Supercharge Your Sales Team (Event Recap)

*Note: This is not a direct transcript. Content was edited for length and clarity. Watch the video for the full livestream or continue reading for the recap.

Welcome to our livestream panel discussion “Supercharge Your Sales Team” with Robyn Clark, Founder and CEO of WinningWise, Inc., and Keith Bossey, Founder and President of Bossey Advisory Partners.

Our discussion moderator is Lauren Frank, Director of Consulting at WinningWise, Inc.

Q: Let’s start with a little bit about what each of you do and why “supercharging” your sales team matters so much.

Robyn Clark

We focus on org and talent development. We want to help organizations solve people problems and grow their people for greater capability and greater opportunities and to make their organizations bigger and stronger as well.

For us, sales training matters so much because it’s at the front end of what organizations are trying to do. Growing salespeople is not easy, so Keith and I have partnered today to have a good conversation about how to upskill, grow and “supercharge” your sales team to make them more effective, and, ultimately, to allow people and the organization to grow together.

Keith Bossey

We’re a growth agency, and we help mostly founder-led companies grow their organizations, teams, people and themselves. When I teamed up with Robyn and Lauren, we talked a lot about how you grow people. It’s incredibly important when you’re building a go-to-market platform that it’s based on people. And a lot of what’s going on out there in our world is not really impactful in terms of growing people, but rather focuses on growing markets and performance.

We’ve actually conducted surveys and studied which individual needs are most important to people in terms of their work (based on the researched and validated needs wheel above). Note: We didn’t study only salespeople, but salespeople were included in the survey. These are what we found to be the 3 most important individual needs:

1) Mastery: Most people want to be really good at what they do. They want to feel successful. When you’re not achieving, you don’t feel successful, so your mastery takes a big hit. They want to be included in things and part of the decision making.

2) Personal Growth: People want to feel they have a bright future and they’re growing. That’s super important.

3) Lifestyle: People want to have balance and flexibility and a way to put life and work together. Yesterday’s sales mercenaries would work 24/7, but that’s not the way people approach their work today. We have to be thoughtful about that. I remember one of the old sales strategies was always, “Make sure they’re hungry and keep’em hungry; that’ll keep them motivated.” That just doesn’t motivate people anymore. They’ll just go to the next place where they’re not so starved, where they can grow and their lifestyle fits. They’ll look for an organization that cares about those needs.

Rewards & Recognition is still on the list. People do want to be rewarded and recognized for the work they do, and money does matter. It’s just not in the top 3. Connection and Autonomy mean relationships matter, like “I want to be in on things and connected to you” but “don’t micromanage me or take away my decision-making.” We need a balance of you and me – we need that to work. Connection was always in the top 3 pre-pandemic but has now dropped to the bottom 3. I don’t know if that’s good or bad, it just is.

The other need that used to be in the top is Meaningful Work. People still want to do work that matters, but they want to be good at the work that matters, so Mastery has taken a higher spot. I also really like the way younger people look at their work because they have a learning orientation, which fits with Mastery and Personal Growth being at the top. That is very different than yesterday’s worker – there wasn’t much of that. With learning orientations, there’s greater opportunity for all of us to grow.

But the important thing, as Keith mentioned, is to make sure you do this in an individual way. Not everybody will have these as their top 3. And that’s why it’s important to know your team.

Q: One of the topics we want to cover today is elevating the training lens for salespeople, knowing the environment is dynamic and we need to get people growing and building capability to respond to this environment. We also know that development is the No. 1 driver of engagement for employees – for sales teams and all teams. Robyn, I’d love to hear you talk about what you think is critical for sales leaders to consider as they think about growing capability on their teams.

Robyn Clark

When you look at how sales leaders speak about their teams, most of the time they’re trying to take their farmers and turn them into hunters. Rarely are they going the other way around. We’re trying to get people to look for more, find more, hunt more. The ability to farm really does matter to keep clients and build good relationships, but when looking to “supercharge,” you want to figure out the hunter situation.

It’s not easy to turn people more inclined to be a farmer into hunters because it asks people to do different things or make big changes. It asks people to take more risks, show up with a bolder voice, make bigger requests, or be more proactive. That’s not like asking people to learn more about products or the market. You’re asking people to embrace personal change.

Embracing personal change is what growth and development is all about. If you’re going to take more risk, for example, that takes you shifting your mindset and approach. It means being more ok with rejection and raising your confidence level. Those aren’t so easily taught, but rather developed through practice, feedback and connection. Does that make sense based on what you’ve seen, Keith?

Keith Bossey

Completely. You talk about moving people from a farmer to a hunter, and even at a higher level, a lot of sales leaders want their people to be more strategic and think bigger. They’re not necessarily looking for people to be better sellers, but to be better executives, better businesspeople. I think a lot of the training salespeople do is focused on products or sales capabilities or tactics or tricks of the trade. I read that we spend about $70B on sales training per year and 84% of that training is forgotten after 3 months. That’s a lot of wasted money. And that’s because we’re focused on products and capabilities rather than building our sales teams to be more effective, more strategic executives that are enabled to compete in this fast-paced, highly competitive environment where technology plays a big role. And in order to be a better executive, you need to know yourself and know what your strengths and weaknesses are so you can address them.

Robyn Clark

When you think about growth from a personal change perspective (whether you’re trying to grow someone from a farmer to a hunter or from a salesperson to a business executive or yourself from a salesperson to a sales leader), there’s a lot of transitions we make, but at the end of the day, the foundational center is around making personal change for you or, as a leader, helping grow personal change in others.

These are our Winning Action Strategies. They are 9 researched and validated ways for people to grow themselves personally to achieve greater success in their roles and in their work. Depending on your role, whether you’re a salesperson or project manager or executive, you might define each of these differently or have a different set of actions, but the concept is pretty similar from role to role. That’s the cool thing.

Here we’re talking about the application to sales. Along the outside are the Individual Needs. The needs I spoke about before that are important to people were Mastery, Personal Growth and Lifestyle. All the rest get a play too; I’ve never done any kind of session where they all didn’t get a vote from somebody. But those are the top 3 these days.

If you look at the Winning Action Strategies themselves, starting with the top row, salespeople or sales leaders looking to make a bigger personal impact should always look at how essential they are, how much they’re pushing themselves (i.e., taking risks and being more proactive), and how much confidence they’re exuding. Confidence is critical if you’re trying to grow from a salesperson to a business executive. Are you able to really show up in those conversations and bring a bold point of view so that people feel confident about you? Confidence is this weird thing where you can feel confident about yourself, but it also matters if others feel confident about you. It has an internal and external view. For sales folks trying to turn themselves into business executives, the external view of confidence is so critical because they’re moving up higher in organizations in terms of who they’re targeting, connecting with and talking to, and that’s really important.

The middle row is for people who need to be really good at building relationships. We tend to think of salespeople as good people-people who are good at building relationships. When they become sales leaders, they have to take this idea of building external relationships and turn it internal, i.e., how do you build stronger, better relationships with your team? Salespeople haven’t always had to think about how to build their team; they’re generally thinking about how to build relationships with their customer. When you become a sales leader, you have to think about how you can build better relationships with the other executives in your organization. Because that’s another way to turn yourself from a sales leader into a business executive. That’s why building a fan base and a followership around you is so important. Also, self-awareness is critical and you only get that through more self-reflection. A lot of people think they have more self-awareness than they do. It’s really important to consider that. There’s a study done by Tasha Eurich, I love her talk on self-reflection and self-awareness, and she said when you ask people if they’re self-aware, 85% say yes, I am self-aware. When you ask other people if those same people are self-aware, the number drops to 15%. Unless other people think you’re self-aware, you don’t get the self-awareness badge. That is important to think about. In sales, self-awareness really matters because how other people experience you is pretty critical, whether you’re in front of a customer or trying to get to a higher level or working internally to be more influential in your organization. Giving back is about having a bigger picture view than just yourself. It’s an enterprise-wide view. Can you sell and work in a way that is beneficial to my whole organization AND the organization I’m selling to?

The bottom row is all about having more social power and influence. Can you negotiate well? We know that’s a critical skill of a salesperson, but it’s not just negotiating for numbers and money. It’s for service and deadlines and roles and how things work. What can you do, what can I do, how can we win? When Keith mentioned sales leaders being more strategic, that generally falls between always have a plan and understand the game. Sometimes you get more strategic by having bigger views and being able to turn that into actions, and then exercising discipline and accountability to figure it out. Or being more strategic can be understanding how sales works in your organization and other organizations, such as who are the decision makers? Have we gone from single to committee decision makers? What roles are people playing on those committees? How do I help understand their needs? How do I get more thoughtful and ask better questions? All of that is understand the game. So, when we think about development, we think about not just the competencies or capabilities we need salespeople or sales leaders to be good at (like strategic thinking or communication or customer relationships or different sales tactics), when we think about development, we think about: “How do I change me, so I can deliver on those things that are expected of me and desired by me?” Does that resonate?

Keith Bossey

It does, and I think the last thing you said about change (“How do I change me?”)… sales is about change. You’re trying to get your client or prospect to change their view on the world, change what they’re doing. And this whole concept of understanding who I am, how I can change myself, how I see myself, not only inside my organization, but how I see myself inside the client’s organization, and how do I get change? That is all this is about. How do I get change? Myself, my prospect, my company, and what’s my role to fit into all of that.

Q: Keith, I want to ask about something we all agree is important. The best salespeople don’t often translate into the best sales leaders. I want to know your perspective. Why is that the case? And what do you think organizations should keep in mind when building out these sales benches for their sales leaders?

Keith Bossey

There’s a really huge shift in what the goal is when going from a salesperson to a sales leader around a lot of the things Robyn just went through in terms of understanding yourself. As a salesperson, you’re presenting a high degree of confidence, like Robyn said, the outward confidence. And as a sales leader, you have to turn that down and recognize that you’re secondary in this relationship because your goal is to raise up your people. You have to go from being this outward confident, driven, goal-oriented person to stepping back and saying my job is now, it’s cliché to say, the servant leader. But you’re really trying to get the most out of a team and so you have to go from being outwardly confident and forceful to heavy, heavy listening and coaching.

In my time as a sales leader, I found the biggest value I could provide to my sales team was in coaching them. Helping them see what they’re not seeing, helping them elevate themselves. I think back to my comment about training not being effective and being lost after 3 months, and it’s because most companies don’t have a process in place to enhance and embed any training they do through ongoing coaching. I think a lot of sales leaders resort to pipeline, i.e., let’s look at your pipeline, what are these deals, what do we have to do to move these deals forward? And in many respects, you need to put that aside and just say what’s standing in your way in terms of being successful as a salesperson. And really dig deep and identify how we can get that accomplished. It’s a big mind shift away from pipeline and moving deals and succeeding and closing to elevating other people. I was never trained to do that; most companies don’t train their sales leaders to think that way or do that. And they certainly don’t put anything in place to make that happen. That, to me, is the biggest thing.

Q: Robyn, let’s go back to the Winning Action Strategies and talk about how those could be helpful for organizations as they’re thinking about building benches for sales leaders.

Robyn Clark

I’m going to build right on what Keith said because that is exactly right. What happens generally when you’re a good salesperson, like let’s say you’re one of the top salespeople, generally speaking you’re going to be pretty darn good at the top row of the Winning Action Strategies. You’ve probably built a lot of “essentialness,” you’ve probably learned how to push yourself and take risks and get outside of your comfort zone, and you probably approach things with a great deal of internal and external confidence, and that’s allowed you to continue to do really well.

As Keith just mentioned, when you switch to the sales leader, there’s a huge emphasis on the middle row. Now, all of a sudden, it’s not about me, it’s about us (building a fan base) and it’s about you and I have to help you be successful, as opposed to me trying to run around and sell on everybody’s accounts. That is tempting for so many sales leaders. But if you’re really going to be able to do the coaching Keith was mentioning (which is a YES on every level), then you’ve got to absolutely focus on self-reflection. To make that shift to servant leadership mode or supporting others takes a lot of self-reflection and self-awareness. Then, you might want to adopt a give back orientation. That isn’t always the first thought of what a sales leader might do. Rather they’re going to say, “Let’s look at your pipeline, what do you know and not know about the client?” instead of “How can I help you grow so you can do the things I know you know to do.” Most salespeople know they have to look at their pipeline and know their clients. The question is really what’s in the way of that? What’s making that hard or difficult or how can you grow to get there? So, for sales leaders, a lot of that focus is going to be on the middle row so they can help people on the top row.

Now, if you’re really trying to be a business executive, so you’re moving from a first-level sales leader role into another level supervising sales leaders (as opposed to salespeople), you’ll want to look at the bottom row. For people going up to or getting ready to go up to this whole other level, kind of building that bench, it will be super critical that they can negotiate. I don’t mean negotiate client deals; I mean negotiate needs between different functions. There’s often design and engineering and operations all involved and what the salespeople are promising conflicts with that triangle. The people called upon who are needed are people who can resolve and negotiate conflict between that triangle so that the things salespeople say they can deliver might actually be deliverable. You know how tough that can be in organizations to be aligned on what we want to do vs. what we can do. It’s also really important as you move into that executive level that you know how to always have a plan. I don’t mean make a to-do list. I mean really be thoughtful and strategic about a vision and goals and be able to assess talent across your organization to see who in the world can do what things that help close the gap to where we want to go. And then you understand the game and the needs of the different functions, customers and marketplace. There’s a lot of multi-games going on at the same time. You have to understand the needs of all of them. But all of those things are personal change. I can’t tell you how often people are working on the idea of visioning or coming up with change agendas so they can move people in organizations forward. Those are very top-level competencies and sometimes letting your imagination go in that direction or being able to embrace the change that would require is a lot of personal shifting. So, in some ways, as you work your way through, you kind of see that the level increases as you move down the Winning Action Strategy diagram.

Another cool thing about the Winning Action Strategies is that it’s all about motivation and inspiration because personal change is hard. Let’s face it. Nobody really wants it. Everybody says they want to grow and develop and want more, but nobody says they’re looking forward to “change.”

This diagram is sort of a game board. If you can play tic tac toe, you can play with this. If you want more personal growth (as your Individual Need), look at the vertical middle path of Winning Action Strategies: Push Yourself, Practice Regular Self-Reflection and Always, Always Have a Plan. Those who are good at those 3 things will have more personal growth. The pathways make it easier for people to see the what and the why. That’s really important for helping your salespeople turn into sales leaders and then into real true business executives and allow your organization and people to grow simultaneously.