On a recent episode of The Sales Hunter Podcast, Mark welcomed Steven Rosen, veteran sales leader and author of Focused: A Leadership Discipline for Sales Managers Under Pressure.
Together, they explored why so many sales managers are overwhelmed, how to break free from the “spreadsheet jockey” trap, and what it takes to truly develop a top-performing sales team.
The Real Problem with Sales Management
Too many sales leaders are stuck in a cycle of chasing numbers without ever developing their people. According to Rosen, the problem isn’t a lack of talent—it’s a lack of the right system. “In most cases it relates to a poor system that rewards the wrong things. And two, you know, discipline, discipline fails in organizations.”
The real danger shows up when managers become service managers, jumping into every deal and answering every question, running themselves ragged and preventing their team from growing. Most training doesn’t stick, either. As Rosen put it, “Unless there’s an enforcement component, meaning the next level inspects sales manager coaching…the system defaults to minutia. It’s the urgent stuff, that urgent but not impacting sales, that gets addressed.”
Numbers Matter, but People Matter More
Sales leaders must know the numbers, but becoming obsessed with metrics is a sure way to lose sight of what matters: human connection and development. The best managers aren’t spreadsheet jockeys; they’re coaches committed to making their reps better every day.
“Your job is to improve your reps’ competencies, period,” Rosen explained. If all you do is look at dashboards and jump on urgent tasks, nothing changes for the better.
Observational Coaching: The Discipline Most Teams Miss
Telling someone what to do isn’t coaching. The real power lies in observational coaching—being in the field (or on Zoom), watching reps sell, then asking smart questions that help them self-evaluate. Rosen described it like this: “It’s moving from telling people what to do to asking them effective questions that get them to think and get them to self-evaluate.”
The win is getting reps to coach themselves, even when their manager isn’t around. That only happens when leaders resist the urge to rescue and, instead, force their people to bring solutions and take ownership. “If that’s a default behavior from the manager, well, guess what? The rep’s always going to escalate to you…You become, as I said, the server, the operator, as opposed to the leader, because that’s not leading.”
Ask, Don’t Tell
Most managers default to telling. But asking is the mark of a strong leader. Rosen reminded listeners, “Top sales reps ask good questions. So what happens when they go into a leadership role? It’s a similar skill…sometimes it gets lost in the transition.”
In practice, that means laser-focusing on just one or two areas for improvement at a time—not trying to “boil the ocean.” And when answers from a rep miss the mark, dig deeper. If they still don’t get it, ask permission to offer a suggestion rather than jumping straight into telling. Respect the process of helping them think through the problem themselves.
Enforcement Isn’t Dictatorship—It’s Consistency
One of the most provocative ideas in the episode is that of “enforcement.” As Rosen put it, “Enforcement is not about intensity…it’s about consistency. You don’t enforce with emotion. You enforce standards and expectations.”
That means inspecting what you expect. If the standard is coaching in the field 50% of the time, leaders hold managers accountable without resorting to fire drills or reactive energy. Quality can’t be measured in a dashboard, it requires time, discipline, and eyes on the ground.
Treat Salespeople Like Professionals
Salespeople aren’t “burger flippers.” They’re high-paid professionals who deserve to be developed, not just managed by numbers. By refusing to jump in and rescue, managers free up both their own time and their rep’s potential.
“If you want a team that can think and execute independently, the path is discipline, coaching, asking, and enforcement,” Rosen emphasized.
The Blueprint for Real Sales Leadership
This episode offered more than theory. Steven Rosen’s operating manual is a clear, actionable guide for every sales leader wanting to make the jump from reactive to proactive leadership. The main message: stop managing activities, start developing people. Build the discipline to enforce standards, invest in observational coaching, and transform the culture from “tell me what to do” to “let me think it through.”
The best sales managers don’t just hit their numbers. They build teams that get better every day on purpose.
Find Steven Rosen’s book Focused: A Leadership Discipline for Sales Managers Under Pressure on Amazon to go even deeper into the discipline of world-class sales leadership.
Mark Hunter :
It’s time you have an operating manual if you’re a sales manager. Yes, it is. Because I’ll tell you what, too many sales managers are flying solo. No, they’re not even flying at all. Hey, my name is Mark Hunter, the sales hunter. This is the Sales Hunter podcast with me today to unpack his new book. No, his operating manual, Steven Rosen. He’s going to talk to us.
Mark Hunter :
And the show begins right now.
Meridith Elliott Powell :
You’re listening to the Sales Hunter podcast with Mark Hunter where the focus is to help you as a salesman sell with confidence, confidence and integrity. And now here’s your host.
Mark Hunter :
Let’s get serious. What does your operating manual look like if you’re a sales leader? You’re. I hate the term sales manager. That’s why I use the term sales leader, because you’re leading an organization. It may be just one or two people, but you’re leading with me today. Steven Rosen, welcome. The author of the operating manual, Martin.
Steven Rosen :
It’s great to be with you and to chat about sales leadership. You know, the interesting thing is, you know, it is written to help sales managers where the biggest problem I find, and I don’t mean to pick on anybody, sales managers will definitely benefit on a day to day basis. But the next level of second line leadership really misses the boat and takes sales managers in directions that have no revenue generating opportunities. They’re calling them constantly, they’re creating new programs for them. So up and down the chain from the CRO to the VP of sales to the frontline sales manager, they can all benefit from having a greater discipline. And that’s what I talk about in the book. You know, it’s not a talent issue. Most people diagnose sales issues as a talent issue.
Steven Rosen :
And in my experience it’s, it might be talent once in a while, but in most cases it relates to a poor system that rewards the wrong things. And two, you know, discipline, discipline fails in organizations. And that’s really what we try to delve into and understand why sales managers are overwhelmed.
Mark Hunter :
Okay, I’m going to push back a little bit because I think there is a talent issue. And the talent issue is with the sales manager. Sales leaders themselves, they’re the ones, they’re the ones that have not developed because here’s the whole thing. If they have not developed, it’s going to be impossible for them to develop their people. And you hit it on the head also when you said they put out misguided directions, misguided priorities, all kinds of things like that. And then we wonder why sales organizations do not achieve their objectives. Okay, so why did you write the book? And let’s cut right to the chase. What’s the one thing that people are going to take away from this book and, and do differently as a result of it?
Steven Rosen :
Well, there are many takeaways, but we’ll narrow it down to one. What I kept seeing, and I’ve been at this actually I didn’t realize it’s been 30 years from industry to 20 odd years in my own business. And I focused on leadership for a majority of that time. And I’ve trained sales managers and realized that training in itself doesn’t necessarily do the job. So I’ve said In the last 10 years I will not go in and do a training program unless I can personally reinforce it. And that’s what I’ve done. And usually it’s three or six months that I’ll work with the managers to enforce coaching and then it hands off back to the next level of leadership, whether it be the head of sales or, you know, an rvp. And again, it crashes after I let go of the program.
Steven Rosen :
So what I’ve seen is a continuous pattern. And I kept, I keep scratching my head, how can I make it work? I don’t come from a training background, I come from a VP of sales background. So anything I do, the question always is how can I make it work? And really what I’ve realized is the next evolution, the piece, the missing piece, is enforcement. Unless there’s an enforcement component, meaning the next level inspects sales manager coaching, looks at their coaching reports, make sure they’re doing accountability meetings. Unless that’s happening, the system defaults to minutia. It’s the urgent stuff, that urgent but not impacting sales that gets addressed. So sales manager becomes a service manager. They service the reps, they go in and they rescue deals.
Steven Rosen :
They’re there when they get calls to respond immediately. So the best managers in that system are the responsive ones. Once I coach who are responsive, I yell at them because that’s the way I like to make a little bit of fun. But I said at the end of the year, if you don’t make your numbers, no one’s going to say that Johnny was the most responsive manager to emails because that doesn’t drive your business.
Mark Hunter :
Oh, okay, okay, you’ve said quite a bit there. I want to stop you right there for a second because what you just described could be the genesis for a spreadsheet jockey. In other words, I’m going to just manage the numbers, I’m going to manage the numbers. And I’m going to force it down to my people. And okay, now being a spreadsheet, I got to know the numbers. But if I’m 100% driven by the numbers, don’t I miss out on the nuance of what sales is all about? And that’s human connection.
Steven Rosen :
100%, Mark. I mean, the role, the ideal role of the sales leader is to develop their people to be better. It’s not. You know, so many managers get promoted from a. They’re a great rep, and what do they want to do most? They want to close deals, but that’s not their job anymore. Their job is about focus. And what focus looks like is doing the three most important things that drive sales. Number one is coaching, coaching and developing your people.
Steven Rosen :
It’s not spreadsheet coaching. It’s not deal coaching. It’s observational coaching. It means getting from behind your desk and getting out in the field or sitting on zoom calls. But, you know, you don’t see hockey managers managing from the dressing room. You know, they have tons of stats they can look at, but they don’t manage from there. They’re up on the bench sometimes standing up on the bench to watch what’s going on sometimes. So in the old days, which is when I was a regional manager, I was out in the field, and those were.
Steven Rosen :
Sometimes I wanted to. To be honest, I want to cut my wrist because the days were so bad, watching how reps sell. Actually, when I was a vp, I’d go out and I’d watch and think, oh, my God, my managers are not teaching them how to sell. But. But as a manager, your job is to improve your reps competencies, period. Yeah, there’s other things to do, but to me, if that’s not being done, all the other stuff does not contribute. And looking at spreadsheets, Covid, I think has created that, or the stacks and stacks and stacks of reports that we get and apps that we have actually prevent managers from doing what’s most critical.
Mark Hunter :
Oh, wow. Okay, I want to hold you up right there for a second because.
Steven Rosen :
Okay, Mark, you do that.
Mark Hunter :
You touched on a couple of things because just because it’s easy to measure doesn’t mean it should be measured. And I think this is what has created this whole metrics. I mean, metrics, metrics, metrics. But you use the term observational coaching. And again, because I hear salesman. Oh, I coach my people. No, that means you just told them what to do. You just told them what to do.
Mark Hunter :
That’s not coaching. No, it’s not walk through because again, you break it down in your book. You do a great job of it. Walk through. Help the audience to understand how you do observational coaching.
Steven Rosen :
Okay, well, I mean, as the word says, it’s being in the field and observing. So you’re hearing, you’re seeing what the rep says, you’re seeing what the customer says and then you’re able to help them self evaluate. Sorry, I said that loud. But the key is not telling. It’s moving from telling people what to do to asking them effective questions that, that get them to think and get them to self evaluate. Because the reality is even if you’re out there one day a month with each of your reps, maybe two, they’re still out there another 18 days on their own. And what you want them to do is ask the same questions that you’re asking them. How did it go? Did you achieve your objective? So it’s not about telling, it’s about asking them.
Steven Rosen :
And part of what I talk about when I talk about focused coaching, because I actually talked about focused coaching for probably 15 years now, it’s about only focusing on one or two areas that the rep is committed to improving that you focus on. You don’t focus on everything, you don’t change everything. But as a really good coach, if you’re able to impact one or two areas, meaning prospecting, closing, asking great questions and you’re able to improve that from, I don’t know, a three on five to a four and a half on five, then you’ve done a great job coaching somebody. Does that answer your question?
Mark Hunter :
Yes, it does. And again, I love, because the strategy that I think we have to embrace is you’re asking them questions because the idea is to get them to where they coach themselves 24, 7 when you’re not there. And so many times, observational coaching, and I see this all the time, managers just try to, hey, this is what you need to do. This is what you need to do. This is what you need to do. Because they, the manager want to look brilliant. No, ask the salesperson, ask the person you’re coaching, how do you think it went? Why? Why? What could you have done differently? And you getting them at? Why is it so hard to get that to be the adopted coaching development style people need to be using?
Steven Rosen :
I call it a paradigm shift. Because that’s the first thing that I teach. I call it a coaching mindset. So having a coaching mindset means being curious, not judgmental, asking questions, listening to the answers. Because what you Want people is to get their own aha moments, not for you to be the aha moment. And it’s a very difficult skill. But that’s the first one. If we’re, you know, training managers and a coach, that’s the first and most important skill because it applies to everything they do.
Steven Rosen :
You know, whether it’s self evaluation, you have to ask questions, whether it’s deciding what you want to focus on in terms of your coaching journey. Again, it’s asking questions. So it be it’s a skill. But the interesting thing is, or the funny thing is top sales reps ask good questions. Right. So what happens when they go into a leadership role? It’s a similar skill, right, of asking, you know, when you’re doing discovery, the best reps are the ones who do the best discovery, which means they ask good questions. So I don’t know, sometimes it gets lost in the transition. But what I have realized, I have a very, you know, it’s not in the book, but I have a way of.
Steven Rosen :
I don’t know if you know the Flintstones, but having two people talk on your shoulder, one saying, just tell them what to do, and the other person, no, ask, let them learn. So sometimes the devil, you know, wins out. But it really, as a manager, you need to be doing a lot of self talk. So in your own head, you’re saying, okay, let’s not tell them so it’s being conscious. Let’s ask.
Mark Hunter :
Okay.
Steven Rosen :
And in many cases, I’ll just. I have managers rate themselves, what percentage of time do you spend asking versus telling? And you know the ratio. Right.
Mark Hunter :
It’s sad. It’s sad because the vast majority are telling all the time, not asking.
Steven Rosen :
Yeah. And you know, the ratio is you have two ears and one mouth. That’s a pretty good ratio. Two thirds. One third.
Mark Hunter :
Yeah. But they don’t follow it. Okay, now let’s back the bus up a little bit. Because I’m a manager, I’m asking my people questions. I’m doing, you know, this, this focused coaching. And again, I love your approach. Don’t try to boil the ocean. Just focus in on one activity, one thing and get that changed, and then you move on to the next one.
Mark Hunter :
So that’s a, that’s a whole. That is a mic drop right there. But I want to, I want to pick on this. You ask questions. What happens when the salesperson answers them wrong? Oh, I didn’t. I thought it was a great call. I think, I think, I think the customer is stupid. I think the customer is stupid.
Mark Hunter :
How do I as a manager then coach through when my salesperson is not seeing the obvious?
Steven Rosen :
Yes. So sometimes, you know, the most challenging people, the ones who are not self reflective. Right. They’re the hardest to coach. And it requires greater depth of questions because sometimes we, you know, we always ask superficial questions at first.
Mark Hunter :
Right.
Steven Rosen :
And then we get an answer and we tend to move off as opposed to drilling down deeper. So I have a couple formulas that I use, you know, one to determine maybe which skill they focus on. And we do a forced ranking because forced rankings get things to fall to the bottom. But, but if the rep is just not getting it, you can, you can try to dig. And as my old coach, when I was in industry, used to say, if they don’t, sometimes they don’t know what they don’t know, that is a reality.
Mark Hunter :
Right.
Steven Rosen :
Sometimes they don’t want to think. And asking questions forces people to think. But I used to do it like this. You can tell as long as you deepen the learnings. Wow. Okay.
Mark Hunter :
Unpack that some more because that’s powerful.
Steven Rosen :
Well, sometimes, as I said, sometimes people don’t know what they don’t know. So what you want to do is sometimes you get to a point where you’re exhausting questions. You’re frustrated, they’re frustrated, you say. So one of the things that I use actually with clients. Can I make a suggestion? Okay. Because what that does is you open the person up, you know, you know, because telling feels, you know, it feels when people are telling you what to do. Let’s say, I know you have a wonderful spouse, but let’s say you’re supposed
Mark Hunter :
to take out the garbage now,
Steven Rosen :
you know, it’s. Or your manager’s telling X, Y and Z. So one of the things that you want to do in terms of coaching is it’s got to be an open communication. And sometimes what we default to is, can I make a suggestion? Can I jump in here? Can I share my observation? So if you’ve exhausted questioning, because questioning is good and it gets people to think because, you know, only 10% of people want to think. The rest think, okay, Stephen, just tell me what to do. I had a wonderful VP of sales who was one of the smartest ladies I’ve ever coached. And you know what she’d tell me most of the time, Stephen, just tell me what to do. And I’d say, why are you paying me if you want someone to tell you what to do? Maybe I’m not the right person.
Steven Rosen :
I’m here to help you think and work through your issues. But sometimes I default and give the answer because let’s say I had a little bit more experience. But that’s the easy route as a coach. It’s not the best route.
Mark Hunter :
Okay, so what happens if that customer, if that person says, just tell me what to do, because again, you’re trying to train them up for optimal behavior when you’re not around, and telling them what to do isn’t necessarily going to be the right way to do it.
Steven Rosen :
Well, here’s the thing I talk about in the book, and I think it’s a very important thing, because once managers, I call it rescuing. Whether you’re rescuing a deal, answering a question for a rep, it’s faster to do it that way, right? And sometimes it becomes a default behavior. And if that’s a default behavior from the manager, well, guess what? The rep’s always going to escalate to you, right? And then what you become is you become, as I said, I forgot what word I use. The server, the operator, as opposed to the leader, because that’s not leading. And I want managers thinking about leading, which is doing what’s going to drive the business. So you don’t want to rescue right away. You don’t want to jump in and give the answers, because what happens when it comes up the next time? And that’s where sort of that deepening the learnings is, the hope is that the next time something comes up, they don’t need to reach out to you. You don’t need to rescue the deal.
Steven Rosen :
So the concepts that I share in the book are to make your job easier, not more difficult. So the short term is maybe a little more difficult that you’re getting them to think. And one of the things that I share with managers, two things I share with managers, is one, when a rep calls you and they’re saying, oh, I don’t know, you know, Mark, I don’t know what to do. You be very kind and you say, steven, I’ll tell you what, why don’t you think about it for a few minutes, and when you figure out what to do, call me back and bring two solutions to the table. I mean, it’s not complicated stuff, right? But part of what you want people doing is thinking. Now, here’s a question that I always ask. I’ll ask you. You work with lots of salespeople, right, Mark? And lots of sales leaders.
Steven Rosen :
If I were to ask you, the salespeople that you work with, are they burger flippers? I used to be a burger flipper at Wendy’s hard job, to be honest with you. Or are they high paid professionals?
Mark Hunter :
They’re high paid professionals. Yes.
Steven Rosen :
So let’s treat them as such.
Mark Hunter :
Right, right.
Steven Rosen :
And by rescuing and by answering, the manager defaults back to what they did best. But they’re not helping the rep grow. And that’s really their job. And what I, what I talk about in focused is the system. I blame the system. I don’t blame managers. I think they’re working very hard. But their boss calls them, oh, what’s happening with this account? Have you not closed it up? And all of a sudden they’re, they’re scrambling to answer the reps, oh, I need your help to close this deal.
Steven Rosen :
And they’re scrambling. And then marketing says, oh, we have a new program to roll out. We need you on this teleconference. None of those drive performance.
Mark Hunter :
Yeah, yeah. It becomes total reactionary. Okay. Yes. Trap, let’s deal with this issue. Because you brought the word up a few times. We only got a few minutes left. How do we, how do we enforce? Because there comes time, we gotta.
Mark Hunter :
I don’t want to say drop the hammer, but. Drop the hammer. Yeah.
Steven Rosen :
So it’s interesting because when I first, I didn’t coin the word, but I started using the word enforced leadership. And I’m telling you, you get resistance even from the senior leaders. Right. It’s enforcement. That sounds like dictatorship.
Mark Hunter :
Yeah. Right.
Steven Rosen :
And enforcement is not about intensity. I know. I mean, I can be intense. It’s about consistency. You don’t enforce with emotion. You enforce standards and expectations. So I’ll give you an example. You know, if the managers, the expectation of the managers is to be out in the field, let’s say 50% of the time doing observational coaching.
Steven Rosen :
And you’re the next level, taking it from the leadership perspective. And you’re sitting down with your manager and they ask you, okay, how’s it going with coaching? Actually, I want to circle back to one other thing. If you. And you know, how many days have you been out this month? Because I used to track that when I was a sales leader, you know, and if, Well, I was only out two days because I was busy. That’s probably not a good answer and requires some enforcement and redirection. So if you don’t mind, Mark, I know we’re short on time. There’s just one point that came to mind before when you talked about dashboard management and my, you know, I try to think of things very simply and I look at success in sales as a combination of quantity and Quality. It’s a very simple formula.
Steven Rosen :
How many calls you make versus the effectiveness of each call. So the number is very easy to manage. You have tons of metrics and dashboards to measure. The quality component can only be done through observation. That’s. That was the point I wanted to make. Because it’s both. It’s not just one or the other, but it’s both.
Steven Rosen :
But what, what gets missed is the observational, the quality control, the quality view of the sales rep.
Mark Hunter :
I love that because oftentimes that’s the piece that takes more time. Hey, we’ve been talking today with Steven Rosen, author of the book Focused. Give us the full title. Give. Give us the full subtitle because I. Because I love your subtitle.
Steven Rosen :
Okay. I’m gonna actually bring it up because it’s a. It’s a mouthful. Visual visuals are good. It’s a leadership discipline for sales managers. We didn’t talk a lot about under pressure, but, but the under. Most managers are under pressure. We’re close to the end of a quarter.
Steven Rosen :
Call up most managers and ask them, are they out coaching this week?
Mark Hunter :
No, they’re all trying to close deals. Right, right.
Steven Rosen :
And the message that I have, I’m going to read it out to you. Whatever does not hold under pressure was never enforced. And leadership’s real job is making sure things that are critical hold.
Mark Hunter :
Hey, what you’ve got is truly a blueprint. It is a workbook. It is a fundamental guide for anybody in a sales leadership position. And what I like about it is it’s written by somebody who has been in a sales leadership position position not just for a few months, not just for a few years, but you spent your lifetime in that space. So, Stephen, thank you. Where do people get the book? How do people get in touch with you?
Steven Rosen :
Okay, so number one, the book is on Amazon. The easiest place to buy it. You can get it in paperback. You can get it as an ebook. I can be reached@steven starresults.com My website is www. Starresults.com or you can find me on LinkedIn, which I tend to spend a bit of time on. But those are the key areas you can find me.
Mark Hunter :
Hey, great. Thank you for being with us today. Steven Rosen, you need to pick up the book. If you’re in a sales leadership position, you gotta just go into Amazon, type in focused. Steven Rosen is going to come up. You got to get your copy right now. My name is Mark Hunter, the sales hunter. Two episodes a week, one like this, where we do a deep dive with a subject matter expert.
Mark Hunter :
Second episode is just me single topic where we just unpack and give you some tips you can run with. Why do I do the show Is to help you see and achieve what you didn’t think was possible. While you’re picking up focus from Steven Rosen, make sure you pick up integrity for selling, of course. That’s my new book out there. And with that, we want to say thank you very much and great selling.
Steven Rosen :
Thank you, Mark.
