Casey Jacox on Humility, Curiosity, and Vulnerability in Sales
About Casey Jacox
Casey Jacox is the Founder of Winning The Relationship, a sales coach, speaker, author of Win the Relationship, Not the Deal, and host of the Quarterback DadCast. A former national top-performing sales representative for 10 consecutive years, he helps sellers and leaders use humility, vulnerability, curiosity, deliberate practice, and strong expectations to build more authentic relationships.
Episode Notes
Key moments from this episode
Casey Jacox joins Tailwind to explain why humility, vulnerability, and curiosity form a practical foundation for better sales conversations. He shows how genuine interest, empathetic tone, and thoughtful follow-up help sellers remove ego, listen for what matters, and create what he calls holistic differentiation: the way a buyer feels after the conversation. Casey offers a simple opening question that uncovers the customer’s definition of a successful meeting, then makes the case for replacing dreaded role play with deliberate practice. He also explains how post-call recaps, specific feedback prompts, and a willingness to study mistakes turn gaps into learning opportunities. For sales leaders, Casey connects vulnerability with psychological safety, critical thinking, and confidence, encouraging leaders to share their own failures so teams can learn without fear.
Takeaways
- Lead with humility, vulnerability, and curiosity so ego stays out of the conversation and the buyer feels genuine interest instead of a rehearsed sales performance.
- Ask what would make the meeting successful for the buyer before following the prepared agenda, then use thoughtful follow-up questions to understand why that outcome matters.
- Treat sales practice like athletic practice: rehearse a few minutes every day, build fluency with tell-explain-describe questions, and learn the stories behind strong customer outcomes.
- Slow down after calls to align the internal team, document what mattered, confirm commitments, and send the customer a recap that invites corrections or missing context.
- Request specific feedback, study the gaps without self-punishment, and have leaders model vulnerability so sellers can think critically, learn from failure, and keep their confidence.
Key Moments
- 0:40
Build the humility-vulnerability-curiosity flywheel
Casey introduces the three values that keep a seller focused on other people, make honest uncertainty acceptable, and turn follow-up questions into stronger discovery.
Read transcript at this moment - 4:20
Create holistic differentiation through genuine interest
Removing ego and using an empathetic tone helps buyers feel heard, while remembering personal context makes the relationship distinctive after the call ends.
Read transcript at this moment - 7:22
Ask what success looks like before following the agenda
A simple opening question reveals the buyer’s desired outcome and gives the seller permission to call an audible when the prepared agenda misses what matters.
Read transcript at this moment - 10:33
Replace role play with deliberate practice
Casey reframes role play as practice and recommends short daily repetitions of strong questions, case studies, and customer scenarios instead of improvising on live buyers.
Read transcript at this moment - 14:30
Turn post-call alignment and recaps into trust
Teams can prevent assumptions by comparing what each person heard, agreeing on responsibilities, and sending a customer recap that confirms attentive listening.
Read transcript at this moment - 17:27
Use specific feedback to find and fix gaps
Numbered feedback prompts produce concrete coaching, and leaders who make failure safe help sellers analyze gaps, build critical thinking, and preserve confidence.
Read transcript at this moment
Transcript
0:02 So Casey, you were talking about the uh
0:03 the three main pillar values of being
0:06 humble, vulnerable, and curious for a
0:08 seller. Uh just tell me a little bit
0:09 more about that.
0:11 >> Yeah. Um these are these are I think
0:14 skills that people forget about. Um we
0:16 we focus so much on AI and and the power
0:19 of technology, which I I'm not to say
0:20 they're not important. They are
0:21 important. M
0:23 >> but what when I when I was going through
0:25 my transition of leaving corporate kind
0:27 of figuring out what's next writing a
0:29 book and then this journey of you
0:31 speaking coaching found me it it really
0:33 what helped me kind of get grounded in
0:34 that was like hey what are the values
0:35 that drive me as a salesperson as a
0:38 leader as a dad
0:40 >> and it came down to humility
0:42 vulnerability and curiosity I think the
0:44 most humble people in the room uh it's
0:46 always about someone else I think uncle
0:48 Rico moment anybody know that's from
0:50 from Napoleon Dynamite whenever I got to
0:52 reference my college football days. I
0:53 got to give love to Uncle Rico.
0:54 >> Yeah.
0:55 >> Uh it was always about my linemen. It
0:56 was always about my teammates, my
0:57 defense, my receivers, my coaches. Like
0:59 sure the quarterback gets all the glory,
1:01 but quarterback can't throw the ball to
1:03 himself. And just like in sales,
1:05 salesperson needs a great product team.
1:06 They need a great recruiting team if
1:07 you're in staffing. They need a great
1:09 leader. They need a great someone's got
1:10 to send those invoices. Someone's got to
1:12 collect the payments. Like
1:14 >> even like there was times I would call
1:16 my help desk sometimes
1:18 just to say, "Hey,
1:20 >> they thought like something's wrong with
1:21 computer. I just want to say, "Hey man,
1:22 this guy's name is Eric. I said, "Eric,
1:23 I want to let you know my computer's
1:24 running great today." He's like, "Wait,
1:26 what?"
1:27 >> You know, just to just to kind of create
1:28 these different moments or uncommon
1:30 moments. Um, so I think humility is such
1:31 a power and and humility knowing that
1:34 when you're building relationships with
1:35 a customer, they don't care how much you
1:36 know. They care how much they don't care
1:38 what you know, but they care how much
1:38 you care.
1:40 >> I think curiosity is again, I'd say a
1:43 superpower that many sales people just
1:45 forget to do. They think so much about I
1:46 got to tell this client everything about
1:47 what we do. I got to tell them about the
1:49 product or offering. they might not care
1:51 yet salespeople. So,
1:53 >> if you're going to tell a story, if
1:54 you're going to ask questions or try to
1:56 like convince somebody something, ask
1:58 them if they're even interested in
1:59 hearing a story how you've helped
2:01 another customer and then they're ready
2:02 to listen. But I think curiosity is a
2:06 gap of most sellers, they ask one
2:08 question, they forget to ask the
2:10 follow-up question such as, "Tell me
2:12 more about that. Describe why that would
2:13 be important to you.
2:14 >> Explain what would happen if you didn't
2:16 achieve that goal."
2:17 >> You're getting really good at discovery.
2:18 And I think that's something I learned
2:20 at I think I got really started focusing
2:22 hard on at age 41. I was always I would
2:25 think uh unconsciously competently
2:27 curious, but now I'm consciously
2:29 competently curious and something I work
2:30 on all the time.
2:32 >> And I think vulnerability
2:35 uh one of my favorite leadership mantras
2:36 that I got taught from one of my
2:37 mentors, a guy named John Kaplan, he
2:38 said, "It's okay not to know everything,
2:40 but not okay not to do anything about
2:42 it." And so I think it's it can be
2:45 refreshing for a buyer sometimes when
2:46 you say, "Hey, you know, I'm not quite
2:48 sure about that. Let me let me do some
2:50 quick let me do a quick double check.
2:52 I'll get back to you within an hour."
2:53 You kind of set yourself up a chance to
2:54 like set expectations, set some
2:56 follow-up, but I've yet to meet the
2:58 perfect person, Austin. I've yet to meet
3:00 the perfect the person that knows
3:01 everything about every single thing in
3:02 life. And so I think just embrace
3:05 vulnerability because like as Bnee Brown
3:07 teaches us, it's it is the, you know, it
3:09 just is the key to connection and it
3:11 just humanizes us as humans and I think
3:13 it allows for relationships to form a
3:15 little bit more authentically.
3:17 >> Yeah. I mean like hearing this, I'm I'm
3:20 hearing like the uh all those like top
3:23 level like recommendations for a
3:24 saleserson as they're going through a
3:25 training like listen twice as much as
3:27 you speak. You got two ears, one mouth.
3:29 So, do that
3:30 >> or like be curious or like sorry, not be
3:32 curious but like we'll use open-ended
3:35 questions and like and it's very like
3:36 technical. It's very much like here are
3:39 the the tactical things that you need to
3:41 do and I don't often hear like the
3:44 underlying more emotional aspect or more
3:47 like foundational bedrock aspect of it
3:49 but it's like okay but you know being
3:52 humble being curious that's a more deep
3:55 version of saying like listen twice as
3:57 much as you talk. Um, have you noticed
4:00 that like as you focus on those things
4:02 or you've trained from that direction or
4:04 that underlying thing that you're seeing
4:07 a more impactful like set of actions?
4:10 Like somebody's actually saying tell me
4:12 more from a actually more interesting
4:14 like perspective because they're
4:16 thinking of it from being those three
4:18 those three things at all times.
4:20 >> 100%. I think it the biggest thing it
4:22 does Austin it removes your ego.
4:24 >> Yeah. And it keeps that thing checked
4:26 because we all got one. And uh in life I
4:29 don't want to be right. I want to get
4:30 what I want,
4:31 >> you know, which is my time. I want to
4:33 help someone else have a good a better
4:34 outcome. And
4:36 >> I think one thing that when you're
4:38 curious, your tone has to be
4:41 >> thoughtful. So I just say if I just say,
4:43 "Hey, tell me more about that." Well,
4:44 that was kind of firm and direct. I say,
4:46 "Wow, tell me more about that."
4:47 >> There's empathy in my voice. There's
4:49 tone a tone change. And if you're if you
4:53 genuinely want to be interested versus
4:55 interesting, I think more often than
4:57 not, you're going to find more people
4:58 would like to talk to you because you're
5:00 genuine and you're authentic versus and
5:02 when you do those things, I found in the
5:04 ripold age of 50. Now, you you can
5:07 create a type of differentiation that I
5:09 got taught called holistic
5:10 differentiation, which is how you make
5:12 people feel when you leave the call with
5:13 them.
5:14 >> Yeah.
5:14 >> Are are are you on your mind? are are
5:16 you on their mind in two hours from now
5:18 because of man that that Austin guy, he
5:20 asked great questions. I can't believe
5:21 he remembered to talk to me about that
5:23 and how do you remember my daughter is
5:25 going off to college uh orientation and
5:28 when you lead with that curiosity
5:29 because you documented you remembered
5:31 things about someone.
5:32 >> Mhm.
5:32 >> You don't need AI. You don't need AI for
5:35 that.
5:35 >> You don't need a faster computer for
5:37 that. You just need to be like and which
5:40 I think goes back to that HVC mindset
5:42 which I've like kind of tagged it. I
5:43 call it my HVC flywheel which when those
5:46 three things get going it just creates I
5:48 get goosebumps talking about it. It just
5:50 creates
5:51 >> momentum.
5:53 >> Yeah. I mean like you know AI noteaker
5:55 can get on the call but it can't
5:57 experience the emotions that the two
5:59 people or the three people that are you
6:01 know however many people are having as
6:02 they're going through it or like it
6:04 can't read. I mean like an easy one is
6:06 like the sarcasm, but it doesn't know
6:08 what you guys are truly forming those
6:11 deeper connections on. You feel it and
6:13 then you can see in the other person's
6:14 face that they're feeling it
6:16 >> and by having like the more emotional
6:18 approach to it or the more emotionally
6:20 intelligent approach to it, maybe not
6:22 emotional, just simply that seems like
6:24 it really creates that deeper
6:26 connection. I can already imagine like,
6:28 you know, sure I have I sit down, I do
6:30 my pre-call plan, I know what questions
6:32 I'm going to ask. Um, but I'm not gonna
6:36 but if I just stay rigid and I'm not
6:38 actually curious. I'm just like, well,
6:39 this is what I have to do. I got to
6:40 check these boxes. You're not gonna ask
6:42 the right questions at the moment. You
6:44 might luck out, but you're going to be
6:46 missing out the true curiosity, the true
6:48 where you are actually connecting the
6:50 true underlying, you know, conversation
6:53 that's happening that's not just
6:54 happening with the words that are being
6:56 said back and forth. Um, that's just
6:59 Yeah, go for it.
7:00 >> Yeah. Well, I was going to say you made
7:01 me think of so maybe a a great I mean a
7:04 hopefully this is a great thing for
7:05 because I I it really impacted me when I
7:07 learned this question is
7:09 >> so you imagine if a seller they we're
7:11 obviously taught pre-all plan get your
7:12 agenda together have all your questions
7:14 >> but we're so focused on that sometimes
7:16 we forget to be curious
7:18 >> so the question I teach that I got
7:20 taught that I that I found it to be very
7:22 very impactful. So, if I was meeting you
7:23 for the first time and I was getting
7:25 ready to sell you, you know, coffee cup,
7:27 I could say before I go into all that,
7:28 I'd say, "Hey, Austin. Hey, thanks for
7:30 making time to meet with me today. Hey,
7:31 before we get started, describe what
7:33 would make today a successful outcome
7:34 for you in the 30 minutes we have
7:36 today."
7:36 >> Mhm.
7:37 >> And let's say, for example, that the
7:39 things on my agenda don't match what you
7:41 want to talk about.
7:42 >> Yeah.
7:43 >> It gives me a chance as a quarterback
7:45 here, Uncle Rico moment again, to call
7:47 an audible line of scrimmage. I'm like,
7:48 "Oh, shoot. I wasn't ready to talk about
7:50 that." But I can still lean into my
7:52 curiosity and I could say,"Great,
7:53 Austin, tell me why that would be
7:54 impactful for us to talk about that."
7:57 >> And then maybe you going, "Well, because
7:58 Casey, I got this big initiative coming
8:00 up and it's going to impact this, this,
8:01 and this." Oh, wow. That sounds
8:03 exciting. Tell me who else that's going
8:04 to impact.
8:05 >> It just allows me to keep going, "Tell
8:06 me more. Tell me more." Because I'm
8:08 interested in what you want to talk
8:09 about. And I think buyers,
8:12 at least for me, like when I'm going
8:14 when I'm buying something, I'm already a
8:15 little bit I got my defense mechanisms
8:17 up because I'm feeling like is this dude
8:18 or this girl gonna try to like versus if
8:20 someone's genuinely curious at me, I'm
8:22 like I I I open up because I'm I know
8:25 they're there to help me and they're
8:26 going to guide me through a buyer's
8:27 journey versus trying to, you know,
8:30 force things into me I don't need.
8:32 >> Yeah. I mean, if you're not being
8:34 humble, you're not going to throw out
8:36 your agenda that you had pre-planned,
8:38 which is silly, right? They're giving
8:40 you the exact answers to the test at the
8:43 very beginning and saying, "Here's all
8:44 you got to answer for me. Here's what I
8:46 want from you." And if you go, "Uh, this
8:48 person doesn't know what I'm talking
8:49 about." Because you lack that you lack
8:51 the humility for it. All of a sudden,
8:53 you're throwing away the perfect
8:54 opportunity
8:55 because you're not willing to do HBC in
8:58 order to get moving forward.
8:59 >> Yeah. And maybe I might say this, again,
9:01 this might be uncommon to say, but maybe
9:03 I I'll say this where you could use a
9:04 vulnerability, too. I might say, "Yeah."
9:06 >> Wow, Austin. I'm I'm glad you said that.
9:08 Um, in all honesty, that was not on my
9:10 agenda, but I'm glad you brought it up
9:12 because now I'm excited to talk to you
9:13 about that.
9:14 >> Yeah,
9:15 >> that might be again, you're just show
9:16 you're just showing that we're not these
9:18 perfect people. And and you know,
9:22 sometimes there's c maybe one out of 10
9:24 buyers might not buy into this. I say,
9:26 who cares? You you can't win. You can't
9:29 win everybody.
9:30 >> But over time, when I do those when I
9:32 focus on those values and let those
9:33 values drive me, I'm a better version of
9:35 myself. I create better environments of
9:37 people around me. And um it just allows
9:40 me to again win my time. Either me
9:42 focusing on the right things at the
9:44 right time, write deals at the right
9:45 time, or helping the customer focus on
9:46 the right things at the right time that
9:48 they want to focus on.
9:49 >> Yeah. So, I mean, I think, you know, I
9:52 think it's fair to say that like, you
9:53 know, as you're learning these like this
9:55 new approach, this new idea concept,
9:58 you're going to have to give yourself
9:59 grace and it's going to take, you know,
10:00 time. You're not going to just, oh,
10:02 okay, cool. I listen to a podcast and
10:03 now I'm going to do it.
10:04 >> I'm an expert.
10:06 >> It's already there. It's already there.
10:07 So, for the person who's looking at this
10:08 and going, "Hey, you know what?" I was
10:10 just kind of like, "Here's my pre-all
10:12 plan." I wasn't really thinking about
10:13 being humble. I was curious, but I was
10:16 really just curious because I was told,
10:17 "Here are the questions I should be
10:19 asking everybody." Um, how do you what
10:21 recommendations or guidelines do you
10:22 have for somebody who's going, I all
10:24 right, I want to adopt this approach.
10:26 I'm not going to do it perfectly next
10:28 time. How do I start building this into
10:31 how I actually approach each of these
10:32 calls? So, I'm going to say two words
10:34 that are going to make every salesperson
10:35 get freakout mode. Role play. But I
10:38 don't call it role play, everybody. And
10:40 I I ask every sales leader, get rid of
10:42 the get rid of the phrase role play
10:44 >> in your in your vernacular because I
10:46 when I I played sports, I've never heard
10:49 of a coach, any sport, let's say we have
10:51 a game on Saturday, they're going to be
10:53 they're never going to say, "All right,
10:54 guys, two to all right guys or girls 2
10:55 to 4." Every day we got role play.
10:58 >> Yeah.
10:59 >> They say we have practice from 2 to 4.
11:01 Yet people in business and sales, we
11:03 just don't think we have to practice
11:04 because now we're adults and we're these
11:06 experts and we can just wing it.
11:08 >> But imagine if we told our customers,
11:09 "Hey, nice to meet you, Austin. I'm
11:11 going to wing it today and practice on
11:12 you. Are you okay with that?"
11:14 >> And they'd probably say, "No, get the
11:15 hell out of here." So, I mean, being
11:17 sarcastic, but the point is I love the
11:19 love that you said grace. That's
11:20 something I say a lot to the clients I
11:22 work with is give yourself grace. And we
11:26 all each person in the world gets,440
11:30 minutes a day. No one gets more. No one
11:31 gets any more. No one gets less. So if
11:34 there's something that triggered you
11:35 like, "Wow, I I'd like to get better at
11:36 that." Perfect. Even if you practiced
11:40 five minutes a day asking that intro
11:42 question. You practice asking what I
11:44 what I got taught, which now I teach
11:46 called TED based questions. Tell me,
11:47 explain, describe.
11:49 >> Practice asking a TED based question
11:51 that aligns with a problem that you
11:53 solve for your customer. Practice
11:55 learning a case study that your maybe a
11:59 more seasoned professional in your
12:00 company did. Hey, tell me how you did
12:02 that. Tell me what was the problem. What
12:03 question did you ask? Take notes. Start
12:06 creating the these things that you can
12:08 then put into practice. And maybe you do
12:10 it off hour, salespeople.
12:12 >> Yeah.
12:12 >> Again, when we were in high school and
12:14 college, you had homework. Sometimes
12:16 there's homework in the job. Um I'm
12:18 going to date myself here, but I
12:20 remember um remember the Sunday
12:22 classifides?
12:24 Yeah,
12:24 >> I mean I'm dating myself now. These are
12:26 and for people have no idea what I'm
12:27 talking about. So a Sunday morning paper
12:29 was a thick thing and before the really
12:32 the internet they would put like job
12:33 descriptions and job postings and so I
12:36 was in staffing and consulting for 20
12:37 years. That's where I started learning
12:39 about the companies out there. I would
12:40 literally go through on a Sunday, learn
12:42 about all these companies and I would
12:44 practice, hey, what questions would I
12:45 want to ask that might make them be
12:46 interested to talk to me or what that
12:49 looks like this this posting's been o
12:51 open for now three Sundays in a row.
12:52 Well, they're obviously having a
12:53 challenge. Maybe lead with, hey, tell me
12:55 what's what what challenges are you
12:57 having? Tell me why this can this
12:58 posting's been open there. But again,
13:00 practice is a lost art in sales. Um, and
13:04 usually it's because they're lacking
13:06 humility, vulnerability, curiosity, and
13:08 their egos up and they they want to just
13:09 puff their chest out and be perfect. But
13:11 I hope when there's a top performer
13:13 listening to this because I think that's
13:16 I think as I reflect back on my career,
13:18 one thing that helped me is so I was top
13:20 rep at our company for 10 10 years
13:21 straight nationally. I still practice. I
13:24 still was not afraid to say I don't
13:25 know. I still looked for other people.
13:26 Hey, can you proof this email real
13:27 quick? And when you have that mindset of
13:30 you've never arrived. You might have
13:31 been really really elite or great today,
13:33 but doesn't mean you're guaranteed to do
13:35 that tomorrow. So keep practicing these
13:38 skills. And to your thing, Sarah, give
13:40 yourself grace cuz you'll you won't
13:42 regret it.
13:43 >> It's so weird that we expect children to
13:46 have a growth mindset and then at some
13:47 age we're supposed to flip into a
13:50 non-growth mindset. And it's like, why?
13:52 The the time when I was achieving the
13:54 most and, you know, do growing the most
13:57 was the time where I was supposed to
13:58 believe that I had like things to learn
14:00 and was, you know, expected to be wrong
14:03 on occasion. And then we're like, "Oh,
14:04 now you turned 18, you have your first
14:06 job. turn that switch off even though
14:08 it's like wait a second all of my
14:10 progress came prior to turning that
14:11 switch off. This doesn't make any sense
14:13 to switch over to this other like
14:15 mindset. Um you know you you mentioned
14:18 to like the practice and all that stuff.
14:20 Uh what about you get done with a call
14:22 like are you doing like a post call
14:24 debrief where you're kind of sitting
14:25 there? Yeah. What does that look like uh
14:27 as you're trying to adopt this HBC?
14:30 >> Yeah. So it's interesting you say so
14:31 like a page I I've actually memorized
14:33 it's like page 83 84 in my book where I
14:35 I talk about when there's sellers say
14:37 you have multiple people on your team
14:38 and you're you have a cross functional
14:40 sale so it's a complex sale a lot of
14:42 times people will leave a meeting and
14:44 then they assume that well we're all
14:46 thinking the same we all we're all mind
14:48 readers and this is where I think people
14:50 need to slow down and say there's
14:51 expectations of what we're going to do
14:53 but do we have an agreement of what
14:54 we're all going to do so imagine if we
14:56 took 3 to 5 minutes hey man good call me
14:58 what's one or two things you guys heard
15:00 Okay. What you hear? Okay. I heard the
15:01 same thing. Perfect. We're on the same
15:02 page.
15:03 >> My expectation. This is what I'm going
15:04 to do. What are you guys going to do?
15:06 Okay. Boom. Are we all in agreement,
15:07 we're on the same page. It's like again
15:09 when you're calling a play in the
15:10 huddle, you you call a play in the
15:11 huddle. You break. Now we know what
15:12 we're going to do at the line of
15:13 scrimmage.
15:14 >> Yeah.
15:15 >> Then I love sending recaps to my
15:18 clients, letting them know, hey, I'm
15:20 going to send this recap to you. Many of
15:21 my customers tell a story. Many of my
15:23 customers find this valuable because I'm
15:24 going to show you that we we listen. We
15:26 understand what's important to you. If
15:27 you could please send me a note back,
15:28 Mr. Mrs. customer, let me know if I've
15:30 if I've captured everything correctly.
15:31 If I've missed anything, please let me
15:33 know.
15:33 >> Yeah.
15:34 >> A lot of times when I do that, they keep
15:35 selling themselves. Oh, you know what? I
15:37 forgot to mention this. Or you know
15:38 what? This looks great, Casey. Thanks so
15:39 much for doing it.
15:40 >> Yeah.
15:41 >> But too often we go from call to call to
15:43 call to call to call and maybe we forget
15:46 to document some of those things and now
15:47 you become like every other seller that
15:49 frustrates a buyer because they didn't
15:50 listen, you don't understand my
15:52 business, you didn't follow up. Again,
15:54 all these things you don't need AI for.
15:56 Sure, AI can help you do these things.
15:59 maybe more efficiently,
16:01 >> but you still got to put in the work.
16:02 And so I love that you called that out
16:05 because um too often we we don't slow
16:10 down to do that. We get going way too
16:12 fast and then when you get going way too
16:13 fast, this little big or longer word
16:15 called complacency
16:17 >> sneak sneaks in and then bad habits
16:19 start being formed.
16:20 >> Yeah. Um what about like directly to
16:24 like analyzing your own your own
16:27 humility, your own vulnerability, your
16:29 own like because one of the things that
16:30 I learned uh during you know schooling
16:34 uh was um like through like emotional
16:36 intelligence papers they would just be
16:38 like look you get done with the
16:39 situation then you just sit down and you
16:40 like what were my emotions what were
16:42 their emotions what why did those
16:44 emotions come up why did their emotions
16:46 come up maybe we had a conflict what
16:49 what's like the and like just sitting
16:50 there really thinking about it. I'd be
16:52 curious like if you have any like
16:53 recommendations like like just like
16:55 getting done with a call and just being
16:56 like all right did my ego show up? Did
16:59 was I did my did a lack of humility stop
17:02 me from you know being able to switch my
17:04 agenda and then be able to step like you
17:06 know what they said this and I totally
17:08 ignored it because I was not humble
17:10 enough or
17:11 >> hey you know I had a moment of curiosity
17:13 but I didn't follow it because xyz and
17:16 then just really analyzing those three
17:18 aspects. Um, I'm not sure like you're
17:21 the expert on this thing. I just start
17:23 making you think of like the training on
17:25 the emotional intelligence from the
17:26 past.
17:27 >> Yep. Love that. Great question, man. I
17:28 think the most simplistic way is when
17:30 you leave a call, look for gaps and
17:33 don't let the gaps like crush you. Look
17:35 for the gaps like, "Oh my god, sweet.
17:37 Yes, I found the gap. Now I can go fix
17:39 it."
17:39 >> And so when I look for feedback, I like
17:42 putting um numbers in the question.
17:45 >> Mhm.
17:46 >> Which gets more specific answers. So,
17:48 let's say that you're my boss and I'm
17:49 like, "Hey, Austin, I think that call
17:50 went well. Tell me two things you
17:52 thought I did well and two things I
17:53 could have done differently or better."
17:54 >> Nice. Yeah.
17:56 >> And then whatever you say, I might then
17:57 it gives me a chance to be more curious.
17:58 Great. Tell me tell me why or tell me if
18:01 I did if I shoot I didn't ask that
18:03 question, but if I asked that question,
18:04 tell me how it would have impacted the
18:06 the conversation better so I can learn
18:08 from that.
18:09 >> Yeah.
18:10 >> Because I think when when the feed when
18:12 it's too loose like, "Hey, how's your
18:13 day going?" Great. Well, if I but versus
18:15 I said, "Hey, tell me two things that
18:16 make made you smile today."
18:18 >> Yeah.
18:18 >> Totally different outcome.
18:21 >> Makes you really think about it, right?
18:22 It's it's forcing function of actually
18:25 having thought and intent put into what
18:27 that is going to look like. Um, so from
18:30 like a sales leader perspective,
18:32 >> uh, so you're making me think of, so
18:35 we're both athletes, we both played a
18:37 bunch, so like I think our brains just
18:38 default back to those settings.
18:40 >> Yeah. Um, what I when I used to coach, I
18:43 would sit down at halftime with my team
18:45 and we'd actually start every halftime
18:46 with what do you guys think went well?
18:49 What do you guys think, you know, went
18:52 poorly or what was your opportunity to
18:54 improve? Uh, we got we got to have such
18:56 a level of comfortability like what went
18:57 bad? And they were like, yeah, they
18:58 didn't put up their shields cuz we
19:00 weren't going to yell at them about what
19:01 went bad. And then we' be like, okay,
19:03 what adjustments do you want to make?
19:05 And then we would switch it over and we
19:07 go, hey, you guys nailed it. This, this,
19:08 and this. here's something that we think
19:10 you also should be taking in
19:11 consideration for the second half. And
19:13 it was cool because at the beginning of
19:15 anytime we take on a new team, the first
19:18 couple games, they would be struggling
19:20 with, you know, how do I answer these
19:22 questions,
19:23 >> but then over the course of the season,
19:25 we get them for multiple seasons. The
19:27 course of the first season, they'd start
19:28 owning the halftime conversations. And
19:31 then by like the second or third season,
19:33 like they would be just talking to each
19:34 other and having like a really
19:36 productive conversation. And we would we
19:38 would offload most of it and then we'
19:39 just be listening in and then like
19:41 emphasizing like hey like that point
19:43 like coach's perspective like that's the
19:45 big one like really change this thing
19:47 like they're beating you on the left
19:49 side you guys aren't recovering you have
19:50 to make sure you're getting back on
19:51 defense first or like whatever that you
19:53 know conversation was. Um and so it just
19:56 seems like as a sales leader the thing
19:58 you could do too is flip it on to them
19:59 and say hey what do you like get done
20:02 with a call with them and then be like
20:03 hey what do you think could have been
20:04 the things to improve and then
20:07 Spot on, man. What you're doing is
20:08 you're developing critical thinking
20:10 skills for your sellers.
20:11 >> Yeah.
20:12 >> And as a sales leader, your job is not
20:14 to be the loudest in the room or the
20:15 smartest in the room. Your job is to
20:16 create the loudest room or create the
20:18 smartest room. And if you're the one
20:19 always talking, you're going to let let
20:22 this four-letter word called fear sneak
20:24 in.
20:26 >> And when fear when fear likes to sneak
20:28 in,
20:29 >> uh, now we we're not critical thinking.
20:31 Now our ego is up. Now we're now we're
20:32 losing confidence. And I think sales
20:34 leaders or any leader, remove fear,
20:36 instill confidence. That's that's your
20:38 number one job. And so when you can
20:40 create space through humility,
20:41 vulnerability, and curiosity where your
20:43 sellers or your soccer players or
20:44 whoever it is is not afraid to say,
20:46 "Man, God, I sucked at that thing. Why
20:48 did I let that happen?" Or, "Man, how
20:50 did I forget to document thing?" Or, "Oh
20:51 my god, I've been practicing this
20:52 question all along." And instead of
20:54 torching them, say, "Hey, you know what,
20:56 man? Give yourself grace. At least you
20:58 at least you picked it up. Now, just
21:00 let's just don't let one bad call lead
21:02 to two bad calls
21:04 >> or or one bad day lead to two bad days.
21:06 >> Like, you hired these people for a
21:08 reason. Remind remember why you hired
21:10 them. Keep them confident. Not like the,
21:14 you know, your Iron Fist. You're
21:15 standing on your pedestal and you're
21:16 just like constantly making people that,
21:19 you know, just play tense. I want my I
21:21 want my players playing loose. And I
21:23 think about like,
21:24 >> yeah,
21:24 >> this is like old school Joe Montana. Um,
21:28 there's a there's a clip back from like
21:30 the 1980 something Super Bowl where he's
21:32 it's like they're getting ready for that
21:34 final two-minute drive and that they're
21:36 in the huddle. He goes, "Hey guys, look,
21:38 is that is that John Candy in the front
21:40 row over there?" I mean, everyone's
21:42 like, "What? What? Dude, we're about to
21:43 freaking we have a minute 43 left. We
21:45 got to go score a touchdown." And Joe
21:46 Montana's talking about John Candy in
21:48 the front row. So, again,
21:51 >> keep your teams loose and watch how much
21:54 more they're going to be more
21:55 successful. And then then they're to
21:57 your point helping them create these
21:58 critical thinking skills so they can go
22:00 out and you're not so anxious as a
22:02 leader cuz it's like they're not trained
22:04 not to do to what to say what to do
22:06 because you've created the environment
22:07 for that fear to sneak in.
22:09 >> Yeah. I mean, we've been talking a lot
22:10 from like the rep's perspective on
22:12 having, you know, all of this, you know,
22:14 from a sales leader's perspective, is it
22:16 as is it as simple as just demonstrating
22:18 it or are there nuances that if a sales
22:20 leader is listening in, they should be
22:22 thinking about these nuances separate
22:24 from what we've talked about from the
22:25 rep's perspective?
22:26 >> One of my favorite I think you're asking
22:28 good questions, brother. One of my
22:30 favorite things I love leaders to do is,
22:32 and it's so that most people I've worked
22:34 with so far, I'm sure there's someone
22:36 out there that does this really, really
22:37 well, but I'll ask a leader, I go, "Tell
22:39 me, have you tell me the last time in
22:42 front of your entire team you've told
22:43 your team where you were scared in the
22:45 job or when you failed or when you
22:48 sucked or when you had a brutal call and
22:51 sometimes like they'll say, "Why? Why
22:53 would I do that?" I go, "Why wouldn't
22:54 you do that?"
22:55 >> And I get a blank stare. I go, if you if
22:57 you can show that you once sucked at
22:59 this job, you're going to create the
23:01 space of, okay,
23:03 >> then your team will give themsel that
23:04 much more grace because they realize the
23:06 perfect doesn't exist.
23:08 >> And when we get these jobs or first
23:10 jobs, we're so scared to mess up because
23:12 it's like, oh god, if I
23:13 >> if I get hung up on or they don't get
23:15 that deal closed, they're going to
23:16 can me. Sorry, sbomb on that one. Um,
23:19 edit it out.
23:22 But um but yeah, I think that that's
23:25 that's a perfect example I think for me
23:27 at least that I've seen in my life so
23:28 far where and I even when the world of
23:30 coaching I do now I often I I like to
23:32 lead with my own failures so I disarm
23:35 people so they're willing to share
23:36 theirs
23:37 >> which is again that's power of
23:38 vulnerability.
23:39 >> Yeah. I mean you know failure is the
23:41 greatest teacher. Success is not the
23:43 greatest teacher. I mean, we're all
23:44 driving to success, but failure is where
23:45 you learn. And if you're going to come
23:47 in and not and you want a team to change
23:50 and you're not going to create an
23:51 environment where failure is okay, like
23:54 then what how is change going to happen?
23:56 It's not going to happen because people
23:57 are just going to run to success.
23:59 They're going to hide their failures.
24:00 There's going to be no learning
24:01 opportunity. There's no opportunity to
24:03 change then if you don't have that
24:05 introduce.
24:06 >> Yeah. When I would real quick, when I
24:07 would watch film in college with my
24:09 coach, shout out to coach Bo Baldwin if
24:10 you're listening. It's probably not, but
24:11 if he is, uh, let's say I have a great
24:14 game, 27 to 38, 340 yards, four
24:16 touchdowns, one pick, let's say, and one
24:19 interception. The 27 to 38 that those
24:22 incompletions I had, we would watch
24:24 those negative plays, the plays that
24:26 weren't successful five, six, seven,
24:28 eight times. The plays where I was
24:30 successful, we'd watch it once or twice
24:31 and be like, "Hey, great read, great
24:32 throw. All right, next." I'm like, "But
24:34 that was kind of fun to watch, coach.
24:35 Can we just
24:36 >> Yeah, let me feel good about it."
24:38 >> Right. And it wasn't to beat us up. was
24:40 like they were learning moments and it
24:42 wasn't like embarrassing but it was like
24:43 co getting coached and when you can
24:46 embrace a mindset of you don't know
24:48 everything and that's okay and when you
24:50 find your gaps
24:52 be excited about it because now you can
24:54 go fix them.
24:55 >> Yeah, man. We could keep talking for
24:57 forever about this and I have like a ton
24:59 more questions but I want to respect
25:00 your schedule.
25:02 >> I got two Yeah, we should definitely do
25:04 this again. I would love to get circle
25:06 back to it but I got two requests from
25:07 you.
25:08 >> Yeah. Um the first one would be or take
25:11 them in whatever order you want. One of
25:13 them is the one big takeaway somebody
25:15 should if they're listening in uh should
25:18 you know make sure that they apply like
25:20 if they can only take one thing from
25:21 this what would that big thing be? And
25:23 the other thing would be if they want to
25:24 learn more about you know what you're
25:26 saying how can people find out more like
25:28 from a book from your podcast from how
25:30 do they find out more about uh humility
25:33 vulnerability and curiosity?
25:34 >> I think if there's one thing in the 28
25:36 minutes we've been talking
25:39 uh whether you're a sales leader or a
25:40 salesperson.
25:43 >> Hey, great to meet you today. Before we
25:45 get started, tell me what would make
25:46 today a successful outcome for you.
25:48 >> Get the answers to the test before you
25:50 take the test.
25:51 >> It'll make the conversation so much more
25:53 easier because you're not guessing what
25:54 they want to talk about.
25:56 >> Um if people want to learn more about
25:58 me, I'm super active on LinkedIn. I love
26:00 connecting. I love serving others. I
26:01 love connecting people.
26:03 >> Um then I do this all the time. I call
26:06 it a boomerang mindset. And the key to
26:07 having a good boomerang mindset is you
26:09 don't keep score. Um I don't expect
26:11 things in return. I love serving because
26:13 I know karma is legit and it finds me.
26:15 It found me twice this morning already.
26:17 Um my website is kcyjox.com.
26:21 Um I wrote a book called win the
26:22 relationship not the deal is really kind
26:25 of the journey of how I when I was
26:27 successful in business and sales. How
26:28 did I do it? And it was about bringing
26:30 energy, setting expectations, listening,
26:32 documenting, checking my ego, practicing
26:34 often, having patience. Um, and then as
26:37 you mentioned in the podcast, I'm in
26:38 season seven of the quarterback Dadcast.
26:40 >> I interview dads to talk about humility,
26:43 vulnerability, and curiosity so we can
26:45 be better dads at home, better leaders.
26:48 And so that those episodes come out
26:49 every Thursday morning on um uh Spotify
26:52 or Apple, wherever you can find your
26:54 podcasts.
26:54 >> All right, Casey, I really appreciate
26:56 it. I'm gonna try I I think I failed at
26:58 getting you out of here on time, but
26:59 >> it's okay. I already set
27:01 >> I actually set expectations. Shout out
27:02 to Chris Copel if you listen. I told him
27:04 I'm going to be a minute or two late, so
27:05 I've he already knows. But this has been
27:07 awesome, man.
Questions answered in this episode
How do humility, vulnerability, and curiosity improve sales conversations?
Humility keeps the conversation centered on the buyer, curiosity produces useful follow-up questions, and vulnerability makes it acceptable to admit when an answer needs confirmation. Together, those values reduce ego, improve listening, and help the seller create a more genuine connection than a rigid script can provide.
What should a seller ask at the beginning of a customer meeting?
Ask the buyer to describe what would make the available time a successful outcome. The answer reveals what the buyer actually wants to discuss and lets the seller adjust the agenda before presenting something irrelevant. Follow with tell, explain, and describe questions to understand why the outcome matters and who else it affects.
How can sales leaders create better coaching and post-call learning?
Make practice a normal part of the job, use specific feedback prompts such as two strengths and two improvements, and invite sellers to evaluate their own calls before prescribing an answer. Leaders should also share their own failures so the team can surface gaps without fear, learn from mistakes, and build the critical thinking needed to handle future conversations independently.
