E2: How to Lead 100% of the Sales Team to 100% of Quota with Mike Wingfield | Sales Director New Relic, Twilio & Deel

Welcome to the Switch Gears podcast. I'm your host, Priy Saka, and I'm thrilled to have Mike Wingfield join me today. Mike, welcome to the show.

Thanks, Priy. Thanks for having me on.

I've had the privilege of knowing Mike for a number of years, and I know him as someone who's a high-performance sales leader. He has worked with scale-up companies like Marketo, New Relic, Twilio. And he has a distinction because he is part of the 100x100 Club. And that is he got 100% of his team to 100% quota, not once. So we know it's not a fluke, but twice. And knowing him, I think it's going to be a pattern that he can repeat over and over again. So I want to get to know today how he does it. And we're going to jump right into the details. So Mike, thank you again for sharing.

Thank you very much, Priyank. Appreciate you having me on. It's something I'm excited about sharing.

All right, so tell me a little bit more about the 100x100 Club. You've done it with 2 terrific companies in scale-up modes. If I was a sales manager who was in a new role or new to sales management, what are some of the things that I need to do to set my team up for that kind of success?

Yeah, it's interesting that the 100x100 Club, I didn't realize was as important as it is until we had a celebration offsite at the end of the quarter where I had my leader pop his hand around me and say, this is what the end of quarter celebration or the end of year celebration feels like when everyone hits their number. Feel that, bottle that. And I was like, okay.

Nice.

For others that are looking to do it, You gotta be relentless on hiring. You cannot get to that sort of an achievement without the right team. And I think when you go through the recruiting process, building a team, you just can't settle. You have to source top talent. And I'll dig more into hiring traits, but build a world-class team is my responsibility. And then I've gotta create an environment for them to be successful, and I'm gonna coach them to be successful. And then as a leader, it's my responsibility to remove the barriers that are in their way. And support them to be successful. If I'm going to repeat the process, spend a lot of time with sales operations. Sales operations tend to get sick of seeing me because I'm relentless in how I build my territories and making sure that, is it achievable? Can we actually build a 100/100 team if we have fair and equitable territories? Relentless on top talent, and then create a culture of learning. I find if people can learn from each other and coach each other and help inspire others to lift up, It sorts itself out and then celebrate the wins along the way, the little wins especially. I'm a pageant mum as a sales leader. Anytime we do a little win, I'm thrusting people into the limelight. Tell people what you've done, share that.

Yes, that's so good, Mike. I'm a firm believer that little wins lead to big wins. So it's really important to actually recognize on a daily basis whether it's a great Cold call or a response to a creative message. Or so tell me, what are the little wins that you look for and encourage team members to share?

I'm as lame as I'll clap when someone has a bad call. Don't worry about it. Well done. This person just told you to stuff up. No, but the little wins along the way, uh, if you have a call that goes well, really break down what went well on there, especially anytime someone demonstrates Or demonstrates brilliance at the basics. If you set a really clear agenda, I'll celebrate even those wins. Like, hey, that was a really well-structured call. You came really prepared. Did you hear how the customer responded? To then even slightly bigger wins. Like, we're just pacing well on our monthly number. We're on track with these key 5 deals. We know the decision-making criteria. We know the proof of value required.

Yeah.

Any chance to celebrate wins, I'll do that because then we just stay motivated.

That's fantastic. So tell me, in terms of building a world-class team as a sales leader, what should your first 90 days look like?

I want to review the previous 2 employee survey feedbacks for my region, assuming I've got access to that. They tend to tell you a pretty clear picture on how the environment is currently. Use the sales operations team again to review how we're pacing against our goals. Then the third one is listen. I've gotta listen and connect with the team and really find out how are we differing or how are we going against our trajectory of where we should be. I'll watch calls. I'll spend a lot of time watching calls and observing. I'm not gonna have a lot of input. I'll jump on calls with sales reps, but really I'm just there to observe. And then Reflect my observations back to the team, I think, is probably a big one. There's nothing worse than a sales leader coming in and observing a lot of stuff, and then they don't communicate what their plan is or what their observations at least are to the team. So I think that's a big trait for me. And then I've got to reflect my observations back to the team and start building a plan. And I think getting everyone on board with that plan is easier said than done, but that's a priority.

Let's go micro for a second and tactical. Tell me, how do you give feedback? I'll come back to this a little, a little later on coaching, but just give me a sense of— you've observed some calls and you're going to have people who exceed expectations, who are below expectations. Give me a nugget on how do you give feedback.

I look at feedback in the 3 ways, right? So there's 3 areas I'm focused on. I'm very clear with people how I give feedback, right? Behavior is the number one thing I'm looking at. The number 2 thing is effort, right? How are you representing the firm in terms of pipeline generation, the high-value activities required to achieve your number? And the 3rd one is results. And results should be a lagging indicator of your performance in the first 2 categories. So the way I give feedback is very much Here's what exceptional is, and I'll celebrate the exceptional indicators. If you're exceptional in your behavior or you're exceptional in your effort or you're exceptional in your results, I'll start sharing that with people. I find out how people like to be recognized as well, 'cause some people don't like to be publicly praised.

Yeah.

So I'll make sure that I understand that. And then acceptable, you shouldn't hear from me. If what you're doing is acceptable, we're probably not gonna talk about it unless you ask me. When it comes to unacceptable, I should be catching you On the way down to acceptable. It's hard to do that with behavior, but really I should be pulling you aside and saying, hey, what you're doing right now is heading towards unacceptable. And instead of pointing people back to what acceptable looks like, I'm actually going to point them back to exceptional. Here's demonstrations of exceptional performance. Here's exceptional behavior. This is what this individual does and why they're doing well here. So, yeah. Behavior, effort, results. Acceptable, exceptional, unacceptable. I try and keep it as simple as possible.

That's really good. Thank you. So moving on from that, Mike, so we've talked about the first 90 days. Tell me a little bit about how do you hire and what are the top traits that you look for? Tell me a little bit more about hiring.

Yeah, I try and cheat a little bit on hiring. And what I mean by cheating, I'm big on references. And references, I think, especially these days when Firms are offering these big incentives to referring your friends and all that sort of stuff when they're multiple thousand-dollar payments. That's hard. But my question is, can I get a genuine reference on this individual from someone whose opinion I truly value? Is it someone that's prepared to put their brand on the line and say, hey, this individual's a hitter? That's part one. That's, that's the shortest path to success for me. If I can get a genuine, solid Reputational reference, great. Then what I'm looking for is, is this person driven? Are they self-motivated? I can't train drive. I've tried, Priya, but I cannot wind someone else up. And I always say to my reps, I can't want you to be more successful than you wanna be. So they have to be self-motivated.

Totally.

You can spot a rep who's prepared and curious and asks lots of questions. I really like it when someone comes with almost an imbalance of questions for me. But they're thoughtful questions about how am I gonna be successful? Not just someone who's turning up with questions saying, what's my territory gonna be? And have you built that today? And how do you go about leading people? I want really specific questions about how am I gonna be successful? What are the traits of other performers in your team that are doing well, et cetera? The most important thing I'd say once we're in the interview process, I'll start asking myself at about 3/4 of the way through, does this person make the easy things Seem easy. And it's a weird thing in sales when you're going through a, let's say it's a mock discovery call. I know I've got it right when the person that I'm running the mock discovery call with, I usually get one of my team members to help me on the mock discovery calls. And at the end they'll say, oh, you are a bit easy on them. No, that's actually their sales skills shining through, right? I don't wanna make a discovery call difficult, nor do customers. They're not there trying to make the buying process difficult, but you as a sales rep can make it difficult. So do they make the easy things seem easy? Do the conversations feel easy, that the people that come back and give feedback on them go, it was a nice conversation, I really enjoyed the time, it just felt easy, felt natural. And then I like people that are proactive, resourceful, and play well with others. And that kind of goes back to my culture of learning. So driven and self-motivated, prepared and curious, they make the easy things seem easy, and are they proactive, resourceful, and can they play well with others?

That's great. That is very useful. Then when we look beyond the first 90 days, what are some of the other things that you need to start architecting in place to build towards that 100 by 100 year?

This is where I spend a lot of energy in crafting the vision. I think really making sure that you've set your team goals clearly and then gotten buy-in from the team, right? So what does a great year for you look like? What do you really want to achieve? I'm always asking my reps to aim for beyond their target. If you're hitting 100%, congratulations, that's acceptable, but shoot for exceptional. And then if you fall a little bit short— and I've had reps at the end of the year with their heads in their hands like, I only hit 110%— cool, great problem to have. I'm really setting out the vision, and then we're reinforcing that along the way. How are we tracking? How are we pacing? You've got to keep the team updated. And I found This is a trait of mine. When I'm not sharing a lot about the numbers, that's probably not a good sign. When I'm talking about the numbers a lot, how we're pacing, how we're tracking, and even just those little wins, that's usually a good indicator that we're on track. So yeah, be really transparent with the team, share the vision, make sure that there's a common goal, and yeah, just keep celebrating those wins along the way. I think that's the reinforcement of we're on track, we're doing well, here's our gap. People really get behind it.

That's really useful. What happens when you're now at the 6-month mark and you are starting to notice that things are not going according to plan? Right?

Yeah.

And let's start with factors under your roof. So you've got 1 or 2 team members who have missed quota. Their pipeline isn't where it's supposed to be, and potentially activity is below where it's supposed to be. This is the pre-PiP conversation. How do you manage performance?

Again, I think the earlier you catch underperformance, the better. And it's a hard conversation to have, but I think that's our responsibility as leaders, is to give clear feedback. Hey, the way you're trending right now is on the path to unacceptable. And there's leading indicators, right? So, that's why when I talk about behavior and effort, if I'm consistently giving feedback during one-on-ones, hey, I've observed this, and if I— how do you feel you're going there? Here's my reflection, right? I think a level of self-awareness is important there because you'll start spotting if people are trending down, but they're telling you they're still shooting for the roof, you've got to address that gap first. So, making sure that people are aware that there's a gap. Putting in a coaching plan, so I'm always running coaching plans, and I try and avoid a pip with a coaching plan first. And it's something that a rep won't see. I'm not necessarily running a formal hey, you are now on a coaching plan, but it's very much of just scale things back to the basics. Hey, what's within our control? Pipeline's going to solve all problems in sales. So we've got a pipeline issue nine times out of ten if we're trending under, or we might even have a. Getting high on hope problem. There's some sales reps that have these huge pipelines. They love the fluffy pipeline, but they're not killing deals that aren't deals. So I think it's a bit of a reality check. Go back to the basics. Pipeline, clean pipeline solves all problems. And then I'll be out on the field with them making sure that we can close that gap. They'll probably get a little bit more of my attention and my support in that period. And then again, it's just back to celebrating the little wins along the way. I will go down to the very specifics of what's working well. Right. That discovery call was structured in a way that's a winning outcome. Did you see how those next steps got us to the next stage and how we're now at a real clear qualified process? What you now have in is commit. That's a real clear deal. Do you understand why? Yeah. Fantastic. Yeah. It's usually when someone's either not putting in the effort or they're high on hope.

So tell me a little bit more around your coaching plan. How do you set up a coaching plan? How long does it last? What are some of the outcomes that you've seen from it?

Coaching plan for me is a last resort, right? Like, as a PIP, I'm really reflecting back on my last however long I spent with this AE thinking, where did I go wrong? Was it hiring? If I wasn't the person who was directly in charge of hiring this individual, were there signs that we missed or red flags that we've missed along the way? Is the person in the right role? I've had some people where their behavior and their effort is phenomenal, but the results just haven't been there. And then I've made an adjustment to their role or their responsibilities and off they go. And that's happened a number of times. So it's really making sure they're in the right role. So then we get to a point where there's a plan, a real written plan. This is a tough one for some reps to hear, but like 90% of pips, you're not going to make it. It's a pathway to the door. The questions I've got to ask myself in that process is, do I really want to see this person succeed and survive this performance plan? Do I have the faith that they can survive it? And if that's all in place, then the plan that I'm putting in is all about brilliance at the basics. I'm giving really clear pipeline indicators. It's really hard to transform someone's results while I'm saying you're on a coaching plan and your job's on the line, but I'm looking for leading indicators. So more often than not, my performance improvement plans are about pipeline generation and quality pipeline generation. Now, again, I'm usually by this point done coaching plans and things like that. I'm also having a conversation with that person saying, hey, how do you feel? Do you think this is achievable? What can I do to help? I'll even go as far as making sure that people are interviewing with other organizations.

Like, Right.

As a sales rep, if you've got a job to fall back on, it's really hard to sell when you've got a gun to your head. I'm encouraging them to just make sure that they've got the mental climate to feel that they can be successful. And I feel if sales reps survive a PIP, those that do, it's usually the ones that come out and do beyond acceptable. They do something that's exceptional. They put in the real effort. They go hyper-curious. They double down on effort. They build the right kind of pipeline. But it was rare pre. Not a lot of reps survive PIPs. So yeah, it's a pretty structured process. It's all about pipeline. It's all about behavior and the results usually flow from it, but not a lot.

Fantastic. That's what my, my data tells me as well, that a large number of PIPs don't work out. And I really like the fact that you said you have a coaching plan before you get to PIPs and PIPs are the last resort where you've got to formally manage it. Right. I think that's the responsible thing to do.

We are responsible for their careers. So it's important.

That's brilliant. So if I was a new sales rep on your team, what are some of the things that you would have me work on to get ramped up in the first 90 days? Sure.

The first 30 days with a rep for me is actually as important as the first 90 days, right? The first 30 days, I want them to go out and be resourceful. I usually give people a list of team members I want them to connect with. There's nothing worse than when product says you have to come and learn our product back to front in the first 30 days. I actually dial that back and I say no. And when you go and learn the environment, learn from the people, the first 90 days are about showing your resourcefulness, showing that you can go and source information. And then I learned this as a kid, I learn more when I'm coaching other people and I'm teaching other people. So I'll ask people, hey, what did you learn today? Talk me through what you learned and I'll ask questions. How did that go for you? And how do you hear that working? And then you can hear the cogs going, oh yeah, the platform does this and that person's responsible for that. And I learned from such and such that they can help me move my deals here and deals should be structured that way, whatever they're learning. So it's all about the first 30 days about being resourceful and making connections and building relationships. Because once you then pivot into your territory, if you will, all the people that can help you, you can move a lot faster. I'll usually say, people, meet the people, then go and learn the product, go get up to speed on that. And you play back what you've learned to me and I'll correct you along the way. Then you'll start doing, practicing your pitch. So I'll spend a lot of time with people practicing their pitch, and then we'll focus on their patch, giving them their territory, walking them through it. And then we go out and we perform together. The back end of that 90 days is really about, let's get out there. We've practiced our pitch together. You're feeling pretty comfortable. We've had a couple of practice discovery calls. I'm happy, you're happy, let's get out there and perform. And those that are proactive through that process as well— hey Mike, I've booked meetings, I've met with these 5 top customers— I love that. When someone's saying to me in their first 90 days, what should I be doing next? Okay, all right, come follow me. Yeah, I like people who are proactive and resourceful.

Yeah, I've been a sales leader for 7 years. with Fortune 100 company. And one of the things I used to tell reps every single time was that I don't care if you're a Ferrari, if you don't have any fuel, we aren't going anywhere, right? It's your job to bring a full tank.

Yeah.

Right? So when you said earlier, it's very hard to motivate people because motivation really is internal. You either need to have things you want to prove, things you want to achieve, things you want to get done in your life. If you do not have that, tells very quickly who you are and what you end up doing.

100%.

That has been such a good specific dive, step by step. Tell me, before we wrap up, what are some tips that you have from creating and sustaining a winning culture? So now you've hired good people, you've gotten them through the first 90 days, You've gotten people firing on all cylinders, they're building pipe, they're closing deals, you're coaching them, giving them feedback. What advice do you have for that second half of the year, the next 6 months, to ensure that you manage it to reach that desired outcome?

Now I'm looking at this through the lens of a technology sales Leader, right? You have to consistently make sure that the data is indicating that the perception is right. That's where I think that's one of the most important things. Aim that relentlessness on creating that culture of learning. If people are kind, compassionate, and empathetic to one another in a sales environment, then it creates a default of it's okay to share with one another. We're not just competing. By all means, I enjoy a competitive culture. But we've gotta make sure that people are, hey, let me help you with that. Actually, I've had the same circumstance. Let me show you how I got through that. Let me show you how to process that order. Let me help you with that legal form. And what you find then is you'll have Slack channels or Teams channels that are just filled with questions and other sales reps are actually self-healing and self-supporting and self-serving each other because then it means that I can focus on clearing the runway, right? So along the way, what I'm making sure is that the team's focused on learning from one another. They're focused on the goals. We're celebrating the wins along the way, but there's an environment where people start loving their Mondays. And I've walked into a sales environment where culture's not been great, and the sales director that I was working with at the time, he said the easiest way to fix culture in a sales environment is get people selling. And he was bang on. As soon as people started selling, it's amazing how the survey feedback start going through, and it starts with creating a culture of learning, in my opinion. So maintain that. Tell people what they're doing right more so than you're telling people what's not working, and the momentum will go from there. Hope that answers your question.

Oh, it does, Mike. You've given me a masterclass on how to—

I wish—

set up on— set up for a great year. I think that you've given me a really good overview. So thank you today. It's been terrific having you on the show, and Until next time.

Thanks, Pri. Appreciate you having me.