56. Your Strategy is a Work of Fiction
About this episode:
Original Air Date: September 7, 2026Once a year a small group goes offsite, argues for three days, and comes back with a deck. Goals get written. Functions map their OKRs to the slides. Then the market moves, and everybody spends the next eleven months executing against assumptions that stopped being true in February. Most people in the building read that document and can't find themselves anywhere in it, which is how a strategy quietly becomes a story about a company nobody actually works at.
In this episode, Rodney Evans and Sam Rothkopf close out the “Built to Benefit From Change” arc with the piece that underpins everything. They make the case that strategy is what you're executing right now, sort out what belongs at each altitude of the organization, and walk through the four meetings that keep a strategy alive after the offsite ends.
Tools from The Ready:
Session: Free Sky Practice
Mentioned in this episode:
The Secret History, by Donna Tartt
Frankenstein, by Mary Shelley
The Clan of the Cave Bear, by Jean M. Auel
Jaws, by Peter Benchley
The Godfather, by Mario Puzo
“BAU” (“business as usual”)
“chief of staff episode”: AWWTR Ep. 53
“ELT reset episode”: AWWTR Ep. 54
“skills of a leader episode”: AWWTR Ep. 55
“strategy stack”: AWWTR Ep. 2
“essential intent”: BNW Ep. 90 with Greg McKeown
“retrospectives”: BNW Ep. 10 with Jordan Husney
“Sky and Midnight zones”: The Ready’s Depthfinding framework
“even/overs”: BNW Ep. 44
In this episode:
Rodney Evans
Samantha Rothkopf
Listen now:
Episode transcript:
Rodney Evans:
All the strategy work I've ever done is better than what any client has ever had. So just like full caveat, it was garbage when I got there.
Sam Rothkopf:
Is this a podcast with two men? I cannot believe...I loved that. That was the most assertive thing I've ever heard you say, which is saying a lot.
Rodney Evans:
Hey everybody. Welcome back to At Work with The Ready, a podcast about work design and how organizations can make change work in their favor. I'm Rodney Evans and I'm here with my buddy and co-conspirator in all the things Sam Rothkoff.
Sam Rothkopf:
Companies are facing more change than they were built for. The problem is organizations are still running on management ideas from a completely different era. Rodney and I work with leaders and teams who are redesigning how work actually gets done, so change becomes fuel in the tank instead of sand of the gears.
Rodney Evans:
In this show, we typically talk about organizational patterns, but you guys know we're in the "built to benefit from change" arc, of which Sam is the architect. And so today is the last episode in that little mini journey that we've been on, and Sam's going to tell you about where we are and what's today. But first, let's do a check-in round.
Sam Rothkopf:
So here's my question for today and it will make sense at some point during this episode. What is your favorite work of fiction?
Rodney Evans:
Oh, so easy. The Secret History by Donna Tartt. It is -
Sam Rothkopf:
I've never even read that.
Rodney Evans:
—Oh my God, it's so good. There's a genre that I love that is like the New England prep school or college drama. I love the small liberal arts, these children act like grownups. There are a lot of these kinds of works of fiction. the Donna Tartt one is particularly good. And it's one of those things where when I am sad or when I am not really feeling compelled by anything I'm reading, I just go back and read it again. And it reignites my love of reading. It's so good. It's such a beautifully written book.
Sam Rothkopf:
Okay. Well, on the list.That sounds awesome.
Rodney Evans:
You're going to love it. There's bachanalia, there's murder, there's preppy kids. There's everything.
Sam Rothkopf:
You just named my three favorite things. So here we go.
Rodney Evans:
Nailed it. There's probably lacrosse or something, you know...the things.
Sam Rothkopf:
Okay. Okay.
Rodney Evans:
Okay. Okay, Sam, what's your favorite work of fiction?
Sam Rothkopf:
So mine is Mary Shelley's Frankenstein. And I think it was because, and I mean obviously the reasons it's a beautiful book, but it was actually, it has this place in my heart because it was the last book that my dad read to me out loud when I was growing up. Oh wow. He would read to me every night until I was 10, which I think is, maybe it's kind of late. I don't know. I don't know how long people are reading to their children.
Rodney Evans:
I think that's late. That's so nice.
Sam Rothkopf:
Yeah. And the last two books he read to me were Clan of the Cave Bear and Mary Shelley's Frankenstein.
Rodney Evans:
Whoa.
Sam Rothkopf:
Neither of which are really light lifts, but Clan of the Cave Bear is a whole other story. But I think he wanted to have some chats, some conversations with me about things.
Rodney Evans:
We call it priming. He was like, "Okay, so...here's some new topics."
Sam Rothkopf:
"Let's talk about consent." Yeah, exactly. He's a pretty cool dad, as we've talked about.
Rodney Evans:
That's amazing.
Sam Rothkopf:
But yeah, Mary Shelley's Frankenstein was the last one and it was just so sad and moving. And it's also one of those things I see recreated everywhere. And it just always brings me back to what was a very nice kind of moment in my childhood, which is probably not what everyone says about the story of Frankenstein.
Rodney Evans:
Probably not. Wait, funny aside though, because this podcast is where you and I find out all of the parallels of our lives, my dad who had just terrible judgment, just generally not a person who should have parented, but loved to read, gave me two books at the age of 10, which I do credit with my lifelong love of fiction. But those books were Jaws and The Godfather.
Sam Rothkopf:
Those are both great books to be fair.
Rodney Evans:
Great books. I think he probably could have waited like three or four years on The Godfather.
Sam Rothkopf:
Maybe. Dads are weird.
Rodney Evans:
It was a little intense. I had a lot of nightmares about The Godfather. Yeah, severed horses in your bed. It's fine.
Why strategy is cooking, not the recipe
Okay, Sam, what are we going to talk about today? I can't wait to find out how this check-in round ties in to our conversation today.
Sam Rothkopf:
Here we are. Final episode on the new concept of building organizations that are built to benefit from change. We've talked about specific roles like the chief of staff role. We've talked about the team of the ELT and what they need to do to reset, to work with change. We've talked about leadership specifically, what do you need to do as an individual and as a leader to be ready for this new era? And we've talked around and about strategy a lot in those conversations, but we haven't really gone full hog on "Let's talk strategy." What does it actually take to have a strategy that's going to hold in this kind of an environment where change is constant? And have a strategy that's actually going to move organizations forward instead of being the thing that everybody is kind of like, oh, and then we do strategy for four months and then it's useless one month later. Where have we seen examples of it working really well and what are the elements of it? So that's what today's going to be all about and something you've done a ton of Rodney and I have too in different flavors. So I'm excited to talk about it.
Rodney Evans:
I love it. Very excited. Where shall we begin?
Sam Rothkopf:
Well, let's talk about the thing that we both love most, which is talking about how borked it currently is.
Rodney Evans:
Okay, fun.
Sam Rothkopf:
And why it's not working. And then we can get to the good stuff on where we've seen it be really successful because holy cow, do we hear the same things over and over again when we're talking to folks who are looking to engage us in conversation, right?
Rodney Evans:
Totally.
Sam Rothkopf:
And oftentimes it doesn't even. It sort of reminds me of structure in this way where people come to us for structure, but they normally don't have a structure problem. People don't often come to us for strategy, but they oftentimes have a strategy problem and we always end up getting there in one way or another. It's always just a really key element of why there is dysfunction in an organization.
And I mean, I think what it looks like today, and let me know if this is your experience, but it's an annual event that produces a document while the organization executes against last year's assumptions and the environment shifts underneath them. So it becomes just a pretty deck where there are goals tied to it, but no one's actually working on the elements that are built in the strategy. That's what I've seen a lot of in the last few years.
Rodney Evans:
Yeah, that's definitely what I see most often at the ELT layer. And then beyond that, I often see a lot of planning work that looks like alignment to that deck by function that's like, "If I'm running marketing, how do my OKRs relate to what is in that PowerPoint deck?" And too much emphasis on just the right words, just the right measurements, just the right alignment. Is it all going to add up perfectly? I think strategy is treated like a math equation and it should be treated like cooking. It's a thing that lives. It's not a thing that you can just do with pixels. It is a thing that is alive.
I think people treat strategy like the recipe is the thing. And I'm like, it's the recipe and the ingredients that you have in the fridge and people's skills and abilities to cook things and also what everybody wants to eat and also allergies. It's actually all of that is what good strategy is when strategy and execution are done together, but all the emphasis is make a perfect recipe and then split up the ingredients and have everyone go buy them. And it's like, guys, that is literally the starting line.
Sam Rothkopf:
Yeah. I've actually never heard you use that metaphor before, but it's so right. I feel like strategy, it's almost like you got to have an idea of what kind of meal you want to be tasting at the end here, but you can't say it absolutely needs to be summer squash instead of zucchini.
Rodney Evans:
Yes. Absolutely.
Sam Rothkopf:
You cannot have that much of a stringent take on what getting from A to Z really is going to look like.
Rodney Evans:
Yeah. And on the other end of this, you can't just have a pile of ingredients and go, what should we make? This is where I think the things come together and it's like it has to braid together what the market wants, what we want to make and the ingredients that we have to do so. It's too often only one of those things or those things are done in a disconnected way where we're doing market research over here and we're doing what skills and current assets do we have over here? And then we're doing recipe writing over here. And I'm like, those activities need to be done together, which is hard. It's hard and I think can feel quite overwhelming, but if you're not going to do it that way, just don't do it is my advice.
Strategy should be compelling, and non-fiction
Sam Rothkopf:
And we'll get to the why "just don't do it." But I think that's actually related to another thing that people do come to us a lot and say is no one feels like their work is connected to the strategy and it's creating disengagement. And that therefore creates a lack of trust that the execs know what's actually going on in the organization because people see their day-to-day work and then they look at some laundry list of dreams and hopes that has absolutely nothing to do with the reality. And here's where I'm tying it in for those who have been following along. The strategy feels like-
Rodney Evans:
Now I'm with you. Now I'm tracking. Okay.
Sam Rothkopf:
—Strategy feels like it's a fiction to people. This idea of a company that's run in a completely different way that oftentimes does completely different things than what it does today. And it has no contact to the reality of what's going on in the organization.
Rodney Evans:
Or in my example, strategy feels like an inappropriate fiction that your dad gave you that gives you nightmares. Both are true. Look, both work with the check-in round.
Sam Rothkopf:
Oftentimes inappropriate. Let's say that. That what I'm looking at most of the time. The idea that strategy actually should be a really strong work of nonfiction, a compelling strong work of nonfiction is kind of the goal.
Rodney Evans:
I love that.
Sam Rothkopf:
Right now, I've got a trademark to Zoe Donaldson on that one, obviously. And right now, oftentimes they feel like works of fiction, a list of dreams and things that the exec team wishes was possible, but has no ability to execute on and will not change the day-to-day of the vast majority of the people in the organization.
How much your strategy should different levels understand
Rodney Evans:
Okay. So I want to pause here and ask you a question because we work with a lot of companies that are very large companies and we work with one area and then we work with a lot of companies that are $100–300 million-ish in revenue, I would say mid-size companies. How much do you think everyone needs to know about the strategy? How deep does somebody who's a director level with a 10 person team...how much do they need to know versus how much does someone whose job isn't really going to change this year because they're doing BAU, core business, traditional customer, not part of the innovation? How much does that person need to grok? I don't think I have an answer to this question.
Sam Rothkopf:
Yeah. I think that if your strategy has some of the core elements that we believe a strategy should have, which are things like real trade-offs and actual even/overs, that a strategy can be useful for everybody and can actually change the behavior of an organization relatively holistically. Even if there are certain parts of it or outcomes that are not related to what I do at the call center, if there's an even/over that is something like "strong relationships with current clients even/over new clients," that is something that even me at a call center can look at and think about my day-to-day and how that might relate to what I'm trying to do.
But I think that it only works if you have a strategy that is very clear, actually clear trade-offs and even/overs written into it, that doesn't just feel like everybody's pet project put into one, but is making it explicit that there are many avenues that we could have taken. Here's where we're focusing for the next three, six, nine months, whatever you decide the length of your rhythm should be. And I do think that it can be palpable to everybody. But I don't know, you said you don't have an answer to that, but what's your reaction to mine?
Rodney Evans:
I think it should definitely influence people's day-to-day, and I don't think everyone needs to have the same level of fidelity around it. I think a lot of the work that's done to cascade strategy is a waste of time. And I'll tell you about something I made up the other day while I was talking to a client, but he really liked it, so I'm going to say it here. I sort of made up this model in my brain of the more senior you are in the organization, the more general and long term your part of the strategy stack should be.
So if I'm the CEO, I should be making the 18 month essential intent for the company and be like, "18 months from now, this is where I expect us to be." Now, caveats abound. We steer quarterly. That could change. We respond to the market, but I'm going to make a guess. I'm going to make a guess and it's going to be clear. And what I was saying to this guy is why I was like, "I think at that level it's something like that." And then I think at the directs to the CEO level or the ELT level, it's the outcomes to get there. And then I think that at the direct reports to that level, now we're getting into the project work and the monthly sprints and things like that.
And I think where I'm starting to go, and I haven't actually done this at a client yet, so we'll see, is I think some of what goes wrong with strategy is everyone tries to make all of the altitudes of it, and then it just becomes a very heavy exercise of like, "Okay, so I'm a CHRO and my team has a full stack strategy including goals and metrics and OKRs and all of this other shit." And it's like maybe every altitude of a company doesn't need the same stack. Maybe the stack actually gets a little bit broken up depending on our blast radius and our horizon because it's like the best CEOs I work with are looking out two years and are mostly looking at the market and making guesses. And the best team leads I work with are like, "In six weeks, we're going to ship this." I'm like, "The strategy should do the work of keeping those things coherent, not be a really heavy exercise of everybody writing too many things down."
Strategy is what’s happening now, not the future
Sam Rothkopf:
Absolutely. And I think that you're hitting on something else, which is what is a strategy? Because I think there's, to me, a strategy is what we're executing on right now and not a vision for the future. And I think that the strategy should be related to the next step in getting us to whatever that longer term vision is, but that it's actually what we're doing today.
Rodney Evans:
I love this, Sam. I love also that we're figuring this out real time on a podcast. I love -
Sam Rothkopf:
We can cut that part out. We've known this forever.
Rodney Evans:
Well, look, I think first of all, all the strategy work I've ever done is better than what any client has ever had. So just full caveat, it was garbage when I got there.
Sam Rothkopf:
Is this a podcast with two men? I cannot believe...I loved that. That was the most assertive thing I've ever heard you say, which is saying a lot.
Rodney Evans:
I mean, it's just bad out there. It's just so bad out there that it's like whatever I've done is better than what they had just because it was a conversation with reality involved.
Sam Rothkopf:
No more caveats. I think we should stop at better than anything you've ever seen.
Rodney Evans:
It's better than anything they have. And I think you and I are still dissatisfied with the state of this discipline, and so we're always thinking about the next iteration. I love the assertion that strategy is what we're executing on right now. I love that. And I think that to me explains your hypothesis of strategy is execution.
Sam Rothkopf:
Yeah.
Rodney Evans:
Yeah. And it also really clarifies the wrapper around outcomes, trade-offs, project level work, et cetera, et cetera, because it's like the strategy is...it's not a plan for the future, it's what we're doing.
Sam Rothkopf:
And I do think everyone should be able to see themselves in that.
Where vision belongs if not in your strategy
Rodney Evans:
Okay. This is very interesting to me because I agree with everything you're saying. And then I want to ask you, where do you see the longer term visionary work happening and relating back to strategy? Because I know you think that stuff is important because you've told me that. Yeah, if you're a CEO listening to this podcast, what is your mental model for living in the future versus strategy is what we're doing now?
Sam Rothkopf:
Yeah. I mean, I think that there's elements of what you've already said in there, which is there are some people who need to be thinking about that. I mean, your strategy should be laddering up to probably more than one potential futures. Like you were telling me about a CEO you're working with right now yesterday who has kind of four or five potential futures. They're not like, "This is the one and we must figure out how to execute on it." She, of course, is like, "Okay, what is the strategy that we can execute today that gives us the optionality that we're going to need in the future depending on what actually ends up happening here?" And I don't think everybody needs to know about that work necessarily.
I think that they probably did need to know more about it when we weren't in such a survive mode as a culture and a global economy. When you're more in thrive, I think there's more space for that type of really futuristic thinking, but I just don't think people are craving it in the way that they have in the past. And if they are, you can give it to them, but I just don't think that's where the big communication strategy needs to go at the moment to keep all of your best people, I don't necessarily think is in "Here's the 10-year path." It's much more, "Here's a really good looking execution path that you can see in front of you in the work that you're doing today and that it makes sense and is legible."
Rodney Evans:
What really is resonating for me about what you're saying is two things. One is I think too much time from leadership and internal comms is spent on painting a compelling vision for the future that for a lot of people is just distracting kind of, and it creates more questions than it creates certainty. And it's a lot, a lot, a lot of investment. And also it's a lot of investment in educating people about things that might not happen, potentially to the detriment of them just being very clear on what they need to do to be successful. And I think both of those in the landscape we're in where we do feel generally overwhelmed at work by how much is happening, I think that has changed.
I do think that 10 years ago it was more like, "Well, things are working and we're making money, so what's next? I want to hear about the next big innovation to be excited to stay here." Most of the leaders that I talk to right now, their concern is more that their people are worried about the business tanking and being out of a job and the fact that the job market is a literal hell scape. So I love your assertion that it's like what's actually more calming for most people who are not on the leadership team is not to be in four or five possible futures and to just be in like, "This is what we need to do by the end of this year to survive." I think that's really smart. I love it. I'm in.
Sam Rothkopf:
Awesome. Bought. Let's ink it.
Rodney Evans:
Convinced.
Why strategy should keep changing, not stay stagnant
Sam Rothkopf:
What we're circling around here is there are three really important things that current strategy requires. It needs to be present and legible. People need to really understand it. It needs to have explicit mechanisms for the organization to say something has changed and we need to recalibrate, which I think is something we haven't fully talked about yet, but it needs to be really clear that it's not supposed to be stagnant, that it is actually built with experimentation as an inherent piece of it and that we're learning and that we may change course and that this is about how we're prioritizing in the short term, not how we're prioritizing 10 years from now. And that is a really new idea for folks.
Rodney Evans:
Yeah. And it doesn't mean we messed up if the strategy changes. It's probably a really good indicator if your strategy changes.
Sam Rothkopf:
Yeah. Yeah, absolutely. And that's such a reframe to everybody because people are always saying, well, now they've changed their mind again. But I feel like people need to realize that leaders changing their mind is a good thing, not a bad thing.
Rodney Evans:
Totally. Also, quick personal aside, I have had the moment more than once at the ready on the strategy and design team, formerly known as the source team, where we'll do our quarterly retro on our six month outcomes and we basically just do a little dot voting of "Are we on track? Are we off track? Do we not know?" And usually I have seen a very high degree of consensus on where we are in those things. I have no heartburn about everybody agreeing that we are off track and I have no heartburn about us being off track if that was a choice.
And the reason I've never had heartburn is because it always was a choice. It was like when we did it in March, we were off track on the ambition because we prioritized me doing client work in H1 over me pursuing the ambition, and we all knew that and it wasn't a secret. And so when everybody said "We are behind where we wanted to be or we though we would be," we didn't really have to talk about it because we made a conscious decision about it and then it was obvious. I'm just saying this because I do think it's a mindset shift for leaders to not be like hitting the milestones is the point or hitting the deadline is the point or being where you said you were going to be is the point. That's not the point actually. Doing the right work at the right time is the point of strategy.
What’s essential for a good strategy
Sam Rothkopf:
Yes. Amen. That is so right. And you're getting at the third thing, which is that the rhythm is so important and that someone has to own it, which is another thing we've been beating that drum a lot the last few episodes. And I really want to get into what the strategy rhythm needs to look like. But before we do that, there's one more thing that I want to make sure we talk about, which is how do you actually get to a good strategy, Rodney? Because I feel like you've done so much of this and there's a lot of different ways to get to a strategy, but what are the most important conversations or elements that need to be visible for there to be a real kick ass strategy?
Rodney Evans:
I'm going to talk a little bit about something I haven't talked about on this show before, because the elements of strategy we've talked a lot about. I think you should know what strategic challenges from the Sky or the external landscape you're addressing. I think you should have an essential intent that is a clear statement of impact for 12 to 18 months. I think you should have six month outcomes as a leadership team that are where you believe you want to be. And I think you should have a series of even/overs so that you're really clear about what you have to trade off to get those outcomes.
What I think makes a great strategy from what I have seen with my clients is actually the backdrop to those things, which is when a CEO is creating their essential intent and saying, "Okay, 18 months from now, this is where I want to be." And essential intents, the dumb example we always give is when Bill Gates was like, by 2010, I don't remember the year, "By 2010, every household in America should have a desktop computer." I'm butchering that, but that's an essential intent. It's time-bound, it's clear, you can say yes or no to it. It's a single sentence. Everyone can fully understand it, blah, blah, blah, blah.
I think the best ones, the CEO has really thought about what they want the wedge to be. And what I mean by that is they're picking a moat or they're picking a lane, and it's not just, "We want to be the best at everything," or, "We want these particular financial results." It's like a more crisp vision for what they are using their company to do or to make. And too often I see high level strategy try to get at everything. It's like, "We're going to hit the financial targets and we're going to have a great culture and we're going to beat our competitors and we're going to have products that delight our customers." And I'm like, "Boring. I hate it. Any company in the world could write that same shit down and just be like," Salute the flag. Sounds good, boss. "I'm like," Pick something that you're going to be better at than anybody else."
That's really what I'm looking for now. It's just something that feels like it's driven by a market insight. Ideally, it's something that nobody else has seen and you're really excited about and it feels provocative and it feels like a take. I want that conversation to be the backdrop to that stack.
Sam Rothkopf:
I mean, I think you're getting at something really important, which is that oftentimes, and especially the bigger the company, the harder this is.
Rodney Evans:
Of course.
Sam Rothkopf:
So I get it. And I do think that the larger you get, the more lines of business you have, the more strategies you have. I think an overall vision for a hundred billion dollar company probably isn't going to do the thing that we're talking about and that probably lives in sub-teams. So that's a caveat here, but I think that what you're saying is really important, which is that good strategy outcomes need to be in service of something that is cohesive. Yes. It can't just be people are happier and our system is working better and we're selling more product. Those things might all be very good elements to have in your strategy, but in service of what? Why good, you know?
Rodney Evans:
Yes. Yes.
Sam Rothkopf:
And it can't just be because we want people to be happy. It has to actually ladder into something that is a unique differentiator for the business. And there's plenty of ways to have employee happiness be a part of something that is pointed to a business outcome. And it's just the majority of strategies we see just end up being you can see each executive's own hope for the thing that they own instead of-
Rodney Evans:
Get smushed together into a deck.
Sam Rothkopf:
—Yeah. So you're right, the essential intent is probably the hardest piece to land and get through. And I do think that's the job of whoever's leading that group or company is to be the person who lands that essential intent and that those too can move and change, but that if you can't see the essential intent reflected in every outcome, then it isn't a good outcome.
Rodney Evans:
Of course. And I think that for very large companies, to your exact point, Sam, the top of the house in very large companies isn't doing any execution work. And you can argue about whether that's a good thing or a bad thing. That's not really the point of this. If you're talking about strategy as execution and that those things are really one thing, then where it gets defined has to be where it gets executed. And you can't really sort of disaggregate this thing where the leadership team that doesn't do execution work creates a plan that gets handed to someone else to execute. If we want these things to be integrated, then the work we're talking about to make these choices and to make things present and legible and to have specific mechanisms and to have a rhythm, it has to happen where there's work happening. It can't just be like this is where the reporting out happens and where the planning happens and then all the action is somewhere else and we hope that somehow those things come together.
Sam Rothkopf:
Yeah. Yeah. And this is, I think where we can move a little bit to how important the midnight zone is in all of this. Because I think what that requires is for whoever is creating the essential intent to have trust in the next level down to tell them the things that are necessary as the first steps right now in getting to that essential intent and so on and so forth. So then there needs to be a trust both ways where people say, "Okay, that is the essential intent. And we believe that you want to allocate the resources to achieving that goal. Here are the things that we believe we need to do to do that." And then hand that down to the next layer who say, "Okay, this is how it becomes more legible to each group." But it requires both trust that people are going to put the resources against the things that are put into the strategy, which nobody does. And that you have the team below you that can make it happen and that are going to tell you the steps that are necessary first in order to do that.
The hard trade-offs hiding in your strategy
Sam Rothkopf:
I think oftentimes there's this skipping of steps that is so pervasive in strategy. And we actually had this in our last offsite where we realized that we had put some of these big audacious ambitions out into the world. And we realized that as much as we wanted to do ambition five or six, that they weren't actually possible unless we achieved ambitions one and two. And that oftentimes C-level folks want to skip the steps that it's going to take to be able to get to the longer term vision. And sometimes it's possible, yeah, you can make an acquisition that's going to give you that capability or-
Rodney Evans:
But you probably can't.
Sam Rothkopf:
But you probably can't. Cause 95% of those don't work, right?
Rodney Evans:
The data would tell you it's a cool idea, but it doesn't ever work.
Sam Rothkopf:
And that's when things just get super, then it starts to become a work of fiction. And that's where I think trade-offs become probably the most important conversation to have. It's like, yes, you want this, but in order to get that, these three steps need to happen. We need to have an infrastructure that's going to allow for that kind of client relationship. We actually aren't HIPAA compliant in these three ways if we want to- There's just so many different examples that we've seen in those strategy conversations too. "Yeah, that's nice. And here's all of the steps that we need to do to get there." And that's when you have to say, "Okay, and the trade off is we actually need to do that infrastructure work first and we need you to fund it and here's what it's going to take." I think you've said to me multiple times that we've come out of conversations and everyone's felt like they've lost a little bit and you're like, well, that means we've landed somewhere good.
Rodney Evans:
Yeah, that's good. Yeah. Everybody should be a little bit pissed. I think that's right. And also we talk a lot about doing six month outcomes. What you just said is the thing people should put in their outcomes, but don't. So if a CEO says, "18 months from now, I want this company to be AI first." We're changing from being an enterprise software solution to becoming an agentic organization, which is a thing that a lot of companies are doing right now. And the head of product knows that that is going to require a certain level of change in the platform or a sunsetting of the core or whatever. Their six month outcome is that. It actually has nothing probably to do with building agents or maybe it does, but maybe that's a slice of it. But the thing that everybody does is they look at an EI like that and then everybody goes, "Okay, well I'm going to brand the agents. I'm going to build the agents. I'm going to hire the AI people to make the..." Everybody goes to that part and it's like, whoa, whoa, whoa. There's all of this foundational stuff that everyone incidentally does know about that doesn't get written down as the outcome to be like, "Okay, well step one is that our current tech stack doesn't support this in any way. So are we going to build alongside of it and shut this thing down? Are we going to make incremental improvement to the core that we have?"
These are the decisions that you make when you make a six month outcome. And to your point, I think that's often the skipped step. And then people try to square that circle by going, oh, well, we'll have BAU outcomes and then innovation or change the business outcomes or whatever. And it's like probably don't do that, it's all the same people working on these things. And there's nothing wrong with saying in order for us to feel set up to pursue this essential intent, six months from now, we need to have done a bunch of really boring shit. And like, that's ok.
Sam Rothkopf:
Yeah. And if that shit doesn't feel like that stuff is in service of the EI, it is so demotivating.
Rodney Evans:
Yes.
Sam Rothkopf:
And the truth is that -
Rodney Evans:
Because nobody wants to do a RIF and fix the accounting system and fix the tech debt and nobody wants to do that stuff just for fundsers.
Sam Rothkopf:
And when you disaggregate it from the visionary stuff, I just find that to be, first of all, not smart because you don't want to be doing business as usual things that are not related to the essential intent. Those things should be in service of that and can be. They don't have to be. If they're completely separate lanes, then you're doing something different than creating a strategy to execute for the next six months. And it's demoralizing for people because they're like, "Oh, I'm a part of the past. I'm not a part of whatever's being built in the future." They should be together and it should be legible that you can see how it's going to be really tough, this RIF. We've got to cut whatever, 20% from the tech stack. We need to make sure our data is actually usable in these future agentic models, which everyone is— And AI has done such a disservice to the people who know what the hard work is and need to do the hard work because you have these CEOs coming and being like, "My son just created an app that does this though in three seconds." And it's like, sorry, do you not like my CEO voice?
Rodney Evans:
I love him. I want him on the podcast more. That's really funny. "My son....he's 13. He's not going to college." Exactly.
Sam Rothkopf:
You know what I'm talking about. We've been in the rooms.
Rodney Evans:
I know exactly what you're talking about.
Sam Rothkopf:
We've been in the rooms. And it's like, "...Sir."
Rodney Evans:
100%. "Sir, you have a chief legal officer." I don't know. "Sir, this is a publicly traded company." These things are not the same.
Sam Rothkopf:
But it's so funny. It's so funny.
Rodney Evans:
That's really funny.
Sam Rothkopf:
And yeah, it's made that excuse of, "Hey, we can just shortcut all this stuff." It's just made it a lot worse than it ever used to be because AI does this amazing job of dressing things up to make them look finished and done when they would never work at scale or there's just huge privacy problems. I mean, the list goes on and on, but that has definitely exacerbated this issue of CEOs and executives just being like, "Let's just skip all the hard stuff and move into our agentic future."
Why the strategy document should take 5% of your time
Rodney Evans:
Yes, I think that's right. And I think to bring it back to strategy is execution, I just had this insight this moment, which is before we had AI, all of the conversations and negotiation that led up to creating the asset was the best part of the work. Now that the asset is basically the starting point, there's a real opportunity to do that wrestling after, which is where it always should have been done anyway. The asset always should have taken 5% of the effort and execution should have taken... execution and reflection and steering always should have been 95%. It was always reversed. But now that AI basically makes the strategy asset and the hypothesis and the narrative immediate, I'm like, "Great. You guys don't need to spend a lot of time on that. Now let's have the op rhythm where we execute this thing and we continue to investigate what's happening out there and we continue to investigate how our execution is going and we continue to change elements of the strategy and we continue to make new bets." We should have a lot more capacity to do the good stuff now.
Sam Rothkopf:
Yeah. That's such a good point because I think, and this is the other question we get asked all the time is "What are the human jobs now?" Because to your point, it took so long to get to the asset before, for good reasons, right? For good reasons. And now you get to the asset and it's that's where you should be spending the time, the time where you should always been spending it. Let's get on this ride and actually think about how to get these things done instead of generating ideas for the rest of our lives and not testing any of them out in reality. Now we get to do a lot more testing and learning and recalibrating and maybe that's yet a new epiphany of the thesis is "The onus of work to get to the ideas, you used to be 90% and it should be 10% now and the rest should be on execution.
Rodney Evans:
Yeah.
Sam Rothkopf:
I love it.
Rodney Evans:
It really
Sam Rothkopf:
Should be. Let's trademark that too.
Rodney Evans:
Let's trademark that. Amazing.
Strategy rhythm essential: retrospectives
Sam Rothkopf:
Okay. But I think that where you were just heading, Rodney, is kind of the last big thing I want us to talk about today is around the rest, that other 90% or what we think the 90% should be right now, which is what does the strategy rhythm look like? Because as we've talked about, you get to the assets and then people just say, "Okay, let's develop OKRs for these assets." And then nobody ever looks at them again until six months later they have to look at their OKRs and see what happens. And I know that you've done, I think you're in the middle actually of two or three executive team resets where you're setting up these rhythms and there's a lot you can do, but what are the most important things that absolutely need to be visible in order to have a strategy that's going to hold and make sense for the business?
Rodney Evans:
I think you have to have a quarterly strategy meeting. And I think that meeting has to include a real look back at the last quarter, like a real retrospective that ideally is not just metrics. It should be more focused on what did we learn than did we hit it? Because remember, we're trying to steer it. We're not just trying to do it. And so when I say, or I think too often I just see "Red, yellow, green, did the numbers hit the milestone?" And I'm like, don't do that. Let's have a real retrospective that's like, what did we learn? Were there any interesting quiet signals? Anything that surprised us, et cetera, et cetera.
I also think that session, whether it's all together or it's disaggregated in some way, you got to do some Sky work as part of your strategy rhythm. You've got to, as a leadership team, be looking externally at what is going on in the market and what your competitors are doing and what each of you is learning. And then you got to refresh the stack. I would start there nine teams out of 10 that I know don't have that. So that's a great place to start. Have a day a quarter of the executive team getting together, looking back, looking out, and then refreshing the stack. You're going to be in better shape than 90% of the leadership teams out there if you're just doing that.
Sam Rothkopf:
Oftentimes I would say that's one that gets just people never want to put a retro on the calendar because they're not using them in the right way. It really, to your point, it isn't about who has been hitting it and who hasn't. It has to be about what was the context around these different things? What do we maybe want to change for the next quarter and why? It's just a regular conversation that makes it so that there aren't those surprises that you and I were talking about where suddenly at the end of the year, no one knows why this OKR is red.
Rodney Evans:
That's right.
Sam Rothkopf:
Everyone will know and we will have all made decisions together on whether or not we need to accelerate and put more investment into that. So if you're going to do one meeting with your team, make sure that one is on there quarterly and cannot be moved.
Strategy rhythm essential: resource allocation meetings
Rodney Evans:
I think we have to talk about resource allocation. I think people make this so complicated. It becomes this very heavy finance exercise
And I don't generally think it needs to be. I sort of look at resource allocation as like, "Okay, we have our essential intent. We just steered it because it's Q2. We made a couple of changes to where we think we want to be. We have new six month outcomes for H2. Let's look as a team at those outcomes. Is there anything anybody is going to need that they don't currently have to achieve them? Do we have guesses about that?" And maybe it's a hire or maybe it's a travel budget or maybe it's subscriptions or maybe it's an acquisition.
It could be all manner of things, but I think that people try to do this as a spreadsheet exercise to the dollar. I actually think when it's a higher altitude, it's a little bit easier. When it's like, "Okay, we agree in principle that we don't have this kind of data team and to make that outcome, we need this kind of data. And so can we agree in principle that we need a team of three-ish to do that and it's going to cost a million-ish for the year? And does that feel about right? Great. Do we need to find that million somewhere else? Where does that come from? Great."
To me, I've done this so many times with the executive teams, literally on post-it notes or on a whiteboard where I'm just like, "What are the needs? Great. What are the approximate dollars? Great. How are we going to pay for that? Is it a margin hit? Are we taking it from somewhere else?" Et cetera, et cetera. I don't think it's as hard as people make it.
Sam Rothkopf:
Yeah. And I've definitely. I've been there too, and this is where that conversation on, well, then there's the business as usual work and then there's the other work starts because it's definitely like, "Yeah... but those people that we want to do this thing are doing all of these other things.
Rodney Evans:
Yes.
Sam Rothkopf:
So at least that's where I've seen it go. So it's like, are we reprioritizing their time? But no, that's what we need in order for the business to run. And that's where I think the rubber really meets the road on the trade-offs because there's only oftentimes a finite amount of resources and it's like, well, if this is what it takes for the platform to keep running and we know we can't make any changes there, then maybe we need to have a less ambitious six month outcome.That's where you really...in those resource allocation meetings, I've found oftentimes you have to say no to things more, so that you can actually invest in a couple of things because that is where in those resource allocation meetings, I agree with you, when it gets too down in the nitty gritty, I mean, I've seen some spreadsheets.
Rodney Evans:
Yeah. It just gets out of control.
Sam Rothkopf:
The amount of time it's taking us to fill out this spreadsheet is in itself the resources that we needed to get to this outcome. And it can't be just, "Well, we'll just figure it out." So there's definitely a happy medium between the two, and I've seen people just kind of push it through and say, "We'll just figure it out," and that's when you don't make any progress on the strategy.
Strategy rhythm essential: prioritization meetings
Rodney Evans:
Yeah. That brings up another point which relates to the prioritization meeting. I do think these resource allocation and prioritization are really good buddies because if we deprioritize something, generally that frees up resources that we can allocate to something else. But there's a real Midnight Zone thing here too, which is like, I cannot tell you how many organizations I've been around where deprioritizing something basically feels impossible because it requires a team to re-contract with an external or internal customer and to say explicitly, "We will no longer be providing X or we will no longer be meeting this SLA or you will no longer have this level of service, period." The rest of that sentence is because we've decided this other thing is more important.
And so then everybody is straddling both worlds and they're just so stretched. And then both sides suffer, the future is underfunded, the present is propped up. It's a terrible situation, but I really feel like this comes down to a midnight zone thing of people have a real tendency to protect the role that they've been in and to not want to give short shrift to whoever their users have historically been, even when it's in service of the future.
Sam Rothkopf:
So do you have those meetings separately then, resource allocation and prioritization?
Rodney Evans:
I generally do. I like to go quarterly strategy, fast follow with prioritization, then resource allocation. I like to do prioritization and resource allocation separately and very time bound. Those are not all day meetings. Those are 90 minute meetings so that ideally inside the first month of the quarter, we're rolling.
Sam Rothkopf:
Got it.
Rodney Evans:
Yeah.
Sam Rothkopf:
There's a fourth, right? There's one other that you're having on a more regular basis.
Strategy rhythm essential: decision meetings
Rodney Evans:
I do like to have very few executive teams I know will sign up for this and they should. I do like to have some kind of decision meeting on the calendar that's about cross-functional, like the big cross-functional decision. I'll give you an example. I feel like complex decisions in executive teams often take on a life of their own and the person who either proposed it or is advocating for it ends up being the person that kind of pushes it through, even when it's a decision that really should be owned by the leadership team.
And it'll be like somebody got approached to do this partnership. I got approached to do this partnership and I think it's a really good idea and now I'm showing up with this partnership on my agenda and nobody else really knows that much about it and I generally have pretty good ideas and it sounds good enough. And so it kind of gets green lit without people really understanding what I'm proposing and what it's going to take and what it's going to mean for the strategy. I think having something in the rhythm about those decisions that are like an acquisition, a riff, a significant change in the strategy, a big partnership, a new product exploration, these do not have to be long, heavy meetings, but it's an ability for the person who feels strongly about it to bring forward a proposal that everybody digs into and consents to.
Sam Rothkopf:
Yep, totally. Amazing.
Rodney Evans:
Sweet.
Sam Rothkopf:
Gosh, I could keep going, but we've really gone after it. Anything else you wanted to make sure we got to?
Why new strategy execution takes time to pay off
Rodney Evans:
The one thing I want to say about the strategy execution op rhythm, especially for leadership team members, is I often think that executives, because they're learning this new way of working at the same time as they're potentially doing strategy and execution differently, they often feel like it's work around the work or they feel like it's slowing things down or they feel like it's overly structured or they feel like it's not something that it's supposed to be. They're incorrect about that.
And it just takes six months of executing your strategy in a different way to realize that it's not more effort, it's different effort and it's better effort because it's cohesive and because you're doing the work all along the way rather than doing a big burst of work, then going quiet and then cleaning up the mess that you made, you're continuously steering things so that there is no mess and there are no surprises and you don't miss the big market opportunity, but it is a shift because it feels more effortful at the beginning. And until six months down the road when you see what you got and what you avoided, you're just going to go like, "This feels like too much conversation about the work."
So I'm just saying that as a PSA because every team I've ever worked with has had that reaction and in six months they go, "Oh, I get it. I see. I see how it worked." But it doesn't feel like that when you start. It feels like, "Are we seriously talking about this again?"
Sam Rothkopf:
Totally. Yeah, I love that PSA. Jack, keep that one in there.
Rodney Evans:
Awesome. Okay. I think we did it, Sam. Did we do it?
Sam Rothkopf:
We did it.
Rodney Evans:
Sweet. This show is edited and mixed by Taylor Marvin at Coupe Studios and produced by our friend Jack Van Amburg. At Work with The Ready is created by The Ready where we help organizations around the world change the way they work. Thank you for listening.