The Zen of Strategic Execution w/Tim Ohai

[00:00:03] That's awesome. Hello and welcome to another episode of CloseMode, The Enterprise Sales Show. I'm Brian Dietmeier, CEO of CloseStrong. And today I'm super lucky to be here with my friend and associate Tim Ohai of Kupu Solutions. And Tim is also the author of The Zen of Strategic Execution, which is what we're going to be talking about today. Welcome to the show, Tim. Hey, Aloha, Brian. So good to be here. Thank you.

[00:00:30] So lucky man living in Hawaii, by the way, for those of you who aren't aware. So you and I, I will stipulate to the fact we've had a lot of discussions. We're both interested in strategy execution. So today, and I know you're the Zen of Strategic Execution is broad strategy. Today we're going to zero in a little bit on sales strategy, if that's okay. Absolutely. I imagine it's similar premises.

[00:01:00] So I want to start with this. I know that your book's been getting a lot of play. I think you're in the bestseller list, and it's written well. I have it on my Kindle. Thank you. But I also wonder how much is sort of market realities right now, this interest in strategic execution? I think it's right down the middle of it. Part of the reason that, let's be blunt, I've, this book's been quote written in my head for years, years and years.

[00:01:25] And actually it started because of all the work I was doing originally in sales strategy. And I found that the number one obstacle to a sales strategy was not the strategy or the customer. It was our own internal companies and the strategy they had that was getting in the way of trying to generate revenue. So that's how, that's kind of my genesis, how I got into this. We can talk about that later. But I was just interviewed earlier this morning with somebody who asked me about, you know, when do you think everything changed?

[00:01:53] And I go, I honestly think it's been a problem for Evers, but COVID accelerated our awareness. COVID changed all the rules. COVID exposed it better, better. It didn't change all the rules. It exposed all the broken ones we had. Yeah. And because it exposed so much, people are like, oh my gosh, we have to be on cloud, et cetera. But also it changed the rules as we evolved coming out of it.

[00:02:14] And then we are now in this sense of, do you know the book, the concept of resulting by Annie Duke, the world series of poker champion who's a behavioral economist? No. So she is an economist rather. She, she took a concept from poker and applies it to business. And it's so critical to our discussion today, especially around sales. And it's this idea of resulting.

[00:02:40] Resulting says, if I go to Vegas and I, I don't play poker much at all, but if I show up at a blackjack table and I make money that first night, I'm, I'm actually good at blackjack. I must be good at this thing. I'm a natural. Yes. So my results say, oh, go back. I go back the next night. I lose everything. And now I'm pulling out my debit card and getting more cash or whatever. And now, oh, I suck at blackjack. I'm horrible at this thing. Right. You have no idea if you're good or not good at blackjack.

[00:03:10] If you're only looking at the results, the key is the thinking that goes into producing the results, the decision making. We've been resulting for years and I'll be blunt sales. Sales, sales is one of the worst. Sales is classic. If the numbers are good, we're good. If the numbers are not, we're not. And it's, we all know that we've all been there. The numbers are important, but they don't tell the whole story.

[00:03:33] So this struggle now, as it's harder and harder to hit numbers, everybody's realizing, holy crap, we just can't assume the numbers are going to be there because they've been there. How do we produce numbers? And I think that's opening the door to this idea of execution is like, how do we execute our strategy? And yet, the most common question I ask leaders is how often were you formally taught how to execute strategy? The response is almost always never. Right.

[00:04:03] Yeah, it's funny. I did a post a few months back on execution and I got a LinkedIn message from a CEO of a tech company saying, were you in my meeting last week? Oh my gosh. And so that's why I ask you, like, it's not only you, like I'm talking a lot about this and it seems to be out there. So, you know, my friend and advisor, Jim Dickey, who some of you may know, he said to me once, he and I were talking about this about 18 months ago. And he said, you know, here's the thing.

[00:04:30] Sales and revenue leaders spend months developing their, their strategy. They then go to SKO over the weekend and they announced the strategy. They might do a little training. They might roll out some playbooks. And he said on Monday, sellers go back to selling the same way they sold on Friday and buyers go back to buying the same thing they were buying on Friday. And, and so what, here's my question for you. Why, why is that behavior change so hard? We need humans to do something different on Monday, but they're not doing it.

[00:04:56] Well, let's go back to let's, let's, let's take a moment and do a little intellectual work and define the word execution. So my journey launched when I finally heard Henry Mintzberg's definition of strategy. Strategy is not a plan to achieve a targeted outcome. It's a series of decisions to achieve a targeted outcome. Okay.

[00:05:20] So if we can agree that strategy is a decision making discipline, like nothing ever goes according to plan. Then we have to believe that so is execution. Execution is a decision making discipline. And so all the work we put into SKOs, all the work we put into decks, all the work in training and all the key account strategies and all the other stuff. Are we building an environment of great decision making, or are we giving people plans to go hopefully follow which they're not because reality is going to hit.

[00:05:50] And, and it's, it's that tension of I have to deliver a result. Your plan is not going to get me there. Let me just do what I know. And I'll, I'll, I'll do my best to deliver the result. And if I do give me a bonus check. And if I don't be, be kind. Yeah. Yeah. No, it's, I, I love the notion of decision making by the way, because it's there, there are decisions in the moment of truth to do something that's in, that's in alignment with strategy.

[00:06:15] But having been someone who taught decision making for a while, like data and insight helps people make better decisions. So it's like we get down into the weeds about do, yeah, we set the strategic direction, but do they really have what they need to make those decisions? So I, I recently came across, I was doing a bunch of research on this topic and two things jumped out to me.

[00:06:39] One is that HBR said 67% of strategy fails to be executed. Okay. So we kind of know that's out there. Forbes said 95% of employees don't understand the strategy, I guess, which is kind of in line with what we were just talking about. And I'm just wondering about your reaction to those two stats. I know them both. Well, let me go to the 95% one. Yeah. That's from Kaplan and Norton, who are legends in the world of business.

[00:07:09] And they found it wasn't just 95% don't understand, or the actual research says they don't understand or even aware of the strategy. And, and I take that and go if 95%, and they did a more recent study in Australia where they gave people a multiple choice test and said, which one of these is our strategy? And still over 70% of the people got it wrong.

[00:07:35] And so what's happening and I, and I go one step further. Why is it not translating? Because I believe the strategy is there. Why is it not translating out to the rest of the organization? And, and I go with a principle. It's been around for forever, but it's, and I'm going to tie it back into our opening theme. The idea here is in the absence of information, we invent our own. When, when I don't have the information, I'll just make it up. Yeah. I will. And that's why, you know, data is so important.

[00:08:02] If I can give you real data, real information, I'm going to eliminate that gap. But not only do I have a gap to fill, if I don't have that information, if I'm in survival mode, if I'm in this pressure zone, I'm now going to not only invent information, I'm going to make it negative or critical. Because that's what the brain does. Then when the brain is in survival mode, it starts seeing everything as a threat. It's scanning for threats.

[00:08:28] So now I'm going to invent and inject negativity and criticism into the information I'm making up. And now I'm going to go execute against that. So all the decisions I make are because, oh, leaders don't understand. My boss is clueless. That customer is stupid. Pick, pick any excuse you want to come up with. They're almost all negative. It's not, it's not driven by empathy. It's driven by necessity. And that necessity is like, how do I get out of this thing alive?

[00:08:55] I think I just heard some of your industrial psychology master's degree come out. A little bit, a little bit. No, it's cool. It's interesting to me. And I think you're right. You know, I often wonder too, like you look at, especially again, sales strategies, like you can lay out the whole thing. But for me, and I want your opinion on this. There's an issue of, I think this goes back to, do they understand? So there's this broader strategy, but then there's an issue of what do I own?

[00:09:26] Because, you know, the sales and revenue leaders might be coming up with a strategy, but I can't impact all that as a frontline rep. But what pieces of it, right? What, what pieces of it drop directly in my lap? Yeah. So I, when I'm, when I'm coming this, what I call bottom up versus top down, it all anchors on this idea of clarity.

[00:09:45] And if I remove clarity, if I don't, if I don't give you a clear scope of disruption, clear sense of priorities, and make sure that we have goals and roles aligned, I will destroy everything else you're doing. It will, it'll wreck. Honestly, you can remove clarity out of any situation, driving to a friend's birthday party and never into their house before. If I take clarity away, the whole thing's going to go sideways.

[00:10:09] So when I want to ask for clarity, I literally ask, the first question I ask is what's our scope of disruption this quarter? Are we generating disruption or are we minimizing it? Are we, are we trying to make things crazy because you're okay with, I don't care how clean it is. Just get it done. Yeah. That's, that's effectiveness. Or do you want me to, you know, dot my I's and cross my T's and put everything in the CRM because you want more efficiency and we're trying to eliminate friction. What we don't want is no answer.

[00:10:39] Because if I have to put everything in the CRM, but it's a complete waste of time, it doesn't work. And now I've got friction and you want me to hit my numbers and you want me to do all these other things that are not necessarily going to be recorded in this year. And because it doesn't even ask, I'm going to make up my own answer to that question. And then I will prioritize accordingly because if I don't have clarity on the scope of disruption, my priorities will reflect whatever I think the answer is. Yeah. And then you tell me I have a different priority. Doesn't make sense. I reject it.

[00:11:08] So I always ask what's the scope of disruption. And if my leader doesn't know, I asked them to go ask or make up their own answer. Well, then fine. What do you want to do for this region? You know, maybe I'm in the Midwest. I'm like, this is what are we doing this quarter? What are we doing that? And it's, I get it. The goalposts can move. We can change. But I got to get clarity on that. And then I follow right up what's priority one, two and three. And tell me what those are in order so that if I say no to something, it's because I've got one, two and three work to do. Yeah.

[00:11:37] And if I'm doing one, two and three, and if one, two and three are good, now I can take on the extra request. But if you have leaders who don't have clarity on the scope of disruption and don't protect those priorities, in other words, everything's a priority, therefore nothing is. Don't expect me to be aligned on goals and roles. It's just not going to happen. Yeah. Yeah. It's funny too. I keep two things. I keep going back to what you said in the, in the beginning about, you know, have, have you been trained to do this?

[00:12:04] You know, and it's just like, almost everything we talk about goes back to that. So I'm paraphrasing, but one of the things you say in the book is that sort of the test of, of effective execution is decisions made when you're not in the room. And, and what I thought about when I read that I worked for Marriott hotels for many years. And there was a group of us sitting, sitting in a room one day, and we're trying to decide to yank the flag off of several franchisees. And because they weren't hitting associate satisfaction, get satisfaction numbers.

[00:12:32] But the problem was millions and millions and millions of franchise fees associated with yanking those flags. Bill Marriott happened to walk in the room and kind of, of course we all saluted. And, but he was sort of like, what are you guys working on? And we told him and, and in his draw, if you've ever heard him speak, he said, every decision you guys make is a deposit into or withdrawal from brand equity.

[00:12:55] And he walked out of the room and we yanked the flags. It was, it was quite easy, but that struck me, he was in the room, but that piece of his strategy, which is brand equity is everything came alive in that moment. So the question is like, how do we get sellers? We're not in the room when they're selling, how do we get them to make decisions in alignment with strategy?

[00:13:19] Well, now we're back into, you know, what's the role of a leader and the role of a leader is to not just make people follow a plan, not even to create a plan. And let me back up. Plans are good there, but they're, but they're worthless. According to Dwight Eisenhower, he literally said, plans are worthless. Planning is great. Planning is important. It's thinking through being prepared, but in the moment, man, Charlie, Mike complete the mission, do what needs to be done.

[00:13:44] So I always challenge leaders. Like, are you building an environment of great decision-making? And they go, oh yes. I go, well, tell me how you're doing it. And then it falls apart, either silence or bad answers. So the first thing I do is give them clarity and then give them empowerment. So clarity, we talked about the three big rocks, you know, scope of disruption priorities. And then of course, goal and role alignment. But then when we get into empowerment, one of the most important things that we can do is proactive backup planning.

[00:14:09] When I talk to leaders and I'll ask the room, are there any veterans in the room? And there may be veterans on this, on the listing to this conversation right now. I'll ask, were you ever given a mission that didn't have a backup plan? Yeah. And the answer is no, never. Matter of fact, we may have had more than one. And I go, why? Well, because nothing ever goes according to plan. You know, you, when you engage the enemy or whatever you're supposed to be doing, you've got to be prepared for the obstacle.

[00:14:35] And then I flip, I go, civilians in the room. How many of you always give a proactive backup plan to your people before you send them out to go do the job? Crickets. Yeah. Yeah. Crickets. So you're not being strategic. So sales leaders can do this immediately. When someone comes to you and says, here's what I want to do. Great. Let's talk about them. You're going to have a big meeting with the targeted custom account.

[00:14:58] People are going to be in the room. What are you going to do if so-and-so doesn't show up? What are you going to do if they start asking about this other problem? What are you going to do if they're just not engaging? Let's talk that through up front. Let's figure out what's the most realistic risk that we've got to be prepared for. Let's talk it through now. And if you're, and if you want to turn it into a coaching moment, tell your player, you tell me what you think we should do.

[00:15:22] And if it sounds good, I approve. Do not go into that meeting without already having that backup plan ready to go or tackle your quarter with your strategy without already knowing here's what's going to happen if, so that you don't have to wait for me to be available to either join the call or answer your question or solve.

[00:15:43] They said, no, what do I do now? And now I can't talk to you for another two days because I'm offside at another meeting. Now I'm wasting 48 hours to respond to something that they could have easily responded to within six.

[00:15:54] Yeah. Yeah. So, uh, it, it wouldn't be a podcast if we didn't talk about AI. So we're going to, I was fortunate enough to have, uh, uh, someone that I respect a lot, uh, as a teacher and a writer, Frank Cispedes, uh, Harvard lecturer who wrote a book called Aligning Strategy and Sales many years ago.

[00:16:15] Right. And we're just kind of really talking about this today, but it's interesting that as he and I, and by the way, if you're interested in this subject and you go to the, the closed mode media website, you can search for this one. But it was interesting because Frank, Frank made a point that, uh, cause I asked him, there was so much human intervention with him for Aligning Strategy and Sales.

[00:16:36] And, and after the show, I asked him, but, but now there's, there's AI, you know, and, and he reflected immediately on that and said, yeah, when the book is written, it wasn't really there. So that's the question, like what role, especially with sales strategy, what role can it play in, in, in getting the frontline to execute? So we're, we're into, and this is a really important thing. We're into orchestration and it's a word that's not used enough. Everybody talks about governance. Great.

[00:17:06] Governance is the rules that you're going to have for how your AI gets used. And then everybody immediately jumps into application. Well, how are we going to use it? I go, orchestration is that middleware that says, okay, if these are the rules, this is how we're going to use the AI. And it's everything from automation to co-creation. And to be blunt, I have different governance rules for how things are automated and automatically done versus how things are co-created with me in the moment. And, and there's, I talk about enhancement.

[00:17:35] Then there's also curation where I just, I just make sure it's, it's happening the way it's supposed to. But let's be clear about what we're asking the AI to do first. Are we asking it to just run independently and be fully automatic? Or are we going to curate that? Because that means I have a different job to do. And if, and if it's something like just send, send out leads, just replace my SDR, just get that.

[00:18:00] And there are some amazing stories of these AI SDRs that are doing a great job of generating leads. But they're, they're, they're more, I don't want to call them fiction, but they're not as common as, as we think, because they're only reflecting the decision-making that we told it to copy. So if my decision-making environment as the, as the host company is broken, and now I'm taking the human out of the loop.

[00:18:26] And I'm letting the SDR digitally copy what I told it to do, but I didn't inject really good decision-making. It's not going to make good decisions on its own. It doesn't have that capacity. It's going to accelerate the chaos. Yeah. So I go back into what is the use of the AI and then where can it help me as a human? If I got stuff that I can automate, let it do it. Great. Done. Just start combing the internet, look, doing research for me. Just here's the, here's the accounts I'm looking for. Look for targeted.

[00:18:56] Here's my profile. Here's my ICP. Go tell me, give me stuff that I can look at. Summarize that information. Highlight it for me. Cool. Automate all that. But now, now I want to start sending out contact. I need to curate that. I don't need to automate that. I need to observe. I need to check it and make sure it's good until it's good enough. Then I can move it into the automation box. Then there's the enhanced stuff. I'm, I'm building a deck, a custom deck for a client. And I really need to make sure it hits all my main points and it does it in a really creative way. Enhance what I'm doing. Give me extra information.

[00:19:26] I, I, like I literally had a conversation with very, very large construction company and I let AI do some research for me. And it gave me some really solid information on waste and rework in the construction industry. I said, how do we factor this into the dialogue? Boom. It enhanced my presentation and it turned into a really rich discussion with that prospect. Well, you, you, this enhanced piece, you, you, you, I think you, you just hit on kind of where I was going. You were talking about using it to create this really cool deck.

[00:19:55] If the AI is smart enough and it understands your strategy, couldn't it create your deck in context of the strategy? That's kind of where I was going. Like, is there a way to link strategy to sales? Yeah. Over time. But from, to go from here to there, you can hear everything I just said. There's a lot of complexity in moving parts. Yes. So we cannot, it's not software. We just flip a switch. We have to go through this, this dip.

[00:20:18] We have to go through this experience of letting it fail and not do well at a small enough scale before we can expect it to ramp up. And, and I've been, for example, working with a couple of different AIs, ChatGPT and Claude, and I've got them now able to, to represent me in coaching advice. I'm like, Ooh, this is fun. This is, this is good. And it saves me a lot of time to write up long coaching advisements for clients. But that took literally years to get there.

[00:20:47] Most companies are not implementing AI with a multi-year strategy to get it to quote arrive two years later. So I want to close with this one, sort of a takeaway. So you are revenue or sales or enablement lead, and you're trying to get these humans to do things differently in alignment with your strategy. Now just more deals, but better deals.

[00:21:11] What are one or two things they could do tomorrow that might have some impact on, on getting this stuff executed? Yeah. Yeah. So almost everything that I'm going to have to spend time on is a result of some sort of conflict and decision-making. So there's two things I would say you can do right off the bat without having to become an expert in execution. Number one, if, if there's an interpersonal conflict or there's a problem with the process isn't working the way it's supposed to, or they want to change it or whatever.

[00:21:41] And even with roles not aligning, people are undoing, redoing, or simply not doing the decisions that need to be made. Start with asking, what's your definition of success? What's your definition of, what's the, what's the outcome? How are you going to measure that? And what are all your requirements? You'll be shocked. I've had senior national sales leaders take that one question to marketing, to ops, to enablement, to HR, to legal, find any group and say, what's your definition of success?

[00:22:11] And, and a, they often don't necessarily have a clear one. They're, they're under stress mode and they're just trying to, I thought this was important. Let's talk it through. Or they have one and it's just so different than what that sales leader is trying to get. Right. So you can't talk about a problem until you've solidly identified it. And now once you get that on the table, it's like, oh, see my definition, my outcome is different. I, my, I define success as this, this, this, I'm measuring it this way. And these are my requirements.

[00:22:42] Now, now we can figure that out, which opens the door to what I call clean escalations. And the key here is everybody knows the escalations. They're typically dirty. And by dirty, I mean, I'm going to go to my boss. I'm going to complain about that person. I'm going to say, they suck. They're in my way. Can you lean on them? Can you, you know, pound the table or something and get them out of the way so I can get my deal done. Clean escalations say, I'm going to go to the person that I'm struggling to make a decision with and say, look, we're not aligned.

[00:23:11] I want to figure out what is right, not who is right. I want to, I want to get this thing. So we're making the best decision for the company, for everybody involved. It's clear our definitions of success may not be aligned, or maybe they are aligned, but how we want to do this is wrong. I literally had a situation like this with a company I used to work actually at. And we were trying to get clarity around the definition of customer journey. And their definition, candidly, was bought from some consulting house and it was crap.

[00:23:39] It was overly simplified and wasn't helping generate leads. It wasn't helping close deals. It was actually way too vague. But that person was like, we paid for this. This is important. I'm like, whatever. So let's do a clean escalation. Like, well, what does that mean? I go, you and I will co-create a deck in a shared drive. We'll put all of my points. We'll put all of your points together. And it's not, we're not, we want to do this fully transparent. So we both know what the other is saying and it's pros and cons, not I'm right. You're wrong.

[00:24:07] It's just pros and cons of each perspective. And then in our situation, both of our bosses were the ones involved in making the decisions. So we pulled both of them into a meeting. We didn't go to one and then the other. We didn't have separate, separate channels. It was one conversation here that here's the view of this, here's the view of that. What do we do? They had never, those two leaders had never talked about this that way. So it was the first time they'd even talked about, oh my gosh, maybe our definition of customer journey is wrong because it affected all of our go-to-market strategy if we didn't get it right.

[00:24:37] Secondly, they talked it through and the conclusion was, Tim, you're right. Your definition of journey is way more accurate, but we've got all this baked into what's currently existing. It's going to take us time to undo that. So can we back off of the pressure of doing something now, but we will start moving in that direction going forward. Great. That's what is right. So if I can get clarity on the definition of success and find out where we have conflicts, we're not pursuing the same outcome.

[00:25:04] And then when we find those conflicts, let's do clean escalations. Let's do this together. Let's make it a shared deck. We both, nobody's hiding. Nobody's got gotchas. We're putting it out and then we'll get one conversation with the right leader and let's just figure it out. And if those leaders can't agree, just do the whole thing over with one level up. And you'd be shocked at how that will clean up decision-making and all the other dominoes that'll fall off of that by those two things. Yeah.

[00:25:32] Well, I have to say mahalo for your time, for your ideas, for your energy, and for writing the book. Again, we're both interested in this subject and I think there needs to be more focus on it. So I appreciate all of that. Well, I will say thank you very much. And one of the most common bits of feedback I'm getting is, A, the book is really good, but also if you're going to read any book on strategic execution, this is the one to read.

[00:25:59] And with that, thank you, sir. Aloha. Mahalo.