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At first glance, there might be a world of difference between professional sports coaches and sales coaches. Yet, those with experience in both sports and sales stress the critical nature of coaching in both fields.

Enter Gary Milwit and Joe Caprio. Gary, the SVP of Sales and Business Development at Stone Street Capital has had a long distinguished career in various tiers of sales management. He also began his career as a high-school football and baseball coach, and was named the Maryland State Athletic Director of the Year in 1998.

 Joe is the Sales Director here at InsightSquared. He was also a three-year starter as an offensive lineman on the Bentley University football team, a team that led the entire nation in scoring during his senior year. This followed a successful high-school football career that culminated in multiple state championships.

Recently the two got together for a conversation about the parallels between sports and sales coaching, why mediocre players or sales reps can sometimes make the best coaches (and why great play doesn’t always translate into great coaching) and how star players – in both sales and sports – should view coaching.

Gary Milwit:

Great players – and great sales reps – have two common traits. The first is that they are world-class masters of their craft. The second is that they know what it takes to be a master of their craft – they must outwork, out-hustle and, most importantly, they must know what they don’t know. That second trait is why the truly great players gravitate toward coaches. They know that coaches spend their lives observing the little things that players need to improve. That is why position coaches – the first-base coach, the linebackers coach, the quarterback coach – or, what I call micromanagers, are the conduit to greatness.

Joe Caprio:

I couldn’t agree more. The star player is always in the moment, he can miss things that an outside set of eyes can catch. Think of a base runner rounding third, headed for home base. He’s so caught up in getting to home that he didn’t see the ball take a fielder’s bounce off the wall. Now, the left fielder is going to gun him out at home. The third-base coach – who likely never made it past the minors in his playing days – can hold up his hands and say “Woah! Stop at third,” saving the baserunner from being thrown out.

That calmer, more discerning take from the coach’s outside set of eyes is how a coach can help a star player. Just like in sales.

Gary: I’m glad you talked about baseball, because I think baseball has it set up the best. You have a manager – like the Sales VP – overseeing everything. The hitting coach focuses only on teaching hitting, the pitching coach focuses only on instructing pitches. You have coaches who focus on specific in-game situations, like the third base coach.

Football is similar, where you have the head coach making sure everyone is doing the right strategic thing, without the tactical X’s and O’s. The bench coaches and the position coaches actually teach and coach skills. Just like your sales manager, who meets with individual reps to break down specific parts about their performance, while the Sales VP sets strategy.

Joe: And the position coaches command so much respect from the star players, despite never having been stars themselves. Take Tom Brady – 3-time Super Bowl-winning quarterback, one of the biggest stars in the National Football League. He spends almost all his practice and game time working with Josh McDaniels, the offensive coordinator and quarterbacks coach of the New England Patriots. McDaniels never played professionally – in fact, the highlight of his playing career was when he was quarterback at John Carroll University, hardly a football powerhouse. Yet, under McDaniels’ tutelage, Brady and the Patriots have broken so many offensive records.

Gary, why do you think it’s so easy for Brady and other superstars to be coached by guys who never made it as players? Why should star sales reps heed the advice of their sales managers?

Gary: The best coaches were usually marginal players who had to learn how to get away with less talent. Who would you want to play for: someone who naturally could play because he was a better athlete, or the guy who had to know to point his big toe to the left to gain a centimeter of leverage on his opponent?

Joe: As a one-time offensive lineman who knows how important that centimeter of leverage is, I’d rather listen to the coach who can point out that little tactical tip to me.

Gary: Exactly. Great, talented players should maximize their performance levels, and then seek to have others point out what they may not know or don’t have time to break down on their own. Brady doesn’t break down film by himself – his position coach, McDaniels, sets up each scenario to watch on film, makes it easy to learn and shows him what the opponent is doing. They collaborate to figure out how to attack the soft spots in the defense. Then they go practice what they figure out. During practice, coaches point out more ways to maximize that performance. The circle continues over and over again.

Joe: The sales coach is the same way. They might not be the most naturally talented salesperson in the world. Their job is to diligently watch for miscues and give honest, real feedback on improvements, both long-term and in the moment. If he can do that with the respect of his players, then he will have a real impact.

In a recent forecasting meeting, I was asked about a particular prospect and I said, “It’s going great, I just put them in trial so I’d say it’s pretty serious.”

My Sales VP said, calmly and inquisitively, “Should we be thinking about where they are in the buyer’s process? Not just in our seller’s process?”

He was right: I needed to do more discovery. I asked more questions on the next call and realized they couldn’t do anything without CFO approval, and I was wasting my time. They were in trial because I had pushed for it.

My Sales VP’s outside set of eyes reminded me about a mistake that I’m constantly training junior reps not to make, yet was actually making myself. Once this was rectified, we were able to rescue a deal instead of letting it go sideways.

Gary: That’s awesome, you love to see effective coaching pay off. It goes back to the micromanaging that a position coach or sales manager does. In business, micromanagement is often viewed negatively. Why? I don’t believe that.

So most sales organizations change the title. Front-line managers are position coaches. They can really micromanage sometimes, focusing on nitty-gritty tactical details. Breaking down calls and listening to every word. Often, that micromanagement can unearth little mistakes or tweaks that can make a huge difference.

To take this full circle, it goes back to the position coach working with the star player. Tom Brady and other star quarterbacks have speakers inside their helmets so that position coaches like Josh McDaniels can tell them exactly what they need to do. They break down film together.

Just as Tom Brady couldn’t thrive in his position and performance without Josh McDaniels, sales reps can’t maximize their abilities without a little outside help – and a discerning set of eyes – from their position coaches.

To sum up, the best coaches get buy-in from their star players. They know what to look for and how to identify the techniques necessary. They don’t take credit, they give credit. They are “how-to” guys.

Coaches lose games. Players win them.

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  • ghdtv

    Thank you very much for the nice info/conversation about the sports sales coaching.

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