Letting go to grow — Lessons learned on the path to becoming a better leader

Being a founder is easy, becoming a president is hard. If you’ve already got this figured out, this post probably isn’t for you.

Holy moly, 2014 was a lot of fun. I’ve seen a bunch of posts about hitting the reset button in 2015 and trying to forget about what was a difficult year. Twenty-fourteen was pretty alright in my books. In fact, I’d say it was my best year ever at Dynamo.

As we kick off 2015, I thought I’d reflect on what made last year so special for me. If I were to sum it up in one word, that word would be transformation. My role in the company transformed, our process transformed and so did our team. The transformation was entirely on purpose, starting with this blog post where I laid out my plan for to work more on and less in<Dynamo. I had high hopes for being able to pull this off and for the positive change that sticking to the plan could bring about.

It’s been roughly ten months since dropping the title of Technical Director. Since doing so, I’ve been operating as Dynamo’s CEO. We’re still not sure if we’re a “C” level-type company or not, but I liked the notion, it helped to keep me on track. A title change is easy to make — edit your signature and order some new cards. Changing the way that I worked and what I needed to work on, was much harder.

Here are some lessons I learned along the way:

1. Hire someone to replace you, all of you, even if that means hiring more than one person

Letting go is really effin’ hard, there I said it. Until this year, Dynamo had been slow to hire, especially at the engineering level (we’d been a 10–15 person company for some time). Like many entrepreneurs, I subscribed to the theory that I was somehow irreplaceable. It’s a romantic notion that I used to justify the long days and weeks to myself and those around me. How could I hire someone that could talk to clients the way I do, someone that writes code like I do or that is as fast at solving tough problems? This is bullshit and I can’t believe I held myself back for so long believing it. Something that now seems so obvious was just so tough to figure out.

Stepping back (I limit myself to roughly 10 hours of engineering per week) forced us to hire and has resulted in us launching and creating more than ever before. While I don’t get to write as much code as I used to, I’m becoming increasingly comfortable (and proficient) in my revised role. Most importantly though, the team at Dynamo is flourishing. They have more overall project ownership and that really shines through in everything that we do.

With a better distribution of ownership and responsibility, I’m no longer a massive bottleneck. I’m coaching and mentoring and it feels great. I’ll still cherry-pick a feature here and there to stay connected, and I’ll fix bugs when it’s my turn. But I’m no longer shackled to my phone or computer. I can disconnect. I’m more and more at ease with this.

Hiring engineers was only part of the equation though. We also hired someone whose role was to help grow the business: a Director of Client Relationships, a position we previously thought was impossible to hire for. It’s been a year since John joined our team and my only regret is that we didn’t have the smarts to do this years ago.

2. Learn to delegate and to trust

Hiring replacement(s) for myself was a great start, but I needed to start delegating everything to those new hires (and then be able to do it all over again). Successful delegation requires trust. The person you’re delegating to will be 100x more effective if they feel trusted. I don’t know about you, but trusting someone else with the high-value responsibilities that perpetuate the company I worked so hard to build doesn&#8217;t exactly come naturally. Someone once told me that I should “fake it until I make it”. I used this simple idea to great effect at the beginning. If trust is holding you back from delegating, repeat this to yourself 10 times each morning and delegate the shit out of your to-do list. After all, if you can’t trust your team to replace you, you’re building a prison, not a business.

3. Set people up for success

Delegation is hard work. I always found myself taking the easy route (i.e. not delegating), allowing my todo list to grow without limits. There’s no shortcut or hack that makes this an easier problem to solve. What worked for me was carving out the amount of time to hand something off the right way and, most importantly, to review and critique along the way.

Resisting the urge to micro-manage, I found myself trusting more and more. I replaced nagging with coaching and mentoring, a skill I’m still honing. One of the ways I’ve exercised this is to document everything that I do or that I need to have done, leaving latitude for interpretation along the way. I don’t ever want to tell someone exactly how to do their job and finding that right balance how much background or information needed has been a struggle (I’ve been accused of being a bottleneck for this sort of thing and I’m erring on the side of over-specifying). This sort of a manifest is easily iterated upon and provides a framework for a retrospective. The more often I do this, the more often I can hand off a task for good — only to look back on it a few weeks later to find it’s being done better than I ever did it before.

Working on Dynamo is real work. This is a mantra that I repeated to myself whenever I found myself struggling, or falling back to bad habits. It’s a simple idea, but it’s had such an important effect. I’m really proud of the transformation and I’m ready to tackle a whole new set of challenges as I settle in my new role. First up on that list, finding Dynamo a much bigger place to call home. Twenty-fifteen is shaping up to be a hell of a year.

Find more posts related to design, web and the creative lifestyle at theDynamo Blog.

Written by

Co-Founder and CEO @ Dynamo

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