---
title: "You Can't Get Promoted Until You Replace Yourself"
episode: 117
podcast: "The LeanScale Podcast"
publisher: "LeanScale"
guest: "Cole Gillespie"
guest_title: "Chief Revenue Officer, Branch"
date_published: 2026-09-14
date_modified: 2026-09-21
duration: 01:13:28
word_count: 12849
topics: ["sales-leadership", "sales-enablement", "sales-compensation", "gtm-strategy"]
canonical_url: https://www.leanscale.team/knowledge/podcast/cole-gillespie-branch-replace-yourself-on-paper/
source: "LeanScale Knowledge Hub — https://www.leanscale.team/knowledge"
license: "Free to quote and cite with attribution to The LeanScale Podcast."
---

# You Can't Get Promoted Until You Replace Yourself — Full Transcript

> Episode 117 of The LeanScale Podcast, with Cole Gillespie.
> Published September 14, 2026 · 01:13:28 · 12849 words.
> Machine-transcribed and **not diarized** — speaker attribution is inferred, so verify
> attribution against the audio before quoting a specific person.
> Structured breakdown: https://www.leanscale.team/knowledge/podcast/cole-gillespie-branch-replace-yourself-on-paper/

## 00:00 — Cold open + intro

**[0:00]** "My thing I will have to say is just be careful. People are going to roll balls to your feet. Just be careful which ones you pick up."

**[0:06]** Cole Gillespie is the Chief Revenue Officer at Branch and he is one of the

**[0:11]** few revenue leaders who will tell you flatly that sales is a teachable craft,

**[0:15]** then get a little heated defending it. He started out selling commercial loans to

**[0:20]** dentists, which he is the first to admit he knew nothing about, got shipped to

**[0:25]** Texas to open up a new territory from Xero and was running the entire sales team by

**[0:30]** the age of 27. "Sales is, it's trying to convince somebody to buy something that

**[0:39]** you genuinely think is going to be good for them. They called it a career

**[0:43]** obituary. But if you, if fast to you is two weeks and fast to me is two hours

**[0:51]** then we're, we're in trouble." Yeah if they have to ask it's already too late.

**[0:56]** In this episode Cole walks through the entire arc and the lessons he would hand

**[1:01]** to anyone starting a career today, including his own kids.

## 01:14 — "You can't leave this job until you replace yourself"

**[1:14]** Cole, early on your boss told you he would promote you to run the sales team

**[1:19]** but only after you replaced yourself, what happened when you actually sat down

**[1:25]** and tried to write down what you did? Yeah it was, it was one of the harder

**[1:33]** things I think I had to do. Important context, I was a fairly young person

**[1:39]** right, professionally, kind of earlier in my career, and I had a great boss. The guy

**[1:45]** I worked for at the time was one of the founders and still one of the most

**[1:52]** influential people in my career. So oftentimes I'm still liable to quote him

**[1:58]** to some of the people that were close to me or around me. I'll pull up

**[2:03]** John's name. But I was, and I know I say I was running the sales team, that's true.

**[2:09]** They reported to me I still feel like John was the leader of the sales team

**[2:14]** and was the man. But I was doing like fairly well as a rep managing a market

**[2:22]** and traveling around and carrying a quota and doing all those things. And he

**[2:28]** wanted me to step up and lead the sales group and have those people report to me.

**[2:33]** And the challenge was, listen you can't leave this job until you replace

**[2:39]** yourself. That was the challenge to me. Of course Anthony I was like very eager

**[2:44]** to be promoted. You know what I mean? Like the second he told me I was

**[2:48]** promoted I was like let's go tomorrow, tomorrow couldn't come fast enough. So it

**[2:54]** was an interesting challenge for me though because I think at the time I

**[2:57]** thought, although I tried to be methodical about the process of sales, I

**[3:03]** bet you it's true that I thought, you know, that being charming or outgoing or

**[3:09]** charismatic was really important to the sales process. And so like how could one

## 03:12 — Writing the recipe for a sales rep

**[3:13]** do that? How could one replace their personality? So it forced me to dig into

**[3:19]** the actual tactical like what is it that I do every day? How many phone calls do I

**[3:23]** make? When do I make them? How do I follow up? How do I stay organized? Really the

**[3:31]** funnel and the science behind going through the process. And it was

**[3:33]** interesting to map it all out. And once I started doing it I got really excited

**[3:38]** about almost like writing a recipe to be a sales rep. It was such an important

**[3:45]** document. Like I found it incredibly useful even to onboard future reps

**[3:49]** because I would say I actually have a game plan. If you follow this game plan

**[3:53]** there's some comfort in knowing that, you know, it inject your own personality into

**[3:59]** it and you might find success was like incredibly, incredibly helpful. And so in

**[4:04]** a lot of ways it was helpful for me to put on paper the things that I was doing

**[4:09]** tactically that maybe made me effective. But it was also an incredibly useful

**[4:14]** tool to onboard future sales reps and something I still think about. Like when

**[4:18]** we're when we're onboarding new reps I think about what is our recipe and what

**[4:22]** is the framework that we're gonna put a rep into. Yeah so it was valuable. If you

## 04:27 — How much of sales is process versus personality

**[4:27]** had to put a weight to it because it does feel like there is some component

**[4:32]** of personality, likability, natural, EQ that you may have versus the process.

**[4:39]** What percentage would you say sales is on the process side? If you follow the

**[4:45]** playbook you can be successful versus some skills you need on the personality

**[4:50]** side. Yeah so I think what's important I used to call this, Anthony, I used to

**[4:58]** call this capitulation. So we would we would put a new rep into a market and I

**[5:04]** would say and at the time I was probably fairly strict about it. I was like follow

**[5:09]** this playbook it's going to work. Hopefully I do a better job of being less

**[5:15]** kind of you know rigid about it. But you would see people you would see people

**[5:22]** kind of like obediently go through the tasks. Does this make sense? Like follow

**[5:27]** it as if they were baking a cake and and although there's value in that you

**[5:34]** really want you really want there to be meaning behind the action like just

**[5:38]** following the steps is valuable but if there isn't kind of intent and

**[5:42]** motivation behind the actions it's it's not that useful. And so I would call it

## 05:44 — Capitulation: when a rep stops copying and starts owning

**[5:48]** capitulation which is inevitably three or six months in the rep would say I got

**[5:52]** it. I know how to do this but I'm just gonna be myself and I'm gonna do what

**[5:56]** you told me to do and I'm gonna bring myself to the to the job and you're like

**[5:59]** good now we're getting somewhere. So I said that in the answer to your question

**[6:04]** which is like I think product and process knowledge is it I think it's the

**[6:09]** foundation of a good salesperson and I really really believe that you can teach

**[6:13]** the craft of selling something to people to roughly anybody which I love this is

**[6:20]** a thing I love about selling. But it is hard to deny that people who are

**[6:26]** naturally extroverted people who are naturally sort of high in EQ and maybe

**[6:32]** people who are genuinely curious about other people and good listeners are

**[6:37]** going to make good salespeople. So that is true. I think where I hedge is I don't

**[6:44]** like it all the notion that you have to be necessarily one personality type to

**[6:50]** fit those criteria. Does that make sense? So when I say it doesn't make sense yeah

**[6:55]** yeah so so I sort of resent the idea that salespeople of any kind are sort of

**[7:04]** like one flavor of human in in and to give you an example I've I've worked I

**[7:10]** remember early on in my career working with somebody who I really really like

**[7:14]** liked then and still like today and he was so opposite of my personality right

**[7:21]** and I found him incredibly charming I thought he was incredibly likable I

**[7:26]** thought he was a fascinating person with fascinating interests and he was a great

**[7:31]** salesperson he really was he was fantastic but we share roughly nothing

**[7:37]** in common right and I just think that's a good example of like how these things

**[7:43]** can work out. Was there anyone throughout and maybe this is the person but was

**[7:48]** there anyone throughout your career who you feel most people would have written

**[7:53]** off as not able to cut it in sales that really surprised you by being diligent

**[7:58]** going through the playbook learning the craft and then applying it? Yeah he's he's

**[8:05]** somebody that comes to mind but I but I will tell you like I've been surprised

## 08:08 — The trap of hiring for personality

**[8:13]** 20-30 percent of the time where I meet somebody who I think is this person

**[8:19]** gonna make it in through determination curiosity repetition you know what I

**[8:26]** mean that that it ends up working and I end up being completely wrong it's it's

**[8:32]** a great lesson for hiring because when you're hiring for people if you're

**[8:36]** hiring for a personality you can fall into that trap. I've seen a lot of

**[8:41]** really good personalities that don't close any deals too so I've seen that

**[8:44]** side of the equation as well. This is what I think is so I'll talk to like

**[8:49]** founders a lot and in particular technical founders engineering product

**[8:54]** types and they're looking to hire their first like go-to-market theater or they've

**[8:58]** hired their first couple you know salespeople and I'll say it's hard right

**[9:05]** because salespeople tend to be really charming and really good at sales and an

**[9:09]** interview is kind of them selling themselves it's it's really got a hard

**[9:13]** to vet salespeople if you haven't like lived in that ecosystem and hired a bunch

**[9:18]** of salespeople before so I think like exactly to your point I'm completely

**[9:24]** open-minded to being surprised so I try to stay really disciplined around hiring

**[9:28]** the characteristics of people that I think will make good salespeople and less

**[9:34]** on the this person you know looks a certain way acts a certain way behaves a

**[9:39]** certain way in a room and therefore here she will be really good at sales and I

**[9:45]** think like going into sales I sort of thought I sort of had like an allergic

**[9:51]** reaction to the idea that I was a salesperson early on you know um do you

**[9:57]** ever meet people who go home for Thanksgiving and they say I'm in business

**[10:01]** development they don't say they're in sales you know when asked right like a

**[10:06]** little bit embarrassed by the trade yeah yeah yeah I don't like that but I

**[10:14]** think that's that was maybe me earlier because I thought like sales was about

**[10:19]** manipulating people you know like salespeople had moved

**[10:24]** Anthony you know they were taught techniques on how to manipulate people

**[10:29]** and I didn't like that at all I thought that was like not something I wanted to

**[10:34]** be associated with and then what I think I learned and got really excited about

**[10:38]** later was the idea that sales is it's trying to convince somebody to buy

**[10:46]** something that you genuinely think is going to be good for them right right

**[10:51]** right and that's a lot of fun you know that's I give you can I give you an

**[10:58]** example I share with people yeah I say I think one of the best jobs in the world

**[11:05]** would be if there is a cure to cancer to be the sales rep of the cure to cancer I

**[11:12]** know sometimes that rubs people the wrong way but how exciting would it be

**[11:16]** to like pull the list of everybody who has like let's go the people have the

**[11:20]** most severe they have like they're in terrible prognosis yeah and you have the

**[11:26]** cure for them and you can get them connected and make it happen I mean what

**[11:30]** an amazing job that would be I think you're right but I never admittedly

**[11:37]** never thought of that people have a bad reaction to that they think like

**[11:41]** commercializing the cure to cancer is gross I think it's taking it yeah it's

**[11:45]** taking it that way but I just mean connecting people with problems to a

**[11:47]** product that can solve it yeah I don't get into the pricing mechanics of it I

**[11:54]** kind of leave the metaphor just at the connection piece I'm sure it could be

**[11:58]** taken that far but but I think the point is when you're when you're representing a

**[12:03]** really good product that's solving a real problem sales is fun when you're

**[12:09]** not when you're trying to push a product that isn't really adding a lot of value

**[12:12]** it's a night yeah totally agree totally and this is this is like I think that's

**[12:19]** really good advice for people who are thinking and I'm sure that's obvious

**[12:22]** right people are thinking about am I happy in this job do I want a different

**[12:27]** job in the obvious thing that comes to things that come to mind are like how is

**[12:32]** my title what's my compensation structure right those are kind of how am

**[12:37]** I going to be able to hit quota there's obviously important things but how

**[12:44]** passionate you are about selling the product how how passionate you are about

**[12:49]** genuinely trying to convince somebody to do something you think is going to be

**[12:52]** good for them is an exciting that's an exciting product to try to sell and I

**[13:00]** love spirited debate and I love having those types of conversations with

**[13:07]** people and so if I feel like the product is going to be valuable for you I have a

**[13:15]** fairly insatiable amount of energy to try to convince you to do it and if I

**[13:20]** didn't I think I'd be really bummed that I wouldn't want to do it anymore you

**[13:24]** know to me like I would be I would be a legitimately bad salesperson that's I'm

**[13:29]** sure that's true yeah at your core if you're not believing in what you're

**[13:34]** selling it's very very hard to do and I have been in some companies where I'm

**[13:37]** like the product is okay but it's not getting me super excited and making me

**[13:45]** want to jump out of bed every morning yeah and that's a tough spot to be I'm

**[13:50]** curious if we could go back to your playbook and when you first started to

**[13:56]** codify the things that you were doing what's in there what what's something

**[14:00]** that you follow to this day you've taken that playbook and shared with sales

**[14:05]** people what are those core things that every salesperson should be following

**[14:09]** yeah so there were now keep in mind this was like I'm gonna date myself but this

**[14:15]** was like pre Salesforce you know I mean so was it like you were just gonna be

**[14:20]** like download my funnel metrics and here's what my conversion rights look

**[14:23]** like and all of that right so I had to do some of that stuff by hand I know

**[14:27]** that sounds crazy so what what I think is interesting is there were there were

## 14:33 — The career obituary

**[14:33]** the obvious things that you had to do there were like I make this number of

**[14:37]** phone calls every day I have this number of prospects that I reach out to right I

**[14:41]** go on four appointments a day four days a week I use my Mondays to catch up or

**[14:47]** Fridays to catch up on X Y and Z there's that was really valuable because that

**[14:51]** was activity level stuff that was going to be helpful right but the interesting

**[14:57]** thing and the thing that I think was was a little bit more eye-opening for me

**[15:02]** was there were a lot of like qualitative metrics in there that were really

**[15:07]** helpful to define so I'll give you an example so I would write I remember I

**[15:12]** did this exercise with the team and I called it it's a little bit a little bit

**[15:16]** more bit but hang in there with me which is like I called it a career

**[15:19]** obituary I've brought up the cancer example so I called it career obituary

**[15:30]** and the idea was like when you leave your job what are what will your manager

**[15:35]** say about you what will your peers what will your customers say about you in the

**[15:39]** in the sense that I had the opportunity where I would work with I would travel

**[15:44]** into a market right and I'd go on appointments with a rep and he or she

**[15:48]** would take me around to all of the you know it was very channel driven so he or

**[15:54]** she would take me around to like a lot of the channel partners that they were

**[15:58]** working with who would say glowing things oh I'd love so-and-so and they're

**[16:02]** great I really enjoy working with him or her and then I would leave and then you

**[16:07]** hear a bunch of stuff right guys are they would leave mm-hmm I would come back

**[16:12]** and say so-and-so left we're gonna bring a new rep in they say oh well good

**[16:15]** because this person never followed up they never understood my deals they never

**[16:19]** kept me updated I rarely you get it right I thought that's fascinating

**[16:24]** because I bet the people who left don't know that it totally makes sense yeah

**[16:30]** no I just think any like proactive reflection to kind of put yourself in

**[16:36]** that endpoint and then bring you down to the current point you know sometimes not

**[16:40]** not to get too like philosophical but people do that about their lives like

**[16:43]** hey what is what are people gonna say about you at your funeral type of thing

**[16:46]** so how do I live today like that I think this probably won't create as much

**[16:52]** existential dread for people but keeping them locked into their career knowing

**[16:55]** hey did I do everything that I should have done or I'd want my legacy at this

**[17:02]** company to be I think it's very smart so along those lines you asked me the

**[17:07]** question about the like the formula I would develop like okay well I want my I

**[17:13]** want my channel partners to think I'm responsive to think I you know I'm

**[17:19]** honest in my communication to think that I'm knowledgeable about the product the

**[17:23]** process and the competitors knowledgeable about how to help them in

**[17:26]** their business right wasn't a lot of things it was like a handful of things

**[17:28]** and then I thought what a great gift this is because I can actually

**[17:32]** manufacture that reputation if I do those things right great but here's the

**[17:39]** catch was like inevitably somebody would say well be fast to follow up with me

**[17:46]** right if that makes sense who would argue with that nobody but if you if fast

**[17:53]** to you is two weeks and fast to me is two hours then we're we're in trouble

## 18:00 — Turning "responsive" into a three-hour SLA

**[18:00]** because I think I'm fast and you revise first you think you're fast and I don't

**[18:05]** think you're fast at all right because my my priorities are my idea of fast is

**[18:09]** different so there were these like subjective qualitative things that I

**[18:13]** started to dial in which is like I return customer phone calls in three

**[18:17]** hours I return vendor you know channel partner phone calls same day and so I

**[18:22]** started building like little SLAs into what I did this is like how I replaced

**[18:27]** myself yeah and and then it was helpful to clarify that in communication with

**[18:33]** customers and channel partners which is listen if you reach out to me and you

**[18:37]** don't get me expect to hear back in three hours that's it that that's what

**[18:41]** you should expect okay got it and then when somebody would ask how was cool is

**[18:45]** he responsive they'll say yeah he gets back to me in three hours that's the

**[18:48]** expectation I have any other good enough and I thought that was like early on in

**[18:54]** my career I thought this is this is really helpful for me because I don't

**[18:58]** have to like I can I can manufacture sort of the reputation maybe might be too

**[19:07]** much of a loaded word right but how partners feel about me and customers

**[19:11]** feel about me because I can set a standard and then just behave my way

**[19:15]** into it and and I will say it was helpful where sometimes people feel like

**[19:22]** you're not doing something that you that you feel like you're doing I mean that

**[19:25]** stuff happens all the time but it was right right and so it was helpful to have

**[19:30]** this like agreement with people who worked for me and with me in a similar

**[19:35]** way where they say I don't think you're like you know I don't think you're

**[19:40]** really good at following up with me or you know including me in these things

**[19:44]** are doing XYZ and instead of getting defensive which I would be prone to do

**[19:50]** you know I would say stuff like oh really shoot because I tried that's a

**[19:58]** thing I try really hard to be good at and the way I try to do it is this way

**[20:01]** but it sounds like I didn't do that all that well can you tell me what happened

**[20:06]** well I don't really have an example for you just it feels that way okay well

**[20:11]** understand this is what I'm trying to do and that's the approach I try to take so

**[20:14]** and so now I took something I might overreact to or get defensive into and to

**[20:19]** just curiosity well and I think the specificity of everything to like rather

**[20:29]** than just throwing out words assuming we're all on the same page and it's

**[20:33]** like you're using the same words but speaking a different language yeah so

**[20:37]** having that specificity in the detail behind it to say hey yeah this is a okay

**[20:42]** this is the agreement we had these are the standards that we understand and

**[20:45]** there's not ambiguity baked in it's very clear of what you what you need to do I

**[20:50]** imagine and I know we talked about this a little bit on our prep session for

**[20:54]** this imagine when you're building teams and you're scaling the reputation

**[20:59]** standard that you have with your team that part of the contract is super

**[21:03]** important yes yeah I I can be pretty specific about this like I'll tell roughly

## 21:15 — The four things you should expect off the elevator

**[21:15]** anybody who who works in the revenue or get a team I'm leading that when they

**[21:23]** get off the elevator they should expect at least four things okay one they should

**[21:27]** expect to understand what good or bad performance looks like and they should

**[21:33]** have alignment with their manager okay they should be compensated fairly for

**[21:38]** that I didn't say the best okay I didn't say it's fairly they should be treated

**[21:44]** with respect and they should have the tools necessary to execute on their job

**[21:49]** that's standard everybody gets that and if they don't they need to raise their

**[21:54]** hand right because that's our problem it's something we need to give to them

**[21:57]** and so that's that's the table stakes and the reason why that's important to

**[22:02]** me is like on the on the first one I spent a lot of time early on in my

**[22:08]** career managing the feelings of people who worked in the organization on

**[22:15]** whether they were doing well or not they the feeling that they weren't doing well

**[22:19]** or the inadequacy that they weren't getting enough positive feedback or the

**[22:24]** feeling of misalignment of like I'm almost interpreting my manager's

**[22:29]** response to slack messages or text messages or emails or phone calls and it

**[22:34]** doesn't sound like he or she is like that happy with me I wonder if I'm doing

**[22:38]** a bad job right does any of this sound familiar to you I've I've been in that

**[22:42]** situation on both sides I've been in the situation where I'm wondering am I doing

**[22:46]** what I'm supposed to be doing because I think I am but tones weird you're not

**[22:51]** very specific we're not responsive and then I know I've been in a leadership

**[22:56]** position where I haven't set the standard of what good looks like well

**[22:59]** enough and I know when people come to me asking it's like oh if you have to ask

**[23:05]** then I haven't made this clear enough yeah it's your responsibility right right

**[23:10]** yeah yeah yeah and in I'm particularly I'm particularly trying to solve getting

**[23:17]** getting rid of that percentage of your life that you spend worrying about it and

**[23:22]** getting it focused on the job and so it's interesting to learn how much like

**[23:29]** mental stress and anxiety people can spend trying to interpret whether they're

**[23:35]** doing a good job or not or reaching for the things that they might be thinking

**[23:39]** looks like good performance and one I think it's just a bummer of a way to do

**[23:43]** your job like if you're going into a performance review and you think I hope

**[23:48]** my manager thinks the way I do you're off to a bad start like that's a I would

**[23:55]** feel bad as a manager that that person feels that way and so I want to eliminate

**[23:59]** that I just want I just want everybody to say I think I know what good

**[24:03]** performance looks like in my boss and I are aligned on what that is now I can

**[24:06]** objectively look at my performance and we both can't and say whether it's good

**[24:10]** or bad and I think there's a lot of value in that I think it gives people a

**[24:15]** lot of comfort on what they need to work towards and I think it takes a lot of

**[24:18]** noise and extracurricular activity that can be focused on the job out of the

**[24:22]** equation and then I the rest of the stuff I think is fairly straightforward

**[24:28]** I think it might be straightforward but I'd actually like to dive in a little

**[24:33]** bit more detail because I think somebody especially kind of moving into a sales

**[24:38]** management role for the first time this is so classic you take happen to you

**[24:43]** it's gonna happen to salespeople till the end of time you take a great rep take

**[24:49]** them out of the field now they start managing and it's a whole new skill set

**[24:52]** it's a whole new thing so when you're setting the expectation of what good

**[24:57]** looks like maybe some examples how specific do you get I know we talked

## 25:01 — OKRs at the VP level, activity at the rep level

**[25:01]** about SLAs on things but is there anything else in there that might be

**[25:04]** surprising to a sales manager of how specific you are to directly communicate

**[25:09]** what good looks like so I traditionally work on like an okay our system that's

**[25:18]** probably not revolutionary right so I think when managing like I'm in my role

**[25:23]** today as CRO I'm gonna be managing VPs so it's my job to set the strategic

**[25:29]** priorities of the revenue organization align them as closely as I can to the

**[25:32]** founders vision in the company and then make sure every individual department

**[25:36]** understands how they can set their strategic vision for their department in

**[25:41]** line with mine and then I allocate resources to those leaders in order to

**[25:45]** hit the objectives that I most highly prize okay so to the degree that I

**[25:49]** miss allocate resources then I'm likely not prioritized appropriately and that

**[25:55]** would be people time or money right there's normally the resources that I'm

**[26:00]** dealing with so at that level I try to keep it succinct enough that what are

**[26:06]** the four to six things that we care the most about how are we doing on those and

**[26:11]** then are we regularly checking in on those I do I do a meeting with my

**[26:14]** leaders every two weeks and we try to call our shot for the quarter in terms

**[26:19]** of metrics that are going to lead to success how are those going what did we

**[26:23]** think was going to happen if it's doing better why if it's doing worse are we

**[26:27]** cutting bait do we understand what we've learned and then we we kind of move on

**[26:31]** so that's the way I do it today and I try as hard as I can not to be more

**[26:37]** prescriptive on the tactical activity level stuff that has to be done because

**[26:41]** I want to give people the agency to operate inside of a framework that I'm

**[26:45]** setting the strategy for make sense makes sense now but on a rep level I will

**[26:53]** get far more specific about here's the activity expectation than I expect okay

**[26:59]** now activity you're responsible for okay so nothing words you can give me effort I

**[27:06]** can't really get effort from you like it's not my job to pull effort from you

**[27:10]** of course I need to give you an environment where you can flourish and

**[27:13]** you feel motivated and all of the things I said before are still true but you

**[27:17]** need to bring the effort to the job that really is your responsibility not mine

**[27:21]** and if I've hired correctly I usually have to turn people down not up in that

**[27:26]** in that world right usually people are shot out of a cannon yes I also phrase

**[27:32]** it the same way I want someone you know pushing me not me needing to push them

**[27:37]** too yeah so when I feel like oh wow I better keep up with somebody that I've

**[27:41]** run on the team yeah that's a good that's a good sign yeah my challenge is

**[27:45]** usually I need if I'm managing a rep I need to be the second moment most

**[27:49]** informed person in their territory second mm-hmm if I'm one we've got a

**[27:54]** problem because now I'm more I I am now more knowledgeable about your market your

**[28:02]** territory your competition your funnel your customers than you are that's not

**[28:06]** great that's not great so you owe you owe me the effort you OS the effort and

**[28:13]** then when it comes to quality it's a collaborative effort where I'm these any

**[28:18]** deficiency that we see in the funnel tells us something about a coaching

**[28:23]** opportunity an opportunity to improve so you're really good at driving but you

**[28:27]** know pipeline and people are very interested in the pipeline but we're not

**[28:31]** seeing the conversion rate that others are seeing or that we would expect that

**[28:35]** you expect for yourself that's fine I bet you somebody has a solution out

**[28:39]** there together we can work on a solution to how to improve it it's not a problem

**[28:43]** sent from God this is you know something we can work on together and so who's

**[28:47]** really great at it what are they doing what can we incorporate into that now

**[28:50]** as a manager I can help you do that and I should help you do that but that's you

**[28:57]** know I think that's where I get into the recipe type stuff is I'm getting I'm

**[29:00]** mixing the activity level with the quality makes it makes a ton of sense

**[29:06]** and then and then moving into the second one compensating fairly easy to say I

**[29:12]** think most people want to do that I don't think anybody's leading a team

**[29:15]** saying I'd like to underpay the team and then just hope they do well I do think

**[29:21]** sometimes though especially now this this might be one of the first times I'm

**[29:25]** experiencing this and in my career is with inflation and and things changing

**[29:31]** like what does good compensation look like where do you go to make sure that

## 29:36 — Paying fairly when your best rep joined at the bottom of the band

**[29:37]** you are compensating the roles fairly yeah so our people department does a

**[29:42]** good job of using you know like named database of roles that give you

**[29:48]** compensation bands that we try to stay you know have a benchmark for and stay

**[29:52]** in there so it acts as like our source of truth for our we objectively inside

**[29:57]** of a pay band for our region and for the role relative to comparable companies

**[30:04]** but I expanding on your point do we're were you leading people during the

**[30:12]** pandemic and sort of the you were okay I started first real people leading was

**[30:21]** probably 2015 or so where it's like a sizable team and and working on that and

**[30:28]** then pandemic hit and things started to really expand especially in the tech

**[30:34]** industry and then ever since it's just like what what does good compensation

**[30:41]** look like sometimes it looks really good here and even certain regions you know

**[30:47]** we'll get candidates that are really excited about a certain thing and then

**[30:50]** others where we're like three times off and like how is there that much

**[30:54]** disparity in pay expectations out in the market right now well I break yes I

**[31:00]** agree and I bring it up because there was a moment somewhere like in or coming

**[31:05]** out of the pandemic where there was a shortage of talent people are just like

**[31:08]** paying like crazy for talent everybody's everybody's comp was just going up

**[31:13]** dramatically and it was a real challenge to try to understand am I paying fairly

**[31:18]** am I paying appropriately in and I'll give you I'll give you another example

**[31:24]** you tell me whether you've experienced this or not you hire somebody in a sales

**[31:29]** role who is a little bit more junior so they're on the lower end of the comp

**[31:34]** spectrum comp range and they're an incredible out performer they end up

**[31:39]** being a complete superstar that you think is you know going to continue to

**[31:44]** do great things for your organization for a really long time but if you're

**[31:48]** being honest their base salary in their OTE is lower because of their you know

**[31:55]** experience when they joined and that that's fair because you took a chance on

**[31:58]** them and they took a chance on you so that's that's fair but if you look at

**[32:02]** their performance today you think crap a competitor would pay probably way more

**[32:06]** for this person today because it's been a few years and they're just a star and

**[32:10]** then you're left with the challenge of like am I getting a deal is that what

**[32:14]** I'm trying to do am I compensating this person fairly or am I legitimately just

**[32:18]** hoping they don't get an offer from one of my competitors because then I'm

**[32:22]** gonna pay them up yeah right right have you been in that scenario before 100%

**[32:28]** and especially here at at lean scale we have people the very beginning there's

**[32:33]** only so much we could pay at the beginning so like a ton of people took a

**[32:38]** real bet on me took a bit on the company and then I am so quick to for high

**[32:45]** performers so quick to catch them up to where we think that role should be with

**[32:52]** the right experience because also if you lose that person the amount you're gonna

**[32:58]** spend on recruiting and time and not and having that seat vacant it's like what

**[33:03]** is what is a little bit more in their salary versus the cost of needing to go

**[33:07]** fully replace this person it's not even close yeah yeah the the I think it's

**[33:14]** great you do that by the way I do you think do you think that's unique I don't

**[33:22]** think people are intentionally not upping people's pay but I don't think

**[33:29]** they're paying attention to it I think what happens is they have their eyes on

**[33:33]** other things and then a couple years go by and they haven't really addressed it

**[33:37]** or they maybe don't have a really great review process where it's getting flagged

**[33:40]** we have it flagged we use we use rippling and it'll literally say like

**[33:44]** this person's been here a while and compared to other people in the role you

**[33:48]** might want to up their stuff they're like okay yeah so I think some people it's

**[33:52]** more just negligence and then and then that person leaves and not even not to

**[33:58]** make it like too exaggerated but you're not just missing their performance at

**[34:01]** that time if they were a top performer you're missing what they're going to be

**[34:05]** in the next six months 12 months 24 months - so you're missing out on that

**[34:09]** potential and totally agree and they won I agree with your assessment I don't

**[34:15]** think I hopefully people aren't doing it in a

**[34:19]** malicious way I think legitimately either that that information isn't

**[34:22]** bubbling up above their manager level right maybe the manager doesn't know

**[34:26]** they have agency to actually increase a salary pretty dramatically to catch

**[34:29]** somebody up so I think there are a lot of reasons for it but I do think it

**[34:34]** happens and and what I would add is that person or those people tend to be the

**[34:41]** great culture people in your organization and they tend to be a great

**[34:46]** kind of like examples of a growth in an organization looks like and so you know

**[34:51]** you love to have those people who started started you know as an SDR or

**[34:57]** whatever had got an 80-year-old and was a little bit junior but then crushed

**[35:00]** quota continue to go on and on and the stories are you know rocket fuel for the

**[35:06]** other other folks that in the organization that see that person as like

**[35:12]** of the people that they look up to and so to lose them is is heartbreaking so I

**[35:15]** think setting that example as you're going through and exactly what you talked

**[35:19]** about you're at a startup you're hiring people at disparate compensation bands

**[35:23]** you're probably getting trying to get a lot of people on the boat we just want

**[35:26]** to be a part of the team and so yeah salaries are a little bit mixed up and

**[35:30]** you look back and it's been a few years and you think I might have to like

**[35:36]** maybe give this person a 50% increase in their base salary and that person's not

**[35:42]** asking for it but I kind of I'm kind of at a decision I'm doing it because

**[35:47]** that's the thing I want to set the example to my team of no we we pay

**[35:51]** fairly we're not looking for a deal and so they don't need to raise their hand

**[35:54]** that's something that we do for folks so that you know a competitor doesn't say

**[36:00]** well I'm willing to give you 50% more and we say oh well we'll match it's like

**[36:04]** well if you were gonna match why didn't you just do it like why do I have to ask

**[36:07]** for it yeah if they have to ask it's already too late and and I've been on

**[36:13]** the receiving end of this too by the way I've had some fantastic leaders

**[36:16]** throughout my career and I've wasn't even on my radar I was happy with my comp

**[36:22]** I was really enjoying the job enjoying the cult everything we're doing and

**[36:26]** excited about it and I would just get a call like hey we added more options and

**[36:31]** increase your salary to this just want you to know like we're really excited

**[36:34]** about what you're doing and to me I'm like oh my gosh we're gonna go run

## 36:39 — The raise nobody asked for

**[36:39]** through a brick wall for this company like that would get me fired up so much

**[36:43]** because it's not just communicating that it's communicating a level of trust in

**[36:49]** every other aspect of your role and every other aspect of the organization

**[36:54]** too because it's saying hey you see everything and you notice and you're

**[37:03]** gonna treat me fairly no matter what it is and you're not gonna wait for me to

**[37:07]** raise it as a red flag so it says a lot when you do that totally great in you

**[37:14]** said an important word there which is trust in like there there will be times

**[37:18]** where you have to deliver tough messages to people around changes that you're

**[37:22]** making to territories or changes that you're making to quota or whatever you're

**[37:26]** gonna eventually gonna be in a spot where you have to say this isn't gonna

**[37:31]** feel really good but I'm gonna have to do it and and the the trust that you've

**[37:39]** hopefully built by doing things like that will will hopefully carry you in the

**[37:43]** conversation for somebody to say you've always done you've you've done the right

**[37:47]** thing productively for me in the past and so although I don't like this I'm

**[37:50]** willing to we have built trust enough that I'm willing to see it through and

**[37:56]** that's I think that's like super important in keeping the culture right

**[38:02]** now let me let me ask you this though have you had the opposite have you had

**[38:07]** people where you were you were under earning and nobody said anything and you

**[38:12]** found out I don't know if I ever found out but there's been a few times I

**[38:18]** assumed and maybe the company wasn't in a position to pay at a certain rate or

**[38:25]** not but it all it did was kept my eyes and ears open for any other potential

**[38:32]** opportunity so if because it feels like hey I'm kind of getting used here and

**[38:39]** if they would kind of keep my pay here and there were times where I would ask

**[38:43]** like hey this feels low I'm doing some benchmark research I'm not asking to be

**[38:47]** greedy it's just like this feels pretty low and yeah it just made me think okay

**[38:55]** well then it also puts you in a situation where like I can't really meet

**[39:02]** certain needs too so like I have to go somewhere else or find something else so

**[39:08]** just puts you in that position right away yeah I admire people who can do that

**[39:14]** well I'm not good at it I'm not good at lobbying for money on behalf of myself

**[39:22]** I'll tell like any most people who come to me I'll usually say who asked for a

**[39:26]** raise is good for you for advocating for yourself you know step one good for you

**[39:32]** and I don't do that well so I'll like I don't know how to do it I don't know the

**[39:37]** right words to use I don't feel right doing it like it's not a thing that just

**[39:42]** comes naturally to me and I don't understand I'm comfortable in you know

**[39:47]** other ways that might be conceived perceived as you know like not

**[39:51]** confrontational but sort of like where friction might be involved so when I see

**[39:56]** people do it well I think that's cool I don't know how to do that well I think

**[40:02]** if you have if you have to do it then ideally you just don't have to there's

**[40:08]** only been a couple times where I felt like I had to really speak up and say

**[40:11]** something and if that's the case and there's probably already other stuff

**[40:15]** going on unless you just have a completely wrong perspective but every

**[40:19]** other time I have felt even if it was lower but maybe I had high trust I felt

**[40:25]** hey I know they're doing the best they can and there's probably some

**[40:28]** opportunities for growth later so I I trust they're not trying to get a deal

**[40:32]** on my expertise or experience whatever it is they're just that's everything that

**[40:38]** they can offer at this point in time but I also trust that it will grow in the

**[40:41]** future I think that's okay but if you feel like hey am I getting screwed here

**[40:46]** are they just doing this because they feel like they can yeah then it's just

**[40:50]** more systemic than that yeah that's right and you make a good point which is

**[40:55]** there there are times where companies just simply they don't have the

**[40:58]** resources for it and you understand that that's different that's different from I

**[41:01]** know you have the resources you're just not doing it it's important just right

**[41:05]** right okay I'm taking a chance on earlier company but I also know coming in

**[41:09]** here means as the company grows there's gonna be so many more opportunities so I

**[41:13]** think that's that's okay but these are all the things where something as simple

**[41:17]** as compensate your team fairly can be so much deeper and mean so much more than

**[41:24]** just making sure their W2 looks good so I think you staying true to that and

**[41:30]** making it important helps keep those teams keep them longer keep them

**[41:36]** performing well and have that psychological safety to yeah keep doing a

**[41:40]** good job I I hope so and I think the resources to do the job is one of those

**[41:46]** things that might look obvious that's also important because there are times

**[41:51]** where people need sometimes it's a manager who needs personnel you're

**[41:57]** asking them for a performance and an expectation simply not resourcing them

**[42:01]** with the people they need to do the job really well and that doesn't feel good

**[42:05]** right I know what my performance is supposed to be you and I are aligned on

**[42:09]** it I am being compensated fairly you're always respectful nice me but I don't

## 42:10 — Resourcing the job — the fourth thing, and the one leaders skip

**[42:13]** you're simply not giving me the people or the money or the time to do the job

**[42:18]** well and that doesn't feel fair so it doesn't feel like I'm being set up to to

**[42:22]** be successful and I think just as a framework it's important to almost just

**[42:29]** zoom out from some of these decision in particular when you're managing managers

**[42:32]** and say well if this is kind of our if this is table stakes for people who work

**[42:36]** here is it true that they have the resources to do their job is that true

**[42:41]** to the standard that we expect and if the answer is no but well just tell me

**[42:47]** though tell me the butt part right because I would rather spend more money

**[42:52]** than I thought I had to spend to stay true to the thing of like it it's just

**[42:56]** fair to give somebody the resources they need to do the job and so I understand

**[43:01]** that there are financial repercussions of that or it's not what we forecasted

**[43:04]** it to be but that's the consequence of being wrong so but we ought to do it we

**[43:11]** ought to not do the alternative how do you how do you keep in check I agree

**[43:15]** wholeheartedly I think I feel like maybe I have some judgment on when it's hey

**[43:22]** this person's genuinely under resourced versus this person's just kingdom

**[43:27]** building in the company and asking for the world and the results for their

**[43:31]** coming I'm sure that there's a spectrum between those two things do you have any

**[43:36]** way or questions you ask yourself to help discern if this person's asking for

**[43:42]** stuff that's unreasonable or if it's a fair ask it's tricky right that part's

**[43:49]** tricky yeah one symptom that seems like a problem to me is when when a leader

**[43:57]** when every problem or new issue in it and that leaders organization can be

**[44:02]** resolved by a new hire we have a problem mm-hmm okay so it's sort of like we

**[44:09]** really need to do X Y & Z now for our customers okay we'll have to hire

**[44:13]** somebody for that do you is that true right and then in it and it might not be

**[44:21]** sort of like empire building but it might just be like the philosophy that

**[44:26]** everything that needs to be done means incremental headcount I think is

**[44:30]** somebody who's not solving to be efficient and effective they're solving

**[44:35]** for you know the easiest path to success that way and without keeping sort of the

**[44:42]** cost structure in mind so I think that's a that's kind of one of those red flags

**[44:48]** for me is like is that is that true just because we have one more thing to do is

**[44:53]** it true that we need an incremental headcount of a person to get it done so

**[44:59]** that's not it's not the perfect self but that's one of those things that when I

**[45:03]** see it I think hopefully hopefully that person's doing okay the other is like

**[45:07]** when somebody's performance is starting when you're starting to worry you might

**[45:11]** have had this experience where like this person has taken on a lot and it might

**[45:16]** be possible they're getting close to being in over their head and they're

**[45:21]** scrambling a little bit and the answer is always because they don't have enough

**[45:24]** resources that's always the answer and your job as a VP is to manage resources

**[45:32]** and to you know manage the strategy for your department that could be a sign of

**[45:38]** a problem right so those are things I look for I think it's a delicate balance

**[45:44]** admittedly I think when I get it right I call more by I actively call people I

**[45:50]** did that this morning there's somebody who have a really really fantastic team

**[45:56]** I mean that and I called somebody this morning because I know this person does

**[46:02]** this person does anything and everything you ask mm-hmm and I I call more to say

**[46:10]** how are you do you have everything you need yeah do you have do you feel like

**[46:16]** you have everything you need to do everything you just told me do you have

**[46:20]** that that's more of a concern for me any more than the than the opposite which is

**[46:26]** probably which is a testament to them I think likely right yeah I think again

**[46:31]** like when you're in a position where you have to hold people back versus needing

**[46:35]** to push them I think that's that's us I've had I have had that too where I've

**[46:40]** had to force people to take more resources like no you cannot take on

**[46:43]** this other project you cannot take this other thing on you already have too many

**[46:46]** things I already see that you're working all night and on weekends like I'm gonna

**[46:51]** force you to take PTO you need to go on a vacation yeah like those which yes

**[46:57]** fantastic people to have on your team but it is dangerous if you let them just

**[47:01]** keep running they will burn themselves out too and yeah if they don't take

**[47:06]** advantage of their kindness and goodwill and ambition - I think that's right and I

**[47:13]** also think it's a good lesson in sort of helping the leader mature into their

**[47:19]** role is like a thing I will say is just be careful you know people are gonna roll

**[47:25]** roll balls to your feet just be careful which ones you pick up because people

**[47:30]** roll them like balls come to my feet every time I just don't pick off pick

**[47:33]** off them up because once I pick it up I own it right and so just be just be

**[47:37]** careful that sometimes in an effort to be helpful you start picking a bunch of

**[47:41]** things up and now you know their problems are your problems or what

**[47:46]** somebody else could have done you're now responsible for and as a leader I

**[47:50]** expect you to be able to have to be able to allocate your prioritize your life

**[47:56]** prioritize your department allocate your resources appropriately and to the

**[48:00]** degree that your priorities outweigh your resources that's also a managerial

**[48:05]** thing that we have to work on right right and so that's fine that we need to

**[48:10]** work on it but that is a part of the job so I know sometimes hero ball sounds like

**[48:16]** a ton of fun but it's also maybe the sign that you know maybe maybe we're

**[48:21]** over prioritized in your department and not necessarily under resourced and

**[48:26]** that's a worthwhile conversation to have to absolutely you appreciate someone who

**[48:32]** knows how to pass the ball to the fourth bucket that you had again sounds obvious

**[48:36]** but I'm sure there's some depth to it everybody treated with respect are there

**[48:40]** any non-obvious things that you see leaders doing management teams doing

**[48:47]** that are really breaking that contract and they may not even realize they're

**[48:52]** doing it I don't think being treated fairly means the same thing to everybody

**[49:02]** right so it's sort of like am I fast well that's a relative term right and

**[49:09]** maybe fair has some similarities to it and so I think you know I don't mind

**[49:17]** Anthony friction okay I really don't sure um I I said before I like spirited

**[49:25]** bait that's completely true I've you direct communication as a sign of trust

## 49:30 — Respect, friction, and the "no assholes policy" problem

**[49:30]** so the faster I can be direct in my communication and you can with me I think

**[49:33]** this is great we're starting to trust each other that's a good thing but I

**[49:38]** think it's totally fair to be able to separate performance from somebody's

**[49:44]** personality I think that's completely fair and so to objectively review your

**[49:50]** performance independently to who you are as a person is fair so you can have bad

**[49:56]** performance and still be a good person that's true good people have bad ideas

**[50:02]** also that's that's also true and so I think conflating like maybe softer

**[50:11]** things that are associated with fairness into that bucket is not really what I'm

**[50:15]** talking about I think the thing I'm particularly excluding here is like I

**[50:20]** don't like incivility I just don't like it so when people are not civil to one

**[50:27]** another I that's not I don't like it it doesn't you should be fair to people in

**[50:34]** in terms of etiquette and civility is important and I understand things are

**[50:38]** gonna get the pressure is gonna mount okay and there gonna be times when we're

**[50:44]** doing great and there's gonna be times where we feel like we're never doing

**[50:47]** great and that's all baked in the cake that's all gonna be a part of the

**[50:50]** experience we can control how we communicate to each other we can control

**[50:54]** how we treat one another and we should not get so exercised that we start

**[50:59]** treating each other unfairly that's not okay and so that's more the spirit of

**[51:05]** what I'm talking about but I think it's not everybody gets treated like you're

**[51:11]** nice to me a hundred percent of the time well that's not always true I'm not

**[51:17]** unkind I would never humiliate you I would never you know I would never

**[51:23]** demean who you are as a human as a brother as a son as a mother that's

**[51:28]** completely out of bounds right but we can't we can't talk about your

**[51:32]** performance objectively that's completely fair and consequently you

**[51:36]** should be fair to me it's it's not always a one-way street you should be

**[51:41]** fair as it as a worker in the our place of business and so that's a perfectly

**[51:48]** reasonable bilateral contract to get into so that's more of what I mean I I

**[51:52]** think people will take it to its true have you ever heard the term of like we

**[51:55]** don't hire jerks sure yeah we have that we have a no ass no assholes policy you

**[52:01]** ever hear that it's like the most common thing in the world that you're

**[52:03]** absolutely and it's like with the fine asshole like it's um I'm open for

**[52:13]** business for like a ton of interesting personalities you know what I mean I

**[52:17]** really am I think I think it's like really interesting to work with people

**[52:22]** with different viewpoints and different opinions and different I find it

**[52:25]** fascinating and I'd love to hear it and then sometimes I'm prone to weighing in

**[52:30]** and you should be open to that too that's fair so that's a little bit of

**[52:38]** what I mean when there's should be like a standard of etiquette and treatment of

**[52:41]** one another that reaches a level of civility that we all mutually agree is

**[52:46]** above board and it's okay if it gets a little bit out of bounds it's okay but

**[52:51]** you should take accountability and you said look at that was too much and I'm

**[52:55]** sorry I got exercised and I probably shouldn't have said that and I apologize

**[53:01]** and I do I do like a little bit of that too a little bit of that zest on the

**[53:06]** team means you don't do that if you don't care so if you care whether it's

**[53:12]** you care enough about yourself and your career and who are as a professional or

**[53:15]** care about the company and what we're doing what we're building here and the

**[53:17]** importance of it that's usually what drives out that type of passion that may

**[53:21]** cross the line so yes that not all the time but but if it never happened

**[53:30]** you're such a you're such a founder in this way I agree but I think I think the

**[53:36]** the thing so I'll go back to like the the guy I was talking about in my first

**[53:41]** job who I now I'm gonna reference him again right I told you I reference him a

**[53:44]** bunch we're gonna have to have John on here next so John's a legend so so and if

**[53:53]** he heard this he would be like mortified so he he would he would get very he

**[54:03]** would be disappointed if we didn't advocate and pound the table for issues

**[54:07]** that we were having interdepartmentally and with our customers why are you not

**[54:12]** why are you guys not outraged that this is happening and why isn't anybody so

**[54:17]** that's what you're that's not out of bounds at all that's fair this department

**[54:22]** is not doing good enough to take care of my customers I'm not talking about the

**[54:25]** leaders are bad people or they don't care I'm saying this that's not good

**[54:28]** enough and it's hurting my business and it's hurting our business to reach our

**[54:31]** customers needs and it's hurting sales and it's a problem that's completely

**[54:35]** fair that's completely fair now you start insulting it well it's because so

**[54:40]** and so is a jerk and he's a let okay well that's too much you don't need to

**[54:44]** go after personal attacks inside of us assessing what the problem is and that's

**[54:48]** more of what I mean around like the civility elements if it's helpful right

**[54:53]** but you might just a little bit just a touch a dash yeah dash of incivility it's

**[54:59]** kind of like if building a product and nothing ever broke going fast enough are

**[55:05]** you pushing hard enough like you're not finding your limits then I think you're

**[55:09]** leaving some some stuff on the table so on that note though what where we'll

**[55:15]** find common ground on this is like I would really respect like if I would

**[55:19]** really respect it from a leader if they're like look this is this is what we

**[55:23]** tolerate I don't that's okay here you know what I mean now a little bit that's

**[55:28]** fine so expect it good enough good enough the ambiguity is what I have a

**[55:34]** problem with right yeah the ambiguity that like I probably curse a little bit

**[55:40]** more than I should but when I talk to people who are potential applicants

**[55:44]** sometimes I'll curse in the application process and I will say you know we curse

**[55:48]** around here sometimes now if that's a problem for you probably shouldn't care

**[55:54]** no that's so because you might hear it and that's kind of what's acceptable

**[55:59]** around here and you can make a moral judgment on whether that's right or wrong

**[56:02]** but that that's kind of the way it works and so that's that's what's gonna

**[56:06]** happen and that's fine that's fine well one one thing we talked about a little

**[56:12]** bit on the prep session I would never bring up anybody's kids unless they kind

**[56:17]** of gave up an opportunity to do so but I know you have some kids that are

**[56:22]** starting to enter their early career years they're just kind of starting off

**[56:27]** and I do think I mean my goodness I think even the last five years so much

**[56:33]** of how we work has changed and so I would love to hear your perspective on

**[56:40]** the advice you're giving them and maybe also advice you might give someone who

**[56:46]** aspires to be a CRO one day too yes so you're right I have two kids one she's

**[56:56]** gonna go back to college next week which is both a bummer and really good a bummer

**[57:02]** because she's it's great to have her in the house and it changes the whole like

**[57:07]** ecosystem in the house having her so that part's a bummer and then also awesome

**[57:13]** because she's like fired up to go back and it's cool that you know she loves

**[57:19]** college and she's sort of her own woman and that means you know she's she's

**[57:26]** good for the world so that makes me feel good so it's both good bet and then my

**[57:31]** son is going into his last year of high school and he's the best so he is like

**[57:40]** such a self-aware mature guy I learned stuff from him frequently because he's

**[57:47]** he's a good dude so advice that I give them is sort of not necessarily it's

**[57:56]** starting to be professional a little bit

## 58:01 — Dad Wisdom

**[58:01]** this is I'm gonna tell you this and like regret it immediately I like my wife

**[58:10]** doesn't even know this so I started I like started a little text thread with

**[58:15]** them and I renamed it dad wisdom okay for posterity but that's so when I when

**[58:22]** I think of something where I'm like I really hope they know this fired off

**[58:26]** into the text thread and then they have it so they can always go back to dad

**[58:29]** wisdom I don't know how valuable this is we're early in the experiment but I've

**[58:35]** started well give it a couple years you plug that thing in a clod I mean they

**[58:42]** won't miss a beat it's gonna be awesome

**[58:50]** yeah they don't even need to talk to you anymore yeah yeah what have I done what

**[58:56]** have I done no I wisdom is probably like overselling a little bit I think the

**[59:02]** thing that I try to one of the things that I learned like later on in life

**[59:09]** which I wish I would have known earlier is like I told you a little bit of the

**[59:15]** story of my career where I like I didn't know anything about sales I wasn't

**[59:19]** totally sure whether I wanted to be in sales or not I didn't know anything

**[59:23]** about commercial loans far from it I certainly didn't know anything about

**[59:28]** health care dentistry so I was off to a bad start Anthony I didn't know anything

**[59:32]** and then I started to as I was telling before I started to really enjoy the

**[59:37]** dynamic dynamic of I really like talking to people and I'm genuinely interested

**[59:41]** and curious about people so I started to enjoy the job and I really liked how

**[59:45]** self-directed I could be and how much agency I had over you know the outcome

**[59:49]** of my performance and there's like an element of independence streak that's

**[59:53]** always been a part of my life that certainly is valuable in a salesperson's

**[59:57]** world right sort of traditionally I was into athletics and that kind of stuff

**[1:00:01]** which is I know a little bit of a cliche but but the I I worked really hard to

## 1:00:09 — When a career stops being survival and becomes a choice

**[1:00:11]** get to a point where my basic needs I was married young I've been married for

**[1:00:15]** 26 years and we were married very young and I was very eager to get us to a

**[1:00:20]** point where our basic needs were met okay whatever that means whatever that

**[1:00:25]** meant for us at the time which was like I want us to have a house or an

**[1:00:30]** apartment that's nice nice I'm putting in quilts and you know a car that's nice

**[1:00:35]** enough and food and the ability to like have some discretionary income for

**[1:00:41]** vacations or entertainment and that kind of stuff or clothes these are basic needs

**[1:00:46]** as I defined them as a young person and in sort of like classically I like every

**[1:00:56]** next opportunity in my job was very obvious so if you're like an inside

**[1:01:01]** salesperson being an outside person is an obvious progression and being an

**[1:01:04]** outside salesperson and managing people is an obvious progression and then do

**[1:01:08]** get it everything is sort of like very logical and very and and getting

**[1:01:12]** promoted it's fun and you get paid more and getting the recognition is fun but

**[1:01:18]** after my basic needs were met everything was kind of a choice I was making

**[1:01:23]** between like job satisfaction and impact and you know whatever joy was being

**[1:01:30]** derived from the work or not that I was doing and title and compensation those

**[1:01:36]** were the compromises right right and and I didn't fully appreciate that I just

**[1:01:42]** sort of like plotted through my career to get promoted promoted promoted and

**[1:01:45]** then I was like do I still love this am I doing the thing that I still love

**[1:01:53]** because I told you I set out not to be a salesperson I was one I met my basic

**[1:01:59]** needs by being a salesperson and then I got promoted for having whatever talent

**[1:02:05]** or good performance somebody perceived relatively in that and and I that was

**[1:02:11]** what seemed like the right thing to do but more than my basic needs have been

**[1:02:14]** met and then I sort of was in a position of like it feels like I've chosen a

**[1:02:18]** career did I do it deliberately yes or no you're pretty deep on the game of

**[1:02:25]** life you've got a lot of squares here so yes is this where you want to be or is

**[1:02:29]** there a fork that you missed yes in it and it would have been valuable whether

**[1:02:35]** I would have listened or not is a different story right but it would have

**[1:02:38]** been valuable to have the perspective of like I'm choosing at this point I'm

**[1:02:42]** choosing what to do I don't have to is this a choice I want to make relative to

**[1:02:47]** an alternative choice and what are all my what are my alternative choices and

**[1:02:51]** so it's so I'm clearly not advocating for like playing hopscotch with your

**[1:02:58]** career in perpetuity although if that's what you want that's fine it was more

**[1:03:04]** you know once you get 10 15 years into what you're doing you kind of have a

**[1:03:09]** career in the switching cost might be meaningful for you right and so that

**[1:03:13]** wasn't explained to me right sick because I went from survival having my

**[1:03:18]** basic needs met to whatever relative success I I had or excess above my basic

**[1:03:23]** needs was met and I found myself in a career now I'm a happy guy that's true

**[1:03:28]** but I want my kids to feel like they're not in a race for survival they can be

**[1:03:37]** deliberate about the decisions they make in their career and be thoughtful about

**[1:03:40]** why they're doing something over an alternative and so and maybe in

**[1:03:45]** answering the CRO question I think I've had to think a lot about this in my life

**[1:03:50]** which is like outside of making money and having a title or whatever what is

**[1:03:57]** it that I genuinely like about my job what what are the things that are

## 1:04:00 — The cocktail: comp, title, industry, people, impact

**[1:04:00]** non-negotiable that I like doing and I'll give you some examples which is

**[1:04:06]** like is it is it the compensation is it the title is it the industry right is it

**[1:04:13]** the the leadership of people is it the job specifically that I'm doing you get

**[1:04:24]** it there's a cocktail of things there so like is it true that I would be equally

**[1:04:28]** happy if you just paid me more and gave me a better title and put me in a

**[1:04:31]** different industry and I didn't lead people and I didn't feel like I had an

**[1:04:35]** impact is it would that legitimately make me happy and it wouldn't right I'm

**[1:04:40]** no different from anybody else like if you give me everything I want all the

**[1:04:43]** time I get worse that's kind of the way human behavior works right if you have

**[1:04:49]** young kids you learn this like really quickly which is like what's the best

**[1:04:52]** way to make it unhappy two-year-old give them everything they want whenever they

**[1:04:55]** want it it does not improve their behavior at all does this make sense so

**[1:05:01]** far I am learning that counter intuition right now raising young kids so yes it's

**[1:05:09]** resonating well it's also fun but inside of that I think the thing I've

**[1:05:16]** challenged myself is like I I sincerely love leading people managing people I

**[1:05:22]** love it and I have a huge amount of energy to direct at what I perceive to

**[1:05:29]** be helping or developing people or using whatever knowledge and experience and

**[1:05:34]** background I have to to maybe help somebody develop through their career

**[1:05:40]** or achieve what they want to do I love it it makes me really really happy and

**[1:05:43]** that has nothing to do with the industry that I'm in it just makes me happy doing

**[1:05:47]** it and I would be genuinely miserable if I felt like I worked if I didn't have an

**[1:05:54]** impact that I thought was positive on people it would make me really really

**[1:06:00]** unhappy I would be a genuinely unsatisfied person and I want that to be

**[1:06:06]** in the sense of like that's for me that's not for everybody else that's for

**[1:06:11]** me to determine whether I think that I'm having an impact right it doesn't have to

**[1:06:15]** be true for you might look at it and say you're not that's okay that's for me

**[1:06:19]** right you would never do that but I think I think those are reasons why I

**[1:06:28]** take a job or continue to work with a job and at this point in my career who I

**[1:06:33]** do it with matters so much I mean in the more of those things I can compile

**[1:06:40]** together I love to be selfish in this way which is like I want that and that

**[1:06:46]** and that in that that's what I want and if I don't get it I don't want to do it

**[1:06:51]** and that wasn't always true for me in my career there were parts there were times

**[1:06:54]** of my career where I had to do jobs that I didn't think I was having an impact and

**[1:07:01]** I didn't think I was doing about but I needed to get somewhere and so the fact

**[1:07:05]** that I have some of that now is like a prized possession of mine and so anyway

**[1:07:12]** that's the way I go about doing it today and I think that like matters for people

**[1:07:15]** who are chiefs of whatever makes a ton of sense yeah I love it love the cameos

**[1:07:25]** well and I think I think being intentional about the choices you're

**[1:07:30]** making knowing the trade-offs that you have and then especially if you're early

**[1:07:33]** in your career knowing hey something that you enjoy doing may have a slower

**[1:07:38]** start that's okay play the long game if you're passionate about something if

**[1:07:42]** there's a certain work style that you want to have or things you want to be

**[1:07:45]** incorporated in that and I have found that too later I mean yes at the

**[1:07:50]** beginning and like hey I have just survival and bills to pay so I'll pretty

**[1:07:54]** much do whoever pays me the most at this point but then yes getting more

**[1:07:58]** selective as you go you know with lean scale when you said who you work with

**[1:08:03]** matters the most that's been the coolest experience for me I'm in a very

**[1:08:08]** fortunate position to get to pick everybody works here or at least try to

**[1:08:12]** get them to work here but I have like my childhood best friend is here my wife

**[1:08:18]** and I work together I'm the oldest of five I and my youngest sister works here

**[1:08:23]** and then just the people that we've been able to attract and the type of

**[1:08:29]** culture you've been able to build I get fired up to work here today so I think

**[1:08:34]** when you're building something like that you those become so valuable I would not

**[1:08:40]** take more money to trade off all of those things that I have built in here I

**[1:08:48]** love that and good for you for feeling that way and in you you might have had

**[1:08:54]** this experience I know I have where people who haven't challenged that

**[1:09:00]** priority for themselves can make decisions that aren't best for them so

**[1:09:06]** you you might have a performer who's like I'm leaving or somebody in your

**[1:09:11]** company that you think is it doesn't matter what you think their value or not

**[1:09:14]** but they're they're leaving and the reason they're doing it might be I'm

**[1:09:20]** gonna get paid more and they're giving me a new title right and you think well

**[1:09:24]** have you considered the other elements have you considered the aspect of like

**[1:09:27]** who you work with the impact you feel like you have in the organization you

**[1:09:32]** know the the industry itself that you're doing and how you have you considered how

**[1:09:37]** valuable those are to you and whether you're gonna get that or how likely you

**[1:09:40]** are to get that at your new place and that doesn't land all that well with

**[1:09:44]** some people who are determined but how frequently do you see them unhappy for

**[1:09:49]** those reasons later on and learn that lesson and that's a painful lesson to

**[1:09:52]** learn right sometimes I think you just have to go through it it's one that's

**[1:09:59]** tough to teach but pretty obvious once you've actually been in that situation

**[1:10:03]** where oh I have traded some things I value really highly for a bigger salary

**[1:10:11]** bigger title whatever it is but I'm feeling empty or missing all these other

**[1:10:17]** things that I know I've experienced in other places so but it's very hard I

**[1:10:22]** think to explain that to someone I think you have to live it yeah I think you're

**[1:10:30]** right I'm sure you're right it's one of those things that you can't convince

**[1:10:33]** somebody to feel that way they kind of just have to to your point feel it and

**[1:10:39]** go through it and learn the lesson themselves which is hard to watch but

**[1:10:43]** part of maturing and growing up I guess so yeah I think about it a lot and I try

**[1:10:53]** to I try to scrutinize and pressure test it every once in a while just to make

**[1:10:57]** sure I'm right you know in a minute when I take a different job with people I

**[1:11:01]** would you know just to see whether the priorities are in the right place and

## 1:11:05 — "Why do you want to be a CRO?"

**[1:11:05]** that's I'll get I'll get people who ask me a little bit of like I think I want

**[1:11:10]** to be a CRO how do I and that's one of those questions I'll ask is what what do

**[1:11:15]** you think you want to be like why do you want to be a CRO like what is it and

**[1:11:19]** that question for some people is like they don't almost understand the question

**[1:11:23]** it's like what do you mean I'm in AE I just told you I want to be a CRO why is

**[1:11:26]** that hard to understand but that's like fair enough but that there is like that's

**[1:11:32]** like promotion for the sake of promotion and that's not always good this by point

**[1:11:36]** and you made a really good point before which is like how frequently do you see

**[1:11:40]** a really top performer get into management and struggle and it's like

**[1:11:44]** yeah that happens that happens a lot I have a lot of respect for people have

**[1:11:49]** the self-awareness to be like I think I'm good at this I don't think I'd be

**[1:11:51]** good at leading people so I'm not gonna do it yeah and and I've seen a lot of

**[1:11:56]** those people do really well too I mean they're there's top top ICs that are

**[1:12:02]** making much more than managers or in it so you know just do your passion about

**[1:12:08]** follow that along get great at your craft and then like those other accolades

**[1:12:14]** and things can follow it doesn't only have to be a people management thing

## 1:12:19 — Wrap

**[1:12:19]** totally cool thank you so much for everything you shared everything you

**[1:12:28]** went through I love the contract that you have with people who are on your

**[1:12:32]** team making sure that they're compensated fairly treated fairly have

**[1:12:38]** the tools to be successful and know what good looks like I think anybody listening

**[1:12:43]** this can learn quite a bit from following how tactical that can be and

**[1:12:47]** then just the advice on how to think about your career and being intentional

**[1:12:51]** with it and looking outside of just a small lens of your salary and title but

**[1:12:58]** opening up that aperture to all these other things that you might value so

**[1:13:03]** I'm probably gonna have to subscribe to the dad wisdom sub stack that I think

**[1:13:08]** you're gonna launch and then I'll plug Claude into it make sure my kids don't

**[1:13:12]** miss any beat either but I really appreciate everything can't wait to

**[1:13:15]** follow what you're doing now and then see what you do next in your career I

**[1:13:19]** really appreciate it it was great it was great talking to you and thanks for

**[1:13:23]** having me on I really appreciate it