Because Training Unleashed Podcasts are all about training, you might be wondering why our host Evan Hackel recently recorded an episode with one of America’s top executive coaches, Jenna Dillon.
After you have listened to only a few minutes of the conversation between Jenna and Evan, you will quickly discover why Evan invited her to be a featured guest. The reason is that Jenna really believes in training the executives in your organization to master the skills of being top coaches. It’s a big idea, and one that can transform the level of success at every level.
Jenna is CEO & Founder, Lead Trainer, and an Executive Coach with the Executive Performance Institute for Coaching. We encourage you to spend a transformational half hour listening to this episode of Training Unleashed.
Until you do, we know you will learn a lot about executive coaching by reading the following edited excerpts of Evan’s interview with Jenna.
Evan Hackel: Our guest today is Jenna Dillon, a top executive coach who is with the Executive Performance Institute for Coaching. Jenna is an absolute expert on the impact and power of executive coaching. She offers a training program for you and the people in your company who want to be executive coaches. When they learn those skills, they will bring their value back into your organization.
We will discuss that in a second. But first let me ask, Jenna, why should companies care about executive coaching? Why should they hire people to do it?
Jenna Dillon: Thank you for asking that. I would point to the metaphor that says that a surgeon can’t do surgery on cells. He or she works on larger structures.
Evan: But the effects of that surgery are felt on the cellular level?
Jenna: Right. Executive coaches see what’s happening in an organization that the people who work in that organization often cannot see. Whether it’s a systematic issue, whether it’s a communication problem, whether it’s a leadership issue, whether it’s a problem around productivity and teams or results they want to accomplish, they need a new set of eyes.
Evan: Can you give us a case study of a company you have worked with? You don’t need to name the company. How did the coaching go, and what were the results?
Jenna: I’m happy to share. I work with a number of different industries, but the company that comes to mind first, and that I’ll share with you, is a company in the entertainment industry.
Probably six months before the pandemic hit, I started working with two of their leaders, an executive producer and the CEO, and that led me to working with the organization in a number of different capacities. But predominantly I was brought in first to just give some leadership training and communication techniques to the leaders of the company. And as you know, when the pandemic hit, a lot of industries had a rollercoaster ride and stress, to say the least, and especially the entertainment industry.
But what was so exciting, actually, and not just for me, but for them to experience, is from the time that March 2020 hit, that company began to grow and has grown 200% since then.
Evan: Wow.
Jenna: They have hired probably more than 80 employees since then. They have been able to generate more revenue than they ever had. And so they’ve been clearly learning how to do something right and be bulletproof in the economy.
Evan: Did you do executive coaching with the leaders individually, or was it more group leadership coaching?
Jenna: I have done executive coaching with both their leaders, one on one. I have done strategy sessions with them. I have done retreats with their management teams. When I say I have done this, I mean my company has done it.
Evan: Were those executives happy to have you work with them, or were they resistant?
Jenna: Oh, it was thrilling, actually. When we first started working together, we didn’t know a lot about each other and we didn’t know how we were going to work together. So there’s a little bit of the unknown . . . how are we going to partner and work together? That becomes quite thrilling. And the more that I’ve continued to work with one particular leader from this company, the more we have built such a wonderful, intimate working relationship. A lot of trust has been built and we get to be creative and very intellectual at the same time. It’s of like a right-and left-brain-minded partnership, if you will.
Evan: So I really love your answer. At one point I was running a $5 billion business. I saw that one obstacle was that people thought they were given coaches because they were not doing a good job! They thought they needed to be fixed, that they were broken. And my experience has been exactly the opposite, that when you provide somebody with a coach, they’re actually thrilled, happy and appreciative because a company is investing in them. And it gives them a way to have meaningful conversations with somebody who’s purely there to help them, with no ulterior motive. And that makes such a really powerful, powerful relationship.
Jenna: Absolutely. Absolutely. A coach is not necessarily there to fix a problem that you’re experiencing right in that moment. It’s more like saying, “Hey, where is your Jiminy Cricket that’s resting on your shoulder.” We’re not just here to come and help with a pain or a challenge that you’re experiencing. We’re here to help you have a little bit more freedom and fun in your life too.
Evan: Can you explain to me how the coaching relationship works. If you are coaching me, what are your expectations for me? What should my expectations be for you?
Jenna: Okay, great. We don’t know each other a whole lot, so we’re going to get to know each other through a multitude of different conversations that I imagine you aren’t used to having. And the more that I do this in my coaching work, the more I find how rare it is that people have conversations like this.
I’ll want you to know you can share as little or as much as you want, for the purposes of it bringing you value. Anything we talk about will be confidential. And to give a little flavor to it, we’re going to get creative in the process. We’re going to partner, not me advise you, but we’re going to partner where I’m going to try to figure out how Evan’s brain is working for him or against him. And not only should I be able to understand that, but I also want you to be able to see and understand that too, so we can think together and coach you together.
Evan: Well, that’s cool. So how do we actually do that?
Jenna: The answer is there’s no linear answer and there’s no one answer, right? Just as there are a ton of different ice cream flavors, there are a ton of different personality types, there are a ton of different organizations. Different things are going on in the economy or their industry that is impacting the company. And thus, I’ll give you two different personality tests.
Evan: I love that, by the way. My number one strength is ideation. And I also like to joke that my number one weakness is ideation, because I have so many ideas. Some of them are bad and it can be as distracting as all getout.
Jenna: We will develop a portfolio, if you will, of your personality. What are some of your strengths? What are some of the things that you’re motivated by? And I say we will look at them together because I want you to understand yourself in this way. Then we’ll start talking about some of the challenges you’re experiencing. What are the goals and initiatives that you’re wanting to accomplish as a leader in your organization?
We’ll get very, very clear on results you want to have from coaching. And then we at least have what we will call our runway set. So really how we start working together is we get our runway set so that then we can focus on vision, the goals you want to accomplish, we can look at the intention that you have, having a very intentional, clear mindset, a very intentional and clear strategy that we come up with together.
So we’re monitoring, we’re tracking what’s going on in the process, what’s working, what’s not right.
Evan: I’m new to this kind of coaching, but I get a feeling that instead of telling me anything, you’re going to say, “Tell me more.” Why does that matter? Should I expect that, or should I expect actual advice?
Jenna: That’s a great question. So most of the time that I’m working with my clients, I will check in with them if I’m getting the impression that they are wanting me to play consultant, which is what I would call giving advice or prescribing or giving suggestions. I’ll ask them, “Is this you wanting me to give you advice or play consultant versus coach?”
As a coach, I want to focus on building our client’s leadership skills. And if I were to prescribe or give advice, then that would actually impact your ability to follow what I say. Right, and build your skills.
Evan: So consultant versus coach?
Jenna: Now, in an ideal, perfect world, do I think there’s a place for each one? Absolutely. I check in and they are asking for that advice, I’ll give it. However, before I take that bait, I want to be sure that me giving advice is going to serve them best. I will slow way down. I’ll ask if that’s what they’re asking, and then I’ll say if I give you advice, assuming I have credibility and believability in that area, is that going to help you most? Because if it is, great. But if it’s going to help you most to have me coach you to help you find that solution yourself, we then will do that. So I put them in the hot seat, if you will. I have them slow down and get there.
Evan: Can you talk about the power of evoking and self-discovery?
Jenna: Oh, my gosh. Sure. I’ll actually give a metaphor around children.
Why are adults so fascinated with children? It’s because it’s really fun to see them learn. It’s really fun to see how they develop. Right? And they’re enjoying that at a young age. It’s like everything’s new. And there’s all this wonderment.
It’s the same way for adults, and I say this in the best way, we’re all just kids still at heart. We’re all little boys or girls. And so if we can, the coach and the client together can create a mindset where they seek out discovering more. They don’t just value discovering, they seek it and they’re curious about it. Then they’ll learn to enjoy it. They’ll change their association and desire to learn and take that initiative or to generate some problem-solving on their own. And that’s the sweet spot. Ultimately, that’s why I do what I do. Isn’t that one of the main purposes of life, right?
Evan: Excellent. And as you know, I always end my shows by asking, “if you had one tip to share, what would that be?”
Jenna: I so love that you do that. My tip would be to live in the questions without getting to the answer too quickly. So it’s important to live in the questions because then the answers can continue to evolve. And you set yourself up to not have blind spots. You set yourself up for growing.
Learn More!
Be sure to listen to the entire Training Unleashed Podcast conversation between Evan Hackel and Jenna Dillon.
A Special Offer from Jenna
Because Jenna is interested in having you experience coaching, she and her team conduct a monthly raffle. The reward, if you win, is a series of three different executive coaching sessions with her and members of her team.
To enter, send Jenna a message via her LinkedIn page. Simply say you are interested in taking part in her raffle. You will then be entered to win those Executive Performance Institute coaching sessions.
About Our Guest
Jenna is CEO & Founder, Lead Trainer, and an Executive Coach with the Executive Performance Institute for Coaching.
Jenna has established herself as a top executive performance coach committed to working with high performing individuals and companies who are up to exploring what they’re capable of achieving within their lives, careers, company culture and leadership. =
Jenna has been trained in several professional development programs in phenomenology, ontological coaching via transformational coaching, neuroscience/neuroplasticity, psychology and sociology. Mentoring different types of business owners for several years, Jenna partners with her clients to uncover the values, beliefs or rules that, up until now, have controlled the way they think and run their life. She creates an environment where authenticity, vulnerability, and empowerment live in accordance with each other.
Her list of clients includes entrepreneurs, c-suite executives, engineers, business owners, artists, doctors, physiotherapists, non-profit organizations, financial advisors, mortgage bankers, and other high performing individuals. A few of the companies and/or company leaders she’s partnered with include The Allbright, DreamWorks Universal Studios, Northwestern Mutual, NASA, and First American.
Although Jenna resides in the Los Angeles area, she has worked with clients around the US, the UK, Australia and Canada. Jenna is committed and passionate about empowering her clients, standing with them and for them, so they have the tools to break through barriers and create exponential, extraordinary results.
