1889 – Navigating Leadership and Entrepreneurship with Jennifer Wilson

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder and Lead Coach of Oak Bay Coaching and Consulting, Jennifer Wilson.

Wilson Wide

Jennifer Wilson is a leadership coach and the founder of Oak Bay Coaching and Consulting. Transitioning from a ski instructor and midwife to a family business leader and coach, Jennifer brings valuable insights to entrepreneurs and leaders. Her background in guiding skiers and assisting in childbirth has given her a deep understanding of human potential and the nuances of leading individuals through difficult transitions. This wealth of experience has propelled her into leadership coaching.

In discussions, Jennifer describes herself as a “thinking partner” to her clients. She adopts a non-directive role, encouraging clients to explore their solutions through introspective and powerful questions. This method promotes client autonomy and instill a sense of responsibility for their decisions and consequences.

A key focus of the discussion was Kolbe, a tool that Jennifer Wilson uses to assess individual strengths and problem-solving styles. She highlighted the importance of recognizing and utilizing these strengths and acknowledging the diversity within a team. This understanding is essential for entrepreneurs dealing with complex team dynamics.

Key Points from the Episode:

  • Jennifer Wilson's journey and transition to becoming a leadership coach
  • Her role as a thinking partner and guiding clients to solve their own problems
  • Working with clients in family businesses and women in leadership
  • Coaching framework as a passenger in the car while clients are in the driver's seat
  • The value of Kolbe in understanding problem-solving strengths
  • Challenges that entrepreneurs face, including effective delegation
  • Addressing burnout and the importance of self-reflection and leveraging strengths
  • Resources available on for new leaders and preserving organizational culture
  • Encouragement to join the Thoughtful Entrepreneur community
  • Promise to continue bringing positivity and inspiration to listeners' daily lives

About Jennifer Wilson:

Jennifer Wilson is a dedicated coach and mentor who fosters personal transformation and resilience in her clients. She perceives challenges as hidden opportunities and emphasizes the importance of understanding and utilizing one's innate talents. With a coaching career that began in earnest in 2022, Jennifer brings a wealth of experience from her diverse background, including significant roles in business, education, healthcare, and, notably, as a CEO in the family business specializing in Homestay placements for international students. Her approach is characterized by a blend of non-directive coaching and mentoring tailored to individual client needs, making her a compassionate and practical personal and professional development guide.

Jennifer's qualifications and experiences are extensive, covering a spectrum from a Bachelor of Science in Anatomy to an MBA in leadership, alongside certifications in coaching and the Kolbe Index, which she utilizes to enhance team productivity and stress management. Her life experiences, including overcoming burnout, career shifts, and personal trials, equip her with unique insights into life's complexities. Beyond her professional achievements, Jennifer is a dedicated mother, an avid mindfulness and yoga practitioner, and an enthusiast of Vancouver Island's outdoor adventures, embodying the balance and growth she encourages in her clients.

About Oak Bay Coaching and Consulting:

Oak Bay Coaching and Consulting is dedicated to unlocking the potential within its clients by fostering a culture of transformation, resilience, and positivity. With a foundation in the belief that challenges are merely opportunities in disguise, the firm focuses on assisting clients to recognize and harness their innate abilities for personal and professional growth. The firm leverages the extensive experience of its executive coaches, who bring over 17 years of leadership expertise, advanced business education, and certified coach training to the table, ensuring a well-rounded and impactful coaching experience.

The unique approach of Oak Bay Coaching and Consulting integrates the principles of the Kolbe System with strategies to overcome internal and external compassion fatigue. This combination is designed to support clients in enacting sustainable change, leading to lasting positive outcomes in their personal lives and professional careers. The firm's methodology emphasizes the importance of understanding and utilizing one's gifts, underpinned by the conviction that with the appropriate guidance and support, individuals can navigate their challenges and transform them into opportunities for success.

Tweetable Moments:

08:43 – “How do I preserve the culture of my organization as I grow? This is where I think a coach approach really adds value.”

Links Mentioned in this Episode:

Want to learn more? Check out Oak Bay Coaching and Consulting’s website at

Check out Oak Bay Coaching and Consulting on LinkedIn at

Check out Jennifer Wilson on LinkedIn at

Check out Jennifer Wilson on Facebook at

Check out Jennifer Wilson on Instagram at

Check out Jennifer Wilson’s website at

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Josh (00:00:04) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach, or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence. Com and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my influence. Com and click on podcast. We'd love to have you. With us right now it's Jennifer Wilson. Jennifer, you are a leadership coach and you were the founder of Oak Bay Coaching and Consulting. Your website is Oak Bay Coaching and Consulting. Okay, Jennifer, thank you so much for joining us.

Jennifer (00:01:13) - Thank you so much for having me. Josh, it's great to be here.

Josh (00:01:15) - Yeah, absolutely. We'll share just a bit about the work that you do and the impact you have in the world.

Jennifer (00:01:21) - Yeah. Thank you. So, as you said, I'm a coach. I came to this with a fairly circuitous route, as I'm sure a lot of the entrepreneurs you have on can say. And I'd love to share a little bit about my story and then talk about what I do. So yeah, I began my career, I suppose, as a coach back when I was 16 years old as a ski instructor, and I taught sailing not long after that, and then I became a midwife, and then I ran my family business, which is organization that places international students with host families in Canada. And you may be wondering, what does coaching have to do with all of those different careers? And I think the link for me, right from the early days as a ski instructor, was in guiding people, helping them to reach their potential. I feel I did that as a midwife, sitting alongside women through this transformational life experience, helping guide them through that, and then as a business leader in my family business, again, helping people sort of reach their potential and discover who they are, not just my employees, but the students and host families that we were serving.

Jennifer (00:02:26) - So I came to the family business sort of by accident. I went through a divorce and I couldn't continue to practice midwifery, sort of fell into that. I promised my mom that I would work with her for about five years. And then, you know, 18 years went by. but I really feel like that experience as a business leader set me up for being an excellent leadership coach now. So I bring all of that sort of experience in healthcare and business and, and my experience with teaching to my role as a coach. So these days I feel again that I'm a guide. I call myself a thinking partner. So I'm somebody who listens really curiously to where you're feeling stuck, where you have challenges in your work. And then I offer resources and mentoring for the skills gaps or knowledge gaps where you're missing information. And then I really ask powerful questions to help you solve your own problems.

Josh (00:03:30) - Yeah. And tell me more about who you work with. Your typical clients.

Jennifer (00:03:35) - Yeah. So I love working with people who have experience in family business.

Jennifer (00:03:39) - As you can imagine, I bring a lot of knowledge and expertise from my own experience into working with family business, and I served on the Family Business Association of Vancouver Island Board for several years, so I've got a lot of experience with that. I also love working with women in leadership. I think having watched my mum run two businesses before she started, the one that we ran together and having worked with many women in our company and, and helped develop and nurture a lot of women leaders in our organization, I think that's somewhere another sort of area that's close to my heart.

Josh (00:04:17) - Yeah. So it's not Jennifer that you just have like, great life experiences and great business experiences and, you know, you have obviously some soft skills as well. But also like in your engagement with clients like you come also with, you know, kind of a structured coaching framework. Can you tell me a little bit about that and why that's valuable?

Jennifer (00:04:39) - Yeah, absolutely. The coaching framework is a great way to put it in terms of the work that I do.

Jennifer (00:04:46) - So some people associate coaching with athletes and imagine that coaches are people who offer mentoring, who have expertise in an area and then share that with their clients. I see myself more as somebody who's sort of along with you on the ride, so I use a metaphor of driving a car. We're going on a road trip, and my clients are sitting in the driver's seat and I'm in the passenger seat. So when they're bringing a problem to me, the solution to that problem is the destination that they've chosen. So I'm not choosing the destination they are. They're choosing the route that they want to take. They're choosing the detours that they want to take, whether or not we're going to stop and rest at the side of the road, how fast or slow they want to go. And I'm there sitting alongside as a thinking partner. So I'm helping them make decisions. But I'm not the one in charge. It's not my agenda. So I hold the space for that conversation. I keep track of the time.

Jennifer (00:05:42) - I'm looking at sort of the direction that they're taking and helping kind of offer ideas. I feedback what I'm hearing. and I again, like I said, I ask a lot of powerful questions. So that's kind of the framework. I also bring my experience as a Colby consultant, and I can talk to people about their strengths in terms of how they take action in the world. Colby doesn't measure personality, so it's not a personality assessment like Myers-Briggs. It's a tool that helps people understand the way that they solve problems.

Josh (00:06:16) - Yeah, well, tell tell me a little bit more about what Colby is. Why that's valuable.

Jennifer (00:06:21) - Oh, I love Colby. I could talk about it for a long time.

Josh (00:06:23) - Colby people, usually. I was joking about this before we recorded Colby. People usually really love Colby.

Jennifer (00:06:29) - Yeah. So one of the things I love about Colby is it only measures strengths and the. So when I run Colby sessions with teams, we can look at each other's profiles and notice where we're similar and different.

Jennifer (00:06:42) - But none of that has anything to do with being better or worse than other people. So Colby is great at looking at, you know, what you bring to the table. And even though that's different from other people, how you can leverage those strengths and leverage those differences, Colby measures for different sort of what they call action modes, fact finder, follow through, quick start and implementer. And usually people have one of those four action modes that they initiate problem solving in. So for example, I'm a fact finder. As you could tell from my background, I love learning and I love trying new things. I love exploring new things. I collect data, I collect information. So when I'm solving a problem, I need lots of data in order to make a decision. Not everybody does that. Some people start problem solving by brainstorming. Those are the quick starts. Other people start problem solving by creating a structure or framework or a process that they want to follow. And other people start problem solving by building a model, or sketching out a solution, or thinking about a tool that they'd like to use.

Jennifer (00:07:46) - So that's just sort of one little snapshot of example about how Colby, measures our strengths.

Josh (00:07:52) - Yeah, maybe, you know, to our friend that's listening to our conversation right now, let's come up with some, some things that they might be able to do. so either maybe things that they may be able to assess in their personal professional life or, you know, again, things that they might want to look out for, that might be causing frustration or, you know, again, some sort of gap in there and, provide them some guidance or, you know, something, something that you think would be productive. It's like, you know, I wish more business leaders did this and they would probably benefit from it.

Jennifer (00:08:26) - Yeah, sure. So one of the things that I think a lot of entrepreneurs struggle with is, how to know when to delegate and how to delegate and how to let go of stuff. Yeah. one of my clients just recently brought me a question which is, around his rapid growth of his organization.

Jennifer (00:08:43) - He's going to be going through a huge hiring spree in the next few months. he's expanding outside of the community that he's been working in. So he's going to have people spread across different time zones, even different countries. And he said to me, how do I preserve the culture of my organization as I grow? And what's going to how do I know that this is going to work? You know, this is we're going to hire a lot of people in a short period of time, and he's going to need to trust and delegate through that process. He can't do everything on his own anymore. and this is where I think a coach approach really adds value. So you ask me what advice I have, my advice is to not give advice. I think a lot of leaders fall into the trap of knowing that they have a lot of experience and expertise and wanting to share that and offer that to their team. But when you tell people what to do, you access the cognitive part of their brain with and short term memory, which might be good for problem solving in that moment, but it's not good for learning.

Jennifer (00:09:42) - And in order to be comfortable delegating and letting go of stuff, you need to be confident in the people that you're delegating to and know that they have those strengths and the way that you know that is by watching them solve the problems and come up with the solutions themselves. So using a coach approach, asking questions, offering, obviously you have to teach people skills and reinforce values and offer mentorship when they're missing information. But when they have that grounding and that framework and the structure that you've provided, you need to let them loose. You need to ask them questions and let them solve the problems and then trust them to do a good job for you.

Josh (00:10:22) - Yeah. what if they've tried that? and they're like, it ended up being very, very disappointing. Like, and there was some consequences to it. Like we lost a customer. We had a really negative experience for a customer, something like that. And so it's almost like they're saying, yeah, I know, but it's like once bitten, twice shy kind of thing.

Jennifer (00:10:43) - Sure. Yeah, I think that's a good point. I think there still needs to be accountability. So I believe strongly in performance management. You need to give people feedback as they go. I it's like training wheels. I think with new leaders they have to have some room to make mistakes and fail. Failure is a normal part of life. And I think we're too scared of failure in a lot of cases. all of those moments where we make mistakes and mess up and those are learning experiences. And if you can embrace them and see them that way. and. Create an environment in your organization of what they call psychological safety, where people know that it's okay to screw up. They're going to come to you with those errors and mistakes more readily, and you're going to be able to solve those problems more quickly. Whereas if there's a fear of repercussions and a fear of, you know, being held to account in front of other people, for example, you know, that's going to stifle creativity, stifle innovation, and it's going to cause more problems than, than you need.

Josh (00:11:47) - Yeah, yeah. How do you address the issue or how do you begin to explore the issue if you have a client and they're saying, I am just I'm just burnt out.

Jennifer (00:11:58) - Yeah, that's a great question. And I've been there so I can relate. It's one of the reasons that I left our family business. I, you know, after 17 plus years, I felt like I wasn't in the best position to be leading the organization anymore. I knew that it was time for somebody fresh to come in. I wasn't excited about the future. I wasn't, you know, people were bringing me ideas, and I was. I knew there were great ideas and I didn't want to run with them. so yeah, I can relate to feeling kind of done. And the, the solution there. I think it depends. and somebody one of my mentors at the time asked me a really great question around that. She said, if you were to take a month off work, let's say pick a time, and you came back to the office after that period of that break, how do you feel? Can you imagine? Do you feel better? You refreshed? You like? Is it really just about needing a break and needing to get away from it for a while? Or do you feel the same way you did or the same way you do now? so yeah, so doing a little bit of self-reflection and examining, whether or not you're in the right place still, I think is part of the solution.

Jennifer (00:13:09) - And then, if you are still passionate and excited about what you're doing, then we can talk through ways to make sure that you get a little bit more balance in your work, that you're leveraging your strengths. So we talked about Kobe earlier. People really do get burnt out if they're not able to play to their strengths, if they're in roles where they feel like they have to conform to somebody else's expectations about how to get the job done, that's going to lead to burnout and stress. So, you know, some of it is about troubleshooting why you're in the place that you're in and working through those issues. And the rest of it is that sort of deeper soul searching, I think.

Josh (00:13:47) - Your website is Oak Bay Coaching and Consulting. Say someone that's been listening and they're they're loving it. They're like, okay, I would really love to explore potentially working together. Like what would you recommend their next steps be?

Jennifer (00:14:01) - Sure, I have a great resource that I've developed about how to preserve and protect your organization's culture while you grow rapidly.

Jennifer (00:14:11) - So if you'd like to take a look at that guide and checklist, you can go to, just go to Oak Bay It's not my regular website, but that's a link that'll get you to my resources. I also have a list there of ten tips for new leaders. So we talked earlier about delegating to new leaders. As an entrepreneur you can go and download that resource too, and it'll give you some advice about how to support new leaders in your organization. So that's a great way to kind of connect with me. Yeah.

Josh (00:14:39) - What I'm sorry, what was you shared the link pretty quickly. What was that URL?

Jennifer (00:14:43) - Oakbay coaching.

Josh (00:14:44) - Com Oakbay okay. Good, good. I was just pulling up because I had your other one. Aside from that, what do they need to click on when they do that?

Jennifer (00:14:54) - Yeah. So the link there that you're looking at is, it should bounce to a page called Free Resources.

Josh (00:15:02) - Free resource. Got it, got it, got it. Yeah.

Josh (00:15:04) - Fantastic. All right. Well Jennifer Wilson again, leadership coach Colby consultant facilitator and again, founder of Oak Bay Coaching and Consulting, your website. Okay. Coaching and consulting. Okay. Or as you said Oak Bay Jennifer, it's been a great conversation. Thank you so much for joining us.

Jennifer (00:15:25) - Thank you so much, Josh. It's been great to be here.

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