Coach2Scale: How Modern Leaders Build A Coaching Culture

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This 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.

Awesome, 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?

Yeah, 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.

Yeah, 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.

Maybe, 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.

So 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.

Okay, 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.

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.

Yeah, 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.

Yeah, 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.

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.

Yeah, 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.

Okay, 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.

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.

Yeah, 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.

And 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.

Yeah, 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.

Yeah, 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.