Tony Leonard on Career Coaching for Creative Professionals

Today we’re talking to Tony Leonard. Tony is a career coach who has over 13 years of experience working mainly with creative professionals. He contends creative people, of all types, often struggle with being valued in the marketplace. I hope you enjoy.

Clinton Henry: Tony, thanks so much for being here. One of the reasons I'm excited to have you on is because I talk to a lot of coaches, leadership coaches, just career coaches. From your perspective, what is unique about working as a career coach, focusing on creative professionals?

Tony Leonard: Thanks for having me on, Clinton. Appreciate it. Creative professionals oftentimes struggle in a marketplace. A lot of creatives do their creative work, and the primary driver is not oftentimes money. It's not often financial. Not usually, but in my experience often. It's about the creativity itself. And so I'm hoping folks that in a lot of cases I'm not driven to make a lot of money or have not approached the financial space with a lot of confidence. And trying to help those people value themselves and their work, which is huge when you're talking about creative people, how is creativity appreciated and valued in a particular marketplace and helping folks identify that and then subsequently get paid well.

Clinton Henry: That's interesting. So there's a wonderful book called Drive by Dan Pink where he talks about money. It can be a motivator to a certain point. And then beyond that, we focus on other things like autonomy, mastery and purpose. I think what I'm hearing from you is that creative professionals are really focused on how their work impacts the broader picture and how they align what they do with the larger mission of the organization. Is that a fair read?

Tony Leonard: Yeah. That's fair. I think the creative folks that I work with care a lot about the mission and the values of the organization of the company. And in addition to that, they want to bring their own unique creativity to the fold. As you say, money is a driver, but there are several. A lot of the people that I work with come to me because that's the persuasive energy that's sometimes necessary to advocate for oneself. For example, in a job negotiation, salary negotiation. That's not always what folks have have been interested in and specialized in. And so yes definitely people care about the values and the core principles of the organization. And how do you bring your own creativity, like you said autonomy in as well.

Clinton Henry: So what's the typical impetus for someone reaching out to you looking for coaching services? Is it they're unhappy in their current role or is it more of a like there's something missing, what brings people to your doorstep?

Tony Leonard: Yeah, what's really for me is a lot of people come and they're completely lost. Like, I'm in this job that is a dead end or lots of folks recently getting laid off, but many saying, I have this expertise of the last ten years. I don't want to pivot to something new, but really the feeling of being stuck. And it's my job to help that individual get some clarity on where they want to go and how I'm going to bring my expertise to help them get there. In addition, what's cool about being a creative career coach is that I also get people who come from jobs that wouldn't have a creative title. They're not a UX designer, for example. But they want more creativity in their professional lives. So I get people coming from that direction as well, where they're like, creativity is not a big part of my role and I would like to bring more of it to the table. And also, there's ways of being creative in almost any position you can think of, just thinking in unique and different ways and bringing ideas that you have to the forefront.

Clinton Henry: So when you get somebody coming to you saying, hey, listen, I'm not happy in my current role, maybe I want to change, maybe I don't. What sort of your process to kind of have I guess, series of conversations with them to determine what the right move is? Do you have a regiment you follow or is it each person you approach it differently? What's your approach?

Tony Leonard: Yeah. I don't have a regimen. I'm largely working intuitively, and it starts with deep listening. I'm listening to understand the person's context, motivations, struggles, challenges, gifts, talents. And that helps me begin to think about the map forward and how quickly I can roll my expertise out and start to assist and make change. But for everybody, the timeline is different. Some people are ready to go from week one. They're ready to pivot week two. Some people it takes ten weeks. Some people, it could be six months. So the timing is different. I'm totally agnostic in the sense if you want to stay at your current role and figure out how to make it better, cool. If you want to move to a role that's in the same industry, but it's not working for the same company, let's say cool. And if you want to completely get into something totally new and different, great. I think for me it's about listening, identifying strengths, challenges and then helping roll that out in creating a process and helping that person believe in that process and ultimately just buying in.

Clinton Henry: That's fascinating. So one of the things that we deal with because I'm a leader in an organization and I lead both creative and creative individuals, my read is managing and leading creative folks is wildly different than managing non-creatives. Is there any truth to that or is that my own biases? What are some of the things that maybe creatives need more of or less of than someone who doesn't fit in that category?

Tony Leonard: The deeper question of how are we all as humans wired, I don't know the answer to that. But I do think definitely people show up in the workplace differently. Some people, they're more comfortable being given a task and saying, okay, I'm going to work on this, here's the output and it's really clear. And then there's other folks who are not going to be stimulated by that process in the same way. Creative people have a sense of wanting to do it their own way a lot of times. So you're dealing with how do you create space? Actually in one of your previous podcasts called Creating a Culture of Innovation, it's really interesting. I think everybody should listen to it. You talk about some of the key things about creating a culture of innovation, and one of them is psychological safety. That's huge. And so when you're managing somebody who wants to be creative, who wants to bring ideas to the table, we have to create that space. This is something that I bring to my coaching as well. I try to bring as non-judgment like we're not going to judge the outcome. We're going to allow you to work in an iterative way and it hopefully leads to some value add for the organization. That's always the balance is, how much flexibility space do you give somebody and then you also need results. I think you could call it a tension or a problem to solve, but makes working with creative folks interesting.

Clinton Henry: So how do you handle someone who says, Hey, look, I'm not creative, but I'd like to leverage more of those skills in my work or I'm creative outside of work, but I want to be creative in work. How do you approach that? It seems like a really unique conversation. I think COVID did a lot where a lot of us re-examined what we do and why we do it. I imagine the trend of people saying, what am I spending my time doing and am I getting real value out of it? What advice do you give them and how do you have them approach that situation?

Tony Leonard: For me, it starts with really listening. I'm again, not coming in with an objective. I'm trying to understand what are you doing now concretely at work? Walk me through day to day, hour by hour. Let me really understand what you're doing. What are you doing outside of work that you feel falls more into what we would call in, "a creative activity." And how do you want to bring more creativity into your work life? That's a conversation. The more that I can hear about that, the more that that person is willing to tell me, then it's going to help me advise them. I think anybody who's managing folks, really trying to listen with the intent to understand and then it's about coming up with a plan. And then it's like, okay, now I understand where you're coming from. Let's hear some ideas I have. Let me hear some ideas that you have. And if we can get locked in on a path forward, then if the manager is flexible and was like, I want to try to make this work. I mean, that's exciting. That's exciting for me, giving that person the opportunity to do their thing in a new way. And also for the manager to stand back and say, let's see how this goes. And hopefully it's good.

Clinton Henry: Yeah, people are usually pretty intuitive. They kind of know what they'd be good or bad at. The amount of career conversations that I've had with people on my team or other leaders that I work with where somebody just said, Hey, listen, I've been doing this for 15 years and I don't want to do this anymore. This looks interesting. Can I have the autonomy to go explore that? It's a very interesting question to hear, but it's so empowering when you actually let somebody do it and it's successful. It's actually a lot of fun because you feel like you've actually done your job as a manager. It's more than just top grading or evaluating talent where you're empowering somebody to actually get more value out of what they do day to day.

Tony Leonard: Yeah. You're helping them be more fully human being, getting to express their humanity. And maybe they wanted to do something when they're 25, and now they're 37 and they've changed a lot in that time and their priorities are different and goals are different, family relationships are different. And so if you can allow somebody the space. It begins with a conversation and just having those open questions and then saying, okay, I'm committed to your growth as a human. I'm also deeply taking into consideration the demands of what the company needs. I need to make sure that revenue is being created and so we're balancing that. But if we can give more space. This is where I feel I could be adding even more value. I've more passion here. If you can help that person get from A to B, you may end up getting an employee who's giving you a lot more value. They're more locked in, they're more passionate, and they're going to be adding more to the company.

Clinton Henry: Yeah, if your employee count stays the same, but your level of engagement from the employees goes up, productivity and everything else goes up too. So I think increasing engagement is really important and having people get value from what they do is a big path to accomplish that. Typically, how long do your coaching engagements last? So is it one of those things where somebody is doing a session once. I got to figure this out over a few months, how does that work? And the reason I'm asking this is a lot of times we talk to leaders about the importance of having coaching conversations with their team members and they're like, Oh yeah, I booked it, we're good. And it's a one and done thing. I very much doubt that's going to be the appropriate approach I just wanted to kind of tee you up with.

Tony Leonard: Yeah, I prefer to work with people in the range of three months to six months. It gives somebody the opportunity to think a little bit deeper possibly about what they really want to do. I do an exercise with most clients at the beginning where it's like, let's take one piece of paper and a pen and write down as expansively as you can everything that you'd like to do professionally in your life going back to when you were in the second grade. And then from there, maybe the following week we start to see what resonates and what doesn't. A lot of these things kind of fall off the radar, and that's fine. Then we start getting locked into a few that are like this is interesting. And it's really interesting for me because sometimes that thing once you've given the space to think completely expansively, person really comes back to what they're doing. And it just is about I've had clients, they just needed to have some difficult conversations with their managers so that they can tweak their role a little bit and get a little bit more clarity and understanding and support. And then sometimes it's wildly like I want to listen to Bob Dylan and make whiskey. Like I'm through with the C-suite. So if you give people opportunity to think really expansively and you're like not confined for moments. But going back to your question, yeah, I think it's a longer process. I think one coaching session is great. It opens the door. It says, here's a potential pathway but usually folks need more than one to make change.

Clinton Henry: Yeah. I get it. When you mentioned the whiskey thing, I just thought about this guy that used to work for me in Texas. And then we had a few conversations. His heart wasn't in it. This was before quitting became a thing. I just could tell he wasn't that engaged. And it took a few conversations. He finally opened up and I'm like, What do you want to do, man? What do you want to do? He is like, I really want to get into cheese. And he's actually a very successful cheese maker now in Austin. It's crazy. Like people have these things.

Tony Leonard: Yeah. People bring all of the talents that they've built and the skills that they've built and gained through their experience. For example, probably this guy who works with you got a lot out of the experience working with you, and he's using a lot of that in his cheese business. It just happens to be cheese. That's fantastic.

Clinton Henry: Exactly. I think that's one of the great things about your role as you're helping people live their best life or be more human, as you said. I think that's a wonderful way to live and a wonderful way to spend your time empowering other people. Tony, I just want to thank you for being on the show, giving us a little bit of insight about what you do, your contact information and your site will be in the show notes for people to check you out. But this was great, man. Thanks so much for coming on.

Tony Leonard: Thank you Clinton. I appreciate it. It's been a pleasure.

Clinton Henry: Take care.