Unlocking Your Leadership Potential w/ Jason Weeman

We discuss the importance of aligning your startup's value proposition with your personal goals, "getting out of your own way" as a founder, and more.

Leadership Coaches seem to be a dime a dozen in this workforce landscape. There are plenty of “coaches” out there who market themselves as experts but do not have the clout to back them up. That’s not the case with our guest today, Jason Weeman, the Founder of Refine Talent Development.

Jason is a Certified Professional Coach whose senior-level experience at LinkedIn, Upwork & Apple has influenced his unique take on coaching. He helps founders break free from self-imposed barriers and empower their teams to drive the business forward.

As a founder himself, Jason knows the challenges that come with taking intelligent risks in the entrepreneurial world. He emphasizes the importance of aligning your startup’s value proposition with your personal goals and highlights how founders often hinder their own success by not allowing their teams to shine.

Our conversation dives into:

  • How founders can motivate and support their teams
  • Navigating the  relationship with your Co-Founder
  • The benefits of investing in employee growth & development
  • Creating alignment around your startup’s mission & company values

This discussion with Jason Weeman of Refine Talent Development comes from our show Startup Success. Browse all Burkland podcasts and subscribe to the show on Apple podcasts.

Episode Transcript

Welcome to Startup Success, the podcast for startup founders and investors. Here you’ll find stories of success from others in the trenches as they work to scale some of the fastest growing startups in the world stories that will help you in your own journey. Startup Success starts now.

Kate 00:18
Welcome to Startup Success. Today, we have Jason Weeman in studio, who is the Owner and Founder of Refine Talent Development. Jason works with a lot of startups and founders as a leadership coach. So I know this will be a great conversation. Welcome, Jason!

Jason 00:37
Thank you so much. I appreciate you having me.

Kate 00:39
Great. So I’m excited to hear how you got in this role, kind of like your trajectory, because people just don’t end up in a in a place like this. So if you could walk us through it, that would be great.

Jason 00:51
Yeah, I mean, it’s an interesting story, I always talk about how I kind of grew up in retail. And that was something that I think catapulted me into an opportunity to be able to develop teams and coach and lead in ways that maybe at the time when I was younger, wasn’t necessarily natural for me, but became a passion of mine led me to working for some great companies, including Apple and LinkedIn. And throughout that experience, it kind of created these additional chances for me to start applying skills that I was learning over time and developing into ways that I think identified for me that coaching and providing a level of guidance in ways that wasn’t necessarily typical for people was helpful was something that actually created change and help people kind of connect to what they were really capable of doing. So ultimately, I worked for other companies past those two that I mentioned. And it led me to wanting to build my own business, which I did a few years ago. And then I’ve had an opportunity, especially over this last year to go a little bit deeper into it. So it’s been a lot of fun.

Kate 01:51
That’s great. I appreciate that. And I can say to everybody listening, Burkland’s leadership team has used Jason. And the first day, we were all expecting the typical leadership training. And it was not at all what we were expecting, and so great and unique and I don’t want to give away any surprises, but it was awesome. So you do really know your stuff. For the founders listening your startup, we have a lot of early stage founders, like what should they be kind of keeping an eye on, thinking as they’re getting going?

Jason 02:28
Yeah, they’re I mean, they’re obviously those that are listening probably have just as many examples as I do in terms of some of the challenges that you faced when you’re thinking of taking an intelligent risk ina lot of ways, I think we like to look at it in that way, where there’s a lot of thought that goes into the work that you’re going to do and what you’re passionate about. But for founders, I think one of the the bigger things for them to consider up front or, you know, really those different elements related to the people that are going to help support whatever vision you have is how you’re going to bring value to market in different ways. And whether that’s through the product itself, or the service, sometimes we can get so consumed by what that is that we might kind of distract ourselves a little bit from what actually is meaningful, and the value that we’re trying to position ourselves around as it relates to ultimately what those goals are. So that’s, that tends to be in a lot of the conversations that I have with founders and those that are starting, or even considering that this is the path that they want to go down, that sometimes that thought process around how all of those things kind of connect. And you know, for them personally the role that they really want to play as they continue to grow and build their business. Because I think what we’ll probably get into in terms of the conversation, as founders, we can kind of get in our own way of what success can look like. And that’s a challenge. It’s something that’s hard for a lot of people to accept and acknowledge. And the earlier that you can create that level of self awareness, the sooner that you can actually have a little bit more clarity around how you need to approach a lot of the things that you’re going to deal with.

Kate 03:59
I think it’s great. You brought that up early on, because when we interview VCs on the show, they all go back to the same thing that it really comes down to so much around the founder, right? Like you can have this great idea, this great market opportunity. But so many founders can tank it, because they get in their own way. And just the VCs go over and over again about the founder and the founding team. So do you help founders with kind of that organizational design and getting started and that, I like how you call it that self awareness? I’ve worked with a lot of founders that didn’t have any self awareness. So…

Jason 04:42
Yeah, yeah. And there are a lot of us like in general, you know, within larger businesses that kind of struggle in that same way. And I think that’s that level of experience I pull into the way that I work with people, whether that’s on the individual basis or as teams and you mentioned working with your team. I think either are nuances to the industry and the type of business that you know, each person is in that kind of drives some of the decision making around that. But getting in our way, it’s, it’s difficult to not as a founder, because this is your thing like this is, this was your idea, your concept, your baby, you know, as people mentioned it, and you want to see, you know, the end result become, you know, the best possible one that’s out there. And the only thing that we can think of is, if it doesn’t turn out that way, you know, it all falls on me. And as you’re growing a business, and you’re starting to create a team that’s helping support it, there is an element of you’re doing that for a particular reason. And it is to be able to separate yourself and be the most effective, or play the most effective role as a part of that growth. And when we don’t allow for that to happen as a product of that strategy, then that is the end result, you know, we’re just kind of in the mix of everything and not allowing the people that we brought in that are talented and have the skills that we were looking for actually recognize what you know, again, what their potential is, and what they bring to the table. And you see that early on in startups in terms of working with founders, and in some of those leadership teams, as they kind of initially start to form and storm and find their kind of ground. But then you also see it continuing to get in the way as companies grow, and they scale and they’re thinking about going public, and they’re not letting go of the reins enough to allow for those that again, are more skilled in certain areas of that growth to actually perform at the level that they they could for you. And so where I tend to come into play from a coaching standpoint, and then also just from a leadership development perspective is how do you start to create more of that ownership, you know, across your team? And how do you support that as a founder and as a leader emulating it on a consistent basis. So that way, your teams feel empowered, they feel like they have an opportunity to make decisions and to take risks and to use data in ways that are actually going to drive the business forward. And I found that the more opportunities that you have to do that, and you create for your team, as a founder, it starts to build a lot more confidence around yourself in leading this organization, instead of on the opposite side of things. What will wind up happening is the leadership team starts questioning the part that you’re playing as a founder, because you’re so involved, and you’re not allowing for, you know, these things to happen. So I’d say that’s, that’s probably a common theme in a lot of the conversations that I have.

Kate 07:36
I really like how you walked us through that, because I hear that a lot on the show too. These founders talk about, you know, the ones that are successful, and I’m interviewing, they talk about the teams they put around them, and then giving the people the room to actually work and speak up and make recommendations and listening to them. And then I had a founder on the show who said he didn’t do that. And it came back to bite him. He said, I built this incredible team. And then as we scaled, everyone felt like I was micromanaging them. But I had been so vested in the early days, I had to get out of the way and figure out how to empower my team. And that’s a big hurdle we went through, and I really appreciate him being open and honest and sharing that. And so the fact that you walked us through that, and that it’s it doesn’t go away, then even when they’re you know, companies are preparing for an IPO, it could still be happening if you don’t address that.

Jason 08:36
Yeah, that is I mean, that’s a real thing that you’re talking about. And it’s not easy, you know, to just kind of disconnect from that and to not want to be involved in different ways. So it is you know, a lot of the the one on one coaching and creating that self awareness, going back to that language, the earlier that you can do that with a founder or in essence, co-founders, because a lot of teams are kind of formed in that way, where a couple people come together and have this idea and one person owns product, another is kind of driving the operational side of it. And maybe sales, depending on what it is that’s been offered is that if you can make that investment in yourself, because a lot of founders might not necessarily have that skill set to be able to self reflect and be a little bit introspective around how they’re showing up as these teams are being built, or if they even have kind of leadership experience. So that work upfront really starts to solve a lot of those kind of early growth challenges I find because there starts to become this different level of openness to things as you evolve. As you bring in new team members, you’re kind of considering the impact that it’s not just having on the company and what you’re trying to build, but you’re also understanding how it plays a part in the shift in your responsibilities, how you’re showing up, you know, and ultimately performing for the organization.

Kate 09:53
I really like how you phrase that around shift in your responsibilities. And then you mentioned co-founders, so I’m guessing that dynamics there can get really tricky. I mean, I’ve heard some people refer to it as like a spouse like a marriage. What have you seen there and any guidance you can give the listeners around the co founder relationship?

Jason 10:17
Yeah, I think you hit it on the head in terms of it is I mean, you’re you’re marrying into a business that you both, you know, have a responsibility to support, you know, if we, if we think about it from the relationship side of things. And so communication becomes a significant part of that, especially as a team starts to grow. And you have one founder with messaging that might come across and be delivered in one particular way. And then another that has maybe a slightly different point of view, or perspective because of what they own. And they’re not necessarily aligning their messages in ways that a team feels like you’re moving in a direction in this kind of continuous manner, where I have a lot of belief in what’s happening. Instead, it feels very disjointed, the silos become quite a bit more natural for people. And that’s where you start to falter a little bit, or you might not perform at the level that you’re capable of, because of all of these things that you’re just then having to go back and fix because of misunderstandings or duplication of work investment in a particular part of the product on this side. And then on the other, we’re not necessarily maybe supporting it operationally the way that we needed to, because we didn’t really understand what was happening. So again, all of these different elements wind up factoring into that strain in the relationship, which strains the confidence for anybody that you’re bringing on the team, they see it, they hear it, especially in these smaller startups, it’s hard to avoid, because maybe everybody’s on the same call together all the time. And they pay attention to it. And when that confidence starts to diminish, as I’m sure you’ve heard from other founders, that’s when things start to break. And it makes it really challenging to deliver against the goals that you’ve set for yourself, and VCs are expecting of you. And that outside pressure starts to create a whole different dynamic that becomes really challenging to recover from if the work isn’t being done to help support it.

Kate 12:10
That’s so true. When you were describing that I was thinking of a startup where I worked for the co-founders were not in alignment. And it just trickled down through the whole team. And there were so many awkward calls. Yes, you summarize that all perfectly. So talk to us about culture, because that’s a buzzword, everybody talks about it culture, culture, but I have to say, on this show, the founders who really embrace like thinking about culture and values, it does pay off. I mean, it seems like it’s not just words on a wall, like it can really make a difference.

Jason 12:50
It does, it’s significant. And, you know, I’ve had a chance to work for companies that are probably have some of the more well respected cultures, you know, from a corporate standpoint, and large companies that have been able to sustain it, you know, as they’ve grown, that’s always one of the harder challenges is we have a couple people, maybe it’s three or four kind of starting this business, we’re all locked in, maybe they are words on a wall, because that’s the way that they collaborated to kind of design what the vision and mission was, and these different values that are in support of ultimately what you’re trying to deliver. But very quickly, can they become words on the wall, when there isn’t a level of consistency on how they tie in to everything that you’re doing every decision that’s being made every decision that’s not being made, in some cases to because it’s easy to just think that we have to go go go. And sometimes there is an element of pulling back a little bit because it actually does connect to this culture, that we’re trying to create a culture that is thoughtful in the approach that they’re taking to the value that we’re creating for a customer. And the decisions that go into that sometimes might not necessarily be as favorable to a certain group, or people that were hired and excited to do this thing. And they might have to hold back a little bit. And so the more that we tie in a lot of the decision making within the company, you know, to the overall vision mission, in some cases, companies will have both, and then also these values, then you can start to get really clear on if this is what we want our culture to represent. And these are our values, what are the specific behaviors that we expect to observe on a consistent basis that are in support of that. And when we see them, we recognize them, we celebrate it, we share it in different ways that are going to be valuable for the individual and how they’re recognized. We’re going to share it with the organization more broadly, because we want people to have a view into what that actually looks like. And then equally as important as we want to share when it’s not happening. And that typically comes down to creating a culture of feedback where people feel comfortable, and they have a common language and being able to share the challenges and the things that they’re dealing with and an open way without judgment and also they have a level of leadership capability that’s built within the company especially Usually with the co-founders or founders where there’s coaching involved, and there’s a level of curiosity where I can show up and start to authentically understand in a genuine way, what some of the things are that you’re dealing with the way that you’re going about making certain decisions and celebrating it, but also being able to give feedback in the moment around the things that might not necessarily be working as well. And so all of those pieces, what I found, really tie into the culture, because it’s a constant, you know, it’s talked about often, whether it’s an early days and all hands meetings that are happening to team meetings that are taking place. And there’s elements of recognition that are that are happening on a consistent basis, the more that the language is there and the examples are being provided, the easier it is for people to truly not just buy into it, but believe that this is something that everybody cares about, instead of once a quarter, when you’re doing a QBR, or a board meeting took place, and then you put them up on a slide and you give a review of what was talked about, that then becomes you know, something that’s on the wall, or in that case on a slide.

Kate 16:00
That doesn’t do it. But what you described using culture, you’re this healthy work environment, that’s what you are describing, I mean, through the use of a strong culture. And I would think one of the things that I think gets forgotten in startup worlds are the managers. You know, as you’re hiring, and you’re bringing in these managers, and they’re building teams, there’s not a lot of help and coaching for managers, I’ve just my own personal experience, is that something you see as well,

Jason 16:32
yeah, it’s rampant. It’s across every every organization, small, large, you know, there’s always the opportunity for it, there are very few that actually have kind of early on, set the stage for successful growth in that way. And, you know, the challenge is if, as leaders in a larger organization, we feel like we’ve tapped into our potential and growth as a manager of others, then we start missing the mark, because we believe that there’s no room to evolve and be able to support our teams any differently than we have, since we’ve started doing it. Or even if we’re just confident as a new leader, you know, we have nothing to learn, it makes it really challenging for people to actually believe that you’re there to support them. Because if you’re not curious about yourself, and how you can show up for your teams, it’s gonna be really hard for people to actually see that emulated in the way that you’re behaving and interacting with them. So that level of support is challenging in smaller organizations, because you might not have you know, a team and resources to do that. You haven’t maybe focused on that as like a part of the budget or what’s important up front, because there’s so much of there’s so much of a focus around the product itself and getting engineers in and, and people for product and you want to market and you want to sell it. And that’s great. But then you’re going to need supported as a lot of these, you know, bumps in the road and challenges wind up coming to fruition. And they will and if the team or you as a founder or your senior leadership team isn’t prepared to handle it, then again, it gets back into the confidence piece. And so if the culture is representative of development, and growth and opportunity in your career, and for you to learn and do these really amazing things, you need somebody there to support it, you are hired because you’re talented. But just because we’re talented doesn’t mean that we don’t need continued development, coaching, guidance and feedback. It’s an important aspect of how we continue to grow. And so if you invest in that, as a founder, and you develop that capability, and it’s consistent, as you grow your team, as you hire, you’re going to start to see that evolution transcend into the rest of you know, your managers as the company continues to grow, because it’s a part of the foundation, it is a part of the culture. And it’s another one of those examples of the things that you’re going to observe happening across the company, or the thing that you’re not going to observe, and people pay attention to it. And as you’ve probably heard, and throughout your career, a lot of people you know, will stay at a company, not just because of the company, but more specifically because of the leader that they have. And that’s really important to make sure it is a priority early on. If you haven’t thought about it.

Kate 19:00
That’s so true. While you were talking, I was thinking about that. That’s how you know, get retention, and you stop turnover by making that investment. Otherwise your managers feel like they’re on an island. And they don’t have that connection to the bigger picture and the team and they usually leave. Right?

Jason 19:20
Yeah, they leave. And I think what I found and even in larger companies, we have super talented CEOs and operators at the top and the C-suite that have been leading teams for so long. And sometimes there is a level of burnout and empathy that also has to happen on that side to realize like they’ve been doing this for a while and they hired you to do this work. And that’s totally okay. where the challenge comes in is as a founder or somebody leading a larger organization, when we talk about the culture focused around growth and opportunity in your career or to develop new skills. Usually you’re looking for executive sponsors. So if you’re an early stage company, and you’re starting to think about that So when you start speaking about that, in broader terms and selling talent to come to your organization, because this is what you embrace, this is what as a team, you have decided to embody and to show up in that way, and you don’t have the capability to actually do that. So you, you know, the talking the talk and not being able to walk it not that you don’t want to, you just haven’t developed the skill set yet. And then all of a sudden, the talent that you brought in that was promised certain things isn’t getting that level of connection with you. They’re not feeling challenged, they’re not feeling supported through again, probably a consistency and coaching, thinking about the strategic approach that you’re taking to your work, being curious about some of the challenges and how they actually can help you then turnover starts to happen, because they realize this isn’t what was promised I was sold something that isn’t even there. And the earlier that you can make sure that it’s there. It’s like selling a product without having the product finished. It’s like it’s gonna be great. But then it never comes, you know, the product never launches. So, I think a lot of us have encountered that on the consumer basis on the receiving end. And then internally, within companies, we can reflect back on plenty of stories where we were told certain things felt like this is why we made a decision, and then it was completely opposite. And all it takes is one or two critical hires that could either help you build momentum, or it could ruin everything that you’ve been building.

Kate 21:20
Absolutely. I know, I was thinking of situations I’ve been in, in my career when you were describing it. And I’m sure everyone listening is too. We’ve all been there. Absolutely. This has been super helpful. I could ask you a million questions. So we always wrap up the show, with just some last piece of advice, words of wisdom for all the founders listening, because it’s a tough journey, anything you could share would be great.

Jason 21:48
Well, I mean, first and foremost, for anybody that’s listening. And I just, I continue to respect that like the level of bravery that comes from, you know, taking this step and taking these ideas and concepts and things that are just so important to you, and bringing it into a place where other people can benefit from it. And what happens is you’re thinking so much of what this is going to impact outside of who you are, and what you’re about that bringing yourself back to that place actually can slow you down and help you move quite a bit faster in the end. And a lot of that, because of the work that I do tends to tie into development. And it starts with you, you can want to invest in your team. But if you’re not in a place to be able to support the investment that’s happening, so you’re developing capability across the rest of your team, and then you’re kind of still stuck in the same place and not challenging yourself, it’s going to be really difficult to be able to connect and support as they grow. And so it’s the priority. And I suggest that you know, any founder that’s thinking about a lot of this and their talent strategy and their organizational design, what’s going to be effective to make sure that this is something that they’re really considering up front as a priority.

Kate 22:53
So well said thank you. So those listening, how do they find more information about refine talent development and you? Where did where did they go?

Jason 23:03
Well, you can find me on LinkedIn, you can check out my profile on my background, I like to think that I’ve had a really interesting journey. So you can explore that a little bit. And some things that I share messaging past this where you can, I think get a connection to who I am and what I’m about. And you know how I actually show up for the customers that I work with. And then you can also check out on my website, different ways that we could work together at refinedtalent.net. So we take the development out to shorten that that URL for you a little bit. And you can always, you know, reach out on on LinkedIn and message them through different social media channels. So I appreciate the time. This has been a lot of fun. And I look forward to continuing to work with the Burkland team and anybody else that might find some value.

Kate 23:41
Thank you, Jason. It’s been great having you here today. Thank you.

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