Welcome to the December edition of our Sales Influencer Series — a blog series that delivers insights and anecdotes from the best minds in sales. 

I had the pleasure of chatting with J. Ryan Williams, an executive coach and consultant who focuses on sales. He's also the founder of SalesCollider — a community of founders, mentors and coaches. Ryan sees 300-400 founders annually, and in the past year, he's been to 15 different startup accelerators in 12 different countries, sharing his experience and expertise with teams across the globe. In our interview, he lets us in on a few of his sales coaching secrets, including:

  • Getting buy-in from your sales team
  • Advice for a first-time sales coach
  • Hitting the right coaching cadence

Check out the transcript below, or watch the full interview — friendly banter and all — here.

Jared Houghton: J.Ryan, let’s kick this thing off.

Ryan Williams: Thanks for calling me today.

Jared Houghton: Folks, Jared Houghton from Ambition.com, excited to bring another great sales leader through the Sales Influencer series. There's probably no better person to talk to than J or J.Ryan or Ryan. We're not sure. We don't know his real name. I think we're going to go with Ryan. What should we go with?

Ryan Williams: Ryan is what my mom calls me.

Jared Houghton: Right.

Ryan Williams: To you Jared, since we're family, Ryan is just fine.

Jared Houghton: I'm going with Ryan. We're going to jump into a few tactical and strategic coaching best practices. So tell us a little bit about your sales leadership style — and how do you get the team to buy in?

Ryan Williams: A lot of folks will complain that there's not a traditional sales path academically. You can't go major in sales except for a couple of different schools. But for me, I got into sales by accident.

I was raising money for Boys and Girls Club, when a friend of mine dared me to move to San Francisco. He said, "Hey, we're all out here. It's a lot of fun. We play golf in February, even though it's not LA weather. Come out and see what happens." So I ended up being an early sales person at AdRoll and then, grew to be their first sales manager, which is I think where you and I get connected.

But my background prior to that had been education — doing teaching, doing social work. So one of the core principles, whether it's in a classroom or in the social work setting of helping people is the process of self-determination. You want to support them, know what direction they want to go.

When somebody asks me about my leadership style as a sales leader, I usually tell them that the number one thing is to be focused on your people — to figure out what they want and then help them go achieve that result. Whether it's to win their deal, to grow into a management career, to learn a new environment.

There are a lot of sales people who get in thinking, I'm just doing sales so I could go to marketing next. I think that's a fine ambition. If that's your ambition, then let me support you, learn about what you need to know about this market, so that you can be the strongest force on the marketing or product marketing team. So it's really, it's just kind of like, “rep first” is the way I think about it.

Jared Houghton: Yeah, I think that I've seen that with you and your team and I couldn't agree more in that philosophy. So coaching is talked about so much nowadays, but it seems —

Ryan Williams: Very buzzy.

Jared Houghton: Right. It is. It's like ABM is not necessarily a new thing, but it's being branded as one. I feel like sales coaching is the same way — just basic good management. But in your words, what does it mean to be a good sales coach?

Ryan Williams: Well, let's talk about coaching in general. Coaching in general is about: how do you help someone accomplish their goal? Whether it's running a faster race or whether it's improving their golf swing. It's about, "What is the goal? What are you trying to achieve?" For me, I think that's just an extension into sales, right?

So when you're working with a sales team, and you're focused on, "What does that seller need?" That's where it can also become coaching. But that seller doesn't just need coaching. They also need good management. They also need somebody to help them with analysis. They also need someone to help them support and mentor them. Those are all different tools. So if you will, if I had to boil it down to kind of one definition, then coaching is the ability to help someone take it to the next level.

Jared Houghton: Do you have a tried-and-true system or cadence that you check in with your people? Is it weekly? Is it monthly? What did you find worked?

Ryan Williams: Typically, with the reps that are reporting to me, I try to stay on a weekly cadence when I can. Obviously, when you're managing a really big team or a team that grew really fast and you're between thing awkward growth stage, where you haven't brought in enough management to get enough one-on-one time with people. That could be really tough and you might go, every two weeks or so.

Jared Houghton: You're obviously a thought leader in the space of coaching. For those that are maybe starting coaching or just in their first sales management role, what practical advice would you give those folks?

Ryan Williams: I'd say, for me ... I guess, the practical advice I have is probably three things. Number one, is start asking people what they need from your meetings. Number two, is being transparent. Being transparent about what your motivations are.

I think one of your neighbors, Gary V., like to talk about how much he wants to own the Jets. He tells everybody in every meeting he has, "I'm just here because I want to own the Jets someday." Great. He knows his motivation and he tells everybody about it.

On the sales floor, it's a little bit different. You're not going to start with, "Hey, my career motivation is to be a sports club owner." It might be being clear about your motivations of saying, "I want to build the number one team." Or, "I want to manage a big team. I want to grow a team to 100." So now I know that what you're trying to do is grow your team.

The third thing is building process around what that rep needs and I'm going to give you an example of that in a second, okay? So the first thing, ask for what somebody needs. Whether that's the start of your one-on-one's or that's the start of your relationship. Knowing what somebody needs is really important to be able to take them to the next level and really be their coach and part of that is setting that up.

Typically, in a first coaching session, where that's the only relationship you have as opposed to me being your manager and your coach, but if you just came to me and say, "Hey, I'm looking for an executive coach." One of the first things I'm going to do is I'm going to ask you for some boundaries and some rules of what you're comfortable with. "How often do you want to meet? What types of things do you want to work on? Why are you here? What's bringing you to this meeting?" Right?

These questions are going to really help set that ground rule. A lot of times, I'll set a boundary around confidentiality. "This is what we're going to talk about and this is also something that's not appropriate or appropriate for us to discuss." Right? As a manager, it's not always going to be that clear on when I'm a coach and when I'm a manager. But if I ask you what you need and say, "Hey, what do you need right now?" Do you need a coach right now? Or do you need me to tell you what to do?"

I think a lot of reps will say, "It's okay for you not to coach right now. Just tell me what to do." But as a manager, you got to see, there's some opportunities for teaching where you can make that rep 10 times better if you help them kind of control that. That's one that's asking for it willingly.

The transparency, I think we already talked about. But really is, being transparent about what your motivations are. “We're in this meeting right now because you're at the bottom 20% of this group, but I really want you to come up. We're going to put a plan together and the reason we're putting this plan together is because I need you to do X. Because I want to run a team that doesn't have anybody who's under quota.” You're being transparent about those motives.

All right, so here's the third thing and this is something that I tell all first-time managers. I think you might be surprised at how often we have to talk about this for seasoned managers too. But I believe that you should build process on your team around what it takes for that rep to be successful. This is why, one of the things that I've always done is made sure that my sales operations team is building the right dashboard to bring in the right tools in.

 For all the managers listening, think about what tool or dashboard does that rep need to see or look at or do to make sure they're getting the information they need. So I don't ask reps to put anything in Salesforce that they're not going to get value out of. Maybe put the market size in there, you put the total number of seats in there, you put an estimate to what that deals going to be. I gotta make it pay off for you.

So if you start estimating your deals, I want to show you where you're at in terms of quota, right? So I've got to do that. I can't just say, "Give me information without me building a system that's going to give you information back." So I'm always pushing sales op to say, "What do the reps need to see? What do they want to see, so they hit their goal?"

Then, a byproduct of that should be the management tool, so that I'm going into my meetings with my boss with a little more information about pipeline, a little more information about forecast. 

But it's really around, "Can you help the reps get what they need and build a process around them? Can you be transparent about your motivation? And then, can you ask people what they need?" You'll be surprised at how well those three things work.

Jared Houghton: I totally agree. I mean, I think too often, people talk at people. When really they should just understand what is it that someone's struggling with. I think most people are their own biggest critic and in today's world, I think they actually want help with it more often than not. You're one of the guys that I've actually seen do that really, really well. So I appreciate your insights.

Ryan Williams: Thanks man.

Jared Houghton: I think the Ambition blog readers will as well — and I just lost my lights in here.

Ryan Williams: Oh, that means it's time.

Jared Houghton: Maybe that's time.

Ryan Williams: That's the gong.

Jared Houghton: Thanks again, J. Ryan. We'll talk to you soon.

Ryan Williams: Talk soon.

For more coaching talk, check out our recent interview with leading sales coach Kevin Dorsey.

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