Episode 31
Building a Coaching Culture in Sales
Summary
In this insightful episode, we explore the nuances of sales management development with Wesleyne Whitaker, an experienced leader in empowering sales managers to excel. Wesleyne offers a deep dive into how companies can shape their frontline sales leadership for lasting success and foster a robust, accountable sales culture.
Wesleyne stresses the importance of investing in the development of sales managers and identifies common struggles that companies face, such as inconsistency in leadership quality. She elaborates on the necessity of creating individualized coaching plans, drawing from open and honest conversations with the managers themselves. Emphasizing a mindset shift from solely hitting numbers to nurturing personnel growth, Wesleyne illustrates how these plans guide managers to become more effective leaders.
Key insights gleaned from the episode include strategies to transition sales reps to managerial roles, identifying skill gaps, and the importance of managerial self-awareness. Wesleyne provides valuable tips on coaching versus giving feedback, detailing how a true coaching culture benefits both sales teams and their leaders for long-term growth.
Take Aways
- Developing sales managers requires individual coaching plans, based on honest discussions about skill-gaps and management challenges.
- An effective sales manager must transition from a focus on personal goals to fostering team goals and success.
- A coaching culture within an organization drives managers to ask strategic questions, guiding reps to identify and overcome their own performance gaps.
- Feedback is telling someone what they did wrong or right, whereas coaching involves a dialogue that leads to self-identified improvements.
- Sustaining long-term sales success and skill development necessitates balancing a focus on immediate and future quarters.
Learn More: https://www.yardstick.team/
Connect with Lucas Price: linkedin.com/in/lucasprice1
Connect with Dr. Jim: linkedin.com/in/drjimk
Connect with Wesleyne: linkedin.com/in/wesleyne or https://transformedsales.us/
Mentioned in this episode:
BEST Outro
BEST Intro
Transcript
To your sales managers to help them excel at leading your sales team. Wesleyan has important insights to share with us about the importance of enabling those frontline leaders to succeed. Wesleyan is a dynamic professional with over 20 years of experience working with global corporations, combining scientific knowledge with behavioral based strategies to empower sales teams to excel.
She is known for her expertise in sales coaching techniques. and building sales enablement cultures. Wesleyan empowers high performing teams and resolves customer challenges through problem centric training. Wesleyan, thank you for joining us. What else should our audience know about you?
as a chemist working in the [:Lucas Price: I love that. I can see how that would give you insights that other people might miss that little bit of different kind of training that most of us don't have.
Wesleyne Greer: It's really helped me throughout my career. And when I first stepped into sales, I stepped into working in very technical environments. So most of my colleagues actually had technical degrees. There were engineers, there were chemists, they were geologists. So I thought it was normal.
And then when I moved outside of the world of chemical sales and really stepped into this place of entrepreneurship, I realized how different it is to have this technical background,
Lucas Price: yeah, that's great. I'd like to start off by getting into the topic of investing in the development of sales managers. Many companies struggle with inconsistent quality across their frontline leadership. What are the reasons for that?
ad, when it's down and we're [:Let's get everybody training on negotiation or how to do better discovery meetings. And so they push all of that down into really blaming the reps. for their lack of knowledge, lack of training and the managers get to take a backseat and say yeah, we should do that. Let's do that.
But what's happening is these managers don't have the core skills that they need to actually hold a team accountable. And even when you train sales people, the managers sit at the back of the room and they're like, ah, yeah, I've already learned this. I've already done this. They don't absorb the new information.
ho are actually touching the [:Lucas Price: So if an organization is thinking, I want my sales managers to become better, I want them to upskill, I want them to become better leaders and better coaches. What are the first things that they should be thinking about in terms of how to do that?
Wesleyne Greer: So when you think about, okay, I have never invested in any kind of training or development for my sales leaders and I realized they need something. One of the first things that you should do is sit down and have. Open and honest conversations with them and ask them, what are the skills? What are the things that you feel that you're missing as a manager?
And by opening it up and allowing them to just flow and say I don't know how to do this. I'm very uncomfortable here. I feel very insecure with this, or this doesn't make sense to me. What you're doing is you are. Able to develop an individualized coaching and development plan for those managers.
[:Lucas Price: Yeah, I love that. I think there's two things that come to mind with that. One of them is, I think in a lot of companies, managers won't be eager to say, this is what I'm uncomfortable with. And I guess maybe I'll combine them together.
I think like one of the things I realized at some point in my career, maybe it took me a little bit to realize this is that, my boss is going to be more comfortable with me as a, an employee. If I tell him the things that I'm struggling with instead of hiding the things that I'm struggling with, and so one of the things I'd like try to let everybody know is Hey, if you are always telling your boss, everything's great.
sing what, where you need to [:I think Brene Brown says I think like having that vulnerability is a way to get your management team. To start talking about, yeah, that these are things that I'm struggling with too. Any other advice that you'd have on that topic?
Wesleyne Greer: You hit the nail right on the head when you open up and you share your stories of how you struggled. So anytime I kick off a training, anytime I am working with a team, I literally start and I tell them, I'm like, So when I first became a sales manager in the first six months, we weren't hitting our numbers.
rk. And so it took one brave [:What do you mean? And really for me to look at myself and be introspective and realize that. My job was no longer to be the amazing person. My job was to teach everyone else how to be their own form of amazing. And so when I tell that story in a training, literally, I kick the training off. It brings everybody's anxiety.
It brings everybody's barriers that they have that are all the way up here completely down. Because they're like, Oh, she's human. And she gets it. And so when you're in that conversation as a leader, as a CEO, as really the person at the top, you have to show that I've had moments where I wasn't the greatest.
undation to have an open and [:Lucas Price: Yeah. A lot of times sales managers are promoted account executives or salespeople. And so if you're, and I think it's like a really healthy culture to have, I would say a mix. of outside sales managers and promoted sales managers. You want to show your account executives you have a career path.
You want to, the knowledge the internal knowledge that they gain as account executives, you want to keep that within your organization and not just bring people in from the outside. And I think having I think promoting internally is really healthy for the culture. But when someone is a new sales manager, they haven't done the job before.
What are some of the things that they might, they might've seen someone do it and so they think they know how to do the job, but they actually don't, what are some of the shortcomings that someone promoted from sales might have that they would. They would particularly need help with.
but typically a salesperson [:It's no longer about your goals. It's no longer about what you need to do or what you need to accomplish. And so that's a mindset shift. And I really think that being an effective manager is pretty, it's probably like 80 percent mindset and 20 percent skillset. So once you are under that Under the veil of, okay, I have to shift the way that I think about everything.
I can't just go in and close this deal for my rep. I can't just do the work for them. I can't just always be there because then one, I'm going to burn myself out. And two, I'm never going to really grow this organization that has self sufficient people. So what a new sales managers should do, and I actually teach this to salespeople too when you get into your job, the first.
days is all [:Ask them lots of questions. It's literally like doing a discovery with a customer. You're doing a discovery with your salespeople so you can learn about them. And as they're telling you the things that are important to them, you're hearing them in the interactions with their actual customers. You should be developing your playbook of the areas that need to be developed within that person.
The things that you feel are still gaps for you that you don't really know. So you can invest in training and development for yourself.
you're put into a different [:Now you're a manager. And and I think like one of the things we know is that the best managers. Let's call them servant leaders. They put their team above themselves, but sometimes there are people, and I don't think it's necessarily a fatal flaw in the person as much as them not understanding what the transition means.
Sometimes you give that person, that salesperson a little bit of authority. Now you're a sales manager and and instead of seeing themselves as a servant, they see themselves as a boss. And they start to abuse it in the wrong ways. Maybe that's a little bit of a version of the journey you went through when you first became a sales manager.
How do you help a sales manager? See, what the right way for them to to be is in that role and how, the ego can get in the way and cause them problems instead of helping them.
leader of my own team and my [:And if you put yourself in that mindset of how can I serve, how not, how can I be served now? What can I do? It helps you even ask those questions. And so sometimes I literally will send a message to my, somebody on my team. And I'm like, good morning. How can I serve you today? And initially they're like, this is very weird.
Nobody asked me a question like this. Am I about to get fired? What is happening? And it's I'm like, no, because I know as a leader, my job is here because you're out there in the field selling, you're out there spending nights away from your family. You're doing the hard work because as a manager, I don't have to do those things anymore.
And so I want to show that I value you and I want to help you. And so it's a mindset shift. in how you show up, the things that you say to your team that gets you from that big ego, that dictatorship to really into that servant leadership mindset.
think of like organizations [:Wesleyne Greer: First, if you really want to develop your managers, you got to start with data. There are lots of different tools. There are lots of assessments and evaluations that you can use out there to assess the health of your managers, the health of your organization. And you really want to understand how effective are my current managers.
And you want to know how effective they are and based on their effectiveness, how long is it going to take me to get them to the level where they can be 100 percent self sufficient? So that's the first thing that you do. And once you have the data, you understand the areas. That they need to work on.
ms together because a lot of [:So they're just doing what worked for them. And so giving them the really good fundamentals so that they can then. impact their team and hold them accountable is really important. And you also need to work on the soft skills of the managers. So it's the tactical, how do you sell? How do you manage? How do you do one on ones?
And it's also the, how do you develop empathy? How do you have difficult conversations? And all of those things are really what organizations need to do to get their managers from where they are to where they need to go.
Lucas Price: Maybe you can clarify one thing for me. So you talked about an individual coaching plan. As you get that data, you're probably going to see certain trends across your organization. These are, 80 percent of our people need help with this one particular topic or 30 percent need help with this other topic.
So how do you think about like groups versus individual in that situation?
managers. [:And depending on the size of the organization, you have anywhere from two to maybe four, five groups. And It's not about tenure. It's not about geography. It's not about any of those things. It's about skill sets. So if I have a group of leaders that have probably 60 or 70 percent of their, what I call their sales management DNA, they're above a 70%, I'm putting all of them together because that means that there are very few things that needs to be tweaked.
If I have another group of managers that have about 30 percent of their sales management DNA, I need them to be grouped together because what happens when you have really strong managers and you put them with really weak managers, the weak managers never really get what they need because they're scared.
y, I can't ask that question.[:Lucas Price: As a company is thinking about investing into sales management development, what are mistakes that are common that they should make sure to avoid?
Wesleyne Greer: Giving up too quickly. I think that is the number one mistake that organizations can make. Sometimes when I present the data and I say, Hey, these are the gaps. These are the areas of deficiency that I see in your organization. I have literally had people say, sounds like I need to get rid of all my managers because they're not meeting the mustard, right?
need to work on to be fixed.[:So don't give up too quickly. Give whatever coaching development training program that you're investing in. Give it time. See and celebrate the small wins. Celebrate the small changes that people are making because it's all about squeaking behaviors. One skill set at a time. So if you see them doing something that you've never seen them do before congratulate them for that.
Appreciate that them for that. And really make sure that they understand that what they're doing is positive.
Lucas Price: Underlying all of this is in order to make something like this work, I think you have to have a culture of learning of a bit, willingness to change to get better. Absolutely. If a company is struggling with that in their culture, how do you think about what they would do to start bringing that as part of the everyday part of their culture?
tead of only having meetings [:I want to share this book that I'm reading about how to communicate more effectively with my employees. And so I'm reading this book and here are some of the insights that I've gotten. I'm curious, do any of those strike anything with you? Is there anything in that I mentioned that you can use within your day to day?
Really showing that it is important for me as a leader to grow, to learn, to do. And so I'm not asking you to do something in theory. I'm asking you to do something that I do. And so that change really comes from the top getting out of that tactical. We missed our numbers.
It's bad. I'm putting people on pips. I'm doing this. I'm doing that too. Okay. We missed our numbers. Let's drill down into the data. Let's figure out together what we need to do to hit our numbers next quarter.
ort term versus the longterm [:But the truth of the matter is those are just finishing something that's already in motion. And the real proactive activity is not about this quarter. It's about, one, two, three quarters out a lot of times. And so you have to be, have the sense of urgency about this quarter, but at the same time reserve a spot for and this is how I'm going to make sure that future quarters we're going to, excel and get better as well.
m focus, but that's probably [:Even if you sell something that is a very inexpensive product or service, People start doing the research 6 12 months before they pull a trigger,. Like I literally just activated software that I did a free trial for 15 months ago, . And so in that 15 months, I've been searching, I've been doing.
And so when we step into the eyes of the buyer, We realize that long term focus of what we need to do to nurture our prospects, nurture our customers, get our customers to buy from us again, get our customers to review us. If we think about that and we employ that internally and say, okay, we know that it takes about 15 months from the time somebody first gets the idea in their brain for them to purchase.
alance in the short term and [:Don't only focus on long term and don't only focus on short term. Really have a nice pipeline where we can see that steady growth.
Lucas Price: And part of that long term is thinking about skill development. this Kind of is taking us back to the management, but to the management coaching, but I would imagine a big part of what you're doing is. Helping sales managers become better at coaching those seller skills?
Wesleyne Greer: Absolutely. 100%.
Lucas Price: I find that people can mean a couple of different things with the word coaching, when you think what is a good coach in your role in sales management?
Wesleyne Greer: So for me, a good coach, I think one of the taglines or the things that I say often is a good coach coaches to the conversion. They don't coach to the output or the input. And so what you do as a coach is you're focusing on, again, I like to say individuals because many times we just say, Oh, the sales team, Oh, the organization.
at organization or that team [:So you're looking at, and I always say coach to the conversion. What does that mean? So as you're looking through the pipeline, that, okay, for, 75 percent of the team, we are, our conversion rate for the past quarter has been 25 percent where in the previous quarter it was 50%. We have a problem from inbound lead to getting that first meeting.
So let's focus on that. What are the soft skills that will impact that? What are the actual hard tactical skills that we need to focus on? So on the tactical side, we need to focus on contacting people faster, making sure our emails are effective. All of those things. We also have to think about the mindset.
u back from actually sending [:So coach the team on the hard skill that you need everybody to work through. And then during your one on ones, focus on the soft skill that you need to up level that individual. So that, the hard skill that they're working on actually moves faster.
Lucas Price: Is there a difference between coaching and giving feedback?
Wesleyne Greer: Yes. So when you're giving feedback, it's Hey, John. So I went in and I saw that you did this really well, but you also did this, and this. So next time I want you to make sure that you. Focus on this, focus on that. It goes back to that dictatorship, if you will.
noticed that the last couple [:You don't tell them what they did wrong. You don't tell them how well they did here or there. You really focus on the things that they are saying that they need to work on themselves.
Lucas Price: You're making sure that a person you're coaching is identifying the gap and you're helping them think about what they can do in order to close that gap rather than identifying it for them and telling them what to do.
did wrong and how I can fix [:So that cements in their brain because you're allowing them, you're literally coaching them out of the hole that they may have gotten into instead of telling them what to do and what not to do because it just goes in one and goes out the other.
Lucas Price: One change I made many years ago that made a big difference in my effectiveness as a coach and a manager. Was at the end of the discussion, they've identified the gap. We've talked about ideas. Really like ending every discussion with what the follow up plan is and what the communication plan is and making sure that they own the follow up plan and the communication plan.
And it's not going to be me. Saying Wesleyan, how did it go? How did it go? How did it go? Like they're going to change some behavior and then they're going to report back to me or they're going to report back to, whoever their direct manager is or what, but that made a huge difference is just clarifying at the end of every conversation, this is who owns what part of this.
And this is going to [:So
Wesleyne Greer: There has to be action. A coaching session is not impactful if there's no action. Otherwise, it's just, oh, okay, we had a conversation. Now go off and continue doing the same wrong thing. Give them an action item with a due date. And if they don't fulfill what they said they were going to do by that due date, then you have to hold them accountable, right?
It is our job to hold our salespeople accountable to their own development, to the action items that we've come up with, that they've come up with. And again, that makes them take action. Ownership and that makes them feel like their development is something that you really care about because everybody wants to feel like they are important, like their development, their growth matter to you as a manager.
ng common that you see where [:Wesleyne Greer: It's even worse than that. It's more yeah, we have a coaching culture. We have one on ones with our, with everybody every single week. And it's more like these one on ones, they're just beating the reps over the head with data, with what they're not doing . And so I guess you could say that's a feedback culture.
They're not allowing people to move from one place to the next. And one of the things that I really ask, I'm like, okay, so tell me what your one on ones are like. Okay, so every single week that's what you're doing. And what's the outcome of that? Oh, okay. People are still not hitting their numbers.
allowing them to hold their [:Lucas Price: How do you start to change that from a feedback culture to a coaching culture?
Wesleyne Greer: So what I do is I really like to allow them to see the mirrors. Again, I'm going to step in and I'm going to watch these one on ones a couple of one on ones that they're doing a couple of group team meetings or whatever they want to call them. And I take all my notes and then I say, okay, so next week I'm going to have, I'm going to conduct the meeting.
And I show them exactly what I'm doing. And after we, I show them how to conduct an effective team meeting or group coaching session. I asked them. Tell me what's the difference you saw with the way I did it versus what you did it. So I am coaching them too, right? I am doing, I am actually practicing what I want them to do.
onduct it themselves. And at [:Okay. What did I do? Good. What did I not do? Good. And so they're getting it in their brain. They're like, okay. I can see, I can feel it and their team is more engaged. Like when you have these coaching sessions, these meetings where people get to talk and share their ideas and they know that they're heard and they know that they, you care about their development factors.
It opens it up from everybody being off camera, not talking, the manager only talking to people openly and actively sharing people trying to connect with their colleagues offline because they're like, Oh, I didn't know you were working with that kind of customer. I need some help with the person. I am.
Working with those things are so important.
Lucas Price: When you have a manager who's going through this transition I was giving feedback and now I'm coaching and I'm being taught like a methodology. coach. Do you ever see the sales reps wondering about if I don't know, like maybe they might not articulate it this way, but I've seen like them feel like maybe they're being manipulated because this methodology is being used on them.
ave you run into that at all?[:Wesleyne Greer: Typically I don't run into them feeling like they're manipulated. I run into the resistance of the, so the resistance I get are usually from top performing sales reps or sales reps that have gone through a couple of iterations of managers. So I call it, that PTSD, right? If they've gone through a couple of iterations of managers, It's hard for them to trust anything new and a top performing salesperson.
They just think that they're great and they don't need to be developed. So when the manager is starting to change, they're like, I don't need this. I'm already amazing. And so it's important to meet people where they are. I literally say a top performing salesperson, they're hitting their numbers.
them see something a little [:And it gives you like a 10, 20 X return on your investment because they get things and they're already moving at a really good pace.
Lucas Price: Yeah. So one thing I've seen before and I'll just I'll come to you like I'm your client. Hey, Wesleyan. I've been working on coaching. I've been coaching my team. One of the people, they asked, they rolled their eyes at me the other day when I asked him a question and they were like, Are you trying to coach me?
And I, I was just asking him a question, what should I do about that? Where, now I'm talking about coaching a lot and trying to get better as a coach and telling them I'm trying to get better as a coach. And now sometimes when I ask questions, they roll their eyes at me and ask me if I'm trying to coach them.
Wesleyne Greer: So I will ask them. I'm like, so if I am trying to coach, is there a problem if I'm trying to coach you? And they say, yeah, I don't want to be coached. And so I just want to understand why, because there's an underlying reason, right? Either they have had a really bad coaching experience in the past, or again, they feel like I don't need to be coached.
ually find that happens less [:I saw some body language that suggested that. And they may be like no. I just, that's how I think. And I'm like, oh, okay. Or they're like, I already know this. I'm like, great. Why don't you teach it to me? If you know it, just teach it to me. Because I'm open to learning new things.
So I push it back on them to try to figure out where they are and how I can get them out of that zone, that realm of where they are to where they want to go.
Lucas Price: I really appreciate you taking the time to do this with us today. I think that the conversation around how to invest in your sales management and, starting with the data and figuring out what skills need to be upleveled. Was really great and really appreciated your insights around the difference between feedback and coaching.
appreciate you being with us [:Wesleyne Greer: Thank you so much for having me. It has been an absolute pleasure to share with you and your audience.
