Kevin Stafford 0:02
Hello, everyone, and welcome to another episode of the conversations with coaches podcast. I have already been having an excellent conversation today with Stephen Webster, Stephen helps growth minded business leaders ignite next level growth through performance coaching business systems and technology. He is the CEO of Wellfleet enterprises, recent graduate of the zero to dangerous Peak Performance Training Program, which I’ll have to ask about at some point, mentor and advisor to individuals and organizations across business. Steven, I’m already grateful to speak with you today. I’m so glad you’re on the podcast. Thanks for being here.
Stephen Webster 0:37
Well, Kevin, thank you so much for having me. I’m very much looking forward to our conversation. And like you mentioned, we already kicked started it. So I’m looking forward to continuing with it. So thank you again.
Kevin Stafford 0:46
Yeah, I kept having to get them to break our conversation to remember to hit record. So I know this is gonna be a great one. Let me start with what I’ve cheekily called My superhero origin story question sometimes. How did you? And I’ll ask you kind of in two parts, how did you realize that you wanted to be or already were a coach? Or coaching? And how did you go from that realization that coaching I think, is who I am? Or what I want to do? And how to serve? And how did you turn that into the coaching business you have today?
Stephen Webster 1:14
Yeah, you know, Kevin, I started my career more in corporate America. So I started my career in learning, right, and learning from great leaders and great and great business people. And as as I continued to sort of climb the corporate ladder, I found that so much of what I was doing was teaching. And whether that was teaching peers and certain things where I had a discipline or a skill, or teaching other folks that are on the team to do things a little bit differently, or to think outside the box. So it was like a natural thing for me to just start to do that. And I found great joy in doing it even at the earliest stages of my career. So even though I didn’t start my coaching practice, until 12 years ago, I was sort of always doing it. And as I, you know, became president of companies and I ran divisions, and I had big staffs. I actually was doing it at a time where it was management by walking around, I know you, you can’t do that anymore. And it’s like, you know, how do you walk around a Zoom meeting, right? management by walking around enabled me to really connect with everyone that was working with me to help one get to know them a little bit better. But to dive into the things that were on their mind dive into those opportunities to debate those with them, right, in a thoughtful way to have conversations that got them thinking about things differently than the way via maybe the way they were originally thinking about it. So it just sort of continued to evolve. And so the great satisfaction that I was getting from those discussions and the feedback that I was receiving, you know, it was kind of like, you know, what would Webster say was what they would come up with, right? So I was receiving great feedback from all the people that I was working with, as well. And one thing led to another and it’s like, you know, what, there’s too many signals here, around being a coach or doing something that I really love. So maybe this is something that I, I indeed should
Kevin Stafford 3:07
pursue. So it really almost it kind of, it seems like it grew inside you in the same way that you were a leader where you were kind of like leading from alongside where it’s like, it’s kind of sort of growing and evolving in parallel to everything else you’re doing sort of I say, in parallel, it’s actually more like a braided rope, you know, we’re just kind of, it’s just a part of everything that you’re doing as a leader yourself, serving other people going alongside them and guiding them where they need to go. I love the fact that you talk the way that which you talk about engaging with people the management leadership by walking around coming alongside and sometimes debating sometimes going back and forth, sharpening each other, you know, that kind of guidance leadership, the Sherpa up the mountain, you know,
Stephen Webster 3:45
yeah, the sharpen the saw, I guess, is one of the terms that they use, right, which is to just keep probing and keep them keep picking at that. And then, you know, in like the, in the 90s, I became much more aware of like personal development, behavioral assessments, Myers Briggs, predictive index, things like that. So so I really leaned into truly understanding what really makes the person tick, right? How do you have much more thoughtful conversations with them? How do you become more self aware and that self awareness, my journey started, you know, probably in the 90s, around that I was introduced to it and I, I really leaned into it because you really, you find that it’s very easy to get along with people that are just like you, right? We gravitate to people that are like us, because it’s easy. There’s not a lot of friction there. But but the value is really in the diversity. The value is in creating teams that have a tremendous amount of behavioral diversity and even work experience diversity, so that you can come up with a better with a better solution than the ones that you would naturally come up with. So that has been a really continuous part of My practice, and I know we’ll talk about that a little bit. But I really try to get to know the person at their core, right. So if I get to know them at their core, I’m able to build a trusting relationship with them and dive into areas that maybe you wouldn’t be able to dive into. If indeed, your relationship was nothing more than experiential, right. So we generally, you know, I mean, so we generally Oh, what do you know, Kevin, I don’t know Kevin yet. But but I’ve had two or three great experiences with Kevin. So therefore, I want to have more great experience with Kevin Right. And, and if you’ve worked in corporate America worked in any sort of accompany, right, you might have my bad have Bob, or Lisa, or someone who you had one or two, and they weren’t, maybe they weren’t such great initial conversations. So our natural tendency, really, then is to shy away from that a bit, you know, it’s maybe not lean into it don’t know a little bit deeper. Well, why? Because it’s harder, right? So just as people, as people, we tend to want to take the easy route. But when you’re building a team, and you’re building a team, especially cross functional teams, or folks with a lot of different technology skills, like we have today, you know, you’ve really got to understand where where they’re coming from, whether that’s extraversion versus introversion, whether that’s independence versus collaboration, right? Whether that’s steady Eddie, or driving or whether that’s I need rules, or God, don’t ever give me any rules. I don’t want any rules, right? There’s all sorts of dimensions of your behavior that the more you can probe on that and dig in the more trusting relationship you can have Kevin and so you’d have the point where where the magnet connects to each other instead of repelling against each other, if you know what I mean. Yeah,
Kevin Stafford 6:41
perfect. I love that analogy is funny, I was thinking about magnets earlier while you’re speaking. And I got to thinking about a gemstones or crystals just as an analogy, where I often find myself thinking of people as these beautiful faceted gemstones that when the when they’re aligned, right, and when you’re in alignment with them, the way the light passes through you is just well, not to be too poetic about it, but it’s brilliant. But it takes it requires you understanding the way light passes through them the way those facets are fixed, where you can engage with someone in such a way that you bring the best out of each other and serve each other the best. And a good leader will understand what aspects of their team connect where they overlap, where their magnets attract, where their light expands, and set people up, put people in those positions to really give the best to each other and serve each other the best. And that’s it when when it happens. And when it’s great. It is one of the most beautiful things you can be a part of, because you really do feel like you’re part of such something bigger than yourself.
Stephen Webster 7:36
Oh, it’s so memorable, right? When it happens like that when when you’re on a great team, or you’re working with great people, you carry that with you for the rest of your life. And there are a lot of experiences that I’m sure that we have both had, right where we were on teams or you’re just shaking your head, you’re like, Oh, my God, this is just not working. And then you have other teams where where there’s a certain cadence to it, right? There’s a trusting factor, it just seems to click. And you know, if you think about those guys who go to battle and win a championship from, you know, in a sporting in a sporting event, or do something great and accompany those teams stay together and have those memories forever. And you remember all of those people fondly, you know, and then there’s so many teams that were like, Oh my God, you just want to pull them out of your head because for whatever reason, either either you didn’t have the right leadership or you didn’t have the right shared goal of what you were going after. Or it was unclear or for some reason, you didn’t have a trusting relationship with all of the folks there where you felt like you could say what you wanted to say, and still be respected by that, right? There’s a lot of people who show up on these teams who want to dominate the conversation, right. And my natural tendency as an independent person is to dominate the conversation that you know, I don’t need an agenda. Kevin, I just show up with my agenda. I couldn’t rip it. But but, you know, in that particular regard, am I really engaging everybody else that’s on that team? And the answer is no. So you’re, you’re tying it back to your braid and the leadership, honing those leadership skills and recognizing those behavioral differences. And diversity is, I think, really where I leaned into that, and jumpstarted it right, which says, I’ve got to figure out a way to make these people win. We’re making the company win, and we’re going to make them wins, right? Because because it’s a shared responsibility. Because if the company wins, you want to make sure that your employees and your team win as well. But getting everybody aligned, making sure those goals are clear, making sure you had the right communication, making sure you had the right accountability, right, being able to pull people out who might not have been on the path, but do it in a thoughtful way, right? Because not everybody keeps the pace, right? Some people move a little slower. Some people move a little faster. But it’s recognizing those differences and being able to do that to really capitalize on the human element, which is which is at the end of the day, what it’s all about.
Kevin Stafford 9:58
Exactly. That’s That’s it That’s a nice place to pivot into getting specific, we’re already talking a lot about basically what you do and how you approach your coaching. But let’s, uh, let’s get down into the, into the end of the ground floor here. I’m gonna talk about brass tacks. I’ve always love that phrase. Let’s get down to brass tacks. So how I like to ask this these days is it’s kind of a simple two part question, Who do you coach? And how do you coach them? Almost like I got you in the interrogation rooms? Like, what did you know? And when did you know it? So obviously being like, who you focus your coaching on if it’s largely C suite executives and their teams or like that kind of who and then the, the how being like one to one, which obviously every coach does at some level, but you also have group coaching or keynote speeches or courses that you host and run. So yeah, who do you coach? And how do you cook them?
Stephen Webster 10:46
My clients are, are primarily CEOs and executive leaders of businesses, really, the range of businesses that I serve, I would say would be in the small to mid size business. So two to $40 million range. You know, those folks that have a good growth mindset and are looking to improve, not just their business, but all aspects of their life, right? Because at the end of the day, if your work is if your work is healthy, if your personal relationships are healthy, if your finances healthy, and if you are physically healthy, guess what, you are just going to be a better leader, you’re going to be a better person, right? So I try to really probe in and have longer term relationships with folks where I get to know them really well and help them on their journey. From my services perspective, I do one on one performance coaching. Of course, as you mentioned, I am in the process right now starting up a couple of new mastermind groups with a company called growth 10. So I’m in the process of of selecting members for that right now. I have been running a CEO group, multiple CEO groups through the Enterprise Center at Salem State University for local businesses up in Massachusetts, I’ve been doing that for about six or seven years now. I also provide coaching facilitation and teaching services to leverage growth operating systems for businesses. So if you think about many CEOs, right have to create it on their own. Well, if you if you if you’ve ever read traction, or the Entrepreneurial Operating System or scaling up, right, there are a variety of different systems there that you can plug into an organization to help them grow. So I’ve partnered with Cruz and company to basically utilize their roadmap growth, basically, their growth operating system to help businesses implement something that is accountable, very focused on defining the goals. And just it just helps them routinize that and create habits around it so that they’re not figuring out well, what am I doing my operations? What do I do over here? How should I run my finances? Right? A lot of there’s a lot of decisions to make. So why not use something that’s a proven process, especially for businesses of that size. So So I also teach that as well. So
Kevin Stafford 12:56
I don’t want to turn into an advertisement for for EOS. But a couple of are a couple of my clients use ELS and they’ve, it really does everything that you say. And then some it really does take away that burden of feeling like or actually having to reinvent the wheel yourself. In every aspect of your business, there’s so much weight that it distributes and carries forward really does free you up to do the thing that you want to do with your business to be focused on growth and, and growing yourself and your business and your team. It’s yeah, I don’t want to turn to a commercial for that. But I am a big, big fan of ELS.
Stephen Webster 13:27
So you’re not worried about what your meeting cadence is or what your OKRs are. I mean, you’ve you’ve gone through that process, and you’ve figured it out. Right. So. So that’s exactly right, that’s so I do that, because to me, it’s not just providing them with insights into how they can be better leaders. But if I can also provide them with the tools that they need to run a better business, the goal is to get them out of doing stuff that is just in the business all the time, and get them to do stuff that’s on the business, right? And that and if you’re always like running from meeting to meeting, or you just on the hamster wheel or, you know you’re not prioritizing your calendar, you know, you’re not doing all of those things that are absolutely critical for your success. You’re just exhausted at the end of the week. Okay. I mean, is it really great to have yet another 80 or 90 hour week? No, no, it’s not. It’s not great at all. It actually, it epically sucks, really, but but when you’re doing it, you think you have to keep doing it because everybody else seems to be doing it. Well, how do you get out of that mindset? How do you realize that there’s a different way to do it. And you can be successful doing it in a much different way. So
Kevin Stafford 14:35
and that, to me, that really is the heart of why coaching is not just powerful, but I think it necessary, because what you do is you need that interrupt, to change your mindset to see things differently, that you just it’s hard to do that on your own or it’s hard to have that happen for you without something catastrophic or life changing to occur and what a coach, I feel like the role they specialize in coaches come in, and they allow you to see things from a different perspective. To have to understand what you’re doing, why you’re doing it, your intentions behind it. And then to also on top of that have systems and tools to help you to change. And then establish a new mindset, a new system that’s sustainable in a way that will keep you healthy and happy and have your business healthy and happiest. I feel like coaches are really uniquely positioned to best serve in that way. And it really it is, it’s business changing, it’s team changing, it’s life changing.
Stephen Webster 15:27
Yeah, and many as you know, many of the CEOs, right as you go through your phases of growth, your business when you’re a one to $3 million business is much different than when it’s a three to $10 million, business and much. So there are these little chasms that you need to cross over, right? So in the interim, beginning of your journey, right, everybody on the team is a generalist, because you’re trying to get everything kind of done as best you possibly can. Eventually, you need to bring in functional leaders, though, who are really, really good at that. The CEO, right? What the CEO was good at something the CEO was good at the vision, they were good at product development, they were great at sales, they were great at marketing, whatever those, but it doesn’t make the CEO great at everything. So So and you’ve got a lot of CEOs, right to figure out well, how do I do this, right? You know, and now you’ve got what you need to be really great at digital transformation, you need to be really great at digital media, you need to be really great at a whole bunch of things that that you may not be great at, or you may not be able to scale up right in your organization’s So so how do you reconcile that? How do you how do you get how do you get comfortable with partnering with people with companies that that for the person doesn’t work with you? Right? I mean, you’re, you’re borrowing them right there. But but you’ve got to get comfortable doing that. And in today’s world, whether it be cybersecurity or digital transformation, or or social media or figuring out what to do on tick tock, I mean, you know, all of these businesses, they’re not going to have all of those skills on staff to do that. But many of those entrepreneurs or leaders are not yet comfortable with with contracting out to third parties for those services. So there’s an awful lot of change that goes in right, the CEO is a lonely position. You don’t really have that many people to talk to. So having a coach to talk to and someone you can just bounce an idea off of or pick up the phone and scream at every once in a while. Because you can’t really ask your employees all those questions. And generally speaking, you can’t ask your family most of those questions. So so that’s why either a mastermind group, which I think is really awesome for groupthink, and getting different different, different perspectives, right, from different industries and things like that to help solve your problems. Or having that one on one coach that you trust and you value who can just help you think through things right. My goal isn’t to give them the answer. My goal is to give them the landscape so that they can make the right answer.
Kevin Stafford 17:56
I know it always comes back to that better questions, or questions? Yeah, I want to I want to do jealously keep you all day like this, this conversation. This is this is my meat and potatoes is stuff that gets me out of the bed in the morning. I love this. But we’ve already like I promised, I’ve been watching the clock. And we’re already going a little bit past where I usually like to go. So before I let you go. I’ll thank you now. And I’ll thank you again later. Thank you for this conversation has been fantastic. Where can people find out more about you? And Tupac question Where can people best connect with you? Like if they want to send you messages or get on a meeting or have a strategy call like so where can people just learn more about who you are and what you do? And then how can they connect with you?
Stephen Webster 18:33
The easiest thing is just go to my LinkedIn profile. It’s a sweat man as web ma n up there at LinkedIn. And right in the header file. It basically says book a meeting. So so it’s just a clickable link, you can go and book the meeting. For folks who are more traditional and just want to reach out via email. It’s just Steven at Wellfleet enterprises.com.
Kevin Stafford 18:51
I love that email qualifies as traditional.
Stephen Webster 18:55
Right? Some people love email.
Kevin Stafford 18:58
I also accept handwritten letters, but I think email is more my more my more my traditional speed.
Stephen Webster 19:03
My address is.
Kevin Stafford 19:07
Steven, thank you. Thank you. Thank you so much for chatting with me today. This has been great. I feel I already feel the urge to have you back on for a party just so we can keep exploring some of these ideas. But I’ll let sowed errs before, you know before I do that, but it has been fantastic. And just thanks for talking and thanks for doing what you do.
Stephen Webster 19:24
My pleasure, Kevin, thank you so much for having me on the show and happy to come back whenever you think it’s right. Awesome.
Kevin Stafford 19:30
We will talk to you again very soon.
