
Jennifer Whitcomb, Principal of The Trillium Group is a seasoned leadership and executive coach with over 25 years of experience working with leaders across five continents. Renowned for her ability to help leaders navigate complex challenges, she partners with clients to enhance their presence, clarify their vision, and create actionable strategies for growth and success.
Her coaching philosophy centers on the belief that leadership development is an ongoing journey. She specializes in helping leaders unlock their full potential by fostering self-awareness, resilience, and authentic communication. Through a customized, results-oriented approach, Jennifer empowers clients to identify obstacles, leverage their strengths, and achieve their most ambitious goals.
Her coaching process is collaborative and tailored, providing a confidential space for leaders to gain new perspectives, broaden their skills, and receive honest, supportive feedback. Jennifer is known for her warmth, integrity, and practical wisdom, helping clients move forward with clarity and confidence.
She is a former Director and faculty member of the Leadership Coaching Certificate Program and Organization Development Program at Georgetown University. As one of only 4% of coaches worldwide to achieve the Master Coach Certification, Jennifer is recognized for her commitment to excellence in the coaching profession.
Outside of her coaching work, she enjoys making award-winning jam and playing pickleball.
Connect with Jennifer on LinkedIn.
What You’ll Learn in This Episode
- When to consider working with an executive coach
- How to choose an executive coach
- What are the advantages of working with a coach
This transcript is machine transcribed by Sonix
TRANSCRIPT
Intro: Broadcasting live from the Business RadioX studios in Atlanta, Georgia. It’s time for High Velocity Radio.
Lee Kantor: Lee Kantor here. Another episode of High Velocity Radio in. This is going to be a good one. Today on the show we have Jennifer Whitcomb and she is with the Trillium Group. Welcome.
Jennifer Whitcomb: Thank you. We appreciate to be here.
Lee Kantor: Well, I am so excited to learn what you’re up to. Tell us about the Trillium Group. How are you serving folks?
Jennifer Whitcomb: Yeah, so I work with people now for over 30 years and primarily in leadership development, and most of my work now is one on one. I tend to work with senior level executives to help them with whatever they may be faced with at the time and, and to be more successful so they can put their best step forward.
Lee Kantor: Now, when you’re working with a senior level executive in this type of executive coaching is that usually because that individual raised their hand and said, hey, Jennifer, I’m interested, or is it something that organizations now are just saying, you know what, we have to put our leadership team, you know, we’re going to pair them with coaches to get the most out of them.
Jennifer Whitcomb: Yes. I think that’s a great question, Lee, because I swear, like it. It happens in all kinds of ways. Like primarily my client is the organization and sometimes there’s a succession plan going on. And so people are being tapped to be the next leader of their area or another area. And then they may say, hey, it might be helpful for you to work with a coach to help you prepare for that. And other times people say, hey, I’m, I would love to work with a coach. Can you please find one for me? So I just doing some work now with somebody who just selected me to work with her and she volunteered. She said, hey, I, I really feel I’m at a place right now. I’m dealing with a particular challenge and I want a coach to help me with that. So all kinds of ways people come and it may be part of a an existing leadership development program, and they’ve got a pool of coaches that they want to use to support that that effort.
Lee Kantor: Mhm. Now when you’re working with a person coming from one of those two ways, is there a different way you approach that or is it kind of the same from your lens?
Jennifer Whitcomb: I would say it’s the same. I mean the the client is of course my organization and my client is also the client themselves. Right. So I want to make sure that that everybody gets the results that they’re looking for. And often the organization wants a particular result and then the individual may want a result. And so I look at how do I bring those two together so that everybody’s happy.
Lee Kantor: So is that that to me is where it could possibly get tricky, because how about after talking with the, you know, the the client, not the organization, but the, the executive, the they realize maybe I shouldn’t be here in this organization like that. That’s kind of the outcome.
Jennifer Whitcomb: That that, um, that often comes up. Right. Because it may be, especially if they raise their hand to say, well, I want to work with somebody. And usually as part of the process, I will ask the organizational client if I’m to work with this person, what happens if that person decides that they do want to leave the organization? And it sometimes happens because people beget more self-awareness, they start learning more about themselves. They get clarity about what their values are. They start questioning things. Am I in the right role? Am I in the right job? Is this the place for me? All of those things. Right. So and I think it’s, it’s part of for me when I’m doing my contracting to make sure that I ask that question. And, and if they say no, well then that’s not the client for me. Right. So yeah.
Lee Kantor: Right. So you address that upfront because that is a possible outcome that, you know, from dealing with these type of people that, that that could happen. Um, yeah. And you have to be the you’re kind of advocating for that, that executive. Not necessarily the organization might be your client, but you can’t just not talk about things.
Jennifer Whitcomb: Right? Right. And and then it becomes a bit of a conflict of interest. Right. So you’ve got to be very careful about like, so who is the client. Right. And I think most of the time it is the organization. And when people say, well, I do want to make a a career change, then I’ll say, well, like I’m probably not the one for you, right? So it just it just depends, right? It just depends, you know, what’s the level of clarity and agreement with everybody before we even get started?
Lee Kantor: Right. And then it’s important to be transparent for all of the parties so they understand that they can comfortably share something with you.
Jennifer Whitcomb: Yes.
Lee Kantor: Right. Because that that’s a that’s one of the key components of coaching, right, is to to be able to be vulnerable and share these things that maybe you wouldn’t or you are kind of struggling with.
Jennifer Whitcomb: Exactly, exactly. And so and I want to create that environment where somebody can feel that way too. Right. So and sometimes the organization is quite happy to say, yes, you know, it’s totally fine if, if you talk about that because either the position is going away anyway or it might be ready for that person to make a move. So they’re quite supportive of that. And it’s just good to know that up front.
Lee Kantor: Yeah I mean I think that in order to really serve everybody, you have to have that level of transparency and authenticity in order to, um, you know, create the best outcome for everybody because the organization, it’s good for them to know that, oh, this person’s got one foot out the door. I’d rather know that today than in six months after I’m investing all this time into them.
Jennifer Whitcomb: Yes. And money. So. And then you know and I’ll, I’ll sometimes suggest like if the organization is great with it, fine. And if the organization is not, I say, well, that’d be something you want to do on your own. Right. Find a nice career coach for you to work with.
Lee Kantor: Right. Well, I mean, so what’s your backstory? How’d you get involved in this line of work?
Jennifer Whitcomb: Well, I was, um, I was doing a some different work, and I’d always had a background in training and development and working with teams, and, um, I noticed that a lot of my colleagues were were moving over to coaching, and I’ve always enjoyed working one on one with people. And I was informally doing that as part of when organizations would work with me around their team. I’d interview the leader, and sometimes that would be where I would start is to work with the leader first before bringing it out to the team. Um, because sometimes I would do some assessment and talk to people, and I would get information about the leader that I would give to the leader because they’d ask for it. And I said, well, I’m wondering if you and I should start working together.
Lee Kantor: You might have some blind spots.
Jennifer Whitcomb: What’s your level of openness around that?
Jennifer Whitcomb: So. So, so often we would and then I think, you know, the field of coaching was, was just getting going. And I thought, I think it’s time for me to start, you know, learning more and getting trained as a coach. So so that was it. And then, um, I had run Georgetown’s Organization Development Certificate program at one point, as well as running my consulting practice. And then, um. And then I thought, huh? So then there was a coach, a leadership coaching program, and then I ran that program. And so I got to see all my colleagues again in that program. So it was all very interesting how we, a lot of us made that transition.
Lee Kantor: Mhm. Now are you seeing more and more organizations, um, embracing coaching as just part of this is just part of how we do business now that we provide coaching for at least the leaders. And hopefully in my dream of dreams, it’ll trickle down to all of the employees. But is it at least getting comfortable as just kind of a a? It’s not a nice to have anymore. It’s a must have.
Jennifer Whitcomb: Yeah, I think it’s really changed and I think it’s continuing to change and evolve. So when I first started getting involved in coaching, I think a lot of people weren’t really sure who it was, a specially the potential recipient of coaching. They thought, oh my gosh, I’ve done something wrong, right?
Lee Kantor: Like fix Bob. Like that’s why, you know, you’re exactly.
Jennifer Whitcomb: And I mean, there still is some coaching out there. That is what I call more on the on the performance side or something’s not working and we’ve got to fix it. And um, and, and yet I would say that has changed quite a bit, where people are realizing that more and more people in the world have had coaches, especially some famous people like Oprah and, and, and, and Bill gates and and.
Lee Kantor: And every professional athlete.
Jennifer Whitcomb: Yes. And professional.
Jennifer Whitcomb: Athletes. And so I think it’s it’s becoming interesting. And I hear the word coach used for so many different things, like a wellness coach, a health coach, a fitness coach, which is, you know, you’ve heard that before, but I think the word coach is being added to lots of different things. Nutrition coach. So, um, so I think it’s just becoming just a very more, um, more common these days.
Lee Kantor: Mhm. Right. There’s no. I mean, I wouldn’t think there’s a stigma anymore about coaching. Um, maybe at one point, like you said early on it would be like, why do I need a coach? You know, I’m fine.
Jennifer Whitcomb: But yes. And in one organization I work with, it was it was viewed so positively. Where. And this is when I was doing a lot of in-person meetings, and I’d be walking down the hall with somebody and they’d say, hey, meet Jen. She’s my coach.
Lee Kantor: Right. They’d be bragging about it. It was a status symbol.
Jennifer Whitcomb: I’m proud that they got selected to that one. Right. It was a Betty right now.
Lee Kantor: Um, when a person’s choosing a coach, is there kind of some do’s and don’ts that you found over the years that, okay, this is going to probably Be a good fit. If if this. If these things happen in this manner.
Jennifer Whitcomb: Yeah. And I think it’s about, you know, what’s the right time to have a coach. Like I think like in, in one, 1 or 2 cases, I probably didn’t ask enough about just what their capacity was to be able to build this into their schedule. Right? So I usually work with people like a couple of times a month, 2 or 3 times if I can like, or within 2 to 3 weeks. And um, and some people, especially if they’ve got like a really busy schedule with travel and if they’re an exec that’s flying all over the place and it’s just it, or they’re in the middle of a merger and acquisition or something, it may not be the right time. Right? Um, or they’ve just got too much going on. So that’s one thing that I really ascertain, you know, this is an investment in you. And, um, and there’s some things that, you know, I want to make sure that this is the right time for for you to take this on. Because even though, like, I’m very sensitive to people being being very busy not to sort of have a lot of extra things between the times that we meet. But I think that’s important, and I think really getting clarity about what’s bringing them the coaching and is coaching the right answer for them, because maybe there’s something else that would be better, right? Um, and I think as they’re choosing a coach to really hopefully have a selection of people that choose from. So in my firm, I, I usually have like a handful or like six people that clients can choose from as to who they could work with. And then they usually interview a handful of people just to see is there the right fit? Is that person going to give me the best type of support I want or the best challenge that I want? Um, and I think for me, I’m a little bit biased. Lee. Is that. Um, I, I hope they choose a coach that has been trained to be a coach. So, yeah.
Lee Kantor: Now, you mentioned the time aspect of this, and I think that that brings up an important part of coaching, that the coaching experience is not just the 30 minutes or hour you spend with the coach. Right. There’s going to be pre-work homework, and it’s going to open up kind of cans of worms that get people thinking. So it’s not, oh, I can just knock this out and like boom, boom, boom, I have my session and then I’m done. And I don’t have to think about it for two weeks.
Jennifer Whitcomb: Yes, I think that’s, I think that that sometimes that people don’t realize and and it’s not that it’s a lot, but it’s, it is something to think about. Can they have the focus to dedicate this time to. Write. Can this become a priority? And and it may be where like between the times that we meet, I might have somebody reflect on something or they may or we come up with that together. And usually I’ll ask, so between now and the next time we meet. What’s something that you think that you can, you can work on to help move the needle forward to your goal that you want to achieve here? What might be one small thing, right. And they’ll say, well, can you send me a short article or I’ll, I’ll, I’ll try this on. And sometimes it’s if it’s a behavioral thing then, you know, where can they have a little bit of practice. Because there needs to be enough time between when we meet for them to try some new behaviors on, try new things. Um, so there’s someone I’m working with now that, um, he’s his, um, his stress is leaking, put it that way. So, um, and so, you know, so between now and the next time we meet, he’s really working on on just his engagement with people and having some practice with that. And one of his colleagues will give him some feedback on how that’s working. Right.
Lee Kantor: Right. But but he has to actually do it like it doesn’t work. Right. It doesn’t do that right. It doesn’t serve a purpose. Like, yeah, I should do that. And then you meet in two weeks and they’re like, yeah, I should have really done that like that. Yeah. Nobody is benefiting from that.
Jennifer Whitcomb: And I think the funny thing, Lee is, is like like I hold people accountable. And that’s part of being a coach. It’s it’s just not a nice conversation. It’s it’s just like, so when we check in next time I’m going to ask you.
Lee Kantor: Right.
Jennifer Whitcomb: And the we really are working on getting from A to B here.
Lee Kantor: Right. And the right answer isn’t yeah I heard you. It’s I did something, you know, something an action actually took place.
Jennifer Whitcomb: And folks I’ve been working with a while for a while ago okay I now I am now going to report to you what I’ve done. And I feel like you’re my probation officer. I said I’m.
Jennifer Whitcomb: Not.
Jennifer Whitcomb: I just am invested in you getting to where you want to be.
Lee Kantor: And. And they’re the ones who came up with the thing they wanted. You know, they they are the ones who have that objective. You didn’t make it up like it’s their objective.
Jennifer Whitcomb: It’s all about them. Yeah. So I have a good laugh, right? Yeah. It’s good.
Lee Kantor: Now, are you finding that young people are. I don’t want to say demanding, but it just are asking for coaching of some kind. Because I feel that young people are very attuned to their mental health. They’re attuned to, you know, wanting to, you know, be their best selves. And if an organization can really provide this type of leadership, it can really help themselves in terms of retention and, um, even recruiting new, new, uh, employees if they can, you know, serve their existing clients through something like coaching.
Jennifer Whitcomb: Yes. No, I totally agree. And because I, because I finally like I work with a lot of folks who are more at the at the, at the.
Lee Kantor: Right, probably at the top end of the organization.
Jennifer Whitcomb: And I, I often think like, like. And I do think now coaching is becoming much more available to, to employees, which is great because I think if they can learn some practices that, let’s say, help them manage their stress. Right. If if they do get stress or manage their priorities or whatever it is, because, I mean, I work with somebody recently, for example, who she was so exhausted. Right. And and I think it was because she wasn’t really clear on what her priorities were. I’m not sure where the alignment was with her boss. Right. On what she should focus in on. So I tuned in on that. I said, well, that may be a place to look at. Right. Um, and let’s have a look at your calendar. Right. So just even things like that. But I think to know some of this before you get too far along in your career is so helpful, right?
Lee Kantor: Yeah, I agree, I think that, um, I think organizations are missing out by not kind of democratizing coaching and bringing it to all levels, because I think young people are so hungry for this. And and, you know, I would hate for them their first experience with coaching. Be some AI chat bot.
Jennifer Whitcomb: Exactly. Which is what’s happening in some places. Right?
Lee Kantor: Right.
Jennifer Whitcomb: So I think just.
Jennifer Whitcomb: I think just to help them, if it’s it really sometimes it’s about self-awareness. Like what are you noticing about yourself about like when you’re your best self and what helps you get there.
Lee Kantor: Right, right. I mean and if you can picture your best self and then have the realization of where you’re at and see that gap, and then have somebody that’s kind of with fresh eyes looking at your situation that can ask you questions that help you kind of shrink that gap. I think everybody wins when that occurs.
Jennifer Whitcomb: Yes, I totally agree, I totally agree.
Jennifer Whitcomb: Um.
Jennifer Whitcomb: Yes. I think it’s becoming more available and I hope that continues. And like you say, just to have a real person as well.
Lee Kantor: Right. I think that that’s critical, I think. I think organizations are going to be making a mistake if they think like, oh, there’s an AI, you know, coach chatbot that we’re going to give to everybody. And we they’re we’ve done it coaching for everybody. And I think.
Jennifer Whitcomb: There’s and I think it’s just there’s just even like nuances about, you know, when somebody gets really quiet for a moment or you hear some emotion in, in their voice, um, or if you’re even in a on a camera to see something in their face, like it’s picking up those cues that I don’t think the AI bought. Will.
Lee Kantor: Right. I mean, how much of communication is nonverbal? I mean.
Jennifer Whitcomb: Yeah, exactly. 80% or something. Right.
Lee Kantor: So it’s we’re just going to ignore that and think we’ve solved the problem. I mean, that’s ridiculous.
Jennifer Whitcomb: And I and I sometimes think it’s what people don’t say. Right.
Lee Kantor: Right. Exactly.
Jennifer Whitcomb: And I’ll say, huh? You got really quiet there. What’s going on?
Jennifer Whitcomb: And they go, oh, you’re always, I guess, my job. I’m sorry.
Lee Kantor: I pay attention, that’s what. That’s why you hired me. I’m. I’m actually listening to what you’re saying. I’m. I’m not going to let you just blow by that. Sorry.
Jennifer Whitcomb: Right.
Jennifer Whitcomb: Yes. Uh huh.
Lee Kantor: Well, this must be such a rewarding work for you.
Jennifer Whitcomb: I really, really love it. I I’ve been doing this for a long time, and I still really enjoy it. And, um, and I just get very excited when I get a new client and I think, great, it’s time to start, you know, something new. Somebody’s got some new goals and and they’re excited and engaged, and they want to work with somebody to help them be their best self. Right?
Lee Kantor: Yeah. And and you get to see kind of the result too. It’s it’s not like some people just do a job and then they never know what happens next. I mean you’re kind of living it with them. Mhm.
Jennifer Whitcomb: Yeah. So true.
Lee Kantor: So who is the ideal client for Trillium.
Jennifer Whitcomb: Oh I think somebody for me anyway is um a senior level leader who is interested in improving themselves. They want to be a better leader perhaps. Or perhaps they’ve got like a juicy challenge or something’s going on that they want help with and that they’re open to coaching. I think that’s the key thing.
Lee Kantor: Is it is there is there something that’s happening that’s kind of like a if this is happening, you might want to consider coaching. Is there like is there kind of signs or signals or breadcrumbs for you that say, you know what, we I get a lot of my clients when this is happening and maybe they are to open their mind to coaching at that point.
Jennifer Whitcomb: Yeah. I think just um, it’s it’s often when just like, you know, I’ve got this challenge going on. Um, I worked with somebody, um, for example, recently who, um, she was new in her role, and the team had been there for quite some time, and she began to pick up that, um, that the team wasn’t really, uh, trusting of the previous leader because she would ask people to do things and she couldn’t figure out where the where the blockage was or where the holdup was, or she tried to have these transparent conversations and people weren’t really forthcoming. And I said, well, tell me a little bit about the history and, and, and how did you come to get that role? Right. So things like that. So I was able to help her have, you know, some difficult, challenging conversations with some of those people. And now she’s doing amazing, right. I mean, and I would think it was about her showing her vulnerability and and she’s such a kind soul. And I think it took them a while for her, for them to see that. But I think that’s a, um, an example where someone like myself can just really help somebody. Right?
Lee Kantor: Yeah, absolutely. Because I think that a lot of times just having somebody to just get stuff out of your own head, yes is useful.
Jennifer Whitcomb: Right. And I think sometimes it can be like the, the new role or even like navigating the politics of an organization. Sometimes people don’t realize that when you go up the next 1 or 2 levels, it’s it’s a little bit different. And really discovering like, so who are your allies and who do you need to build relationships with? Right.
Lee Kantor: Yeah. Absolutely. Yeah. And to have a person at your side, I mean, especially as you’re kind of climbing that ladder, it’s it’s got to be a must have at this point. I would think for most people that are really trying to just keep, um, you know, kind of growing as a, as an executive leader, like, you have to have that kind of voice on your shoulder that’s saying, hey, think about this or think about that or, or, you know, don’t think about this.
Jennifer Whitcomb: Yeah, I really agree. And and I think sometimes people will tell me, like, I’m the only person they can talk to.
Lee Kantor: Right? Because if you think about it like, who else can really fill that role? I mean, like a lot of times their spouse is that doesn’t have the same kind of, uh, you know, situation that they’re in. Their friends are not, uh, you know, the probably the right people to be sharing some of this stuff with. And most people have a hard time being vulnerable, uh, as it is. So to have a trusted kind of adviser like this, I think is critical.
Jennifer Whitcomb: Yes. Because. Because I hold everything in confidence. Right?
Lee Kantor: Right.
Jennifer Whitcomb: And hopefully create the space that people can feel, that they can tell me things. Right. So I think, you know, especially during the pandemic, I mean, there was someone I worked with that was he was, um, sleeping on the couch in the, in the office right at night. And, and I could tell just by looking at him, he was just, I mean, beat, right? Just so exhausted.
Lee Kantor: Right.
Jennifer Whitcomb: And he said, oh, I’m so glad I can talk to you today.
Lee Kantor: Right. It relieves weight. I mean, it takes weight off of their shoulders and, and and I would think just the I know for me personally, when I have somebody that I can just kind of just say all the stuff that I’ve been thinking. I feel lighter.
Jennifer Whitcomb: Mhm. Yes, exactly. Yeah. That’s the goal. Like oh get be lighter and get to where you want to be. Right.
Lee Kantor: Right.
Jennifer Whitcomb: Learn some new things maybe some things that you can. You can apply the next time this happens. Right.
Lee Kantor: Yeah. And it’s not a weakness. Asking for help and to have. Sometimes you need help and sometimes you need helper, you know.
Jennifer Whitcomb: Yeah, exactly. Because I know myself, I can get in my own way. Right.
Lee Kantor: Right. So if somebody wants to learn more, um, and get on your calendar or learn more about the Trillium Group, what is the website? What is the best way to connect?
Jennifer Whitcomb: I would say the website to reach out to me via email. Linkedin. Yes. Absolutely.
Lee Kantor: And the website is the Trillium group.com. Trillium is trillium.
Jennifer Whitcomb: Yes it is. Mhm. Yes. And trillium. Just so you know because it’s a long one. Um, I had no idea when I started my business that we were going to have to have all of this happening with, you know, putting it out there. So I would have chosen a shorter name. Yet. The trillium is the emblem for the province of Ontario, and that’s where I’m from. So I’m Canadian. And so I wanted to have a name of my company that was relevant to where I came from.
Lee Kantor: There you go. Well, Jennifer, thank you so much for sharing your story, doing such important work. And we appreciate you.
Jennifer Whitcomb: Oh, and thank you, Lee, for chatting with me. It was just fabulous.
Lee Kantor: All right, this is Lee Kantor. We’ll see you all next time on High Velocity Radio.














