Your first job leading people

At 23 years old, I got my first job leading and managing people. I'd been at the company as a sales rep for almost three years, and (as I'd seen it) earned the right to be in responsible for the entire sales team.

I was too naive to be scared. Just arrogant.

The night before I started work, I got a note from the company's CEO:

Tomorrow, Monday, your life is going to change more than you even realize.

Up until now, whatever laziness, ineptitude or lack of success with which you’ve ever been met has affected a small universe. The consequences of such a lack of success were minimal at best. As of tomorrow, your willingness to do whatever it takes to drive success is all that will matter. If you fail, the reach — and the consequences — of such failure will be devastating not only to you, but to many others.

That’s why failure is not an option.

It struck me for the first time that this was about more than my own professional advancement. I was about to inherit a disproportionate level of influence over the lives of the people that worked for me. I was also about to be responsible for delivering value to our investors, and keeping everyone else in the company on payroll. Shit. 

I thought of the tenets to which I subscribed to guide me through challenging times when I was just a kid with a lot of responsibility and
authority. Here’s what I came up with:

— Just when you think you’ve got something perfect, check it one more time. Then, fix what you STILL fucked up. Then, check it again. Don’t EVER let a stupid mistake be caught by somebody else. It makes YOU look stupid at worst, and careless at best. Either way, a leader
doesn’t need his team thinking either.

— Ask for opinions even when you don’t give a shit about opinions. Sometimes the people you lead feel good about themselves just being given the opportunity to share their thoughts.

— When you have the option, let people fail on their own. Usually, if you set the criteria, unsuccessful people are pretty good at being unsuccessful all by themselves. They won’t need your help to fail.

— Don’t dilly dally. The only thing worse than making a bad decision is making no decision at all.

— When you make a bad decision. Don’t waste time in recognizing it, announcing it, changing it and publicly applauding and rewarding the person who corrected you. They just fucking spared you of the consequences of a bad decision, for Christ’s sake!

— If all else seems equal, err on the side of compassion.

— Don’t ask anybody to do anything you wouldn’t do. And when they say “no,” do it yourself... And do it right in front of them.

— Recognize quickly what you don’t know, and enlist the support of people you trust to help you in those areas.

— And, most importantly, remember this: Know every morning when you wake up that somebody is going to try to discredit you for no reason other than you’re lack of experience and your age. The ONLY way to overcome that is to do your best to be the best, and to not give anybody ANYTHING credible or tangible with which they may discredit you. Because of your age, because of your lack of experience, you will have to live to a higher standard than anybody else. Live to that standard. Make no excuses.

No surprise: I was exactly as terrible a manager you'd expect for a 23 year old salesman. We turned over 31 people in my first two years on the job. 31! In a department of 10! 

I let more than my team down. Thanks in part to a bunch of bankers in New York and a small financial crisis, we stalled in 2008 and 2009. The company barely stayed open. We laid people off. I had my car repossessed and defaulted on all my credit cards. That same CEO who wrote me this e-mail would clean out his change tray so we could share Dollar Menu lunches at McDonald's. 

It was miserable. 

But every day, I was learning. I got a little better at recruiting and training. I got a lot better at managing people and making them feel valued. I became a little less arrogant and slightly more tolerable. And it finally paid off.

Once a week or so, I read the note I got before my first day. And even now, when I'm embarking on a new business adventure, I read it over. It reminds me how foolish I was, and how much I've learned. It admonishes me that I still have so much more to learn, too. 

And it reminds me of the most important lesson you can learn as a manager: when you find someone you truly believe in, invest the resources you need to so they might develop. Good people take patience and time to grow, but they are more rewarding personally and financially than any other aspect of the business. 

I am putting you in this position for a number of reasons. I trust you. I have faith in you. But I also am putting you in
this position because I do believe you will be successful and I do believe you merit this responsibility. Take this responsibility seriously. Let others know you take it seriously. And let others know you expect them to be serious in their support of these responsibilities.

Tomorrow is a big day for you, but remember it’s a big day for
the company, too. Don’t let the company down.

Don’t let me down.