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How to Improve Sales Productivity Through Coaching, with Keith Rosen [Episode 436]

Keith Rosen, CEO, executive sales coach, transformational expert, advisor to top sales leaders, and author of the number one sales coaching book, Coaching Salespeople into Sales Champions: A Tactical Playbook for Managers and Executives, and his most recent book, Own Your Day: How Sales Leaders Master TIme Management, Minimize Distractions, and Create Their Ideal Lives, joins me on this episod to discuss the fundamentals of sales productivity that reps can harness right now.

Key Takeaways

  • Keith has created his ideal life. He has coached sales leaders for the last 30 years around the globe in over 60 countries, for all aspects of the sales process.
  • Keith started sales in college, door-to-door, selling mortgages, remodeling, and home security systems. Keith focused on making salespeople into great coaches, and started his business to address that objective.
  • Keith compares trusted advisors to coaches. In selling, the same questions apply as in coaching.
  • Keith discusses best practices in three areas: questions we ask; critical questions we fail to ask; and changing what we do and how we think. Then he offers a simple way to change our behaviors. One key desired behavior is to ask questions.
  • If you have to close someone, you’re not doing your job.
  • Coaching wasn’t always common. When Keith started coaching, people wanted to know the team. Keith says the coaching gap today is with sales managers.
  • Keith insists that technology and data do not replace individual coaching. Coaching isn’t to gather data, but to help improve behaviors. Data doesn’t reveal why a seller excels. Why is observation necessary?
  • Hiding behind technology makes it easier to avoid personal connections. LinkedIn is for connecting, and building relationships, not for spamming.
  • Consumer retail isn’t dependent on relationships, but  complex B2B certainly is. In B2B, you want to like the person from whom you are buying.
  • A to-do list is ineffective, and usually you put things off, because there is no accountability. Anything that cycles consistently, needs to go on a calendar, not a list. Only one-time items belong on a to-do list.

Episode Transcript

Andy Paul  0:35  

Hello and welcome to the Sales Enablement Podcast. Joining me on the show today is Keith Rosen, CEO, executive sales coach, transformational expert advisor to top sales leaders, and more importantly author of number one sales coaching book Coaching Salespeople Into Sales Champions, tactical playbook for managers and executives. Wow, sounds like a great thing. Keith, welcome to the Sales Enablement Podcast. 


Keith Rosen  1:30  

Thank you very much for having me here today, Andy.


Andy Paul  1:55  

Introduce yourself. How did you get your start in sales for instance?


Keith Rosen  2:02  

Sure. So I’ve been working with sales leaders, sales managers, salespeople, probably for the last 30 years, 10s of thousands of them around the globe, five continents, over 60 countries, working on predominantly sales, cold calling prospecting, time management, working with managers on helping them develop into elite transformational coaches. And have been doing that for the last 30 years. So I’ve had the pleasure of traveling the world and making an impact on so many companies and so many people one at a time. 


Andy Paul  2:52  

So, I mean, you must have been a very young man when you started the company. What pretty much a couple years out of college?


Keith Rosen  2:57  



Andy Paul  2:58  

So what did you do when you were still pretty much wet behind the ears, yourself sales wise, so that you could teach people about sales.


Keith Rosen  3:06  

I started working right out of college actually during college I got a job canvassing door to door I think that’s when it was actually fairly safe and still legal to be able to do that and go door to door and was literally canvassing knocking on doors booking appointments, and I was working for this one company and then after that my second year in college, I started actually doing the sales for them. 


Andy Paul  3:30  

And what product are we selling?


Keith Rosen  3:32  

That type of industry was going back years ago. It was mortgages, we were doing mortgages, we were doing residential, and consumer commercial remodeling, home security systems, things like that. So I got a very strong education and in that environment, pretty young in my career.


Andy Paul  3:56  

Yeah, I was gonna say if you felt powerful enough to start your business after a couple years after thinking back to myself two years out of school, print, I’d been in sales two years, but I wouldn’t have thought I could go teach anybody anything at that point.


Keith Rosen  4:08  

I think what happened after having worked with these companies and then starting another company and realizing that, there has to be a different way to sell, the old sales has not technically changed in I don’t know, over 100 years. Even the books that you read today, they’re just repackage strategies from years and years ago, and you’re talking to a huge advocate of Zig Ziglar, who’s not only a mentor, but I am, I feel blessed to say he was a personal friend as well, having spent one on one quality time with him and even the books that he’s written. I think he’s one of the godfathers of sales. Him and Tom Hopkins and Augmon Dino, they’re still the new books still profess the same ideology and methodologies that they created. Dozens and dozens of years ago and the thing that I have focused on which you heard it from me first and it’s not only just about making managers, great coaches, but the evolution of sales is making salespeople great coaches. And that’s what you’re going to start hearing more and more about is as people steal my idea No, I’m just kidding. I’m writing about the greatest sales people. You know, you can talk about consultative selling, but the next evolution of that is really becoming what I call the seller coach, which is how you can take the coaching technology and apply it to a sales process. And when I’m working with salespeople or sales managers, when I’m delivering a program, the methodology and the content is very, very similar that grants the conversations change. The strategy may change, but the overall communication method is virtually identical.


Andy Paul  6:03  

Well, it sounds like when you talk about turning sellers into great coaches to some degree, it sounds pretty parallel to the whole sort of trusted adviser type approach.


Keith Rosen  6:14  

It does. And if you think about what an advisor does, advisors are just going to sit there and tell you what to do. And advisors going to first understand where you’re coming from, what your goals are, where your current level of thinking is, what assumptions you’re making, where you want to be, what’s getting away of you getting there, they’re going to spend the time to ask all these questions, which is what a really good coach does. And if you’re in a sales role, you need to do the same thing. It amazes me every time I work with an organization, it doesn’t matter if it’s one of the largest organizations out there or a small organization and I go through the company sales process. It blows my mind how when I get to the initial qualification stage, How many questions are actually missing? That the salespeople need to be asking, but they’re not, which is exactly what’s getting in the way of the sale.


Andy Paul  7:11  

So several questions that follow from that is, you know, back to what you’re talking about before is, there’s nothing new under the sun with sales. So I guess one question is, can there be anything new? I mean, given that as you talk about sort of a series of set questions that we think everybody should be asking, I mean, are there really new questions that should be asked or it’s just a matter of getting people to be consistent, disciplined, and make a routine of asking the questions we know are effective.


Keith Rosen  7:41  

I think, first off, it’s to your last point, Andy reinforcing the best practices. What are the questions that inevitably every great salesperson needs to ask every prospect in order to disqualify them, then it’s all what questions are we asking that we need to ask? Every time I work with a client? There are always questions I find they’re not asking which are critical to their sales process. But I think the third part is less tactical and more what you think of me, when I work with managers or salespeople, I take a very holistic approach to professional development and evolution. It’s, you need to change what you’re doing. But you also need to change how you think. So if I’m only focusing on what you need to do, and I’m not focusing on how you need to think or who you need to be, that I’m actually only developing half the champion that that person can be, or if I take a holistic approach and help that person, evolve their thinking, the byproduct of that is it changes behavior, so you know that that same beliefs proceed experience is so true, you’re thinking, the byproduct is a change in behavior. So for example, if I’m coaching a salesperson or even a manager on the concept of being curious now, if you notice, hey, listen, you need to be really curious. As a matter of fact, you need to be insatiably curious when you’re speaking to your direct reports or your peers or a customer or prospect. And if they come from a place of oh gee, if I’m being insatiably curious, well, what am I going to do more of? I’m going to ask more questions.So you change your belief, the output of that is it’s a change in behavior. Now, if we take that to another level, you mentioned before about what’s new, is there a new process or a way of doing or even a way of thinking? Well, when I’m working with managers, especially managers that have a lot of experience in citizen sales, it is as if I’m working with them on the skills of becoming a great coach. Inevitably a manager would jump in and keep a lot of these practices applied to sales, I would say exactly, they really do. And there’s that one part that managers get stuck on. When I say, as a manager, when you’re coaching someone, you need to be fully detached from the outcome. In other words, you can go into a conversation with your own agenda when you’re coaching someone. Because if you’re doing that, then you’re just pushing your own agenda. And you’re not coaching them. Because coaching is all about the art of creating possibilities, not the science of driving your own agenda, right? And I take that to sales now. And it kind of freaks salespeople out a little bit when I tell them hey, guys, listen, when you’re out there and you’re selling or prospecting, the goal is not to sell. And I say, Keith, get out. Leave now, because you don’t know what you’re talking about. And I would say wait, wait, let me finish my thought. The goal is not to sell because that’s not your initial goal. You see, the byproduct of you being a coach is the sale. So for example, if a salesperson is focused on that on that prospect or customer, and they’re truly focused on wanting to deliver value, and they’re focused on seeking to understand that other person’s point of view. And because of those things, they’re asking more and they’re asking better questions. The byproduct of that is that they’re demonstrating value. The byproduct of that is that they’re modeling the type of person the client or the prospect wants to do business with and the byproduct of that is the sale. You don’t have to push for it. And a lot of times before I remember years back managers would say, okay, keys when I’m coaching it’s about asking open ended questions and having the person self assess so they can self actualize and come up with their own answers, which is true. And then they would say but when you’re selling it’s okay to ask the leading questions to get to the sale. Right? Well, not anymore. That whole concept of closing people. It’s sort of an archaic concept in sales these days. 


Andy Paul  12:19  

I’d argue that it always was.


Keith Rosen  12:20  

Yeah, if you have to close someone, you’re not doing your job.


Andy Paul  12:24  

Right. Well, so I mean, in the business of business space, this point a lot is that if you are selling anything with historic complexity to it, you’re never present when the decision was made.


Keith Rosen  12:38  

What is the stats now? 


Andy Paul  12:45  

I think of the challenger customer, but then talking to Brent Adamson who wrote that on the or co authored that book on the show a couple months ago, and he thinks up to 6.8 or 7.2.


Keith Rosen  12:55  

So you’re talking about now seven people are involved in making a business decision. Having some scale is no longer about one person making a decision which changes the thinking of Okay, well, here’s our sales process. Well wait a second, as a business, you can’t just look at your sales process. You have to make sure you’re aligning your sales process with the buyers buying process.


Andy Paul  13:15  

Oh, absolutely. And that’s changed substantially, right?


Keith Rosen  13:19  



Andy Paul  13:20  

So, I want to dive into the coaching thing a little bit from the management standpoint is again, as I said, your first impression, and you wrote this book nine years ago, and over the last year, the book about coaching salespeople into sales champions and over the last year, this whole issue of coaching versus managing them there are multiple books published about, becoming a better sales coach become better sales manager. So why do you think we got all this attention paid to serve in the last year? And they really start talking about some of the things you would talk about, you know, eight, nine years ago not for sure, smart foresight and so on. But why do you think it suddenly seemed to be more critical?


Keith Rosen  13:57  

I equate that to when the mobile phone came out. Everyone looked at the mobile phone and said, Why would I need a mobile phone? Why would I need a phone? Keep in mind back in the day, right? Why would I need a phone installed in my car? Why can’t I just use a payphone? Why would I ever need that? And that’s what people said years ago. They said that about a pager. If anyone listening to this can even remember what a pager is a device that just sends the alphanumeric number that you then have to go find a phone and call that person back. Why would I ever need that? And now the mobile phone is a part of our daily decor. It’s part of when we get dressed, we grab our phone and go I mean, just look at the younger generation. So I think a lot of this has to be a generational gap as well. You look now at what’s needed, any new technology may be challenged a little bit because people are resistant to change. So, when I first wrote the book, coaching came out, even 30 years ago, when I told people I was a coach, they would say you’re a what, for what team? I’d say, I’m an executive coach, I’m a business coach. I’m a sales coach. And I would say, Wait, you’re, you coach, people on sales and business and leadership. That’s the dumbest thing I’ve ever heard of in my life. And this is what I heard 30 years ago. Of course, today I’m laughing. But I think that that same experience happened when I wrote my book on coaching salespeople, sales champions, which is an outgrowth of what I saw as a main gap out there in the marketplace where I did a lot of sales training.


Andy Paul  19:25  

But there are countervailing pressures that exist, which is that as more technology comes into the sales space, we see already that some managers feel overwhelmed by sort of the metrics, you know, the data is keeping track of the process and the activity levels and I was at a conference just less than a year ago, where fairly senior sales leaders were talking about, you know, during the day of doing one on ones, it’s not that that’s all done. I was like that seriously? I mean, we’re getting pushback on that, because they think that they can just look at their reports, and that’s all they need to know.


Keith Rosen  20:10  

Yeah, that is one word for that. It’s called sad.


Andy Paul  20:17  

It’s not sustainable, 


Keith Rosen  20:18  

So, the managers today because of this, they’re being inundated with technology. And because of the technology, we have so much more visibility into our sales people in their activity. And I probably get called at least once a week from some type of new CRM coaching application where they want me to look at our portfolio. There’s a gap and most of them because they are just glorified CRM systems.My point of bringing this up is: With all the data that managers have at their fingertips, the costly assumption as well, to your point, as you heard at this conference, well, I don’t need to go out and observe. I don’t need to, you know, spend one on one time coaching my people, I have all this insight. I have all this transparency, I could just pull up their dashboard and see everything they’re doing well, there’s a problem. You see managers actually. And it might sound counterintuitive, counterintuitive, but even more so. They need to be more people managers than data managers. So if I really want to know what my people are doing, I can’t look at a spreadsheet, I need to observe them, I need to do desk side observation. I need to observe their emails in their written communication, I need to do just death side observation as well as join sales calls, listening on calls over the phone, observe them during a meeting, whether it’s a team meeting or working with a client or a prospect, because and I’ll say this as pointedly as I can, if you global you as a manager. are not observing your people in some way, shape or form, you have no clue what they’re doing. Because again, data tells you what observation tells you how they do it, and why they’re doing it that way. They just do it differently. And that’s what makes them champions.


Andy Paul  24:26  

Well, there’s an extension of what you’re talking about, which is that we have the sort of same conundrum taking place in the sales world itself, though, not just between managers and individuals. But moving beyond the metrics in the process and making sales more personal. Cosimo went through this trend and many respects since we can automate so much of our outreach that some companies are relying on that in terms of their lead gen is that they haven’t mastered how to sell to another person.


Keith Rosen  25:00  

We have a very easy way to get out of doing that when we can hide behind technology. And I am not pointing at any generation or generational gap. But it’s not a secret that the younger generations are a lot more tuned into leveraging social media for marketing and prospecting than the older generations. And actually, I think it’s getting in the way of to your point that interpersonal communication, you know, I’m always very hesitant when I’m on LinkedIn to accept someone’s invitation because I’ve been down the road so many times I even coach around this is that if you’re looking to use LinkedIn, which I still believe is an amazing tool as a marketing tool, don’t send out an invitation and then within 24 hours, send an email asking them if they want to have a meeting, that person is just going to remove you from their network, because that’s what I do.  So it’s really understanding what does it mean to nurture a relationship? It’s not just, you know, expecting I’m going to connect with this person. And I mean, I can almost smell it, I could pull up a profile right away. And probably within a minute’s time, pretty much assess whether or not this person is going to be leveraging me within 24 hours as a prospect or not.


Andy Paul  26:33  

Oh, you can tell just by their connection request? Well, I mean, I think there’s a continuum there, which is what we’re experiencing is that, as we’ve seen, some managers just become so in some cases, they claim they have no choice, but, you know, so involved with the data that they forget sort of the human side of the coaching. And I think that thing just keeps sort of that’s behavior that’s modeled down into the salespeople. And we see it, again with why we have such low close rates in b2b sales, if we think that automation can do more than it really can. And it’s still a matter of people buying from people. And you’re not going to, you know, listen, I always say it depends. It depends on what you’re buying, right?


Keith Rosen  27:22  

If you’re going to the drugstore, it doesn’t really matter what you’re buying. If you’re buying something of substance, you’re probably going to want to like the person you’re buying it from.


Andy Paul  27:30  

Yeah. Oh, absolutely. And I think that’s been proven over and over and over again. So yes. A couple questions about your latest book on your day. Which I really like because it’s a great topic because it’s about owning your day and setting your priorities and knowing what is the most important. One of the chapters I really like that they want to talk about was just briefly in the time we’ve left is about getting away doing lists. And I’d had a difference with Kevin Cruz. He’d written a book on time management which had a very similar recommendation. I really, really enjoyed it so tell me why .


Keith Rosen  28:17  

I that seems to strike a chord with a lot of people


Andy Paul  28:20  

Yeah no it’s it’s very compelling.


Keith Rosen  28:32  

My thinking around this is that the to do lists actually create a lot more challenges for us some we realize if you have a separate to do list, which by the way many people do because I asked this question all the time when I’m working with doesn’t matter what audience most people have some to do list and I would ask them so at the end of the day, do you have your everything on your to do list checked off? And they would say No, and I would ask them what got in the way and they would say you know how it is Keith or something. One other thing that happened throughout the day, it’s hard to get everything done. And I would agree with that. So what are some other things on your to do list that are scheduled to be done in a week? You know, two weeks in three weeks? And people would inevitably say yes. So what if you could eliminate your to do list? And that’s what I would ask people that would say, well, Keith, no, I can’t . These are all the things I need to do. I say, wait a second timeout. I want you to look at your to do list. Is there anything in your to do list that you are doing at some level of consistency. Now some level of consistency could be anything from a year, to twice a year to once a quarter to once a month to every other week? A week a day doesn’t matter. any level of consistency. If the person says yes, I say I could just want you to put a little mark next to that, and they would go through this exercise, and I would ask them when they finish that how many things are left on your to do list and out of maybe say 20 things or 25 things out of after doing that one exercise that would say, Keith, I either have nothing on my list anymore, or I have maybe two or three things. And I want to ask them what those two or three, two or three things are. And they would tell me things like oh, well, you know what? My tires? My tires are going. I know I need to change them. The hole is in my backyard. It’s leaking. I need to get a different hose. Okay, anything else? No, that’s about it. But what have you noticed there? See a to do list is actually meant to be a list of things that has no level of consistency around. I don’t know when I’m going to the doctor unless I’m going for a checkup. In other words, I don’t know what I’m going to be sick of.


Andy Paul  32:32  

Yeah, that’s, I love that approach. That’s one of the reasons I want to talk about just to remind people because I think it’s a great construct for them to think about in terms of managing time as you get these recurring tasks that are in your calendar at a consistent time, this becomes routine, right? These things that you’re doing on a daily ongoing basis, because they’re generating long term value for you or your business. And then as you said, you get the other things that come up that you can’t predict. Then you know how to fit them into your schedule. And they’re not taking priority over the things that hatch that you’re really should the building blocks that you should be doing each and every day.


Keith Rosen  33:10  

And that’s when your to do list comes down to maybe 2 or 3 things rather than 20 or 30 things, because you’ve actually now scheduled in your calendar, and you’ve built some personal accountability to get them done at a time that you said you would.


Andy Paul  33:23  

Many things that at least I found, because I’ve taken an approach like that over the last year I said at Kevin Cruz had on the show talked about very similar philosophy and, you stop doing things that that aren’t really getting you to the goal that normally might say, Okay, well I’ll put them on a list and do and then you feel sort of comfortable that you got a bunch of things taken off your to do list, but those sort of consistent baseline things that you needed to be doing. You weren’t and you’re not really getting anywhere.


Keith Rosen  33:58  

You know, I always say a to-do list without a deadline is a diversionary tactic because then you’re never accountable for getting it done.


Andy Paul  34:08  

That’s a good expression. I like that. Alright, so Keith, on this last segment show, I just have some few questions, standard questions, I ask all my guests and they start rapid fire questions. You can give me one word answers or you can elaborate if you wish. So the first one is when you, Keith Rosen are out selling your products and services. What’s your most powerful sales attribute?


Keith Rosen  34:29  



Andy Paul  34:31  

I think you may have answered this next one. Who’s your sales role model?


Keith Rosen  34:34  

Ah, that would be Zig Ziglar. Only because I find him to be the most authentic, kind, ethical, moral person on this planet. He truly is a model of what other people aspire to be. And I’m not just talking to salespeople, I’m talking about human beings. He always put his family first. He always put his faith first. He put people first and that’s what made him extraordinary.


Andy Paul  36:25  

All right, last question for you. What music is on your playlist?


Keith Rosen  36:29  

Oh, my did you touch on a hotspot. I’m a music junkie.


Keith Rosen  36:49  

Well, I’m looking around the room because I went backstage from a bunch of them. Bruce Springsteen everclear Collective Soul wait Colors playing again. The other plant again I met all our lexicon about three times over the last year. 


Andy Paul  37:06  

I love their early stuff.


Keith Rosen  37:07  

Yeah, they’re amazing.


Andy Paul  39:25  

Excellent. Gosh sounds like an old movie. All right, perfect. Well, Keith, thanks for joining me and friends. Thank you for spending time with us. Remember, make a part of your day every day to deliberately learn something new to help you accelerate your success and easy way to do that. Make sure you join my conversations with top business experts like my guest today, Keith Rosen, who shared his expertise about how to accelerate the growth of your business. So thanks again for joining me and until next time, this is Andy Paul. Good selling everyone. Thanks for listening to the show. If you like what you heard, and want to make sure you don’t miss any upcoming episodes, please subscribe to this podcast on iTunes or Stitcher for more information about today’s guests, visit my website at AndyPaul.com