Daniel Irwin: Coaching Strategies for Sales Leaders (Ep. #9)

Published on
January 21, 2020
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Building Better Managers Podcast Episode #9: Coaching Strategies for Sales Leaders

Your Sales Enablement program starts with things like collateral, presentations and training. But great sales leaders know how to coach the behaviors that get results. Feedback, accountability, and psychological safety keep your Top Performers performing.

In this episode, you'll learn:

Meet Daniel Irwin

  • Bio & Background
  • Why Sales?

How Coaching Influences Leadership Style

  • New Manager Problem
  • Authoritarian Leadership Issues
  • The Coaching Approach for Leadership

The Importance of Relationship Building

  • Team Member Needs, Wants and Goals
  • Connection on a Personal Level
  • One-On-Ones

Understanding the "Why"

  • Direct Reports
  • Prospects and Clients

Feedback & Accountability

  • Differences in feedback: Managers & Direct Reports

Creating a Highly Collaborative Work Environment

  • Results instread of "Judging"
  • Keeping your Top Performers challenged and fulfilled

Breaking Through Walls in Conversations

How to Regain Confidence When Numbers Are Lagging

  • A) Understanding what you're doing differently from a coaching perspective
  • B) Finding ways with your personal relationships to get those little boosts of satisfaction that you would typically get from helping somebody close revenue.

Keep Learning!

  • Great ideas often come from outside of your specific field.

Reading and Podcast Recommendations (see below)

Downloads & Resources

Follow Dan on LinkedIn.

Dan's podcast recommendations:

Dan's recommended reading:

Subscribe to our podcast on your favorite podcast platform!

Check out our blog articles on Leadership here.

About Daniel Irwin

Dan is a Phoenix native, attended college in Boston, and has been back in Arizona since 2010. He began his professional career at Yelp where he started as a sales rep and worked his way up to sales director. As a director, he had about 150 reports between managers and sales reps, and held a director position for 4+ years before moving to BuildZoom as their Head of Sales last summer.

View the episode transcript

WENDY HANSON: Welcome to our first podcast of 2020. I'm so delighted to be here with you all. We all start the year with vision, goals, and for many of us we have a sales goal at the beginning of the year. Today we have the pleasure of talking to Dan Irwin about leading a sales team and how he has brought in coaching skills and how that has informed his leadership style going forward. This could really make a difference with you and your team in 2020 so I would suggest you really listen up.

WENDY: So let me tell you a little bit about Dan before I bring him on. Dan is a Phoenix native, attended college in Boston, and has been back in Arizona since 2010. He began his professional career at Yelp where he started as a sales rep and worked his way up to sales director. As a director, he had about 150 reports between managers and sales reps, and held the director position for 4.5 years at Yelp before moving to Buildzoom as their head of sales last summer.

WENDY: So we are delighted to have you join us. Thank you, Dan. Welcome.

DANIEL IRWIN: Thanks Wendy.

WENDY: It's just so wonderful to get information out to our listeners for somebody who's in the middle of it and is doing it. So that was your bio, just a brief bio, but what else would you like people to know about you? What is it that you like about your role in sales?

DAN: Man, I'm really, really competitive, which I think is good in some situations and detrimental in others. I like sales because you always know how well you're doing. I don't have to rely on somebody else for feedback constantly to tell me how well I'm doing. I know because the numbers tell me how well I'm doing. And I also know how well I'm doing compared to my peers or compared to the goals that are put forth for me. And I think that's really helpful and motivating for me.

WENDY: Yeah. I love that. You have a way to be able to see how you're doing and adjust accordingly. And oftentimes we don't have that in every position that we're in.

DAN: Right.

WENDY: Yes. Tell us a little bit about your background with learning, the coach, and how it's informed your leadership style because I think that has a lot to do with your current success.

DAN: Yeah. Well, I think when I first started as a manager, like most new managers, I was overwhelmed and wasn't positive that I had a future as a leader. And then I started to do really well in a short period of time. And then I thought that I was the best leader ever. Then no one could ever beat me. So early on, I think I had more, not really an authoritarian leadership style, but I was really confident that the way that I thought a rep needed to behave to be successful was the way that a rep needed to behave to be successful.

DAN: And over time, I think the way that coaching has changed my approach is forcing myself to be more and more open to feedback. As a leader, you're used to giving the feedback, not necessarily receiving it, and the more frequently I receive feedback, the more frequently I solicit it, the more painful it is, the easier it is to continue to solicit feedback and implement it, and the better you get at your job. And then really you understand that there are different perspectives and instead of having one great tool in your tool kit, you've got 10 great tools, and 20 others that are pretty good. And you acquire all of those tools as a result of learning from the people with whom you work.

WENDY: Yeah, I love that because I think oftentimes leaders don't always put them in that position of really being the learner. And I think that's what coaching brings to the situation. We have so much if we can really listen and learn. And so how would you describe your style before and your style now, if you looked at how you worked with individuals?

DAN: Building good relationships, strong individual, personal relationships has always been really important to me. I think that's the driver if you want to be a good leader, is you really genuinely need to care about the people who report to you. And for me, what helps me do that is to learn about them as people, learn what they really want to do in their lives outside of work, what kind of experiences have shaped them. And that has never changed. But I think just my maturity level as a person has changed. I mean, when I started managing people I was 27 and had only had a career for two years. And the things that I like to do in my free time are a lot different than the things that I like to do now. I have a daughter, another daughter on the way. I've been married for three years. So it's a much different. Now, I have favorite grocery stores instead of favorite bars.

DAN: So I relate in a different way to the people who report to me. And I think that just having more life experience and maturing as a person has made me less defensive and more confident in myself as a human being. And I don't need to feel like I have all the answers all the time, and I don't need to feel like somebody who reports to me must respect my opinion at all times or must think that what I'm asking them to do is the best thing to do. And it's actually much more important to me that somebody is honest and genuine, and if they think that I'm asking them to do something that is unproductive, then just tell me. And we can have a conversation about it.

DAN: I think most leaders pay lip service to that concept, but as you get older and gain more tenure in a leadership position, that concept is more and more in line with what you're genuinely hoping to do in your role.

WENDY: Yeah. I love how you point out getting to know your people better and what they need and what they want. And I think that's a big part of the coaching and being able to use that skill when you have one-on-ones with people. I think a lot of people out there that when they have one-on-ones, it's their opportunity to just download. Here's everything that I want you to do. Which is not the perspective that we hold a better manager. It's more, this is my chance to listen to you. Tell me about your one-on-ones. What's been your experience there?

DAN: I try to take the first 10 or 15 minutes to just talk about personal life stuff. Sometimes reps are really focused on getting into the weeds and I just deflect their questions. So if they start asking me work-related questions, I'll just ask them a question about their personal life.

DAN: So anything that I think will help me gain insight. So the holidays just occurred. So I'd ask reps questions like, hey, what's your favorite gift that you received this year? And then I ask followup questions about why that is, what kinds of other stuff they got. I usually can learn a lot about their family dynamic that way, how they grew up.

DAN: Those types of things are really important to me because I want to know why that person wants to close the amount of revenue they want to close, not just because they're going to get commission, but because there's something they can do with that money. And then once I learn what it is they want to do with that money, I'm trying to figure out why that's important to them. So it totally changes how you coach.

DAN: So I'll give you an example. There are tons of them that I can think of. But one in particular, there was a manager who worked with me for a long time and he wanted to buy a boat, so it was really important to him to do well so that he can generate enough revenue in his variable comp to buy a boat. And what I learned was that the reason he wanted to buy a boat was he had moved away from his family in Michigan, and his grandfather, who was the patriarch of the family, had a boat, and all their family gatherings would be on a boat.

DAN: And so for him, owning a boat, it represented him starting this life that he envisioned for himself, that was basically modeled after his grandfather. So when I was coaching him to do different things that made him uncomfortable, I wasn't coaching him to do those things so that he could close more revenue or so that he could help his reps close more revenue. I was coaching him to do those things so that he could model his life after his grandfather, which is typically a lot more motivating. And it's really hard to get to that place with people and I probably only get there with maybe 60% of the people who ever report to me. But it makes your job a lot easier as a leader if you really know why somebody is coming to work every day on that level.

WENDY: Oh, I love that story because it really is what leadership is all about, understanding someone's why. Why is this important to him? That's just so brilliant to be able to get to that level. And when he's having a tough day, both of you can go to the boat and talk about that. How can we help you get to that boat? Yeah. Oh that's great.

WENDY: You know, full disclosure, you were coached at Better Manager when you were at Yelp, and you learned a lot of coaching skills, like listening skills and how to ask people open-ended questions and keep them accountable. And you just did a great example of the why behind decisions. What do you think is the most challenging that you've seen with other sales leaders in really using their coaching skills both at one-on-ones and just keeping the motivation and the focus of the team up?

DAN: Well, I think there are a couple of things. Number one that comes to mind, having coached a lot of managers, is the accountability portion. For people who are new to leadership, it's tough because you're not receiving feedback as consistently as you would receive it as an individual contributor. So it's not like every single day you can tell whether or not you're doing well based upon the different sales activity you have and closing revenue.

DAN: As a manager, you move into this role and you don't really know how well you're doing for longer periods of time, maybe a few weeks, a month. Oftentimes when you're first becoming a manager, you're not responsible for revenue right away. So the only way you know or the only way you think you know that you're doing a good job is based upon how you perceive your team to feel about you. So whether or not they like you. And I think a big mistake that a lot of leaders make early on is they just focus on getting their reports to like them instead of helping their reports do whatever is that they want to do. So it goes back to understanding what the goal is of the people who report to you and then genuinely putting that goal at the forefront of your thoughts.

DAN: So if you really want to help somebody accomplish whatever it is they want to accomplish, and they're behaving in a way that's not going to help them get there, it will be easy for you to intervene and help them understand why what they're doing isn't productive, even if it's uncomfortable for you. Even if you think that it's going to make them not like you in that moment or not like you for a couple of weeks, you're happy to do it. You might not be excited, but you're happy to do it because you know it's going to help that person accomplish their goal. And when managers don't have that point of view, it's really a selfish point of view, they put their own comfort ahead of the achievement of their reports, that's when they avoid having those conversations. So I think the accountability pieces of is a big one.

WENDY: Yeah, because oftentime accountability doesn't happen, just like you say, because people are uncomfortable calling people on it. They also have not really been clear on the goals and the parameters and the expectations. So then it's hard to come back to somebody and say, why didn't you do this? So I love that.

WENDY: And it really does come down to that relationship piece. How do we have a relationship that we understand somebody's why. And in my experience, I've been coaching sales managers for 21 years, not just sales managers but a lot of them. And sometimes people come with this, I have to like really push people to make things happen. And that just always blows up in their face if they're just trying to push people. But be insightful. And I think that's certainly what I hear you saying.

WENDY: Any other examples? I love your examples of the impact that your style of coaching and really getting to know people, asking the right questions rather than just telling them what to do. What kind of impact has that had on your team?

DAN: I think it just creates a more collaborative work environment and it creates a place. If I'm thinking about my team, the thing that's most important to me is this concept of psychological safety. So this idea that people can say whatever they want and they're not going to be judged for it necessarily or they're not going to feel stupid. And I know that it's really hard to do that, and I know that I'm not always great at it. But it's always my goal. I'm always thinking about how can I make people feel comfortable. If they have some idea that they're pretty confident is not in line with whatever sales methodology or philosophy I ascribe to, will they be comfortable talking to me about it? And I hope that the answer is yes.

DAN: And I think when you create an environment that provides that psychological safety, then it trickles down from managers to reps, and people are excited to come to work because they can be creative. Even if they don't necessarily implement a lot of the ideas that they have, they can at least express them and talk about them and they're not going to get judged for them. And typically I encourage people to pursue whatever it is they want to pursue. So I think that really changes the dynamic of a team, is everyone being comfortable expressing whatever ideas they want to express.

DAN: And then the other piece is really focusing on the top performers. I think making top performers feel comfortable. The thing that top performers dislike the most are people who they don't think are working hard. They don't resent people who aren't doing well. They resent people who aren't doing well because they're not working hard. So I think you just kind of have to have a zero tolerance policy for those people, because if you're afraid to hold people accountable who aren't working hard and who aren't implementing feedback, then you're going to lose your top performers even if they have nothing to do with the people who aren't implementing the feedback.

WENDY: Yeah. I love how you differentiate those that aren't trying versus those that aren't succeeding. But they are trying and then that's how you get a team to rally around each other and help move the ball ahead.

DAN: Yeah, absolutely.

WENDY: Have your sales team members, learning your style and coaching and standing back and asking them what questions and things to see what they're thinking, have they been able to use those kinds of coaching skills when they reach out to customers? How do you teach that piece of it? It's the other side of the coin.

DAN: Yeah, I think so. I think it's the same idea. We want to uncover pain points before we present them value proposition to make it feel organic. In any sales context, that's what you want to do. You want to uncover how your product would help solve a problem that exists before the prospect understands that you have a solution to that problem. And the only way you're going to do that is by asking open-ended questions and followup questions and asking hey, tell me more about that. Why is that?

DAN: So I think so. It's the same kind of questions that a manager can ask if they hit a wall in a conversation, a sales rep can ask if they hit a wall with a prospect. So you don't know what to say, just say, tell me more about that. All right. You know, it's easy stuff.

DAN: So I think it does translate. It just depends on the type of sale. In some roles it's important at certain times to not ask a lot of questions. If it's a high volume, outbound sales with really short sales cycles, low barrier to sale, so it doesn't cost much money, you don't necessarily want to ask a ton of questions. You just want to figure out, there's a general value proposition that you know is true for every prospect and then you just hit them over the head with it again and again and again.

DAN: The type of sale that I like is a little more complicated where you really do have to take time to understand what the pain point is for the prospect and then figure out how you're going to position your product so that it's clear to the prospect that you can solve their problem.

WENDY: Yeah. I'm intrigued about going back to the why, because you were talking about that when you're talking about really connecting with people on your sales team. If somebody on your sales team is connecting with somebody, where do they need to understand the individual's why, like the person you're selling to, and then the why for the sale? Sometimes there's two different things,.

DAN: Right. Yeah. It's always going to help you. So when I was at Yelp, we sold advertising. And one of the concepts that I would talk about a lot is understanding what the business owner would do with the extra money that they would make.

DAN: So the first step was to identify how much more money a business could be making without changing anything about how their business functions. So without hiring any more people or changing their operations, how much more money could they be making? And there are different ways to do that. And then once you get that dollar amount, you don't want to stop. You wanted them determine what they would do with that money. So maybe they'd take more vacations, maybe they'd hire somebody to do a bunch of their work. So instead of working 70 hours a week, they can work 40 hours a week. Maybe they would invest in new equipment so that they can take on bigger projects and make more money. Maybe they wouldn't invest in more locations and other crew, whatever.

DAN: And then you sell that. You're no longer selling advertising, you're no longer selling the opportunity to make whatever, 50 grand more a month. You're now selling the opportunity to open up a second location, or you're selling the opportunity to retire five years earlier. And if you can learn that stuff, if you can learn how to get that information, then you can be really effective.

WENDY: Yeah, and do it in, which I really get about you, do it in an authentic way that you truly do care. This is not just about the sale. Right. You have to show the integrity piece of I really do care that this is going to make your life better. Those were great examples.

WENDY: One of the things that I think we all struggle with in leadership is how to maintain confidence, to know that we're heading in the right direction. And I know that you've thought about this a lot. So, tell me about confidence and how do you put it out there and display it to your reports so that everybody feels safe, secure moving forward?

DAN: Yeah. I think it would be very unique if a leader in any context, particularly though a sales leader didn't struggle with confidence pretty consistently. I can think of three or four really just pointing at examples of that myself in my career. And the way that I have gotten through it and regained confidence is taking a two tier approach. On one end, it's the relationships that I have with the people who report to me and then on the other end it's what I'm actually coaching people to do.

DAN: So with the coaching, which is a little less interesting in my opinion, it's just getting back to basics and reminding yourself of all of the things that you were doing when you were doing really well, when you were performing well and were really confident. Always those things have changed, and we typically just aren't aware of it. But they have always changed because they change so gradually and over such a long period of time. It's not noticeable to us, but if we really take an inventory and our self reflection is as honest as it can be, it will be clear that we are doing things differently than how we are doing them in the past from a coaching perspective.

DAN: And usually what you're doing is not talking as much about the basics and about the process, but instead focusing solely on revenue and then you have people just nervous about closing revenue all the time instead of thinking about the incremental progress that leads to the revenue.

DAN: Then on the personal relationship note, you have to remind yourself of the things that you're good at and then help other people around you within the context of what you're good at. So a lot of the people who've reported to me in the past, a lot of the managers who've reported to me in the past have been young in their careers and they're now starting to make money in a way that they haven't before. So I'll ask a lot of like financial questions and stuff like that. And so I would really double down on the non-work-related life advice when people would ask for it. Not unsolicited, but when people would ask for it, because it would make me feel good. And then I could have a win, someone would come back and say, hey I did that thing you asked me to do and this is how it's changed my financial situation. Or two months later I paid off all my credit cards because of that. And that can can help boost confidence in the same way as helping somebody close a lot of revenue.

DAN: And then also I think soliciting feedback because it's never as bad as you think it is. For me, I'm so competitive and so focused on the end result that I assume everyone around me functions the exact same way. And so if my team hasn't been doing well for a period of time, I assume they're all very disappointed in me and are wishing that they were reporting to somebody else.

DAN: In those moments when I solicit feedback, I'm always surprised by the fact that the performance isn't necessarily what's upsetting them. It's always the way that the dynamics of the personal relationship has changed or the fact that we're now 100% focused on revenue all the time instead of process-based goals. I'm not having as much fun because I'm not as relaxed. It's like that kind of stuff.

DAN: And so I think again, the confidence piece is really about A, understanding what you're doing differently from a coaching perspective, and then B, finding ways with your personal relationships to get those little boosts of satisfaction that you would typically get from helping somebody close revenue.

WENDY: Yeah. Like I'm on the right track. Right? We need feedback to know that we're on the right track.

DAN: Yeah. Yeah. It crushes the storytelling. It's like if you're thinking from a cognitive behavioral therapy standpoint, that story that you tell yourself that's not aligned with reality. It's easier to kill the story that's unproductive.

WENDY: Yeah. That little voice we all have in our heads. If we buy into it all the time, there goes lack of confidence. Right? Confidence is down the tubes. And what I love about what you're saying too Dan, is that it sounds like you do a lot of self-coaching. Once you learn how to coach, you can't help but having that coaching voice in your head. What is it that I need to do today with my team to move this forward? How am I showing up? That part of reflection is so important and I think sometimes we just put our heads down and we work and work and work and don't do that. How do you handle reflection and I'll call it self-coaching piece of your work as a sales leader?

DAN: Yeah. For me what's really important is learning. I have found that when I feel like I'm in a rut at work, it's often because I stop learning outside of work. So I listen to a lot of podcasts. I read a lot of books when I'm traveling, and then I listen most of the time on Audible. Early in my career I read a ton of sales books and a lot of business books and I don't do that as frequently anymore. They're pretty redundant. And I find the topics that give me the best ideas are usually neuroscience, cognitive psychology, evolutionary psychology, stuff like that. Those topics make me think a lot about work. And then a lot of sports psychology is also very applicable, typically for me.

DAN: So I am trying to get new ideas all the time. And then when I get a new idea I try to hold myself accountable to implementing it, which sometimes I do a really good job and sometimes I don't. But I think just in general, once every quarter or once every six months I send out a feedback survey to the people who report to me and ask for feedback. I will know the things that I'm doing really well because no matter who you are as a leader, there are probably some things you're doing really well. And then I'll know what things I need to improve. And then I can go out and solve the problem instead of coming in and being lost. For me, the self-improvement and the self-reflection is always anchored in the feedback.

WENDY: Yeah, that's great. And it's tangible. You're not making it up. You're taking it from reality and you're really asking it on a regular basis so that people can help you grow and therefore they grow. So that's awesome.

WENDY: Are there any podcasts or books you can say off the top of your head? Otherwise, we'll put them in the show notes. Not to put you on the spot. So if people are listening, they say, whoa, I want to listen to this. I love your focus on neuroscience and things. That's just brilliant to look at it from that perspective.

DAN: I really like Farnam Street.

WENDY: Farnam Street. Okay. We'll put it in the show notes. Yeah.

DAN: Great. And it's called the Knowledge Podcast. That's a good one. That's mostly business-based. There's a podcast called the Psychology Podcast, which is ... It's called the Knowledge Project. Sorry. The podcast is just called the Psychology Podcast and I think Barry Goldstein is the name of the host. But no, not Barry. I can get it to you.

WENDY: That's okay. I'm putting you on the spot. Yeah, we'll figure those out. But I love that you listen to things that are outside of your domain. People might not think about that. They might just be listening to sales podcasts, business podcasts. But you're taking learning from different areas and certainly the sports one, we can all look at teams and how to make teams grow and learn from sports leaders that are successful. So I just love that you take new information, and then that you put yourself on the hook for let's take one of these ideas and make it happen.

DAN: Yeah, I honestly think that a lot of the business stuff is distracting for me because it makes me more ... Like LinkedIn distracts me. I don't know if this is true of a lot of other people, but for me it makes me think about other opportunities instead of what I need to do or where I am right now. LinkedIn to me is just look at this, look at this, look at this, look at this. And that's not going to help me do what I need to do so that the people who report to me can hit their goals. So I try to stay off of LinkedIn. I don't have Facebook. I don't know, for some reason the business stuff seems like more of a distraction than the thing. Maybe it's because it's not really rooted in a lot of data typically. It's just here's the fold wisdom from this person who happened to do really well in business.

WENDY: Yeah. And you're looking at neuroscience and cognitive therapy and how we change behavior and those are more rooted in science. So I love that perspective. Wow. So Dan, final question. Is there anything I should have asked you about that I didn't? What do you want to leave our listeners with as we take this great ... I love your examples today. I loved the inspiration and the understanding of the why. But what should I have asked you that I didn't?

DAN: Well, something that we were talking about, I think before you were recording was this mindset. I didn't arrive at this myself. It was something that I heard somewhere, or learned from someone else. But this idea that when you see someone else doing something and you think it doesn't make any sense, especially for leaders who have experience, the typical reaction is to say, oh, that is so dumb for reasons one, two and three.

DAN: Instead, if you just make your default mode of thinking I wonder why that person is doing that, you learn so much more. And that has been really helpful for me, because as a competitive person and a human being with insecurities, I think that what I tend to do and what a lot of people tend to do is just immediately identify all of the things around them that aren't going well, and say hey, this is why I would be better at that. Or this is how I would do these things better. Or to see how people behave around us and say, oh, that's wrong for these reasons. And then that thought process juices our ego, but it doesn't really do anything for our self-development.

DAN: But instead, taking a step back and saying, or asking ourselves, I wonder why that person would do that, and then trying to find the answer, is much more instructive. And oftentimes you end with the same opinion that you had before you started, but you know a lot more in the process. And those moments when your mind is changed, your opinion has changed, those tend to be, at least for me, the things that I learn in that process tend to be very impactful for how I behave in the future.

WENDY: Yeah, You're pointing to that skill of curiosity, being curious first. Be curious about why somebody came up with something and then you will have much less tendency to judge it because you've opened up your mind. I think that's a very big takeaway for everybody listening to this. Come at things with curiosity, understand people's why, and it's about your team. It's not just about you. And I love that you represent all those things, Dan.

WENDY: So thank you. I think this has been really helpful. I've learned a lot, as always. We had a webinar. If anybody else wants to look at the bettermanager.us website, you'll see the webinar that we did on sales, and Dan did such a great job. That's why we called him back to do a podcast and share some more wisdom. So thank you Dan so much for taking the time today.

DAN: Thanks, Wendy. It's my pleasure.

WENDY: Yeah, it was great. And to everybody out there, have a wonderful year. Take this on. Keep learning. And Dan, if anybody has questions for you, can they reach out to you if you're not on LinkedIn? Is there any other way for them to find you?

DAN: Well, I have a profile there. I just try not to go onto the site. Yeah, but you can email me directly. It's dan@buildzoom.com.

WENDY: Okay. Yeah, if you ever need people on your sales team, this is a great way to be able to intrigue them. I want to work for a man like this. Yeah. All right, good. Thank you, Dan. And we'll put some things in the show notes about the podcast names. And we look forward to seeing you all on the next podcast, and many thanks Dan.

DAN: All right, thank you.

WENDY: Have a great day everyone. Bye.

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