¶ Modern Sales Leadership
Matt BenelliThis week on the Coach the Scale podcast, I sit down with Keith Rabkin, cro of PandaDoc and the seasoned go-to-market leader with an impressive resume featuring leadership stints at Google, adobe and Johnson Johnson. Keith's unique path to sales leadership without ever carrying a bag proves that tenacity and curiosity can still drive extraordinary results.
He'll share his two-by three coaching framework, tackle the pitfalls of lone ranger sales behavior and explain why tough conversations that we don't want to have are the cornerstones of true customer centricity and solid coaching. Whether you're scaling a team or leading from the front, this episode is packed with actionable insights for modern sales leaders. Take a listen, oh yeah, please let us know you're out there. Hit the subscribe button on YouTube, comment, like and repost on LinkedIn.
Let's go. Welcome to Coach to Scale how modern leaders build coaching cultures. I'm your host, matt Bonelli. Join me as we build a community of like-minded professionals who share the belief that effective coaching improves the performance of every team member. Our mission is to help leaders become better coaches. The Coach to Scale podcast is sponsored by Coachum, the world's first AI coaching execution platform that leverages evidence-based coaching to increase quota attainment.
And with that let's get started. Today's guest has amassed deep and broad-based go-to-market experience at iconic companies Google, johnson Johnson and Adobe. Currently he's Chief Revenue Officer at PandaDoc. Keith Rabkin, welcome to Coach to Scale.
Thanks for having me, matt. There is nothing that I would rather talk about than coaching and talent, so this is the perfect activity for my afternoon and time well spent.
Matt BenelliAwesome, all right, we are aligned. So, keith, let's kick it right off with a MythBuster type question, and the question is this there's a lot of myths in this crazy business that you and I have been part of for a long time. What's one of those myths, when it comes to coaching and leading salespeople, that you believe is misguided, maybe even complete BS?
Yeah, I wonder if you've heard this one before, matt. I don't think it's total BS, but I think it's maybe misguided, which is that the only thing sellers care about is making money, and you know, I've heard that time and again right Coin operated. Just create the right incentive plan and then, you know, the reps will figure out how to get there. And I think, while there is truth, a lot of people want to be in this business to make a good living.
There's a lot more, and I think salespeople in general have the same motivations that others do. They want advancement, they want recognition, they want to do a good job. I think a lot of sellers take particular pride in their craft. That's something that I've seen, certainly in the last two years at Panadoc. We have a lot of sellers who they want to obviously beat quota and hit those accelerators, but they also want to set personal records.
They want to do the best job they can for the company, and so I think, as a coach, one of the things we have to do is make sure we're creating a system by which our reps can earn, but also dealing with more of these intangibles and identifying what is the one thing that makes my seller tick, and how can I lean into that to drive performance for that rep and help them reach their goals?
Matt BenelliYeah, and I appreciate you sharing that. And yes, I have heard that time and time again and, like a lot of the myths, there is some truth to it. It's not 100% false, but I like what you said. It's misguided and I may you know years and years ago what motivates you Money. I want to make the most money. I probably said something stupid like that along the question.
What advice would you give to that hiring manager when he or she asks an interview question to get at the heart of what motivates somebody? And that person on the you know, maybe newer in their career that wants to please, thinks saying making money is the right answer. So they say making money is important. That's what motivates me, and you and I know that that's not really the case. What's the follow-up question to that?
Yeah, I mean I would continue to dig how is making money going to make you a better seller? Or what other traits do you have that's going to make you a better seller? Because that's going to start to uncover that underlying motivation. Or what do you want to like? Maybe great, that's amazing that you want to make money, but tell me about what you want to accomplish in the next month and how you're going to grow in this role.
Because, like that growth, if you turn it to growth, it's less about the outcome and more about the path, and I think what we want to understand is what path are they on and do they see themselves moving into? Because that's going to help us understand these inherent motivations.
Matt BenelliYeah, and those inherent motivations are really what makes the, what makes it all go, what makes where the rubber meets the road, if you will. So we kind of hit on hiring and some things that have very high level here. But, keith, when you think about your leadership playbook that you've developed over the years, is there a playbook or a framework you use with your leadership team to help better coach and lead your salespeople?
I like to think I'm really big on structure, so this is a really structured approach that will work for some managers, may not work for others, but I like to create a two by three matrix and I may not like actually tell people I'm creating this matrix, but I use it internally and one of the columns is goals, and one of the columns is what do I need out of this team member? And the goals come from them, right? I'm asking them what do you want to accomplish? And the what I need is great.
I may have some development areas for this person, right? Maybe it's they need to be better at pipe gen. Maybe it's they need to be better at closing.
Matt BenelliMaybe, it's.
They need to be better at driving cross-functional projects that actually have a bigger payoff for the entire organization.
So those are my two columns, and then I have sort of three rows which are like what's the tactical, what am I going to do, what are we going to work on in the next three to six months, next one to two quarters, and let's understand your goals and how you're going to accomplish them in the next quarter or two, and then let's understand how you're going to raise your performance in the areas that I'm thinking about for the next one to two quarters.
And then you've got this like middle bucket, which is like all right, let's look out over the next one to two years probably more, like you know, one, one and a half years what will indicate success for you and how do we get you there? Their goal may be to get promoted. Their goal may be to make it to P club Um, just start to like fill that out, and then my goals might be different too, based on my assessment of this person's talent, where I need them to get on their metrics.
And then there's the long-term, which is what do you want to be when you grow up? You know, five years down the line, 10 years down the line, and how do I help you start to get there? And how does that fit in with my organizational plans?
Right, If I've got a great enterprise seller who's crushing it and continually beating quota and driving new highs for the business, I want to make sure this person stays and I've got to figure out what are the motivators that then help this person continue to stick with my organization.
Matt BenelliSo when you talk about goals and you said that's what the employee, that's what the rep provides, let's say, and then it's what you, as the leader, need from that person, and you said they might need to ask better questions in discovery, whatever it might be, no-transcript.
Like, does that skill that I think? Like, is there any alignment where I have to self-assess that I need to get better at discovery too? Or are you saying, hey, listen, I don't, it's not. You may not have thought about this, but I have and you is to get promoted and your goal like you can have goals that are, like, very tangible, like I want to get promoted, I want to make the club, I want to, you know, be the top rep, but then there's more amorphous goals.
Like I want to be better in negotiation. I think one of your jobs as a coach or a manager is to make sure you can tease those apart and understand both of them. Like this box doesn't have to be one thing for each category. What I like to do and I think one of the beauties of this matrix is that if I can tie what's in my column to what's in their column, it's great.
So if your goal is to get promoted, but my goal is for you to be do better discovery, then I'm trying to tie them together and say you know, your best path to get promoted is when you get better at discovery, because that's going to help you continue to generate pipe, continue to make sure you close deals at a higher clip, and that's going to lead you to the outcome you want. It's not that I'm telling you no to being a better negotiator.
It's just tying what I want you to do back to the goal that you're explicitly asking for.
Matt BenelliOkay, no, that makes a ton of sense, and thanks for sharing that. Ok, no, that makes a ton of sense and thanks for sharing that. Keith, one of the topics we talked about in our initial call together is that you pride yourself on being customer centric and leadingused. When you talk about customer centricity, what does that mean to you in terms of how you lead a team.
So I think there's this interesting. There's maybe another myth with sellers right, there's a few Sales is like a like it's a job for a lone wolf, right versus being part of a team. And I think this team aspect of selling really ties into customer centricity in a real way.
¶ Sales as a Team Sport
When you're in sales, no matter if you're a new business seller, you're an str or you're an expansion sales rep who's doing renewals and driving expansion, or you're a combined rep that's doing all of this you're part of this like broader organization that has this goal of getting customers and keeping those customers and wanting those customers to come back for more.
And I think when we approach from a standpoint of not being customer centric and just trying to get a sale, no matter what, we're actually putting ourselves above the organization. And it ties into that lone wolf mentality which may be okay for you know, hitting quota in a given quarter, but it's going to start to hurt you down the line, right? It's either your CSM team is going to start to get annoyed with you, your manager is going to realize their net dollar retention is suffering.
Your customers may get you a reputation, especially if you're in a small industry, you know, or if you're an enterprise where there's just not that many companies out there like people talk, these things come back, and so the best sellers I've seen are the ones who continue to understand that this is a long game, right, and I'm going to be around as a seller for 20 or 30 years.
The customers I have at one company are going to be my customers in the next company and the ones that I get to a really great outcome will come back to me for more. So we have a fantastic rep on my team today and he's actually won many of his customers from his previous company because they trust him so much, which only comes from getting them to a great outcome.
If he had said, hey, I'm going to close the maximum deal I can, I'm going to sell them stuff they don't need, right, they're not going to come back to him because they realize, like he's out for himself, not for this, like mutually beneficial relationship, yeah, and so I think this pays increasing dividends over time right in terms of both the rep and the company.
Matt BenelliYeah, I really appreciate what you said about like no lone rangers and, um, you know one of, you know a counterpart, you know another revenue leader in this business, uh, mike Deloya. He was on the show not too long ago and he commented. He said if you, if a rep comes to me and says, hey, I closed this big deal and I did it by myself, um, the first thing I'm going to say is why you left money on the table and you didn't help the customer as much as you could have.
So I just I love the way this, our industry is focusing more on sales, being a team sport and that's a big part of being customer-centric and that there's no lone rangers.
So I totally agree. I mean, I think sometimes it's hard to ask for help, but when you realize it's a team and a lot, of, a lot of great sellers come from sports backgrounds, right, so there should be this natural inclination that you can get help. Um, get your execs on a call, get your csm in there, get your se. I think the se? Ae relationship usually works pretty well. But the more people you bring I think there's some gong statistics that the more people on a call, the higher the close rate.
So you know it's in your best interest to do it and it helps the customer get to that great outcome.
Matt BenelliYeah, I think it increases the close rate and it increases the deal size. Those are two good things that we all want. More of right, absolutely so, keith.
¶ Navigating Difficult Conversations in Leadership
One of the topics that's come up well, it comes up a lot, but recently this is something that we've been digging into and peeling back the onion on is this whole notion of having difficult conversations. Tons of books written about it. The problem is not a new one. What are the folks that impress you the most right, the most seasoned, successful sales leaders? How do they deal with having difficult conversations?
I would say that the best that I've worked with are very honest, but they don't and they don't hide, like they don't hide away from giving the bad news, but they give that bad news with compassion. You know, and personally I think this is one that took me a while to get used to, right, like I have this dread about having the hard conversation, like I don't want to have it. It's like it sucks, it's just, it's painful.
But I think over the years, what I realized is you're going to have this conversation one way or another. So you know, it's like when you wake up in the morning and you're like I just want to lay Right, never, never. But like when you you just do it, like you just go get it done and when you get it done, everybody's in a better shape, right. Like you're not hiding.
Then you don't have to have a conversation later where the person who's getting maybe this tough news was like well, why didn't you tell me this months ago? Like my behavior didn't change in this time. So it's like it's about being genuine and it doesn't mean like I think one of the challenges, too, is we say like well, when you're giving critical feedback, you're being harsh. Actually, you're not being harsh. Just just lead with the facts. Like it's not that you're a bad seller.
Your close rate is low. You did not generate enough pipe. Yeah, I need to see this different. Like it's not. That's nothing personal about you. This is I'm. I have expectations for you and you didn't meet the expectations, but it's very honest. And then it's I'm here to help you.
But, but you do need to hit these marks, um, and I think the more you can be upfront about that, the better situation you're creating and the better opportunity you're creating for this person to make a decision on their own part about what they want to do with this feedback.
Matt BenelliYeah, like most people, you mentioned that you don't love having these types of conversations. I mean, no one does, but they have to be had. Do you find, especially with all of the different data that's being aggregated and stored? Do you see that the data sometimes helps have a more difficult conversation because you can point to the data as opposed to coming off as like? Here's how I feel about you.
Yeah, absolutely, like I said, grounded in the facts, because if it's a feeling based conversation like that's where it gets hard, because now it's how you feel about me as the person getting the feedback versus this is my expectation of anybody in this role. You have to generate this pipe. You have to close this much that you treat customers with respect right, like if you're mean or you're mean to teammates, like that's a, I have received X number of complaints or negative pieces of feedback.
That has nothing to do with how I feel about you. I might absolutely love you as a person, we might have the best time like working together, but this is the expectation of the role and I think that makes it really easy for somebody to understand. Again, they may not like that feedback, but it is very factual, which at least allows them to internalize it and absorb it much more easily.
Matt BenelliOkay, and that segues into a question I have about you know lessons learned right, have about lessons learned, painful lessons. You've been doing this a while. My guess is that it's not all rosy sunshine and rainbows. Is there a painful lesson in this business that shaped how you approach leading teams today? Maybe an aha moment, if you will.
I think if you ask my team one characteristic about me, they would say urgency. I have an extreme level of urgency, so I don't like waiting for things to happen. But my lesson is that change always takes longer than you expect. So what do you do about that?
You start planning ahead more and you start thinking about things you can do in advance and you signal to people who are doing a great job, you signal to the organization about the direction the organization is moving, and when you have critical feedback, you share it early, because the longer you sit on it, the longer that change is going to take. And so that's probably the biggest lesson. I mean, that's one of the things that drove me the craziest.
¶ Adapting to Change in Sales
When I started here at PandaDoc, we had a very transactional sale. We were pretty far down market. We just closed, closed, closed, and one of the changes we made was to introduce value selling and I was like, oh, this isn't going to be hard. I have really smart reps. I mean, I have a great team of AEs and AMs. I was like this is going to be easy, like they're super smart, they know this product inside and out. But changing that behavior just took a really long time and it just surprised me.
So, repetition, planning ahead and continuing to like, draw that roadmap of where you're going is the best thing you can do to make sure you're bracing for that, that change that will take longer than you want it to.
Matt BenelliYeah, um, nobody loves change. Uh, you know, some people it's easier than others. And I remember a book written as a while back now by some folks out in the Bay area, I believe Chip and Dan Heath. They wrote a book called switch how to change when change is hard.
And they, you know they talked about the repetition and shrinking the change, and you know it's just a just a super important book about, like, how change always takes longer than than you expect and so, but but then again, the, the other adage in our business is the only thing constant is change, right. So so, um, I guess, when, when you were like, I mean, I'm curious, when you're focusing on value selling, right, when you rolled it out, you have smart reps, right, you know they get it.
It's not intellectual that that's going to knock them for a loop here it's, I guess, maybe it's comfort zone, things like that. What are, what were some of the things I guess more specific that you did to hang in the pocket there and make sure that it wasn't treated as oh, this is, uh, the flavor of the month. This too shall pass.
So there's quite a few things you know. Start with great enablement. You've got to have an amazing enablement team and I think most sales leaders love their enablement team and I'm no exception. My team is fantastic. But you start with that as a basis to make sure they're grounded and they know what they're trying to get to. And then the second thing, back to team sport is my managers right?
I want my managers constantly reinforcing this and they're going to be meeting with the reps all the time, so the more that they're telling them this, the more it's going to be top of mind. I think the challenge really is what you said, which is it's comfort zone.
Like, yes, I get this, I know this is going to lead to better results, but in a moment when I'm on a call and I go into a Zoom meeting every single day in my job, I just go back to what I know Right and so, like you've really got to get them way past that point of change. So the team, the enablement, and then like, beat the drum. My sales staff is amazing at doing this Constantly. Every, all hands we have, we're beating the same drum of like these are our priorities.
Here's why this matters, and it's not just the what, it's the why. So I think continuing to match those two things with great enablement and great management leads to these better results.
Matt BenelliAnd I love that you brought up the other leg to the stool and enablement, because if you don't have a strong enablement team, it's hard to make anything stick moving forward, as we both know. So one of the things you shared with me before in our initial conversation was that you come from a non-traditional background. You've worked at some great companies. You know Stanford, wharton, great education but you didn't carry the bag.
And you know some would say, oh, why am I going to listen to this guy? He's never carried the bag. And some would say, hey, it's a superpower, you know I. Sometimes it might be better not to know, right, you can find people who say both, but let me focus on the former one. What do you say to those critics who might say Keith's never carried the bag?
I. What I would say is you've got to study. You got to study to be good at anything and hard work is the number one differentiator. Like, how many? How many people hire sales reps based on what college they went to? I think very few. I think people want to see reps who put in the work and are good at their job. And I would say the same thing about me.
Like, don't hire me because of my education, pedigree or the companies I work for, but hire me because I put in the hard work and trust me as a revenue leader because I put in the hard work. No one's watched more gone calls than I have. No one is reading more articles. Well, maybe Steph, my VP of sales, is. But you know, I think those are the things, right, and my way of selling is going to be different than the CRO who grew up carrying a bag for 20 years.
But I also know where I'm not good, right? Don't, don't call me in to go sell to GE, like that's. I'm not going to do a good job there. I'm going to be okay. But if you want a CRO who's going to be really personal in a call and be customer-centric, which I think more and more buyers are looking for. Our expectations as software buyers has been raised in particular, as we expect technology that behaves in the business like it is in the consumer world.
We want a customer-centric buying process, and when I get on calls, there is this level of authenticity and honesty that comes across that I do hope helps us win deals, and so I think that's a big piece of it. And then I think my team would say Keith's really done a good job of raising performance because he has been a student of the game and he looks at data all the time. I think that's the piece right, this understand, and I work hard to look at the data to say, you know, I see this trend.
The reps that are top performing do these things consistently and that leads to better outcomes for these sellers.
Matt BenelliYeah, no, I really appreciate and I enjoyed the answer. It's kind of funny because you always get people who say so-and-so didn't do that particular job, Like well, they don't have any street cred and as a sports fan, I'm a Boston guy. I don't think Bill Belichick was. He certainly wasn't a pro football player and I don't even think he played football at a high level. And that's the case with most professional teams. Many of them weren't players and they certainly weren't great players.
But you know, I really like the answer. It's like you put in the work and you put in the work yeah.
I mean one other point, like so I worked at Google back in its heyday, right when a lot of the great products were being introduced. You know, google Docs, which now I mean that's what I use in my job, that's what I used in my last job, it has become a mainstay of what we do. They introduced, you know, google Cloud. They introduced Chrome, the browser, all these YouTube. They bought YouTube and they turned it into this juggernaut. Back when I was there, we did not hire based on the resume.
We were encouraged to look past the resume and the job on the resume and to hire for aptitude. And for me, that is a lesson that I take with me. Like yes, there are some jobs where you like experience is a good signal that somebody knows how to do something, but great interviewers will test for aptitude and use that aptitude score to make the hire.
I would much rather hire a sales rep who is showing aptitude, who is at a non-name brand company, than a sales rep who doesn't work as hard, doesn't show insane levels of curiosity, but worked at one of the top SaaS companies. It's a very easy choice for me.
Matt BenelliYeah, you talk about curiosity. One of the favorite interview questions that I stole from someone else along the way to kind of get at is someone really driven, are they ambitious, are they curious? But if someone comes in with I don't know let's call it 15 years of experience this person says I want to get to the to understand. Does this person have 15 years of experience compounded, or do they have one year of experience 15 times and you know?
And they really try to figure out like are they curious, are they ambitious, are they driven? And they really try to figure out like are they curious, are they ambitious, are they driven? So you talked about Google or, as my father-in-law would say, the Google. Put it into the Google. You talked about Google. You talked about technology. Ai is all the rave these days and if anything comes to mind, what are the salespeople or sales leaders?
How are they the best ones right now leveraging AI to be not more efficient, more effective?
I think we're just in the beginning stages, right. As much as there are great tools out there, I do think the people who are leading now have a you know just as good shot of being completely irrelevant in three years from a technology perspective. It's changing so quickly. So for me, the best thing companies can do and individuals is to experiment.
And it goes back to what we were just talking about Curiosity, the rep who is playing around with these technologies and I don't need to name names, there's tons of them out there. There's new ones coming up every day. The ones who are playing with it and figuring out what works are going to be the most successful, because they're going to find what works for them, and that may be different depending on your segment.
It may be different depending on your motion Are you inbound, outbound, Are you channel driven? These are all going to create different permutations that different tools will serve at different levels, and so experimenting and trying things out to me is the best path. That's kind of what we're doing now.
We actually have been playing around with about seven different tools to see which ones we want to bank on, which ones match PandaDoc style, which ones help our sales reps be more effective and actually turn into the end result. It's very easy to say this will make me more efficient, right? Oh, it writes my cadence for me, great. Did it actually result in an opportunity? How good is the pipe? Does it close at a different rate? Same thing with like intent data that's out there.
Combining those makes me more efficient too, because now I don't even have to go do research. But does that actually make me better when I get on the call with the customer and I haven't done any research? So I think a lot of it will be customized and depend, and a lot of this is still changing so rapidly. So my advice is play around a lot, you know. Get different team members to try different things, share those learnings and then start to make some bets.
Matt BenelliYeah, no, I love the idea of sharing the learnings. So, keith, you're over at PandaDoc, your chief revenue officer there. For those who don't know what PandaDoc is, can you say what the?
company does. And then also, what do you love most about working there? Yeah, so PandaDoc is a single solution for all your agreements and for sellers. That's super important because you send out sales agreements for Signature. I cringe every time I see on LinkedIn at the end of the month somebody says oh, we got our you know our DocuSign back. Uh, cause they're a competitor. What we have is a lot better for sellers, for several reasons.
One, you know, we give you better analytics on people who view your agreement. So today I'm talking about AI tools. We've got a PDF that was sent over by one of these vendors, and this vendor charges around $200,000 a year. So this is a pretty solid sale. This PDF is getting passed around like no tomorrow, and we're like I'm reviewing it, my head of marketing is reviewing it, my VP of sales is looking at it. These are great buying signals.
Now, because it's a PDF, this team has no idea that we're looking at this, which leads to two things One, they don't know how warm of a buyer we are, which means they can't forecast accurately whether we're going to close or not. And two, when I go back and negotiate, I'm going to play it cool, right, I'm going to say you know we're looking at five different vendors and you know you guys are just as good as the other.
But if they could go in and see how often I was personally logging into this thing and seeing, that's an incredible signal. So that's one way that we're different. Another is we actually make the branding really unique on these proposals. You know how often do you get like an order form that's just like this kind of boring quote and then put your signature right. Ideally, your company has assets that they can put in front. Here's how many years of experience.
Here's a case study and then the order. We bundle that all up and probably most importantly, the seller is we save you time. You know we actually prevent a lot of that back and forth with deal desk that sellers just hate working on.
Matt BenelliOh yeah.
And so that value proposition makes us a really great sales tool.
Matt BenelliAwesome. And so what do you love about working with the team?
The people at this company are amazing. We've got a global workforce. You know, employees from Ukraine, portugal, all over the US were fully remote, and we've just done this amazing job of bringing people together that have this goal of serving customers.
Panadoc was founded as a company that was here to help small and medium businesses succeed Mm hmm with giving them a tool that was disproportionately powerful relative to what larger companies had, and so this mission of helping companies be more productive, close deals faster, is core to our being, and we talk about it a lot, and you know my team is here to do the right thing for the customer. A lot of my sales reps will tell me they're like you know, keith, I didn't close this deal.
And I'm like why didn't you close this deal? And they're like this wasn't the right solution for this customer and as much as I want that sale, at the end of the day I also run CX. So like I'm like, okay, you made the right call because I don't want this customer to turn all in it.
¶ Coaching Influence on Leadership Success
Together we go to the right things and it's a fun environment. I mean, it's not always easy, right, we're coming from behind against some pretty large competitors, but the elegance of our tool. The great teamwork and the focus on doing what's right for our customer, I think makes it well worth getting up every morning.
Matt BenelliSo, keith, if somebody out there listening says wow, you know what We've been evaluating, so we need to evaluate something and we're interested and it sounds like PandaDoc sounds like it could be a good fit, and or someone says wow, it sounds like a great company, I want to work there. Like, where can someone learn more?
PandaDoccom We've got a very easy to find demo request form, which should make it very easy to get in front of a seller, and that is the best way to get into our pipeline and learn about the product. The websites we've done a really good job of making it accessible to understand what we do. There's some videos, there's some graphics, there's comparisons against other tools, and then we are constantly hiring, so our career site is on the website as well.
Matt BenelliAll right, constantly hiring. I'm career site is on the website as well. All right, constantly hiring. I'm sure a lot of people might like to hear that. So, keith, the podcast is Coach to Scale. We bring people on who have a point of view and who care give a crap about coaching and developing other people. People who care about that, like yourself, usually have had that behavior modeled for them somewhere along the way.
Can you tell us about someone whose coaching has had an impact on your career and your leadership style?
Yeah, I've had three fantastic coaches maybe three and a half is maybe maybe three and a half, but uh, the one who was most recent was my executive vice president at adobe, brian lampkin, who's just an amazing human being and, again, really customer focused, very aspirational, like constantly challenging us to do better, and I can remember a couple times he really lit into me but did it in a way where he's like like hard but then like pulled me up at the end and I think I think a lot of sellers and go to market people in general appreciate that, which is this.
I like I'm being hard on you because I know you can do this and I want to challenge you to do better. So, you know, brian helped me get into go to market.
You know, again, took a little bit of a chance on me because I was coming from more of an operational background and really appreciate what he taught me and I think I'm much better for that, like really pushing hard and then pulling people back up, and then that continuing to be customer focused, which a lot of my mentors have done for me Awesome to be customer focused, which a lot of my mentors have done for me Awesome, well, yeah, I mean, whenever you describe someone that you worked for in this crazy business as an amazing human being, you know the shout out to Brian, for that that's, I'm sure he.
Matt BenelliHave you ever told him that?
I don't know if I've ever told him that All right.
Matt BenelliWell, again, he knows I appreciate him, but I don't know if I've ever told him that.
All right, well, again, he knows I appreciate him, but I don't know if I've ever said that so I should.
Matt BenelliPeople love hearing that stuff.
¶ Coaching and Talent Development Strategies
So the who's your favorite coach? So think of it a little differently. Maybe a name a lot of people would know it doesn't have to be sports, but a lot of sometimes sports comes to mind. Who's your favorite coach?
out there and why what happened? I've got two maybe, and kind of similar in some ways, very different in other ways. So I'll start with the first. I went to Stanford. I went to Stanford when we went to the Final Four and I was a huge basketball junkie. Mike Montgomery was the coach, you know, and he put up a really good run in a very challenging environment at Stanford.
I think what he did well was he recruited well and Stanford had really hard guardrails around recruiting there Did a great job there. Great X's and O's coach. You know, in some very tight games would just like pull out wins. That you know. I remember we beat, we beat duke like I think, two years in a row and it was just like what, how's that even possible?
There's just no way this happened and he did it through like great coaching because I mean we had great players but they had like a ridiculous roster. So I think you know I love that about him and the x's and o's is kind of like that's how I think of myself as a CRO. Again, I'm not a salesperson, I'm more of like let me look at the data and figure out the plays we need to run. That would be like my back in the day answer. My today answer is Steve Kerr. I'm in the Bay Area Warriors.
I gotta love them and like, how can you go wrong? He's, he's got this amazing team, but, um, so got great talent, recruited great talent. But then again back to the X's and O's. He finds a way to maximize the talent, or he, you know, I think the other piece about him that's maybe different is he finds a way past obstacles. So grit, um, you know, curry goes down with an injury and somehow they still win, right, because he's figuring things out.
And I think any good leader is going to continue to find obstacles. Any good coach is going to have obstacles, right. People plateau at different times. People have life changes, right, whether it's getting married or God forbid illness or a pregnancy, like. But people good coaches find ways to solve through those problems and help maximize the potential of their team.
Matt BenelliSo those would be my two Great player, great coach, great results. Hard to argue with Steve Kerr, except I'm a Boston guy and I don't like what he did to Jason Tatum. I don't understand it, but topic for another day. Last question, keith, just have a little fun with it If you had to give a TED Talk tomorrow about one topic to a huge group, ted Talk style, what would the topic be and why?
So one person who worked for me said that he's never experienced more growth than when I managed him directly and we would talk about how he experienced this and he would say a couple of people who've worked for me have had this and I think, as I've sort of dissected what that is more, and it doesn't work for everybody, but it is almost this sink or swim viewpoint on new talent, and one of the things I do which, again, you have to hire the right kind of person for this to work is I like give them all the pressure.
I just I'm like here's everything you've got to do and go get it and I'm here to help you, but like I'm going to keep giving you more until you tell me, uncle, like when you tell me to stop, I will pull back and I'm just going to give it to you.
But through these experiences like I think of, like the term forged in a crucible, like that crucible of the pressure, it's either going to cause somebody to drop out, which is why this is not the right approach for everybody, or it's going to challenge them to reach new heights, which is why this is not the right approach for everybody, or it's going to challenge them to reach new heights and for me and the way I hire and the way I manage, I've gotten really good results out of that.
So I would probably talk about that and you know how you match the hiring with people who succeed in that coaching style. You know, and maybe your follow-up question is going to be how do you hire the right people? You hire people who like challenges, you hire people who are curious and you hire people who have a tenacity to want to go and overcome obstacles because, like they don't want to give up when you're putting this on them.
Like eventually, everybody, even the most tenacious people I've hired, are like OK, this is enough, please stop. At which point, like we load balance and we figure things out, but it just produces so much growth with people.
Matt BenelliWell, I love the connection. You're right, it does segue into about hiring, and if you hire the right people, you can do things like that. You know one of the big programs in Marine Corps leadership training, you know they actually call it the crucible, and one of the principles within the crucible is to give people, to give the students, the aspiring Marine leaders, absolutely much more than they could possibly accomplish in the allotted amount of time. They can't do it. They can't do it all.
So they have to think, they have to prioritize, they have to maintain even keel, they have to ask questions. But in order to do that, you have to have, you have to bring certain ingredients to the table, which means you have to have the right recruiting process. And so, yeah, no. Thanks for sharing that. I loved it, keith, we covered a lot of ground, you know. We talked about the crucible, we talked about hiring. We talked about having difficult.
We talked about the crucible, we talked about hiring. We talked about having difficult conversations, customer centricity. Really appreciate everything you brought to the table today.
Thank you, thanks for having me on. There's very few things I like talking about more than talent and getting people to great results, so I appreciate you having me on.
Matt BenelliWell, likewise and it was obvious that you like talking about it and I noticed on LinkedIn there was somebody fairly recently wrote a review for you and you know they just talked about how you help them and you care about them and that's why they followed you from company to company and that's a huge vote of confidence for for any leader.
That's the person I was talking about. Who is the one who is like you've challenged me so much and I guess he kept coming back for more challenges, but I've tried to get him over here to Pandadoc, but so far he's resisting.
Matt BenelliAh, all right, I missed that. I thought he was there, but yeah, but still, he followed you to multiple companies, so that's a huge testament to your leadership. Keith, thank you very much, and also thanks to everyone out there watching and listening. Appreciate you being there. If you liked what we're bringing, let us know what you like, but also, more importantly, let us know what you'd like to see and hear more of.
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