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Building the Dream Team

Growing up, I always knew I would be an entrepreneur one day, and that I’d have to hire excellent people. And I was always been insecure about it.

Would the best people want to work with me? Would ANYONE want to work with me? Would anyone accept me as their “boss”? Would I be able to earn their loyalty? Would I be able to truly sell them on my vision? What if they leave me? What if I have to fire someone? Would they be my friends, or would I have to be detached in order to maintain respect?

My first attempt at building and managing a team was in college, for projects. I terrible at it. I lacked people skills and had a fragile ego. My peers didn’t believe in me as a leader.

Then I tried to practice this skill at different hackathons and presentations. I slowly got more successful at it. We won some prizes – but at the cost of me being an asshole. I was a bit too relentless. “Victory at any cost, even if it takes my blood on the wall.” I pushed my teammates, and by the time it was over, many of them didn’t like me.

What I’ve learned is that a leader should be humble, but still exude confidence and certainty. Thinking is hard, so we’re all inclined to want someone else to do it for us. People are begging to be led, begging to be heard. But they don’t want to be led into battle by a captain who’s afraid they’re all going to die.

The best leadership lessons I’ve learned came from military books. Clausewitz says that the psychology of the commander – whatever is going on inside the leader’s brain – is the single biggest factor that decides the outcome of a war. To be a great leader of others, you have to first learn to lead yourself.

I’ve also realized that I have an eye for good people. I’m quite good at finding overlooked talent. But I’ve earned this with many battle scars. I’ve hired people, and then had to let them go. Although I’m proud that I always did it right by them. From the evidence I’ve seen (based on my interactions on social media) not a single person I’ve ever let go from my company seemed to bear ill-will towards me afterwards. They agreed it was the right thing to do for both parties.

Here’s the other lesson I’ve learned from having to fire people: You can’t motivate employees. I’d extend this by saying that you should never give someone a “motivational speech.” It’s a waste of time for both of you.

There are some tactics you can use, such as peer pressure, or putting them in the right environment, or using plain-old incentives. But the fundamental truth is that the right employees motivate themselves. You only have to prevent them from getting demotivated.

But what I really wanted to talk about is sourcing candidates.

I like to stay in touch with all kinds of impressive people I come across. I usually try to book a Zoom call with them, and tell them I’d like to work with them someday. It doesn’t matter what stage they’re at – I believe it’s our responsibility as leaders to invest in the up-and-comers, even if it’s a word of encouragement or advice, or plain willingness to hear what they’re about.

Not only could it give someone a little dose of self-esteem (which we have a dearth of in the world today), but it’s also good for business. As these talented people grow in their lives and careers, who knows someday your paths cross again and it leads to a breakthrough in your own career.

So – if you meet an impressive waitress at a restaurant, or a cold caller who does a good job opening the conversation, or a customer support rep who shows good patience, or even a receptionist who greets the phone with just the right amount of energy and positive tonality – give them your business card. Tell them you were impressed with them, and invite them to get in touch with you if they’re ever looking for new opportunities.

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