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Entrepreneur Office Hours - Issue #150
Picking a fight I'll probably lose
Since I teach entrepreneurship, I spend lots of time thinking about the best ways to… well… teach entrepreneurship. To be clear, I don’t always identify the best ways to teach entrepreneurship. And I definitely don’t always execute the best ways to do it. But I do spend lots of time thinking about it.
Because of this, when I see someone prominent screwing things up, I get annoyed. Usually, I hold my tongue. But not always.
Such was the case this week. I saw an article from a prominent creator named Tim Denning who publishes lots of entrepreneurship advice around the Web. The entire article was a glaring contradiction. He was literally advising people to do one thing when writing/publishing advice articles while personally doing the exact opposite thin in his own advice article. Even worse, he seemed completely unaware of the contradiction. Or rather, I hope he was unaware, because the other option is that he was intentionally misleading people.
Either way, I think what annoyed me most were all the comments on his article. Nearly all of them included some version of “thanks for the incredible advice.” Why? The advice was so terrible that the guy giving it was blatantly ignoring it!
In response, I wrote an article pointing out the problem. It was a petty move. And, honestly, the guy I’m picking a fight with has 10x the audience I have, so there’s a reasonable chance he’s 100% right and I’m 100% wrong. But still, writing the article was cathartic and made me feel better. If I’m lucky, maybe a few of you will learn something useful by reading it, too.
Sometimes you have to pick a fight to make an important point. Whether or not anyone will agree is, of course, a different issue.
You’ve probably even used it wrong yourself. But do you know the consequences of not understanding its true meaning?
Office Hours Q&A
I was recently lucky enough to close some funding for my startup. It’s allowing me to hire a few people. I already interviewed and selected people, which was much harder than I had expected. Now that they’re working for me, I am also finding that managing them is more challenging than I had assumed it would be. I feel like I’m not doing a good job of helping them know what needs to be done, and I’m still just doing a lot of the work by myself because I feel like I can do it better.
Do you have any advice about managing people that might help me?
You’ve hit on one of my Achilles’ Heels as an entrepreneur. I was (and still am) a terrible manager. Or, to describe it more generously, I have what some might call a “hands-off” management style.
My personal challenge with managing people is that effective managing requires consistent follow-up, and I’m terrible at follow-up. I like to move forward rather than look back. For the most part, this works when I’m operating by myself. However, as soon as I need to keep tabs on what other people are getting done, I get bored.
Back when I was running startups, this translated into me not hiring as much as I could have or probably should have. Instead, I would just take on more and more responsibility (ultimately becoming a major bottleneck).
I mention all this because I eventually learned that my hands-off management style meant I had to hire people who were extremely self-motivated. In other words, I need to be able to tell the people who work for me what needs to be done once and then trust that it will get done without me having to follow-up.
I even use this this strategy in my current job and how I hire TAs. My top priority when choosing TAs is to find students who are self-motivated and get their work done on their own.
You may or may not need the same thing. To be clear, my advice isn’t that you should hire self-motivated people. My advice is that you need to figure out your management style and then make sure you hire people who fit it.
Got startup questions of your own? Reply to this email with whatever you want to know, and I’ll do my best to answer!