Behind the Boardroom · 2026-08-25 · 53 min
Key moments - from our scoring
Substance score
42 / 100
Five dimensions, 20 points each
Keith Rosen, a global authority on sales coaching and author of Coaching Salespeople into Sales Champions and the new book Crucial Coaching Conversations, sits down with Jason Cooper to examine how leadership and coaching have evolved dramatically over the past 18 years - particularly in response to AI, pandemic disruption, and massive shifts in how companies buy. The core insight: managers remain trapped in outdated behaviors, still solving problems instead of developing people, still avoiding the difficult conversations about personal values, work-life balance, and the fears driving their teams. Rosen introduces the concept of 'enrollment' - a language of leadership that requires setting positive intent before coaching begins, moving beyond transactional discussions of quotas and results to address the internal narratives and uncertainties keeping people stuck. He challenges the myth that AI will replace human salespeople, arguing instead that AI is a tool to be coached, not a replacement for human presence, authentic relationships, and strategic communication. The conversation also explores group coaching in team meetings as facilitation, where leaders ask questions rather than provide answers, and the prerequisite for building true coaching cultures: leaders at every level must themselves be coached, from the CEO down.
Managers don't currently know how to coach AI because they confuse training someone on how to use a tool with coaching them on the mindset and fears around it; the gap is coaching the emotions, uncertainty, and internal narratives people experience with technology, not just the mechanics of prompts.
Enrollment is the art of setting positive intent before coaching begins, where a leader opens a conversation by explaining why they want to talk and what's in it for the person being coached, creating psychological safety and reducing fear when intentions are unclear.
Managers have never been taught how to have these conversations and default to activity management and problem-solving; they also lack permission or modeling from their own leaders, making it feel outside their role despite the fact that personal priorities directly affect performance.
Group coaching is facilitation, where the leader spends about 20% of time pouring foundational knowledge and the remaining time asking questions and creating dialogue, rather than telling; the goal is helping the group solve their own problems through peer coaching and cross-functional conversation.
When managers don't explain the why and what's in it for their people, a universal law applies: people default to fear, uncertainty, and misinterpretation, which drives urgency, disengagement, and lack of focus instead of leadership-driven clarity and alignment.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains a handful of genuinely useful operational ideas - the three-question pre-coaching form, the observation that managers lack frameworks for coaching fear or AI adoption, and the insight that companies use call-recording AI on reps but never on managers - but these are buried under long stretches of affirmation, anecdote-swapping, and motivational filler between the two speakers.
Are companies using the same technology to record their managers be then evaluated by the same technology they're using to evaluate their salespeople? I have not heard of one company that's doing that yet.
How can I coach you on something that never happened?
There are a few genuinely interesting reframes - the two-part model of fear, the idea that urgency is a symptom of absent leadership rather than external pressure, and coaching AI as a distinct competency gap - but the bulk of the episode recycles widely-circulated coaching doctrine (people don't leave companies they leave managers, align personal and professional goals, etc.) without meaningful extension or challenge.
there's actually two parts of fear. There's that which we fear, and then there's the feeling of fear.
Urgency is what happens when leadership is not present. Urgency is the pressure that everyone is putting on themselves, not coming from our clients.
Keith Rosen has genuine, long-tenure practitioner credibility - 18 years building coaching frameworks, verifiable global deployment, and a real published body of work - but he operates squarely in the consultant-author-speaker category rather than as an operator who scaled a sales org, making his authority advisory rather than earned through P&L ownership.
having traveled to 76 countries and six continents, millions of salespeople and managers. I've had the opportunity to make an impact.
my first edition of Coaching salespeople into Sales champions was written 18 years ago
The episode is almost entirely abstract: coaching philosophy is discussed at the level of principle with no named client companies, no outcome metrics, no before/after conversion data, and no timelines beyond biographical references; the one stat cited ('76% of companies have changed the way they buy') is dropped unreferenced and never elaborated on.
76% of companies have changed the way they buy and the priorities.
I went from having a longer pre call form that I would have managers share with their coaches to just three questions. And the questions are very simple. What are your wins from the last conversation we had? What are your challenges? What do you want to use our time for?
The host frequently takes long turns to share his own opinions and anecdotes rather than drawing out the guest, questions are broad and open-ended with little follow-up pressure, and there is no productive disagreement - both speakers affirm each other throughout, resulting in a collegial but unchallenging chat.
So what do you think about, uh, team or group coaching in a scenario, uh, in a meeting as an example?
And I. It's so often misaligned in that area, and I don't think it's congruent. And I don't. I, um, haven't seen it that often where everyone is in that full coaching.
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of Behind the Boardroom, host Jason Cooper welcomes back globally recognized sales leadership authority Keith Rosen for an insightful conversation about humanizing leadership in the modern business era. Drawing from his latest book, *Crucial Coaching Conversations*, Rosen breaks down how managers must shift from simply managing activity to adopting coaching as a language of intentional communication. The discussion navigates the fast-paced evolution of AI and technology, emphasizing that while tools can surface performance data, they lack the "heart" and empathy required to truly connect and mitigate employee fear. Key takeaways from the episode include exploring the "art of enrollment" to align personal priorities with business objectives, understanding how to coach through mindset assumptions rather than managing future-based fears, moving away from the toxic habit of being a "chief problem solver" to scale team independence, and implementing a holistic 360-degree coaching culture where everyone - from the CEO down to cross-functional peers - remains coachable.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Hello, good morning, good evening and good afternoon. And wherever you are in this wide, wonderful, beautiful world, you are very welcome to the global Sales Leader podcast. I am your host, Jason Cooper. Every time that I have these conversations with exceptional people to help people grow and have that ripple effect going forward. So I'm always fascinated by the behavior of people and also how we can learn and grow within ourselves. And we know that coaching is one of those fundamental things that we should all be doing. And Keith Rosen, I've actually chosen him back again for the third time to have on my podcast because I think we make exceptional conversations. Um, we have a theme behind it. So Keifer, I'm absolutely delighted to have you here again. I'm going to give you a little bit of a synopsis again for people that uh, have short term memories like me. So Keith is a global recognized authority in sales leadership and coaching and a pioneer in helping organizations build high performance coaching cultures. Easy for me to say. He's worked with some of the world's leading organizations and was in Ireland a, uh, couple of weeks ago and I miss him. Uh, anyway, that's another conversation itself. Help himself lead the shift from managing activity to truly developing people, but also to help them change and think about themselves. He's also author of the best selling book Coaching Salespeople into Sales Champions. A tactical playbook for managers and executive who want to build teams that just don't perform but consistently outperformed. So at the hearts of Keith's philosophy is a simple but overlooked truth. Training develops salespeople, coaching develops sales champions. And his work is, and he has a new book and um, we are going to be speaking about that today. Crucial coaching conversations. He brings this to life in the concept of connection, accountability and what he calls the art of enrollment. I'd like to hear about that, uh, uh, the ability to create conversation and generally inspire ownership and behavioral change. And that's what I've already spoken about because of Keith's heart. The culture, performance and results of any team are ultimately shaped by one thing. The quality of the conversation, the quality of the questions and the quality of what they're actually saying are uh, willingness to lead leaders or willing to have, and I always think is you can challenge them. But it's also about their own internal dialogue to themselves. And if they get that buy in to themselves, but also for the leaders to have that buy in to consistently want to train or coach their people. Let's talk about that because I know from our previous conversation, uh, this is going on a little Bit left wing. This typical of me. You helped create, um, the icf, which is the International Coaching Federation, many moons ago. So from that inception to where we are now in coaching, what do you think has changed over the last 16, 15 years? 18 years. I got it right from my notes, um, when you started doing all of this and for your first book, and that's a big open question there.
Speaker B: So uh, let's just backtrack. So uh, you had mentioned, you know, with uh, kickstarting critical conversations. The good news is I've actually pulled out some great mini books from my new book so people can get some free excerpts on, on my website on that one. And as you know Jason, uh, having known you for many years, my first edition of Coaching salespeople into Sales champions was written 18 years ago. 18 years ago. And from there, ah, and being very grateful and blessed that this has been truly the milestone and the foundation for not only, um, universities, uh, but also for global organizations in terms of how they're developing managers and world class teams. Uh, that started my journey around the world and I was blessed to have traveled to uh, 76 countries and six continents, uh, millions of salespeople and managers. I've had the opportunity to make an impact. And, and over the years and through my travels, I, uh, very quickly realized that especially here we are 18 years later, you know, through a pandemic, through all the chaos that's happening in the world with this acceleration of technology and AI, I was compelled that I needed to really upgrade my message, uh, from a place not only of strategy, um, but of thinking of, of conversation. You know, if managers are still selling, uh, and salespeople are still selling and managing the way they were doing it, you know, five years ago, three years ago, they're already set up for failure
Speaker C: because 76% of companies have changed the way they buy and the priorities.
Speaker B: And you were saying before about motivating people. Today, the priorities, the values, um, the, the things that matter most for people have change dramatically. And if managers and leaders have not evolved to the point where their people are, they're just going to keep them stuck in mediocrity having the same conversations that happened before, rather than what today is something that managers struggle with most, which you allude to. This art of enrollment is a language of leadership. It's sort of like if you're learning French or Italian or Spanish. I coach leaders and salespeople to learn the language of coach. And it's not something you do to someone and it's not something you say okay, I'm going to put my coaching hat on. It's how you show up as a human being. It's how you communicate at a higher level. It's shifting away from being, you know, just, uh, being strategic, which many managers are, to being a strategic communicator and communicating with intent. So when we talk about all these fears out there, you know, people fearing being laid off, uh, people fearing job security, uh, you know, how they're balancing their life, you know, these are the conversations managers aren't having with their people. They're not taking the conversation and moving into their personal life. I mean, after all, look at where we are. I'm in your home, I'm in your office, you're in my office. You know, just by default, we can pick up a million things to chat about. We've never had this level of deeper exposure into people's lives than we do now. And, and yet still, salespeople, and especially managers are not taking advantage of that. And I don't blame them if they've never been taught how to do this. This is not something innate. How would you begin a conversation that sounds like, hey, Mr. Or Mrs. Direct Report? You know, I know we've been, it's been a wild ride this year. There's a lot of chaos, there's a lot of uncertainty. I would love to talk to you and see how I can best support you so you still feel, feel connected to the team, to your goals, and to me.
Speaker C: And then that's language of enrollment is setting positive intent. And then from there, the coaching begins.
Speaker B: So how do you balance your day? How do you separate your personal goals with your goals at work? How do you turn off, uh, work at the end of the day so you can be present with yourself and with your family and with your children and not have your phone right next to you? Uh, how do you, how do you structure your schedule so you're putting your self care as a consistent daily part of your regimen? And one thing that gets thrown out since, you know, I've heard from the pandemic, is, oh, Keith, I used to be so regimented with my self care, eating healthy, exercising, and that got thrown up. So it's really, it's not only reevaluating our business, but before we even do that, we need to reevaluate our lives and our priorities. And managers need to understand I need to wait. I need to pull people's core values out. I need to pull out their priorities. Uh, I need to help them with their personal goals, too. Not just throw them a quota. Yes, because that's what the greatest leaders are doing. They're making a transformational impact by building deeper, more meaningful relationships than they ever had to before.
Speaker A: Yeah, I think absolutely. And that is absolutely core. But the challenge is, from what I've seen is there's huge amount of pressure going on to the managers now, even more so than ever before because of the layoffs that are actually uh, because of AI coming in and maybe streamlining processes and doing this, that and the other and high levels of cortisol in the manager or the leader, whoever he is, because he's given a lot more stuff he needs to do now and maybe doing more firefighting, maybe doing. I know this is probably a common theme that's happened over the years, but I think it's even more um, up to fruition nowadays just because the advent of all these technologies coming in and stress. So I think a lot of the time, and this is where we're going to carry on, allude to is um, if they're doing so much firefighting so much, they're not spending enough time with their team to help them to find out what they want. Uh, and as you said, wellness is so very important now. The best performing sales people are a lot more calm, uh, without the added stress. I think there's some good stress to have as we all know, but there's also some bad stress to have. But I think without, we do thrive on a bit of, of that so.
Speaker C: Well, I always like to change the
Speaker B: word stress to inspirational motivation. Jason.
Speaker A: Yeah, yeah, a uh, good reframe into that and I think you can actually balance that. So I, I, I unpacked a little bit of what you've said, but with the advent of AI now and I think you said that and I've said that and we said that beforehand. Where do we go from here with this AI stuff that, that is in place? Um, is it shortcutting stuff? Which I think it is and it helps to hopefully make our process a little bit more streamlined. But are we hiding behind it as well?
Speaker B: Yeah, yeah. You know, I'm looking here at my table of contents and uh, you know, the first section, the first uh, two chapters is about the abrupt evolution of business based on AI. And of course by the time people read this, it's probably going to be
Speaker C: outdated because technology is moving forward so fast.
Speaker B: But which is why I wrote it from an evergreen perspective. I didn't write about AI and how it's impacting how we work from a place every day and how we can technically use it every day, because that's part of what managers need to do in training people. That where every leader is missing the
Speaker C: boat is just like in any core
Speaker B: competency, once you train someone how to use something, how do you then shift to coaching them?
Speaker A: Yeah.
Speaker B: So the miss is not only, you know, people running around and even managers saying, uh, I don't know how to use this. No one taught me how to use this. And then my m. People are coming to me with like, these clearly written,
Speaker C: you know, emails that were clearly generated by AI. Do I just tell them do it again or rewrite it?
Speaker B: Managers don't know how to coach to technology. They don't know how to coach to AI because these are different conversations. Just like when you talked before about uncertainty and fear. Managers don't know how to coach uncertainty and fear because those are feelings.
Speaker C: That's the internal game, as you said, the internal narrative. Managers, if they're even good at coaching,
Speaker B: are great at coaching strategy, are great at coaching results, are great at coaching solutions and collaborating, if done correctly.
Speaker A: Yeah.
Speaker B: But when it comes to shifting mindsets, and quite frankly, I, you, uh, know, in, in fairness to managers, if they're not getting what they need, it's very difficult for them to recognize what their people need. So, you know, when, when to me looking at AI, you know, to, to eradicate the fear that many people feel like this is going to take over their job, uh, it's really about marrying technology with humanity.
Speaker A: I agree.
Speaker B: And, and if we can do that and this way, my son, um, who's, you know, studying, uh, machine learning in college, he won't yell at me this way. He's like. Because he's, he's scared of what AI can do. And, and as you know, you and I were discussing offline is, you know, AI is a great tool to supplement. Write an article, write a blog, write
Speaker C: a post, write your business plan, then put it in there section by section, challenge it with certain prompts.
Speaker B: And that's the one thing that I
Speaker C: find so interesting because there's still such
Speaker B: a lack of understanding of what AI is and what it can do. And you see all these posts out there.
Speaker C: Oh, I can. You can generate a million leads while you're sleeping and close 10x times more,
Speaker A: you know, that I can smell.
Speaker C: Just ping me with you want it and I'll send it over to you. Like these people, you know, automatically have cracked the code, right? All these thousands of people at the
Speaker B: same time, ironically crack the code.
Speaker C: Sorry. Clearly we hit A nerve on this one.
Speaker A: Yeah.
Speaker C: But the thing, what people don't realize is all they're sending you are prompts. They're not sending you the solution for you to sleep, wake up, and there are 20 leads in your inbox. And if they can learn how to
Speaker B: write prompts, guess what? So can you.
Speaker A: Absolutely. And you like me. And probably thousands of millions of other people will get a message, um, in their inbox saying, hey, Jason Cooper, the sales relationship coach, blah, blah, blah, blah, blah, and go, oh, come on. Uh, this is. And I, I sometimes reply and I challenge them. I said, I'm happy to have a conversation with you, but before we get through to that, I'd love to coach you on how to communicate with people a little bit more effectively. How about that? Here's my calendar link. Happy to have a conversation. So I always flip the script when I can be bothered to do it, but not all the time, because I. Some of it, we miss the subtle art of, uh, human connection and people skills. We've gone beyond soft skills, and I think it's people skills on the subtle art of communication. And this is where our, um, managers come in and our leaders come in to coach. But also, I always think it's gotta be a complete coaching culture, uh, and that's gotta come from the very top, all the way down to every single person. The CEO needs to be coached by someone. They need to coach their marketing, sales, uh, whoever else, uh, and then it's, uh, spiral down or sideways or wherever.
Speaker B: Oh, let's put a pin in that one because that's certainly, uh, worth unpacking there. I just want to close the loop on just mentioning some other things that we were talking about. AI. You know, one thing people have to realize is that if the dominant leadership strategy today is care, and the dominant sales leadership strategy is care, AI doesn't have heart, so it will never have heart. And when you're in front of a company, you're not saying, hey, I have a great present to share with you. Hold on, let me open up my AI.
Speaker C: And they're going to present it.
Speaker B: No, human beings are going to present it. And it goes back to what you said earlier, the lost art of communication. You mentioned it within the first three minutes. The greatest salespeople are the ones that communicate at a higher level.
Speaker C: They have a stronger presence. Their confidence is high, and it's unconditional. They're not feeling being threatened by technology because they know that they're staying a
Speaker B: step ahead of it. They're responding, not reacting. And just to one final thought about this. Uh, and because it's so recent, I just wrote about this. You know, urgency replaces complacency.
Speaker C: Urgency. Urgency is what happens when leadership is not present. Urgency is the pressure that everyone is putting on themselves, not coming from our clients. And without, without leadership, it's urgency that
Speaker B: creates the fear, the unknown, the, you know, the lack of guidance, um, the lack of focus, the lack of engagement that we're, we're all missing, that we desperately need.
Speaker C: And that has to come from the leader. I mean, after all, after, you know,
Speaker B: a boat goes through a storm, the, you know, the captain needs to recalibrate
Speaker C: and renavigate to make sure all his
Speaker B: people are rowing in the right direction.
Speaker C: Well, that often doesn't happen if you're in a state of reaction versus a
Speaker B: state of being responsive. And the one thing to wrap this final part up is as we're talking about all these different conversations and how critical it is for managers not just to share, hey, here's what's going on, but here's why, and here's what's in it for you to really connect a, uh, deeper understanding of why people are doing what they're doing, not just what they're doing. When managers do that, um, it mitigates the fear when managers don't set intent. It's a universal law I share. When intentions are unclear, people default to fear.
Speaker A: Yeah. Uh, funnily enough, um, a couple of months back, two or three months back, I was coaching a manager to be a coach. And, um, I gave a Sir John Whitmore book for him to learn from it, uh, just to read it, uh, after I had the session, had a couple of two or three sessions with it. And my challenge was, um, we've just spoken about it. His manager, who was the senior leader, wasn't coaching any of the team at all. He was canceling meetings. And he would just sporadically have the. And it was a nightmare. And funny enough, I was supposed to have a meeting with him today, and he's done this several times for me, and I'm just going to pull him out and, um, not going to have it. It just cancels meetings with no reason, nothing behind it. And he's done it to me several times. And imagine they does that to all of his team as well. He has several different teams and he canceled them with. Doesn't, uh, explain why and doesn't give anyone context. So he just carries on with his work life, but he doesn't really care about his team, but he does but the, the person that I tried to coach, um, it fell flat because he just didn't sit because no one in the else in the organization wasn't coaching. So it was almost like a waste of money and time and effort on my side.
Speaker B: Yeah, yeah. And clearly, uh, just, you know, to me, I always say to leaders, you know, your job is complicated enough. Mine is to make it easier for you. Um, there's the what's going on now let's look at the why. Okay. It's for the last 34 years of me doing this. The concept of managers always being the chief problem solver is a global pandemic. And it's endemic in every company's culture, regionally, as well as the location of the company, wherever they're based. Because managers feel they must solve problems to move forward. And their inner narrative. If I solve it, I know the answer ego based. And if I solve it, it's going to be quicker. Okay, but now let's look, uh, three months ahead, six months ahead, nine months ahead. When you have three direct reports, six direct reports, nine direct reports, then you get promoted to management and now you have layers of people you're responsible for. You can't have a line of people outside your proverbial door looking for answers from you because you cannot scale dependency. The goal of every leader is to make their people more valuable, to build future leaders of the organization.
Speaker C: So, you know, to drive this home. It's, it's not that managers are stopping being the chief problem solver. They're just solving new problems that didn't exist before. Which goes back to, as we've been
Speaker B: talking about, the whole entire premise of, uh, if managers can just make that shift and take that step back and just stop and seek to understand someone's point of view first before throwing out an answer, it will change the conversation dramatically.
Speaker A: So what do you think about, uh, team or group coaching in a scenario, uh, in a meeting as an example? Because what you want to do is give people the opportunity to show up, but actually think of ideas and solutions rather than as exactly what you said. If you're having a meeting and you're telling, as we know, old school thing that I was always taught, telling isn't selling, uh, always stuck in my.
Speaker C: A hundred years later and sales still hasn't changed. Right.
Speaker A: Yeah. Uh, so what do you think about collaborative group selling? Not training, but group, uh, in team coaching, uh, in the team, whether it's 3, 5, 10 or whatever it might be.
Speaker B: Yeah, you know, it's, it, it's to me, it's the evolution of just really learning how to coach one on one. Uh, to me, coaching in a group or coaching a team during a meeting. And by the way, lots of different variables, different scenarios. So this is not an absolute, uh, I, I, to me, coaching when you're in front of a group is facilitation. And if you're facilitating, that means you're asking questions. So if I'm in front of a group, I'm probably spending maybe 20% of the time over two days just pouring a foundation of what they need. And then either they're going through skill builders coaching themselves, um, or we're having a dialogue. So, you know, back to your point. And again, this, this is, you know, not, not an absolute, uh, but let's say I'm going out and I'm, I'm working with a company and they have, let's say, you know, 20, um, 20 managers. And I'm just saying, let's say 20 salespeople just to keep it ground. And the person enablement or the VP would come to me and say, okay, Keith, let's go through the logistics. I, uh, have 20 salespeople. I have 20 managers. I know that. You know, we want our salespeople trained in coaching because the best salespeople now are actually coaching customers. That's the evolution. But here's the thing.
Speaker C: Do you think we should put our managers in the same course together with the salespeople?
Speaker B: Because not only the salespeople are going to be in there and their managers,
Speaker C: but then a couple of the managers.
Speaker B: Managers are going to be in there. And I stop and I say, you know, that's a really, really great question. Remind me again why you're hiring?
Speaker A: Yeah, yeah.
Speaker B: Well, Keith, I'm hiring you because, um, we want to break down department silos. We want to build a deeper level of trust and engagement. We want to foster more healthy collaboration. We want to, um, be able to have more meaningful conversations, uh, deal forecast, pipeline reviews that are going to become revenue accelerators, not just wasted conversations. Um, we want to make sure that at every level people are being coached. Where managers are coaching up, salespeople are coaching their peers, salespeople are coaching up, managers are coaching their salespeople, peers are coaching peers, people are coaching cross functionally. I say, that's really interesting and I would stop. All of a sudden the light bulb goes off.
Speaker C: Oh, I get it. If we get them all together, we're achieving our goal of collaboration, breaking down silos, building trust killing assumptions. And then the Salespeople are going to coach their manager and their manager's manager. If you really want to build a
Speaker B: healthy coaching culture, that's what's happening. And that really is a great barometer to look at your culture in the mirror and say, do we really have a true coaching culture?
Speaker C: Because that's what it means.
Speaker B: Everyone is speaking the language. Everyone is coachable. Everyone wants to be coached because they see the value.
Speaker C: And again, are there times when I
Speaker B: break up salespeople and leaders?
Speaker C: Sure.
Speaker A: Ah.
Speaker C: And they mean I have nothing to do with that or changing the dynamic in the room.
Speaker B: It's just based on what we need to cover.
Speaker A: And again, I think it still needs to come from the top down, but then everyone needs to get that buy in to actually wanting to be coached and knowing the outcome. Uh, if you are coached, what will happen once you're done coaching correctly is you're going to see some change. When I ask you questions that I always like to use, the Pareto principle is 20% asking questions you're answering 80% of the time. And I've been listening 80% of the time to what's actually been said. Uh, so I can respond with another question and another question. And I was doing that earlier on today with a client and I go, well, today what we're going to do is just pure coaching. And I need to find out where you feel about certain situations. And I was trying to touch on a few of the behaviors behind what he said kept drifting off and I had to keep pulling back and drifting off and m. Keep pulling back. But. And that's what we do when you're being coached. But as long as they got that buy in and they're there to want to be challenged in what they're doing right now, to change their behaviors, their attitudes or whatever it might be to help them to get where they need to be going. And it is buy in from the whole of the community within the organization to help them.
Speaker B: It's very interesting. And just building off that on, uh, many instances I've heard managers say after two days of training and we're talking about enrollment and setting positive intent, and one of the conversations is about enrolling people in coaching. So they want to be coached and understand what coaching is and understand the value they're getting. Unfortunately, a lot of managers don't take the time to do that. And again, why? It's not because they don't want to. It's not because they don't see the value.
Speaker C: It's just not inside their line. Of vision.
Speaker B: They don't know what they don't know.
Speaker C: So let's face it, if you were
Speaker B: a salesperson in another company and you had a really toxic manager, and as we know, people don't leave companies, they leave managers. Uh, cultures.
Speaker A: Yeah.
Speaker B: Now you have this man salesperson carrying
Speaker C: their baggage because they're all carrying baggage into their new organization.
Speaker B: And the manager is excited about their new hire and they bring them in for the first coaching session. They start coaching them and the person is just cold sized. The manager is asking good questions. Person is just providing yes or no answers. And of course the manager's thinking. They're thinking, you know, I feel like this person's just telling me what they think I want to hear. Now, the manager can understand what's going on, but they're not getting to the root cause. The root cause is that salesperson took their old manager's face and put it right on you, thinking, oh, well, that's how I was managed. That's how you're going to manage me as well. The only way you can break that cycle and create a new possibility is by hitting the reset button. And that could sound like, hey, Mr. And Mrs. Uh, rep. What I want for you is to be able to build a thriving career where you're hitting your personal goals and achieving what matters to you.
Speaker C: And I have no idea of your
Speaker B: past experience being coached, whether it was good or bad. I would love the opportunity to just sit down with you, uh, talk about what coaching is, how it could be beneficial for you and my role in supporting you, because after all, I'm trying to be a better coach for you. So this journey is reciprocated. It goes both ways. And I'm going to be looking for some observation and coaching from you as well. So would you be open to setting
Speaker C: the parameters and the guidelines of how
Speaker B: we can work together in a collaborative, trusted way? And I can be the best coach for you?
Speaker A: Yeah. Yeah.
Speaker C: The only managers, Jason, that are saying that, and I am not saying this
Speaker B: to be presumptuous, are the ones I train.
Speaker A: Yeah. Yeah.
Speaker C: Because they don't do this.
Speaker B: They play the power card. Here's what we're doing. Why Mr. And Mrs. Manager? Because that's what I was told. So that's what we have to do now. It's part of our KPI, part of our scorecard.
Speaker A: I think that is part. And it should be part of your KPI to coach as well as. So, uh, leader, manager, whatever has to be 70%. That's the KPI. That's the revenue, blah blah blah. The other 30% or 20% has to be a KPI on how many times that you are actually coaching your team, your people, and maybe uh, in retrospect as well, how many times you're being coached as well. That should all be taken down because it's great and wonderful that we go into organizations, but what happens when we leave?
Speaker B: Well, isn't it interesting that companies spend all this time and all this money on some really, really powerful and valuable technology where you can have reps, uh, do a presentation or have a meeting and not only can you record it now, but you know, through AI, they, you can actually decipher their tonality, their confidence.
Speaker A: Who spoke the most?
Speaker B: Were the quality of questions good?
Speaker C: I uh, mean really, I mean basically AI is doing what all they're doing
Speaker B: is unpacking coaching opportunities. Then, then the human part kicks in.
Speaker C: But here's my point.
Speaker B: Are companies using the same technology to record their managers be then evaluated by the same technology they're using to evaluate their salespeople? I have not heard of one company that's doing that yet. I truly hope that your audience is hearing this as a wonderful opportunity to accelerate growth and performance.
Speaker A: Mhm. I think the likes of Gong and even the transcript of this recording we can take out via AI now all of the main points. And that's why I generally would do on a meeting, if I'm in my meeting, I would pull that out and I would do it because no one's coaching me to do it. I have to coach myself by the AI to see how many times I'm asking really good questions, am I listening? How many times are they responding in the right way? And because I'm a self, uh, I'm an entrepreneur myself, I've got no one else to coach me. I would need someone like yourself to coach me to be better at what I do because otherwise it's just rattling around in my own head. Uh, so sometimes we need to be taken out of our comfort zone and we need to be pushed a little bit more forward than we've ever done before. Because it's all about progressing and being outside of your comfort zone. Whether uh, uh, one of your sales team are coaching you, that's really pushing yourself outside of your comfort zone. That's something I'd love to see. Uh, because it is a flip. You have to move the uh, ego out as well. Because feedback is absolutely imperative for us to all to learn and grow and get better at what we do.
Speaker B: Absolutely. And I Hope that, uh, companies, uh, are realizing the three things that I hope I never hear from again, that just give me agita. Number one, I want to create a feedback culture.
Speaker C: No, you don't, because that means you're just going to run around and tell everyone why they suck.
Speaker A: Suck.
Speaker C: Okay, not gonna work. Oh, this person, I want to manage
Speaker B: them or coach them out.
Speaker C: No, you just position those as negatives. So you're gonna coach them in or coach them out. How about this? I want to support this person unconditionally
Speaker B: and then make the choice whether or not it's a fit for them. Okay, so, and again, those things are, it's, and of course I'm, I'm being, uh, overly dramatic. But the point is, when I hear
Speaker C: those things, managers aren't taking the time
Speaker B: to even think about what, what they're portraying out there and how they're presenting. Coaching. It's, you know, coaching is not. If again, managers aren't, um, you know, it's, I always find it funny. A manager might come to me and say, hey, Keith, you know what? Um, you know, I, I, I, I have, you know, I took a course and, and I went out and I started coaching everyone. And out of my 10 salespeople, only one is coachable.
Speaker C: What's really easy for me to break down.
Speaker B: It's not about your team. It's about the manager and their enrollment. I coach them, they go enroll people.
Speaker C: Keith, I can't believe it. Everyone is bought into coaching.
Speaker A: Why?
Speaker B: Because you've aligned their personal priorities, values and goals with what you need for them to achieve at work. If I can align and hey, what I want for you is to get that promotion. What I want for you is to get that end of the year bonus. What I want for you is to be able to put money on down payment on that house, you know, or car. What I want for you is to get that new toy. What I want for you is to be able to travel less.
Speaker C: These are things people want if you're taking a stand for them. And here say, listen, if you want this, here's what we need to do at work. You're in because you now have a
Speaker B: line that personal goals with business objectives. So now everyone has a shared North Star, a guiding light to focus on. Not just, okay, when I get here, I guess, you know, I hit my number and now the counter resets to zero. And again, to your point earlier, and then we wonder why people are quietly quitting. Quite frankly, they're not quietly quitting. A lot of them are Overtly quitting.
Speaker C: So, you know, but why? Because they're not getting what they need. And it's not always the money. Okay, maybe 20, 30 years ago, money might be on top. Now you go and research what people want.
Speaker B: Quality of life is number one.
Speaker A: Yeah. Uh, yeah, yeah.
Speaker C: Honoring priorities, making an impact, connection with people, relationships. Money's there as a priority. Of course we need that. But it's not like we're waking up and saying, I can't wait to, uh, make more money. We're waking up and saying, who can I connect with?
Speaker B: What difference can I make today?
Speaker C: What can I do to honor my
Speaker B: core values and priorities that's going to keep me happy and in check, you know, and if managers haven't shipped the conversations, they're going to wonder why they keep having the old behavior repeated over and over again.
Speaker A: I noticed on the back of your book he had Tom Ziegler write a, uh, little bit about that. And I remember having it several conversations with Tom, and he said something exactly what you just said. There is coaching is to find out people for what they want. And what if it is sales? It's, it's not to get the monthly. Uh, obviously they're going to get paid monthly and they're going to commission. But what does that money do for them in terms of their life? So when you're coaching the salespeople, you. You're finding out their intrinsic motivations, also their extrinsic motivation. What is that money going to do for you once you actually have it? And obviously plant them into the future, but also helping them to just spot that bit of. If they're having challenging times with their clients, bring back in, bring it back to the basics. Bring it back to why you're doing this job. What do you hope to achieve by doing this? Is it to make more friends? Is it to make more influence? Or is it, uh, or whatever it might be, Whatever works for them as a, as a person. And when people are, uh, when things are going really tough, which they can be, as we've spoken about, loss, redundancies and all of that, is to get them back into basics, get them onto that line and going, well, why are you doing what you do? Why do you want to help people? How can you help more people, uh, and inspire them to actually get their organizations working really well. But that's where we coach you to perform better and obviously to find out lots of different things about their, their lifestyle and all of that to help them and inspire them.
Speaker B: And you can do that, you know, when we talk about stress, you know, stress happens again when urgency replaces leadership. And if you're always reacting, when are you ever finding the time to take a step back and have these real conversations? And then building on that to another point you mentioned, what about departmental silos? Uh, most companies I speak to would readily admit they have departmental silos regardless of the size of the organization. Sales has to play nice with marketing, you know, marketing has to play nice with engineering. Sales has to play nice with engineering. You know, sales has to play nice with operations. Operations has to play nice with each other.
Speaker A: Because I was thinking as you were talking, because now we're talking about the whole organization.
Speaker B: Mhm.
Speaker A: Mm. Uh, like we're talking sales here and leadership. What about the coaching culture within the counts team? What about the coaching culture within marketing? What about the coaching culture in, uh, product delivery or whatever else? Because I think that's equally as important to make a 360 movement forward to that organization or any organization.
Speaker B: It seems that what I said and you and I are sharing, you know, certainly the same thoughts is stress and reaction. And strained relationships happen when urgency replaces leadership. So let's play this out.
Speaker A: Now.
Speaker B: I'm in sales, you're in marketing. Typical Mo.
Speaker A: Um.
Speaker B: Oh man, I just got off the phone. Great lead. They actually spoke to me.
Speaker C: Didn't really qualify them, but I got a warm body and I told them that, that, that I'll send them over, you know, and uh, and some specs,
Speaker B: you know, about our products and services
Speaker C: and a price sheet even though they didn't ask for it. And by the way, I'm going to send it to them tomorrow because that's
Speaker A: what I promised them. Oh.
Speaker C: Even if they said they don't need it till next week. So what do I do? Hey, Jason, listen, I got a hot lead right now I need to write up the spreadsheet. I need a quick five page, um,
Speaker B: uh, uh, uh, promo to put this together.
Speaker C: Uh, can you get this to me by the end of the day?
Speaker A: Okay.
Speaker B: And then we wonder why we have departmental silos agenda. I'm not looking to hurt anyone. I'm thinking we have sales, my agenda. What I'm um, not doing is I'm not respecting your agenda. I'm not respecting that you have things on your plate. You have deadlines, you have pressures. That's the cause of departmental silos. We know the what, what's the why? The why is we need to reset
Speaker C: these conversations with every person where we're
Speaker B: having strained relations ships in with different departments and it really builds on something else we were talking about. Jason, not only and for a point of clarity, do I have the salespeople, maybe with the managers, but I love it when, when companies say, well, Keisha, we get marketing in there because it's sales leadership.
Speaker C: Get them in there. Well, Keith, should we get operations in there? Because you're telling me it's sales leadership. Get them in there. Take the word sales out of it. It's leadership. The framework of coaching stays the same.
Speaker B: The conversations and the people change.
Speaker A: Yep. Yep. I, uh, completely and utterly concur with that. And I. It's so often misaligned in that area, and I don't think it's congruent. And I don't. I, um, haven't seen it that often where everyone is in that full coaching.
Speaker C: And, and, and it's so simple.
Speaker B: Reset the relationship. You always have a second chance to make a first impression. I'm changing that quote because if I can come to you now and I could say, hey, you know what, Jason, um, you know, what I want for you is to be able to leverage me as a resource and, uh, help, um, help, you know, help you achieve your goals as well. Quite frankly, I owe you an apology because here I am running to you, um, only thinking about what I need without respecting what's on your plate and your agenda. And for that, um, I owe you an apology. Uh, and I could really use your help. I'd love to hit the reset button on our relationship. Um, I know the last conversation certainly didn't go the way we wanted. And this way we can redesign our relationship in a way where, what it looks like for you, how we can work best together, response time. If I ask something from you so I don't put extra pressure on you, um, how we can continue to maintain a trusting relationship and what behavior might tarnish our trusting relationship. Uh, and these are the questions that facilitate. Nobody is having.
Speaker C: Okay. But if they do.
Speaker B: I've never had a leader, salesperson, anyone from any department come to me and say, keith. It's always Keith.
Speaker C: My gosh.
Speaker B: I just changed my conversation, respected their point of view, shared positive intent, and it works.
Speaker A: What I'm thinking is, um, I remember from your first book, which I stole, thank you very much. And I really like the pre coaching forms which you send in advance, which builds in, um, uh, you've got areas around what you can actually coach them on. And I like the, um, post coaching form with action plans and stuff like that. So what's changed now since you started doing that? 18 years ago to the new principles that you've added in to the new book that you've actually released.
Speaker B: Yeah. So first off.
Speaker C: Ah.
Speaker B: And again, just to simplify things, because managers, especially now, when there's so much fear and uncertainty in our world today, it is a predominant area where people, including leaders, need to be coached on. Nobody knows how to coach fear unless I share with them a process on how to do it.
Speaker A: Yeah.
Speaker B: So, you know, building off what you said, um, you know, we, we, we. The first thing is to overcome that. That relationship we have with fear. Fear is not our adversary. It's our ally. If we tend to listen to it, it's actually showing us, showing up to teach us something. Uh, I'm going to this, uh, because people don't realize there's actually two parts of fear. There's that which we fear, and then there's the feeling of fear.
Speaker A: Yeah. Okay.
Speaker B: The feeling of fear is very real. Manifests in our chest. You know, if you're doing public speaking, you know, maybe you get a pang in the back of your net. Your. Your hands may start getting sweaty. But that which we fear, fear is never real. I don't want to mess up. I don't want to forget my notes. I don't want to disappoint the crowd. What if I say the wrong thing? What if I trip over my own feet? Done that a million times with the size 14.
Speaker C: Uh, you know, and all these what ifs. Well, guess what? When people come to me and say, keith, I need some coaching on this, I say, I'm sorry, I can't help you. And they'll say, well, Keith, I'm sharing with you what I'm afraid of and what might happen. Why can't you coach me on that? And my response is always the same.
Speaker B: How can I coach you on something that never happened?
Speaker A: Yeah. Yeah.
Speaker B: So I can coach you on your assumptions, I can coach you on your mindset, but I can't coach you on,
Speaker C: well, Keith, if this happens. What.
Speaker A: What.
Speaker B: What should I do? Can coach you on that?
Speaker A: Yeah. Yeah. It's all in your imagination.
Speaker B: Yeah. Yeah.
Speaker A: But everything else is.
Speaker B: Everything else is fair game. Yeah.
Speaker A: Uh, you can play with imagination, and you can change the narrative of the imagination.
Speaker B: We're so good at that. We're so good at that, aren't we?
Speaker A: Uh, it's. It's almost like, um, having those conversations. It's m. More of a tactic, really. Is your future self having that conversation with yourself? Into the future, 12 months into the future, you confident, blah, blah, Blah, whatever it might be and just close your eyes and have that conversation. What are you saying? What's the response? Um, and your power of that is it's because you're having a conversation with yourself, funnily enough, but you're using your imagination around that to make an impact. I love that.
Speaker B: Yeah, I, I always share on that same note is, um, you know, if, uh, if, if you ran into yourself in about 20 years, uh, what would you want to see?
Speaker A: Yeah.
Speaker B: You know, and to me that's, that's your legacy. How do you want to be known? And you know to me that, you know, wherever you are in your path, in your journey in life, you know, the choices you made yesterday created your success and your legacy today.
Speaker C: And the good news is this. The choices you make today will create
Speaker B: your success and legacy tomorrow. That's a choice. We start with today.
Speaker A: Yeah, absolutely.
Speaker B: Filter out the noise. Focus on your goals, focus on, keep your direction. Let your routine keep you accountable.
Speaker A: Yeah, I think it is this again, consistency, consistency, consistency. That good consistency with those positive things that you should be doing, but helping your, this is one other thing actually is coaching your team to have a little bit of gratitude of what they've done. Because what we tend to do in life is we're driving forwards all the time. We're hitting numbers, we're hitting KPIs, we're doing this and the other. But where do we actually self appreciate what we have done? Because once we actually do that, things start to change.
Speaker B: Interesting. Uh, really beelines back to your other question about uh, from 18 years ago from my first book and now with a different model and dozens of talk, uh, tracks for uh, critical conversations and questions. Uh, you know it's interesting. I went from having a longer pre call form that I would have managers share with their coaches to just three questions. And the questions are very simple. What are your wins from the last conversation we had? What are your challenges? What do you want to use our time for? What are your expectations? Three questions prior to a one on one scheduled coaching session that the coachee needs to fill out and send now. Why is this so important? Number one, you better enroll your, your team about why they're filling out this form.
Speaker C: Because if you don't and you say, hey, can you fill this out?
Speaker B: Guess what they're thinking.
Speaker C: Wait a second, are you sending this to hr? Is this going into my permanent record? Are you going to hold this against me? I'm not filling this thing out.
Speaker B: And then we wonder why we never get them.
Speaker C: Because we didn't enroll them in the simplest thing. If it's change, we need to enroll.
Speaker B: So now they know why they send the prep form in.
Speaker A: Mhm.
Speaker B: Not only does it help Laser focus on what that person needs in that moment, but here's the thing. When you're dealing with a type personalities or people that are very hard on themselves, you know, managers and salespeople are never like that.
Speaker C: Right. And uh, here we are, six months
Speaker B: pass by and the manager's coaching their coachee. And the coachee, their direct says, you know, I know I've been working hard, the coaching's really helped.
Speaker C: But I just, there are so many
Speaker B: things I didn't even get done because people are really good at seeing what they didn't do, but they're not very good at seeing what they have accomplished. Um, so now guess what, that coaching prep form is now just a path of progress. So now the manager can say, well
Speaker C: wait a second, let's go back to
Speaker B: your first coaching prep form six months ago.
Speaker C: Let's look at that. And let's just take a look at,
Speaker B: you know, several of them as, as we progress in our coaching. And inevitably the coach, he would look
Speaker C: at and say, oh my gosh, I forgot I had that problem. Oh my gosh, I forgot that I turned that person around. Oh my gosh, I forgot I had uh, you know, so much success that second quarter just because I enrolled my team in better coaching, they forget that.
Speaker A: Yeah, yeah.
Speaker B: So it really helps, you know, internalize their wins and spark that sense of motivation again.
Speaker A: Yeah. Because I think that's really important, uh, again that self gratitude, just to recognize the progress that they have made and where they have gone from the beginning of the coaching to where you are now and the progress. Because it's all about progress. If you can recognize you're doing better at certain aspects of your career, uh, yourselves or the internal landscape, whatever it might be that uh, you're working on, I think that's really a cracking job. So at ah, this point, is anything that I haven't asked you that you would like to be asked. Um, wow.
Speaker B: Uh, how much more time do we have, Jason?
Speaker A: I would just keep it quite simple,
Speaker C: I guess.
Speaker B: Uh, some final thoughts that I, I'm noticing more and more I'm sharing with leaders and salespeople is, is that you will get through this. This too shall pass.
Speaker A: Yeah.
Speaker B: Trust yourself. Trust your people. Invest in yourself. By doing what you're doing, you're light years ahead. Because we are working together. Not necessarily because of me, because you have taken the accountability and commitment to invest in yourself and work with a coach. So I would implore every salesperson, every manager, get yourself a coach. I don't care if it's a peer. Um, I don't care if it's someone you could find in another department or someone external. Everyone does better when they have someone in their corner supporting them. Because the fact is, everyone is going through something today.
Speaker A: Absolutely. I, uh, completely and utterly concurrently. And the CEOs of the world, they're the loneliest people out there. They're the ones that need coaching.
Speaker B: Yes, absolutely. As you said, avalanches roll downhill.
Speaker C: And as.
Speaker B: And as I always say, you know, um, you know, beliefs always precede experience. Right. How we think is exactly what we get.
Speaker A: Yeah, whatever. I always like to say, whatever we program into our mind, our brain will find the onset.
Speaker B: Hey, after all, people create the mindset, right? Mindset shapes behavior. Behavior defines culture. Culture determines success. That's why the primary objective of every organization is to make your people more valuable every day.
Speaker A: That's awesome. So I think we should leave it at how can people find out more about you?
Speaker B: Just launched my new website, Tons of free resources. The excerpt you shared, how to master critical conversations, how to, uh, I have several of these, not only in digital format, but in audio format, in Malaysian, in English, and in Spanish. So I am giving that away pop on my website, KeithRosen.com as well as certainly let's connect on LinkedIn, because I'm always offering, uh, you know, my connections and people in my community other leadership tools as well.
Speaker A: Awesome stuff. Well, thank you, Keith. Uh, it's been an absolute pleasure. You've been listening once again and probably the third time, uh, here with, uh, Keith, uh, which is good because we've actually progressed the conversation on since last time. So I'm delighted with this and, um, delighted with the conversations that we always have. And my core principle is to feed it forward and create that ripple effect forward so we all grow and all learn together. And if you can take one thing out of today to propel yourself forward, I think that our job has been done really well. So thanks once again.
Speaker B: My pleasure and wishing you success. And hey, wishing extreme success to everyone out there. And remember, always be coaching.
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