The Fearless Thinkers Podcast | Season 2, Episode 15

Bridging the gap from salesperson to sales manager

with Kyle Dean

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About the show

The Fearless Thinkers podcast, hosted by Rick Cheatham and Masami Cookson, personalizes BTS’s perspective on the people side of strategy.

Fearless Thinkers is produced by Gloria Breck and Aron Towner.

Special thanks to Joe Holeman, Chris Goodnow, Meghan McGrath, and Roanne Neuwirth for their invaluable help.

What makes a great go-to-market leader?

“It’s about that consistency that you’re able to create for your team and for your clients — thinking about how you establish your operational cadence helps to reinforce those expectations when you’re not there all the time,” says Kyle Dean, Senior Director, in this episode of Fearless Thinkers. Kyle and Rick Cheatham, CMO, share ideas for all salespeople to consider as they progress both professionally and collectively.

Roadblocks to sales-management success: shifting variables

Rick Cheatham: From your perspective, what are some of the key challenges that are [affecting sales management]?

Kyle Dean: We’re seeing a lot being asked of sales managers. There’s more data and information available than ever before. They’re seeing disruptions to their business that are so far outside of their control.

As the world continues to fuse together, you’re seeing disruptions that happen in Asia then impact decision-making in North America. Additionally, you have a lot of intrinsic information that they have started to need to gain access to.

Honestly, a lot of them who are stepping into the role for the first time as they’ve been getting promoted over the last couple of years… That’s requiring them to learn on the job [as] leaders for the first time; moving from being a high-performing individual contributor, to having to think about how [to] multiply their skills across their entire team and adapting their leadership capabilities to them; [all] while meeting the needs of a changing and complicated customer network.

Rick Cheatham: I think some of those things are common across leaders and managers in general right now — how people aren’t able to trust their judgment as they once would, and so those decision cycles do get longer and more complex — and [also the] rate of change driving priorities. The old world of “We’re going to set our three-year strategic plan and just hold to it!” [is] just such a distant memory. If they are still happening, they’re probably not effective. So, I definitely see the challenge, especially for those frontline sales managers also affected by that in their customers organizations.

Kyle Dean: Because of what you pointed out last, that idea of, this is going on in their customer organizations as well, that outside dynamic of having to work with customers is what really challenges sales managers beyond what traditional leadership development is tackling in today’s market.

In fact, what we find is that when you are a sales manager, you have to understand 1) how to think differently about how you’re leading your team and your clients at the same time, because you’re representing the senior leadership of your organization when getting into customer and client conversations; 2) how you’re developing your team to meet the needs of your shifting clients — not just the needs of your existing organization; 3) how you’re effectively executing on your quota and making sure your team’s delivering on that quota (something that can be increasingly complex as people are reevaluating how they’re putting together packaging models), and 4) how people are making decisions and slowing down with the complexity of the existing economic environment and the volatility that we’re seeing with just the rise of a lot of these new technologies coming forward.

From seller to manager: developing your existing manager population

Rick Cheatham: Many organizations just expect their standard leadership training to be enough, but they don’t necessarily think about that part of being a great sales manager that has that execution component. I think that’s why so many organizations nominate or promote their sellers into management. It’s actually been an unfortunate thing that I’ve seen in my own career, where great sellers think that they should be managers just because that’s next on their career roadmap, but they don’t necessarily want to be and they often love what they do. It’s that old cliché that says, when you promote your best salesperson into management, you lose your best seller, and you get your worst manager.

Kyle Dean: That transition from seller to manager, we see it come from a couple of different lenses. Either they love what they do, or they think, “I want some stability. I don’t want to have to chase these clients. I’ll go coach and enable my teams.”

These managers over-rotate into a couple of different skill areas. Either they become that braggadocious leader who paints the big vision, seems to be the life of the party, and everyone loves them, but they don’t actually get anything done. They’re not able to motivate or develop their teams as they go forward. You get some sales managers that focus on winning every client engagement, and they just become that super seller, where their teams are no longer able to be effectively engaged as they go forward, and they aren’t building the skills to close those big deals. You’re losing some of your top talent because those managers are just trying to hoard every deal themselves. Then you also get some sales managers that are out there saying, “Hey, update the CRM, where’s the update in the CRM?” They’re too focused on the data available to them, because it wasn’t the lens that they had as a seller. Maybe they had some bad examples of sales managers in the past, and they think, “Oh, this is just all about getting as much data and accuracy as possible,” rather than making prescriptive decisions and helping teams prioritize how to be effective with the information in front of them and really directing client relationships and development of your talent in a different way because of it.

It’s not only about making sure that you’re developing these new managers. It’s also making sure you’re thinking about your existing manager population as well, probably demonstrating some of these less-than-ideal behaviors.

Rick Cheatham: That’s why my old sales organization, we actually put in a challenge for sellers that wanted to go into management that they had to do a rotation, either in sales enablement, marketing, or just show up as a formal mentor for new salespeople, because those are all experiences that prove to me that you care about developing people or you understand the broader business.

Traits of a great sales manager

I would love it if we could back up just a bit and talk more about what it takes to be a great sales manager.

Kyle Dean: People might think of leading as [the] general leadership skill that we have to motivate a team. The best leaders, when it comes to sales managers, are those who are able to clearly establish a unique vision for their team and help them understand what is that purpose that their team has, along with how they’re motivating and serving their unique client market in service of your organization’s broader goal.

It’s also about how you’re setting effective expectations. And this is probably the thing that gets overlooked most frequently when it comes to leading your team and motivating high performance overall, when we think about setting expectations. So often, we ask our managers to go and coach or go give feedback, but without letting people know this is what you’re expected to do, or getting buy-in by co-creation together — you’re not effectively setting expectations that you can hold your team accountable to. It’s not just about telling them, here’s your target and quota for the month, or here’s how many calls you need to make, but rather what needs to go on inside of that, and making sure you have something to coach to as you work to develop them in the future.

And last is executive presence: demonstrating confidence, living the values of your organization — a balanced approach of what we can do to help the customer or client, and what we need to do for our team. You are that final say. Most people think you don’t need that until you get more senior in your career, where sales managers need to develop that early, and it’s part of their development path. It’s easy to forget that these people are the company to the clients that they visit and the salespeople that they interact with, and they don’t get to connect with other people in the office most of the time.

Rick Cheatham: Some of the best advice that I got when it comes to developing salespeople is knowing when to give feedback, when to coach, and when to model. Part of being a sales manager, you’re almost like a mini-GM: you might not have a full P&L, but you’ve got a lot of variables going on in your business, and the way you use data is incredibly important, I would assume.

Rick Cheatham: It’s easy to forget that these people are the company to the clients that they visit and the salespeople that they interact with, and they don’t get to connect with other people in the office most of the time. They’re out in satellite locations, interacting with their customers, more often than not, than they’re interacting with their peers.

That capability of a local leader to project authentically who we are [and] what we do is really important. What are those who are developing their teams and their markets doing the best?

Kyle Dean: When we think about developing, it’s about setting the course of what your future Sales team needs to look like to meet the needs of your customer. As you start to analyze where your market’s going [and] what that ideal customer profile that you put together is, you need to think about what are they going to need to move their business forward? Are we able to act as an advisor, or are we just doing some of the research work that our clients are maybe able to do by themselves online?

It’s then making sure that you have the ability to model the great behaviors that are going to be essential — to build those skills — so you’re able to set the expectations and help teach them what they need to do — and then coaching them to continue to refine and build those skills.

[It’s] being able to observe the behaviors that you’re seeing and adapting your coaching style to what’s going to be most effective for your seller in the moment of where they’re at in their career, where they’re at with their customer and client engagement, and where they’re at when it comes to building that future team and profile to meet the needs of your organization and your customers.

Rick Cheatham: Some of the best advice that I got when it comes to developing salespeople is knowing when to give feedback, when to coach, and when to model. Part of being a sales manager, you’re almost like a mini-GM: you might not have a full P&L, but you’ve got a lot of variables going on in your business, and the way you use data is incredibly important, I would assume.

Kyle Dean: Yeah, and this is probably one of the areas that is shifting most rapidly with the introduction of next-gen technologies, as AI is starting to provide recommendations on how you need to move forward. There’s less of the need to be able to come in and find what specific actions your team needs to go forward with.

Instead, it’s about that consistency that you’re able to create in your business for your team and for your clients: thinking about how you establish your operational cadence helps to reinforce those expectations when you’re not there all the time… Teams know that they need to update their forecasts every single Wednesday, and you’re going to be checking that and asking questions about what they see in the forecast in your team meetings on Thursday, instead of a readout on Thursday, when they get there.

Building that operational cadence is then critical for your leadership as well. They’re going to help dictate what the executive team needs, what we need to report out to the street. And so, working with them to identify what are the major business requirements of our cadence — you can then layer in when you’re going to have your team meetings, one of those one-on-ones and what is the time that you’re going to spend getting in front of clients that you can lead your clients with your team in mind, leveraging all the data available to you to then be more specific in those interactions with your cadence.

Additionally, when it comes to executing, we need to make sure that we’re thinking about who are the different stakeholders that we’re managing from the internal side of our organization. As a sales manager, you are the gatekeeper for your team, and you’re also there to remove any hurdles for your team as well.

So, thinking about how you are prioritizing your goals and your team’s time and the time of those around them, understand the levers available to them to either accelerate opportunities through the pipeline, or thinking about how we’re either increasing the number of new opportunities filling the top or understanding the actions they can take to help upsell, through their team, into those existing opportunities to increase the size of deals that are going through your pipeline.

Rick Cheatham: So, if we’re going to build great sales managers, they’ve got to lead, develop, and execute. Makes a ton of sense to me.

But what if I’m a sales manager that doesn’t have positional power to really make something like this go? What’s your best advice for that person?

Kyle Dean: If I’m that person, there’s nothing like getting a long list of all the things that I could be doing better and trying to figure out where to start… But what I would recommend is starting with your operational cadence. Now, while we think about this in that execute bucket, the end of lead-develop-execute in our framework — that operational cadence tends to pin everything else down. Then you can start to think about building the unique skills that comes to developing your team and identifying what it is that your customer basis needs so that you’re hiring and selecting and building the right talent around them. You can start to think about how to put your data analysis and focus on your pipeline and forecast into the lens of that cadence.

And then you can continue to build your leadership skills in those elements of your cadence. When are you going to show up differently with how you’re setting expectations for your team, laying out the vision for success? Or even thinking about how you’re going to show up for your customers and demonstrate your executive presence. So, you can take small experiments for yourself and continue to build those skills.

Rick Cheatham: Well hey, my friend, always great catching up with you. Thanks for joining us. And I’m sure we’ll have you back again soon.

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