Balancing Short-Term Gains with Long-Term Growth Strategies with Dayna Williams

Hi, I'm Warren Zenna, founder and CEO of the CRO Collective and welcome to the CRO Spotlight podcast. This show is focused exclusively on the success of Chief Revenue Officers. Each week we have an open, frank and freeform conversation with top experts in the revenue space about the CRO role and its critical impact on B2 businesses. This podcast is the place to be for CROs, sales and marketing leaders who aspire to become CROs and founders who are looking to appoint a CRO or want to support their CRO to succeed. Thanks for listening. Now let's go mix it up. Hello, welcome to this episode of the CRO Spotlight podcast. This is Warren Zen. I'm the founder of the CRO Collective and I'm very excited today to welcome our guest, Dana Williams. Dana is the author of the Diligence Fix and she is currently the CXO of the Myers Briggs Company. And Dana and I met at a conference and she co co led with me the CRO of the Year awards. And we just talking and talking and talking and it was amazing. Like I listening to her book thesis, I'm like, oh my God, this is like amazing. It's like exactly what I'm talking about. And whenever I meet anybody that has a similar, if not, you know, exact philosophy as I do, I'm like, I almost like want to hug them, you know, because there's not many. And so I really, it's great. So Dana, welcome and really thanks for being here today. So I want to talk a bit about not only the book you wrote, but more the reasoning behind it. Right. The philosophy behind it. Because as you and I decided to do this together is because we realized, wow, we think as long we think alike here, you know, and your book is really evokes a lot of what I'm trying to say in my work. So if you don't mind, please, just a little background on yourself, you know, how you ended up at Myers Briggs, what you're doing beforehand and you know, what inspired you to advocate the philosophy that you do and what prompted this and a little bit more about the work that you're doing from your authorship perspective.

Sure, yeah. So for 20 years I had amazing access to CEOs, CROs, VPs of sales, and it was always under the guise of there's a problem in our organization and the right fix for us is training. And so I was really brought in to unpack. Well, what are those challenges and what do you want people to do better as a result of this training? But I was very curious and I couldn't stop there. And so I always really dug into root cause issues and I had stacks and stacks of notebooks. After two decades of these conversations and, and I'm somebody who recognizes patterns and during 2020 we all had a little extra time on our hands. And so I cracked those notebooks back open and I was really curious to understand what did these situations have in common. Whether it was a startup, whether it was a Fortune 1000, whether it was anything in between. What caused these business leaders to reach out and express their issues and concerns and seek trust training. I was also coming off of my own internal leadership role at a company called Caliper. And it was a 30 year old independent company. We prepped it for sale, it sold prematurely and once again I had, you know, some time on my hands. And while I was reflecting back and there was some wins to savor there, I also asked myself, why was it so hard? Why was slogging our way through selling and solutioning, why was it so hard? So I put it all together. I wrote a first draft. It was a bit of a rant. And then two more drafts really I think came up with what the philosophy was and that the bottom line was when striving for revenue, quarter after quarter, year after year, becomes the way you do business. If you do not do the infrastructure building that's required to have a stable, growth ready, fully aligned organization, you will see cracks in your operational structure and, and those cracks will eventually give way and it won't be pretty.

Yep. Well, I obviously agree completely and I like the way that you put it. You know, I think we're calling same thing with a different term. You're, you're referring to the sort of endless and almost mindless pursuit of revenue, top line revenue as like the kind of day to day. It's almost like a shark.

Right.

Never stops eating.

Right?

Yeah.

And I do see a lot of, particularly the SAS industry has created this sort of monster.

Right.

This is a, these are companies whose revenue models are such that they need to do that to fulfill on the ways in which they've evaluated the, the business model.

Right.

Is we have to get a certain amount of customers in the door on a regular basis or else we won't hit the numbers that we projected, which I know you and I both agree are probably a lot of them are phantoms anyway. But it's like I look at it as a short termism. It's like I'm looking at the world from a. It's not even quarterly. I think it Used to be quarterly, now it's like almost monthly, maybe even weekly. Much, much the same way that we've changed the way that people look at the stock market.

Right.

I mean, I think that if you look back 25 years ago, I'll probably go back far. You know, people looked at the stock market in very large, almost, you know, geological shifts, you know, whereas now it's like every minute of the day the market shifts. And you know, it's almost like I remember that great funny scene from Airplane when the news changes and this reporters have to run back and forth from each phone booth to make the phone calls to their offices to try and get on top of the story. And it's like they're just running frantically back and forth trying to keep on top of a moving thing that, you know, it's preposterous because they're never going to really be on top of anything. And I think that that's sort of the way that I view companies and you're. We obviously also agree that, that not only is that a mindless pursuit, in a lot of ways I think it creates burnout. You know, it also, it takes the focus off of the purpose of the company which is like what are we trying to serve here? What are we trying to accomplish for our clients and our customers? And lastly is it also ignores critically important aspects of the business that need to be in place for those things to work anyway. It's sort of a weirdly, kind of a myopically self destructive pursuit.

Right.

So how do we get here? Like why, why does this happen and what do you think is underlying this and is it something that people are aware of?

I think they're aware of it. I talk a lot in the book about the three T's, territory, targets and tracking. I mean that tends to dominate. So while we'll bring in a CRO and we'll talk a good game around alignment, you know, oftentimes I, I don't know if this has been sort of your experience, but oftentimes these folks are filled by roles or people went up the typical succession ladder of regional director, VP of sales, svp, and then they make their way up to CRO and they're comfortable in territory, targets and tracking. And now they're this sort of big role where they really are responsible for the full go to market. But they're not specialists in marketing. They, they're not necessarily compensation or incentive experts. They don't understand enablement. Oftentimes they don't understand human behavior and what it takes for learning to stick. And yet they find themselves atop of this go to market, sort of end to end machine. And then you add onto that the average tenure of a CRO. I mean, they're in one door, in the door, one moment, out the next step. Sometimes even before a company's like fully documented sales life cycle. Right? Like if you have a sales cycle that's 24 months and you're letting go of your CRO after 15 months, I mean, that's not necessarily fair either. So I think there's a lot of challenges that go into that question of how did we get here? But I think people are moving a million miles an hour. CEOs are beholden to their boards, their PE firms, their shareholders, and they don't take time to sit back, peel the onion and say, what is really perpetuating this constant cycle?

Yeah, well, 100%. And I agree that in when that pocket of what you just said, you know, the old adage, you know, follow the money, right. And I say this somewhat trepidatiously because I'm a capitalist, you know, I'm an entrepreneur. So I have no issue with people making money. It's fine. And I like to see people make a lot of money. I think it's good all around, so that's fine. But I also see that the pursuit of it has inherent problems that, you know, when you have an organization like. And again, I don't mean to sort of negate the entire community, but, you know, the engine in the engine of business is funding, right? That's how money is made, is by funding those businesses. Some people do it organically because they might have had a windfall or they had some cash or they decided to forego VC funding and they went to friends and family. But there's somebody somewhere, somehow, that has to give you the seed money to start your business. I'm in that situation myself right now. And so that that becomes another very critical element in the way that your business is now going to be designed. Because if I'm taking money from an investment firm, particularly the way that they've matured, those investment firms have established and codified methodologies and ways in which they manage their portfolios that they feel have done a lot of kicking on the tires for many, many, many decades, that this is how it works and we're sticking to it, and this is how we manage our companies. And if we're going to give you money, then you sort of have to fit into the way that we manage our companies because, you know, there's no special children in the house. You know, everyone eats the same food. You know, we put it on the table. You know, that's how it goes. Everybody does the dishes. And so even though you may have a different idea, we have a lot of companies to manage. And so we have to manage our companies in a very specific way. It gives us a way to manage our procedures and processes. And those come with things that may sometimes not have much to do with the customer at all. You know, they're very much driven by, like you said, and some of these things are logical, but you're not illogical. If I, if I'm running a, or managing a portfolio of companies, it makes perfect sense that a metric that would be easy for me to measure would be how many customers these companies are closing on a weekly quarterly basis. Sure, that's certainly reasonable. And it's not to say that they're not sophisticated enough that they understand that those customers need to be serviced and that the company has to be in a position to fulfill on what they're promising. But many times, you know, you could fudge those numbers. If I like the numbers and I like the amount of customers are closing, maybe delivery isn't as important now because, you know, those numbers indicate my ability to go get more funding.

Right.

It's attractive to somebody else. That metric is one that very attractive. And so, you know, as long as I, you know, maybe a bit being bit harsh here, as long as the funding organizations continue to manage their portfolios this way, there's going to be some degree to which this has been codified in the way businesses are being run. So my question to you is like, do you see a awakening or a shift in the way funding organizations are changing this model? They recognize that the way that they're running things, while it may be successful for three to four of their 20 portfolio companies, which might be a windfall for them, for the other eight or ten, it's not right. So what are your thoughts on how the funding community is looking at this?

I'm not seeing a shift yet. I still see a mindset of, you know, that three to five year burn. What do we need to do to prop this up just enough to get out of this what we expected? And, and I see sort of a, sort of like a tendency to again, change out, leaders do the optics of what's required to seem like we're taking action. But this work that you and I are talking about, the necessary peeling back of the onion to understand where it's broken in the go to market system where the friction is. Where are we misaligned. I find that companies may bring in consultants from time to time to help them speed up an evaluation like that. The consultant pokes around, they present a 300 page deck, we write a check, that's the end of it. You know, who's going to spend two to three years to actually oversee the implementation of those recommendations? By the time we do that, you know, again, maybe we have new owners or, you know, maybe the market has shifted under our feet or maybe the competitor landscape has taken on, you know, more entrance. Bottom line is there is no shortcut and silver bullet to turning these things around. And yet from an investor perspective that trickles down to C suite and below, that's still the world that people are operating in. They want quick, they want fast, they want shortcuts. And that's why I wrote in the diligence fix that you can't paper over gaping holes and call it a day.

You can't. So what let's assume then, because I largely agree with you, let's assume then that this is the case. This is sort of like the weather report. You know, it's going to snow and there's nothing we can do about it. What is it then that a CRO or a CEO can do, knowing that this is the environment that they're going to be brought into. So instead of it seeming like all kind of gloom and doom, like, okay, well, I guess there's nothing we can do about it. So the little apathetic, you know, attitude is, you know, kind of pervades what? Okay, so look at more different. Like you just got hired as a CXO at Myers Briggs. Right. We'll talk about that a bit. So what's your point of view on knowing these things? And again, the company may not be in the same exact situation that we're describing, but what might be your, I don't want to say advice, but your point of view on what new hired chief revenue officers can do when they know that they're going to be entered into an environment where the expectations are going to be very short term. They can have a very difficult time making and implementing longer term strategies, but they know they have to.

Yeah.

What are your thoughts on that?

I'll share sort of maybe a surprising philosophy that I have. Sure. But then I'd also love to hear from you because you're having these conversations every day.

I'm sure I am.

I think we have to learn from each other, right?

No doubt, no doubt.

So I am 60 days in. At this point, heading towards 60 days in, it's a legacy company. It's got a beloved brand, and it's, you know, it's got healthy top line. But of course, there are. There are challenges. All of the things that I mentioned to you from sort of complicated processes, friction points, competitors. We've got the classics, right?

Yep.

I'm going in and I'm doing a balance of what I'm calling inventory and identify. Just taking a bit of a consultant approach. Right. Trying to wrap my head around where are the challenges, but also trying to ensure that I don't drown in them. And that's key, I think, as a. As a new leader or as a leader that's taken the helm at, you know, the go to market level, you have to know just enough to be dangerous and keep moving at first so you don't get sucked in and lose the view of the forest from the individual tree. So that's number one. Number two, I am focused very much on simplification as a strategy. I think that the more that businesses mature or the more people that get added in the form of, like, sort of bloating departments, there is this tendency to be territorial, to. To sort of protect, create a moat around, you know, your group or your team, operate on an island, obscure the facts, etc. The key is, is to create that environment where people are free, fully sharing where the challenges are, and then inviting them in this subtraction journey of saying, what can we do if we were to drop off 20, 30, 40% of what we require today to make it easier for the customer to do business with us and invite them into that journey and sort of state simplification as the operating principle for the revenue team. And you'll be amazed what sort of comes out of the woodwork. But I'd love to hear from you.

Yeah, yeah, it's great. I echo that. I think the general thing I'm hearing you, if I may just kind of reiterate what I heard is first is an analysis, which I think is obviously that we all need to do in your role. We got to come in and get a lay of the land. I would emphasize that I think the superficial lay of the land is like shaking everybody's hand and getting everybody's names and reading some materials and things like that and looking at a couple reports. And I don't want to imply that, you know, people do that, but I do think that there's a difference between a diagnostic and, like a deep dive.

Right.

And I think that The. The issue I'm seeing is there's two parts to that. Let's stick with that piece of it, because I agree that that's critical is this is one, there's the competency of the analysis is, you know, someone coming into the role as a chief revenue officer. Let's use that as the entry point. What is that particular person's not only competency in analyzing and evaluating their environments, but two is do they have the right playbook of questions they need to ask and the things to look for? Because sometimes, you know, you don't look under the right rocks or you don't open the right drawers because you don't know that you're supposed to. And so you don't. And, you know, there's like a whole bunch of stuff hidden in there. Like, oh, my God, I didn't even think about that. So it needs to be some sort of codified way in which. Here are the checklist of things. No different than if I bring my car into the shop. You know, there's probably some basic list of things that any good mechanic knows to. To look at before they bring your car back out again. And a good mechanic knows that all those things aren't a bad one. Leaves out three of them because they weren't aware of it. That's the first thing. And then the second part is you have to have the. When I said in. Well, there's four things that I think incoming CxO CRO needs. There's authority, autonomy, resources, and Runway. Okay, so the authority should be established during the interview process, right? Where you're talking to the people that are hiring you, you're saying, okay, so here are the things I need to do. Am I able to do them? Do you give me the authority to do these things?

Right?

Am I going to have to go to you, to my principal's office every 20 seconds shit that I have to get filled out for me to do things that I know I need to do, that I just need to be given the authority to be able to execute on. And then the autonomy is different than authority. It's, you know, things change, things shift. Right? So if I have the autonomy to shift and make decisions, then I know that I can make those decisions because I'm giving the autonomy to make calls like balls and strikes of sorts. And that my. For the most part. Right, for the most part, that my authority will be trusted.

Right?

That I'll make mistakes. I'll step. I'll raise my hand and say it, but I have the autonomy to act, okay? And then the resources I need, you know, people and money, right? So that I can do the things I need to do. I need the right talent. I need the right access to budget so that I can get things done. And then there's the hardest one, which is the Runway, which is I need time. And this is where the problem is. So the problem is that I know what to do. I got the authority, got the autonomy. But you gave me three months to do something that's going to take me six. So, you know, I can't speed things up because certain things just take time. You know, we. We do. My agency does organic marketing, and I tell people, you know, I can't make Google index your stuff faster. You know, I think what my. My partner says to our clients, things like, if. If I get nine elephants pregnant, I'm not gonna. They're not gonna have a baby faster. It still takes them. The gestation periods, this is long. And so, you know, that's a reality. And I think this is the part that I think is the. Is the area where the problem is, is that the thoroughness of that analysis falls short 95% of the time, because even if the person knows what to do, they don't have the Runway to do it. And so they don't. And they end up doing a superficial analysis, which doesn't provide, like you said, the ability to identify inefficiencies or, you know, friction points or leaks or process issues or whatever they may be that need to be fixed and addressed. And so they get glossed over and they get carried on to the next quarter, and they never get fixed. So, you know, just to kind of, I guess, answer your question back to me, which is my. My point of view and this is 100%, you're correct. And when you get into the. When you take the job, this is sort of an interesting thing, I think, like the CMO role. Let's use an example. The chief marketing officer role is one that's been around long enough that there's a lot of codification in the way the role is deployed. That if I come in as a marketing person, it's probably a lot of latitude I'm given to get things done because people have an awareness of just how long certain things need to get done. I can't. You can't change it, Right? So there's a degree of allowance that's baked into that role in terms of how long things can happen. There isn't that much that sit with the CRO role isn't that interesting. It's fascinating, right? And so it ends up happening is I make these requests like, are you kidding me? Say, well, you know, like if you knew what to do, you'd understand that that's what is needed. I can't change it. It's not like I'm not asking this for you because it's an arbitrary thing. I'm telling you that this is how much time this is going to take. And if you want me to succeed on the goals that you've prescribed for my role, then this is what's required. And if you're not willing to do that, it doesn't matter who you hire. None of them are going to be good at this job because it's not. That's not a capability issue, it's a allowability issue. It's a organizational issue. And so you sort of have to be almost like an advisor of sorts when you're getting hired for these jobs to know how to get the company to adhere to what's required for the job. Because they don't know. They don't really know.

It requires education. And so I like to your point, I love the comparison to the CMO role. You know, a CMO walks into a job because they stand on the shoulders of others who have educated the C suite shareholders, the board, etc. For decades on what it takes to make these things happen. And I think that, you know, CRO role is relatively new. Right. In the sense of that, you know, organizations appreciate this need for like an orchestra conductor to bring all these people together harmoniously to create a seamless end to end go to market experience. But the inner workings of that is not something that your average leader, board member, shareholder could articulate if put on the spot. And that creates the education delta. And we have to do it. And I frequently say this to our, our friends in enablement because they tend to take on more volume, more water and they don't educate on what it takes to make these things happen. And then after a certain period of time, they just run out of time.

Yep.

And so speak up, educate, advise all the things you just mentioned so that people have a greater appreciation and provide you the Runway and allowability that's required. Because if you don't, what's the, what is the consequence? You know, you'll basically be shown the door.

Exactly. You will be showing the door and it'll be your fault. Right, right. Which it's crazy. And so this is what I hear like a lot of times my clients that I'm working With they call me, and it's almost. It's crazy. Same story. It's like, I don't know what happened. You know, I came in, I know exactly how to do this. And then they just wouldn't let me. And I gave as much as I could to them to understand why, and they finally just got exasperated and they let me go. And, you know, in some cases, I have the. I'm afforded the ability to speak to their former bosses. And they go, that guy was a complete idiot. You know, it's like, well, no, he was actually right. You know, you, you know, it wasn't him. It was. In fact, it was. You guys didn't really sort of understand that what it was he was asking for was, you know, there's a lot of counterintuitive to this. So I, I equate a lot of this stuff to diets for some reason, because diets are very similar.

I love that analogy.

You know, and so, you know, if you're. If you're, you know, if you're telling somebody like, you know, to eat a certain way, that just seems completely counterintuitive to. To what is right. But, you know, it works. It takes a long time for somebody's brain to go, okay, fine, I'm going to do that. You know, I. I went to one of those. One of those racetracks. There's one in Vegas. You can get into the cars that are literally race cars and you can drive them around track. And it's not a circular track, you know, it's a track with. With like a lot of turns and stuff. It's almost, almost like a. It's not. You're not obviously not in, you know, you know, those, the super speed cars. But there's F1 cars. They're not that. It's just a. It's a. It's a fast. They're fast machines and there's a lot of turns. And what they do is, is the first time you go out, you sit with a driver and you're driving, but they're next to you and they're telling you things. They're like, okay, so here's how you increase your time around the track. And one of the things that you learn this is if you'll indulge me, I'm making a point. I am. Is you have to go faster into the turns, which is the exact opposite. The way your brain has been trained to drive, you slow down when you go around a turn. I mean, you don't even think about it. Now your foot goes on the brake or your foot comes off the gas when you go around a turn. You don't speed up when you go around a turn, but that's because you're not driving for the same purpose. If I'm trying to go fast around the track, there's a way that the car is designed that if you go fast around the turn a certain way, you actually increase the friction that's going to take place when you turn. And it's impossible for the brain to understand that in one time around the track. You have to go around a lot of times before. You know, experienced race drivers understand like their brains change. They get, they have, there's, there's, there's pedestrian driving, which is me driving around the neighborhood, and then there's me race car driving. They're not the same thing. And so, you know, if you're trying to teach somebody something that their brain is not yet acclimated to, particularly if there's an organizational structure around that other way of thinking, you're going to sound like a crackpot or maybe someone who's just like, why would we trust this person? Like, why should I take this person's advice on something that seems completely counterintuitive the way we operate? So you sort of have to create some credibility. You have to come into the conversation with a lot of depth in the way in which you articulate things. You have to have evidence to show why you're saying makes sense. You have to present yourself very confidently and you have to have a plan and you have to be able to show like how this doesn't work in such a way that you can change hearts and minds around the main people who are going to be in a decision making position to say, I think you're wrong. Because if you can't do that, you're likely going to end up compromising in some way. And you can be put in a position where you're going to get a little bit of what you want, but not enough to make it work. And you know, it's the sort of thing where if you don't have the full amount of opportunity, you're not going to be successful. You know, and I'm seeing this with three of my clients right now who successfully negotiated the role as a CRO and they got buy in around the whole idea of CRO revenue leadership and the whole thing. And now as three, four, five months are in, everyone's having anxiety, everyone's losing their minds because they're accustomed to similarly like taking those fast turns around the Track revenue's supposed to coming in at a certain pace right now, but it's not right. And I have. He has to constantly go back and reassure. But this is what's happening, this is what's good. It's a different thing you should be measuring. I'm not suggesting that we shouldn't get new customers. I'm suggesting we should just get them differently. And the reason is because if I'm looking at this two years out, this is going to pay off for us two years out in ways that are going to be exponential. It just isn't going to satisfy you right now. So you sort of have to change the way you look at things. That's really, really, really hard to get a organization to think differently. So it's almost better to come into an organization when it is younger, when it hasn't established that sort of thinking yet. And like your situation, I can imagine with a legacy company like yours, it's probably not easy to get an organization that's been doing things a certain way. And I suspect they hired you. I think, I hope because they're ready for that new thinking. They want Dana to come in and give us this sort of new perspective because we've sort of exasperated ourselves and we're ready now to think differently. And I think I'm assuming that that's hopeful that's the case because I know successful. So good. Why do you think it is?

Well, and one thing I want to just tag on to what you just said, particularly in the new CROs that you're mentioning that are four or five months in and people are asking, well, what about the revenue? Hopefully in those cases there was more sort of data behind the decision to bring those folks in. For example, if it's just about growing top line revenue, we. Well, that is going to be a bit of a chore. You know, like you said, that's the ticker, right? We're watching the stock market every day versus zooming out and looking at 5, 10, 15 year yields. Bottom line is, you know, you want to say to yourself, is it a churn issue? Are we losing customers? Is there a net promoter score issue? Right. Because those are some of the things that can be err.