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For as long as I can remember, leadership was the expectation. If you wanted to move up in the world, you had to be a leader: in school, at work, in your extracurriculars. Leadership was the golden ticket, and the more opportunities you took, the closer you’d get to owning the whole chocolate factory.
From a young age, I had my eye out for those golden tickets. Whenever there was a leadership opportunity at school or in my extracurriculars, I would jump at it. As I grew older, work was no different. Anytime I saw an opportunity to show that I was leadership material, I would tackle it.
The first attempt
You can imagine how I felt when we hired the very first person on my team. I was the real leader of a real living, breathing, human being. I was thrilled. I’d been fortunate enough to work with some amazing leaders in my career, and I was ready to pull out the playbook they used with me. Challenge after challenge, open door after open door, sprinkled with some tough love…I was set. I was going to turn her into a superstar.
I honestly am cackling writing this—it sounds just as ridiculous as it was. My audacity astounds me.
Things started off strong: she was picking things up really quickly, and I was impressed with what she was delivering. It was working—she would be a leader in no time. Every week, I’d push her just a little bit more. I sprinkled in the tough love. I showed her the world of possibilities that could be hers if she just kept pushing.
Pretty soon, she started to shut down. I couldn’t believe it. What was wrong with her? Is she lazy? Does she not care? Her performance started to decline, and things weren’t looking good. She’s just not meant for a startup, I thought. It’s not for everyone, after all.
A few weeks later, she quit.
I wasn’t surprised. She had become more and more disengaged, and I saw it coming from a mile away. But then my frustration turned inward—I was defeated, and I felt like a failure. I failed her. I failed the company. I went back to the drawing board to figure out where I went wrong. Why wasn’t “Izzy’s Formula for Fantastic Leaders” working?
The second attempt
We added some new people to my team a couple months later. I had a second chance. I was bound and determined that it would work this time. I softened my tough-love approach and set better expectations.
It was going better, but I could still sense the uneasy feeling, the frustration. It wasn’t until I was having a conversation with one gal on my team that I actually realized what the issue was. I was talking about how she’d been doing an amazing job and how we could see her becoming a manager in no time. She sat back in her chair, looked at me, and said, “I don’t know about that.”
I understood what I needed to do now. I had to make her want to become a leader and help her realize how good she’d be at it. Right?
She was an incredible employee, with an outstanding work ethic and interpersonal skills. We all talked about it. If only she could see it for herself. So I kept persisting, and she kept pushing back.
It was in another conversation where I was really hyping her up and talking about her potential that I actually got it. In a sigh of frustration, she threw her hands up and said it:
“I don’t want to be a leader.”
I looked at her like I was solving a quadratic formula in my head. It just didn’t compute for me. It was like she’d told me that 2+2=5 or that Pepsi was better than Coke.
This ate at me for weeks. It just didn’t make sense. But as I took a step back and started actually trying to figure this out (instead of letting my pride get in the way), it clicked for me. I had it all wrong. Leadership wasn’t this club you get invited to for being exceptional. Leadership was a career path, just like any other career path. And just like other leaders helped me achieve my desired journey along this path, I also needed to help those on my team achieve theirs—whatever that looked like.
Here are a few lessons I learned along the way and some tips you can apply to your own experiences.
Leadership shouldn’t be the expectation
I was really wrong about this part all along. Leadership might have been my own internal expectation, but it certainly isn’t that of everyone else. And just because someone doesn’t fit the mold you’ve created, it doesn’t mean they’re going to be any less successful.
I now know that success looks different for each person—as does fulfillment. We put so much weight and focus on the need to grow into a leader that we’re failing to see that individual contributors often lack a unique plan to help them forge their path to success.
What ended up working for me was to regularly meet with the people on my team and discuss what they were looking for in their growth. More established companies would ideally have systems in place for this (growth plans, regular check-ins, and all that). But at a startup—where things move very quickly—you need to be up-to-date on what your team’s goals and aspirations are. That way, as those opportunities and needs pop up, you know who can fill them.
Identify your individual contributors early
I still beat myself up that I didn’t figure this out sooner. You need to identify who your leaders are and who your individual contributors are early on in the process. Failing to do this is going to create a lot of frustration for you and your team. Sit down with them and ask what they enjoy, what gets them excited for work, and—this is important—what they aren’t interested in.
There are also quite a few different personality assessments you can have your team take, like the DISC profile, which helps them (and you) home in on their strengths and weaknesses. I strongly encourage you to invest in an assessment like this—you’ll be surprised at how much it teaches you about those on your team and how it paints a clearer picture of their motivators, so you can match their strengths to their organizational roles.
Give them opportunities to grow laterally
Surprisingly, up isn’t the only way one might want to go. There are a million opportunities left, right, and center.
An individual contributor doesn’t need to be stagnant in a cycle of repetitive tasks. Give them the opportunity to manage projects from start to finish. Or, if managing projects doesn’t spark their interest, you can still change up their work: expose them to different areas of the business where they can contribute, while also expanding their knowledge and skillset.
And, of course, recognize their efforts. As they manage more projects and take on more responsibility, the pay and title should reflect that. Growth isn’t only about leading people—it’s about responsibilities, skills, pay, and title. Make sure you acknowledge that.
Give them a seat at the table
Take a look around the room at your for you in future meeting. How many people are leaders and how many are individual contributors? Making sure your individual contributors are heard and seen is vital. Leaders are great for seeing the big picture and creating a strategy, while your individual contributors are great at understanding the mechanics and nuances within the strategy.
I’ve always been a big fan of weekly team meetings that allow everyone to be involved in decision-making. This goes beyond the typical weekly meeting where everyone goes around and talks about what they’re working on. The type of meeting I’m talking about has action items that need to be discussed and decided upon—by everyone.
One of my favorite meetings was at a past startup, where we would meet to discuss and create the company roadmap each quarter. We’d decide which new features we needed to implement into the product, when our website redesign would happen, and so on. These meetings involved everyone, and everyone had a voice and gave input. It didn’t matter if you were a leader who’d been at the company for five years or an individual contributor who just started the day before. Everyone had a voice because these decisions would impact everyone.
If having everyone at your company in a decision-making meeting isn’t feasible, you can still make sure that there’s a good balance between individual contributors and leaders at these types of meetings—it will minimize friction and improve overall communication.
Provide them with development opportunities
Your individual contributors are great at what they do, and they want to continue to improve on their skills. Giving them opportunities to develop those skills or learn new ones will not only help them do their job better, but will also help them feel more invested in what they’re working on.
I used to work for a company that would provide every employee with some amount of money each year to use toward their professional development. Everyone got to choose what they wanted to do and what area of their skills they wanted to develop. In turn, the company saw a much higher rate of employee engagement and less turnover.
It’s clear that I’ve made mistakes in my personal leadership journey. I know I will continue to make mistakes because that’s life, and I’m honestly someone who learns the hard way.
But one of the most important lessons I’ve learned—and one I teach my clients—is that you need to understand the people you work with. You need to understand who each individual is, what they need from you, and how you can help them succeed. Sometimes that’s cultivating an up-and-coming leader; other times it’s helping grow a strong independent contributor.
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