Lessons Learned From A Young Leader and Founder

December 23, 2017
written by Daniel Coyle  AngelList | LinkedIn | Email | Twitter

With a decade of hindsight since my first role as a leader at a very successful startup, I've been thinking a lot lately about the mistakes I made and challenges I faced.

The points below are specific to my experience, but hopefully have broad applications. In an effort to keep this from becoming ten thousand words, I've tried to simplify my points and certain details. As always, if you want to discuss your company or specific situation in greater detail, feel free to email me directly.

Don't get cocky
At twenty-five, I was in charge of overseeing the development and launch (from an empty building of concrete slabs) of the largest upscale fitness club in the Chicago area. Not only ordering equipment, drawing and revising floor plans, but hiring hundreds of people that I would oversee.

Looking back, I think my ego grew as a result of a couple of things. First of all, I had been given a lot of power and assumed that that must be because I was the smartest, hardest working, most agile and creative person at the company. Of course, that's an absurd assumption, and in the subsequent years I've found myself over-correcting to the point of unnecessary self-doubt and over-analysis (more on this in a future post).

Second, I had little-to-no training. I was the only one at the new location with experience at the company. I had been a keynote speaker at the national IHRSA conference a year prior and gained a lot of recognition, but I was always aware that I was piecing things together as I went along. My self-importance was certainly a reaction to the deep awareness of my lack of experience, mixed with a strong desire for success and recognition.

Let your coworkers and employees do what they do best (read, better than you)
I saw my leadership role purely as a top down relationship. Over time I've learned and experienced, time and time again, that just because I'm someone's boss, doesn't mean I'm better than they are at anything. Businesses and startups are immensely challenging. As a leader, discover what your employees are great at and do whatever you can to make it exceedingly easy for them to execute flawlessly.

Have hard conversations as often as they're needed and always sooner than later
I was the master at avoiding difficult conversations. My aforementioned arrogance didn't lead to any healthy, productive, difficult conversations. Over the years I've learned that issues become big because they're allowed to (almost always), not because they started off that way. Being upfront and transparent, as soon as you see an issue arising, will benefit your company, your employees, and your culture.

There are paragraphs and paragraphs of additional points I could list; things that I was utterly abysmal at and what I'd do differently today. What I've chosen to write about are the few things that stand out as having had the greatest negative impact during my first foray into a leadership position.

Thankfully I've had time and opportunity to grow and improve and I'll be forever grateful to everyone who has contributed to helping me get to where I am today. I'm incredibly thankful. Thanks for reading, email me if there's something I might be able to help you with.