562: Growing Your Career by Getting Comfortable With Uncomfortable Conversations

Jason Bollman 00:01

I had to think through the worst-case scenario and realize that worst case, I would be okay. I would leave the company. I would go figure out something else to do and it'd be fine.

Introduction 00:17

This is the Happen To Your Career podcast with Scott Anthony Barlow. We hope you stop doing work that doesn't fit you, figure out what does, and make it happen. We help you define the work that is unapologetically you, and then go get it. If you feel like you were meant for more, and you're ready to make a change, keep listening. Here's Scott. Here's Scott. Here's Scott.

Scott Anthony Barlow 00:42

Big decisions. You know how these work. Our brains usually fight us and they want us to stay in our comfort zones. Plus, if you're like me, you can turn nearly anything into logic. Yes, I know I'm not loving work and my boss is a little way overbearing, but there could be another opportunity four months from now. Many people find themselves torn when it comes to choice, like, staying in the same place versus making a career change. They know, you might even know, and feel deep down inside that something's not right. But we still struggle with taking a chance to actually make a change. Why on earth do we fight what we know to be true in our core? That's the question we're going to dig into today. We see how others reach their goals and we think we must follow in their footsteps to reach the same success. But the truth is, we don't have to follow them. If you want to take more control of your life, this episode is absolutely for you.

Jason Bollman 01:37

I basically came in and said, "Hey, I'm leaving. But I don't know when yet." And they've kept me around. I think that they know that whenever I come and I say, "Hey, I want to take on this thing." I'm not being selfish. I really see opportunity for improvement. So I think it gave me a little bit of a benefit of the doubt by really coming from that value early on.

Scott Anthony Barlow 01:56

There's something that gets so often missed. When we're wanting to make a change in our life, of any kind, we're usually focused on what comes next– immediately next, and how do I make that change now, right this second. Here's the reality, though, it's not just the now and the next that is the reason to make a change. Instead, it's actually what comes much later, and what making that initial change has paved the way for that is really the good stuff. And that's why we're bringing Jason back on the podcast, and in a more recent conversation, I had with him two years later, so you can see the impact in his life. And what making that initial change and having those initial awkward conversations with his boss to create a role that fit him, well, you can see what how that turned out, and all the things that opened up for him in the future. So let's go back to where Jason was two years ago.

Jason Bollman 02:58

So as I was making the transition, I was leading a group of consultants at a company. So I was in a management position, I was working on a software solution. So it was still very technical. And I don't know how far back you want to go. But in college, I studied engineering. So the technical piece was really kind of nice. I was working with clients, which also tied into a master's in education that I had. And I was leading a team of 11 people. So I got some management experience that I had always kind of strived for. So on paper, it was exactly the job that I would have crafted for myself. It had all the components that I thought were important to me. But I kind of looked up one day and realized that it doesn't feel right, that this isn't where I want to be, something isn't where it needs to be. And I kind of had gotten to a point where I had spent too much time kind of in my own head and talking with my closest friends and family, and my wife kind of gave me a kick in the pants that I needed to go and work with a business coach. And then working through a coach from Happen To Your Career, identified some things that I needed to change. So I was able to move into a new position within the same company, same department, but instead of leading the consulting team, I took over our offerings of how we were selling the services, and looking over education of the trainings that we do for our clients.

Scott Anthony Barlow 04:23

Why did that feel like a better fit to you at the time? What were some of the differences if we're looking back? This is almost two years ago at this point, right?

Jason Bollman 04:32

Yes, yeah, it is. Part of it was personnel as part of moving to this new role. I changed who I reported to, which was a big portion of it. But I also got to really look at, not just delivering on the things that have already been kind of put into a contract and just kind of making sure the machine was still running, I really got to take a step back and look at the bigger picture and help craft some of how are we putting the machine together so to speak. And looking at, you know, the way that we're pricing, "This offering isn't working, let's tweak it. This one's not working anymore, let's just stop selling it. Here's one that we keep hearing complaints of something that we need, let's go ahead and create a new offering." So it's getting a chance to get out of just running the organization and get a chance to kind of craft how it works.

Scott Anthony Barlow 05:21

Why was that such a big deal for you that whole idea of crafting how it works, if you will?

Jason Bollman 05:28

Sure. Well, yeah, as part of working through my time with my coach, she kind of helped me identify that I have a bit of an entrepreneurial bug in me. So getting a chance to kind of not just be the frontline manager and get a chance to look at kind of how the mechanics work behind the business was definitely appealing with the idea of eventually branching out and running my own organization. So that definitely was a big piece of it. And I think it also, part goes back to kind of the tie-in with my engineering education background, being able to kind of take things apart and put them back together. So it's really kind of twofold there for sure.

Scott Anthony Barlow 06:07

Okay, so that whole entrepreneurial bug, I know we talked a little bit about that briefly when we had you on the first time. But it sounds like you've been able to nurture that a little bit in what was a new role at the time for you. Now, let's get into what's happened since then. Have you been able to nurture that anyplace else?

Jason Bollman 06:27

Yeah, I feel like there's been a lot that's changed in the last few years. And even within the role that I'm in now, it has kind of morphed even further. Over the last few years, our company has acquired over 15 different businesses. So I've gotten involved in some of the merger acquisition pieces, not so much before the deal, right, of due diligence and any of that type of work. But after we bought the company, looking at how do they run their professional services, operations, kind of aligning it with what we do, making sure that they have what they need from a systems perspective. So that's been a really exciting piece that I've been able to work on with many of those 15 acquired companies. And then as a result, so my role has kind of transformed less so much looking at the offerings that we're selling and more looking at the operations of the departments and helping to: one, set the standard and, two, make sure that the new people coming in are working towards that standards. That was something that maybe two years ago, I didn't necessarily know that I wanted. But, as I've been going through, it's something that I definitely enjoy. And I'm glad that I've been able to get that opportunity and my role kind of transforming into this operations.

Scott Anthony Barlow 07:42

That is very cool. Where else have you been able to satisfy that entrepreneurial bug?

Jason Bollman 07:48

I did do some kind of testing that kind of played out, being a coach myself with some people that I knew. And it didn't quite fulfill me in the way that I was envisioning. But probably even more so as I did a lot of networking with other like-minded people that are in a job that have entrepreneurial aspirations and got into a mastermind group through a mutual friend. So I've been part of that probably for the last year and a half now. And what's really interesting is, as I was meeting more entrepreneurial-minded people, people that had started their own businesses that were kind of running things, I realized that entrepreneurs are a unique breed that they're very much at... I see everything as an opportunity. They're nonstop full of ideas and things that they want to start and just dive in and take action. And I realized in talking with them that I had some of that, but I'm a lot more analytical and like to think things through, I don't have a million ideas kind of coming to me all the time. And I realized that I'm more of the kind of the integrator working alongside a visionary to help take these, you know, 100 different ideas of what the business could be, and breaking it down into, okay, what are we specifically going to take action on. So not only was my role transforming at work, it was kind of simultaneously as I was self-identifying that I'm probably more of a better number two running kind of operations behind the scenes of a new business, as opposed to kind of just going out and doing it all on my own.

Scott Anthony Barlow 09:17

That's super cool. And you mentioned this concept of designing small experiments. But for you, it sounds like that was pretty interesting, but also critical in allowing you arrived to some of those conclusions that, "Hey, maybe I'm not meant to be necessarily the visionary type portion of it." And when you say entrepreneurial, there's some very specific things that you mean and are associated with that now, and it sounds like had you not done a little bit of that experimentation, you wouldn't have had that type of feedback to be able to come to those conclusions. Am I getting that right, first of all? And then I'm curious what else you learn from that?

Jason Bollman 09:59

Yeah. No, I think you're right on with that. And part, right, I had kind of in my head what being an entrepreneurial person meant. And I think as I've been going on this journey, I'm realizing it doesn't necessarily have to be the same for every person. But there are the people that have started numbers of businesses and they're in their lifetime, right, grow and sell or maybe it doesn't work out and they start a new thing, you know, they do have a certain type of characteristic. But that doesn't mean that that's the only type of people that can get into business ownership and can be an entrepreneur. So I'm continuing to learn and see how I fit into that room, even though I'm realizing that I'm more of the operations person, as opposed to kind of a traditional founder that you might, or at least that I thought of up to this point.

Scott Anthony Barlow 10:48

Yeah. So with that transition two years ago, where you shifted into a completely different role but still within the same organization, and it sounds like even similar section of the company, what do you feel like was the biggest thing that you learned during that transition?

Jason Bollman 11:04

The biggest thing I learned was just how much things just keep changing. You know, and part where we acquired a lot of companies. But it's, you know, as I went into that role, I really was excited to work on the offerings of how we sell our consulting services. But what I learned as I went through that is that really, it was more the training piece that our senior leadership was looking to really grow. The consulting arm was doing pretty well. And yeah, we could tweak offerings, and there's some new opportunities that are out there. But training had really been something that hadn't been being successful. And so I ended up having to put a lot more of my time towards that than the offering piece. And so, it just kind of goes to show that businesses grow and evolve and change, and the market kind of dictates how things turn out. And so as we were working on improving the trainings, we were finding that a lot of clients really wanted small, quick hits, free trainings that give them just the simple stuff, they weren't looking to buy full day training courses to cover everything A to Z. And so we continually had to keep kind of tweaking what we're putting together to meet what the clients were asking for.

Scott Anthony Barlow 12:16

That's interesting. How have you seen that set of learnings then impact both your work and as well as anything you have done outside of that role over the last two years?

Jason Bollman 12:29

It's a good question. I think it's still lessons that I'm learning. As I look branching out on my own and partnering as kind of an operations person that you can't come up with a product offering, kind of in a vacuum, you need to really get a good handle on what people are asking for. And probably even more importantly, is what they're willing to pay for it. Because even if they tell you that, "This is exactly what I want", and you put it together, it doesn't necessarily mean that they're gonna pay you for it.

Scott Anthony Barlow 12:53

This is... I feel like this is the lesson that anybody that's affiliated with any kind of business or marketing or sales or product development, all of those touch this exact area. I, myself, have had to learn this lesson multiple times. So I'm so glad to hear that you're getting to learn it and have been learning it on an ongoing basis over the last two years. What do you think... And totally different question for you. But you know, I was just thinking about your transition. And I think that what you did, and if you want to listen to his past episodes so that you have the context, definitely go back and listen to that because I think you did a really nice job. One, clarifying more about what you wanted. And I know that's part of the reason we got to sit front row is we're working with you on that. But then, you went and had what can be some more difficult conversations for some people in the world to be able to express how you wanted something different, or we're interested in taking on different types of projects, and then that evolved into a new opportunity. One, am I remembering that correctly? It's been a long time since we had that conversation. And then two, my question from that is, as you were doing that, what really helped you to navigate through that? Because it wasn't a one-and-done type process. It was an ongoing thing that kept evolving if I understood correctly.

Jason Bollman 14:25

Yeah. And it's interesting, you know, sitting here now, trying to think back because I feel like I've had numerous kind of similar type of conversations since then, maybe to a lesser degree, but because I had that first conversation, I think it's been easier to bring up "hey, here's where I see I can add a lot of value in kind of the acquisition front" and "hey, I'm certain to realize that I liked separation stuff. Can I, you know, take on more of those types of things?" But you know, I'm remembering back two years ago when I went in and said, "Hey, this role isn't for me. I'm looking to make a change." It was really scary. I was mentally preparing that they were going to, you know, show me to the door. And that was going to be the end of my career at the company. It was very intimidating. And so I think part of it was, I had to think through the worst case scenario and realize that worst case, I would be okay. I would leave the company, I would go figure out something else to do, and it would be fine. It might not be my ideal, but it would be okay. I think the other part of it as I was going in the conversation, is I was thinking about what was best for me, but I was also framing it in value add to the company, as well. You know, I came from a standpoint of I'm trying to be very transparent. I also picked that timing because we were looking at kind of year-end evaluations, and they were determining raises and bonuses. You know, I came in and said that I wanted to make it known that I wasn't leaving immediately. But I probably wasn't going to be here, at least, in this role long term. And if they wanted to reallocate some funds around that, they could do that. And I think coming from a place of value add and looking at the big picture, and what's best for the company, as well as yourself, made that a much easier conversation. And then on the back end, I was just 100% ready that if they showed me the door, that it would be painful, and it'd be hard, but I would be okay.

Scott Anthony Barlow 16:14

I'm thinking about that. And I've been in that exact situation, and it is hard. But I think that's something else that we all know to be true is that, you know, when we can come up with those worst-case scenarios, rarely does the worst-case scenario actually happen. I would say that from all of the conversations that I have ever been a part of, or been witness to, or been on the receiving end of, or being been on the opposite end of whatever experience, almost all of them turn out way better than what people imagine they will be as long as they're doing what you said, which is going into it, trying to look at how do we make this a win-win. How can this be, not just good for me, but also good for the company? And how can I approach it in that partnership-type mentality? So one, really nice job doing that. Because it's easy to sit here, you know, two years later on a podcast and say that. It's much more difficult to actually do that in the moment, right? But I'm curious about something that you said, you said, "Hey, since then, since I've had that initial conversation or set of conversations, it's been much easier to bring up the same type of topic." And it sounds like part of what you meant was continuing to structure or create your career path or evolve your position, or you tell me what you meant by that when you were saying it. But also, what's made it easier?

Jason Bollman 17:36

Yeah. I mean, I think it's, as I mentioned, business evolves, you know, I'm learning more about myself and kind of what I envision my career being that I keep seeing little tweaks and little room for improvements and projects that I'd like to get more involved in, or projects that I'm doing but really aren't in my strength zone. And it's all those types of conversations of trying to take on more work that's interesting. And the things that you're doing that aren't exciting that you know, might not be as important. Are there other people or other ways that we can get that done to free up more of your time? So those have been kind of the types of conversations I've been having. I think why it's been easier, I think first because I, myself, went through that first conversation. And it turned out way better than I had expected. So there's a little bit less fear every other time I go in. And I also think right to the organization, since I basically came in and said, "Hey, I'm leaving, but I don't know when yet." And they've kept me around. I think that they know that whenever I come and I say, "Hey, I want to take on this thing." I'm not being selfish. I really see opportunity for improvement. So I think it gave me a little bit of benefit of the doubt by, you know, really coming from that value early on.

Scott Anthony Barlow 18:51

That's so interesting, especially since anytime, not anytime, but a lot of the times when we talk about these types of difficult conversations that you might have with a boss or your boss's boss, or anybody who has influence and whether maybe you stay or go or has some kind of power or authority, there is that trepidation or is that fear there, and we do jump to those worst case scenarios. But what I'm hearing you say is that from your experience, having that initial conversation has led to a lot of, I would say, far-reaching impacts as well because now, not only is it easier for you, because you've done it, you've gotten the t-shirt, been there practiced and you feel more confident about it, it sounds like. But then two, something else that it sounds like maybe you didn't anticipate is they consider when you come and have a conversation. It sounds like your words carry more weight now as well because they know what is behind them. And I'm guessing probably a higher level of credibility too.

Jason Bollman 20:00

Yeah, definitely. It's funny as you're saying that I realized that it does happen. And I don't know that it's necessarily that I think that I'm smarter or better than anyone else, it's just, you know, I keep showing up and trying to figure out what's best for the business. And I think that's what then takes what I say with, you know, seems to have a little bit more clout.

Scott Anthony Barlow 20:20

I love that. So, I'll give you some context for why I love that so much. Actually, there's a lot of different reasons, way more than we have time for within this conversation. But Jason, I get emails, I would say, almost every day, from people that are in a situation where they feel like they have bosses or companies that are taking advantage of them in one way or another. And well, that is true, more than I would like to think about, that does happen from time to time. But when I start digging in with these people, or as my team has conversations with them, a lot of times we realize that there are behaviors there where they're allowing people to take advantage of them, basically, because they're saying, "Hey, it's okay to treat me this way." And you know, whether that is simply continually working past business hours, many, many, many, many, many, many days in a row, maybe they haven't actually told them differently, or anything else. But the reason that I love the conversations that you've had so much is because part of what you did, whether you meant to or not, is you began drawing boundaries there, and declaring what you actually wanted and needed in a way that was good for you and the organization. And that is something that really is difficult to do for all the reasons that we've talked about. But it paves the way to being able to continue to do so again, and again, and again and again. And this is the world's longest compliment ever. But really nice job. So...

Jason Bollman 21:54

Thank you.

Scott Anthony Barlow 21:54

Yeah, absolutely. And I'm curious since you've been there done that, what advice would you give to people that might find themselves in that situation where they want to take more control of their career path? Or they want to have some of these more difficult conversations with their boss or boss's boss or whoever might have a vested interest there?

Jason Bollman 22:15

Yeah, I would recommend starting small, right? My example is, I came in and said, "You know, this role entirely is not for me, and I'm going to make some sort of change, whether it's right a different role in the company, or whether I leave the company entirely." But if you can pick a specific area, right, where it's, you know, maybe you want to work from home one day a week because there's a lot of distractions in the office, and how can you frame if I work from home, in afternoon, here's the results of where I got more work done. I was interrupted less, you know, I didn't have as many people stopping by and I was able to get the really important things done, right? Start with something small like that, or whatever is your biggest pain point. And then just focus on on that little ask where it's not this big, massive thing that you're going to have to change in your role, it's just one thing where maybe one day a week or one day a month, you don't have to fight with traffic, you can get a little bit more done, and you kind of buy yourself a little bit of room where you don't feel like the company is taking advantage of you, and then go back and show that by doing that you were able to produce more, and it's really helping the company out as well.

Scott Anthony Barlow 23:24

I really liked that idea of starting small, then it's not so intimidating too, like, you were talking about, hey, I was super fearful about what was going to happen and imagining the worst case scenario as you went in and have that big conversation. But if that had happened over time, and had already built up that credibility and relationship by asking for smaller things, then maybe who knows, maybe it wouldn't have been so intimidating that way. So I love that advice. What do you feel like has been in your life, career or otherwise, over the last two years, the biggest place that you have learned to control or influence it in a way that you didn't before?

Jason Bollman 24:06

It's an interesting question. I think similarly to what I was saying before, it's obviously still learning, right? I hadn't been in a management role, right? So I had people that reported directly to me. And in some ways, that's almost kind of easier to influence because you can say, "Hey, this is what we need to do. Let's make this the priority over that other thing." And people that work for you will go ahead and do it. When you have your peers or even right, your boss or your boss's boss, that you need to get action taken care of for a project to be done, it's a lot harder to influence. And so I think it's really what I've learned so far, is framing out what you're trying to accomplish, how it's going to be a value add and trying to be as specific as you can of, "this is what I need and this is when I need it by", and then when they don't deliver, you know, because they're busy people, great following up and not in a negative way, but "how can I help? Is there anything I can do? Do you need additional information? Is there anyone else that can also help with this?" That has been somewhat helpful, although it is still challenging to get busy people to get things done. So I'm still learning and growing in that area for sure.

Scott Anthony Barlow 25:13

Amazing. Anything else that you want people to know?

Jason Bollman 25:18

Yeah, I don't know if so much to know. But I mentioned right, the entrepreneurial piece, one thing that hasn't kind of come up yet. So a mastermind that I was a part of, the guy that runs it was looking to kind of expand his business. And I've had the opportunity to partner with him and launch online membership platform. It's a pretty small group. But could we get together, it's other people that are identifying a business they might want to launch or just getting a business off the ground, or have recently gotten off the ground and kind of want to make sure that they keep it moving. And so I think maybe the lesson there is, right, there's probably a lot of people in your current network that you're already interacting with that can help you get to that next stage, that can partner with you, whether that's in your job, whether that's people you know outside of your business, whatever the case may be, I think there's more untapped potential in our lives than what we realize. And I think if you really get clear on what you want, and you tell people what you're looking to do, there will be things like the partnership that I was able to form out of the mastermind to go and start working on the side and building up a membership platform that we then hope to kind of keep growing and turn into a full business.

Scott Anthony Barlow 26:34

Most of the episodes you've heard on Happen To Your Career showcase stories of people that have taken the steps to identify and land careers that they are absolutely enamored with, that match their strengths, and are really what they want in their lives. If that's something that you're ready to begin taking steps towards, that's awesome. And we want to figure out how we can help. So here's what I would suggest. Take the next five seconds to open up your email app and email me directly. I'm gonna give you my personal email address, scott@happentoyourcareer.com. Just email me and put conversation in the subject line. And when you do that, I'll introduce you to someone on our team who can have a super informal conversation with and we'll figure out the very best type of help for you, whatever that looks like. And the very best way that we can support you to make it happen. So send me an email right now with conversation in the subject line.

Scott Anthony Barlow 27:26

Here's a sneak peek into what we have coming up in store for you next week.

Speaker 3 27:32

I think that was one of those moments that I was just realizing that being good at something, though, doesn't necessarily mean you're going to be happy at it. Or that is this fulfilling as something else might be.

Scott Anthony Barlow 27:46

I think all the time when people find our podcast, they think about, "Well, I must not enjoy my job", or, "This is for people who don't really like their work and want to do something that they actually do like." And actually what we find is that's not always the case. What about if you were changing careers, and you've had a job that actually was something that you really enjoy, and maybe you've even found that it's impactful, or it's what we might call "meaningful work" or "more fulfilling work", and you're even great at your job because you're using your strengths, and you have a team that you love working with? Okay, so if your current role checks these boxes, you might wonder why you still feel that tug to make a change. Is it possible to justify leaving what many people might consider a great career? The short answer is yes. The grass may actually be greener on the other side.

Scott Anthony Barlow 28:42

All that and plenty more next week right here on Happen To Your Career. Make sure that you don't miss it. And if you haven't already, click subscribe on your podcast player so that you can download this podcast in your sleep and you get it automatically. Even the bonus episodes every single week, sometimes multiple times a week. Until next week, adios. I'm out.