John SmallMtn (00:00)

Welcome to another episode of The Founder’s Growth Show. My name is John Hill, AKA Small Mountain. I’m the founder of Adapted Growth. And today on the show, we have James Wightman. James is a business and life coach to business owners and has been doing it for longer than I have been in small business working on myself. Whenever I heard about his story and how long he’s been out here in the space, I was excited to talk with him. We had a very cool conversation that I think is going to help a lot of founders who are trying to find their way, maybe just getting started.

James, I’m going to pause for just a second. Can you talk a little bit more about who you typically work with in the space, and then we’ll kind of jump into the conversation?

James Wightman (00:39)

Yeah, absolutely. Thank you so much for having me here. What I would say, just as someone who works with business owners—I originally started all this in 2013, professionally coaching—in terms of what I do and who I help, it usually veers on two ends of the spectrum. Oftentimes, it’s people that are professionals wanting to start their own business to coach and share their services.

A lot of times I’ll help them, and then on the other end of the spectrum, I have just always been a person, for whatever reason, leaders have wanted me by their side. I kind of serve as a confidant, right? They have operations managers, they have people sharing tactics and strategies and helping them in all different areas, and I really love to be the confidant that serves them—that is by their side, helping them reset during the week on where they want to direct their focus, their attention, and what are the uncomfortable conversations they need to have.

Those are really the two loves that I’ve had: helping people transition into sharing their services, and then for business owners, really serving as a confidant to them. I call it a coach, really helping them have a reset during the week of what’s most important and what their priorities are.

John SmallMtn (02:04)

I love how you’re talking about that because one of the things that I have come to realize—I was just doing this because it was helpful to me on my path—was just giving people space to get it off their chest and to vent, right? People are not always expecting that from me whenever they’re working with me, but it’s like, “Okay, cool. How’s everything else going?” “Well, John, why are we talking about this?” Well, everything has an impact on everything else, right?

If you’re under the weight of rejection—because there’s a lot of rejection in sales—or if you’re feeling like you’re not being heard or listened to, all of that can really shut down the opportunity to work on yourself and get to the place that you need to be. It’s not just, “Here’s a framework and here’s a talk track.” I think a lot of people have a very weird, misguided view about what coaching can actually be, because sometimes just giving someone space with a qualified person…

I tell everybody: you can’t go ask for sales advice from people that have never carried a bag or carried a goal or a number, because they don’t know how to give you advice that’s actually going to help you. Having that space and giving that to other people is what leads to performance at higher tiers. But a lot of people aren’t thinking about that when they’re reaching out to coaches and consultants; they’re just looking for the help.

They’re not looking for the changes that they need to make sometimes, which is the hard part of this whole thing. Are you willing to change? Because we all need to change depending upon what we’re dealing with and what we’re trying to get to.

James Wightman (03:46)

Mm.

John SmallMtn (03:46)

Do you get that same kind of pushback if you’re working with a new client and it’s early stage? You show up and maybe you’re talking about some things that aren’t directly related to the operations of the business, the day-to-day of the business, or the revenue of the business. Do you have people confused when you show up as just a confidant or a conduit?

James Wightman (04:09)

Hmm. Yeah, I love this question. In the past, I would probably get a lot more pushback. I don’t as much anymore, and I think this has happened for two reasons. Just to touch on what you were saying about how people can be surprised: one of my original coaches in sales trained with Eli Wilde and others—in case anyone doesn’t know, Eli Wilde is Tony Robbins’ top salesperson. I had this coach, and I worked with him for a year. At the end of our coaching, he called me up and said, “James, I want to hire you for a year to coach me.”

I was like, “Wow, this is interesting. This person has made more money than me,” and all these different things. What he was really desiring help with was a lot of the other areas outside the strategy. That’s how I really entered this work. I remember at the end of that year, we did a recap call of what the experience was like, and he said something that always stood out to me. What he said was, “What most people think of as coaching is educational programs disguised as coaching.”

I think that’s what a lot of times people are used to—where they’re learning a framework or learning a strategy. Those things are wonderful, but there just isn’t a lot of space, which you’re talking about and which is wonderful that you’re providing someone, right? You’re actually giving them the space to share what’s really happening, because you know that even if somebody has a strategy, if all these other things are happening—or they’re stressed or dealing with a rejection or whatever it might be—then it’s going to be very challenging for them to move forward or to even use that strategy. So I love that you do that. I love that you’re sharing that.

One of the things that helped me in my enrollment process of shifting people’s perception is thinking of it almost like a house; there’s different entry points. Chances are somebody’s coming in because maybe they do want help with that practical or tangible thing, or they want help reaching that number, in your case, of sales. One of the things that I shifted in my own process is I would talk to somebody about that or help them with that, and then I’d transition it to: “If we’re going to work together, we need to look at all of you.”

To me, it really just became a natural part of the process that maybe at first they were like, “Huh?” But when I shared, just as you shared, that that impacts every other area of what they’re trying to achieve or their personal life, I think people become very open. It’s just not the thing that a lot of people know how to lead with. But as a coach, as a facilitator, it’s our role to open that up.

It’s kind of like if somebody’s on a sales call and they say, “I need to look at the money,” or they’re mentioning the price. There’s a lot of things that could mean, but it’s almost as though that’s the culturally acceptable way of saying, “I have another question.” It’s our role as the leader to know that there’s something else there for somebody. Yeah, I’ll pause there.

John SmallMtn (07:34)

There for a while, I was so focused on just the sales side—better process, better conversations, better outcomes—and very resistant to talking about all the other stuff, right? The philosophies, like: What do you do outside of work? How do you manage your relationships outside of work?

I did it kind of as an experiment with a client and saw that it was hugely helpful to them. Fast forward, I was working with a guy, and I started to ask about, “Okay, what does your self-care look like? What do your routines look like around work?” It was funny because he was working with me, but he was also working with a Tony Robbins coach. He goes, “John, I don’t know why we’re talking about this.”

I’m like, “Well, I get it, but I’m a big believer in how you do anything impacts everything else. While sales is a chaotic job, let me look at how you handle the chaos of life in these other capacities.”

He was so resistant because he was like, “I don’t know.”

I’m like, “Can we just try?”

Now it’s gotten to the point to where that stuff is so helpful if they’re there for the right reasons and there’s room for them to actually change. Now I kind of brute force my way into it, and it’s helpful for anyone who’s open to the idea. But some people aren’t quite there yet. How have you gotten better at getting people to show you the whole picture and be open to the whole idea?

James Wightman (09:20)

Hmm. Yeah, I think there’s a couple ways. There’s almost an intuitive temperature with somebody, where some people are very focused on the more practical or tactical items. What I’ve found is that usually I’ll try to open the conversation to other things, and I’ll read how they’re showing up and responding to that. I might even ask, “How are you receiving what we’re talking about?” Sometimes that in and of itself just really changes things. The fact that I’m introducing it—they didn’t even know that was possible.

Sometimes there are other people who really just want to stay on those strategic items. I’ll go along with that for a little bit, and then usually they wonder why something keeps reoccurring or whatever it might be. Then I’ll say, “We tried to talk about this before, and here’s why I think this is occurring. Could we open this back up again?” I’ve found that because they actually want the results so bad, they will then say, “Okay, we’ll give it a try.”

Sometimes their sharing is not as open or vulnerable, but at least the space is there. Then there’s a development of that relationship and that trust.

John SmallMtn (10:50)

Absolutely. There was a project, and the CEO pulls me off to the side—we’re doing morning syncs, doing the deeper work and everything—and he’s like, “John, I got a concern.”

I was like, “Okay, let me talk about it.”

He goes, “So my guys are telling me you’re talking about self-care with them.”

I was like, “Well, yeah. I’m talking about getting into your body, managing your relationships, eating well, and being healthy.”

He was like, “Well, I’ve got some concerns.”

I was like, “Okay, what’s your concern?”

He was like, “Well, that they’re going to want more breaks and time away.”

I’m just like, “Well, really the goal is to acknowledge that these things are mandatory, important things for ourselves and for our performance. That way, we bring full focus to work to get our work done, so that there is actually time and space for these things, right?”

He was an old-school guy, and he was like, “John, I just don’t know.”

I’m like, “Well, okay, that’s fair. Do you want to go look at the numbers and see if it’s helping or hurting?”

He was like, “Well, we don’t have to go do that. I already know that we’re ahead of pace and everything.”

I was like, “Okay, cool. So if this is working and that concern is not a real concern, do you have any other concerns?”

It’s interesting, because most people, I would say, have never really had a great coach, a great mentor, or that confidant to talk to and get it all off their chest, right? A lot of people might take it to their boss, and then it ends up not broadcasting well or not being heard well. Or they might go to HR, and then they get a black mark because they’re not a team player.

How do you get people to that space to where they’re open to what coaching can bring? Because there’s a little bit of stigma around coaching and development, like “I don’t need any help” and “Help is weakness.” How have you gotten better about talking to people and getting them to accept that maybe some help would be beneficial?

James Wightman (12:54)

Yeah, you know, I always find this interesting. I think there’s different philosophies on this. If you’re working inside an organization, it can be a little different. I tend to work directly with the business owners. Some people have a philosophy of: “Well, if somebody’s not open to this, my goal is not to try to convince them.” I might simply meet that person where they’re at. Whereas some people have an approach—and I think it’s more of a personality type thing—where they’re like, “I’m really going to reach this person, and I’m going to say the thing that needs to be said.” I think both are totally valid.

I would consider myself more of a gentle candor type of guy, because especially with the business owners that I work with, they’re usually stressed. They usually have to put on a tough face during the day and make the hard decisions. My approach of gentle candor is more of a place where they get to just relax and be. I’m not calling them out on their bullshit, but I’m being very loving while also calling them out on their bullshit if it’s needed—just in a really kind way.

For me, I probably am not the best person to be like, “I’m going to reach that person who’s resistant.” I’m more of a “when the person’s on board, I’ll meet them where they’re at.” Which I think is valid. There’s a type that’s resistant, like “I don’t want anything to do with this,” versus the person who’s perhaps a little hesitant, but they’re open to it. That, to me, is very valid.

I think if someone’s very resistant to growth and those other things, there can sometimes be something else there. You can have people on a team, and it’s like: why is this person on your team if they aren’t willing to grow, aren’t willing to change, and aren’t open to other possibilities of what they can create? There might be some uncomfortable conversations to be had about what it means to grow. What’s the balance there? Because sometimes it’s an important relationship, and how do you weigh that with the business? Does that make sense?

John SmallMtn (15:07)

100%. It 100% does. One of the hardest parts for me was being a sales guy, pushing through dissonance, and trying to do the things that had worked for me in the past, then realizing that good coaching is a pretty soft deliverable. You can’t just put it in their hands and then they’re immediately and forever changed. One of the lines that I have to remind myself all the time about is: I can’t have the cape on for someone who doesn’t want to be saved.

Being okay with “no”—because this is a soft deliverable, and it’s not like a phone or a test drive on a car where expectations are immediately met—it’s: are you open at all, or do I have to prove it? Because if I have to prove every step that trying matters and trying is worth your time, we’re not going to get anything done. One of the hard parts was being really okay with the fact that I’m not going to try to talk everybody into it, and really just looking for those people that are, as you said, open to it—even if they’re not exactly sure what it looks like—or already aware, open to it, and knowing that they need to change and need some help.

That was a very tough switch in my early days, especially coming from sales and having a goal, knowing that pushing forward and following up is sometimes more beneficial in hard products and hard deliverables than it is in soft. I’ve never been a super hard salesperson—”softer” is what all my sales friends would call me, but “clearer” is how I think about it on my own path. If you don’t think you need help, you’re right in the sense that I’m not going to be able to help you. So let’s just put it down and go find someone else to talk to.

James Wightman (17:24)

Yeah, I think this is so key, and it also applies in the coaching world, too. One of the things that I’ll share with clients or fellow coaches, depending on who they’re working with, is: I can’t want something more than somebody wants it themselves, because nothing is going to come of it. I can’t brute force someone along.

I love that you’re touching on this because there is such an importance in clarity. In a sense, you’re becoming so clear that it’s inviting somebody to make a distinction for themselves on whether they do or don’t want something in their life. Especially earlier on in sales, or even for coaches, when you hear those “no”s and you’re still developing your skill and the way that you want to do things, it’s so easy to go, “Well, is it me? Did I do something wrong? Is this rejection?” So yeah, this is so good.

John SmallMtn (18:33)

“It’s not a no forever; it’s a no for today” is a thing that every sales professional who’s spending time in the role understands. But there is that moment when you’re going out as a coach or consultant and you’re putting yourself out there—if you’ve not gotten to the place where you have built a methodology, a framework, or a way of thinking, it is kind of just you. If you’re not familiar with sales mindset, detaching from the outcome, and allowing people to have their own preferences, desires, and priorities, it’s going to feel like character assassination.

That’s one of the things that we have to talk about with people: you’re not selling yourself, you’re selling your ability to help them. We spend a lot of time talking with people about how if it is a soft deliverable, make it a concrete thing. Don’t just say, “Well, I’m just going to help you.” The thing that I teach people is called Sherpa, and that makes it a little bit easier to talk about. You’re not just going to be working with me; I’m not just going to be waxing poetic in our meetings. There is curriculum and a guided approach to this whole thing.

It’s too easy to take it as character assassination when they’re saying no to you. If you come from a place of subject matter expertise and that’s aligned with your personality, that’s some heavy weight to carry around. It becomes easy to want to avoid that rejection, procrastinate on doing outreach, and put yourself in hot water. It’s a very common thing that we run into, and I’m glad that you talked about it. A lot of people don’t understand that even salespeople I’ve worked with—who have sold something else and are now selling themselves—struggle a little bit with reconnecting not to the product or service that they sold, but to the solution that they provide. It’s a different way of running through the conversation and looking for your people.

Changing gears, because I want to talk about your path a little bit. Whenever we first connected around this, you said a thing that I’ve just been sitting with and thinking about: you quit the same job five times—the same job with the same company—until you actually decided to stay away, launch this thing, and get it to where you were going.

Can you talk a little bit about that time? A lot of people try to side hustle, or they jump ship and burn their boats. I’ve never really talked to anyone that was able to dip their toe in and go back and forth the way that you did. I’m curious: do you think it was helpful? Do you think it slowed you down? Or do you think that it was just the right thing for you?

James Wightman (21:36)

Yeah, I think it was the right thing for me, especially because I had seen so many different ways people leave their jobs. When I was even looking at leaving in the first place, I was living in New York City, and I reached out to someone. They were like, “Well, you need a year’s worth of savings,” and all these different things. Based on the amount that I was making, I was like, “Well, I’m never going to have a year’s worth of savings where I’m at.” Even having a couple of months of savings felt unattainable in that moment.

I must have really had people that loved me in my life and had the right support to be able to do this, or however things aligned. I was in my early 20s, so my family always had the philosophy like: get these things out of your system now, because especially when you have kids or other things at a later point, it’s not that you can’t do them, it just becomes more difficult to take more risks. But I think there’s a spirit in that ability to try something new and to take risks. I view that journey as informative lessons so I can tell others things not to do, or different ways to look at it.

John SmallMtn (23:08)

That’s the whole point of this show—to help people avoid some of these missteps that we all just have a habit of falling into. Sorry for cutting you off, please continue.

James Wightman (23:19)

No, you’re good. So at that time, my thinking was that I wanted to have this business. I wanted to leave the job. I did not want to be doing what I was doing, even though I was coaching—I was working in education—and most people would look at that and be like, “This is great, he’s set.”

We can feel inside when we want something different, or we want to step into something new, or we want to create, and it’s important to meet that need. The way that really all of this transpired: I remember I’d never heard of Tony Robbins, and I had a coworker that would bring his name up. Somehow I found out that there was some money that became available for me to use for development, and I was like, “You know what? I’m just going to go to Tony Robbins.”

I’m one of those people that I do not really look up anything beforehand. I just want to have the experience as it is. I went, and it was one of the most life-changing experiences that I ever had. He’s a performer and there’s thousands of people, but the principles in development are really key to life. Before then I was feeling this, and I’d gone to see a therapist, and I was like, “Okay, this is neat, we’re talking about these things.” But whatever I experienced during that week was powerful to help me tune into: what is it that I really want? I think that’s really the key, is just tuning into what is it that we really want.

Something blew open there for me where I had flashbacks to when I was little. I remember I loved magic and all different things, and I had fun. I felt like I lost those things in my life, and Tony Robbins used a thing called NLP. So I came back and I signed up for an NLP course. I don’t know if I was just following this idea of flowing with the universe or these other things, but I just started making new choices, new decisions.

I took an NLP course, and then I was like, “They’re doing a Level 2 to become a master practitioner. How can I do this?” I was able to—however I coordinated my decisions—I was able to get the money for the Level 2, and I did that. Something just really opened up in me, and I was like, “You know what? I want to travel.”

What I did was I wrote a proposal. This was at a time where people having remote jobs was not as common of a thing. I wrote a proposal to have my role be remote, because I was like, “I’d like more flexibility. I’d like to be able to travel.” I wrote it up. The thing was like two pages. It was very clear how this could work, and it was organized. I remember I shared it with my boss, my mentor at the time, and he was like, “You know, this is good. This is something that we can’t do now, but we’ll consider in the future.” I was like, “Okay.”

I did that originally after I came back from Tony Robbins, and then I took the NLP. Then something occurred for me during this. I remember I called him up and I was like, “Hey, I just want to let you know I decided that I’m going to be leaving and not going to be working here anymore.”

He said, “Where are you going?”

Well, I didn’t have a clue, but the first thing that came to me—where I always wanted to be—was Portland, Oregon. I said, “Portland, Oregon.”

He said, “Do you have a job out there?”

“Nope, I don’t have a job out there.”

There was something courageous about quitting. Energetically, there was a shift of me going, “I’m not choosing this anymore. Something else is more important to me.”

He was like, “Okay, just want to make sure you’re okay. That’s great.”

I think a week later we’re together, and he goes, “Here’s what we’re going to do. We’re going to do a test run. We’re going to make your job remote.”

I said, “Okay, this is interesting.”

I was able to do that for probably a year, so I was able to travel. I was able to work more on my business and different things like that. It didn’t progress at the rate that I had desired, but I developed a ton during that time. I came back to New York City after a year. I popped back here and there, but I came back.

At the same time, I had met my now-wife, Ellie. During that, I was like, “I’m working on this business, and I still want to work on it, but it doesn’t make sense for me to keep traveling.” I had another conversation with my mentor, and I had to decide: do I want to stay, or do I want to go somewhere else? I was in the attempts of quitting again—so I guess this is time number two—and we worked out what the role would look like and those types of things. I was able to stay and have a more solid relationship, because I just met my wife and we started dating and all those things.

There were just periods of time where I had to make a decision: do I want to take the next step, or what might it be? We always ended up finding a way to rework something. Then finally—I had clients and a lot of different things, and I was balancing it—maybe a couple more years later, I think it was around when COVID hit, I was like, “I’m not dealing with this stuff anymore. I’m just going all in on the business.” I reached a point where I felt I could do that, and so that’s what I did.

There’s probably more details that I could share in there, but I feel like that’s a good overview of some defining moments that changed the trajectory of me having the sense of where I could go and what was possible.

Also, life brings in a lot of different things. This person’s no longer here with us, but I remember during that time, I wanted to live in Portland and I put a message up on a board. I was like, “Hey, I got 500 bucks a month for rent. Is there a place I could stay?” Everyone said, “No, you’re not going to find anything for that here.” Then somebody said yes, and I ended up staying with them. We became good friends, and they had an issue where they were wanting to delete themselves from the world. I ended up getting them the right help and the right support. We stayed friends for years. They had other stuff come up later and we weren’t as connected, so they aren’t here anymore. But to me, that wouldn’t have happened if all those other things didn’t connect, and that was a life-changing moment.

Let me pause there.

John SmallMtn (31:19)

Yeah, I want to dig into some of that. The season of becoming really coachable and understanding just how much work there is to do on ourselves is always a unique time. Going back to that first Tony Robbins event, I’ve never been to a Tony Robbins event, and I’ve heard everything from “it’s amazing” to “it’s a grift” and everything in between. Were you looking for that, or was it just that this person was talking about it, so you decided to do it on a whim?

James Wightman (31:58)

Yeah, I think I’ve typically been a person that is open to different ideas and growth. It’s pretty common with sales and people in business—there’s a certain sense of growth and progress that we like. Something resonated, and I at least looked at the site and all those different things to have a sense of what I was walking into, but not really knowing exactly what the experience would be like.

When I got there, I could totally see how people could see it as a grift. However, from the openness, I really received it as these foundational principles of making a change in our own life, the way that we think, and the way that we operate—having a sense of how we operate so we can move forward. I was pretty receptive and open.

John SmallMtn (32:59)

When you talk about coming back to work after that event and then deciding to keep pushing yourself and developing yourself, there’s this moment in time that I talk about with people: when you become aware of the choices that you really have in front of you, as opposed to just waiting for the most opportune choice to show up like the only real option that you have.

This makes me very unpopular with some of my friends and some of my family, because I do think that everything is a choice. If you’re waiting around for permission versus just being willing to go out and work on what you want to work on, it can make you kind of a weird person whenever you’re in conversations or around your friends.

That’s how it feels for me. For a long time, I wasn’t really looking at all the options I had; I was just looking for the easiest option. Is that kind of how it felt for you when you were going through this stuff and figuring out who you wanted to be when you grew up?

James Wightman (34:07)

Sure, yeah. There’s a couple different things that come through for me here. One of the things that I became aware of—and I’m sure this has to do with upbringing and other things—was I had a strong leaning towards making sure that there was always an exit in some capacity, right? Because there’s this balance of: I’m committed to something and there’s no exit, or I’m going to see it through and just have a sense that I’ve made a decision and I’m committed. Then this other side of: there can be choices in front of us, and am I choosing the safe choice? Do I want to make sure that I have a potential exit for something so I can keep myself safe?

I think there’s different times for different approaches. One of the things that I became aware of—and I became aware of this in my relationship with my wife early on, a year in—there were challenges that were happening, and I had to share. I said, “You know, I’d really like for us to see a relationship therapist, because if we don’t, we aren’t going to be together. I know that.”

She was scared. It’s funny, it’s like we’re scared to go because we think the person’s going to be like, “Yeah, you two don’t work,” and we’re going because we want to work. Thankfully, we worked through those things.

One of the things that I realized is people are not an Amazon Prime package. They don’t just appear and we go, “Oh, there’s a little scratch here,” or, “There’s something a little off here, could I return it for a different version or a replacement?” People are who they are. I realized there’s an idea of being with what is, being with the person, and loving them. At the same time, I think this applies to so many decisions. If we can be with what we really want, sometimes it’s just the lens that we’re thinking from—how much we want it—that makes us think we need to make a rash decision.

When we can be open to, “What are really the choices? What can we commit to? What is the risk that we’re willing to balance?” I think that can really help with making decisions, rather than going, “You know what, I might take the safe decision,” or “I’m going to wait for somebody else’s permission to go do the thing.”

Whereas if we can realize we might be being called forward to something, it’s this balance of: can we know that we’re being called forward, versus when is there this moment where we might just be having a felt sense of fear—which is what I discovered in the relationship around commitment, particularly in this case to another human being? Because human beings are not fixed. I can put together an IKEA shelf, absolutely—that’s not changing on me. Working with people is very dynamic and changing, and it can bring up a lot.

That’s what’s coming through in terms of looking at decisions: are we being called forth to something, or do we kind of just have a fear coming up because we don’t know how someone’s going to respond?

John SmallMtn (37:43)

Yeah, absolutely. I think we could probably keep going down this path of, “Okay, where is that fear coming from?” One of the things that I think is super important to this whole conversation is: if they don’t have clarity of direction in the form of goals, it’s going to be really hard to help them, because they’re going to be able to avoid the uncomfortable and avoid the things that they want to procrastinate on.

The fact that you’re allowed to have big goals is kind of a weird concept to certain people. You’re allowed to push; you’re allowed to want to go be more. That’s kind of the first choice—the first sell is to yourself, that you’re allowed to go push for more, and it doesn’t make you crazy, it doesn’t make you unhireable, and it doesn’t make you any of these things. If you feel called to it, then it’s okay. Don’t backpedal and be like, “Well, I’m crazy,” labeling it badly, because that just shuts you down from ever being able to take the jump.

I also love that you weren’t selling yourself on the idea that it had to be this way and it had to work. I see a lot of people who get caught up in the identity of being a founder or entrepreneur, and then it’s not working, but they’ve got sunk cost and their identity wrapped up in this label. Then it feels like a failure to go back to a lane of consistency just in the form of a job. There’s not anything wrong with that.

Acknowledging that we’re going to develop in what I call “seasons” is very helpful for me, because I’m a pretty rigid person just by default. The fact that I’m going to be in different seasons means different things, and trying not to be so rigid around “I am now this” and “I am now that” can do as much help as it does harm in my experience.

Do you have another transcript segment you would like me to clean up?

James Wightman (00:40:03)

Yeah, absolutely. There can be a holding on to things. Sometimes I don’t like to use the phrase “letting go,” but in this case, I probably wouldn’t use it because we can have a way that we know how to do things or that has worked before that is so easy to hold on to.

I’m going through that now with some different things related to the business, where I know there are things that work that I’ve done before. Energetically, something in me is just going, “I’m not really feeling it.” In the past, I would have been like, “I need to scratch that and go to something completely new.” Now, it’s more of, “What if I could just let that be and be open to a new way, a new approach?”

I think maybe it comes from Buddhism, right? If you have a glass that’s full and you’re pouring into it, everything else is just going to go to the side. Could I allow myself to empty, to be open again? Not that I have to get rid of everything, but just that I’m not holding on to it as the one thing that I need.

Similarly, as you’re talking about having goals: we can have a goal, but are we holding onto it because we’re making it mean something if we haven’t yet achieved it? Or are we making it mean something if we have to go back to a job or have something part-time? Which very much happened for me during that time of quitting the same job five times. I took on something part-time so I could diversify my income. That actually helped me feel much more secure because it didn’t feel like my identity was in this one job. I was more in tune with what I wanted and making the choices that I wanted, which I think is really important.

If we tune in, are we making choices in our profession or business where we’re going with a decision that isn’t what we really want because we’re afraid that we’re going to lose something, or we’re holding on to something? We have these sunk costs like you’re talking about, and oftentimes we’re kicking the can down the road for those types of things. So, yeah.

John SmallMtn (00:42:43)

Epic. Great. I’m hoping that people are going to have some space and some room when they’re listening to this, because I think we’re talking about some very deep topics that would be very easy to gloss over if you’re not doing some deeper work on yourself. But I’m hoping that anyone who’s listening to this has some space to really dive into this.

James Wightman (00:43:05)

Could I share something on that?

John SmallMtn (00:43:07)

Please, yeah. Please do.

James Wightman (00:43:09)

There was a client that I worked with who had taken part in business programs. We worked together and he said, “You know what I realized, James? With a lot of the different programs and the things that I’ve done, I set goals. I learned things about business, but the last person I focused on was myself.”

That was part of our work: what are the things that he wanted in his life? What are the ways that he wanted to approach it? He realized—he kept saying this—”James, I don’t really have a vision.” We talked, and what came through was he said, “I have goals, but I don’t have a vision.”

What we started to do was craft a vision of what that really looks like, and then how the goals tie into that. One of the things that he put was, “I want to be a light in my community.” That started to show up in so many different ways. It changed how he had conversations with his team, how he had conversations with somebody at the store, and how he had conversations in his family, because that was really important to him. It wasn’t an identity in the business; it was really what he wanted.

He had five businesses and ended up closing three of them because he realized they weren’t in alignment anymore. From that work, he ended up having his most profitable year in a decade.

If somebody could hear this and truly listen to the gold in this: when you tune into what you want and the vision, then see how the goals match and align with that. Is it the truth of what you want and the truth of what you want to create? Because when you can come from that space, everything else will follow.

John SmallMtn (00:45:02)

Wow, yeah. Man, I’ve had a lot of goals that got me really fired up, and they were just for the sake of goals. One of the things that I have to talk about with every leadership person and salesperson is that there’s greatness in having a quota, because it’s a very clear line in the sand that a lot of other people inside of an organization never have clarity on.

My one job not in sales was so uncomfortable because it was always like, “We’ll just keep doing more, keep doing more, keep doing more,” and I could never really have clarity of, “Okay, what does good work look like inside of here?” Whereas in sales, if they’re doing it right, there’s a goal and a quota. But if you’re just doing it for them and you’re not doing it for yourself, it’s going to be a little gappy. It’s going to be hard to do the harder things.

The other thing that I try to talk about with people is that you can put yourself under really bad goal weight. I worked with a guy who dealt with this. He had crazy, massive, big goals. But when he put himself under that weight, he didn’t really have a plan or a path for how he was going to get to those goals.

He goes, “Well, man, I’m five years in and I’m not on my goals.”

I was like, “Okay, what are your goals?”

It was like moving to another country, buying in, and doing it the right way. It was going to be very expensive. I was like, “Cool. What was your reverse-engineered plan and path to those goals?”

“Well, John, I don’t have that.”

“Well, no wonder you missed those goals, and no wonder you feel really depressed and like a failure. You’ve been telling yourself that you’re not successful if you don’t hit these goals, but you don’t have a plan or a path to hit them.”

Sometimes it’s supposed to be centering, energizing, and creating focus, but if it’s too big, it’s just going to shut you down. Then you’re going to start thinking how to get around the problem as opposed to just doing the actions and activities that get you to the goal.

James Wightman (00:46:59)

Yeah, absolutely. One of the best ways for any leaders or business owners listening—especially when you have these quotas and goals for your team—is to understand their individual visions.

What I’ve found, especially when people have team members where they’re like, “I don’t know how this person’s doing; do I want them or don’t I want them?”—one of the most meaningful conversations you can have with someone is about the vision of what they really want for their life. What are they looking forward to? What are they wanting to do?

That is actually a way that a lot of business owners have peacefully separated with team members, because it occurred to the team member: “Why am I here?” The owner was like, “Well, let’s help you reach your vision.” They were able to get them a different connection or make recommendations, and they were able to peacefully separate and still remain friends or connected. At the same time, for the people that did want to be there, it only fueled them and created a better relationship.

John SmallMtn (00:48:27)

Changing gears a little bit, because I have some notes here about things we talked about to get set up for this call. One of the things you talked about, which is very interesting, is overthinking and over-planning killing early opportunities. I am by default a man with a plan; I need to have a plan and some very clear expectations. How does overthinking and shutting it down show up for you, and how do you work with people to keep them from making that same mistake?

James Wightman (00:48:56)

Yeah, this is interesting. I think it ties into the decision-making we were talking about earlier. The way that I think of this is when we’re not directly involved in something yet, we can often see opportunity. We can see possibility and what we’re moving towards, and we can be lit up and excited.

At some point when we’re in it, there’s going to be a moment—Seth Godin calls it “the dip”—where it’s like: “Is this working? Do I need to change gears?” All these different things. In those moments, I always encourage people to reference where they were in the beginning.

Sometimes we want to have a sense of: “Is this really solid?” We might just be going through a moment where we’re in the middle of it, versus: “Is this something that even in the beginning we weren’t that excited about, and it’s just something on a board that we didn’t think through?” That might be something to drop.

However, if you were excited in the beginning, if it was clear, if you saw clear opportunity before you were even tied into it, and most of what you’re doing is working, then you’re probably on the right path. You might just be going through a moment. I always like to reference: what was the beginning? What was the start? I’ve just found that useful myself in case there have been moments.

Because yeah, that can easily happen. We can over-plan, we can think through something, we can… I don’t say analyze, I say “anal-ize,” because we’re being anal about it—we’re looking at every little detail. That’s when we start to focus on the cracks in things rather than looking at things as a whole and the things that are going well. Is it just a small piece and we’re focusing on it, or if we zoom out, are most things going well and there’s just this one piece that needs to be adjusted?

Did that answer what you were thinking?

John SmallMtn (00:51:17)

Yeah. People need to be moving slow when they’re listening to this to be able to hear what is being said there.

The other thing—and I think this leads to this question—you talked about one of the bigger struggles being keeping focus where it needs to be, not just being productive and staying busy, but actually being effective. How do you work on that for yourself, and how do you work on that with clients who are clinging to, “I just want to feel busy, I just want to check things off and check the boxes”?

James Wightman (00:51:59)

There are a few pieces here. For me, I typically am a big fan of doing a brain dump of things, whether it’s to-do lists or whatever it might be. Then I look at that and ask, “Here are all the things on my list. What’s the purpose of me doing these things?” A general purpose—you don’t have to get too detailed for each one. “And is there a more effective way for me to approach this? Is there one thing that I could do that would take care of a whole bunch of these things on the list?”

I’ll use the example of that one client who said being a light in the community. If we had gone over every single thing that was on his to-do list about, “I need to fix this about the business, fix this with the company, and move these people around,” that would have taken a lot of different strategy and effort.

When he understood how to have more effective and powerful conversations with his people, that took care of a few things: it took care of building a better relationship, building respect again with each other, and on top of that, it led to understanding the difference in how they operate.

A lot of businesses will use SOPs (standard operating procedures) and pass those off. But one of the things that I like to share is that there’s a concept called expectations versus agreements. When I train people on conversations, they don’t realize that they have so many expectations, and their employees have expectations. So how do you start to form agreements with people?

Some business owners will be like, “Well, I do have expectations. I’ve hired them, this is the role.” That’s great and all, but you’re still encountering these issues. So how about we talk about how to form proper agreements? When they understand how to form proper agreements, it can take care of so many to-dos, because they no longer have the monkey on their back and they’re able to give the work back to the person if they ask.

There are these little micro-adjustments that can be very effective. That’s the way that I like to think about it: what are some small tweaks that you can make that might take care of a few things on the list? With this person, it was the conversations. That took care of the relationship, how they operated the business, and having agreements on how things worked instead of just having expectations. That took so much off the owner’s plate that allowed him to focus on his zone of genius, cleared up more of his to-do list, and actually allowed other people to operate in their zone of genius and feel like they were helping. They had a better sense of their role; it became very clear.

That’s what I mean by really focusing on being effective over productive. It can be so tempting to be like, “Hey, I got these things on the list and I need to do them.” But what you’re doing is stealing away your own time and opportunity to relax, to spend time with family, and to have time to reset.

John SmallMtn (00:55:33)

Absolutely. I always find it interesting whenever someone I work with for a while starts to see how the stuff that we’re talking about in their sales conversations starts to show up in all of their conversations if they’re open to it. They’ll always come in and be like, “John, I got to do this technique.”

I’m like, “Okay, cool. In a sales call?”

“Well, no, I was talking with a friend or a family member.”

“Okay, cool.”

There’s always this moment of, “Am I supposed to be doing this over here?” It’s like, these are not just ways to convert deals and manipulate people. This is just communicating in a face-up manner.

What I find is a lot of leaders are expecting to be heard, but they don’t always put in the effort to broadcast well and make sure that they’ve actually got really clean, clear agreements with people. The same qualities that lead to high-level sales performance are the same concepts that leadership people need to be working on for themselves and their own broadcasting, because they’re selling to an interior customer, which is their team or their people.

Salespeople—it’s a trial by fire, right? If you can’t actually get a real connection with someone and get their walls down, you’re not getting a deal done. You’re going to be on borrowed time, and it’s going to be some very uncomfortable conversations. But leadership people—it takes them longer, I would say, to see some of these gaps in how they broadcast and how they communicate with their people.

James Wightman (00:56:54)

Yeah. There’s a great book that I love—I think by John Maxwell—called The 5 Levels of Leadership. He talks about how there are five levels of leadership. You don’t have to read the book; there’s like a 20-minute YouTube video. But he talks about how a lot of times leaders will just think they’re on level five with everybody, when really you’re on level one. They’re there because you’re paying them, and that’s the reason that they’re there. You haven’t built a relationship, you haven’t earned trust, and they aren’t experiencing servant leadership from you.

If they can realize that with every person they meet, you’re on level one—they don’t really know you, and you get to build a relationship there—it doesn’t have to go slow. It can absolutely go very smoothly and fast with people. That varies, but yeah, I think that it’s just a really powerful concept that can change the way especially leaders and owners see how somebody’s showing up. Because they might just be like, “Okay, you’re the owner, you’re my boss, I’m listening to you because you’re my boss and you’re paying me.” But once you can build more of a real connection, you’re going to have someone really caring about the business and caring about you, and it makes a big difference.

John SmallMtn (00:58:32)

Absolutely. I love that idea that you shouldn’t be walking around expecting to start at a five. Salespeople have to learn this so quickly, because I spent 10 years struggling with this concept of, “Hey, I’m pretty smart, you should just listen to me,” as opposed to, “How do I get them excited to listen, and how do I earn the trust so that way whenever we do have the challenge of perception, a way of thinking, or whatever, they go with me and they don’t just get defensive and try to shut it down?”

That’s as much art as it is skill for salespeople. But I love that idea that you shouldn’t be expecting to just start from a place of trust with everybody; you do need to earn it. That’s really well said.

Switching gears, because I want to be super respectful of your time, James, and really appreciate you coming on here: as a coach—and there’s lots of ideas about coaching, as we’ve been talking about here—if someone is going out on their own, at what stage would you recommend that they get a coach? How would you advise a brand-new founder to think about finding a coach, finding accountability, and finding someone that can do this? Is that something that they start with? Is there a certain place or time in their developmental path where it makes more sense to seek this out? What are your thoughts on that for someone who’s brand new?

James Wightman (01:00:01)

Yeah, absolutely. I love this because I was talking to someone the other day who invests in businesses, and they said, “Hey James, I have different founders, and I think at different times they’re going to need a coach.”

Speaking directly to your question, I think there’s a few things to consider. There’s consulting and there’s coaching. To make it really clear for people, consulting can be very helpful when you want to have direction, a strategy, or a plan for something. So if someone is needing something in that realm, consulting can be really helpful.

When it comes to coaching, typically coaching is going to be more about tapping into your inner wisdom and taking action on the things that you already know that you’ve learned. As someone’s on their path and on their journey, I would have them check in with themselves: Have they gone through trainings? Do they know enough that they have a clear sense of the steps that they need to take? That can be very helpful.

So, do you need more strategy? There are educational aspects to coaching, and some people may provide that. If that’s what you need, you probably want more of a strategic coach. If you know your stuff and it’s more about taking action, having a reset during the week, or wanting to make sure that you have someone that’s helping you bring out your inner wisdom in the direction that you want to go, then I’d probably look more for a traditional-style coach. There are blends of these, but that’s how I would look for one.

In terms of where somebody is at in their journey, there’s a concept in coaching that a good coach always has a coach, because it’s part of the growth. For someone that’s a business owner and a founder going out on their own, ask yourself: Are you needing strategy, or is it more that you’re wanting to personally develop so you can take action? That’s the way that I would think about it. It’s more, “What’s the thing that you need at the time?”

I know people that have all different coaches or coaches throughout many different times. If you find that you are going between a lot of different coaches, the question you might want to ask yourself is, “What has me going to so many different coaches?” Sometimes someone will be like, “I have five coaches right now.” I’m like, “Well, what are you getting from those coaches that you could get from one really good coach?” Not that that’s good or bad, it’s just something to consider—being open to what they really need support with in the moment.

John SmallMtn (01:03:06)

Hmm, that’s a great answer.

When you think about your path, what is the lesson that you can now see and appreciate—the tweet or the LinkedIn post—that really resonates now, but you had to go through it and learn it the hard way before you could appreciate it?

James Wightman (01:03:25)

Mmm. Yeah, I remember I was in a session, and the wisdom that came through was: pursue what is meaningful and not what is expedient.

John SmallMtn (01:03:39)

Okay, yeah.

James Wightman (01:03:40)

For a long time, I really chased what was expedient—the next win, the next result. What I would say is when you can really get in tune with yourself on what would be meaningful to you and what would be meaningful in the life that you want to create, then it starts to become really clear the path that you’re on and what you want to do, as opposed to just trying to get the next quick win to feel good or to get the next quick thing off your plate. When you can really tune in to pursuing what’s meaningful to you, that’s what’s going to add up. That’s what will add up.

John SmallMtn (01:04:21)

Interesting. I’m going to throw you a curveball here, because I really appreciate this conversation. A lot of people try to coach—they hit the scene, they try, and a lot of people flame out or make pivots. I’m not judging anybody who makes a pivot or decides to go do something else. What is something that someone who is thinking about becoming a coach should be thinking or feeling that indicates that coaching is the right path for them?

James Wightman (01:04:50)

Yeah, I love that. And if you hear any screaming, that could be my child.

John SmallMtn (01:04:55)

You’re totally good, man. Absolutely.

James Wightman (01:04:57)

I think there are a few things here that I really love and think are important. Someone can look at coaching and say, “Hey, there’s no overhead.” That’s actually one of the things that made me fall in love with coaching. There’s a Bob Proctor quote where he talks about how if you dropped him in any country, he could still become rich even without knowing anybody, and it had to do with conversations. I became fascinated: How can you create money out of thin air, just through our words? That’s appealing with coaching.

Here’s what I think people should know when you look at the coaching industry. First, let me start with someone who might be looking at this: You have to ask yourself, do you really enjoy time with people? If you don’t enjoy time with people, I would not recommend going into coaching. However, if you do enjoy time with people, then yes, coaching could be really great. It’s more about helping people tap into their inner wisdom, and yes, you may have strategies to teach that they could learn.

Knowing that there’s that balance, if you can hold a balance between, “I’m not just teaching, I’m going to give the space for someone to come into their own wisdom,” then yes, coaching could be very good. I think it’s just really key around enjoying spending time with people, knowing that things can happen fast, but giving yourself space to create. If you are entering into coaching, still have a way for money to be coming in, just in case things don’t move as fast as you would like. Those are some things to think about as someone’s looking at the coaching industry.

Here’s something I think they should know: Most of what you see online is educational programs that are called coaching, but that is not the true essence of coaching. Educational programs are great—you may see a bunch of people in a group teaching something, and that can be very useful. People approach ads or organic marketing, and those things can work. What I think is really important to place emphasis on is understanding how to have powerful conversations.

There’s a gentleman named Steve Chandler who is great to learn from. But it’s: “How can I have a conversation so powerful with someone that they would want to continue doing more together?” They may ask, because here’s what I’ve found: A lot of times people focus on organic marketing or ads and a lot of these other things, and it’s not always reliable. What is very reliable, especially as you’re starting out and building your business, is knowing how many people you’re having a conversation with to make a difference for, and making invitations. That is so easy to count, and it’s clear whether you are doing what is needed—not to get clients, but to create clients.

That’s what I would say. I think that’s an important distinction for people, because many times people come to me and they’re like, “James, I tried organic marketing, I tried ads, I did these things.”

I’m like, “Do you have conversations during the week? Let me see your calendar.”

John SmallMtn (01:08:33)

And it’s bone dry, right?

James Wightman (01:08:36)

Yeah, because a lot of times they’re so focused on the strategy, the post, or whatever seems appealing that might feel good so we can look like a personality talking. It’s appealing, but it takes a lot.

John SmallMtn (01:08:55)

Two very important things that I would love to zero in on there: Having opinions about things and thinking that your job as the coach is just to shout your opinions and make people follow your opinion is not coaching. Half of the battle of being an opinionated person and a subject matter expert if you’re coaching other people is shutting up so that way you’re providing a path for them to see it.

As a kid, I would go ask my mom what a word meant, and her universal answer was, “Well, if you look it up, you’ll then know for yourself.” To me, I think a lot of people think, “Well, I’m smart, I’m opinionated, I’ve got hard opinions.” That does not mean that you’re ready to be a coach; it just means you might be ready to be a pundit. Being a good coach is creating the space for them to find the right answer for them that they can action.

That’s what I’m hearing behind what you’re saying: You have to be good enough and practice enough, not just at the skill or the craft that you’re trying to coach on, but you have to develop yourself as a coach so that way you can shut up and ask, “Is that the right way to do it?” as opposed to, “Hey dummy, don’t do that.” It takes a lot of space and development of yourself to be that kind of coach.

The other part that you were talking about there at the end was if you don’t want to have conversations with people, you’re not in the right lane. I was working with someone, and they had a call. I was like, “Cool, how’d the call go?”

“Man, it was a complete waste of time.”

“Okay, why?”

“Well, they didn’t know what they wanted. They weren’t ready to buy.”

“So someone actually came to you early enough in their research and process that they’re not clear, and they’re looking to you as someone who can help guide them to this thing, and you think you’re too good for that? You think that’s not part of it? Who was going to educate and inform them? When are you going to get a better opportunity to improve your understanding of how your people operate and think if you’re not having those kinds of conversations?”

It’s always flooring to me whenever I’m talking to someone who wants to be a consultant, but they’re like, “Well, I’m not getting on a call until they’re ready to buy.”

I’m like, “Cool, this is not going to work for you.”

Because I’m an introverted guy, right? I love hopping on calls and helping people troubleshoot through their calls. There are a lot of social situations that drain my battery, but that actually gets me excited and ramped up. If you don’t like talking to these people about these problems, their challenges, and their gaps, you’re not going to make it. It’s just categorically not happening.

Thank you for talking about that, because it’s something that I have to bludgeon people with. “John, is it really that deep?” And it’s like, you’re going to build a whole business around this thing, and you don’t even want to talk to these people? There’s no snowball’s chance in hell of you actually getting to where you’re trying to go if you don’t want to talk to the people. That doesn’t make any sense.

Thank you for addressing that point, because once you see it, you can’t unsee it. But I’ve met so many people that are resistant to going and having those early-stage conversations and just learning from the people that they want to serve. If you don’t get past this, you need to go find something else to do.

James Wightman (01:12:19)

Yeah, absolutely. There are just so many people in the world. Some people know, and some people are figuring it out. But the more you can be open to really being of service to somebody, the more people there are to meet and connect with.

John SmallMtn (01:12:35)

Absolutely. Last question, James: When you’ve been in the space for a while, and the world is obviously changing every day with all these AI tools and everything, for someone who’s going to start today and put themselves out there as a coach, what is your advice for day one?

James Wightman (01:12:56)

Day one: look at the people closest to you. Meet with them, connect with them, understand what’s happening in their world, and truly listen. Most people hear what’s happening for someone else and they’re just going, “Okay, well, hopefully you figure that out,” when you very well may be able to help them and make an invitation to speak more about potentially helping them.

It’s so tempting to search everywhere else but the people closest around us. You have friends, you have family, and you have people that you’ve connected with over the years. Check in and see how they’re doing, because they are even more likely to hire you, and they’ll hire you because you’re creating a committed time to be together and not just listen as a friend.

John SmallMtn (01:13:58)

Yeah, it’s always odd to me whenever people don’t want to go to their existing network for those initial conversations, because they’ve never tapped their network or been a big networker. So they would rather turn to completely cold traffic—people who don’t know them at all—than face a little bit of discomfort over here by opening themselves up and trying to get conversations where there’s the highest likelihood when you’re new. I love that.

James Wightman (01:14:21)

Right.

John SmallMtn (01:14:22)

James, I really appreciate the time. This was such a deep conversation. As I said, I’m hoping that everyone is down a couple of gears so that way they can hear some of this deeper nuance that we’re talking about. If people want to come learn more about you and the work that you do, where would you invite them to follow up and hang out with you?

James Wightman (01:14:41)

Yeah, absolutely. I’ll say something that most people probably wouldn’t: even if you’re getting to the end of this interview, listen to it again, because there is so much gold in here if you are open to truly receiving it.

The other thing that I know a lot of people say at the end of an interview is, “Shoot me a message.” What I would encourage you to do is, if you hear something in here for yourself, let me know, because that’s how I know that what I’m talking about in the work that I’m doing is making a difference.

I’ve served so many people over the years that I’m happy to share a resource, an additional interview, or something specific on what might be happening. I’ve covered things on relationships and all different topics. Whatever you hear for yourself, you can find me at jmwightman.com—that’s J-M-W-I-G-H-T-M-A-N dot com. You can see client stories there, and if you have something for yourself, just shoot me a message and we’ll go from there.

John SmallMtn (01:15:53)

Awesome. James, thank you so much for doing this. There have been a couple of people who have made genuine asks like that, and it’s really cool whenever people do, so I hope that people take you up on it. If they feel something from this, or they’ve got some new perspective, I hope they reach out to you. I really appreciate you coming on. I think this is going to help people that are moving slow enough that they’re open to some new ideas. Really appreciate the time, man. I hope you enjoy the rest of your day.

James Wightman (01:16:22)

Thank you so much for having me, you too, and I appreciate everyone who’s listening.

John SmallMtn (01:16:26)

Awesome. Have a great day.