Brett Keirstead on Sales Coaching, Curiosity, and Human Judgment
About Brett Keirstead
Brett Keirstead is Chief Sales Officer with Chief Outsiders and a lifelong sales leader whose career spans BDR, SDR, account management, and CRO roles. He is the author of We're All Salespeople and focuses on scenario-based coaching that helps sales professionals strengthen judgment, curiosity, business acumen, and accountability.
Episode Notes
Key moments from this episode
Brett Keirstead joins Tailwind to make the case for sales as a demanding profession built on value, judgment, and continual practice. Drawing on a career that spans BDR, SDR, account management, and CRO roles, Brett explains why sellers must believe in the problems they solve before technique can help, and why leaders should coach through realistic scenarios instead of teaching canned responses. He explores how curiosity develops business acumen, why personal accountability separates reasons from excuses, and where AI belongs as a productivity and coaching aid without replacing human thought. The conversation closes with a practical leadership model: reinforce fundamental skills through regular practice, use a small set of conversational KPIs that support real decisions, and tailor qualitative coaching to the individual seller.
Takeaways
- Start coaching with the seller’s belief in the value they provide; technique is unlikely to survive pressure when that conviction is missing.
- Use realistic scenarios to expose how a salesperson thinks, then coach the judgment behind the response instead of supplying another memorized script.
- Develop curiosity and business acumen together by asking better questions about how the customer makes money and how the proposed solution affects the business.
- Build personal accountability into deal reviews by separating genuine constraints from excuses and asking what the seller could have influenced differently.
- Protect regular skills practice and focus measurement on two to four conversational KPIs that help leaders make decisions, leaving room for individualized qualitative coaching.
Key Moments
- 3:06
Treat sales as a profession that creates value
Brett frames professional selling as the responsibility to bring a useful solution to a real problem and to keep developing the craft throughout a career.
Read transcript at this moment - 5:25
Build belief before adding technique
A seller who cannot explain the value and distinctiveness of the work will struggle under pressure, so belief becomes the foundation for later training and objection handling.
Read transcript at this moment - 8:58
Coach judgment through realistic scenarios
Scenario-based practice reveals the reasoning behind a response and helps sellers build authentic judgment instead of reciting the same memorized answer as everyone else.
Read transcript at this moment - 16:10
Turn curiosity into business acumen
Better questions help sellers understand how customers operate, connect solutions to business impact, and develop the commercial perspective required for future leadership roles.
Read transcript at this moment - 23:24
Separate reasons from excuses in deal reviews
Top performers take personal accountability for what they can influence, examine lost deals without self-punishment, and use the review to identify better future choices.
Read transcript at this moment - 29:42
Simplify measurement with conversational KPIs
Two to four memorable metrics can keep teams informed and support real decisions while leaders preserve time for practice and coaching tailored to each seller.
Read transcript at this moment
Transcript
0:02 We have another episode of Tailwind.
0:04 Today we're joined by Brett. I should
0:06 ask you before Kirstad. Is it?
0:08 >> Yeah, Kirst. There you go.
0:09 >> There we go. All right. And we're
0:10 keeping it raw unedited as we both like
0:12 with it. So, hey Brett, tell us a little
0:14 bit more about yourself.
0:16 >> Yeah, sure. So, it's pleasure to talk to
0:17 you. I uh so I am a what what in the
0:21 world of sales now, I'm a a lifelong
0:24 salesperson. So I uh have had all the
0:27 roles everything from starting out when
0:29 I was 22 years old as a as a BDR SDR to
0:33 an account manager. I've been part of a
0:35 lot of different organizations all the
0:37 way up to CRO level roles and and uh
0:41 have always been a passionate advocate
0:43 of sales and five years ago I published
0:45 a book called we're all salespeople
0:47 which was really the premise that you
0:49 hear a lot when people say we're all
0:51 salespeople we all need to be selling
0:53 and so I published a book under that and
0:56 subsequent to that over the last several
0:58 years have really focused my time and
1:00 energy on coaching the next generation
1:02 you know sales is as we all know often a
1:05 tough industry you know it's like
1:07 lawyers politicians salespeople
1:10 >> and um and I have found however as a
1:13 passionate defender of our of our uh
1:16 profession that the value that a really
1:19 good salesperson provides to the to the
1:21 industry to the marketplace to the
1:23 clients is is is absolutely essential
1:27 and so I now I do a lot of coaching I
1:29 published a coaching app that does
1:30 scenario-based sales coaching which I
1:32 know we'll kind of get into today
1:34 >> and um and excited to be here. I I as
1:37 hopefully you'll see and everybody hears
1:39 I'm very passionate about this subject.
1:41 Um and I really think that it's the
1:44 greatest profession
1:47 talk about
1:48 >> it's too bad that there seems to be a a
1:51 general public perception of what a
1:53 salesperson is.
1:54 >> Yes.
1:54 >> What like a really truly trained great
1:57 salesperson is. And you it almost feels
1:59 like at some point in time maybe we need
2:01 to redefine one of those cuz they're not
2:03 they're not apples to apples.
2:05 >> Um I'm only what I'd say nine months
2:07 into like being like professionally
2:10 trained to be a real professional
2:12 salesperson.
2:13 >> Uh and I used to have like sales jobs
2:15 earlier in my career where it was like
2:17 here's here's a list of people to go
2:19 reach out to get after it versus now
2:22 being like trained and understanding
2:23 what I'm supposed to be doing. And I
2:25 just like these are two different
2:26 worlds. And like the more I learn about
2:28 it, I'm like this is this is not my
2:30 perception from any experience I've had
2:32 in the past. Um it's just it's it's not
2:35 fair. It's like
2:37 >> it's like unjust what's been done to
2:39 like the the profession itself.
2:41 >> Well, it's you know it's unfair because
2:43 look every there are terrible doctors.
2:46 There are terrible everything. You know
2:47 what I mean? And there are bad
2:49 salespeople. there are salespeople that
2:52 h have have caused damage to our
2:54 reputation in industry. But to your
2:56 point, I've tried to break it down and
2:58 and and part of prospecting, which is I
3:01 know the big part of the subject fits
3:03 nicely within it is a a truly
3:06 professional salesperson is their
3:10 responsibility is to bring to the world
3:13 to the marketplace a solution that meets
3:16 a real problem. Right? And and great
3:20 salespeople do that. And you could argue
3:23 like, wow, all the world's problems
3:25 would not be solved if some salesperson
3:27 didn't convince somebody that this they
3:29 had a resolution to the problem. Or else
3:31 people would just there'd be inertia.
3:33 People would not do it. We'd probably
3:34 still be in a horse and buggy
3:36 >> if somebody didn't convince somebody of
3:38 a good idea. So
3:40 >> in sales and that's why part of what
3:42 I've tried to do is bring that level of
3:45 positivity about what we do. the
3:48 importance of the role that we do all
3:50 throughout sales. You know, whether
3:52 you're a newbie that you're just getting
3:54 started in your career or you're
3:55 somebody that's been around for a long
3:57 time, fundamentally, we're still
3:59 delivering the same thing, which is the
4:02 market is out there, people are out
4:04 there with a need for better solutions
4:06 to resolve their issues. And a
4:08 salesperson has a moral obligation to do
4:11 it.
4:12 >> Um, and so, uh, that's really been my
4:15 philosophy. And so when I train and
4:16 coach young salespeople today or these
4:18 folks, I'm always like, you are doing
4:20 God's work. You know, as painful as it
4:23 is, as many people will tell you that
4:25 quit calling me or hang up on you or
4:27 curse you, you have to have a
4:29 fundamental belief in the work that
4:30 you're doing brings value um to the
4:34 market.
4:34 >> Yeah.
4:36 What are some of those core and
4:37 foundational things that as a sales
4:39 leader you need to bring to to create
4:42 this mindset mindset shift that you're
4:44 talking about?
4:45 >> Yeah. And and you know, kind of going
4:47 back to what you said before, a lot of
4:48 times people think, well, I'm not a
4:50 salesperson. I don't want to be a
4:52 salesperson. I don't call me a
4:54 salesperson. You have people that are
4:55 account managers and they work with
4:56 clients like, don't call me a
4:57 salesperson. I'm like,
4:59 >> what would you like for me to call you?
5:01 you know, um what when you're out there
5:03 and a customer articulates that they
5:05 have a need and you offer them a
5:07 solution
5:09 >> and they pay you for that solution, what
5:11 would you like for me to call you?
5:13 >> Um you know, they're like, uh I don't
5:15 know, salesperson like perfect. So part
5:18 of the part of the issue that I find a
5:20 lot in in coaching is that we and and
5:25 this happens a lot in the prospecting
5:26 stage from the very beginning is do you
5:29 believe in yourself and the service and
5:32 the product that you're offering and the
5:34 value it brings or not? Because if you
5:36 don't it's almost impossible especially
5:39 in today's day and age to fake it.
5:41 >> There's just too much coming. There's
5:43 too much noise. There's too much AI.
5:45 there's too much whatever. And if you
5:48 don't demonstrate a confident and
5:50 genuine belief in what you offer and the
5:53 value it brings, you'll crumble under
5:56 objections. So, from a coaching and
5:58 training standpoint, often the first
6:00 thing I want to assess and work with
6:02 people is, do they have a fundamental
6:03 belief in what they're doing?
6:05 >> Um, because you can go a long way with
6:09 passionate belief in what you do. Um,
6:12 and sometimes we're always focused on
6:14 techniques and did they ask the right
6:16 question and a lot of that stuff is good
6:17 and we can get to that, but it I like to
6:20 start with do you understand at a core
6:23 core in your core that what you're doing
6:26 and what you offer brings value.
6:28 >> Yeah.
6:28 >> Um, and you'd be surprised how many
6:30 people don't or they don't understand it
6:32 or they don't believe in it and it's
6:34 very very difficult. So, how do you uh
6:36 what are some tips or guidance or
6:38 recommendations, best practices to to
6:40 get to that understanding if they do or
6:42 they don't? Or is it pretty obvious the
6:44 second you start talking to them?
6:45 >> Well, a lot of times I there's one
6:47 exercise I do. I always call it the um
6:49 uh uh the trade show exercise for
6:52 salespeople. I said, "You ever work at a
6:54 you ever work a booth at a trade show?"
6:56 Like let's say you're in some industry
6:58 >> and you're the booth guy
7:00 >> and um
7:02 >> somebody's walking down the aisle and
7:04 they're stopping at every booth
7:06 >> and
7:07 you know they're like what do you do?
7:09 You know what do you do? And a lot of
7:12 times if you say roleplay that scenario
7:15 with somebody and say hey I've just seen
7:18 14 other people that sound just like
7:21 you. Tell me what is it that is unique
7:24 about you and us as an organization. And
7:28 it's amazing how many people struggle
7:31 with that. They'll start talking about
7:33 features or they'll say generic things
7:35 like, "Well, we have best-in-class
7:37 service stuff that the other 14 guys
7:40 said along the way." And
7:43 >> so by coaching through that exercise and
7:45 getting very detailed into can you under
7:48 pressure in a moment of truth when
7:50 somebody that's important is staring at
7:52 you and asking you to articulate what is
7:54 it that makes you and your company
7:55 unique to me. That's a really really
7:58 good exercise. It's not hard to
8:00 visualize the exercise, but you'd be
8:02 surprised. Um and obviously what we're
8:04 looking for is do you have a compelling
8:07 belief that what you offer is unique?
8:09 Whether it's the problems that you solve
8:11 for a client, the manner in which you do
8:13 it, those are the kinds of things that
8:15 you really want to fair it out.
8:18 >> So when you make that identification,
8:19 what's the the next step to take?
8:21 Obviously, if somebody believes, don't
8:22 mess with it, right? Or unless they
8:24 believe the wrong things, in which case
8:26 maybe tweak it. But what are the next
8:28 steps for somebody then to bring them
8:30 into that belief in
8:31 >> Yeah.
8:32 >> in the right head space. So, a lot of
8:34 what I try to do, and this is what my
8:36 application I developed. Um, I kind of
8:38 got to this realization. There's a lot
8:39 of really good training um, uh,
8:42 frameworks out there. You know, you hear
8:44 them all the time that spinelling or
8:46 Miller Heyman or Medpek or they're all
8:48 awesome, right? There's there's nothing
8:49 inherently um, wrong with any of them.
8:52 My angle though and to to to the way you
8:55 asked it is I try to think
8:58 I I try to replicate scenarios that
9:02 people encounter and then put the rep in
9:06 those scenarios and then coach them
9:08 through how they would perform. So for
9:10 example a scenario-based um and you know
9:13 objection handling and objection
9:15 training is is as old as time. You know,
9:17 when I was in 1990, you know, we went in
9:19 a classroom and we had a piece of paper
9:21 and we learned objection handling. So,
9:23 the idea of objection handling is not
9:25 new. The tools are better. You know, the
9:28 things that we can do today make it a
9:29 little bit easier, but the core
9:30 principle hasn't changed. And so, what I
9:32 try to do is create these scenarios and
9:36 try to get reps to talk through their
9:39 thought process. I don't want people to
9:42 memorize
9:44 um memorize things because as you
9:47 imagine in today's day and age in in
9:50 inauthenticity the opposite of it
9:52 inauthentic memorized responses will
9:55 they'll get you nowhere. Um every
9:58 communication today is designed to be
10:00 very unique and specialized for you to
10:02 get through. So the only way to do that
10:04 is to put reps in scenarios and then
10:07 coach them through that. So, I might
10:08 say, "Hey, what happens when someone
10:10 says, "We really like your proposal, but
10:12 we're going to look at a competitor's
10:14 first." What do you do? You know, what
10:17 do how do you think through that
10:18 scenario? What would you do? And so,
10:20 roleplaying, not just the the
10:24 memorization,
10:26 but really understanding how they think
10:29 is really been what has been a secret
10:32 sauce for me. I don't want to teach
10:34 robots that hear something and respond.
10:37 I want to teach people to think and
10:41 strategize and understand. And frankly,
10:44 one of my fears about AI,
10:47 as you can guess, is people deferring
10:51 thought and strategy to the tool
10:55 um as a as a deterrent to them thinking
10:58 through it. I'll give you a good
10:59 example, right? How many you'll see a
11:02 lot of and there's so many good tools
11:04 out there. My buddies over at Gong have
11:05 a great tool and they'll be like, "Well,
11:07 Gong's great because you put the call in
11:08 and it tells you all these things." I'm
11:10 like, "Okay, but did I internalize
11:12 that?" Like, how do I as the manager
11:15 help the rep internalize that issue and
11:18 really make it their own versus reading
11:20 what some AI said I didn't do well,
11:22 >> right?
11:23 >> Um, and again, that's nothing against
11:25 the tool. It's kind of your question.
11:26 And how do we as leaders
11:29 develop young people or salespeople in
11:32 these areas around tough things like
11:34 prospecting? It's by helping them think,
11:37 not just I'm going to plug it into AI
11:40 and it's going to tell me what to do.
11:42 >> Yeah. And if you plug it into AI and it
11:44 tells what to do, you're going to sound
11:45 like everybody else and start losing
11:47 that human aspect of it. I mean, I think
11:50 it's almost one of those things where it
11:52 it's shifted the market in a way that's
11:54 really interesting and there's a lot of
11:56 fun around like, hey, what's capable of
11:58 doing and then it's also just uh
12:01 completely uh created a ton of value in
12:03 the human aspect and human relationships
12:06 that I think is it's starting to boil
12:08 out. The more people I talk to, the more
12:09 people are like, you know, I don't want
12:11 the AI, I want this, I want the human
12:13 interaction, I'll take the mistakes,
12:14 I'll take that. Part of it is like at
12:16 the end of the day like if AI is in your
12:19 sales process um and it becomes more and
12:22 more a part of it you people are going
12:24 to start interpreting that as okay cool
12:26 and then when something breaks I'm going
12:27 to get an AI bot not a person and I'm
12:29 going to get the script and not a person
12:31 because you've shown me during the sales
12:34 process who you guys are which is not a
12:36 human element that I need when things
12:38 are truly truly bad bad um not to say
12:41 that AI doesn't shouldn't be involved
12:43 >> it just should be involved in the right
12:44 places.
12:46 >> Amen.
12:47 I think it's kind of like um you know
12:49 for us old school sales people it's kind
12:51 of brings a tear to my eye because look
12:53 in 1990 when I started as a salesperson
12:55 I had a a handwritten note with check
12:57 marks you know I'm like one I made a
12:59 call two here's my rolodex you know I
13:01 rolled it up and um it's interesting
13:04 though because the logic that happened
13:07 then is the same logic as today
13:10 consistency work on your approach target
13:13 your message you know follow through We
13:16 didn't have the same tools, but the
13:18 fundamental issue hasn't changed. What I
13:20 like about what's
13:22 >> what I like about what you just said is
13:24 I feel like
13:26 >> the the last x number of years of
13:29 selling has become so hyperfocused on
13:32 automation
13:33 >> that in a lot of ways we're losing the
13:36 essence of onetoone communication. So I
13:40 have a lot of clients they're like he's
13:42 like I'm just driving out in my
13:44 territory and knocking on doors. I'm
13:46 like, "Oh, I better start crying." You
13:47 know, I'm so happy. You know, and part
13:49 of that is the postcoid hangover when
13:52 everything went into the COVID world,
13:53 everything became non non-human
13:55 interaction. But I think now we're
13:57 starting to swing back hopefully towards
13:59 middle ground, which is human
14:00 interaction, human relationships,
14:02 conversation, and then AI as a
14:04 productivity tool on the back end to
14:06 kind of help me maybe expedite my
14:08 coaching a little bit, speed up the way
14:10 I handle some things. But I'm going to
14:12 differentiate myself again by being a
14:14 good human person.
14:17 >> And it comes down to to your earlier
14:19 point which is the thinking part. How
14:21 does that individual rep think? Um and
14:24 so when you were talking about that, you
14:25 know, how do I coach them up to to
14:27 internalize the problem to think about
14:28 it? What are some of the things that you
14:29 see that are most common commonly needed
14:32 coaching points uh for like bringing the
14:35 reps to the next level to really start
14:37 becoming more than somebody who just
14:39 kind of follows the script which is fine
14:40 to start at some you know you got to get
14:42 the rep movement but
14:44 >> what does that next step look like most
14:46 often
14:46 >> the the thing that I really I I um and
14:49 I'll give you a quick story on that when
14:51 I started um I was a finance major and
14:52 accounting major in college I went to
14:54 Clemson and I was like I'm going to go
14:55 be a finance guy you know I had
14:57 internships in finance And right before
15:00 um I took my first job, my mentor at the
15:03 time, he said, you know, and he said,
15:06 "You ought to try sales." And I always
15:08 laugh because people think you can try
15:11 sales. No one says you should try being
15:14 a doctor, you know, or you should try
15:16 being a a lawyer. It's like for some
15:20 reason people believe that sales is
15:22 something you can try. And I've been an
15:23 advocate to say we need to stop saying
15:25 that because
15:26 >> like you've learned.
15:28 >> Yeah.
15:28 >> A sales professional is like an
15:30 accounting like a CPA. Every year
15:32 there's new rules. Every year there's
15:34 new techniques. If you were a CPA and
15:37 you were using the tax code from six
15:39 years ago, you'd never be fired. Well,
15:41 if you're a salesperson and you're using
15:42 techniques from six years ago, you'd be
15:44 fired. So, I do like to think. But so so
15:48 when I got into this whole sales I I've
15:51 I've I've always tried to realize that
15:54 that it is a um it is a profession.
15:58 >> Um it is is it is something to
16:00 specifically work on. So you know when I
16:03 look at today and I look at some of
16:05 these things that I try to work on sales
16:08 people we talked about thinking the way
16:10 I like to do it is that basic curiosity
16:14 of a salesperson the ability to
16:18 be in a situation and have a curiosity
16:20 is really important and so people say
16:22 well like you said how do you train to
16:24 that
16:25 >> and I've said one of the things that
16:27 organizations do is they teach so much
16:30 what to say and not enough what to ask
16:33 >> as if saying the perfect thing is being
16:37 a great salesperson. I say the opposite.
16:39 Actually asking the great question
16:42 >> is what makes a salesperson great. And
16:44 so um what happens is so what I try to
16:48 do is I try to help salespeople ask good
16:51 questions.
16:52 >> How that manifests itself career-wise is
16:55 and this is really an important person
16:56 for somebody that has aspirational
16:59 goals, right? is the higher up the
17:03 higher up you go in an organization the
17:06 more business acumen is important
17:09 >> you know if you just all you care about
17:10 is selling deals and all I want to do is
17:12 sell
17:13 >> you don't necessarily develop a clear
17:16 understanding of how does my product or
17:20 service impact a business all you care
17:23 about is did they buy it or not and I
17:26 think that's a very limiting
17:28 factor you might win deals you You might
17:31 just pump them through and that's fine.
17:33 But if you have aspirations career-wise,
17:35 you have to understand business acumen.
17:37 So, a kind of nice thing is is again I
17:40 started in payroll sales at Seridian,
17:42 the payroll company. And so, I went into
17:44 all these different companies from all
17:46 these different types of businesses and
17:48 I'm like, "Oh, wow. That's interesting.
17:50 How does your business make money? How
17:52 does a meat products byproducts company
17:54 make money?" You know, how does a
17:56 trading cards company make money? So, I
17:58 think the what I what I the the double
18:01 win for the curious salesperson is when
18:04 they're asking questions and they
18:05 understand how does my business how does
18:07 my product and service impact your
18:08 business, they're also developing acumen
18:11 that they're going to use later in a
18:12 career if they want to get into
18:13 executive roles or a CRO or even a CEO
18:17 for all that matters. So, I think that's
18:19 the I know that was a little bit of a
18:20 long answer to the question of I try to
18:23 make sure the best salespeople
18:26 understand the business impact of what
18:29 they're doing, not just what are its
18:31 features and benefits and how much does
18:33 it cost.
18:34 >> Yeah,
18:35 >> that skill transfers all the way in your
18:38 career.
18:38 >> Yeah. What what's uh what's interesting
18:40 is as you're talking through that um I
18:42 was having flashbacks to when I was
18:43 getting my MBA and they made us do these
18:46 Harvard case law or not case law Harvard
18:48 business review like things and we we
18:50 read them all and we diagnose the
18:52 problem and we'd think about it
18:53 >> and you know so on and so forth and then
18:55 like
18:56 >> you know I took like an entrepreneur
18:57 course and all this kind of stuff and
18:59 we're we're dancing around the entire
19:01 time what what actual sales is and the
19:04 big knock that I always have is like
19:07 >> they don't teach the sales part though,
19:09 which is going in and having authentic
19:11 conversations and being genuinely
19:14 curious. And I feel like you could
19:16 easily substitute sitting down and being
19:18 like, "Okay, here's the piece of paper,
19:20 read it, diagnose the problems, offer a
19:22 solution in an academic sit down at your
19:25 desk way." It's like, why don't you just
19:27 send them to businesses that have agreed
19:29 to work with you and then you have to do
19:32 the sales process, learn it that way,
19:35 come back, report on it, look, make it a
19:37 salesunnel versus
19:39 a paper, like actually have a salesunnel
19:42 instead of a paper. I think the amount
19:44 of like uh retention and application and
19:47 understanding of how business actually
19:48 works would go through the roof in
19:50 comparison to just sitting down and
19:52 looking at things like in a dry dull
19:55 academic way where it's like you know
19:57 starting a business has taught me more
19:59 than an NBA program ever could.
20:01 >> Absolutely.
20:02 >> Why not just have them people actually
20:04 actively selling and doing this B2B
20:06 sales in specific to to really learn how
20:08 you know businesses work and how people
20:11 like considered how things go? I mean,
20:13 you know, there's one thing to be like,
20:14 "Hey, we fit this problem." The other
20:15 thing is to be like, "That's not their
20:16 biggest problem, so they don't have
20:17 attention for you."
20:18 >> That's right. That's right.
20:20 >> So, it's this whole other mindset of
20:21 like, you know, this curiosity shift and
20:24 then like actually
20:26 >> wanting to dig in and understand how
20:28 you're helping their business versus can
20:29 I get the credit card swiped.
20:31 >> Yeah. And that's and and so that goes
20:32 back to what we started with.
20:34 >> Yeah. If if if if people people good
20:39 sales people do what you just said, not
20:42 there to get the credit card swiped, you
20:45 know, that is the transaction portion of
20:47 it. If that's what you're in it for, you
20:50 can you can be successful that way.
20:52 Don't get me wrong, but if that's what
20:54 your motivation is, and I'll always
20:56 people say, I'm money motivated, so I
20:57 got into sales. I'm like, that's the
20:58 worst reason, you know, because then
21:01 you're going to make decisions at times
21:03 that are beneficial to you and not to
21:05 the client. And that might work in the
21:07 short run, you know, trust me, that can
21:09 always work. Pushing, that's that's how
21:10 sales people get a bad reputation. But
21:12 if you get into it and say, you know, I
21:15 believe very strongly in the um the
21:19 importance of solving issues. I'm a
21:21 problem-solving type person.
21:24 >> This is a great place to be. And I think
21:26 a lot of times people think, "Oh, you
21:28 should hire for somebody that's affable
21:29 and they have a great personality and
21:31 they're fun to be around,
21:32 >> but some of the best salespeople I've
21:34 ever managed are stoic.
21:38 >> They're very methodical,
21:40 but they're very credible and they're
21:42 very client focused and they're very
21:44 solutionoriented."
21:45 And um in today's day and age, you know,
21:48 I think with so much noise and scrutiny,
21:50 people want to interact with trustworthy
21:52 people, humans that work for them, that
21:55 understand them, um that's really a
21:57 differentiation. So, you know, if you're
21:59 out there thinking about sales or you're
22:01 just getting started and you're like,
22:02 I'm not funny enough or I'm not I'm I'm
22:04 nervous. Like, don't worry about it.
22:06 Don't worry about it. It takes all
22:08 >> We're a we're a we're a a welcoming
22:11 community in sales, you know. There's uh
22:15 we have room for everybody.
22:17 >> Yeah. Yeah. And I think uh you know an
22:20 interesting part of all this is like you
22:22 can you can go for the transactional but
22:24 that's always going to be a race to the
22:25 bottom in terms of pricing and it's
22:27 >> you know Walmart, Amazon, you know these
22:29 people have already cornered the market
22:31 on the race to the bottom. Like you're
22:32 not going to beat them to the race to
22:33 the bottom. You sure can break out with
22:35 like a premium offering that is but you
22:38 know what comes with that is the
22:39 relationship that you're talking about
22:41 the I'm doing what's in their best
22:43 interest not in my best interest per se
22:46 and then you know it takes longer and
22:48 it's a little bit more you know complex
22:50 to navigate but then you end up being
22:51 able to offer a higher premium product
22:53 because you're also you know selling the
22:56 relationship or establishing and
22:58 building and you know creating trust
23:00 with the two organizations. So when
23:04 please no go. I just want to add one
23:05 more point to the question you asked
23:07 before which I thought was really good
23:08 just about like you know what do you
23:09 what is the differentiation or what do
23:11 you try to coach and teach sales people
23:13 and I'll tell you one thing that I found
23:15 in the top performers that I've I've um
23:18 managed over the years is they have an
23:20 un
23:22 unwavering
23:24 sense of personal accountability
23:26 >> and um you know I always say there's a
23:29 difference the thin line between reasons
23:31 and excuses you know very very rarely is
23:34 something a compelling reason, you know,
23:36 like it's an actual reason you could not
23:38 win a deal.
23:39 >> Most of the time there's some version of
23:41 excuse. So someone will say something
23:42 like, well, our price was our price was
23:45 higher.
23:46 >> Yeah.
23:46 >> So what could I do? Right? That's an
23:48 example of an excuse, not a reason,
23:51 right? Um and so if it's like, hey, we
23:53 can't conduct business in a country, and
23:55 they conduct business in that country,
23:57 that's a reason. Like there's nothing
23:58 you could do about it. But more often
24:00 than not, it's excuses. And so I found
24:03 when I coach sales people, I'm always
24:05 like, you want to assume that in almost
24:08 every deal that you did not win, it was
24:11 your fault.
24:12 >> And fault isn't necessarily like I'm
24:14 going to be miserable about it or I hate
24:16 myself or I stink, but fault is this
24:18 belief that had I made different choices
24:21 along the way and done things
24:23 differently, I had complete control of
24:25 the outcome. Sales is easy to blame
24:27 other people. I can't tell you how many
24:29 I'll call them, you know, tier two
24:31 salespeople or tier three that it was
24:33 always somebody else's fault. The
24:35 competitor had a feature, the client was
24:37 stupid, my price was too high, right?
24:40 That's a loser mindset. And um so I
24:43 always try to make sure whenever we're
24:44 doing deal reviews or anything, are we
24:48 sure that we are doing everything within
24:51 our ability to influence that? And um
24:54 and if it doesn't go our way, we want to
24:56 understand what is it that we could have
24:57 done differently. So I do think that's
24:58 just a winner mindset. Whether you're a
25:00 BDR, an SDR, an AE, an AM, a CRO, it
25:04 doesn't matter any anywhere in that is
25:06 just this belief that I control my
25:08 destiny in a sales process.
25:11 >> Yeah. And this is like a perfect segue
25:13 into where I was going to ask, which is,
25:15 you know, as you're getting the shift
25:17 from am I saying the right things to am
25:18 I asking the right things? It sounds
25:20 like, you know, during deal reviews,
25:22 what are the reasons versus what are the
25:24 excuses? You know, probably do they
25:26 understand what the business is and what
25:28 they're truly solving? Like, how are you
25:30 making sure that that transitions
25:32 happening? Because like, sure, they
25:33 could also just read the question and
25:35 then now you got to figure out what how
25:37 they internalized it and how do I crack
25:40 their brain open and see how did they
25:41 internalize it?
25:43 >> Yeah. And I think I think it's kind of
25:44 one of the um honestly one of the
25:47 shortcomings that I think of of sales
25:50 leaders in today's day and age.
25:52 >> Um and it's the businesses, you know,
25:55 contributor to it is
25:57 >> we're so focused on results
26:00 >> and did you win it and did you not and
26:02 what was your win rate and what are the
26:04 statistics and the KPIs and how many
26:06 dials you make and what's your quota.
26:08 like we're so driven by that performance
26:12 that coaching, inspection,
26:16 visibil that that side of it gets pushed
26:19 aside. It's like the last thing on the
26:21 list. So honestly, what's the quote? You
26:24 know, 90% is showing up. Mhm.
26:27 >> The biggest issue is just having sales
26:31 managers, leaders, coaches, train,
26:33 whatever it is, take the time and and
26:37 enforce the discipline of practice.
26:39 >> Yeah.
26:40 >> Um it's so so hard today because there's
26:44 so many pressures to produce
26:46 >> that all we care about is did you win
26:48 this deal or not and why and how much is
26:50 your performance? And unfortunately
26:54 the exercise the the motion of coaching
26:57 training has gone by the wayside. Before
26:59 this Zoom call I had I have one of my
27:01 clients we do three uh one a week 30
27:05 minute they they put in a scenario we
27:07 all respond and then we talk through it
27:09 as a group. It's a quick hit but it's
27:11 just practicing the drills. Enforcing
27:14 that discipline is where I think a lot
27:16 of companies and a lot of sales leaders
27:18 fall short. Um, so I don't want to
27:20 There's a million different ways to do
27:22 it. There's a lot of different ways to
27:23 do it, a lot of tools to do it. But
27:25 >> the bigger problem is just doing it.
27:27 Having the mindset as a leader and as a
27:29 team, we're going to work on basic
27:32 fundamental skills.
27:34 >> Um, and and and we're not going to put
27:37 it aside. It's not going to be like the
27:39 last thing on the last day if we get to
27:41 it.
27:41 >> Yeah. So, I mean, it's almost like this
27:44 is not a complex, you know, thing. It is
27:47 not complex to like figure out what's
27:49 going on. Engage in the regular practice
27:51 of coaching and you know interacting
27:53 around those business problems and it'll
27:54 start coming to the top and flushing
27:56 everything out.
27:57 >> It does. I mean and and listen I don't
27:59 want to prescribe one style. Somebody
28:01 I'm I'm a I'm a I grew up in New Jersey.
28:03 I'm very you know like this you know I'm
28:05 excitable. Um but that's not the only
28:08 way to do it. I mean and and I realize
28:10 as a leader sometimes people don't like
28:11 that. you know, I have salespeople that
28:13 are more reserved, you know, and they
28:15 want a a slower, more methodical
28:17 approach. Um, and so just working
28:19 individually, and that's why I don't
28:21 like to say there's only one way to do
28:24 it. There are a lot of different ways to
28:25 do it. There's a lot of different ways
28:26 to coach, and there's a lot of different
28:28 personalities that you're dealing with,
28:30 but um, there are some fundamental
28:33 skills. Like I said, I don't care where
28:34 you are. I don't care whether you're
28:36 funny or loud or quiet. If you don't
28:37 have curiosity, you're probably not
28:40 going to be successful in sales. in in
28:42 any role. Um just because this sincere
28:45 desire to learn about others and help
28:48 them be successful is a core tenant of
28:51 long-term sales success.
28:53 >> Yeah. Um so if I'm working in an
28:56 organization uh and I'm saying, "Okay,
28:59 this is great. I do feel like we're
29:00 overrun by KPIs. We're not we're not
29:03 focused on this other stuff." if I'm an
29:05 AE, if I'm a frontline leader, and if
29:08 I'm, you know, a higher up leader, you
29:10 know, what would be your advice to each
29:11 of those levels on how do I start that
29:13 cultural shift to uh to looking at the
29:17 KPIs and understanding them and having
29:19 them inform but not having them dominate
29:21 and, you know, rule the day and have
29:24 like box everything else out. Yeah, it's
29:27 it's super interesting and I could spend
29:28 30 minutes answering that one question,
29:30 but um what's interesting because um the
29:33 way the term I the term I like to use is
29:35 I think it's absolutely critical in the
29:37 day-to-day um function of a business to
29:40 have some KPIs. The term I like to use
29:42 is conversational KPIs.
29:44 >> So conversational KPI is just simply you
29:47 and I are walking, we're talking and
29:49 like, hey, how's business? You know,
29:51 what the numbers look like? And I I have
29:53 two or three things that I tell you that
29:55 give you an essence of how the business
29:57 is performing. Like that's absolutely
29:59 important. Even if it's some and
30:00 different organizations, different
30:02 places, it might simply be, "Hey man,
30:03 it's been a great week. I set eight new
30:04 meetings." Great. That's a
30:06 conversational KPI, right? I didn't need
30:08 to see some gigantic report.
30:11 >> Um so I because I do think there are
30:13 some metrics that we should know. You
30:15 know, hey, my pipeline the next 90 days
30:17 looks good. It's about three times.
30:19 We're good shape. Great. Thanks. Good to
30:21 know. go about my day, right? So, I'm
30:24 not an anti-KPI person, but as I've
30:27 learned over my career, especially in
30:28 working with private equity and others,
30:30 you can make the numbers tell any story
30:32 you want.
30:33 >> And so,
30:35 sometimes that's where we get hung up is
30:37 in a very KPI oriented. So, again,
30:40 summary on the KPI side is two to four
30:44 conversational KPIs. And again, if I'm
30:46 talking to my boss, I'm managing up, I
30:49 tell my boss, here's this number. If I'm
30:51 managing across, I'm telling our
30:53 implementation team, here's that number.
30:55 If I'm talking to my reps, I'm managing
30:56 down. I'm talking to them in a certain
30:58 way. So, this management, managing up,
31:01 down, and across is another philosophy I
31:03 always said. In every role you're in,
31:04 you've got a boss, you've got peers, and
31:06 you've got people that you know, you or
31:08 down, and I don't mean look down on, you
31:10 know what I mean? Like organizationally,
31:11 that's the way it works. And so,
31:13 >> each of those titles you mentioned has a
31:15 different responsibility and a different
31:17 constituency. And from that they develop
31:20 their conversations around it.
31:22 >> Um and so I think the KPI piece is
31:25 critical on the on the let's call that
31:27 the quantitative side.
31:29 >> Yeah.
31:30 >> You know on the qualitative side what I
31:32 find is that you want to try to do
31:36 things what is the you want to
31:40 you want to try to do things in a
31:43 collaborative way and and and also in a
31:47 personalized way. And what I mean by
31:48 that is I know we all in the world
31:51 everybody needs to be treated the same.
31:52 We should treat everybody the same. And
31:54 I'm like, well, we should treat
31:55 everybody with respect, but when it
31:57 comes to coaching and development,
31:59 everybody shouldn't be taught the same
32:01 because everybody has their own unique
32:03 area. Somebody's really good at
32:05 discovery, but they're not good at at
32:07 closing or someone's really good at
32:09 technical and they're not good at this.
32:10 So I do think one exercise is paying
32:14 very individualized attention to what
32:17 each individual person needs whether
32:19 that's through an assessment or whatever
32:21 it is and then getting together and
32:23 making sure that those your message your
32:26 coaching your engagement with them meet
32:28 you know what's the quote meets them
32:29 where they are
32:30 >> in that regard. I think that's really
32:32 the essence of it. So you've got a
32:34 quantitative side which are
32:36 conversational KPIs depending on who
32:38 you're talking to and then the
32:40 qualitative pieces. Am I working with
32:42 each individual where they are on things
32:44 that I know are most impactful to them?
32:46 >> Yeah. Yeah. I like the idea of
32:49 simplifying the quantitative to make
32:52 space for the qualitative.
32:53 >> Absolutely. Then yeah within that so
32:56 that feel like that's got to be if you
32:58 are overrun by qualit or sorry
32:59 quantitative uh the first step is start
33:03 making it manageable
33:05 >> so you can create space
33:07 >> how do I convince somebody else that
33:09 that's worth doing like how do I how do
33:11 I go hey this we are overrun by numbers
33:13 and somebody goes I love my numbers I
33:15 don't care what you have to say
33:16 >> well I think the question is so I always
33:18 like to ask based on the numbers the the
33:20 simple ask is based on the numbers that
33:22 I provide to you what would what would
33:24 cause us to change the direction of of
33:26 our business if I told you what what
33:28 would cause you to change if you said
33:30 well we're we're ex so I have a I'll
33:33 give you a good example so I have a
33:35 client that is in the professional
33:37 services business right so they have
33:39 billable workers that are an allocation
33:42 of billable workers that they want to
33:45 plan the time out they want 80 to 85%
33:47 utilization rate of their workers okay
33:49 so if I'm the business it is reasonable
33:52 for me as a salesperson
33:54 I I need to provide them a piece of data
33:58 that tells them what is their future
34:00 utilization going to look like. Do I
34:02 need to hire more? Do I need to start
34:04 thinking about cutting back hours? That
34:06 is a very useful use case for data.
34:09 >> Yeah.
34:09 >> Right. Um and so I always like to ask,
34:13 what are the pieces of data that I can
34:14 provide to you that will cause you to
34:17 make a decision about the business?
34:19 >> Yeah. Hey, our our our quota, our
34:21 pipeline is terrible. It's really low.
34:24 We should invest in that area. Or yikes,
34:27 90 days from now, I'm looking at cash
34:30 flow negative business. Like, I need to
34:32 know that. So, I always like to push
34:35 back and say, listen, among all the
34:36 pieces of data we look at, which ones do
34:39 you look at to make decisions around?
34:40 And I'll make sure that those are
34:42 excellent.
34:43 >> Yeah.
34:43 >> Um, that's the best way to push back
34:45 because it look that is true. Like I
34:48 don't know what do you want me to do
34:49 with the data.
34:51 >> Yeah.
34:51 >> I don't know. I just want to know. It's
34:53 like well okay. You know if it makes you
34:56 happy and you're the boss, well you're
34:57 the boss. You know it's your name at the
34:59 bottom of the paycheck. So I'll do it.
35:01 But I would prefer to provide data that
35:05 in a timely manner that allows them to
35:08 make informed decisions.
35:10 >> Yeah.
35:10 >> That's that's the best push back. And
35:12 again that goes back to the whole
35:13 business acumen comment.
35:15 Do you understand what this data is for?
35:17 >> Yeah. It's almost it's almost like
35:19 you're suggesting that we should apply
35:20 the sales process to the change
35:22 management process.
35:23 >> We're all sales we're all sales.
35:25 >> We're all sales people.
35:27 >> It's almost like we should all read the
35:28 book even if you're not in that room
35:30 because like you know people are people
35:32 are project managers that have ideas
35:34 that they want to have rolled out to the
35:35 rest of their you know their unit.
35:38 >> Go read the book. figure out how to
35:40 then, you know, do the sales process to
35:42 get up, down, and uh center on board and
35:45 moving forward by actually applying
35:47 curiosity and, you know, tying your idea
35:49 to the, you know, biggest problem and
35:52 being able to like move things forward.
35:54 >> Yeah. And and and the and the reason and
35:56 we can, you know, the reason why I wrote
35:57 and again, I'm not trying to promote the
35:59 book. I'm just giving you the context of
36:00 it is that the the reason why is that
36:03 sales great salespeople have five
36:05 fundamental skills. They understand
36:06 themselves. They know what they're in.
36:08 They know their product. They know their
36:09 service. They sincerely care about
36:11 others, right? I ask you I I care and I
36:14 ask you good questions. I also um I I I
36:17 understand outcome so I don't waste your
36:19 time. Like, hey, here's what we're here
36:20 for. Here's what you're trying to
36:21 accomplish. Here's what I'm trying to
36:22 accomplish. Then they're then they um
36:25 negotiate, right? Because when people
36:26 don't agree, sometimes people think of
36:28 negotiation as car, but I always say,
36:31 I'm married. My wife's family lives in
36:34 the Carolinas and mine lives in Florida.
36:36 So we negotiate where are we going you
36:38 know that's a negotiation right so
36:40 that's a skill and then the last one is
36:42 closing and as a salesperson you know
36:45 until the deal is closed it hasn't
36:47 happened so we might say um hey uh would
36:51 you donate to my kids baseball team oh
36:53 sure and then they don't well you didn't
36:56 close the deal right so these
36:58 fundamental good skills are necessary
37:00 everywhere and so um I try to teach that
37:03 and it's funny quick story on that. You
37:06 know, when COVID hit and right around
37:08 2020 and obviously that was at the the
37:12 summit of political negativity and what
37:16 social media unfortunately has done to
37:19 young people is when I don't agree with
37:21 something I consider that person I call
37:25 them names. I fight. But as a
37:27 salesperson,
37:28 >> if someone said your price is too high,
37:30 what? You're an idiot. You can't say
37:32 that. you know, like that would never
37:34 work, right? But that skill of how do I
37:37 handle an objection? How do I deal with
37:39 somebody that disagrees with me is a
37:41 life skill
37:42 >> and u and that was the premise of it.
37:44 So, like you said, if I'm a good project
37:45 manager and I have an idea that I think
37:47 can help my business. If I can't
37:49 communicate it, it ain't going to
37:50 happen.
37:51 >> Yep.
37:51 >> So, I am a salesperson
37:53 um in that regard. So, anyway, it's it's
37:56 we could go on and on and on, but then
37:57 anyway, that's kind of the the premise
37:59 of that topic in that regard. Well, we
38:01 are we're up. We're past time, which of
38:03 course was great. It was a great
38:05 conversation. So,
38:06 >> we're going we're going.
38:07 >> Uh, but I I do have another meeting I
38:09 gota run to, which is
38:10 >> Yeah, of course. No worries.
38:12 >> But before I let you go,
38:13 >> you know,
38:14 >> for anybody listening, you know, again,
38:16 sales is a very hard career, but I I I'm
38:18 excited to have you and in it, young
38:20 people, new people coming into our
38:21 career. It's a great way to make a
38:24 living. It's a great way to make a
38:25 contribution. And so, you know, stick
38:27 with it, man.
38:29 >> Yeah. Brett, it's almost like you also
38:31 run a podcast and you knew exactly what
38:33 I was gonna do, which was ask how do you
38:35 want to summarize this one big takeaway?
38:37 And that sounds like a perfect one.
38:39 >> Yeah. The big takeaway is this is the
38:40 greatest. It's a great profession. It is
38:42 very, very hard to do and there's more
38:45 nos than yeses.
38:47 >> Yeah.
38:47 >> Um but it's incredibly rewarding because
38:49 if you're doing it well as a
38:50 professional, you're definitely helping
38:52 people. You're solving issues. are
38:53 helping people bring things to them that
38:56 they otherwise may not do because of our
38:58 natural hesitancy as humans to just I'm
39:01 just going to do what I'm going to do,
39:03 you know? And so it's a very rewarding
39:04 career. It's it's it's great. And so
39:06 everybody who's listening on here, keep
39:08 it up, man.
39:09 >> Keep going.
39:10 >> Brett, thank you so much. I appreciate
39:11 it.
39:12 >> I appreciate it, man. Have a good one.
Questions answered in this episode
How should sales leaders coach people beyond memorized scripts?
Put sellers into realistic situations, ask them to explain what they would do, and coach the reasoning behind the answer. Scenario practice helps the rep internalize judgment and adapt authentically when a customer says something unexpected instead of waiting for a canned response.
Why are curiosity and business acumen important for salespeople?
Curiosity shifts the seller from trying to say the perfect thing toward asking useful questions about the customer and the business. Understanding how a company makes money and how a solution affects it improves the current conversation while building the commercial judgment required for account, CRO, and executive roles.
How should sales teams use AI and KPIs without weakening human judgment?
Use AI as a productivity or coaching aid, but require managers and sellers to think through and internalize what the tool reports. Keep quantitative management focused on two to four conversational KPIs that can inform a decision, then pair those numbers with individualized coaching, accountability, and regular skills practice.
