Gary Milwit – The Power of Sales Coaching

Gary Milwit is the Senior Vice President of Sales at Stone Street Capital, LLC, a leading specialty finance company that purchases future payments. He was recently recognized by the American Association of Inside Sales (AA-ISP) as the 2013 Executive of the Year.  The former high school athletic director, football and baseball coach is also an avid believer in the power of effective and collaborative sales coaching. We recently had the pleasure of speaking with Gary on a variety of topics including the differences between sales coaching and sales management, the power of data-driven sales coaching and where inside sales is trending in 2013.

 How would you define sales coaching?

Sales coaching is someone’s complete understanding of how the entire sales process, all the people and metrics, come together. Sales coaches have to know what they are looking for in terms of process and metrics, and then be able to identify how to get the skills and techniques necessary from each individual at the highest maximum level. The sales coach is the “how-to” guy. Managers are “what-to” guys, who know what needs to be done – the coach knows how to do it. Coaches or trainers need to know what they don’t know. The best managers know the differences between managing, coaching, teaching, training, mentoring and counseling.

How does sales coaching differ from sales management?

A sales coach doesn’t have to be best manager, but the manager has to know when they need coaching. I have a guy I call my “what-to” guy, he’s the best manager in the world and knows how to communicate things, but he’s not very good at communicating how to do things. There’s a big divide between “how-to” and “what-to” – the coach is the greatest micromanager, and the manager is your macro guy.

The coach has to be able to use micromanagement as a positive – it usually has a negative connotation. Micromanagement is the best thing that you can possibly do for engagement and motivation. We call micromanagement “position coaching.” Management, by definition, is macro down to the “who should do what” level. Coaches, as noted, aren’t managing – they engage, encourage and motivate by working on the little things that make up the entire process. People need it. A lot of managers will say, “I’m not a babysitter.” Why do they say that? Babysitting is actually noble. You’re leaving your kid with a stranger! Why is babysitting bad? Your job as a babysitter is to engage and motivate the kid to go to sleep so you can watch TV. Your job as a coach is to engage and motivate reps to make money so YOU can go to sleep!

Should sales managers be sales coaches?

I think people mix it up a bit. A job as a senior executive is to find out who’s good at managing and who’s good at coaching. A lot of people are good teachers but not good coaches. [Both roles] have different routines. You don’t have to be great at everything.

I sometimes coach more than I manage. I set aside 10 hours a week and meet with 2 individuals every day for an hour each. I give every person that is a manager appointed to me 4+ hours individually with me directly a month dedicated solely to coaching.

What are some important traits of an effective sales coach?

The ability to be engaging and to motivate people. You have to know when you can get really mad at someone – will it send them off in the right way or will they break down and cry? I was a football coach and just like in sales, I had to know who I could grab in the facemask and yell in their face. Some people can’t handle this. You have to know. Your best trait has to be the ability to engage with and motivate each individual. You have to know why they are there, what they are all about. You have to be trusted. You don’t necessarily have to be liked, but your reps have to trust you. Everything you have to do in a sale you have to do as a sales coach.

Another common trait among the best coaches, leaders and managers – and sales reps! – is that people trust them. Give me the 51% of people who want to get better and will follow me because they believe in what we were doing together and that I will win every single battle.

Do you believe in data-driven sales coaching? How have you used analytics and data to supplement your sales coaching?

Yes, yes, yes, yes, yes! It’s ALL about the data. Data drives all your decision-making. Every metric matters. Some of them are wrong, by the way. The key is to figure out what’s working and what’s not. You have to have enough data to figure out what’s working. You don’t coach artists. We’re not artists – we have a job, a process.

Our sales process goes from the meet or qualifying stage to engagement, the building of rapport to the building of trust. How long are they at each stage? What qualifying questions should have been asked? How do you price the transaction based on the questions you’ve asked? How many of these leads in that stage turn into deals and how long does that take? I know the aggregate numbers so if your individual metrics are off, why is that? I know how many offers you need to make, how many calls you need to make, how many leads you need, how many deals are in the final stage of the pipeline. I know the volume targets, the dollar value targets. All that stuff drives how people are doing or what they need. For instance, I had a coaching session today. This rep had a high number of transactions, but not the dollar value of other reps. Why? She was pricing her deals incorrectly, so the metrics tells us that we have to work on that.

How do your sales coaching sessions with individual reps generally work? What is the process like?

My coaching meetings are very individualized and customized. Reps have to bring me their performance goals, and then we create the necessary actions from there and measure them. Coaching sessions work better when they come up with their own goals, because then they’ve already bought into them and you don’t have to micromanage the crap out of them. I have all the important metrics in mind – the key is to get the reps focused on and talking to us about those metrics.

How has your background in athletics administration and coaching impacted your sales coaching process?

Some of the best coaches I ever worked with figured out how to get to the bottom of issues. They figure out how to prepare better than anyone else – preparation is the key to everything. After that, you learn by making mistakes. You have to be able to say that you were wrong.

Athletics is different in that there’s a defined season or time frame that will end. You have a much longer time frame in sales and with that people you work with. You have a longer window to get people to be better and better.

Other than that difference, it’s exactly the same parallel (between sales and athletics coaching). Baseball actually has it set up the best – you have a manager overseeing everything. The hitting coach focuses only on teaching hitting; the pitching coach focuses only on instructing pitchers. You have coaches who focus on specific in-game situations, like the third base coach. Football is similar, where the head coach is the manager, making sure everyone is doing the right thing, without X’s and O’s. The bench coaches and the position coaches, they actually teach and coach skills. Baseball really has [the differences between coaches and managers] down perfect.

Where do you see inside sales trending in 2013?

I have a strong opinion on this – I don’t see a great difference between inside and outside sales. For example, many of my inside sales people actually have to travel. We start from the inside-out but we get on airplanes all the time. It’s not a hybrid – we’re inside sales – but we will get on the airplane to do certain things. If the trust isn’t there yet, we have to build better trust before we finalize transactions. But we still close deals worth millions of dollars on the phone all the time. I see inside sales as the only way to go. The same way that football coaches can call timeouts, we can do that with our inside sales teams as well. Call timeout whenever you want, take the reps off the floor for a breather and some coaching.

A trait to develop to be successful at managing inside sales – you have to understand that everyone’s different. We all try to put square pegs in round holes. You have to figure out what people can do well. I get in the way more often than not when I put people in a position that I want them in, instead of the position they should be. There’s no such thing as a perfect person. That’s real life. I don’t have to work as hard at some of the things I do, some things come naturally to me while others are a struggle. Inside sales reps are the same.

What are some of the biggest and most common challenges in sales coaching today?

The biggest challenge is in not dedicating enough time for management to do it. We took people off the sales floor three times a week for 35 minutes each time. I had five different groups every day for seven months in a row and their sales went up. I took them off the floor whenever I could. The hardest thing is simply finding the time.

The second hardest thing is to coach people who are your peers. Then, it becomes more like mentoring. Mentoring is “watch what I do.” A coach is more like “let’s try it this way.” A coach has to be willing to lose. They don’t take the credit, they give credit. Coaches lose games, players win them. Anyone who thinks differently doesn’t have it right. You have to be willing to take the hit every time you lose. A bad coach in business is one who says, “I told that person to do that a thousand times!” That coach has failed. The hardest thing to do is to blame things on yourself. It’s not always about my way; it’s not necessarily the best way.

Find out more about Gary and Stone Street Capital, LLC at or follow Gary on LinkedIn