January 12

How Sales Managers Get Set Up To Fail


Sale Leadership Awakening
Sale Leadership Awakening
How Sales Managers Get Set Up To Fail

In the Sales Leadership Awakening podcast, Steven Rosen and Colleen Stanley stress the lack of coaching and support for sales managers, underscoring the need for coaching for these managers. Key skills for sales managers include coaching, executing sales plans, and prioritizing a coaching methodology. 

“Most people don’t leave for money. They leave because of their manager.” – Steve Rosen

“If you don’t have a sales playbook, some type of methodology, I don’t even care how simple it is. Because simple often wins, you can’t coach without a playbook.” – Colleen Stanley

Soft skills like emotional intelligence are crucial for building team trust. Evaluating sales managers’ success should exceed sales quotas and include turnover and team development metrics. Ultimately, investing in sales manager development and support is crucial for organizations to achieve a successful year.

Follow Colleen Stanley on LinkedIn

Follow Steven Rosen on LinkedIn



[00:00:03] Steven Rosen: Hello and welcome to the Sales Leadership Awakening podcast. I’m Steven Rosen, and I’m with my co-host Colleen Stanley. Together, we’re going to tackle the age-old issue of bridging the gap between knowing and doing, especially in sales leadership. Over the month of January, we’re going to focus on crafting how to have an excellent year versus mediocrity, having a blockbuster year as opposed to a lackluster year.

[00:00:34] Colleen Stanley: Steven, good morning. Good afternoon. I know we’re in two different time zones.

[00:00:39] Steven Rosen: We can manage both. That’s the beautiful thing about us.

The Sales Managers’ Predicament

[00:00:41] Colleen Stanley: So one of the areas to look at to have the difference between a mediocre year versus an excellent year is the uncomfortable truth.

[00:00:54] Colleen Stanley: Are we setting our sales managers up to fail? Because, for presidents, chief revenue officers, and VPs of sales, like it or not, sometimes we are setting our sales managers up to fail, and that leads to not having a blockbuster year but a lackluster year. Steven, we talk a lot about the knowing and doing gap, but let’s unpack this.

[00:01:16] Colleen Stanley: What are some of the things in all your coaching conversations where chief revenue officers and presidents of companies have the right intention, but maybe the methodology is off as far as providing the right support for sales leaders?

[00:01:28] Steven Rosen: It’s not an easy job, right?

[00:01:30] Steven Rosen: Those of you who’ve done it and are doing it or new to it, you’re a top rep, and then one day someone taps you on the shoulder and says, Colleen, we want you to lead the team. You pick up your hand and say, hey, I’m in and move forward.

[00:01:44] Steven Rosen: But no one thinks, Oh my God, we have to make sure this person is ready, that they have the right tools in place, that they have the right skills, training, and development to move from a top sales rep to become a top sales manager. And often, the well-intentioned CRO doesn’t have the processes in place to ensure they can make their manager successful.

[00:02:07] Steven Rosen: New skills and a different mindset are required to lead a team. So senior sales managers also forget that as much as they realize that their sales managers, as part of the sales management process, need to be coaching their reps, so do the senior sales leaders need to be coaching their new sales managers as well as their existing sales managers.

The Missing Piece: Coaching the Coaches

[00:02:28] Colleen Stanley: So the sales managers and coaches also need a coach. And so, a gap I’ve observed, and maybe you have as well, is that nobody’s coaching the coaches.

[00:02:39] Steven Rosen: Yes, 100%. The dilemma or the gap is that, hey, I’m CRO, and I’m asking my managers to coach their reps to make them better salespeople, but I’m not doing the same for my managers.

[00:02:53] Steven Rosen: And sometimes, I’ll be in with a CRO and just for the fun of it, ask them what are your KPIs for coaching your sales managers? And what I usually get is a blank look. What are you talking about, Steven?

[00:03:06] Colleen Stanley: And you know what’s interesting, isn’t it? We’ve got metrics for our salespeople.

[00:03:10] Colleen Stanley: Sometimes, even for sales managers holding the coaching cadences. But then, if you go one level up, who’s holding the VP of sales or chief revenue officer accountable for developing their team in very tangible ways? So it’s a really big gap out there that I’ve seen in almost every organization I’ve worked with.

[00:03:28] Steven Rosen: I’m with you. From a business perspective, it’s not a bad thing because sometimes I will fill the gap. But I can’t do it for every single month of the year. We may come in and help the group. We may coach the managers. But who sustains that within the organization if they desire a blockbuster year?

[00:03:42] Steven Rosen: That’s what we’re talking about, how to make sure the year is great. It’s about getting the sales managers up to speed and sustaining that.

[00:03:54] Colleen Stanley: Absolutely.

Developing Sales Managers for Success

[00:03:55] Steven Rosen: So what do you think are some reasons why sales managers are not just set up to succeed?

[00:04:01] Colleen Stanley: It goes back to personal accountability. If you’re the person raising your hand, you decide, hey, I want to be a sales manager. You’ve got to apply that EQ skill of self-awareness and use Simon Sinek’s words, Why? So there are three questions to ask yourself.

[00:04:20] Colleen Stanley: If you’re raising your hand, number one, are you going to get as much enjoyment being a sales manager as you were an individual producer? One of the questions I always ask sales managers considering this is, are you going to get as big of a kick out of your salesperson landing a big deal as when you landed a big opportunity? That makes sales management fun: you’re happier for them to exceed their goals, meet their goals, and even achieve your own.

[00:04:51] Colleen Stanley: The second point is that I learned as a sales manager and eventually a VP of Sales that I had to have the humility to admit that I had some blind spots. My big blind spot is I was a teller, not a coach. Even more importantly, and I know you work with a lot of your coaches on this, I kept giving feedback in the manner in which I like to receive it.

[00:05:14] Colleen Stanley: So I’m a direct person. I grew up in a household where there was not a lot of fluff and stuff. And so I don’t like that thing that’s sometimes called the sandwich method: three positives and then the behavior you want to see change. Just tell me the behavior you want to see changed.

[00:05:30] Colleen Stanley: Well, Steven, when I was coaching a rep, she started getting tears in her eyes, and it wasn’t because she was this soft cupcake, as we’d call it. I wasn’t giving her feedback in the manner in which she liked to receive it. She liked to have the accolades first. Now, as puzzling as that was for me, boy, was that a blind spot.

[00:05:51] Colleen Stanley: And I couldn’t blame her for not being a tough it up, bucket up person. That was on me. The third point to consider is if you’re raising your hand, you’re going to have a very steep learning curve because, as you mentioned, you’ve got to learn new skills. And I know we’ll have you talk about these in a minute, but there are new skills to learn that are going to take practice and study.

[00:06:14] Colleen Stanley: Are you willing to invest the time to learn the new skills to become as masterful at sales leadership as you were an individual producer? So, I’m going to throw the ball back to you and let’s talk about some of the hard skills these sales managers will have to learn, study, and master.

[00:06:35] Steven Rosen: I loved your story about that young lady, and it begs the question you may have left. I was hanging on, hoping you were going to cover it. How do we know what the right way to give feedback is?

[00:06:48] Colleen Stanley: I learned it. I just started asking people. How do you like to receive feedback?

[00:06:53] Colleen Stanley: It was a duh moment.

[00:06:56] Steven Rosen: No, it wasn’t. Everyone forgets that.

[00:06:58] Colleen Stanley: How do you like to receive feedback? And I have a consultant. He used to work with me for years. Now he’s gone back into the public sector, and we love working together because we’d say when we get on a coaching call, we get down to business.

[00:07:12] Steven Rosen: I was wondering where you were going.

[00:07:15] Colleen Stanley: Yeah, but that’s easy when you’re working with someone with the same communication style and maybe needs if we want to put it in that framework. So, I simply started asking the question.

[00:07:23] Steven Rosen: Okay. And that’s part of the role.

Coaching: The Key to Sales Performance

[00:07:25] Steven Rosen: Great sales reps ask great questions. Great sales managers ask great questions. So there are similarities, and sometimes we don’t bring that over, and some of the key skills you may not have learned as a salesperson because a good salesperson doesn’t necessarily make a great manager. The greatest hockey player, Wayne Gretzky, did not make the best coach.

[00:07:50] Steven Rosen: He stopped coaching because he wasn’t winning games. But in terms of skills, if you look at building a team and setting your sales managers up for success, teach them how to hire effectively.

[00:08:03] Colleen Stanley: Oh, say that again and again.

[00:08:06] Steven Rosen: I will, and I will. Yes, 100%. And it’s different skills.

[00:08:10] Steven Rosen: You have to train on that. You can’t just throw someone in and say, by the way, you have a spot to fill, or they have a spot to fill, and not give them any indication of a process. If you follow a hiring process, it takes some of the pressure off the sales manager to do that. So, a company has to have a process.

[00:08:27] Steven Rosen: Is the new or existing manager clear on what skills they’re looking for? Are they clear on what a top performer in your organization looks like? Those are some key clarifications.

[00:08:39] Colleen Stanley: This is interesting because, as you mentioned earlier, you can take some skills you had as an individual producer.

[00:08:46] Colleen Stanley: And if you know how to do it, frankly, you will find there are some similar skills here. So what you just reminded me of is we are all over sales training. Get your ideal client profile, the psychographics, the demographics, and the values. How many of us have actually built that profile for our own sales team?

[00:09:05] Colleen Stanley: This is who plays well on my team at this time at my company. So, you’ve got to have an ideal client profile when you’re hiring.

[00:09:15] Steven Rosen: If you’re not arming your sales managers with that, guess what? They’re going to make hiring mistakes. They’re going to make more hiring mistakes.

[00:09:22] Steven Rosen: And those are costly. They’re a drain on time. They’re a drain financially. So, you need to get some things in place to set your manager up for success. We talk about the elephant in the room: are we setting them up for failure? The opposite that is, how do you set them up for success? In terms of skills, anybody you ask, I’m sure we’ll agree that coaching is the most important skill that impacts performance.

[00:09:47] Colleen Stanley: Absolutely. We all know it, and we know how to do it.

[00:09:50] Steven Rosen: Even before that one, do we have a methodology that the company follows? Many companies don’t have a methodology, so coaching is left up to the sales manager’s best guess at what a good coach looks like. Two, have they been trained on the methodology?

[00:10:05] Steven Rosen: Do they have KPIs that say coaching is important? Do they build plans for their reps, or do they do what I call flavor-of-the-day coaching? Today, you have to work on this; tomorrow, you have to work on that. That doesn’t work in coaching because coaching is about creating skill proficiency and mastery.

[00:10:21] Steven Rosen: So to send the sales manager out and say, Hey, go coach without having the skill or the tools to do it again, sets them up for failure. 

[00:10:35] Colleen Stanley: What you’re bringing to mind here is going back to your hiring. So, I have found that many companies don’t have a hiring playbook.

[00:10:45] Colleen Stanley: And when I ask them, so show me your hiring playbook, show me your interview guide, there isn’t any. Everyone’s just showing up, and interviewer number one’s going to ask this set of questions, interviewer number two is going to ask this, and none of them may match that ideal client profile. And secondly, your point as a methodology: If you don’t have a sales playbook or some type of methodology, I don’t even care how simple it is because simple often wins; you can’t coach.

[00:11:08] Colleen Stanley: You can’t coach without a playbook. If we look right now, we’re in football season. Can you imagine all these players getting out on the field, and the quarterback yells the play, and everybody goes, huh?

[00:11:20] Colleen Stanley: What play is that? I don’t get it. We do that to sales managers every day.

Executing the Sales Plan: A Critical Skill for Managers

[00:11:25] Steven Rosen: 100%. So some of it is training. How do you bridge that gap? Once you’ve trained to make sure it becomes a reality, then one of the most overlooked critical skills, and I know we’re going to talk about it in an upcoming episode, is really how do they execute the sales plan?

[00:11:44] Steven Rosen: Again, before we even get there, the question is, do they write an execution plan? Is there a template, a process in place to say this is how we’re going to execute? Do they know what their critical success factors are? Is everybody aligned on the team? 

[00:12:00] Steven Rosen: If you have three sales managers reporting to you, one thinks the most critical thing is growing new business, and the other thinks it’s expanding on existing business, you’re not aligned as a sales leadership team. So unless we can help the new or even ongoing managers where you could have three managers, and they all have three different goals, and unless you’re aligned as a team, can you execute unless you know your critical success factors?

[00:12:23] Steven Rosen: Can you execute? And, of course, we need metrics to say how well we are doing so we can track execution. And that’s one thing that gets dropped. Companies are great at building marketing plans. Then, execution is lobbed over the fence to the sales teams and the sales managers, which leads to the adage that if it works well, it’s a great marketing plan; if it fails, it’s poor sales execution. That’s the life of a sales leader.

[00:12:51] Steven Rosen: So those, to me, are some of the key skills that sales leaders need, but there’s also the soft skill component, and maybe you can share with the audience what you feel are the key skills that we need to develop our sales leaders on.

The Soft Skills: Emotional Intelligence and Beyond

[00:13:05] Colleen Stanley: One of the interesting points is that soft skills almost imply that they can’t achieve hard sales results.

[00:13:14] Colleen Stanley: But if you unpack some of these skills, they are tremendous in building good teams, trust in teams, and execution. If I had to talk to three today, the first would be, thanks for listening. Emotion management is often called emotional regulation. This is important in building a team because if you are a sales manager who can’t manage your emotions, you’re always up and down, and so on good days, you’re good. When a problem comes along, you’re not so good.

[00:13:42] Colleen Stanley: So, what happens is your team sits there, and whether they’re remote or in an office, they’re sitting there going, Okay, what type of mood are they going to show up in? When they have to wonder how you’re going to show up, that erodes trust. A study was done by the Center for Creative Leadership in North Carolina.

[00:14:00] Colleen Stanley: They surveyed 302 leaders of all walks and titles. They found that 28 percent of their success was attributed to emotional intelligence. And there were four pillars. The first pillar was emotion management. Now, the second I would look at empathy and assertiveness.

[00:14:22] Colleen Stanley: And I put these two in the same bucket because here’s what happens. And I saw this after we came out of the pandemic. I had managers saying I’ve shown a lot of empathy, but we’ve got to get some stuff done. Do not confuse empathy with letting people off the hook. But it’s important to be able to state somebody’s perspective because if people don’t feel like you’ve heard them, they can’t hear you.

[00:14:46] Colleen Stanley: And there are times when your salespeople’s ears are on fire emotionally. So they can’t hear your great advice or counsel unless you can demonstrate empathy. Let’s add the assertiveness here because you can state their perspective, but maybe this is where you need to change expectations. The bar needs to be raised, a habitual attitude, and sales skills.

[00:15:07] Colleen Stanley: When you can show empathy first and then assertiveness, then you’re stating what you need nicely. Without assertiveness, very dominant salespeople, what I call the driver personality, can engage in passive-aggressive behaviors. They start going along to get along. I don’t want to rock the boat and talk about this in 10 years.

[00:15:28] Colleen Stanley: There are many more, but if you looked at those three skills and managed those three, you’re going to build trust, but you’re also going to build execution. Because behind the execution is assertiveness. I know, Steven, with the amount you’ve done on execution plans, there’s pushback. It’s changed. We don’t know what the future looks like, and that’s when it’s very easy for a manager to let off the gas and lower expectations.

[00:15:55] Colleen Stanley: With assertiveness, self-awareness, and empathy, you can have conversations that get that execution done.

[00:16:02] Steven Rosen: I love that level of depth in terms of the emotional component of leading. Companies are becoming more clued into the importance of that, but what are you seeing in terms of training sales managers or helping them develop their emotional intelligence?

[00:16:17] Colleen Stanley: When we started in this work way back in 2012, people thought we were crazy. I had colleagues saying, no one’s going to buy that. Part of it was a fair statement because what is tough about teaching emotional intelligence skills is that it can seem very intangible.

[00:16:41] Colleen Stanley: You can give examples and concrete exercises, but it remains theoretical and never practical. So that’s part of the reason. But now we’re seeing a lot more interest in it. And it’s this post-COVID pandemic environment. You’ve got a lot of people talking about mental health, mental management, people stressing and burning out.

[00:16:58] Colleen Stanley: And so many of the soft skills can help resolve a lot of those problems. We’re seeing a heightened interest in it, which is good—very powerful stuff. 

[00:17:11] Colleen Stanley: Steven, let’s throw it to action because I know you’re the execution king. I wish I were. If you were to advise those CROs. Let’s take it at the CRO level, but this question can also be asked if you’re a one-person sales manager.

[00:17:29] Colleen Stanley: How do you evaluate that the plan is working? How do you evaluate that your sales managers are doing the right stuff at the right time? 

Measuring Success Beyond Quotas

[00:17:42] Steven Rosen: Let’s get down to simple brass tacks. It is very challenging to assess how things are going.

[00:17:49] Steven Rosen: There’s a very simple way to look at it. Sales to quota is a direct way of looking at your sales managers’ performance. So we have lots of metrics to look at and say, Hey, did they achieve what they set out to achieve, how they’ve done, how are they doing relative to other sales managers, or how are you doing relative to the market?

[00:18:09] Steven Rosen: If you’re many, then you know how people are doing relatively, but that doesn’t tell you the whole story, does it? So, you look at the people component. Part of the manager’s role is, as we talked about, hiring the right people, developing the right people, and then actually keeping them with the organization and retaining them.

[00:18:32] Steven Rosen: What other metrics can we look at? The hard stuff is the hard metrics, and one is turnover. Of course, I used to use the wanted versus unwanted turnover. 

[00:18:45] Colleen Stanley: So there is some turnover where you’re like, thank you. 

[00:18:47] Steven Rosen: Yeah. What took you so long?

[00:18:51] Steven Rosen: And that’s okay. Except it’s what took you so long, and then there’s the unwanted turnover. Are people leaving? Because most people don’t leave for money. They leave because of their manager. If you achieve your numbers, but you’ve burnt your people out, there are other signs that the CRO wants to look at.

[00:19:07] Steven Rosen: And even if it’s yourself, if you’re turning people over, there’s something wrong. And one of the other things, which is very hard to gauge, and I’ve tried to build ways to do it, is, are you growing your people? Are you helping? Are you coaching them to get better at what they do? And certainly, the training group can bring in skill assessments.

[00:19:27] Steven Rosen: So let’s say you have your sales playbook, and the first component is asking effective questions or setting objectives. We can evaluate our salespeople’s performance against these specific skill sets or competencies. And then, have they grown as a result of coaching?

[00:19:43] Steven Rosen: You want to grow your business, which is easy to track. But you also want to grow your people. And so, my advice is if you’re looking to evaluate how effective your sales leaders are or how effective you are as a sales leader, it’s not just one metric. 

[00:19:59] Steven Rosen: If you’re going to hang your hat on sales to quota, that’s great, but there may be other things you want to look at, especially when it comes to the people. Are you experiencing turnover? Are you retaining your top people? And what are you doing to grow your people? Have they grown over a year?

[00:20:14] Steven Rosen: Because to me, a great coach, if you can help someone grow or develop in one or two key areas over the course of a year, you’ve done a great job.

[00:20:22] Colleen Stanley: This is interesting because it goes back to the sales goals and something we’ve talked about, learning goals. And all of that ties into an EQ skill of delayed gratification.

[00:20:33] Colleen Stanley: Putting together these individual coaching plans takes time. That’s putting in the work. And it’s looking at each person as an individual. Because, again, it’s so easy to fall into mass sales management. Everybody’s got this learning goal. I’m going to approach everybody the same way here.

[00:20:52] Colleen Stanley: But I have to tell you, I’ve had to really work at that. So I’m not just speaking about it. It’s looking at each individual and how you approach them. What are their personal goals? Some of my managers always knew my personal goals and somehow would help me achieve those as well.

[00:21:10] Colleen Stanley: Guess what? If you’re happy personally, you’re going to bring that into the workplace.

[00:21:14] Steven Rosen: Make your boss look good, right?

[00:21:16] Colleen Stanley: Yes, absolutely.

[00:21:19] Steven Rosen: So, any other pieces of advice that you want to share with sales managers or CROs so that their sales managers don’t fail? They’re not set up to fail, but they’re set up to succeed.

[00:21:30] Colleen Stanley: Take a best practice that we see from athletics, and instead of starting to train people when they’re in the role, why not start identifying high potentials? And Steven, I had an interesting engagement a couple of years ago, and it was with a technology company out in California.

[00:21:50] Colleen Stanley: And when they called me, I said, okay, are these people getting ready to go into sales management? No. Then, I was puzzled. Why are we training them? And their response was excellent. They said, here’s what we’re doing. We’ve identified high potentials, and they had to interview to be in this training program.

[00:22:06] Colleen Stanley: However, we don’t want to set them up for failure. So if they go through sales leadership training, and they know all the components, holding people accountable, having difficult conversations, setting KPIs and goals, one of two things is going to happen.

[00:22:23] Colleen Stanley: They’re going to opt out, but they’re still going to be better human beings because they’ve learned some of the hard skills and soft skills. And others will say, you know what, this is the role I want, and now we’ve given them the training before they step into that role. And it was just a really great insight for me and a wonderful team to work with.

[00:22:43] Colleen Stanley: So they were investing before these people even got in those roles. Now, that takes a leap of faith for a company because the thought could have been this: we don’t want to waste money on somebody who’s maybe choosing not to ever go into sales management. If you want to talk about something that costs you money, get a bad sales leader in place. They’re miserable, their people are miserable, goals are being missed, and, as you said, turnover is happening. So train your high potentials. It will cost you some time and money, but you’re looking at the financial statement the wrong way because we’re not capturing turnover, poor morale, and people not hitting their best potential.

[00:23:21] Colleen Stanley: Those numbers never get on the PnL statement. That is my advice to our listeners today. 

[00:23:27] Steven Rosen: That’s great advice. And you didn’t know this, but I am working on a program, and they’ve chosen a number of people, and we’re doing some assessments and some opportunities for self-awareness.

[00:23:39] Steven Rosen: EQ is one of the areas that we look at. So, not all of them want to be sales leaders or expect to be sales leaders, but what they’re doing is investing in their people. And I don’t know how many people have said to me, maybe half, that no one’s ever done this before.

[00:23:54] Steven Rosen: If you want to talk about retention strategies, just invest in them and treat them as special. They’re getting something that no one else in the organization has access to. And some of the access is a professional coach to work with them on their strengths and weaknesses.

[00:24:11] Steven Rosen: Two is interaction with senior leaders in the organization. So there are many things we can do because part of it is retaining our top people. We show them the love, and they’re more likely to stay than leave if they’re millennials. We show them the love and coach them. They’re not going to have a reason to leave.

[00:24:31] Colleen Stanley: Talk about the word love, and people might go, Oh, that’s too squishy for business.

[00:24:35] Colleen Stanley: Come on, people, who doesn’t need a little love? And I don’t think I’ve ever gone home at the end of the day saying my boss loved me too much. I got too much gratitude. I love the hard skills of training, and I know that’s what you specialize in, but never forget those soft skills.

[00:24:50] Colleen Stanley: Until AI takes over the whole world, I hope I’m gone by that time, but we’re not dealing with robots. We’re dealing with human beings there. That’s great advice there. Steven, do you have something to add?

[00:25:04] Steven Rosen: No. I’ve learned a lot from you, Colleen, as I always do.

[00:25:07] Colleen Stanley: So that’s why we do these. We’re teaching each other, which is always fun. And that’s the other quality. If you’re looking to be in sales leadership and you don’t find you like to learn, it doesn’t mean you’re a bad person, but great sales leaders create thought leaders.

[00:25:23] Colleen Stanley: But the only way you’re going to get into thought is to continue learning. With that, I will thank you for joining us today. And if you like what you heard, please subscribe. We’re going to be here every week for you. Thank you.


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