How leading a startup totally changed my management style

I look at my own career in two phases...1) The micromanager and 2) The macromanager.

Both have served me well. Both led me to enormous personal growth. Only one, however, resulted in my personal happiness and a less stressful environment.

Phase 1: Without a college degree I set out to find myself a career and settled on Public Relations. It seemed like a good fit. I loved news. I enjoyed writing. I have always liked people. So I started out by building a PR firm that eventually grew into a top 50 firm. Where we good? Yes. I definitely had good people working for me, but I honestly never felt that we were great! What fueled us was my relentless, supercharged, obsessive and unbreakable desire to succeed. I was paranoid, secretive, and looking back now, I am certain that I was pretty much an asshole!

But this approach served me well. I remember reading a famous business book by the CEO of Intel, “Only The Paranoid Survive”, and it really seemed to validate me as a CEO. I was a control freak, micromanager to the extreme and so obsessive about every particular detail related to our entire business! I literally drove myself crazy. (And I bet everyone that worked for me, as well) But then again, everyone I knew that was running a company operated the same way so I thought I WAS THE NORMAL ONE :)

After having moved on from my PR firm, I decided to restart my career in a new sector, on the digital media side. I felt like it was time to reinvent my career… and myself. Entering the tech sector was culture shock! Not having a dress code (finally!) was the easy part. Adapting to the way people managed and behaved was the hard part.

What surprised me so much about working in tech was how genuinely nice everyone was. How they would share anything and everything. Total win-win. And totally the opposite of how I spent the first part of my career. And the other profound observation was how truly autonomous everyone was that worked in the field. In both large and small startups, I would find people switching roles all the time. They had loosely defined job definitions and the ability for anyone to contribute to anything at anytime. Crazy!

The realization that the tech world operated completely different from the overall business “corporate” world took a while for me to adjust to. My old habits of micromanaging every single bit of minutia, even the stuff I was clueless about, probably helped our young startup get out of the gate and gain traction but it made me crazy and stressed at the same time. And additionally, I was hiring people who fit into my micromanagement style as well. Deja vu all over again!

I finally saw the light though through sheer surrender and truly started to let go. And that's when things really started to change. Our culture improved. Our product and workflow got better. And personally, I was so much happier.

So, what I learned about running a startup has profoundly changed my view on management. Here’s how:

1. Hire smarter and think culture first. In the past, I would hire based on the best resume. Almost always looking at what was on paper and not what was in the person's heart. Now, I barely look at the resume. Instead, I look at the person and who they are, not just where they have been.

2. Create a vision for the team… and let them rip it apart. I used to be the guy who drove the bus, filled it up with gas and held on to the directions. Often times we would go in circles as a result. Now, I have a long view of where I think we should be heading, but I defer to the team to decide if it’s the right course and then how best to navigate.

3. I don’t measure progress the same way. I realized that while there are so many ways to measure progress based on financials, results, etc… they are often not the best ways to ensure you are heading in the right direction. Now I rely more on the feedback of our team, whom I trust to really be objective about their own sense of progress.

4. People can contribute anywhere, anytime and calendars mean shit! I remember being obsessed with controlling when people arrived at work, when and how long they took lunch and their vacation schedule. At our startup, I have no policy with regards to any of this. And I realized, motivated people that are passionate about their work don’t fuck off and can work anywhere, anytime. Good work is good work!

5. Sharing is caring! Yup, I worked the longest and sacrificed the most in my previous career in PR. And as a result, in my warped mind, I deserved all of the gold! Wrong. I was paid handsomely, but I paid the ultimate price. I had no one to confide in, no one to trust and no one had my back. It was a lonely and selfish existence. Now, my goal is to make all of my “team mates” rich and share in all of the rewards. It just feels so much more rewarding as a result. Win-win!

I am not sure that working for tech is for everyone and I know so many CEO’s that do a great job building successful organizations based on a lot of different management styles. As an entrepreneur, though, I do think we see the world differently. Having been on both sides of the management spectrum, for my sanity, health and the ultimate well being of my company, I would choose the tech style of management every time!