The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Sales/Behind the Boardroom
Behind the Boardroom artwork

Your People Don’t Need More Answers. They Need Better Sales Coaching

Behind the Boardroom · 2026-05-19 · 53 min

0:00--:--

Key moments - from our scoring

Substance score

42 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality7 / 20
Guest Caliber12 / 20
Specificity & Evidence8 / 20
Conversational Craft6 / 20

Keith Rosen, author of 'Coaching Salespeople into Sales Champions' and recognized as a pioneer in sales coaching since 1989, distinguishes between sales training and sales coaching - a critical difference most organizations miss. Chuck (the host of Top Rep, the largest sales coaching platform in home improvement) and Rosen explore how training pours foundational knowledge (scripts, processes, KPIs), while coaching observes, questions, and uncovers blind spots to transform individuals into self-accountable performers. Using the golf coach analogy, Rosen explains that effective coaches operate on the sidelines, observing performance and asking diagnostic questions about skill and mindset. The episode tackles the crisis of modern sales leadership: only 15% engagement, 30-35% attrition, and 85% of salespeople missing quota - issues stemming not from poor hiring but from poor coaching and onboarding culture. Rosen advocates 'coaching up' (asking people how they want to be coached), abandoning assumptions about motivation (not all salespeople are 'coin operated'), and implementing rigorous three-legged hiring-interviewing-onboarding processes like Google's 16-step interview. Sales leaders, new managers, and organizations struggling with turnover will gain practical frameworks for identifying coaching vs. training needs, building psychological safety through care-centered leadership, and transforming their sales cultures through question-driven accountability.

Key takeaways

  • →Sales coaching is fundamentally different from training - it's about observation, asking questions to uncover blind spots, and transforming people's mindsets and behaviors rather than lecturing or preaching information.
  • →Managers should ask their team members how they prefer to be coached and managed rather than assuming everyone wants the same approach, because when people make the rules they own the outcomes.
  • →The cost of replacing an employee is approximately four times their salary, making a rigorous multi-step hiring and onboarding process (like Google's 16-step interview process) a worthwhile investment.
  • →Effective sales coaching requires understanding what's beneath people's stated goals - for example, when salespeople say they want money, dig deeper to uncover what that money actually means to them personally.
  • →Only 15% of employees are engaged in organizations today with 30-35% attrition rates, but managers have the power to change this by creating the culture they want through proper coaching practices.

In this episode

  1. 1Training vs. Coaching: Understanding the Fundamental Difference
  2. 2The Golf Coach Analogy: Observation, Questions, and Skill Development
  3. 3Sales Coaching in a Hybrid World: Leveraging Remote Visibility
  4. 4Talk Tracks Over Scripts: Empowering Salespeople to Make Conversations Their Own
  5. 5Coaching Up: Asking Your Team How They Want to Be Managed
  6. 6Public Speaking and Authentic Communication: It's Not About You
  7. 7Hiring, Interviewing, and Onboarding: The Three-Legged Stool

Mentioned

Keith RosenChuckTop RepBathfitterGoogleMicrosoftNew York RangersNew York KnicksMichigan basketball

Topics in this episode

Sales coaching vs. sales trainingCoaching Salespeople into Sales Champions (book)Hiring and onboarding processesMulti-step interview processes (Google, Microsoft)Talk tracks and scripts in salesEngagement and attrition statisticsHybrid work and remote coachingCRM adoption through coachingPublic speaking and communicationOne-dimensional screen relationships

Questions this episode answers

What is the difference between sales training and sales coaching?

Sales training provides the foundation - teaching processes, skills, KPIs, and talk tracks (like how to hold a golf club). Sales coaching comes after training is poured; it involves observing performance, asking diagnostic questions, uncovering blind spots and mindset issues, and transforming people not just in how they do things but who they are. Coaching builds individual champions while training builds the baseline everyone starts from.

How can managers determine if a sales rep needs training or coaching?

Ask the rep: 'What was your experience the last time you handled this situation?' If they describe a similar past situation, they need coaching (have the foundation). If they say they've never been in that situation before, they need training (lack the foundation).

Why do companies fail at hiring when they bring in dozens of new salespeople?

If a company hired 64 people and they all left, the problem isn't the people - it's the company culture and leadership. The issue typically stems from poor coaching, lack of proper onboarding, or hiring from fear and need rather than choice, causing managers to compromise standards.

What is 'coaching up' and why does it matter?

Coaching up means asking your team how they want to be coached and managed, rather than assuming one approach works for everyone. When salespeople define the rules of engagement, they own it and act on it. Without these conversations, managers coach in a vacuum making assumptions that damage culture and performance.

What should an effective hiring and onboarding process look like?

It's a three-legged stool: hiring, interviewing, and onboarding must all be equally rigorous. Google uses 16 interview steps and Microsoft uses 10-12 because the cost of replacing a bad hire is four times their salary plus lost sales. Companies must invest time upfront in each stage rather than hiring from fear and skipping proper onboarding.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

There are scattered actionable tactics - the email-response interview test, the 'if you did know' coaching question, and the coaching vs. training distinction - but the episode is heavily diluted by mutual admiration, repetition, and generic platitudes about 'care' and 'human connection.' The ratio of novel insight to filler is poor for a 53-minute runtime.

I'm going to send you three emails. One's from an irate customer, one's from a customer that's looking to uh, um, go with one of our competitors. And one's an internal issue dealing with another department. I'm sending you three emails. You have 20 minutes to respond. Go now.
you can't solve everyone's problems. And I'm sure we'll go deeper into that because you can't scale dependency.

Originality

7 / 20

The core coaching-vs-training distinction and the 'if you did know' question are well-worn coaching orthodoxy that will be familiar to any practitioner who has read foundational coaching literature; there is no genuinely contrarian or first-principles argument made. The manipulation-vs-coaching reframe is the sharpest original moment but is underdeveloped.

I'm having a really hard time coming up with the question to drive the person to where I want them to be. That's manipulation. That's doing a Jedi mind trick. That is not creating new possibility.
The dominant sales and leadership strategy today is care.

Guest Caliber

12 / 20

Keith Rosen has genuine longevity (coaching since 1989), credible client logos (Google, Microsoft, NY Rangers/Knicks), multiple published books, and real international practitioner experience across 75 countries - he is a legitimate expert. However, he is primarily a professional coach and author rather than an operator who scaled a business himself, which limits the practitioner depth of his answers.

some organizations that I work with, uh, like for example, like Google, okay. Uh, I think they have about 16 steps in their interview process. Microsoft, about 10 to 12 steps.
After traveling to 75 countries, it was really an accumulation of every chapter being a lesson on coaching and selling, but in a different area of the world.

Specificity & Evidence

8 / 20

The episode offers a handful of concrete data points (15% engagement, 30-35% attrition, 85% quota miss rate, 4x salary replacement cost, Google's 16-step interview process) and one well-structured tactical example (the three-email test), but sources are never cited and the majority of the conversation remains at an abstract, principle level.

right now only 15 level 15% of engagement in organizations. 15%. 30 to 35% attrition.
the cost of replacing someone today is about four times their salary, let alone lost sales.

Conversational Craft

6 / 20

The host spends large portions of airtime praising the guest, narrating his own biography, or validating answers rather than probing deeper; there is zero substantive pushback or challenge to any claim. Questions are frequently vague or leading, and the conversation repeatedly stalls to allow the guest and host to congratulate each other.

That is solid gold.
I absolutely love that I, I've gotten so many different ways of, of interviewing people, but the emails, you know, how do they respond?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Keith Rosenguest71%
  • Chuckhost29%

Most-used words

coaching66sales39managers26training22salespeople22coach18today17back17book17manager17conversation17question17call14keith13questions13last13

Episode notes

In this conversation, Keith Rosen challenges the way most sales leaders think about coaching, training, accountability, hiring, and performance. The hard truth is that your people don’t need more answers from you. They need better coaching that helps them think, own their decisions, build confidence, and grow beyond dependency. Keith shares why coaching is no longer a management technique, but the language of modern leadership, especially in a world shaped by hybrid work, AI, burnout, low engagement, and constant pressure to perform. This episode is for every leader who wants stronger salespeople, healthier teams, better conversations, and results that do not depend on the manager solving every problem.

Full transcript

53 min

Transcribed and scored by The B2B Podcast Index.

Chuck: All right, we are live. This segment is going to be very special to me. This is the, uh, this is the opportunity that I get to introduce everybody. I get this all the time. Like, Chuck, where did you start? Where did you get your start? How did you learn how to coach? Um, and what most people see. See differently with how we do things here at Top Rep and how so many others across the industry are so different. And what I'm going to tell you is that what most people do are doing across the industry, they're training. They're not coaching. Most people don't understand what coaching is. And I get to the opportunity today to show you and introduce you to my coach, who is also the godfather of coaching. This. This individual has been coaching since 1989. Uh, I had been. I, uh, started coaching with him, man. This was back when I was at, uh, at Bathfitter. And, uh, we. We'll talk a little bit about that. But he's wrote numerous books. That's how I got introduced to him was through his book, uh, you know, coaching Salespeople into Sales champions. That book right there, if you have not bought the. That book, it is the bible of sales coaching. You'll know it because, uh, I have literally bought probably close to 100 copies of this. And the reason why I've bought so many copies is because every time I lend that book out, I never get it back. And I'll go through it again, I'll highlight all the, uh, sections that I like, and then I'll lend it out to somebody because everybody knows I give my books away, uh, and I never seem to get it back. And so, uh. And he's actually writing the sequel to that book right now. But I want to introduce Mr. Keith Rosen. How are you, my friend?

Keith Rosen: Hey, it's a pleasure to be present with you, Chuck, man.

Chuck: I. So I honestly, I get so many that will ask, you know, where I got my start. Uh, we are so Top Rep is the. The top sales coaching platform. And inside of home improvement, you know, there are a lot of other coaches out there, and they're much bigger than we are. But, uh, when it comes to home improvement, we are the largest. And, uh, the reason is because we actually know what coaching is. And that all started from being able to work with you so many years ago. Thanks.

Keith Rosen: And it was always deeply my pleasure. So, uh, clearly, uh, the coaching has made a massive difference, Chuck, because we all appreciate the great work that you do.

Chuck: You know, I want to bring this back a little bit because people think that sales Training is coaching. I'm like, no, that's, that's sales training. I mean if you're going to string, uh, a bunch of sentences and give it to somebody, that's training. You're, you're, you're, it's like you're preaching to somebody, you're lecturing. But really, what. And I could sit here and say it all day long, but I want to hear it from you. I want them to hear it from you. What is sales coaching?

Keith Rosen: Yeah, yeah. You know, if you, if you look at sales training, which is the traditional sense, which by the way hasn't changed in, gosh, 50 years, uh, the evolution to me of even sales training is sales coaching. So one thing that I'm even doing, and I know you're certainly an advocate of this, is it's not just about training, uh, salespeople on here's your process, here are your skills, here's your KPI, and here are your questions. It's more about going deeper and transforming them into consultative coaches. Which is what we also want to do with our leaders, is transform them from the directive problem solving legion of managers into a world class elite coach that is empowering their people to be self accountable, motivated so they can achieve the results on their own. Because the one thing I've learned that managers would certainly agree with is you can't solve everyone's problems. And I'm sure we'll go deeper into that because you can't scale dependency.

Chuck: Yeah. And can you give a little bit more depth behind, you know, the coaching that you've done? Uh, you were actually in home improvement a long time ago. You actually, uh, you had a home improvement organization. People look at you and like, oh my gosh, she's in uh, he's in Google. He's in all these big, I mean you, you uh, you coach the, the uh, the Rangers sales, uh, teams. And, and I think if it's in New York, you've coached it, right?

Keith Rosen: Yep, yep, yep. So, so I'll take the credit as long as the team's doing well. Right. Knicks as well. So, uh, I wish I could take credit for Michigan basketball. Go blue. So, uh, but, but in any case, uh, you know, there is one thing I want to dive back to Chuck, and I think it's an important distinction that I want to make sure your audience hears is sales training is a foundation. Sales coaching is what you do after the sales training is poured. So if you look, for example, pick any sport, okay, uh, rugby, soccer, you know, um, baseball, okay. Golf, Everyone is Trained the same way. So if you had a, A, um, class of, let's say 10 students, and you have the teacher in front of you, the teacher is going to train everyone and the teacher is going to tell them what to do. Okay, here's how you hold the club. Here's how you keep your head down. Here's how you, you know, here's your backswing. Here's how you follow through. That's training. Here are the rules of golf. Here's golf etiquette. Okay? These are all the things you need to know.

Chuck: Training.

Keith Rosen: I didn't have a baseline. Now I do. Okay, so, so now I go to my next lesson with my golf coach. Now, does he do the same thing that he did the last lesson? No. This time he knows he poured the foundation on the last, uh, session. So what is he doing now? He's observing. The coaching kicks in. Okay, let's go to the driving range. Show me what you got. Hit some balls. Observing me, observing my style, observing my stance, observing my mindset. And then he'll say, let's go out, uh, to the, to the course and play a few holes. And he'll observe and ask questions. So why did you choose that club to hit that ball? And you know, I noticed you were really frustrated on that last shot, which I'm sure no one who plays golf can feel that. What was your internal dialogue? So he was coaching me on skill and mindset. He's uncovering my gaps. He's observing me. So think of where the greatest, uh, sport coaches are during any game. They're on the sidelines. They're observing the players play. Because players can't self diagnose when they're playing. They're playing to win. They can't self diagnose and play to win at the same time. That's why the coach and the coach's team is on the sidelines, so they can share with them the blind spots that they can't see on their own. That's the coaching. So training, foundation. Coaching builds it and creates them as an individual champion. So even though everyone has poured that same foundation, just like any professional athlete, they all grow into their own style. And the one coaching tool that I can give every manager right now, how can I assess Keith if it's a training or coaching issue? By asking questions. Okay, how about these questions? So how much training have you had on? Or what was your experience the last time you handled this situation? Well, if they say, well, the last time I was in a situation like this, that means they Had a foundation coaching conversation versus well, Chuck, you know what? I'm a month in my new job. I have never been in a situation like this. Training

Chuck: that is, that is gold. And it's, we see this all the time, especially right now where the industry has grown 5x uh, since COVID You know, everybody that was a great sales reps now, now they own their own business and you know, they, so they uh, we've got more new training that we need to do than ever before. Before it just, you know, we, I hate to say this, a lot of people call them retreads or uh, they, they trade companies over and over and over and we just have to train them on a new system. But now we have more new sales reps and new opinions because everybody has one as you're trying to train them than we ever have.

Keith Rosen: Mhm.

Chuck: Now when I was working with you, I started to understand the truth about coaching because it's about questions, it's about, you know, it's the strength of coaching belongs to how the canvas that you're working with. Because there are certain people, I'm sure even that you've worked with, you're like, this person should never even be in this position. You know, they are a great doer, but a coach. But there's others where you're like, oh, I can't, I'm in love with working with this person because they're so good already. I just need to tweak a little bit here and move this over to here. And they already know what they're doing because that's what you kept telling me early on. It's like, Chuck, you already know what you're doing. I just need to pull it out of you.

Keith Rosen: And I think, I think, you know, even to your point, there is so much uncertainty in today's economy and you know, compound that with AI and all the uncertainty and confusion of how companies even need to leverage that. Which is the reason why I wrote the second edition to Coaching Salespeople into Sales Champions. Eighteen years later, the business landscape has changed since then. We're living in a hybrid world. The conversations leaders are having with their people have changed dramatically, especially with the business remote business landscape. So, you know, really touching on what you said. You know, managers and salespeople need to understand that there's been a transformational shift in sales and leadership. The dominant sales and leadership strategy today is care. Okay? And because that is what people want the most today, we have never in the history have, uh, been this disconnected from people than we ever have before. And many of us, if we don't have the luxury of meeting with our customers face to face, are building relationships in this hybrid world on a one dimensional screen. So there, there comes that challenge. But I also believe comes an opportunity. After all, I'm in your studio, you're in my office. We can talk about a lot of different things that we see. We have never had this level of exposure into our customers and people's homes and directs reports homes as we do now. We need to leverage that as an observation. Okay, so before a rep may show up really stressed out and frustrated and you don't know why, all of a sudden you're having a conversation with them and, and you see that they're sitting in their uh, kitchen table. They don't have a home office. Um, dogs and cats are running wild, babies are screaming. Piles of books are on his, uh, table. It looks like he's still wearing the same shirt he has in the last week. Are you going to tell me as a manager you're going to say, okay, let's just go ahead and do this pipeline review. Let's talk about how we can m. Move this deal through quicker. Have a great day. Managers don't know what to do with that information because on one hand they're like, can I even talk about this? Is this an HR thing? No, this is a human connection thing and this is what your people want the most. So as you asked me before, what's a great way to really distinguish between training and coaching? Coaching is that transformation element that shifts people not only from how they do things, but who they are and how they think so they can be who they want to be. And that's why the definition of coaching and selling is the same. The art, language and habit of creating new possibilities in every conversation.

Chuck: Love that. I, you know, the one thing that as I've gotten better at coaching, I've also got better at selling and vice versa. Yeah, the, the other part of it is, um, public speaking. You know, I was just, you know, I was just coaching, ah, an organization. I says, how many of you in the room have been in public speaking? Like three hands go up. I says, all of your hands need to go up. Whether you're talking to two people, husband and wife, or you're talking to 3,000 people, it's the same. Yeah, yeah, they, they made the difference. Because when I'm on stage, I like to scream and yell a lot, but

Keith Rosen: I'm not going to do that in

Chuck: the house, obviously, but it's where you Put your pauses, you know, the emotional connection, you know, um, you know, there's times when you're going to bring your, your tone down. Uh, because today, you know, it really is. We do a lot with tonality when we're talking about selling. You know, it's not about the scripts. Uh, the scripts are there. They're required. But. And, uh, I had someone the other day ask me about scripts, like, how important are scripts? And I. My answer may be a little bit different than yours, but scripts are very, very important because it keeps you on track. You know, there are certain reps. The last thing you want is them to say whatever comes to mind. And then there are others that they're really good at understanding the homeowner, reading the room and saying what needs to be said. So, you know, we have the scripts there. We want even the best reps, we want them to learn the scripts. But how we decide on who's going to use them and who's going to stick to them, it's based on who they are and how they've grown as

Keith Rosen: a sales rep. Yeah, yeah. And I think, I think we're aligned there. I mean, just, we're probably saying the same thing two different ways. The word script, as you know, scares people sometimes. Oh, what are you making me, a robot? I like to use the word talk track. Hey, here's a talk track. This is a professionally baked out talk track that the greatest salespeople use. Let's review it and see what resonates for you and make it your own.

Chuck: That is solid gold.

Keith Rosen: That's coaching right there. You know, and I think that's, that's the part where managers struggle. You know, they bang their head against the wall every day. How do I motivate my people? How do I hold them accountable? How can I get them bought into using CRM? Uh, that could be a two hour call right there, Chuck. Uh, how can we get them more collaborative? When managers hit me with that, I say to them, you're asking the wrong person. Ask your people. They'd be happy to tell you. How do you like to be managed? How do you like to be held accountable? Or how can I be your accountability partner in a way that will feel supportive and not like I'm micromanaging you? And how about the fear of follow up? Well, um, what if you have them also set the rules of the game? Hey, Mr. And Mrs. Salesperson, uh, how do you want me to follow up with you? Uh, in a way that would sound supportive, uh, and not like, again, I'M micromanaging you. So again, when they make the rules, they own it. When they own it, they act on it. It's the same with motivation. It's the same with, you know, we think about how many assumptions we make about what our salespeople want and their goals. Oh, they all want money. No, all salespeople, as you know, are not coin operated. Okay. And as you know, it's typically what's under the money that's most important. So if you had this money, what would that mean? Well, it means peace of mind. It would mean I could send my kids to college. It would mean I could take that vacation. It would mean I could buy that lake house that, you know, my family's been dreaming of forever. Oh, so it's, it's deeper than that. It's more personal, you know, so, you know, that to me is where managers need to understand. Uh, if you've never had a conversation with each person on your team to ask them these questions, how do you like to be managed? How do you like to be coached? Um, what style do you like? What was your experience being coached? What are the things that you'd like to work on? Well, now they're coaching in a vacuum and just making tons of assumptions that everyone wants to be coached and managed the same way.

Chuck: I think you coined the phrase coaching up. That's where you're the first person I've ever heard say that. And ah, people forget that. I want to know how my people want to be coached. Not just managed, but coached. And I says, be careful of the sales rep that says, I don't need attention. That's the person that needs more attention than anybody else on your team. You know, you don't need to worry about me. I'll take care of myself. Yeah, right. Ah, they need the pat on the back.

Keith Rosen: Yeah. And to me, what a great example of using a springboard question. So, uh, when you say take care of yourself, can you say more about that?

Chuck: Yeah.

Keith Rosen: You talk about coaching up and you know, it's interesting when I share that concept. People love it, but, uh, there's fear around it. Wait a second, you want me to tell my manager how they should manage and coach me? Yes. Because guess what? If you don't, they're assuming the way they're doing it is working and they'll be managing you like that the rest of your career and they're managing you that way. And just like, if you're a manager, you're probably managing in your own image or coaching in your own Image, which is, well, I know what I like and I don't know how I like to be communicated and I know how I like to sell and I know how I like to use talk tracks. So I'm assuming this is how you do as well. And now we're building little mini me's and robots. We're not scaling people, we're not tapping into their individuality whatsoever. Yeah, you know, it's like you brought up a great example of public speaking. You know, people and I could share some great stories of failures of public speaking until I learned the lesson. It's not about me. That's the lesson. People like Keith, why do you write a book about public speaking? I'm like, because it would be three pages long, literally. Here's the secret to public speaking. Stop making it about you. How you look, how you are approaching yourself, how people are going to think about you, um, whether or not you're making an impact, how you sound and, and make it about the value you can deliver because you can't focus on both. When you focus on the value you deliver, all that self stress and self imposed pressure goes away because you're showing up as a person who you want to be, which is the person who wants to make an authentic impact. That's, that's the breakthrough of public speaking right there. And you know, it's, and I'm sure you've seen it before, you know, there are stats out there and if you look it up, what's what, what are human beings greatest fears? Public speaking? Death. People literally would rather die than deliver public speaking.

Chuck: Yeah, I can't remember somebody mentioned, uh, that I would rather be the, the one in the coffin than the one given the eulogy. Uh, but so when, when it comes to um, uh, to, to hiring the right people, this is a question that I'm getting so often right now is hiring and onboarding. You know, how do you coach your clients on the proper way of finding the right people, knowing it's the right person? So that, because, uh, just last week we've got a company that came to us and they're like, hey, we, we have hired 64 people. You're gonna, you're gonna crawl under your desk when I say this. Uh, we hired 64 people and they're all gone. I'm like, I don't even know what to say to that other than I'm sorry.

Keith Rosen: But, uh, yeah, yeah, if they hired 64 people and none of them stayed, it ain't about the 64 people. No, it's clearly about the company which you and I, that's our job, right? To call them out on this stuff. Hey, here's the mirror man. What role are you playing in this? So you know, you, you know, you talk about what were the last statistics I saw right now it is so painful and you know, again, probably not a shock to you, uh, there's right now only 15 level 15% of engagement in organizations. 15%. 30 to 35% attrition.

Chuck: Yeah.

Keith Rosen: And in what is it, 20, 25, 85 of salespeople miss quota. Now when I look at this, I don't blame salespeople and I'm not putting blame on the managers because they may know not, they may not have never been trained how to handle this. Yeah, that will put the responsibility on them because is every manager's responsibility to create the culture they want amongst their team. And that's the good news because it's in their power to change it.

Chuck: And that makes a lot of sense when you, when these managers come to us, they, they act as if like I just can't find the right people. It's like, no, you found a lot of the right people. The problem is, is you have a problem with understanding how to coach them.

Keith Rosen: Hey man, you and I, we could probably write a book on this together. You know, it's, it's, it's. How many M leaders do you know that love to overcomplicate things? I mean, right. That's the most redundant question I could ask. Right? I mean my, our job is to make life simple for people, simplify things. You know, most companies, I'm talking about multi billion companies that I coach to startups, they're making the same hiring mistakes. And you see it has to be a perfect blend. It's a three legged stool. It's your hiring, okay? It's your interviewing and it's your onboarding. Three legs. If one of those legs are missing, the stool will fall. In other words, you can have the best hiring process, okay? You can have the best onboarding process. But if you hire the wrong person, you're never going to make the wrong person the right hire, okay? You'll spend the rest of your career trying to do that. Conversely, what if you hire an all star and you just throw them, you know, into the, into the field and they fail because you didn't offer them the right onboarding and training. Well, that goes back to the company again, you had the right person, wrong onboarding failure. So we need to have a perfect blend, which means we need to Put the same time and attention into each step and what I see. And just to give you some baselines, uh, some organizations that I work with, uh, like for example, like Google, okay. Uh, I think they have about 16 steps in their interview process. Microsoft, about 10 to 12 steps. Okay. God bless them. Because there's a reason why they have less turnover.

Chuck: Okay.

Keith Rosen: Than other organizations. Um, one could argue that sounds a little extreme. Well, is it though? Because the cost of replacing someone today is about four times their salary, let alone lost sales. So I rather put the time up front because the biggest challenge today with again with the fear and the uncertainty and not what's going on in this world that we live in. Okay. Managers are in fear and they hire from need rather than choice and they compromise their standards and then wonder why the person doesn't work out. Okay, we need to be objective. First step, how are you bringing people in? We don't need to talk about that. There's a million places you could do. You could use AI, you could use LinkedIn. We don't need to talk about where you're, where you're getting these leads from. The leads come in first thing, pre qualification process over the phone. Many people have that. Okay. Second thing, um, in person meeting, if possible. Okay. Many people have that. Third thing. Maybe meet some stakeholders, uh, or some other managers. Great. Maybe. And maybe not. They'll pair them up with the salesperson, have the salesperson interview them. Maybe. Or maybe not. And I think this is really super valuable is when I would say, okay, Mr. And Mrs. Candidate, I want you to shadow the salesperson for half a day so you can really see what's going on. Okay. Um, but it doesn't stop there. Okay. Because then there's, um. How are you testing, uh, skill? How are you testing will? How are you, how are you assessing their communication styles? Uh, again, you know, I always find it interesting. And managers get suckered by this. You know, they'll, they'll literally be in an interview with someone and, and they'll ask the candidate. So it's the first day on the job. What would you do? Oh, uh, well, before that, before that I would, I would, I would write my business plan out, Chuck. You see, I would have a business plan and then in that business plan, I would, the first thing I would do, I want to interview all the top sellers, salespeople, you know, maybe some of the people that are struggling. So I can really get a good sense of best practices. And then after that, what I'm going to do is I'm going to put my whole sales strategy together for you. Oh, and then after that I'm going to talk to you about how I manage my pipeline and how I accelerate the process of moving deals through completion. And you're thinking, oh my God, I'll pay. Whatever this, whatever this person wants. Anyone could fake strategy. You know what you can fake is the behavioral questions. So you just, and this is something that I go a step further where most people do not do. They may create a scenario like, okay, you're dealing with a customer and they're pushing back on price. How would you respond to that? Okay, you can't fake that. You can't fake communication. The other thing is written style. And this is a big one. I have, um, interviewers, uh, use this as a tool and again, being mindful of AI because they could cheat. This is why we need to watch them. Uh, I say I'm going to send you three emails. One's from an irate customer, one's from a customer that's looking to uh, um, go with one of our competitors. And one's an internal issue dealing with another department. I'm sending you three emails. You have 20 minutes to respond. Go now. I kind of have to watch them now because they could easily just plug that into, you know, chat GPT and get a response. We didn't have to worry about that before. So now we have to kind of make sure either they're in person doing it or we're watching them doing it for 10 or 15 minutes. What are we going to learn? Number one, we're going to learn how they write. Number two, we're going to learn their writing style. Number three, we're going to see how, um, uh, effectively they could even um, structure, uh, and an email. Number four, we're going to see how well they work under pressure. There's a lot of value there that we're missing by stepping over that, that

Chuck: I, I absolutely love that I, I've gotten so many different ways of, of interviewing people, but the emails, you know, how do they respond? Uh, in writing, you know, and you can see a lot about somebody just by the written word.

Keith Rosen: I mean, I, I mean I'm sure you've seen it. Uh, I get emails from brilliant people, you know, CEOs of billion dollar companies. And I would look at this email and I would think to myself, when my kids were five, they could have written a better email than this.

Chuck: Are there any assessments, anything else that you, uh, you like to put somebody through to say, uh, you know, I think that they're good enough to go to the next round.

Keith Rosen: And when you talk about that, are we talking, what, from salespeople to manager

Chuck: or, um, just hiring salespeople in general?

Keith Rosen: And I'm, uh, sorry, ask me that question.

Chuck: Are there any other, um, like, assessments or, um, questionnaires, things that you like to ask them? Make sure that, yeah, I think they're good enough to go to the next round?

Keith Rosen: Yeah. Yeah. You know, as you say that to me, again, just like selling and just like coaching, you know, it all comes down to leading with questions rather than leading with answers. So, uh, some of the questions that are popping in my head real quick are, uh, probably, you know, actually exactly where you're coming from. Are they even going to make the next level? Is. So tell me about your last position. Everyone asks that. Great. Tell me about one of the challenges you ran into. Wow, I never heard that one before. Yeah, um, tell me about your greatest weakness. Oh, I'm a perfectionist. I work too hard. Okay, um, those are not the questions you want to ask. The question is, so help me understand about your last position. What was a relationship you had with your peers? What was the relationship like you had with your. With your manager? Oh, great. Is it okay if I give them a call? If they say no, that's a red flag. If they say any, um, reference of no or, uh, you know, composite of no, maybe. I don't know if they're available. You know, they're very busy. I don't know if they're there anymore. You know, any of those excuses. That's a red flag for me right there. Even if the manager doesn't work there anymore, they still have their mobile number. Okay. And I'll even take it to. Let's, you know, people say, keith, what if I'm hiring people right out of school or never went to college before, Everything we talked about still applies. Okay, well, maybe you can't ask them. We'll talk to me about your, you know, your last position. But I don't know if I was 20 or 19 or 21 looking for my first job. I got a history of jobs that I had. Whether it was running out, snow blowing, whether it was working at a. At. At a store, whether it was delivering newspapers. You know, that still says a lot of stuff about who you were. Do you have initiative? Do you have tenacity? Do you have gut? Are, uh, you, you know, uh, you know, are. Do you have an entrepreneur, Entrepreneurial spirit? You know, if you're telling me you sat there and gamed all the, all time. I'm not gonna, not really exciting me about that. So to me, even, you know, can I speak to one of your teachers? I mean, I know that sounds bizarre, but so is our world right now. You know, nothing is off the table.

Chuck: Yes.

Keith Rosen: Yeah.

Chuck: Ah, when, when I'm hiring and, and maybe you can coach me on this. But uh, when I'm hiring, there's two things that are huge red flags for me. Can I push your buttons and make you defensive? I don't want anything to do with whether you're a manager or a sales rep. I don't need anybody that gets defensive. I, I, we are looking for emotional intelligence. But the other thing that we're looking for, and this one flips people out, is people pleasers. I can't stand them. I don't think there's a, there's not a place. I don't care if it's for the janitor job. I don't want a people pleaser.

Keith Rosen: Yeah, it's interesting. I actually just got uh, off doing a, uh, workshop on time management and about setting boundaries. And a lot of salespeople are not very good at setting boundaries, even managers. Why? Because, because most managers and salespeople care. That's why they're in sales. They have some degree of care. Sure, they want to be successful, but they also care about their customers. And, and this actually can get in their way because, and it's a paradox. Um, when I ask salespeople what are their biggest challenges, sometimes they'll often say, well, some, the demands of my clients. And I'll say, well, give me an example. Oh my gosh. Well, I was having this, you know, great conversation with a prospect and at the end of the call we of course nailed next steps. And, and the next step was I was going to send some information out. So you know, I said listen, I'll get this out to you tomorrow. And the prospect said, great, fine. So the rep ended the call and is like, okay, this is great, I gotta get, oh no, wait a second. I promised that to 10 other people. I'm stressed out. I have so much on my plate. What do I prioritize? Prioritize who created that problem? It's not the customer. It's, it's the rap. It's you. That's the good news. We put self imposed pressure on us and we have an inner narrative that says if I don't serve the customer immediately, I'm gonna lose them or I'm gonna lose them to a competitor. That is a lie. Okay. Your customers will appreciate you setting boundaries and saying no, because the greatest leaders I know are comfortable with that. And I'm not saying running around saying, no, I can't do that. I'm saying use your language and use your questioning. For example, if I'm having a conversation with a prospect and it's the end of the meeting and it went really, really well, did the discovery sounds like it's a good fit. Thinking about the next step. Okay. And the next step might be whether it's going right to contract or sharing, you know, you know, a three page summary, uh, or executive summary. And as a matter, as a salesperson, I'm selling every day too. I could send it out and call them up or email them and wonder why they're never following up. Then they fall into the abyss, and we never know why. Well, here's how you prevent that. You're on the phone or you're having a video, um, conference with them. It's the end of the call. Mr. And Mrs. Customer, how you feeling about our conversation? Feel great. What's standing out most for you? Well, I really liked your, um, I liked your, uh, process of implementation, I liked your deployment, and I really like the way you build your product.

Chuck: Great.

Keith Rosen: Um, what, if any, concerns do you have at this point that could get in the way of us working for together? No, Nothing now. Which, by the way, is a billion dollar question, because every great salespeople needs to smoke out the objection before they hear it, not at the end of their process. So you're asking these questions, and then finally you say, okay, great, Mr. Mrs. Prospect, um, I know you requested some information. I'm happy to send it to you. Uh, when do you need it by? Well, and here's Monday. The rep would normally be thinking they need it tomorrow. And then all of a sudden the customer says, well, listen, um, it's Monday. Uh, you know what? I'm actually traveling this week. If you get it to me by next Monday, that'll be fine. You just gave yourself a week of space. The customer didn't put the pressure on you. We put it on ourselves.

Chuck: Right.

Keith Rosen: And then, of course, what do we do next? Great. So if I get this to you by next Monday, let's go ahead and schedule our next call. And they might say, well, if I get it Monday, I need to speak to, um, some other people. I need to speak some other decision makers. Uh, when, when might that meeting happen? Oh, it'll probably happen if I get back on Monday, probably Wednesday, so. Oh, great. Can we shoot For Friday for a meeting. Don't let them off the hook. It's a give get. Always has to be. Otherwise if we're not holding them accountable, how are we ever going to sell? So again, we need to be mindful of putting the pressure. We're doing that, not the customers. So remember, a great service is not defined by the salesperson. It's defined by the customer.

Chuck: Keith, let me ask you. So a lot of sales leaders are going to be watching this, uh, or are watching this. And what is. We're in a, in a, in an industry that I like to call this results based leadership, which, uh, I was, I was talking with John Maxwell once, this is a while back, and I says, I don't know if you'd agree with me, but there's a difference between leadership and results based leadership. He's got this big smile on his face. He says, you're in home improvement. I said, yes. He says, you need results today, not next week. And I said yes. He says, I love your train of thought, but I'd like to get your thought process on this. When you have leaders that they can't, they can't look at, well, we're supposed to do, uh, $100,000 or we're supposed to do a million dollars this month. It has to be, we need to do $100,000 today. You know, it's got to be today because once today's gone, it's gone. It's like the, uh, the CSR is when they book a call for tomorrow. It's like that call could have been today and I need those calls today. So what would your train of thought be when you're training a sales leader, uh, in this industry, what are some of the most impactful things that you can teach?

Keith Rosen: Well, for sales leaders? And one of the things that I'm really excited about is the release of my second book. The one that you had, that you kept giving away. You're going to have to get the second one in your hands because. Coaching Salespeople into Sales Champions, 2nd Edition. Eighteen years later, to your point, the landscape of business has certainly changed. So what are the things that I see now that might have changed from 18 years ago? Well, there's certainly the consistency that we need to keep our people first. I've evolved my sales, my coaching model. I've, um, built out, um, uh, about 30 or 40 critical conversations managers need to master that they never had to have before. And even so, building all this around the whole concept of technology and AI and how is this Impacting organizations and how is this impacting sales teams? Most companies still are struggling with how to leverage it. And if they are leveraging it, they're often not leveraging it the right way. So it's not just from a manager's issue. You know, this, this obviously goes down and bleeds down to the salespeople as well. So one thing that I've written about is, number one, what's a new conversation that managers need to do? Training and coaching, how to leverage AI, how to use it the right way, how to marry technology with humanity. That's the billion dollar question right there. That's what managers need to learn and then coach and teach to that. Okay, so it's about leveraging that. It's also about leveraging the personal conversations that managers never had before. Like, hey, um, how are you handling challenges that show up at home? How are you handling challenges that show up at work? What are some of the challenges that overlap? How good are you at turning off at the end of the day to be present? How effectively are you managing your calendar? Hey, how about we share our calendars so that, uh, you know, you can look at mine and I can look at yours. How well are you practicing self care and taking care of yourself? How do you set boundaries with your family between work and play? No manager has ever had this conversation because it's never been in front of anyone's line of vision. But that's a conversation around care. And that's the deeper thing that managers need to get to, to really connect and be able to shift. All those statistics I shared so their turnover drops, so their engagement increases, so the percentage of people hitting quota increases to 80 to 90, if not 100%. And the great news about all this, it falls in the manager's lap. It's all in the leader's power. So as you first started our conversation, most managers don't know how to coach. Or worse, they think they know how to coach and they think they're coaching and they're not. They're actually directing and manipulating. So I always very quickly can tell whether a manager is manipulating someone or coaching someone when they come to me and say, you know, Keith, I'm having a really hard time coming up with the question to drive the person to where I want them to be. That's manipulation. That's doing a Jedi mind trick. That is not creating new possibility. That is driving your agenda. That is not coaching. At that point point, you might as well tell them what to do. Because I could tell you right now, while Your people come to you and you think you're doing them a favor by solving their problems. Because after all, many managers, what they were raised from being a top salesperson and now they're a manager. Uh, coach training, leadership training. Oh, we don't provide that here, but you are a great salesperson. All right, so let's play this one out. One of their directs comes to them, hey, boss, I have a question on this one. Deal. New manager says, okay, wow, I've been in that situation a million times in one nanosecond. They process that and say, well, this is what I did when I was in that situation. So here's what you should do. That's not coaching. That's being directive. That's building mini me's. Okay. That's not coaching the individual. Uh, so that's one of the challenges that I see. That's directing. You know, coaching would be, hey, listen, I really value your opinion. You're a lot closer to this than I am and I really trust you and I trust your judgment. What's your opinion on this? And that 10 second question. Managers can use literally all day long. And if managers want to get your time back and your life back and stop running around solving everyone's problems and doing everyone's job and let them do their job. Your job every day as a leader is to make your people more valuable every day, not to drive results. The byproduct of making your people more valuable are the results. So, you know, managers really need to understand that coaching is also a fundamental shift in how they think and how they think about business and the clarity that they need and the confidence that they need, uh, and the model that they need to realize. Coaching is not an event. It's not something you do to someone. It's who you are, it's how you show up, and it's how you communicate in a deeper way that connects people, that fosters engagement, which creates a thriving culture. You know, that's the model right there. Uh, of course there's deeper parts, but if leaders can process that, if companies process it, that's how you build a sustainable, thriving coaching culture. Which is why most companies out there do not have one.

Chuck: I hope everybody's watching you right now because the way that you and I are having this conversation is the same way that anybody would have a conversation with their client. You know, when we're coaching, and you said this early on, is that coaching is selling. Coaching is no different than how you walk through a, uh, sales appointment, is asking the right questions. And then sitting back listening to the answers so that you know how to take the conversation in one way or the other. So I, I really hope that it's not just everybody sitting in awe of everything that you're saying. But how can you sound like this in front of Mr. And Mrs. Smith?

Keith Rosen: Yeah, yeah. You know, and, and you bring up a great point because it really marries back to like public speaking. And what we talked about is that the secret to public speaking is stop making it about you and make it about the value you give. All of a sudden you're not focused on you. Okay, well let's take that now to more of a micro level. A conversation with a customer or a manager having a conversation, um, with ah, with one of their directs. One of the hardest things for leaders and salespeople to do is detach from the outcome. Outcome. And they hear that like, wait a second, Keith, are you telling me to forget about my goals? No, I'm not telling you forget about your goals. Your goals are set. Focusing on them doesn't make them manifest anymore. Okay, so when you're having a conversation, remember, as I say to every leader and salesperson, what's the definition of sales leadership and coaching? The art of creating new possibility. When you're in a sales call and you're pushing your own agenda, that's not you creating a possibility. That's why true consultative selling from a coaching perspective and managers coaching people is the same because the greatest salespeople are creating new possibilities and conversations, maybe ones that they didn't even see. Same with leaders. And when you do that, that's when you start enjoying your job again. That's when it's not monotonous. That's when you're creating real value. That's when, as you can see, that gets me super excited.

Chuck: You know, you never let me get away with saying, you know, I don't know, you'd, uh, ask me a question. I don't know. Your follow up question was always the same and it was always, well, but if you did know, what would the answer be? Yeah, I hope everyone heard that.

Keith Rosen: One of the best coaching questions out there.

Chuck: Yes, I, I ask it of my, my coaching clients. I even when, um, when I'm asking a client or a customer when I'm selling windows or if I'm selling a roof and I ask them a question and I go, I really don't know. But, but if you did know, what do you think the answer would be? And they always bring the answer. They know it, they just don't want to bring it to you.

Keith Rosen: Yeah, yeah, yeah. Uh, or the typical reaction is people just say, I don't know. Give me the answer.

Chuck: Yeah.

Keith Rosen: You know, and. And if people didn't capture that, and I know it might sound silly, it's. Well, if you did know, what would it look like? That sounds weird. Ask the question. But you have to say it with a straight face is what I tell people. Always get an answer. You'll always get an answer.

Chuck: So, uh, you've. You've written multiple books. I know time management outside of what I would call the Sales Bible, uh, or Sales Coaching Bible, which is coaching salespeople into sales champions. If you're watching this right now, the thousands of you that are watching this right now go out, get the book. Uh, you're gonna thank me, and then next month, when, when the second one comes out, get that one too. But you're gonna do the exact same thing that I did. Make sure that you have a highlighter ready. By the time you get to chapter two, you're gonna realize that you're reading something that, that you know, you should go back and read chapter one because you're just reading the words. You're just trying to figure out if this book is going to resonate with you. I'm going to. I'm going to blow right past all that and say, you have not read a book in coaching quite like this because there's a lot of stories in there. Uh, even as, you know, like you say, it's 18 years ago, I mean, the stuff is still relevant today. When people ask what is the greatest sales book, it always comes back with two answers. It's either the Bible or. Or it's how to win friends and influence people. Right. Well, for me, when it comes to coaching, when it comes to understanding how to coach, you will not read. And I've written books myself, but you will not read a better book than coaching salespeople into Sales Champion. I, uh. And like I said, I've bought it so many times because it's never been given back to me. But, uh. But you've written some other books. What other books have you written?

Keith Rosen: Well, let's see. We have Sales Leadership, which was my last book a few years ago. And, uh, that was an interesting take for me. After traveling to 75 countries, it was really an accumulation of every chapter being a lesson on coaching and selling, but in a different area of the world. So it could be from India to Africa to Australia to South America to Germany to Italy to Spain, and all the Lessons that I've learned from traveling to different cultures about themselves, which is to me is such a passion of travel and connection and culture. It's, it's such a passion of mine because that's how we really connect with people. And you know, it, it all comes down to the same thing. We're all running into the same challenges because we're just dealing with human beings and we're all the same. Wherever we go, we all, we all families we love, we all want to achieve a level of success, we all want to have a level of happiness and health. These are universal things, you know, and that's why I always say coaching is truly a universal language. You know, it is the language of leadership. So when managers really learn the language of coaching, that's how you transform a team. That's how you transform an organization. You know, that's how you transform a culture. And you know, I always say people create the mindset. Mindset shapes behavior. Behavior defines culture and culture determines success. Which is why the primary objective of every leader and organization is to make your, uh, people more valuable every day. So the question before the pandemic was, you know, how every morning a manager would wake up, how am I going to hit my business objectives today? That's not the right question we asked today.

Chuck: Mhm.

Keith Rosen: The question every leader needs to ask themselves when they wake up is, how can I make my people more valuable today than they were yesterday? Because that's your primary objective.

Chuck: Love it. Well, Keith, thank you so much for jumping on. Thanks for giving your time. I know it's very valuable. And uh, how can people reach out to you? How can they, they learn more about you and your.

Keith Rosen: Oh yeah, jump on my website, Keith Rosen dot com. I have actually tons of books and resources there that I'm giving away right now. There are some great, uh, downloads for my new book that you can get in audio and actually translated in English, Spanish and Mandarin. So if any of you speak one of those three languages, you're going to be in good shape. Shape. I have the print version and I have the audio version and I'm giving them away for free. So if you want to, to get those, just go to keithrosen.com and go ahead and download them. Enjoy them there.

Chuck: Awesome. Thank you so much, Keith. And uh, again, I can't wait to talk to you next time.

Keith Rosen: Deeply, uh, my pleasure. Wishing you extreme success, Chuck. Thanks for everything as always.

Chuck: All right, uh, folks, that, I hope that, that you got as much out of that as I did. Keith, uh, is uh, is a wealth of information. He, he really is the godfather of coaching, the way that coaching should be done. Most people are trainers, not so much coaches. And if you are one of those people, look up Keith. Get the book. Get coached by Keith. Uh, and. And you're not going to be. You're not going to be sorry. I promise you that. But, uh, until next time, stay a top rap it.

More from Behind the Boardroom

All episodes →
  • The Conversation of Care. The Leadership Conversation Managers Need to Connect with Their Team38 / 100
  • Training or Coaching. What Is The Difference?53 / 100
  • Sales Coaching and Personal Development Session with Keith Keith Rosen and Microsoft66 / 100
  • Transforming Sales through Coaching and Care Microsoft Live Event53 / 100
  • The Toxic Trap Impacting Managers that Sabotages Your Coaching - Coaching In Your Own Image
Explore the best B2B Sales podcasts →
All Behind the Boardroom episodes →