and secondly, by partnering with startup founders, entrepreneurs, and product owners to create innovative software products from SaaS platform to web and mobile apps.

A big part of our work is Healthtech, where we work with healthtech companies to build secure and HIPAA compliant products. So you wanna learn more about our work? Head out to technology rivers.com and tell us about your product. Today on Lessons from the Leap, we are joined by Steve Dwire. Steve serves as leadership and management coach, helping technical business leaders advance their excellence and avoid promotional remorse.

Throughout his career, he discovered that many technology leaders struggle as they advance. When they become managers, they expect a change of responsibility but they can be surprised by how much their identity must change. They’re surprised again when they have managers as their direct reports.

Each step brings new challenges that take a tall boat on leaders and on their teams. Steve has led software engineering and IT teams in companies running a gamut from startup to fortune hundred. His combination of master’s degree in software engineering, ICF approved coach training and decades of real world experience as an engineer and in multiple director roles makes him distinctly suited to help managers and directors of technical teams succeed as they grow in their career.

Steve, welcome to the show. It’s great to have you here.

[00:02:20] Steve Dwire: 

Thanks so much, Ghazenfer. Glad to be here.

[00:02:23] Ghazenfer Mansoor: 

Okay, so you talk about the promotion remorse. What is it? And when did you first see it show up in your career?

[00:02:35] Steve Dwire: 

The term is really, it comes from the idea of buyer’s remorse. There’s so many other ideas where you think something is going to be wonderful and great and so you go pursue it, you chase it, you buy it. You accept this promotion only to discover this isn’t what I thought it was. Now I’m expected to be, you know, in the case of moving from an engineer into a management role, realizing that everything that made me successful as a technical expert, now getting in the way, and I have to become somebody different to be able to succeed at this new career and I’m not sure that’s really what I wanna do. So many people go back and forth and they’ll  be an individual contributor then they’ll become a manager and then they say this isn’t what I want to, what I cut out for, they want to go back to individual contributor. Sometimes they can, sometimes they can’t, depending on the organization they’re in and when they can’t, that’s the epitome of a promotion remorse.

[00:03:42] Ghazenfer Mansoor: 

Cool. Yeah, that’s a good analogy. You mentioned like the buyer’s remorse and employee remorse as well. I mean humans are all similar. It’s hard to make that change. So anytime there’s a change, it’s always gonna be now we see that in the bills as well. Like you buy a product and then you start thinking, is this the right decision? You sign up for a service, it takes time to really gel and then. We were thinking for the first few weeks, is this the right decision? So yeah, people try and I totally hear what you said because I know talking to some people. A friend of mine went to manager, went back to a  hard, good work and then came back realized because after you go back, then you realize the other one was a better deal. So it’s really, you have to work on it. You have to change it.

[00:04:46] Steve Dwire: 

And what’s interesting is that even remaining an individual contributor when you move back from manager to individual contributor moving along even the technical track many of the same internal changes that it takes to be a good manager, not all of them but many of them are also important for becoming advanced along the technical track in leadership. The whole idea of building relationships, understanding conflicting ideas, and being able to know when it’s your turn to play referee or when it’s your turn just to disagree and commit all of those things whether it’s management or technical track similar things.

[00:05:28] Ghazenfer Mansoor: 

Yeah and then you have mentioned that becoming a manager of managers is a whole new lead.

[00:05:33] Steve Dwire: 

Hmm.

[00:05:34] Ghazenfer Mansoor: 

So can you break down that?

[00:05:37] Steve Dwire: 

A few of the big things? When you are a manager of individual contributors that’s really the first time that you become responsible for representing the business on,  speaking on behalf of the business to your team members and then also in reverse representing your team members back to the business.

But then once you become a manager of managers, now the people that you are leading are now responsible for speaking on behalf of the business. So your role then in how, to what degree to, with what intensity of authority do you speak to those? At the level below, you become different.

There are many more things now that you have to release control over. Allow those leaders who are below you to actually do some leading to do some managing. I remember something that my boss said to me once when I was trying to apply the frontline manager mentality when managing managers.

I was still trying to oversee and make sure that every single project within my entire scope, every project was going to be successful and he told me, Steve, you have to be willing to let your direct reports fail because that’s the only way that they are going to grow and be able to succeed in general and that was something that was very hard for me to let go of and to learn that lesson.

[00:07:22] Ghazenfer Mansoor: 

I think that’s hard for everybody. It’s like letting your direct report fail because that would come onto you or a fear of not achieving goals, whatever are those different goals. So, we humans would like to be perfect and we do see these problems in our business as well.

Some of them with myself, which probably comes managing managers and then people moving up as a technical company. Obviously the developer is becoming leads becoming directors, managers, and then you have to go through this whole process of the struggle because there’s a total different expectation.

[00:08:08] Steve Dwire: 

Yes, absolutely.

[00:08:10] Ghazenfer Mansoor: 

So moving from architecting systems to mentoring people, it’s a big shift and how do you navigate that transition for yourself? Because again me, even coming myself, I can see that it not an easy change, so based on our conversation seemed like this is area you like most now. So Tech, it’s hard for tech people to leave the tech part

[00:08:35] Steve Dwire:

And I didn’t even go with a direct path. I thought when I left my job, I left my job in 2021. I was a, I had been a director. I had kind of scaled back a little bit, went part-time, and then finally left in 2021. But I thought at that time.

That my next step was to be running a software as a service business that I had started back in 2013. I had, you know, built a few things, dabbled in, you know, trying to find the market that I had the market I wanted to serve, dabbled in what product it was going to be. But then the day job just took way too much of my attention, so I left in 21 to focus full time on that deep technical.

I spent hours upon hours, days, months in the weeds technically and realized eventually that I was trying to solve a problem that my target market didn’t really care about and that’s when I hired a coach to help me figure out what am I gonna do with this? Because this software as a service, it’s not failing technically.

It’s failing businessly, the market, you know, all of the non-technical things are where it’s failing and through the conversation that I had with my coach one of the things I discovered about myself is that I really didn’t miss writing software anymore. I really didn’t miss trying to make all of the computers stay running and that’s part of, I think where there may have been a little bit of self-sabotage in the back.

If this succeeds, I’m gonna be stuck writing code and monitoring computers for forever. But through that conversation I realized that what I missed most about being in the corporate world was precisely having those one-to-one conversations with my direct reports, seeing them grow and change and get promoted and I realized through that conversation, I just hired this guy to spend the next year having one-to-one conversations with me.This is a profession. This is how I want to spend the next chapter in my life. So I ended up closing down the software as a service business, helped all the clients migrate onto other free systems that were serving them better than I could and went to get my professional coach training and that was a little over three years ago.That’s been my full-time focus ever since then and I can’t imagine doing anything else.

[00:11:31] Ghazenfer Mansoor: 

Cool. Yeah. Hiring a coach was also one of my biggest lessons, my journey from doing a consulting to a startup to this business because the mistakes I was making, I just thought, I’m doing the right thing. Like, engineers have this natural tendency, they wanna build those strong scalable systems not find, not focusing on the customers. So you want to work with people who have done it before,who can help you, who can show you the path. Many times we even if, no matter how smart we are, it’s not easy to see your own path and you need that for accountability as well.

[00:12:15] Steve Dwire: 

One of the things I love about the name of your podcast, it’s Lessons from the Leap.You know, we’ve talked about multiple leaps that we’ve made and my first leap off into the software as a service business it was well misguided I would say, you know, because I didn’t have that input or I wasn’t willing to listen to the guidance that I saw all around me that, well, I’m special, I’m different. I can make this work even though all the rest of the people say that this isn’t the right way to do things and yes, I would say I learned some lessons from that leap also that good advice is good advice for a reason.

[00:12:55] Ghazenfer Mansoor: 

And we looking back, we realized those were the mistakes when we were making those mistakes. We didn’t realize that, as Steve Jobs says, you can only connect the dots. Looking back, you can’t connect the dots looking forward and that’s the same experience that I got and you got. Okay, So many leaders describe challenges like burnout, lack of recognition, imposter feelings and you have coached many of the people through these, which of these challenges do you think is the most common among today’s tech leaders?

[00:13:34] Steve Dwire: 

Well, I think things change and I think I would say, this is gonna sound like a cop out answer, but I think they are all common and they take their turns. I think everybody experiences each of them to some degree.I also think it’s really, it depends that old cop out answer. It depends on the specific environment. But you had mentioned burnout, imposter syndrome, What was the other one that you’d mentioned?

[00:14:04] Ghazenfer Mansoor: 

Lack of recognition.

[00:14:05] Steve Dwire:  

Yes. Lack of recognition. I rather than if I can, rather than selecting one of them as most common. I would say part of the biggest challenge with all of them is coming to terms with one’s own sense of identity. I think the challenge for all three of those is really rooted in a lack of clarity around who am I and what makes me valuable here? Burnout comes when nothing I do is ever going to be good enough.

Lack of recognition fuels into that, especially when you’re moving from manager to manager of managers. The obvious work is being done by the frontline individual contributors. That’s what gets metriced. That’s where all of the, I mean  especially in software engineering, you know. They’re the ones with the pull requests, they’re the ones with the code reviews. They’re the ones who are producing things and writing code and making products and promoting to production as managers and especially as managers of managers, we don’t have the metrics that say look I’m doing a good job.

And so we try to find anything that will make us feel like we’re doing a good job. So we work harder, we stay later, we have more conversations, we fight harder. And all of that leads to burnout. It leads to the feeling of the lack of recognition, and it leads to that feeling of imposter syndrome saying, I know I have a seat at the table but I feel like I don’t belong here and then we live that out by saying, because I don’t feel like I belong here, I’m going to act like I don’t belong here. I’m gonna keep my mouth shut. Just try not to make waves because I’m afraid that I won’t actually have a place at the table if I speak up. So that, so underlying all of that is just a sense of personal identity.

[00:16:25] Ghazenfer Mansoor: 

Good. Okay and how do you help people shift from I need to be the smartest in the room to, I need to build a team that thrives.

[00:16:38] Steve Dwire: 

It really starts with just a conversation with that person to understand what is really driving what’s underneath them. For some of them it is fear. Some of it is baggage from a previous situation where they were mocked for their ideas. It could be any of a number of things, but for many it’s just that fear of having their ideas shut down.

Fear of if I speak up, I’m gonna look like the oddball. I’m just going to go along with what everybody else is doing and really the big thing that I work with some people on when they have that is to help them to recognize the disservice that they’re doing for their employer, for their company, for their team.

When they keep their ideas bottled up, they’ve been brought to the table for a reason. They’ve been hired into this position, or promoted into this position for a reason and when they allow their fear, when they allow their imposter syndrome, their conditional work based on what kind of recognition they’re going to get, when they let that get in the way then they are personally choosing to withhold the very value that they’ve been called to bring and so I can help them. Well, we’ll just talk through what is an example, what is a value? When is the next opportunity you’re going to get? What are some of the things that you’re thinking through? What are the ideas that you have and haven’t shared?When’s your next opportunity, when will you commit to sharing that? Those kinds of conversations.

[00:18:25] Ghazenfer Mansoor: 

Okay. Is there any book that you can recommend or any, I mean, obviously coaching in person is one, but a lot of people would like to learn also from other sources. So, any recommendations?

[00:18:43] Steve Dwire: 

There’s a classic one that’s regularly recommended and I’ll recommend it as well. It’s the manager’s path. When we think about all of the different stages, I tend to divide things into four stages: Individual contributor, manager, manager of managers and then senior leadership. Just kind of four big broad but what’s the name? Camille? I’m looking for the book. Here it is. Yeah, Camille Fournier, I  don’t know if I’m butchering her name but that one you can see all the little tabs.

Just lots of great things in here, lots of great insights, and at a more granular level and lots of different individual advancements. Another one is called Leadership Passages by David L. Dotlich, James L. Noel, and Norman Walker. And this is not just software engineers or engineering but various senior leadership roles included and lots more tabs, lots more insights from that book.

But just a lot of great opportunities to look at just Personal leadership growth moments, including things like recognizing that you regret making an upward move and you want to take a step back. That is a leadership passage and it’s covered in that book. So those would be two.

[00:20:14] Ghazenfer Mansoor: 

Cool. There’s another good book not on this topic but as you use the word regret, so the power of regret. I forgot who is, I think Daniel Neil maybe, but yeah. So probably will add that in the notes that book or maybe Daniel Pink.

[00:20:32] Steve Dwire: 

Yeah. Daniel Pink. I’ll have to go look that one up.Thank you.

[00:20:35] Ghazenfer Mansoor: 

Yeah. Okay, can you share a transformation story, someone you worked with who made a breakthrough?

[00:20:44] Steve Dwire:

The scenario I was describing earlier is probably a common one and so one person in particular, they were in a director role and they were finding themselves at the table in the meetings, having some qualms about decisions that people were making but they had this identity of the other people are the experts. I’m just here to make sure that the work stays scheduled even though they had a history and a growth path through engineering. 

But, You know, we had the conversation and we’re talking about what is it that they personally value. So we went through a values exercise that I make available for them to recognize these are the things that are important to me.This is how I find my own motivation and then through those values, we’re able to determine a strategy next time this event happens. They had an offsite that was happening and he could feel already there was some angst about even having conversations. When you get in that room with all those people the intimidation is there, I’ll just wait for people to come talk to me and he was able to take that step, go out, you know, make those relationships and what was particularly interesting about this particular story was that rather than this person having come to me looking for coaching this was a one of those events where it was sponsored by the employer and so the one who was sponsoring actually we had a conversation partway through where I just ask what have you noticed? because we don’t, when I’m coaching, even if the company is paying for it.

We don’t talk to the company about what’s happening in the coaching sessions. Those remain confidential, private, so even though we had never talked about what we had been working on, when I talked to the sponsor and asked, what have you noticed?He was able to articulate, well, I’ve noticed that he’s speaking up more in meetings. I’ve noticed that he’s doing much better with building relationships. He outlined the very things that we had been working through and later when I had a conversation, you know, years after he had mentioned that when the sponsor when he’d left the company and brought somebody else back in it was somebody new to be a leader. That leader observed about the person I had coached. But this guy’s really good. We should be giving him more responsibilities. So he had been able to overcome those things that had gotten in the way of being effective at the director level.

[00:24:01] Ghazenfer Mansoor: 

Cool. So, how can founders or CTOs or leaders who are listening know when someone on their team might need the kind of support you offer? What are the signs?

[00:24:15] Steve Dwire: 

Well, one of those signs would be that holding back. They look like they have something to say, but they’re not saying it or just disengaged in the meetings often really just the fact that they are new, especially moving from individual contributor into a manager role.

Yes, there is a role for management training and some companies don’t even offer that but I have yet to experience an engineer, moved to management who will succeed easily without somebody to be able to talk to about this is what I’m experiencing. These are the challenges. I would say just about any engineer turned manager would benefit from a coach 

Some senior leaders and some directors are capable of giving that coaching, but most of them merely believe that they are but if they haven’t had, if they haven’t experienced that kind of professional level coaching from somebody , they won’t necessarily know what they’re missing. I would say that for somebody who’s really looking to see how well they do at coaching, Michael Bunge Steiner’s book, the Coaching Habit is a really good surface level description of what coaching looks like the professional coach training takes it to a whole new level and especially in an organization where they’re maybe a little bit of not quite psychological safety, where it’s not safe to speak up and voice the challenges that one’s facing. An external coach is immensely helpful because it gives them the perceived permission, the recognized permission to say what they’re actually struggling with.

[00:26:22] Ghazenfer Mansoor: 

Good and have you seen any differences where the organizations who have a flat hierarchy versus the traditional hierarchy?

[00:26:34] Steve Dwire: 

The biggest challenge that I see in a super flat hierarchy is the level of one-to-one engagement between the managers and the direct reports. I suspect and I don’t have data around this but I suspect that the startup environments that are most prone to flat hiring, you know, the flat organizations also happen to be the ones that attract the kinds of engineers that are more interested in just leave me alone. Let me do my work, I’ll get it done. I don’t really care about the one-to-ones, I don’t care about the relationships. 

But once they grow, that’s where the challenge comes and now you can’t grow the company beyond a certain point and maintain that kind of flatness and so it’s really the growth of the company once you need enough. People doing that engineering work, you’ve, there’s gonna come a point where people are gonna start feeling left out. The psychological safety is gonna start to degrade. You’re gonna see the consequences of weak relationships.That’s when you know it’s time to unflatten.

This is a phrase I like to use when people are unflattening their organization, they’re gonna introduce that level of frontline management and very often that’s when you need to invest in the coach to help those especially when you’re doing many at once help them to succeed because that’s the leap in organizational structure. Now that definitely can benefit from lessons that others have learned.

[00:28:28] Ghazenfer Mansoor: 

Thank you. So, I’m gonna change the topic. I know when I was talking to you last time, you’re talking about scheduling an appointment and you said one thing that you, so you talked about shifting from asking for time to offering it.

What mindset shift made that possible for you? And also can you elaborate that as an example for our audience?That’s good information to have.

[00:28:57] Steve Dwire: 

Yeah, I had forgotten about that conversation, so thank you for bringing that up and again. This is an example of how a coach can help because just like doctors have doctors and barbers have barbers, coaches have coaches. So this was part of a conversation with my coach, my approach to building conversation had been, I would reach out. I would notice people who introduced themselves in a community that I’m a part of. If they shared their LinkedIn profile, then I would reach out and say, I saw that you shared your LinkedIn profile in such and such community. We’re glad you’re here. Welcome and then only if they would say something that would indicate, I think I might need a coach.

Only then would I. Bother to take the time to ask them for 30 minutes of their time. I would love to have a virtual coffee with you. For example, when I talked to my coach, we were digging through what’s the reason for that and what I realized was I was seeing people as prospects and so the conversation was for my benefit.

So I was asking them for their time to serve me, and he pointed out, Steve, when you have conversations with people, you can help them no matter what situation they’re in. You can offer your time. They don’t have to be prospects. What would it look like if you could view as offering your time instead of requesting theirs? And from that I had so many interesting conversations since I’ve made that shift. And rather than saying, I would love to have 30 minutes of your time. I would just say, if you would ever like to have virtual coffee so we can get to know each other, strengthen our professional relationships, we can support, encourage each other. Just let me know. And so many times people will respond with what a generous offer. 

They use the word offer in their recognition of what happened in that context and so many conversations, people saying this was such a valuable conversation, you made me think and that’s exactly the kind of conversation that I had missed having left the corporate world. Now I get to do it all the time and switching from request to offer, just give me that many more opportunities.

[00:31:43] Ghazenfer Mansoor: 

Yeah, absolutely. No great insight. So it’s like saying, here’s my friend who’s looking for a work. If anybody has an opportunity versus, I know this amazing person who have some availability and he’s not gonna be available soon, so I’m happy to connect you with that and so only we have so many responses. 

People say, okay, I wanna talk to this guy because now you are offering data rod and they are looking. So that’s human nature. When somebody asks, it’s a pushback.

[00:32:18] Steve Dwire:

Absolutely and that’s the power of that just a tiny little insight, a tiny little shift of perspective and it’s the same kinds of little tiny shifts in perspective that each engineer turned manager, each manager turned, director has their own collection of little shifts that will make the difference in their success.

[00:32:42] Ghazenfer Mansoor: 

Cool. So we’ve been talking with Steve Dwire, thanks for sharing those insights.Where can listeners connect with you and learn more about your work?

[00:32:55] Steve Dwire: 

The two key places would be LinkedIn, just Steve Dwire, D-W-I-R-E on LinkedIn and I post a video every Tuesday and Thursday with some management tips addressing one of those four tiers of leadership that I mentioned earlier and you can also visit northway insights.com and if you go to the musings page, you’ll see those same videos if you would prefer to get them in your inbox.

[00:33:29] Ghazenfer Mansoor: 

Absolutely awesome. Finally, what’s the next leap? So you are more excited about

[00:33:37] Steve Dwire: 

This is a leap. I would say I’m probably mid-leap at the moment and while I am committed to continuing with the same process that I have for continuing with the coaching over the past week or so I have also committed more of my attention in my free time to a science fiction novel that my son and I are writing together. So I’ve been diving a lot deeper into the craft of fiction writing. So that’s maybe it’s a half leap because I’m still keeping a foot in the coaching.

[00:34:22] Ghazenfer Mansoor: 

It’s one of those multiple leaps that we talked earlier.

[00:34:26] Steve Dwire:

 Leap upon leap. Yes.

[00:34:28] Ghazenfer Mansoor: 

Yeah, absolutely. Steve. It was great to have you. Thanks for listening to Lessons from the leap. If you enjoyed today’s episode, don’t forget to subscribe and share it with someone who would find it valuable. Thanks again, Steve.

[00:34:43] Steve Dwire: 

Thank you.