Episode 72: Navigating the Sales Leadership Problem, with Richard Harris

Hi everyone, I'm Ben Wright, successful entrepreneur, corporate leader and expert sales coach to some of the most talented people our amazing planet has to offer. You're listening to the Stronger Sales Team podcast where we bring together and simplify the complex world of B2B sales management to help the millions of sales managers worldwide build, motivate and keep together highly effective sales teams. Teams who grow revenue and make their businesses actual profits along the journey. We also provide great insights and actionable steps to managing your personal health. A happy and productive year is not only better for your teams, but everyone around you. So if you're an ambitious sales leader who wants to build the highest performing and engaged teams, stronger sales teams is right where you need to be. Welcome back to Stronger Sales Teams, the place where we provide real world and practical advice to help you develop super powered sales teams. Part 2 with Richard Harris is aboard today. We had such a good time, Richard, during part one that I wanted to spend a little bit more time picking that super experienced brain of yours and what's inside it. So, but before we do, I might give a quick introduction to you again to those who missed the episode a couple of weeks ago. So, Richard Harris, he is a world renowned sales trainer who has a very rich history of elevating sales teams across all forms of the sales spectrum. So for me, I really appreciated his invaluable insights around the seller's journey and the buyer's experience a couple of weeks ago. That for me really did resonate that he is without doubt a go to authority in sales training around the globe. Richard's got a great book that he calls the Seller's Journey, which is out on Hard Copy and coming out on Audible or audiobook soon. And also the proud author of the Neat Selling System. So for me, one of the things that I really like about Richard is the experience he has with some really big brands. Google, Visa, Zoom, Salesforce, Intercom, Doordash, Pandora, Pandadoc, just to name a few. Right there, some really big, heavy hitting, powerful brands in there that says to me, Richard's got some great experience in helping sales teams grow. But also, and perhaps more importantly for this type of medium, he is an experienced podcaster as well. So, Richard, welcome back to the strongest sales team podcast.

Thank you. Rarely does someone ask me back, I guess I didn't offend you enough, so I'll work better on that this episode.

Yeah, yeah. Well, it's hard to offend the unoffendable, but by all means, go for it as hard as you like. All right, we Spoke a couple of weeks ago about particularly around the seller's journey and the buyer's experience. But what I failed to do was ask you to share some of your background about what you do and why you're so successful. So let's not make that same mistake twice. And before we get into leadership that we're talking about today, can you please share with everyone your perhaps a brief snippet of your journey and what you do now?

Yeah, I mean, I've done everything right. I've been a sales rep inside, outside. I've been a sales manager, a sales director, VP of sales, head of sales ops. So I feel like I have a lot of experience around the different elements of revenue. Right. And that even moves tangentially into marketing because you have to work with them around messaging and, you know, finding that delicate balance between marketing messaging and sales messaging. Because we're all trying to sort of do the same thing, but it resonates differently. And then just through my own leadership experiences, I've been able to build and run teams, have been able to inherit teams, change culture, all those kind of things. And so, you know, I've made a lot of mistake. I got a lot of stuff right, but I made a lot of mistakes, too. And so altruistically, I like to share things to help others. Right. Like, if I can help someone else avoid a mistake, then I think that's kind of cool. So that's really why I like talking about all this stuff.

Excellent. Well, a perfect moment to start to introduce leadership. You've clearly had plenty of experience with it, but a real challenge that we're seeing across businesses today. And look, I wouldn't limit it to just today, but it's around sales leadership. And for me, I take a very simple approach. Often we take very successful sales people. So individual sales contributors who have been out there hitting quotas, chasing targets, doing great things for their customers, and been very, very good at their job as individuals, we then thrust them into a leadership role, often with little to no training, and said, you know what? You were really good at selling. You hit some fantastic numbers over the last years or decade. Let's give you a chance at leadership, and I'm sure you'll work it out. Right. We put them in there with very, very little support. And often that is the point where we see people or leaders hit that glass ceiling and really struggle to succeed in a very, very different role to what was selling as an individual. So what do you see as some of the issues around sales leadership today?

I don't think there's a ton of new ones. I mean, there's always something unique that's slightly different. But the biggest challenge I see around sales leadership is that so many of us still haven't been trained on how to be people leaders. Right? So many of us have. You know, we're really good at sales. We can close deals, we can negotiate. We probably helped with the interview process a little bit along the way as we got skilled up. Maybe we did a little bit of the training or the CRM training or whatever it is, and then we got thrust into leadership. And nowhere in there are the soft skills. Right? Nobody's taught you how to be a better interviewer as a leader. Nobody's taught you how to present a difficult situation. Nobody's taught you how to deliver a pip if you have to do that. Nobody's taught you how to fire somebody. Right. In an appropriate way. And so I think that's a lot of the stuff that's missing. And if you wrap that all up into one big thing, it's just soft skills. Nobody's taught you the soft skills. I once had a mentor tell me that, you know, the soft skills are the hard skills, right? I can manage a pipeline and people and tell people to bang out more phone calls or, you know, need them to work on their revenue, but nobody teaches you the soft skills. That's the biggest thing.

What I'm hearing is the soft skills are the hard skills to master. So the skills that we haven't had enough exposure to and time to, and we spoke a couple of weeks ago about pricing and negotiating around pricing as being a very difficult skill because we spend far less time on it than we do doing our demonstrations or our initial rapport building. Because naturally, our funnel allows us to do less pricing discussions because we lose customers along the journey. So let's take a macro approach here. If we have a leadership problem, particularly around the soft skills, how would you go about fixing that problem?

I'm all about use cases, whether it's sales training or management training, right? Like, I always try to ask, you know, the people I'm working with. Well, give me a scenario that you're struggling with. Give me this one scenario. Hey, someone ran out of vacation time and they're demanding they'd be allowed to take more vacation time, right? Or, you know, something like that, and then I'll walk them through. Well, how would you say it? What would it sound like if you tried it like this? So you can get super situational at a much bigger picture? What I really want people to understand is how, you know, we talked about this a couple of weeks ago, but how humans make decisions. What's the psychology, right? And understanding the mindset of the person you're talking to and understanding what's important to them and how to leverage this. Right. And do it in a way that's not manipulative, but that can find that way that helps you get your message across. Like, here's a perfect example similar, you know, from a leadership perspective. But, you know, if you're a head of sales, you've got to go fight for budget against head of marketing, head of IT, head of any other department, right? So how do you negotiate that without just sort of putting slamming your fist down and say, well, this is what I need, because we got to hit the number, and we got to do this, we got to do that. Right? So teaching people how to actually have that conversation means teaching them to think about, well, what's the CFO thinking about in terms of creating budget? What is my VP of marketing? What are their challenges? And at least understanding that so that as you formulate your conversation, you can try to drive to what you need and do it in a healthy way. And it's the same skill as if you're managing people, right? You're doing the same thing. One is you're managing up. The other is you're managing down. It's the same skill. Just, you know, you have to nuance it a little bit.

Yeah, right. Well, we're certainly talking about practice. I'm hearing that loud and clear that to get good at some of these softer skills, we need practice, but also perspective. So being able to understand what are the key drivers on the other end, right? Be it your team, be it your leaders. And essentially, they're skills that we need to have learned from dealing with buyers. It's a translation of those skills into or from what we were really good at as individual salespeople across into a different environment. One of the things that I often see leaders struggle with, particularly in the early days, is how they balance. Once they've got to that point of understanding what their team needs to do and they've got the resources they need, is how do they balance a level of accountability with also having some fun along the journey? Because they're certainly not mutually exclusive. Do you have a view on how they do that?

Yeah. So I think, you know, everybody loves to talk about, you have to set expectations, right? And you can't define expectations without also defining the accountability of it. So a lot of Times in sales, I think people, oh, here's your quota, here's your goal, that's the expectation. And then we just assume that accountability means you're going to lose your job, you're going to get fired. Right? That's sort of the outcome of it. But how do you teach them to be accountable? It's like, hey, here's your goals, Here are the proper metrics we're going to work on and that I'm paying attention to, right? Here are all the tools we're going to give you to be accountable. And then you have to ask your, you know, personally, your team member, you know, what helps you be accountable to yourself. Because I don't want to micromanage you. Ben likes to be held accountable differently than Sarah. Right. Then Rebecca than Richard. So we have to understand the motivation of each person because I think accountability goes hand in hand with motivation as well. You know, you can be a rah rah cheerleader, you know, go for it, go for it, close the deal, congratulations, blah, blah, blah. But that's not enough, right? And this kind of goes back to those soft skills and we have to ask people what helps them hold themselves accountable. Right. And how do we translate that in a way that they can create an accountability plan for themselves versus me telling them that every Friday I expect you to send me blah, blah, blah, blah, blah. Right? You can do that, but there needs to be more buy in on it. So that's a simple step in terms of, I think, teaching people to be accountable.

So this is really an extension of those softer skills that we're talking about earlier, the ones that are harder to master.

Right?

That extending them not only to your leaders and to your team when you're understanding what your goals are or what you need to achieve, but also about how they can best operate in an environment of accountability. And to break that down even further, we've got a level of accountability that can be driven at a team level. So things like, hey, we turn up to meetings on time, you know, we put videos on when we're on video calls. And then there's a level of accountability that needs to be done at an individual level, which are gonna more specifically relate to your individual tasks that you need to get done. So. Okay, great. So what about layering some fun into that? Because accountability, that's boring and mundane and is no fun.

Yeah, I wanna come back to that. But I wanna bring up a couple other things that sort of entered my head. When you think about accountability, I think you start that conversation in the Interview process, Right. Hey, if you come on board, you're in sales, you know, how do you hold yourself accountable? How do you like to be held accountable?

Right.

What kind of management style brings out the best in you? What do you need from a leader to help you maintain and achieve your goals? So things like that can be asked in an interview process around accountability. I really wanted to point that out. And then the other thing I encourage people to think about is what motivates to ask is, you know, how do you commit yourself to being accountable? Not just how do you hold yourself accountable, but what's that commitment like for you? Like what did you have to do? How do you. So you're going to work hard? Okay, well, what's that mean? Right. So how are you going to commit to it? What are you going to do if you're behind and you still want to hold yourself accountable? So there's a lot of stuff around that. I'm going to put that to the side now because I want to come back to your question. You're right. They can't just all be, you know, the beatings will continue until morale improves. Right. Like you can't manage and lead that way. That's by the way, that's not a good leadership style. Speaking of leadership, so. Absolutely. Building fun. Yes. There's gamesmanship in there, there's leaderboards, there's spiffs, there's contests. What I try to do, that's not different. But I always try to reward more than one person. Right. So if I create a game, I will tie a team number to it as well. Hey, if everybody does this, everybody gets this. By the way, the top three people who do this get this. Right? So that even if someone can't be one of the top three, there's still an option for someone to get something at the end of it.

Right.

To participate as a team. Right. So depending on what the contest is, I think that's a fun way to do it. I've done everything from bingo cards, you know, around sales skills and you know, everybody who gets a bingo gets, you know, a five dollar Starbucks card. Anybody who does all four corners of the bingo, and I make the four corners harder things, you know, they get a ten dollar Starbucks card. Anybody who creates the X through bingo gets this. So now there's individual attainment, but everybody has an opportunity. And then I might say, oh, by the way, you know, the first person to get a blackout gets, you know, 200 bucks. Right. So you can build it in lots of different ways. I've done stuff like that. I've done auctions. I've done stuff where, you know, they get funny money, you know, with the leader's face on it. And then at the end there's all these things they can purchase, you know, at the end of the quarter, anything from, you know, airplane vouchers to hotel vouchers to a TV to, you know, cell phone or just all kinds of little stuff, then all has to be super expensive, right? So those are fun ways to do it. There's a ton of ways to do contests. That's like, again, it's got to be the right company and the right culture. But, you know, the top three people get to go have a nice dinner with the CEO, right? Like a steakhouse or something, you know, that's, you know, if you're a vegetarian, obviously you need to make sure there's something available or gluten free. But you know, making something, it doesn't always have to be a prize. That's physical. You know, if I'm in sales and I'm at a bigger company and I could get dinner with my CEO, right. Even if you're just a 50 or 100 person company, I mean, what could that do for my career, right. To have dinner with my CEO so I can get to know them. Those are fun contests in my mind, in my opinion. So anyway, those are. I'll shut up now, but those are my thoughts.

It's interesting when we talk about having fun, you focus very much on gaming side of it, right? So we're having contests to get us to celebrations. But a theme that came quite clearly through that is that accountability isn't just at an individual level, it's also at a team level. And when we're trying to roll in fun as a sales leader, it's important to have a perspective around or a lens around both the team and the individual. And that's almost the way that sales people have been incentivized for decades. Partly around teams and partly around individual. But when we're talking about fun, I think it's a very interesting perspective to say it's not either or it's not fun as a team or fun as an individual, but perhaps it's a balance of both that allows your teams to get the most out of that accountability requirements that they have from you as their leader. Great insight. Thank you. So let's imagine right now that you're a sales leader who's come into the role. Let's say you're your newish right in your first few years in a sales leadership role or your first few years in a new company or your first period in a restructure. Right. We're talking about early stages of whether it be tenure or other business or business type of business lifecycle. And you're needing to build out a team that has a culture of accountability, has a culture of fun whilst you're out trying to achieve those goals. Where would you be recommending a sales leader starts and focuses on in their first six months?

If they have a strong accountability culture, that's one thing. If they haven't had one, which is usually why you're a new sales leader, it's going to take a slightly different approach. They're similar but slightly different. So the first thing regardless is obviously spending time with the team, right? Both as a team and both one on one. So I would certainly do one on ones as soon as possible. Try to get to know them a little bit, make sure they understand you. I know it's super cheesy and boring. I think it's important for them to equally know about you. So I'm not opposed to, hey everybody, like this is my resume, right? You can always ask me anything. Here's a couple of personal things about me, here's some pictures of my kids, whatever, right? There's nothing wrong with finding a way to do that. Some leaders, you know, find a way to put it in a PowerPoint and be a little self deprecating so it doesn't look like you're, you know, just being overly obnoxious and self centered. You can include things like, you know, this is how my style's been described by other people. I've managed. This is what I've learned. Here are some mistakes I've made in leadership that I'll never make again. Like, you can be super vulnerable and share that and equally get to know them about what motivates them in their personal life and stuff like that. I think it's super important to do that and I think it's important to do it early. I think it's great. As soon as you can do something with the team within the first week or two, whether you take them to dinner, you take them to lunch and let them know that this is, you know, this is just about us like hanging out and get to, you know, for me to get to know y' all a little bit more, have a little bit of fun, like, you know, just sort of set the tone, right? So I think the first thing is how do I set the right tone? And that's the first step, the other piece is to understand, you know, what's one thing we can do better? And so when you ask somebody, hey, what could we do better? What could we work on? It's such a big question. It's so big and it's hard to grasp at those straws. If I ask each person on my team individually, what's one thing we could do better to improve the culture here a person can usually find one thing and I try to actually ask that separately than like in a big team. Reply all email. Because I don't want people to go, yeah, I agree. I want people to come up with their own thoughts and generally speaking, a lot of them be the same, you know, oh, we need a better commission plan. Okay, well we can look into that, you know, but I want to learn about one thing from each of them. So those are a couple of ways to start at some point, depending if the culture of the team is toxic or not enough accountability. Yeah, I've been known to fire someone pretty quick and I didn't care if they were the top salesperson. Right. There's a lot of thought that goes into that. There's a lot of Hrness, you know, legal issues and all that stuff. And people get really nervous. Well, I have to fire my top rep. What am I going to do? Well, you know what you're going to do. You're going to have rep number two and number three battling it out to be number one. Right. So there's a lot of positive to that. And again, I'm not saying this in an inhumane way. Like I realize like that person needs to be fair, pretty toxic to get rid of them. But you know, if they can't be held accountable for business appropriate things in addition to their revenue, then you've got a bad culture. In my opinion, it's not always about the top rep.

So we got three things there. Invest the time in getting to know them and let them get to know you. Find out ways you can improve, but keep it at that very top line level. Giving you number one and number three is cleanse the team from toxicity if you need to. Okay, so just quickly, if we can very briefly touch on how would that change if you were building a new team?

So in a lot of ways building a new team is a whole lot easier. It takes more time, but you get to build it from the ground up. Right. And if you're building a new team, I always found it interesting that the new team members would always try to help me with something. Right. Like hey, this is your job. Come in and do your job. You know, by the way, I've got these other little projects. If, you know, if you ever have time and you're doing well, let me know. I'm happy to have you help. Right. Whether it's interviewing or setting up a process or, you know, saying, hey, here is my sales process that I think we should be using. What do you think? What's wrong with this sales process? So that's the first thing I think. If I'm building a new team and I have client and customer calls, I want that rep, you know, shadowing me a lot. Right. Even if it's an sdr, even if it's a sales call, and I've got hired a couple of SDRs, and they're just prospecting. I want them to hear those conversations because that's teaching this culture of authenticity, teamwork, that I care, right. Like, as a leader, I care about their development because I think that's a really important thing when you build a new team. Yes, people want jobs, but they also care about career development. And there's a unique opportunity when you're building from scratch to do that differently than if you are hiring people when you've already got eight or ten sales.

Reps. Yeah, okay, got it. So essentially what we're talking about is the same. Same. But where we're investing our time is more heavily around training, building up the ways of working that we as a team stand for. Excellent. Love it. So, as always, Richard, nice and punchy. Some really practical stuff in there that particularly new leaders, new to it, business leaders or new business life cycles. So restructures in businesses should be able to really lean on around how they can develop their teams and particularly some of their leadership skills. Richard, for those who'd like to know a little bit more about you, where can they find you?

Yeah, yeah. So you know me like, you know, yes, I'm on WhatsApp, but it's +1415, 5969. 149-415-5969. Text me ahead of time to tell me that you heard me on stronger sales teams. If you want to call me. But I'll gladly answer people's questions, give advice, whatever it is. You can also find me on LinkedIn Richard Harris with the little trademark emoji and finally, shameless plug of my book the Seller's Journey, which is out on Amazon and all those other places. So gotta do that. But thank you for having me on. It's been a great second conversation with you man. I really enjoy it.

My pleasure. Thank you Richard. And for everyone listening, please keep living in a world of possibility and you'll be amazed by what you can achieve. Bye for now. Want to be kept up to date with any of our free materials to help you build the best sales teams possible? Well, the easiest way you can do so is to follow us on your favourite social media channel. We're stronger sales on most of them and if you DM us stronger we'll send you right back some great resources to help you build your super powered sales team. If you'd like a little more help, please get in touch directly and book a free discovery call with me. I run a limited number of these sessions and they're free for my podcast listeners. I'd love to help you out. Until then, see you next week for another podcast of stronger sales team.