Why Strategy Fails to Reach the Front Lines w/Mohsin Syed

Brian Dietmeyer: Foreign. Welcome to another episode of Closed Mode, the Enterprise Sales Show. I'm Brian Dietmeyer, CEO of Closest Strong, the home of precision guided selling. And today I'm really, uh, honestly excited to be here with Mohsen Syed, who's the president and Chief Startup Officer at kiwitech. If you're not familiar with kiwitech, uh, I find it a fascinating business. Uh, they not only build engineering solutions for startups, but they also invest in what's next. Uh, and Mohsin's also been an enterprise sales leader, so welcome to the show, Brian.

Mohsin Syed: Thank you so much. It's a pleasure. Uh, I've been really looking forward to this conversation since we met about almost like a month ago in Miami. So excited, uh, to do this. Let's get it cracking.

Brian Dietmeyer: So, yeah, you're right, we did meet and we were having some coffee and uh, and our conversation was what you, uh, I believe termed the, uh, kind uh, of a new category, the strategy to tactics layer. And for those who are listening to this, and we're having this discussion that companies pour billions into sales strategy. You know, new messaging, new product priorities, go to market initiatives, but very little shows up at the deal level. And I liked this notion of the strategy to tactically, tactics layer is the connective tissue sort of between strategy, leadership, intent and frontline execution. So it's been a frustration for people in the past. And the whole dialogue you and I were having is with technology now, like, we can do that. It's not optional. We can make a connection between what leaders want people doing and actual behavior change and application at the deal level. So let me, let me start with a question for you. Um, you know, and the crux of our discussion was, you know, why does strategy, uh, fail to reach the front lines and get executed? So why do you think that is? Why do we have a difficult time saying, here's where we want to go, but we need behavior change to make it happen?

Mohsin Syed: No, thanks, Brian. It's, uh, a great question, but let me kind of like step back for the benefit of listeners. Give a little bit context about where my viewpoints come from. Right. We all are built and, you know, uh, molded by the experiences that we have. Um, so, uh, a big part of my career has been in enterprise sales leadership. Over the last 25 years, specifically the last 15 years at Kivi Tech, I've been working with, you know, founders, revenue leaders across US Europe, you know, uh, GCC and the wider APAC markets. And I think what I feel. And again, a lot of these opinions Are personally my observations of what I've seen. And, but I think the most fascinating thing that I've observed is almost no company fails because they lack strategy. You know, uh, what I feel is they fail because strategy collapses. Because, you know, like when a moment a deal becomes real, you know, we tend to always look at strategy living in leadership, off sites, in decks, in memos. But if you look at it from a sales standpoint and from running sales teams, execution lives right inside live opportunities, in calls, in your emails, in your proposal reviews. Right. And the problem is there's usually nothing connecting the two. So I believe that the gap between intent and action is where those sales win rates flatten, forecast break, and reps default to whatever they feel convenient. Right. So I think that's where I feel why strategy fails to translate into real outcomes for business is because strategy is kind of designed for alignment, you know, it's not for action. You know, and because, uh, and I think a lot of things I take as a leadership, part of the leadership team responsible for it. Because I think for years we've been answering questions like who are we targeting, what's a priority, how do we compete? Right. But if you look at your sales teams on the other end, they're answering a very different question every day. And that question is pretty simple too. What do I do next in this particular deal? Right. So you see the difference when the leadership is kind of like looking at, you know, like you're still in the parking lot of the building and here the, the sales reps are actually on a live play wanting to know how do I go for the next three or five yards? You know, so I think that's the basic difference. Right. And so, um, and I think there's also very few systems that are out there that translate that strategy into stage specific, deal specific guidance. And what ends up happening is then reps revert to habits. And if someone has bad habits or does not have, well, you know, grounded habits, then, you know, deals break, you know, not because they don't care, but if you look at it, speed beats Jerry when the coda is on the line, right?

Brian Dietmeyer: Yeah, yeah. You know, my friend mentor Jim Dickey, who is the founder of chief Sales Officer Insights, he said to me, you know, about a year ago that, you know, we have sko, we announce, who knows, a new product, a new solution, a new suite, and we do that over the weekend. And then on Monday, all the reps go back and sell the same thing they were selling on Friday. And customers are asking to buy the same thing they bought on Friday. So you called it the connective tissue, which I really like. The other thing that you said was this notion of, uh, stage specific actions, right? So if you are, and you and I chatted a little bit about this, it's sort of like if we have this new thing we want to do or sell, well, what does a qualified opportunity look like? Who do we need to be talking to? What kind of discovery do we need to be doing? You know, how does this change our competitive mindset now? And I think like getting into the weeds a little bit on that, that's kind of how you translate that down. And I'm wondering if you could expound a little bit, just uh, go back to your stage specific thing if you want to add anything to what I just said. Because I think making this tangible for folks who are listening is, is really important.

Mohsin Syed: Now I have the uh, I think fortune of working both from an enterprise in a large deal transaction standpoint to small and medium, right? So let's look at two scenarios right now. When you're talking about a deal specific or a state specific, um, situation today, a lot of those sales decisions in the enterprise world is a matrix of a lot of complex personalities that are dealing with things, right? So you have the cxo, so you have the CEO, CEO, you know, who's got a whole bunch of stakeholders that he's reporting to. You got your CFOs, you know, who are entrusted with the top line, bottom line demands, right? And then you have a cio, a ciso, and then there's, there's, so there's a variety of complex, I would say, personalities, uh, you know, aspirations, all trying to, at times, sometimes they don't work in the, in the interest of the organization itself. Collectively, right? Individually, they all probably are doing a fantastic job. But sometimes they're not aligned because each one is sometimes incentivized or dissentivized to do things the other way around in that system. To go and sell and create that alignment is very, very tough. So what you really then need is at that particular stage who you're dealing with. It doesn't really matter who you've been speaking to, right? You now as a sales team, uh, have to understand at that stage where the real, you know, who's really holding the ball, right? And sometimes it's the special teams that win, you know, and you just cannot overlook that fact. It's sometimes that specific, you know, director in finance who had some issues in his past life with that type of a deal that brings in and kind of completely blocks the deal. So I think that's what I believe that systems and processes need to be there to be able to navigate the teams to take control of such scenarios. Right now if you look at the small and medium enterprises, like, you know, like where you're dealing with one or two decision makers right now, that calls for a completely different matrix. You cannot make it over complicated. You just have to go with, I uh, think from a decision making standpoint it's rather simple, but it's also pretty quick, a binary thing. You don't have the luxury and the liberty to draw, you know, like a six point plan.

Brian Dietmeyer: Right.

Mohsin Syed: It's just like you're there at the register. You got to get him, um, to buy it now and then also ensure that he's buying it or you know, she is buying it in the interest of the business outcomes, what they tend to achieve. So I think the situations have become much more complicated because it's not easy to go from dealing with these different types of customer behavior, different type of stakeholders, and the power struggle is real. How do you handle a human element? It's not just about value creation, value matching, value mapping. Now I think you got to have much better, you know, uh, psychiatric skills, you know, than real sales training skills. You know, all of it doesn't.

Brian Dietmeyer: Well, so yeah, two quick things. One, we've talked about this, that sales training is how to sell. And when we talk about this connective tissue, the strategy, the tactics layer, it's how to execute your strategy. And that might sound like something basic, but to me it's a fundamental shift from we're teaching reps how to sell versus we're teaching reps how to execute our strategy. And in the T up and a moment ago you talked about systems, uh, and processes for this connective tissue. Um, and we also said it's no longer optional given the technologies that are out there. What do you think the role of technology is in this connective tissue now? Especially AI, of course.

Mohsin Syed: Right. We will also look a little bit about what has been there with us over the last few years and then, uh, and then kind of like you know, step uh, into the whole AI thing. Right?

Brian Dietmeyer: Yeah.

Mohsin Syed: And I believe a lot of issues or failures is because of that. This whole thing being a systems issue. Right. Because strategy according to me is very periodic. You have quarterly reports, annual reports, but execution is something that you're doing continuous cycle. Right. It's daily, it's hourly. Right. And again, that's the failure. Right. Because what has happened is the technology solutions that we've been using in the past, you know, CRMs, big fan of it, they track activity, uh, the sales enablement tools, they deliver content, coaching helps, but it doesn't scale across every rep and every deal. Right. So now what you're seeing is strategy pretty much will decay as soon as volume and complexity increase. Right. And I think that's where I feel the role of AI is going to help all of these organizations who are going to adopt it. Because I believe AI, uh, is the inflection point because it allows now strategy to become more contextual instead of static. Instead of telling reps what the strategy is, you can guide them on how a particular strategy applies to this deal at this stage, against this competitor. And I think that's the real breakthrough, that one to one in context guidance delivered at scale. I think that's the power of AI and I'm a big, big proponent of it because I think what AI can really do is it can quietly guide your next best actions inside those live opportunities. Now you basically taking strategy which is just kind of like, which has always been this aspirational element to making it more operational. And that's what I think. I'm excited by platforms, even platform like Pro Strong, which one of the things I love about it is that it embeds strategy directly into deal execution, not generic data. And now you have the leadership intent translated into actions and that gives everyone in the team a winning recipe to deal with.

Brian Dietmeyer: Yeah, you make me think of uh, uh, a podcast I did a while back, uh, with uh, someone who, I read his book several years ago. Frank Cispadis is a Harvard professor and he wrote, he was writing about this years ago about his book is entitled. One of his books is Aligning Strategy and Sales. And I think he was, he was talking about it long before we were. And it's interesting when I, when I did the podcast he said, you know, when he wrote that book he had to lay out all kinds of like huge human processes to do that. And as we started talking about what you just said about AI, he's like that connective tissue is there now. So I wonder, uh, uh, just on to the next question. Uh, I'm seeing strategy change kind uh, of faster than ever. Right. Uh, used to be annual planning and VP of sales told me that we do the equivalent of annual planning quarterly because everything's changing in the market so quickly. What are you seeing and how do you think that impacts the need for this connected issue?

Mohsin Syed: And you know, as much as we, uh, we could debate about it. I think that's the new reality of business, um, strategy, strategic changes happening monthly, even weekly. Right. Because there's so much that's going around the world that honestly a lot of things are beyond our control, beyond even the controls of boardrooms. Right. Uh, it definitely overwhelms the front line. Right. And I don't think reps as such resist strategy. You know, I think they're drowning in them. They have new ICPs, new messaging, new priorities, and they all get layered on top of active deals that are already pursuing it. Right. So what I think we require is a system that can dynamically adapt execution to actions so that reps don't just by fault, you know, default to what they feel safe about it. Right. Um, and I think that's what I think what we need is the faster strategy cycles without execution support will actually reduce deal quality, even when the strategy itself is right. So I think from that standpoint, I think we're dealing with this pace of strategic changes. And I think that's where I think factors like, or, uh, uh, technology solutions like AI can actually play a much better role in helping us process ton of information, ton of changes. Right. And then contextualize to something that we could implement within the teams almost on a daily basis. Right. I think that breaking down of huge volume of data, information insights today is possible because of data, uh, because of AI. And I think that's what I believe AI would help immensely in terms of helping not just with the, with the volume and the amount of data that we have to deal with, but also the pace at which this data keeps changing. Right. So I think that's, I think AI is that answer to that changing what

Brian Dietmeyer: comes to mind as you're saying it is like, all right, we've got our current strategy shifting. We want to be pushing this now and not this other thing or, uh, we want to be selling more upstream. And so we've got our current strategy, we've got a deal we're working on, and we've got a stage we're at. And when you talk about contextual, what comes to mind is this notion of just in time that, uh, is what we need. Here's my strategy, here's the deal, here's the stage I'm at. How do I connect this? Right now I'm getting ready to go do discovery. What should I be looking for?

Mohsin Syed: Right.

Brian Dietmeyer: So what do you think the, uh, impact will be of this if companies can get good at this? I read a stat a while back that um, these numbers are directionally accurate, but something like 50% of strategies are actually executed and then 90% of them don't deliver on the financial promise or the revenue promise of the strategy. And so I guess I'm leading the witness a little bit here. But yeah, in your sense, if companies figure this out, why, why should I do this? What's in it for me?

Mohsin Syed: I think you got to look at three critical things, um, that will change immediately if you start getting this right. And I'm a big believer always that put the team, um, first. So we'll go with the team. Right. I think the team stops guessing, the reps will execute with confidence, which I think is the most important thing. And that's what I wanted every day when I come to my team meetings is just taking the guesswork out of your, in our workflow, in our out of your deal flow. Right. Let's execute with confidence. Let's execute with the information that we have. Let's execute with the tools and processes that we have in place. Right, right. I think that guesswork, taking that out collectively as a team, I think when confidence is in, it's a different song and dance. Right. Second, I believe that, you know, we all talk about, you, uh, know, trainings and coaching and all of that. It's very, very important. And I think what we really need is managers. And when it's done well, managers coaching decisions, not just outcomes, you know, and it's going to have a significant impact on business results if managers start doing that. Right. Uh, because everybody understands what is need to be achieved, you know, but what uh, is someone going to do to achieve that? That's what I think the real coaching is, you know, And I think that's where some of the best managers, best coaches that are out there, they coach decision, the process of why you have to take this particular decision, this particular step, not just worry about the outcomes. And I think that's very, very important. And I think you will see a lot of that happening well within your teams. Third, I believe leadership gains much real time visibility into deal quality and execution risk, not just forecast. We've been just like more consumers of trending reports. Right. Uh, I think what this will potentially do, if it's done well, they will know exactly, you know, what the deals are there on the table, which are the qualitative ones, and what are the risks involved in it. So I think as a leader then you are now pretty much kind of reverse engineering your strategy based on the actual execution outcomes that you and your teams are achieving out there, there. Because I think when strategy gets embedded into every deal, not just at a very organization level, I think revenue becomes more predictable and which I think is a huge factor right now for so many businesses because a lot of businesses are suffering from the unpredictability of their revenue streams, of their revenue numbers. Right. And it's not because people, you know, start to work in a much more harder or smarter. But I just believe that the systems are aligned. You know, when you get all of these things done. Right.

Brian Dietmeyer: Yeah. A couple of things come to mind when you're saying that it's not only the revenue and of course it's the revenue, it's also deal quality. Like we want deals that are in alignment with our desired strategy. And so I think it's both of those. It's like the right revenue. The other thing you said, Mohsen, that I love is this idea, uh, when I add to this idea of reps stopping guessing and I think if we give them insight to strategy. Your role now as a rep is not to sell stuff. Your role is to execute the company's strategy. And you talked about confidence and that. I think this is a cool role for the reps. And I'm just wondering how you feel about that.

Mohsin Syed: No, I mean, I think it changes their perspective, right? It changes their perspective of them just not being traders and transactionists. Right. It tells them they are building something of value both for their organization and for the clients that they are interacting with. Now those reps will just go a long way in not just creating trust with the clients because you're going to stand out in that crowd of sales reps that these clients are going to look at. Right. Someone who almost feels that, you know what, I met this guy, man. Like he was just not a sales guy. He had a very clear vision of what that organization was doing, you know, what that organization stood for. Now it almost gets into think, I wish I had a sales rep like that. And that's when you close the deal. Yeah, the moment when, I mean sales, I mean, there's nothing I would say inspiring than a sales guy who sounds like a real sales guy, but leaves the impression that I want that guy in my team. Right. That's when you really stand out. And that's when I think you, you kind of provide merit to the craft, if I have to say that. Right. Because I think, I think today the leadership is getting it right. I think, uh, and also the execution layer is getting it right. They do respect leadership strategy. Right. And the leaders have to respect frontline reality. I think that, that, that, that, that equilibrium of respect from leadership and people are executing on the front line. I think that's that. I think that that respect and equilibrium needs, uh, to be established. I think that can only be done if they are powerfully integrated with systems that both sides can communicate, both sides can trust, and both sides can work together with. It's not siloed. And I think companies who will invest in that layer, I don't think they would just sell better, but I think they will build trust in their numbers, their teams, in their decisions. And I think that's where the real competitive advantage lives.

Brian Dietmeyer: Yeah, it's interesting too, because when you connect, uh, we're doing some work with the company now where we're kind of making this connection. And part of the company's strategy is to conserve capital. They've made a lot of investments. And so giving the reps access to that's part of this strategy. It creates a dialogue where one of the reps pushed back and said, all right, I want to make an investment in this renewal to expand it. And the strategy was, we're not making investments, but the rep was aware of it because AI was able to say, hey, that's out of sync with your company strategy. And what that resulted in was dialogue with management about is this right in this instance. And to me, that was just so cool to see that discussion between a rep and senior leaders about, hey, I'm gonna push back on this, um, capital strategy we have. So I want to end with something kind of street level. Um, do you believe that sales, uh, enablement and training are keeping pace with, with what reps need now, or is that part of the gap

Mohsin Syed: now? I mean, look, I don't want to sound excessively negative, but a lot of sales enablement, uh, has failed, but they haven't really failed. I think it's the problem of not evolving to the changing times in the changing business scenarios. Right. Um, a lot of training methodologies out there, they just can't keep up with dynamic selling. Uh, because today, even if you look at a lot of conventional, you know, low tech businesses have an excessive technology integrated layer, even if they don't see it on the front end, that's happening. Right. Like a lot of training does not account for that. Right. So I feel the future isn't more content or training content or more dashboards. I think the future is more precision guided execution delivered in the flow of work now. And I think that's where, again, it's important for people to, for both the leadership, the strategist and the people who are executing to come together and understand that what I really need help with and that getting translated into those enablement tools, practices and training methodologies rather than trading them something on a concept or on a process or on some kind of a tactics or a strategy that they don't even appreciate, you know. So I think um, and I think that's what I think we need to do. It's got to be more dynamic, it's got to be more inclusive. Uh, and then I think there is that um, you know, top down has always been the way I think we need it to be much more re engineered so that these sales reps feel that from an enablement and training standpoint they are receiving what they really need and where they need to get better at.

Brian Dietmeyer: Yeah. I'll kind of sum up our in person chat a month ago and again today like what I keep hearing from you is this strategy to tactics, connect, contextualize and stage based like get it out of the PowerPoint and out of the clouds which uh, I love. And that message continues to resonate with me. So you've been super generous with uh, your time and your ideas, prepping for this and executing it today. And I think of this closed mode show is kind of a body of knowledge for those of us who live in this space. Right. So um, our peers can come and listen to other peers. So you've added to that greatly especially on a kind of a new idea. So I really appreciate all of that now.

Mohsin Syed: Thank you Brad. I think you know, like look, sales is something that we all human beings do in some format, professionally, personally, you know, selling to yourself, you know, uh, at the end of the day, you know, or at the beginning of the day, you know, like why do I need to show up to work? You know is part of a sales process internally that you have to deal with. And I think that's where I think it's very important that ah, I think where I feel technology AI could help us immensely is to integrate and invest in those systems. As organizations are evolving, look um, at systems that can fairly bridge the gap between strategy and execution. Uh, I don't think it's something that needs to be left um to a few experts. I think it's about or bringing in external experts. It's just bringing in systems and processes and creating that connecting tissue. Right. And if that's there and if companies start investing in it, ah, first of all acknowledging that things have to change, I uh, think it'll be a great way to see how people, as they say, are not called just sales guys. They all are strategic ambassadors and. And strategic, uh, messengers of the company and its services. And I think that's what we all love to see in the near future.

Brian Dietmeyer: Yep. No, I love that notion of acknowledging it as an issue. And I feel like we're starting the conversation about what we call this emerging category in this new layer. And, yeah, you've added a great deal of depth to it, and I really appreciate that. Awesome.

Mohsin Syed: Brian. Thank you so much for having me. It was fantastic. Uh, much better than I expected it to be.