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Jenna Dillon is an executive coach working with high-performing leaders, business owners, and entrepreneurs to support their development in leadership, culture, performance, and change.She's been named a top coach by many different organizations.
Jenna, welcome to the show.
Thank you so much for having me, George.Happy to be here.
Yeah, excited to have you on.Tell us a little about your personal life, some more about your work, and why you do what you do.
Okay, well, I like to say back of the card, front of the card.So front of the card, I'm an executive coach.
How did I get into coaching gosh, several years ago, I was told when I was figuring out how to step into my second career, oh, you should hire a coach.
And I'm like, what's that days later, I happened to meet a coach on stage at an event I was signed up for my jaw hit the floor, I said, Can I buy you a cup of coffee?Pick your brain,
Mr. Coach, I don't know what you do, but someone said I should hire someone like you.And then that was the start of it.He introduced me to one of his colleagues.I hired her as my first coach.
And within, I mean, three sessions probably, George, of hiring my first coach, I was stunned that this was even a career that people did.I mean, in the best of ways stunned.
I was like, this was so similar to what I was thinking about doing, but better. So how can I do it?How can I be you first coach?And so I got formal training that way.And the rest is history.Back of the card.Gosh, I'm a Midwest girl.
I grew up in Kansas City, went to school in Chicago for seven years.I'm very, I'm a creative and an intellect.So I studied two very different tracks, which will show that I studied dance.
So that was my first career as a professional dancer for seven years in Chicago.And then I also studied business management.So very creative and analytical at the same time.Yeah.
Oh, I did professionally on stage, modern, jazz, contemporary.I also did a lot of teaching of dance.And so that was something that actually ended up being a great skill.I learned in both tracks in school is formal training and teaching.
And so it was a really wonderful way for me to learn how to incorporate some of that into even coaching now.But yes, I taught many styles and then professionally performed modern jazz and contemporary.
Nice.It's certainly it is one thing to be able to learn yourself.A discipline like dancing obviously requires a lot of physical strength and stamina, but you need to make every move the exactly correct.So that's really hard to learn how to do.
But then to actually be able to teach that to somebody else so they can put it into action is also really, really hard in a different skill set.
It is, you know, and I find so much of both of those is in the mind, right?
And it's so, it's around, it's about discipline, it's about perseverance, it's about grit and detail and being really perceptive on looking at alignment or being really perceptive in what you're noticing in other people, what they're picking up, but they're not picking up as an instructor.
You have to make sure they understand the gaps and that they fill those gaps, right? All of that is like very pertinent to be a good teacher and even to be a good coach, to be a good dancer, all of that.So absolutely.
And so you say, OK, I think I'm interested in becoming a coach and serendipity strikes and you meet somebody who is a coach and you have these sessions and it really starts clicking for you.How do you decide who it is to coach?
You know, that's a great question.I find that depending on a few factors, not just, of course, personality, but what someone who's becoming a coach, what they find that they have an interest in in terms of a niche.
I have some coaches that I know that specifically focus on nonprofit, other coaches that will focus on a specific industry because it's something they're passionate about.They want to serve those types of people.
I think another factor outside of interest in a demographic that they want to serve is how much formal training and what kind of formal training that they've gotten.
And so, you know, some people have gotten enough training or tools on their tool belt where they can really coach at executive level, which is me.
Like I ended up coaching at top leaders of organizations and being able to know even how to coach entrepreneurs, people who have
multiple businesses on their belt and the challenges that they're going to face might be very different than someone who is a leader in an organization and that's their main role.
So it really depends on, I think, a few factors, those being some of them.
Yeah.What was it that really made you go in the direction of entrepreneurs, business owners?
You know, I'm really passionate about impact.Like that's, I would say my strongest and biggest motivator and my dad is an entrepreneur.
So being able to see him have several different entities that he was passionate about exploring and understanding even I think having him around to model how his and see how his mind worked.
He would call himself and other people he knew they would have the quote unquote entrepreneur bug. Like they would just have an idea and they'd see a demand in the market or they'd see something that wasn't yet done.
I had to do that, you know, and then they'd start building a new entity.And so I think because I also had him around, you know, my whole life, whether he meant to show me that or not, it was something that was like, Oh, I feel like I kind of get.
the entrepreneur mind because I was around it, you know, and the passion behind it and the psych, like I call it a psychological profile, if you will, where often business owners, top executives and companies, leaders, they have a profile or archetype and way that they are seeing the world.
And if I can make an impact with them and help them be even more successful and optimal, oh boy, that ripple effect gets me going.
Yeah, I appreciate that.And it is interesting having a parent that is an entrepreneur.
I'm sure that he's wildly successful in lots of different areas, but you also got to see him as dad and you got to see the things that he maybe wasn't awesome with.
So it probably helped you to understand, okay, there's room for improvement within everybody or room to advance no matter how successful somebody seems to be, or I'm totally wrong.
No, I mean, I think I think it's been such a gift, honestly, to be able to grow up with a father who I believe not only showed this entrepreneur mindset, and of course, I didn't have the words as a kid for that, but also I got to see him as my dad.
Like, you know, I think there's a beautiful. progression in which a relationship to a parent can change as the child becomes an adult.
And so even today, like being able to have conversations with him and my mother around how I can not how not the conversation isn't around how I see them as an adult.
But the conversations change because we can see each other as adults versus they're not just my dad or they're not just my mom.They're actually this human.And to see another aspect of them is quite beautiful.And for them to be willing to
to comfortably have me see that and show that for me.It's a gift.
Yeah, for sure.So the people that you're working with, I imagine it's like anything else.Some people probably have worked with coaches in the past, but I would guess that the majority have not.
It's a mixture, I have to say.And I feel like, you know, in order for me to even speak to that, I'd like to call out an elephant in the industry.But I feel like when I mention it, people are like, okay, yeah, great.We're talking about that.
We're bringing that in the room and saying that it's there.And that is, there's a lot of ambiguity and gray area about this industry called coaching. You know, and I think part of that is because that term coaching is such a popular trendy term.
So then some people don't understand or don't know, hey, there's actually a difference between a coach and a consultant or
if someone's a self-proclaimed coach, they might decide, oh, I had a background in finance for 20 years and I was a leader for 20 or 30 years of my career.Now I'm gonna be a finance coach.
And it's like, wait, like that's very different than someone who's gotten formal training and calls themselves a coach the way they approach their clients.So there can be a lot of ambiguity and different archetypes in the industry, right?
So I think that that's something to really point out.
Yeah, I certainly appreciate that too.
All right, so when you're talking to people, and it could be a client or it's probably somebody who's considering taking you on as a client, for lack of a better term, what is, I don't wanna say pitch, but what is the value proposition?
Say, hey, work with me and this is the result that we will hope to find.
Sure.Yeah.So I'll actually go into a little bit about the archetypes that I find coaches that there are in the coaching industry and speak a little to how I'm different.
So on one side of the spectrum, you have an archetype that is very high in business acumen.Think of like the buttoned up suit with a pencil skirt or stilettos.
And they are great in strategy, they're great in business acumen, they know their KPIs, they know how to measure results, and often their style and approach of how they're going to work with their clients and the leaders of organizations is saying that they're, I would say, they're going to be very prescriptive or more consultative, right?
Like saying, here's what I recommend you do.They might even
They often are hired for a project base, and thus then when they're working with their clients, the individual leaders, they will help them understand what it is they need to do, like kind of follow my advice, here's what you do.
So thus then it'll build their client's followership skills, but not necessarily their leadership skills.And so then on another side of the spectrum, you have an archetype of a coach who will be very high in emotional intelligence.
They'll know how to tap into your creativity, your intuition, your ability to learn how to communicate with not just yourself between your ears, but with other people and know how to capture, like how to support somebody emotionally.
Right, all of those interpersonal interpersonal skills if you even go further down the spectrum, they'll be very like intuitive and the way they talk even and some people even will have like different modalities with like crystal and things you know and there's all different kinds of and respectfully like there is a time and a place for every type of coach like that right and often.
Those archetypes of coaches on that side of the spectrum, when they're going to be working with a high level executive or a business owner or entrepreneur, they have a hard time digesting some of that because they want to be able to translate it into tangible results.
They want the return on investment.They want to be able to understand, like, how do I measure
Being able to communicate well into a tangible result and often those archetype of coaches don't know how to translate those into results those types of things.That's where I come in.So I'm going to bring in that emotional intelligence.
interpersonal, intrapersonal skills, creativity, even having them learn how to tap into their intuition and we can translate it into results.I'll also be bringing in that business acumen and strategy level.
So I'll be a mixture of both sides of the spectrum because really with where this day and age is in the workforce, leaders have to keep reinventing themselves and their skill sets.So they actually need both. to be good, successful leaders, right?
So they just need to be able to have somebody who can translate both areas.
That makes a lot of sense.How do you, how does one learn to tap into their intuitions if it's not something they access or they access it not very often?
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So it's not a one size or one way fits all, but I will at least speak conceptually to how to do that.
So I'll actually talk first on how people are highly tapped into their logic or intellect versus their intuition, is when they are going at a fast pace.
and the stakes are high, they may not be aware of what the, they might not be identifying the emotions they're actually feeling, even if they're feeling them, because they're just going, going, going, going, going, right?
And they can easily put their nervous system in a sympathetic state.And in other words, in like a slight survival.
state where they're just going and they're pushing and they're fighting, or they could be part of the fight, flight, freeze, faint, fawn states.Like those are different ways that people will get into a certain state where they're just like burnt.
If they're in that state too long, they're burning the candle on both ends and their, their nervous system is going to get fried.
But, but every time a human is in a state of fear, which is often like we're in a state of fear when we're in those modes. we're thinking with our mind and our logic.Cause it's, it's, it's just how our brain is wired.It will go into logic.
I got to figure this out.What do I do?Like, you know, it's like the state of anxiety and undertones of fear.You go to your mind, you go to your logic and your intellect and analytical part of your brain.
So in order for us to tap into intuition, we actually need to be in a much more settled, steady state. And that has to make that in order for someone to get into that state.
That's what I mean by it's not a one way fits all because I got to be able to learn around the insides and outs of like how stuck is my client in that state. And are they able to get out of that in what settings?How did they get out of it?
What are kind of indicators or things that influence them to help them settle out of that survival state?So I'm really starting to understand when I began working with my clients, What are those indicators for them?
What are those prompts or what are the things that allow them to get into that state?When do they access that state, if at all, and how have they leveraged it, even if they didn't realize it, right?
So sometimes it's people who, if they meditate, for example, they slow down and think about one thing and tap into how their actually feeling or how their body is feeling kinesthetically.You know, there's several different ways.
Another completely different way is someone expressing themselves through art. Like I mentioned, my background is a dancer.So people can get into this zone or flow even from having this passion behind an expressive form in performing arts, right?
They're in this passionate emotive state or intuitive state rather than this creative state, rather than this analytical, logical kind of linear way of thinking.So hopefully that gives you an idea.
Yeah, I think that that makes a lot of sense.
Do you find that just for lack of a better term, we have the different archetypes, we have the driver type, a non-artistic person, and then maybe just the flip side of that coin, more of an artistic person who's not that driver.
And it makes sense to me that that the driver person buttoned up person would be more and we're just going and I need to learn how to slow down and be more still.
But is that still something that that the creative struggles with also is slowing down or is that easy for them?
You know, I love the question.It really is different for the person versus the archetype.Some creatives are great at slowing down and some it is so uncomfortable to slow down, you know.
Same with that other archetype of like someone who isn't that creative or doesn't tap into their creativity that often.I'll say it that way.They might not enjoy slowing down because that's uncomfortable.
I would say for the highly successful, high-performing individual, they often are uncomfortable with a slower pace because they're used to going fast and accomplishing quite a bit at a very high pace with high stakes.So why would you slow down?
They start to relate to this fast pace with success.If I want to be successful, I have to go fast to do it. You know, so if I slow down, I'm going to fail.That's not OK.
You know, like there's really these this myriad or or I keep saying kind of psyche profile, if you will, around different ways that they relate to pace or success or failure, or even how they place worth on themselves and what makes them valuable.
That can actually be little ways that they've whether they meant to or not, like consciously or not. trained themselves to be a certain way.
A thousand percent.Right.Like I have I have created something out of nothing.I am a successful business owner, entrepreneur, operator.
But is it what function of I mean, they're already successful, but maybe they're at an eight and you say, you know what, your your your life could be 10.
and it could be accessing just something different, not necessarily exactly what we're talking about, but maybe, but just that there could be more for you.Is that part of the conversation?
It absolutely is.Yeah.And I would say it can be part of most conversations.But, you know, I've even I even had an entrepreneur who I was working with a week ago.
We had a session and she was actually in a state where she was so burnt out, like literally burnt, had burnt the candle on both ends, was so used to going at a fast pace for most of her career.I would even argue most of her life.
But we didn't talk about that. But all that to say is she's like, I'm exhausted.I don't want to go at this fast pace anymore.And it was no longer what she was calling success. going at a fast pace was no longer something she wanted.
And so she was assuming that if she didn't go at a fast pace, then that meant she had to change her goals of what she, the results she wanted to accomplish.And that's where it could get a little fun is what if you could accomplish the same
but at a slower pace.That actually is a similar challenge to, well, there's the same time in a day, we can't change that, so you can work the same amount of hours, and instead of accomplishing your eight, you can accomplish more, right?
But then we can also change that and go, you know what?Maybe you're at a 10, but you've been going 100 miles an hour at a 10.What if you could accomplish what you were accomplishing at 100 miles an hour, but go at like a seven?
It still challenge you in different ways to be innovative, creative, make decisions differently, discern differently, make different expectations or boundaries, all of it.It's a game changer.
Yeah, I think that that's super powerful.
I love hearing stories about, I work in personal finance and you hear about financial advisors who work 80 hours a week and it's helped them to be really successful, but at the expense of family time and they make a decision, they're gonna cut their work to 50 hours a week and their business somehow explodes.
But it takes oftentimes the work of somebody coming in from outside like a coach to say, hey, you probably there's zero percent chance you're going to do this on your own because you're so nervous, scared or whatever the term is.
But this this is possible.
And actually to what you were saying, like the situation that you find or the environment that you find some of your colleagues in, you know, I would say the three top scenarios that my clients will find themselves in before they start working with me is they will be working around the clock, 60 plus hours a week.
Like I was like, oh boy, like you'll resonate with this because you recognize it and they feel trapped.
because they feel like if they were to slow down with what they're doing, it will be at the detriment of the organization, the teams they're monitoring, et cetera.And they can't do that, but they're exhausted.So it's a trap to them, right?
So that's one scenario.Another scenario is, and I've actually, you know,
it breaks my heart and also gives me motivation to like and like serve this demographic even more is when they come into and even in one session, I'll start seeing this and I'll start sharing this with me that on paper, they're a high performer.
They have a great reputation built.They are incredible.And they have actually had for most of their life, even maybe as a kid, for some of them, people were used to putting them on a pedestal and saying, oh, well, of course you did it, George.
You're George. You know that they were used to that they are used to that.And when you then talk to when I then talk to them.Everyone assumes they're great.They are satisfied.They are successful and doing great.No, they are deeply.
unsatisfied and that they feel like nobody understands them because there's a part of them that hasn't fully tapped into what they're capable of and they don't even know how they don't know what that even is and what that could entail but they feel incredibly unfulfilled.
So that's another scenario, right?And then the third scenario is when it's the entrepreneur, it's a version of an entrepreneur bug.
I'll say it that way, where they, I say that they have a little business affair with themselves and they'll start an entity, it's growing, and then it gets to a place where they don't know what to do with it.
And it's a little, getting a little chaotic and ooh, it's gonna freak them out.So you know what?I'm gonna go start another entity over here and I'm gonna feel much better starting this other entity. and then we're gonna focus on that, right?
And so they start having these quote unquote business affairs because they're gonna leave one organization or not focus as much on it as an organization and start another one because they don't know what to do about the problems that are starting to arise in one entity that they've built or one entity that they have invested time and energy in.
So those are kind of three very common scenarios of what someone might be experiencing before they work with me.
Yeah, that certainly does make sense.Just feeling trapped and exhausted.And what do you even do?And yeah, trap trap by success.Yeah, I guess one of those good problems, but but a problem nonetheless.
I love it.Well, thank you so much for coming on.Where can people learn more about you?How can they engage with you?
Yeah, so my email is one of the easiest.It's my first name jenna at jenna dillon.com.Last name is d i l l o n. My website is executive performance Institute for coaching.com.And then The third thing I'll leave is LinkedIn.
I'm on LinkedIn, so you can find me.You can message me, reach out if you have any questions.
And I'm really passionate about informing people about coaching and how to identify the right coach for you, how to know if someone's formally trained, et cetera.
So any time that I even connect with somebody, if they are remotely interested in coaching, I'll talk with them and see, if not me, who is the best fit for them and try to help acclimate and educate them on it.
That makes sense.Just like that person helped you with back in the day.
Exactly.Yes.Love it.Very good.We come full circle, George.
It all comes full circle.Well, if you enjoyed it as much as I did, show Jenna your appreciation and share today's show with a friend who also appreciates good ideas.Send Jenna an email, jenna at jennadylan.com.
And give us the website again, please, Jenna.
Executive Performance Institute for Coaching.
Excellent, .com and then find her on LinkedIn as well.I'll list all of those in the notes of the show.Thanks again, Jenna.
Until next time, remember, do your part by doing your best.
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