One of the things I’m trying to accomplish with this blog (and with my life at this point) is improving the way in which entrepreneurs are trained. One of the core elements of entrepreneurial training is coaching. I’ve had a fair amount of experience with coaching in different contexts. I’ve coached improv teams (at IO and the Playground in Chicago), and different entrepreneurs starting businesses (Go Comedy, and various entrepreneurs at Bizdom U), and I’ve picked up some tips from some great coaches. So here are some tips for coaching people. BTW, these tips can apply in almost any context where you’re helping someone. If you’re working with someone to help them – then essentially you’re coaching them.
Sympathy for the Devil
Before launching into it, a few words on Mike Leach. Unless you follow college football (and if you don’t you’re a communist), you may not know this, but Mike Leach was the Head Coach at Texas Tech. Generally praised for innovative pass-oriented schemes, he was somewhat of a maverick among coaches. He recently got fired for mistreating a player. I’m not here to defend his tactics (although I’ve dealt with my fair share of people whom I thought were faking it when they claimed they couldn’t do something). Rather I bring it up to simply say that coaching is a tricky business. When your mission is to maximize someone’s potential, you often find yourself doing weird things that you barely understand, much less trying to justify what you’ve done in the court of public opinion. In other words, being a coach, I feel your pain Bobby Knight and Mike Leach. Also, your mileage may vary. These tips have worked for me and helped me. They may strike you as a bit nuts. But listen to a Knute Rockne speech. Coaches are nuts.
3.5 Guideposts for being an effective coach
1. It’s Not About You
It’s very important to focus on your goal as a coach – to maximize the potential of your players/coachees. It’s not about buffing up your glory, making you feel good, validating your worth, etc. It’s about them. Be willing to do anything to achieve your goal – even if it deflates your ego, takes you down a notch or look like an idiot. You also need to be willing to be thought of as an asshole – and play the part of asshole when necessary. Some people are motivated when pushed. Some people are motivated to prove somebody wrong. You may need to be an asshole to motivate these type of people. Be willing to be hated, despised, and the object of scorn. Everyone loves success – and if you can help people achieve success, it won’t matter whether they love, like or respect you. Your job is to put them in the best position to win. Do that because nothing else matters. If you need unconditional love get a dog, don’t look to your players.
1B. Don’t cross the streams
Don’t become friends with your coachees. It’s okay to like them, and when you’re no longer in the coach/coachee relationship, you can be their buddy. That doesn’t mean you can’t be friendly with them. But don’t forget the essence of the relationship.
2. The first pulse you take is your own
While you may occasionally need to take on the demeanor of an asshole or screaming lunatic, internally you’ve got to keep your pulse in check. This is along the lines of not hitting your kids in anger (really – never hit your kids – but you get what I’m saying). It’s okay to be angry, frustrated and even incensed to the point of blinding rage – but you always need to make sure the choices your making in your coaching behavior are coming from a space of maximizing performance – not venting your spleen. If you need to vent your spleen, kick the dog you bought back in tip #1.
3. Know your role, and shut your mouth
Your role is to maximize performance. By focusing on that, and remembering that, you’ll realize that you needn’t coach everything that’s coachable. I see rookie coaches absolutely destroy people’s motivation by criticizing everything that can be criticized in a performance, game or business plan. If you call out every single thing that needs improvement, you’re not coaching, you’re showing off how knowledgable you are, and how observant you can be. That makes it an ego driven process – and – tip #1 – it’s not about you. You’ve got to say and do just enough to motivate maximum performance, then shut the fuck up.
Got any good coaching tips or experience with coaches you’d like to share? That’s what the comments are for friend!

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Dan,
While I do agree with you that you shouldn't criticize everything at once, working on fixing one skill at a time helps the person you are coaching to focus and improve more quickly, don't forget that no one cares how much you know until they know how much you care. I'm not saying throw them all bachelor parties, but you have to let them know that you are their friend before you can be hard on them. This way they know you are doing it for their own good.
I coached competitive swimming and swam for 7 years while in school. The coach I listened to the most took a personal interest in what was going on with my life, he showed up to team breakfasts and dinners and made it clear that he wanted us to improve because he cared that we met our goals at districts. I swam faster under his coaching than I did the Marine drill sergeant who replaced him when he moved to another state.
This transfers over to what I have seen in business as well. My favorite sales coach was very strict and a bit of a micro-manager at times but he treated us all like family. He made sure he took time every day to come over and just ask about our personal lives. I confided in him as a friend and respected him when he had to be tough on me. Not only that, we all made a LOT of money. More than anyone else in the company! I worked long hours and didn't mind because I felt like I was part of a supportive family. I'm still good friends with most of our team, including that coach, today. Just like sales, being an entrepreneur is a tough job with a lot of negativity and it's nice to know that there's always someone to re-motivate you when you're down!
Mike
Excellent comments. I do agree that they need to know you care. They should intrinsically know that you're coaching them for their own good – but a healthy dose of reminding them of that does go a long way.
I'm still very cautious about letting them think I'm their friend. I don't want to confuse the fundamental nature of the relationship – coach and coached – and frankly I don't like everyone I coach. I like my friends. Friend also implies that we'll have a relationship beyond the coaching experience – and that's not always true or possible (or proper).
The great thing you hit on in your last paragraph is the sense of feeling like you're part of something. This is a huge motivating factor for people and will energize them to feats of greatness – as it clearly did with you and your sales coach. Great point!
Thanks for reading and commenting.
Izzo, this is excellent!