I'm Kaylan, leadership educator, podcaster & speaker

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Entrepreneurial Leadership 101

January 18, 2020

I have a really big confession, and if you’ve heard me talk about this story before then you know what’s coming, but I have to be 100% honest. Leadership was never something I really wanted.

Or, maybe it was but I just supressed that. And honestly, the first leadership role I was asked to step into – I accidentally took it. I didn’t know what I was getting myself into. And when I figured it all out, I was like, “oh crap.”

Entreprenurial Leadership Is Not Selfish

See, all through my life – and you might feel the same way, I’ve been embarassed by my desire to lead. I remember so many group projects where I was ostracized and called out for having too many ideas. So I shut up and learned to dread group projects.

I remember in college I signed up for a class I was actually excited for, but when I learned the curriculum was 50% a group project – I dropped it!

I withdrew because I didn’t want to do a group project. Hashtag, severe introvert. But the truth is, I labeled myself as BOSSY. People told me I was bossy, so I tuned it down and shut my ideas off.

Have you ever done that, ever felt that way? Have you ever been made to feel icky for stepping up and taking the lead?

So, take this girl who all her life felt the need to hide her leadership, hide the traits she labeled as bossy, and put her into her first true leadership role. Just imagine how that went down.

How It Went Down

I constantly worried I wasn’t cut out for it. See, I didn’t want to lead a team – but I accidentally said yes to it. So, I had just joined an online marketing agency as a temp, rose to content strategist and was then asked to become Marketing Director.

Don’t ask me why I didn’t assume being a Marketing Director would mean I’d lead a marketing TEAM. In my mind, I’d just be observing projects from afar, maybe behind a screen and never talking to anyone ever.

As it turned out, I was ushered onto the executive leadership team to help lead a team of about 30 women spanning all the US and Canada.

I didn’t know what I was doing. I didn’t know how to lead. I didn’t know what I was leading the team TOWARD. I was floundering. Every team meeting I held, I thought, “Oh, they can see right through me. They know I’m not supposed to be here.” And I wondered, “So many people had been in this company longer than me. So… why me?”

Entreprenurial Leadership Threw Me for a Loop

Why was I asked to be here and not someone else? That fear kept me from truly leading. It stemmed from a mindset I was still functioning within – the mindset of the traditional team system I had grown up within.

I felt OFF, just weird. Leadership didn’t fit or sit right with me – WHY?

The teams you will be leading will look like the team I led – and it will be different than what you’ve ever known before.

The traditional team system looks like this – authority exists VERTICALLY. Up and down. Time and your title are what garners you respect, even if you don’t earn it relationally with your peers or team mates.

So here’s what I mean by that. If you’ve been there, if you’ve been with the company the longest, the longer you’ve been there, the more time you’ve given to the company. Um, that is what rises you up to a position of leadership. If you have a title that puts you above somebody else, this meant that you were a leader in the company. So time and title are what garnered you respect. 

So this is why leadership just felt off to me at first because and I didn’t know it at the time. But I was I was, um, assessing my own position from what I knew of leadership and authority. And I thought, Who am I to be in this place of leadership when I’ve not been here the longest? And who am I to be given this title when I don’t feel like I’ve earned it by giving time to the company, you know? 

So imposter syndrome took me over and told me that I was not a leader for the 1st 6 even nine months off my tenure in this leadership role, I was so inward focused, just worrying about myself, the entire time every leadership or every team meeting I held. I was thinking about myself the whole time. And by saying in the right thing, what do these people think of me? Um, why don’t you two talk about next? Am I inspiring people? Like, the whole time? I wasn’t even truly focused on the words that I was saying. And if I was serving my team, I was worried about what they were thinking about me. That’s not servant leadership. 

Traditional & Entreprenurial Team Structures

The traditional team system looks like the authorities exist vertically. Um, the time that you’ve been within a company and the title that you had the amount of money that you make is what puts you above other people. So here’s what entrepreneurial teams look like. 

And the teams of the future authority exists horizontally. Everyone must earn their leadership by stepping into their strengths and truly owning their zone of genius. So flashback to those were projects, Um, when somebody wasn’t carrying their weight. Right? So this is why I always felt like I had to take the biggest leadership role in group and in group settings, because you always you always had those those people in the group who just all I’m in a group, so I don’t have to really work that much. And, um, I really wanted a CZ. So I knew that if I want to get in a Then I had to be the one that stepped up and made sure that I hadn’t a because I can control myself. I can’t control Johnny over here who won’t get his head all the magazine. But I just need to step up and take control. So that’s what I did. And it burned me out. And I hated group projects. Um, so yeah, but today. 

Here’s the great thing. Authority exists horizontally, and everybody can step up and be their own leader by offering and staining in their zone of genius and so you, as a boss, as a CEO, as a leader, your job is no longer toe lead from the top, but rather lead by supporting each team member to be their own leader. You are truly leading leaders. Everyone earns respect and even loses respect by their motivation, their work ethic, their collaborative skills, their service to the vision and in their belief in the purpose. And as a leader of leaders. This puts you on an even playing field with your team. Your role, just like each of your team members, has a role is to be the protector of the vision and in the ultimate purpose and the servant off the other team members. 

So your job is to be the protector of the vision and the purpose, and to serve your team members and make sure that they have the resource is they need the coaching than they need. The belief that they need your purpose is to grow each team member and pour into them and help them own their leadership while also providing the resource is that they need to do their job and to always be there to remind them off the vision in the purpose. Every chance you get that sounds amazing, right? Um, you no longer have to carry the entire weight of your company from the top. I mean the responsibility. There’s still a lot of responsibility on your shoulders, but you get to share the purpose, the vision and the workload with your team. They get to take ownership of the purpose mission, envision alongside you and help you carry the weight of that and to execute your mission in your purpose in your mission field. 

And so one of my clients put this really a beautiful way. She said that when she first started out as an entrepreneur, she knew she was taking a risk, and she knew that every step of the way she was having to to create a way forward as she was going. So she was having be really scrappy and resilient and flexible and adaptable, and she said, um, she said that it felt like at the same time she was driving the train while also having toe lay down the tracks at the same time. Um, but as we’re strategizing for hers, first hire, she said. It feels so freeing because she’s really excited to pour all of her focus into seeing the vision where they going to mapping that out in more detail than she has been able to in the past, and to focus on laying the tracks while she has help. She brings on help to help drive the train so she no longer has to do both things at the same time and go only so far on Lee so fast. Now she can go faster with a team alongside her toe, help take ownership and carry the load. 

Well, guys, that’s all I got for you guys today. I hope this inspired you, motivated you, gave you some peace around leadership and helped you to look at the way that you’ve been perceiving leadership in the past and maybe help you take ownership of your leadership capabilities and no longer feel like you have to apologize for it or hide it because your leadership is a gift to the world. 

If there’s one thing that I want you to take away from this podcast, even if you don’t listen to a single more episode  I want you to understand that your leadership, you stepping up and being a leader is a gift. And it’s a blessing to this world. And it’s a lie that you don’t deserve it or you aren’t good enough or you weren’t meant for this. That’s not true. It is a lie. You are here. You have started a business. If you’ve made $1 imagine what that means. You created an opportunity for yourself out of nothing. Not everybody can do that. 

We all have different strengths. Your strength as a leader is creating opportunity, and you’ve done it for yourself. And you have the responsibility to do that for other people. And the longer you hide that you hide from that or you use stuff that in a closet and you apologize for this desire to lead you, hide it, you you blame it or doubt it. The longer that happens, the longer more people have to wait to step into the opportunity that you’ll create for them. 

If there’s one thing I could inspire you to do is to realize that this gift of leadership is also responsibility that you have to rise up to and take ownership of no longer apologize for it. But give it freely as a gift to the world. 

If you approach it with that in that way, man, you’ll never feel guilty about it ever again. And you’ll feel excited. And the people you lead will be excited to walk alongside you. 

I'm Kaylan, leadership educator, podcaster & speaker

What are you searching for?

Reading suggestions

Crafting a 90-Day Onboarding Plan

Job Postings that Attract Top Talent

Mapping Your Leadership Style