Balanced Strategy: Mastering the Art of Zooming In and Out

Jonathan  0:03  

Hey everybody, back again with another fun episode of the strategy gap. Joining us today for the conversation is Lester ang. Lester is a strategy and revenue operations advisor who's led global teams in driving growth transformation work throughout his extensive background in strategy consulting and revenue operations. He spent time leading these global teams as a worldwide Director of Strategic Planning and Operations at Cisco and vice presidents of revenue operations at security scorecard. Prior to that, he's led consulting teams at monitor group, building strategy and operational excellence for Fortune 500 companies. He's passionate about leading large, effective teams and building aligned go to market functions. Lester, welcome to the show. 

Lester 0:46  

Happy to be here. Thank you for having me.

Jonathan  0:51  

Great. Well, certainly going to be in store for a lot of fun conversations today. And to kick things off, I wanted to talk a little bit about kind of the the similarities and sometimes differences between both strategy and revenue operations. And one, I think, particular skill set that's important in both of those is that the individuals are often asked to handle both very broad, 30,000 foot view tasks, but at the same time, those more detailed aspects of the role. From our last chat, when we were catching up. You talked about the concept of really being able to effectively zoom in and zoom out. So to kick things off, I'd love to get your perspective on the importance of this skill set and really how to do that effectively in a role.

Lester  1:33  

Yeah, no, that's a that's a great question. I think, I think a lot of people talk about being able to zoom in, zoom out, see the forest for the freeze, and being able to, you know, at at one look at, look at grand strategy one minute, and then look at tactical initiatives and how that happens, and look at really detailed metrics. I think a lot of the times, people miss the intuition of when you zoom in and zoom out, right? So, you know you could, you know, you guys are clearly very steady, and you every a lot of people have their MBAs and a lot of working experience, but being able to effectively zoom in and zoom out means you need to build an intuition about when you need to be detailed and when the details are going to drag you down. So just to give you a really quick example, earlier on in my career, I was consulting for, you know, the state of Massachusetts, for for one of the cities, and they had an Office of Vital Records. So for those of you who don't know, by Office of Vital Records is where you get your birth and death certificates. Now they had a really peculiar problem in that they have never opened on a Tuesday in a decade. Now it seems like a trivial problem, but if you imagine the number of wasted man hours of people going to the going to the Office of Vital Records to get something on a Tuesday and then have to turn around, multiplied by the number of instances that happens. It cost the city a lot of taxpayer money, so consulting team was called in. My consulting team was called in to try and address the problem and see whether we could get the office open on a Tuesday. The underlying problem, as were told to us, was that there was so much work that within a 40 day week. The existing team could not service all the front end and back end operations, so they had to close on a Tuesday to the public in order to do all the back end stuff. Now, you know, I'm a I had a bunch of freshly mentored MBAs on my team. And you know, when you have a hammer, everything's a nil. So we dived in. We do. We looked at all the processes. We had a bunch of analytics, you know. We brought in best practices, all the heavy artillery, but at the end of the day, none of it really got traction, you know? And the client said, hey, you know, they're still insisting. The team is still insisting that they can't get all the work done without closing a day to the public. So what we did was we zoomed out and we said, hey, what are we actually trying to solve for? You know, we're basically trying to convince a team that, you know, it's really important to open a Tuesday. We need to think out of the box and how we can convince them it was possible. So we did something that we've never done before, which is that we looked at a staggered schedule. Now what this means is that we allowed people with we allowed people to elect what time they could leave and arrive at the office so the people with families would come in really early and knock off early. And the people who are younger people tend to party a lot elected come in later and leave later. Now from that, we effectively pulled out more than a 40 hour work week, hence allowing the office to be open on. Tuesday because we had a larger number of total working hours. So I cite that example because, you know, it's easy to say, hey, now let's look at grand strategy. Now let's look at metrics. Now let's look at what initiatives. But the ability to say, hey, you know, we're kind of spinning in circles here on this level of detail, why don't we just take a step back and try and think out of the box to figure out a different solution that's just maybe sometimes unorthodox. So I think, I think, yes, people talk about the value of zooming in and zooming out, but I think also the ability to have that intuition of when you want to look at the detail and when you should take a step back to, you know, rearrange the pieces on the table. That's that's really important as a strategy. Person, as an revolves. 

Joe  5:52  

Yeah, that's a good point you're making. I mean, Jonathan and I had both had similar experiences by getting our MBAs while we work. So we don't have the experience of doing the two year full time thing, getting hired by one of the big three, and then parachuting in. And, you know, the idea that help is on the way, you guys couldn't figure it out, the help is here. And you know that a lot of times that doesn't work exactly like you'd expect. Yeah, it's all you. And they're like, Yeah, what do you know about our business? You know, we need that Tuesday off. It's definitely so I guess the question I have is, and we'll go back to the point about out of the box thinking, but what techniques have you used in your time to, like, let the people's guard go down a little bit, to say, I understand what this looks like. I understand like I'm somebody coming in and trying to how to you should, how you should run your business, but I really am here to help. I would love for you to understand your issues, and I'm going to bring my solutions to the table and see where we can fit. How have you managed to make that conversation more friendly versus confrontational? Because it can easily be confrontational if they view you as a threat or, even worse, arrogant to the plight that they're experiencing. How have you worked around that in your career?

Lester  6:57  

That's a really that's a really good question. And I would say I encountered that challenge, Joe, not just in consulting, but I also encountered that challenge when I was taking on new leadership roles, right? So often than not, you know, in my career, I've taken on leadership roles where I've come from the outside, and I'm now the leader, and it's from different company I used to do a different way, presumably a quote, unquote better way of doing things, trying to implement something right? And you know, when I'm leading a team of 20 people or 30 people, you're going to have quite a number of them saying, hey, what does this guy know about operating at this scale of business? What does this guy know about our niche of cybersecurity, for example, what does this guy know about how our go to market teams work. You know, everyone likes to think that they have a very unique way of going to the market, right? So I think, I think the question is really great, and I would say, I'm gonna say something really trivial. I do a lot of listening, so I typically don't implement any changes in the first three months. Now, when you're in a startup world, you're expected to be impactful in the first three months, right? So, so what's the gift, right? If, if you're trying to listen and build rapport, if you're trying to build credibility, and if you're trying to build the trust that you understand what you're trying to change, how do you do that and still make effect, make effective groundwork that you are expected to do. And I think, and I think a lot of it is about not making, not making the changes first, but having the conversations that that give people a different way to think about something, right? So in your first three months, you don't have to say, hey, you know, we used to do a comp plans this way. Now we're going to do comp plans a different way. You could say, Hey, have you guys thought about, you know, doing it this way? And in my experience, it's led to this outcome. But I'm also really transparent about these are the instances where it doesn't work. Do you think that this company falls into the instances where this wouldn't be very effective. So allowing people to come to their own conclusions about, you know, a hypothetical outcome you're trying to get to in the first three months is making iterative process, iterative progress, right? So that's one thing I do is, is just listen a lot on the first three months and not make, not implement really concrete changes. And then I think, I think the second thing I would say is understand your people, right? A lot of times robots leaders spend times understanding systems, understanding company, understanding the product, understanding the technology, but they don't understand the people that they're working with. So understanding people's backgrounds and understanding why they think about a certain problem a certain way. You know someone who started that career in sales and then landed in rev ops, versus someone who started in finance and landed in revops, they're probably going to think approach a problem very different way. Um. And so that's really, that's really important to pay attention to. And the other, the third thing I would say is Joe and Jonathan. The one thing I noticed is, as a RAVs analyst, right when you're first starting on your career, you build these skills of being very detail oriented, very quantitative. You need to know the 1000 feet and you need to know the 500 feet. But when you become a people manager, people that you don't, you don't normally apply that detail orientedness to to the people that you're managing. So that's kind of the challenge. When I see revops analysts, right? And I see going to a rev ops manager, going to a rev ops director, going to a revolt Vice President, you most people don't necessarily apply that detail orientedness to to understanding their people, right? So I often joke, hey, you know you've you understand the systems as an IC. Now that you're a manager, you got to understand both the systems and the people you're working with with the same level of of attentiveness. And that's kind of how I see the how people may or may not be successful when they move from nicely role to people leader role.

Jonathan  11:20  

All great information, and certainly agree with a lot of that. One other thing I'll add on top of that, that I found to be helpful throughout my career, both as a people manager and kind of coming in from the outside. And Joe can attest that anybody that's one of our customers that's had us in person for the day, particularly when I was earlier in my career, you're sitting there in a room with executives, and they're looking at you, saying, What are you going to tell me about your my business that I don't already know? And the goal is not just to listen, but sometimes calling a spade a spade is helpful. I would go into rooms and say, Look, I'm not coming in here to tell you what you should and shouldn't do with your business. I'm in here because of this expertise and because of what we've helped other organizations do, or what I've helped other teams do, and to help you navigate through that journey on yourself with all the knowledge that you have. So I think sometimes balancing that listening component with just being honest about what you're actually there for and what you're going to bring to the team, or how you're going to change or not change things, can help out that situation as well.

Lester  12:26  

Yeah no, I think that's a great that's a great point. And one thing I'll add on top of that is, it's okay to be it's okay to be vulnerable, right? So when you're talking to an exec, and like you said, He's looking at you, what can you tell me about my business? I don't already know. You know, one of the things I usually say is, look, I've spent the last eight weeks only looking at this problem, right? So I I've schooled myself in all the angles of looking at this issue. Is that something that you think I've missed in how I've in my analysis, right? So you're not taking away from the fact that they know a lot more about the business overall than you do, but you're kind of you're emphasizing the fact that you focus on this one particular problem for the company, and that's and that's how you know you want to connect with them and say, Yes, I don't know the business overall as well as you do, but here's what I know about this particular issue we're trying to solve, and then it gets it connects better. In my opinion, you have the

Joe  13:29  

idea of being a generalist, a generalist versus a specialist. You're saying that, you know, especially if you're talking to, let's say, a CEO, their job is a lot of times being a generalist. They have a lot of problems that are under their purview. But you're saying, of the 50 problems I was focused on one of 50, and I could give you maybe some insight that you didn't have time to do. So it's not because they weren't thinking about it, or they're incompetent because they didn't fix it, because some people automatically go that place, because they'll say, You think I haven't thought of this? No, no, I know you've thought of it, but you haven't had the time to really dig in deep. And therefore that's what I've been doing the last eight weeks. Do you have some time for me to share my findings, like, exactly positioning it in a way that it's like, you know, not calling them now that, because most people defense is like, you think, we haven't thought about this, and you have to, you have to combat that. So that's, that's a great point you're making. Yeah, yeah, yeah.

Jonathan  14:16  

And certainly, kind of going back to the importance of zooming out versus zooming in. I think one particular area that I see organizations fail with this most acutely is thinking about the overall customer journey, or how they're managing their teams and alignment to what their customers are doing. There's a very natural tendency to say, hey, let's zoom in. Let's figure out all the things that we need to do, or all the things that we need to fix across our marketing team or our sales team or our customer team, none of that actually thinks about the customer and the steps that they don't think about things. Oh, now I'm interacting with a marketing team, or now I'm interacting with a sales team. Let's talk through kind of a mirror perspective when you're mapping out a customer. Journey, because that's been a big part of your career in rev ops. How do you think about the overall customer journey from that 30,000 foot view and then applying the more tactical aspects throughout that journey?

Lester  15:12  

So that’s a great question. So I like to say I'm a recovering consultant, so it comes from a strategy background. So when I first got more and more into rev ops and operational transformation. It bothered me that people were constantly talking about teams and not talking about the actual go to market motions, right? So if you're a rev ops leader, if you're a rev ops leader, particularly in your career, you're probably thinking, does Field Sales have everything they need to be able to go after customers. Does customer success have everything they need to go after the customers. You know, what do we need to do the product teams or processes? Do we have there? You know? What do we need to do with marketing and marketing ops? Do they have all the things they need? Are they interacting with the other teams better? Now, I come from a view where we need to go back to fundamentals and look at land, adopt, expand and renew, right? Because no matter what kind of company you are, your sales motions are going to fall into these four blocks, right? How you acquire a customer, how you get the customer to use more and more of your products in a more meaningful way, how you get your customer to buy more, and how you get them to renew their relationship with you. Now, then you layer the different teams and your tech stack across those verticals, right? So, for example, you might have a tech stack that you know gets settles the first three blocks, and you need a separate one for the fourth one. You might have one that cuts across the fall so you're able to then have a really complete and non overlapping view of whether your go to market is as effective as possible, right? You can layer your comp plans on that framework. If I have a field sales that that's doing, land and expand, right, acquiring customer and upsells do their comp plans actually align with what I need them to do? Right and do, does the tech stack actually cut across the four blocks? So I tend to think of it in the customer customer motion, as opposed to, what platform are we going to use, or is this platform working enough? No, we start with the fundamentals and say, do we have everything we need that covers our fundamental four ways of going to the market. And then we talk about, hey, what? How effective are they? Do they talk to each other. Do our processes work? So that's kind of how I think about it, as a rev ops leader, and that allows me to communicate to the executives as well, because executives don't care if you're using Salesforce or HubSpot, right? They care that, you know, the Rev op team is, is empowering each dollar of sales costs in the most efficient way. And that's, and that's how I tend to look at it. 

Joe  17:58  

You mentioned incentive plans, which makes a lot of sense for folks that are profit centers, right, at least revenue centers, sales teams and whatever customer teams, a lot of times you can incent behavior, because that's just indicative of the role. But with strategic planning and all the other elements that come along with it, you do have a lot of cost centers that also need to do their thing to ensure that the revenue teams can do their thing. So what have you found to be an effective way to incentivize people that maybe aren't used to being incentivized because they don't have a role that looks like that in order to that for them to buy in to maybe an ambitious plan that you put together? Have you had any success with getting everybody rallied around it? You know, if you're a salesperson and you dangle a nice target in front of them to say, you know, if you hit these targets, here's the the riches that you will have bestowed upon you. That's that's easy, but the hard part is maybe somebody in engineering or in a different back office role that is critically important. How do you make them care about the plan as much as maybe somebody who has a sales background?

Lester  18:58  

Yeah, definitely. I think, I think fundamentally, well, even when you're talking about people in non sales and backgrounds, you know, they tend to have performance components of their their complex right now, the weak leak of that is having managers and leaders who are able to in a discretionary in discretionary context, able to assign the right the right levels of remuneration and bonus payments in order to motivate the team right, nothing demotivates a rev ops person more than someone who's not very competent, getting recognized more than themselves putting in all the work. So, you know, yes, you have, fundamentally, you have conversation plans for non commissioned folks that are linked to performance, but you have to make sure you have leaders that are really good in being able to access, assess and administer those plans. The second thing I would say is, which is often overlooked, both on the commission side and the non commissioned side, is, is your. Promotions, right? You know, people often over over, often overlook. Promotions is a tool to reward people who are doing really well. And you know that really extends to both the non commissions and commission side. In some of the companies I worked at, Joe, there is a component that's linked to long term, you know, two year company performance. So particularly at one of the companies I worked at, there was an EBITDA component of the compensation plan, which means that if the long term EBITDA of the company was was trending in a positive way your bonus would be, would be bigger. Obviously, there are downsides to that, because there are people who are very far away from influencing that metric, and yet are still under that non commissioned comp plan. But I think it's a good start to make sure people are all aligned on, you know, especially when you're going through a cost savings exercise like you rightly alluded to, which is, can be very, very painful. And the funny thing is, I've been in situations where, you know, I got the role, and one of the first things I'm asked to do is, hey, our Commission's costs are way too high. We need to find a way to cut it by 40% and objectively it is way too high. You know, when you're on conversation spend like that's maybe 20 22% of of your of the revenue that you're bringing in. It is objectively too high. But how do you tell a sales person that for each dollar that they're going to sell, they're not going to make as much as they did last year. So that's, that's another, that's another interesting problem. It's, it's always the worst situation where you're parachuting in your situation where you feel like you're starting 500 yards behind the starting line, right, because you're trying to fix something and then make it better. But I also think that it's an interesting situation where, if you can be really creative about trying to solve that problem, it's a good opportunity to showcase what you can do.

Joe  22:08  

It's funny, and I'll pass it back to Jonathan, but yeah, nothing gets certain leaders more hot under the collar when they see those commission checks go out. So it's just, it's the cost of doing business, and a lot of organizations have multi year contracts now. So that commission is only typically paid that first year in a lot of businesses. So yes, there is a good upfront cost, but if they're a client for three years, which they signed for, or in perpetuity, because they love you so much, then that commission that was paid out seems negligible, but in the moment gets everybody hot and bothered. That's an easy an easy place for us to get some money back. But in reality, all you're going to do is drive your best sales talent out. And it's a bit short-sighted. 

Lester  22:45  

Yeah, definitely, definitely. I think fundamentally, what you want to do is have comp plans that incentivize high performance, right? And keep them and comp plans that gently encourage people who are not, gently or aggressively encourage people who are not performing to move on to their next role, right? And again, same with, same with Rev ops. And I think this, this incentivizes a high performing Salesforce than seeing a low performing Salesforce get paid the same as they do, right? So we gotta, we gotta be very careful about compensation. Fence,

Jonathan  23:20  

yeah, so I really think, you know, looking at the topics we've covered in this conversation so far, there's so much about it that is, you know, let's, let's listen and make sure we don't just go do a bunch stuff. And that gets to the point where we started things off, and how are you effectively zooming in versus zooming out? So you don't want to zoom in too much and just go in with this list of things that, hey, here's how we're changing your compensation, and then everybody's mad at you and you've ruined the organization. But you also can't just stay in the clouds and talk about things at high level like for better, for worse, sometimes external consultants give off that perception because they're coming in just from the outside. So I love the example you gave earlier on with getting people to come in Tuesdays. But more fundamentally, how do you manage within your role when you zoom in versus when you zoom out and like, what sort of framework can somebody use to best use both of those skills as effectively as possible?

Lester  24:16  

I think I usually start with a hypothesis-driven approach, right? So your question is, how do you build the intuition on when you should be zooming in on the details and when you should be zooming out? Usually what I would do, and this is from back in my days as a consultant, is to go around and ask, What do you think is the biggest reason something like a change like this would fail? Or what do you think is the biggest reason something like this will succeed? And then I start to hear things that tell me what is the weakest link in making something happen, right? So just to give you a really quick example, when I was working at Cisco, what. Of the things we were trying to do was to get partners to sell more software and get and have a bigger partner led motion, right? So when I asked around and said, Ask around the different people on the ground, the one thing I kept hearing was price point. What is the price point that partners will be excited about, but not to give away the farm. So in that instance, I knew that price and how we sold to partners was the thing that I needed to zoom in on right, because that was the link that pulled that reading together. Right? I don't need to be very concerned about how we're messaging to partners, because partners have their own messaging to their customers, right? I don't need to be really concerned about the product, right? Because the product, it's a five, six year trajectory, but because I've had all those conversations and all that knowledge, I build an intuition about what is the weakest link, that something may or may not be successful. And so I think that's, that's the first thing on how you do that. Intuition is to talk to as many people as possible and say, Hey, I really want a candid opinion, or why you think this is a really stupid idea, or why this hasn't worked in the last five or six years. You know, just in other words, what is the reason it hasn't worked until now? So if you really understand that from if you are really understand that fully, then it tells you when the details that you need to pay attention to and the details that you don't really need to focus a lot about, because, you know, in a certain way, things are taking care of themselves. In those other areas,

Joe  26:41  

a lot of sense, and the idea of it didn't work before, so it's not gonna work now, that sometimes it's the truth, but sometimes it isn't. It really depends on a lot of things, because you might have tried it two years ago with a different product market fit a different set of priorities, a different budget. The concept of revisiting old ideas is not a bad thing, and I know that I fall victim like, Well, we tried that already. Well, tried it with different people, different people, different budgets, different time, different market. That's, I think, a helpful message for people to to learn. As I pass it back to Jonathan to close this out, because we're we'd go on for hours.

Jonathan  27:12  

Definitely. Yeah, yeah, absolutely. So Les, I know you spent a lot of times throughout your career advising organizations and leaders and now advising companies. But our final question, if you had to go back and give yourself a piece of advice starting your career in strategy and rev ops, what advice would you give to yourself?

Lester  27:32  

I would say worry less about being right. And I think people who go into rev ops are highly analytical, highly quantitative. That's a great thing. But how, when you, how you communicate something, when you communicate it, it's, it's really important, right? But I say that at the same time as never lose, never lose that logical bent, because that's what you bring to the table, right? You're not the one on the golf course shaking hands and closing the deal. You're the mechanic trying to figure out why this car is not working right. So don't lose that logical, linear reasoning bent. Don't lose that quantitative and call things out as they are, but also figure out when and how you communicate something and put effort into those things, right? You know, we always say, understand your weakness, because you need to pay more attention to them, but also spend a lot of time amplifying your strengths so that they over overpower your weaknesses, right? So I think as a as a rebels person myself. I'm naturally quantitative, I'm naturally logical. I really do call a spade a spade, and I'll hit you with it. But I also want to be able to be conscious of how I communicate that. So I think that's, that's one advice I would, I would give myself.

Jonathan  29:03  

Yeah, I think certainly in strategy and operations, people are so close to the work that they feel like I've done this research I have to be right, and maybe you still are right, but proving to that you're right is not ultimately going to be the way to get to the outcome that you want at the end of the day. Yeah. Well, perfect. Well, Lester, it was a great conversation today. Thanks for joining us on the show and looking forward to catching up soon in the future.

Lester  29:26  

Yeah. Thank you. Thanks. Jonathan, Thanks, Joe, it was really nice chatting with you guys.

Joe  29:31  

Thank you, sir. Thank you.