Coach2Scale: How Modern Leaders Build A Coaching Culture

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Matt Benelli: All right. I'm excited to have the conversation with today's guest as you'll see. This guest walks the walk when it comes to servant leadership and driving organizational success through others. He spent his entire career in the industry technology B2B SaaS, working with industry titans such as Oracle, Salesforce, Palo Alto Networks, and he's also a limited partner [00:01:00] at Stage two Capital like myself.

Bill Bagshaw. Hello. Welcome to the show.

William Bagshaw: Matt, hello. Greetings from Vermont. Thanks for having me. I'm honored to be here.

Matt Benelli: Great to have you Vermont out to Park City, a couple of places that this is considered the the low season. Both places are gonna boom when the snow comes, but still beautiful right around now.

William Bagshaw: It is. Yeah, I'm up here to do a little fishing, as you can see on the wall behind me. I have a thing for catching trout and such, so I'm going to give that a shot later on this afternoon.

Matt Benelli: May they be plentiful. The great thing about the show here is that I get to speak to guests like you Bill who have been in the arena who've made mistakes and not only live to tell about them, but live to tell others about them, with the hopes of helping sales leaders and coaches and those committed to developing people.

Along the way. So let's let's get right into it and I'm gonna throw a softball question over to you to get us started. Bill. We, I know [00:02:00] over the years, because we've known each other for man longer than we probably care to remember 'cause we're getting old, but

William Bagshaw: were a brunette. You were a brunette when I

Matt Benelli: Yeah. You never age though.

Bill, what's a common myth about coaching salespeople that you now over time believe is misguided?

William Bagshaw: Yeah, I was thinking about this topic, because we were talking about it a little bit the other day. And I think particularly for front, first time managers. And I know, I think I fell into this trap. I think there's a lot of folks think they have to, I think a lot of managers over rotate towards focusing on the outcomes, the measurements and the outcomes, i.

e., forecast calls, how much have you booked, what's your pipeline, how much pipeline have you generated, all of which is important stuff, but I think, Newer managers can sometimes fall into a trap where they think pressuring on that, pressuring on the results, creating some anxiety around that, [00:03:00] proving that they're brave enough to crack the whip, if you will, that's what coaching salespeople is all about.

I'm a coach because I'll call my reps out if they're not generating enough pipe. I'll, I'm a coach because I'll call my reps out on, too much of their, they're not hitting their linearity targets. Too much of their pipeline is slipping from month to month, quarter to quarter.

And I think it's important to be mindful of performance. KPIs and such, but focusing on the end result is not true coaching in my mind.

Yeah, that's measuring. But do you know what I mean? Have you seen managers that think, Hey, I'm now a manager. I now got to crack the whip on those results.

How many calls have you made this week? How much pipe have you added? What have you closed? Boy, there's a lot that happens. Upstream from that, if you will, that I think falls into the bucket of true coaching.

Matt Benelli: A hundred percent. [00:04:00] A hundred percent. And and I've heard it a million times, most recently somebody said, my, as a manager, as a leader, my job is to make sure my people do their job. That's probably part of it, but I don't know if that's the whole kit and caboodle. I don't know if that's falling into the category of coaching and developing people.

But Bill, what do the best sales managers do that brings out the best in their reps? How do you achieve success through others?

William Bagshaw: Yeah. So first of all, I think that the, the managers that I've Seem to be the most effective that I have the most respect for have an element of what was the word you use? A servant's mentality? A servant leadership style? Servant leadership. Yeah. And I think that's, by the way, that coming back to your first question, that's another, early in management career mistake.

I see people fall into a trap on is the notion. Hey, I'm now a manager. You all work for me, man. You're all here to do what I tell you to do. Yep. And I tend to come at it and the best managers I've seen and I've worked for, and some of them very well. [00:05:00] They always maintain a servant leadership style element to their game, where I felt like I could go to them for help and assistance, guidance, coaching and that they felt intuitively, I think a lot of these folks intuitively felt that's part of what they should be doing for me as my leader is some amount of Serving me and what I need versus just telling me what to do.

Matt Benelli: And you talked about in the past I've heard you talk about the importance of. As a leader creating a psychologically safe environment. Can you talk a little bit more about that?

William Bagshaw: I can, and I think it's important in the context of complex solution selling. I've spent the bulk of my career, as you mentioned in your opening remarks Selling enterprise software and very complex sales cycles, 6, 9, 12, geez, 18 months. God forbid. Matt? And,

Matt Benelli: It was always a couple of months

too

long.

William Bagshaw: Always a couple of months too [00:06:00] long, right? Yep. Yep. Some years we wish we had a 13th month. Anyway, I think that, it's, there's so much complexity. So much changes from day to day, gosh, even hour to hour on key pursuits, key deals, if you will. That, the best reps that, that I've ever worked with are the ones that recognize that they need the soundboard with somebody.

It doesn't always have to be Bill Bagshaw or Matt Benelli. But they recognize that there's so much complexity. There's so many blind spots. There's a thousand ways to lose a deal. There's usually under one or two paths. And they recognize that there's a need to soundboard with experienced people.

And as a leader, I have always felt that I wanted to foster that. Folks that want to come and brainstorm, let's take an hour in a calm environment. We're not on a forecast call. We're not going to play stump to chump. I'm going to create a psychologically safe [00:07:00] sandbox for a rep to get on and for us to discuss all the flaws in their deals.

Somebody that you and I used to know at Oracle, first name Greg, I loved an expression he used to use, which is every deal is flawed. There's no perfect deal. And I use that line a lot. I'll give credit to Greg Linteman but it's so true, right? And so I think it's so important. As we look to maintain win rate, right?

That reps feel comfortable that they can get on the phone and a psychologically safe sandbox and put on the table, all the flaws with their deals, all the flaws with their sales cycles and gain help from their leadership chain and others on their virtual team to try and make strategic and tactical decisions that will lead to a high win rate.

​I think it's, the business I've been in for 35 years, it's a win rate businessman. They are precious, fragile eggs. It's hard to win these deals. You have to [00:08:00] create an environment where your team feels as though they can come to you and to the broader community to discuss everything that's wrong.

Matt Benelli: so the reps that performed, the people that performed the best, if you had to say one way or the other, did they come to you more? As their leader or did they come to you less because they knew it all or knew a

William Bagshaw: Absolutely. I'm going to name some names. that I consider legends in my career. Some of the best reps ever who, by the way, went on to do other things and get into management and such, but I look back.

At the time I was managing the people like Jeff Breslin and Pete Hesketh and Kim Carpico and Dave Viffieties and David Kreberg and rest in peace, Buckley Cooney, one of the best ever, these people called me the most. And again, it wasn't because I was so great. It was because they recognized the need.

To look for all the flaws, to look for all the blind spots. They were brave enough to ask for help humble enough to ask for help. And if I do say so, I created an [00:09:00] environment where that was okay. And it was a good thing. It was actually the fun part of the day was, the phone rings.

And and you get to tear apart deals and brainstorm and help them. And those reps that called the most, I'm telling you, they were the most successful. That's the short answer to your question. I gave you a long winded answer. That's the short answer. Absolutely. They were the most successful.

Matt Benelli: And I think that's important to reinforce. And time again, I work with, I. Salespeople, sales leaders, people, especially earlier in their career who think it's bad, who think it's a sign of weakness to ask their manager for help. And what you're saying is exactly the opposite. Over 35 years of doing this, the people that perform the best are those that sound boarded with their manager, called their manager or reached out to their manager the most.

And you're not saying that because it's you. But you're saying this because the top people sound boarded with a bunch of different people to include their manager, but it certainly wasn't a sign of [00:10:00] weakness to ask for help and for to poke holes in the deals. The opposite of that though, what's your observation for people who didn't ask for help?

What was the impact on win rates for them and for the organization?

William Bagshaw: They didn't have as many people looking out for them, looking out for their deals, poking at the deals, trying to find the wet, the blind spots, the weak spots, the traps that were set by the competitors. Therefore, their win rates were lower, materially lower, absolutely.

Lower win rates Yeah. And then it's a cycle, Matt, right? Then you get into a situation where now all of a sudden you are focusing on the results as a leader a little bit. Some of us sometimes we do it too much and you create a vicious cycle where they do start to fear coming on calls because they're getting beat up a little bit because their deals, they're losing deals, their deals are slipping.

I think as a leader, we need to break that cycle. And create that environment where they want to come to the call because they know ultimately it's going to put money in their pocket and they're going to feel a whole lot better [00:11:00] about about the job that they're doing.

Matt Benelli: A hundred percent. And so maybe the next part of that, when they come to you, when it's often said that the best sales leaders ask the best questions, what are your thoughts on that? What are one or two questions you've found super helpful over time?

William Bagshaw: One of them we were talking about this the other day, you hit me with this question and I was thinking about it and I was two things came to mind. One was something that's specific to, you know, an opportunity that may be in front of us. The rep in me, and then something that's more longer term.

So first I would say that one of the questions that I always like to ask is, Hey, what do you think this is going to cost the customer? Million bucks? Yeah, Bill, million bucks. Why would they give you a million bucks for this? It's amazing how the answer, sometimes, I don't know. Gee, that's a problem.

we're gonna have to discount to 50% . Hey man, and a lot of the software you and I have been selling, Matt, a million. We've done deals that are 5 million, 10 million, [00:12:00] 20 million, right? Why would this, they're gonna go to the C F O and the board of directors and they're gonna say they need to spend $5 million, 5 million, I'm sure there's lots of things that they could invest in for 5 million.

Why are they gonna give you $5 million? What? Serious problem are you solving for them?

Matt Benelli: What

William Bagshaw: How are you helping them attract and retain more customers? How are you helping them grow profit margins, grow profitability, drive the stock price, blah, blah, blah. How are you doing that with your software?

Matt Benelli: Remember

William Bagshaw: Remember Arun, Jani?

Matt Benelli: remember that name? So I always took something from him. It, it may seem super basic to everybody watching and listening, but Arun, Johnny, when in, I came to Oracle, I barely knew what a database was in 1999, and he said there's only three reasons. There's only three reasons why people buy this stuff.

It's either to, it's either to help them make money, to save money, or manage risk and all those things you just said and all the things that come up, it all falls into those three buckets.

William Bagshaw: [00:13:00] And Matt, I've been part of organizations. I'm gonna call another name out. Tom Bonus really led at Oracle there were two waves of it. So SunnySingsOrg and then Tom, John Boucher put Tom Bonus two people we know quite well, in a position to drive an initiative across the the entire business and commercial across North America.

focused on value selling and focused, I think we got to a point in the organization where there was as much focus, the energy put on answering that very simple question as there was in traditional demo prep, clicking around what you're going to show and this, that, the other thing, none of which matters if you don't have really good answers to the.

Question of why nor should I give you 5 million, to implement this stuff. I've seen great leaders make that part of their day in and day out with reps. And I've also seen great sales organizations actually dedicate resources to it as John did when he put Tom in place to drive that.

And it was wildly successful. So that's [00:14:00] another long winded answer to a very simple question, but that is one that I like to ask a lot. And then taking a step back from the deals I do like to ask reps, especially as we approach QBR time or annual review time what are your suggestions for moving the business forward?

Let's put aside your forecast. Let's put aside your deals. You are, you're in the weeds. You're closer to it than me. You actually know more about, a lot of reps don't realize they actually know more about the business than their management chain. That's a weird dynamic, right? But it's true because the reps are living it minute to minute, hour to hour.

And. I was fortunate enough, especially in my Oracle career rolling up to Amit Singh and John Boucher and ultimately to Keith Block, that there was this expectation and even going back as far as the John Nugent days the culture that was created was one where we were rewarded for coming forth with ideas that could help the greater business move forward.

And I had a few initiatives that, were uptaken and driven [00:15:00] nationally and all sorts of people did, including Tom Bonas, like I mentioned. And I think it's a really powerful thing. I've been in organizations where that's not the case, where it's very top down. It's very autocratic. And quite honestly, at Oracle, that shift did happen, right?

But I benefited in my time there from an environment where I felt it was incumbent upon me, it was expected of me, to be able to answer that question, certainly in a QBR but even on a daily basis. And I like to ask my reps that now,

Matt Benelli: Yeah.

William Bagshaw: a result of learning that what could we be doing better, how can we move the business forward?

And it could be something we're going to do with the BDR, something we're going to do with partners, something we're going to do with field marketing. There's a wide range of different kinds of things, different levers that we could pull. But I like to ask that question as a leader, and it ties into the psychologically safe thing. I think my experience has been that the best reps, the mature experience reps, I named a bunch of [00:16:00] them, who are the ones that call the most, that engage the most, they actually we all work for money, Matt, right? But we also, we have pride. We, we worry about, we want to be self actualized.

Matt Benelli: Yeah, hang on to that. 'cause I ha Bill, hang on to that thought about where you're going there. 'cause I love it and I have a question to extend this part of the discussion. I you absolutely did. So just to kinda recap that, the question was what types of questions, do great sales leaders ask?

And one of them was, Hey, why is this prospect, why is this client gonna spend X amount of dollars? And the other one was, What are you doing to move the business forward? On the latter one I think you learn a lot about what you hear. 'cause if you hear nothing, right? That tells you maybe you don't have the, the brightest bulb.

Maybe you don't have the best rep. Maybe he or she's not engaged for whatever reason. But the good ones, the best ones have great answers to which you can share with the rest of the team. Going back to the first question you said though, which is why [00:17:00] is the, Customer or prospect gonna give this money, $5 million, a million dollars.

There's a lot of people, especially in SaaS, high volume businesses that aren't doing million dollar deals. Bill, wouldn't you say the same question applies though? Why is the prospect giving us gonna spend and invest any money?

William Bagshaw: For sure. Yeah. Because think about it. They have to go defend. Let's just say it's a hundred K. That's still a lot of money. They need to go defend the ask and there needs to be business reasons for it.

​And I'll say this earlier in my career, I was afraid of those conversations.

Like I'm not an accountant, I, I don't, I can read a balance sheet and an income statement, but I wasn't that good at it. What I learned was... Come on,

Pride of Ithaca College. That's right, Pride of Ithaca College, the business school up there. Geez, I shouldn't have, you have to delete that part. We'll edit it out, yeah. I I don't want to offend the business school at Ithaca College. But, in all honesty, I was not getting in [00:18:00] front of a CFO. The true economic owner of the project who's holding the purse string and having a con a business conversation. Forget about the product, forget about the demo, forget about the user interface.

All that stuff that I, earlier in my career, I tend to fixate so much on that, the product and what are we gonna show? We gotta do all these dress rehearsals of the demo and all that. And that's not that stuff's not important 'cause preparation in that way is important. I would argue that none of that matters. If you can't have the business discussion around why do anything,

right? And the sooner that let's get back to coaching. I think, especially working with earlier in career reps, coaching your reps, giving them the confidence in those one on one conversations, let them trial run with you, dress rehearse with you, the business conversation around value, around why do anything.

Super, super, super important, [00:19:00] huge coaching opportunity out there for, I think all sales leaders, because a lot of folks, present company included, first few years, I don't know, maybe first 10 years out of school. I didn't have a lot of confidence in those conversations. I now find it. An easy conversation.

And what's fascinating about it is I think if you, as a sales leader, if you get good at those conversations as a rep, if you get good at those conversations, it almost doesn't matter what you're selling,

Matt Benelli: If you can answer those three questions, why? Why buy anything? Why buy our solution and why buy it now? You insert the company or the solution name here, right?

William Bagshaw: get a little smarter on talking about CapEx versus OpEx, get a little smarter on talking around return on investment et cetera, et cetera go a long way in your sales career and I'll emphasize it again. If the focus. If the culture is a beat down culture, if the culture is the beatings will continue until what's that expression until morale [00:20:00] improves.

Matt Benelli: Yeah,

that was like, that was part, that was one of our mottos in the Marine Corps. The beatings will continue until morale improves. Yeah,

William Bagshaw: Yeah. You're tougher than me, so you you obviously hung in there through all that. But I, I just, I think it feeds into that too, though. Is my point is that if reps. They're getting their sea legs. I'm talking about the business aspect of it, the value side of it, boy, if they're afraid that they're going to beat up, get beat up for saying something stupid you're not going to get reps to a point where they're really sharp in this area.

And I think it's crucial that they get sharp in this area.

Matt Benelli: A and I had a mentor one time who could tell that I was uncomfortable in a situation going through a deal. Clearly I didn't have all the answers and he was pressing me. And not in a bad way. It was certainly a safe environment. I didn't feel that safe, but it was and. He was just pointing out, like you said, the flaws in the deal, and he stopped when he realized that I was trying to have the perfect answer, and he [00:21:00] said something to the effect of, Hey, I know you don't have the perfect answer.

I'm asking you these questions, and I know they're uncomfortable. If we're gonna win to this, we're gonna win it together and we gotta get the answers. And he pulled out a phrase, he said, the more you sweat in peace, the less you bleed in war. And he's this is a safe environment, is basically what he was saying.

This is peace time when you're out with the customers and the prospects. That's the tough, that's the battle to use. The, to use that type of analogy. So totally get it. You were going somewhere and I cut you off a while back, and you're going toward, you said a lot of salespeople are motivated by money, but that's not, I think what you're saying is that's not the only thing they're motivated by.

Bill, are salespeople only motivated by money? And if not what else drives them?

William Bagshaw: I think we all like to wake up in the morning and feel good about what we're doing with our lives. We want to be able to turn to our wife, our kids, our family, extended family, and feel proud about what we're doing in our lives. [00:22:00] And I guess, if you're making a whole bunch of money, I guess you can hang your hat on that and feel good somewhat, I don't know.

My best days were, sure, when I closed a big deal, but boy, if I had an idea that got embraced by senior leadership, I felt good. I felt great. If I was given a compliment in front of the team, I felt great. I felt self actualized. I felt Hey, I know what I'm doing. I'm in the right job. What a great environment I'm in.

And I think particularly with the senior reps, the Eagles, the top people that financially perform and they do it the right way. And you let those guys and gals run a little bit on their own. Those folks thrive on that kind of feedback from leadership. I'm not just a monkey spinning a wheel.

I'm a human being that is trying to earn a living for my family. And it's important to me that I that I feel successful in what I'm doing. [00:23:00] And I found that if you treat those folks. With the amount of respect that they've earned, boy, the loyalty goes up, and that's an important thing, right?

Attrition is very expensive, particularly if it's your top reps,

Matt Benelli: A

William Bagshaw: Yeah.

so I think that's another important cultural thing to pay attention to. It's an EQ thing. I think it comes naturally to a lot of people, but not everyone.

Matt Benelli: Yeah. Just prospects buy for their reasons on their timelines. So too salespeople come to work for their reasons, not the their manager's reasons or not the company's reasons. So finding out what drives them is super key. And and I think you, you did a great job

William Bagshaw: And everyone's a little different Matt? It's the old Bill Parcells thing. Everyone's a little different. They're, the things that I knew that really mattered to Buckley were a little bit different than the things that I knew mattered to Kim. Some similarities, but, I think that leaders that can tap into that, I know the leaders that I responded to best in my career had a pretty good sense for what moved me.

outside of work. What is Bill all [00:24:00] about? And could somehow, without getting too close, tap into that and develop a bond and a relationship that was powerful for business too.

Matt Benelli: Yeah, they're unlocking that intrinsic motivation, right? They're lighting that fire within each person. So Bill you described in the past I know we talked about your quadrant and some other things, but can you describe the framework at a high level that, that you've used? For coaching salespeople over time.

William Bagshaw: I can. Yeah. And I was taught this early in, in my Oracle career. Honestly, I don't remember whether it was John or Amit. It was one of those two gentlemen.

Matt Benelli: That's okay, bill. 'cause you know what the rule of three is, right? The rule of three is the first time you use take something from somebody. Their idea, you give them credit. And the second time you use it, you say I heard it from somebody. I'm not sure who, but from the third time on, it's yours.

You own it. So you

William Bagshaw: Enough time's gone on it, I probably could own it because I use it a lot and we're talking a long time ago, but, I have a very simple [00:25:00] matrix that I use I, I'm stealing from the Gartner Magic Quadrant approach and on one axis is financial performance, so up here would be top overachiever financially, down here would be underachievement financially, and then the horizontal axis would be behaviors, attitude and, far right would be all the right behaviors, doing it the right way, good team player on the far left would be somebody who's in the extreme toxic.

I don't like to use the word cancer, but toxic. Irrespective of financial performance, a drag on the on the on the organization. And frequently in my management career, I have taken a magic marker and literally drawn that quadrant and asked reps where they think they are. Go put a dot on where you

Matt Benelli: Yeah.

I'm sure they're always, they always nailed it, right? They were always exactly where you thought,

William Bagshaw: So some did some didn't, the most problem, the most problematic scenarios [00:26:00] are the ones where you've got extreme financial performance. Somebody is 150 percent of their Quota, but they're toxic and they're negative on the organization. And they think because they're 150 percent of the number that they, Oh, they put their dot in the far upper right.

Of the quadrant and then hand me the marker and I said, okay this is how you're perceived by your team and by your leadership as well as the surrounding team that you work with, you're actually over here and that can lead to some really it's just a very simple, but yet powerful way to visualize and start a conversation with somebody.

Matt Benelli: And just because there's people listening to this and we don't have the visual up there, but the, that toxic, that problematic situation that you're describing is a top performer. Who is not exhibiting the positive attitude and they're not demonstrating the proper behavior and activity on a daily basis, [00:27:00] and that's what makes that extra

William Bagshaw: everything's a battle, everything's a complaint constantly, and what happens is you've got the folks that are. They're not yet financially performing, but they're doing all the right things, and we believe that person is going to cross over and start attaining financial success, but it's taking a little bit of time.

If they're observing this person that is 150, 200 percent of the number, and all that person does is battle with people, what is negative with people, and complaining etc. That's not the, that's not the behavior that we want to have copied or mimicked, replicated by the new hires that are trying to cross over that line into financial performance.

Matt Benelli: So we could talk a whole, we could do a whole show. We could write a whole book, and books have been written about this exact topic. But let's just, let's cut to the the end on this one. You, let's say you've identified this person and you've brought it to their attention, that [00:28:00] even though their performance is well above average, that their behavior and their attitude is a detriment to the team.

And you've coached them and you've tried and tried, and you've done all the right things, yet it doesn't change the dilemma. And there's a lot of people, there's a lot of new managers, new sales leaders out there that run into this. What do you do? Do you cut this person loose? Ev, and they're 150% of their number.

Do you cut them loose or do you just grin and bear it? Suck it up and deal with it? Mind you again, you've done everything to try to change, to try to change this person. What do you do?

William Bagshaw: So we've already been through the process of the one on one counseling. We've already been through the process of following up with an email or two saying, I just want to reiterate, it's these specific behaviors that are problems, problematic for the

Matt Benelli: You've done all the right moral coaching and all the right checking the HR boxes. You've done everything.

William Bagshaw: My experience is that you then follow it up with a mid year performance [00:29:00] review. I'm making this up, mid year performance review where it gets real. I don't know if it's a five star rating, and they're expecting they're going to be a four or five because they're 150 percent of the number and all of a sudden they're a two because the behaviors that you've asked them to improve upon for The betterment of all it gets real.

And, oftentimes that results in my experiences is they leave they tend to leave,

Matt Benelli: And you have, you had, have you had to do that?

William Bagshaw: for sure

Matt Benelli: what's the impact been on the team? So you cut a top performer loose who, there was a lot of collateral damage. There was broken glass, but everyone knows they got it done. They were going to the club trips, they were making all the money.

What is the, what's the reaction of the team? I.

William Bagshaw: they leave the, I, so I've had a situation like this not that long ago where call and talk to the reps one on one. Hey, just want to make sure we talked about this. I know so and so is an important part of the team. And it was a friend of yours. Oh, Bill. Oh, geez. I, dude, I don't know [00:30:00] how you put up with that.

First off, it all comes out, they all see it. And actually the leaders stock rises with,

Matt Benelli: Yeah.

William Bagshaw: And now. This is not black and white stuff, right? There's a lot of gray in the, in these situations and this is where managers earn their money is sorting through it and making, that's a tough decision, imagine you're a manager and you're behind in your number.

And you're going to cut loose somebody that is your top financial performer because of these behavior. Those are tough decisions and a great opportunity for me as a leader to soundboard with my management chain to make sure I've got checks and balances on this thing. My experience has been that once the individual leaves, everybody opens up and speaks canonically and it was a relief to the organization.

I like it every single

Matt Benelli: Yeah, every single time I, and I echo that sentiment, but I also agree that it's a tough decision to make recognizing the pressures that managers, especially frontline leaders face on a daily [00:31:00] basis. And then on top of that, you have to have the support of senior leadership. 'cause otherwise, I like.

William Bagshaw: What are

you

doing? You're doing your best rep, your best seller.

Matt Benelli: And that's why coaching culture needs to really, cascade from the top down. Really good stuff. Let's pivot just a little bit, bill and learn a little bit more about you. As you mentioned, you've been doing this for a while, right?

You've done a lot of great stuff. You've skinned your knee, stubbed your toe along the way too. Talk a bit about your career journey and its influence on your value system as a sales leader.

William Bagshaw: Oh, boy, that's a big question, Matt. Yeah, sure.

Matt Benelli: I know I've heard a ton of those bag shams, and I've heard people refer to bag shams along the way, so you got those from somewhere, right?

William Bagshaw: So I got out of college, I got into hardware. If you want my career history. My, my first job was basically selling green screen. Mini computer based word [00:32:00] processing systems in a, I didn't know any better. I was young and stupid in a market that had already gone IBM compatible PC with WordPerfect.

So that was a tough way. I learned a lot of hard lessons there mostly around perseverance. But I pivoted into software and worked in what was called the MRP2 industry back then became ERP, Gartner coined ERP for a company that's now part of Infor, a company called Symex, the Sightline product line, and then was over there for about four years and then focused on mid market.

And in the mid 90s, mid late 90s Oracle, SAP, others were starting to move down market into the broader market. It's the Ray Lane term. And I was one of the first reps in the country hired in to to work on that. We're going back to 1997. 96, 97. And I was fortunate that I got brought in and worked for a bunch of really highly competent people that went on to [00:33:00] do big jobs.

Matt Benelli: when you think about that, right? When you think about the, 'cause you had the benefit so when you think about, like you take something from Simex, you take something from Oracle, you take something from Salesforce, you take something from Palo Alto Networks. You think of all the good deals and situations and all the what are couple of things that just really shaped how you view the world as a sales leader?

William Bagshaw: Let me just say this, that one of the things that Keith Block was famous for a quote. I've heard him say it a bunch of times and it's always stuck with me a little bit is and this is even before when he had the big job at Oracle, we were in the same office in Waltham, Mass. Hey, Keith, can you give me some career advice? Sure, Bill. Find a great leader and imitate what they do.

Matt Benelli: Yeah.

William Bagshaw: the hall. Go down the hall. And trust me, they're there, Bill. Go take note, take a mental note of the great things that those people do. And just for a while, while you're getting your sea legs and all that, you're a first time manager and all that just imitate what they do.[00:34:00]

And then you're going to figure out your own style a little bit. And that always stuck with me. And I was I was fortunate, like I said, that I was able to imitate people and the people I'm talking, so I'm going to talk about.

Matt Benelli: Yeah tell. Let's talk a

little bit about it.

like time you were benefited from really good coaching.

William Bagshaw: Oh, gosh. ATOM.

Matt Benelli: No, like where you were going with it, like that's exactly it. Like you worked for some phenomenal people and I think that's what you're, yeah.

William Bagshaw: Yeah, folks that have gone on to have big jobs at other companies, present level, et cetera, et cetera, EVP level. And I, I'm forever grateful for that because it was like going to graduate school for enterprise software selling that I got to. Work for and with a lot of these folks.

And I think a lot of what I've been talking to you about today, honestly, were lessons that I learned from those people. I talked about, I think managing with, psychologically safe environment. I've spoken about creating a culture where. It's psychologically safe and reps feel as though they'll be praised for coming up with new and [00:35:00] inventive ideas and thinking differently.

One thing that I didn't leave out, which certainly was a, that I did leave out, which was a big lesson for me. When I came to Oracle, working for some of those folks was the analytical aspect of the business and really digging into the data and seeing where the data leads you around hypotheses and, fact based decisions that could improve the business.

That was a very big. learning for me early on. I got a heavy dose of that working for a bit, certainly for John as well. And I thrived in that kind of a scenario where I could dig into data and look for trends and analytics and come up with some suggestions based on that. And a lot of that stuff falls into the moving the business forward bucket.

And those gentlemen created an environment where I felt really good. I took pride when I went home at night and feeling like I came up with an idea to help. Move the business forward in a fact based way that was credible. And over time,[00:36:00] if you do that with your leaders you build trust, meaning that the leadership has trust in you as a, as an advisor, as an advisor, and it becomes a two way coaching scenario.

​

William Bagshaw: I'm coaching, but they're also receiving feedback from me. Maybe we won't call it coaching. Maybe we'll call it feedback, but it's very similar. And if you can get into that sort of a dynamic, that build that kind of a culture and retain really good people, like some of the names that I mentioned, boy, a bachelorism, right?

Enterprise software, it's a win rate business. There's just not that many cycles at one time. You have to have a high win rate to be successful in enterprise enterprise software. It's a win rate business.

Matt Benelli: And what did you say before? You said there's a thousand ways to

William Bagshaw: I think there's a thousand, yeah, there's a thousand ways to lose a deal. And there's only one or two paths to get there.

And you [00:37:00] need to hire, attract, hire, enable Motivate, retain the people that are the very best at that. They're the people that I know that what I like to use is, I think when you're working on a deal, a big complex deal, I like to hold up a Rubik's cube and it's every hour you get a new piece of information about your deal and you twist the Rubik's cube and now it looks different and oh my gosh, there's a whole difference.

We just learned some new information. I got to get back in the line with my leadership team in that psychologically safe sandbox because the Rubik's cube just changed from where it was two hours ago. And finding the kind of people that have the mental capability, the aptitude to be able to handle that, right?

How often things change, how complex it can be and fostering an environment where they can thrive in that kind of a scenario served me well. Served me well.

Matt Benelli: A and even, with the Rubik's cube, it's con things are constantly shifting, right? So how do you get to the point where you get it all lined up? And as a [00:38:00] manager, you can't come in and just take the stickers off and put it in, with the way it goes.

You, you have to work together to get there. And it's a slow evolution and you need people that can hang in there, persevere through it. And you talked about feedback. And the feedback, I think is what really helps get that Rubik cube eventually lined up and solved if you will. Great leaders, the best leaders give continuous, actionable feedback, but it's not always.

Construed as positive. Sometimes it's not what you want to hear. Would you agree with that? Like it's sometimes like the feedback is, you're not, I know you're trying really hard, you're working really, you got a lot that you're putting into this, but we might need to look at doing things differently.

What are your thoughts on that?

William Bagshaw: It's a spoonful of medicine. And I think it's around how you deliver. That message, but it's sure, that is an important part of coaching, but I just don't the point I was trying to [00:39:00] make a half hour ago is I don't think that can all just wait to, and I think you're saying the same thing that can't just wait till I beat down a beat down on a forecast call.

Why didn't you do this? You idiot. No. It's upstream from that because you're in constant conversation and dialogue because it's so complex. You're twisting the Rubik's cube. Okay. Hey, man, you really, I'm shocked that you missed this dude. I got to call this out.

Yeah.

What were you thinking?

Where's your head at? That, that kind of a thing.

That's part of the job. That's, that is absolutely part of the sales leadership job, coaching job.

Matt Benelli: And most of the time the best people are the ones who say, oh, I know.

Totally screwed

William Bagshaw: screwed that up. Especially if they know where your heart is. Especially if they know that Bill operates in a psychologically safe... He creates an environment that's safe for me to have blind spots. And yet he's pressing me on this. He's not happy about this. Ooh.

Matt Benelli: Yeah.

William Bagshaw: Yeah. That's not just bluster.

It's not just rhetoric. It's not just [00:40:00] me being a hothead. It's, this is a little different than how the conversations usually go. All I'm trying to say is that when it's time to pull that lever, it's that much more impactful in a good way to help the rep progress his or her skills. And career because I've earned the right to give really honest, impactful feedback that they know I'm just trying to help them, man.

I just want to help.

Matt Benelli: You made the two points that I was gonna use to summarize. You earned the right and they know that you have their back. So coming from the same place like

William Bagshaw: Yeah, I should have said that earlier. I think that's so important. If that the reps know that you have there, but if they feel like you're, that their job's always at risk and people are always playing stump the chump. And it's always a beat down. It's really hard. It really gums up the works around a good relationship with leadership.

Which as we've talked about at [00:41:00] Nauseum is so important to maintaining that win rate in the business that we're in,

Complex selling.

Matt Benelli: A hundred percent. Wow. Bill learned so much today. Servant leadership, how to deal with toxic top performers creating a psychologically safe environment leveraging data to make the best decisions possible out there in the business. Really appreciate the time today and Good.

All right. So we're gonna, we're gonna leave it right there. Bill. Really enjoyed the conversation. Thanks a

William Bagshaw: Thanks Matt for investing your

time.

All right. Good luck out there.

Matt Benelli: and

and to all of you out there. Yeah. Hey, come on out. Come on out. And thanks to all of you out there for listening. If you learn something today, if you laughed a little bit, if you know somebody who would benefit from hearing this or if you have a recommendation on someone who you'd like to hear from on the show please share it.

Please share the link to coach to scale again. Bill, thanks. It's been my pleasure to host this conversation on behalf of Coach to scale, and until next time. [00:42:00] Coach 'em if you want to keep 'em.