Preparing for a Positioning Exercise

In a positioning exercise, it's very important that we don't attempt to do positioning that works for every customer that we've ever closed. That's not the point. The point is to do positioning that gets us to a great story that attracts good fit customers, allows us to close those good fit customers easily and have those customers be happy after we've closed them. So if there's some weird ones out there, we want to write them on the board and put X through it. That's it. Welcome, everybody, to another edition of the positioning show with me, April Dunford, your host. This is a set of recordings I'm doing to cover the new stuff that I've added in. Obviously, awesome. The second edition, this is the new version of the book that I originally released in 2019. And now in 2026, there is a new second edition. That second edition includes a bunch of new material and expanded material, most of which is come out of the work that I've done with a few hundred clients working through the methodology that's described in that book. And so there are a whole bunch of things that are new or expanded or slightly revised. And so I thought it would be fun to do a set of podcasts specifically diving into the new stuff that's in that book. So in the last podcast, I covered how I had changed a little bit of the structure. The original book had 10 steps to doing positioning. That drove some people crazy because there are five components of positioning and there are 10 steps and people didn't like that those numbers were the same or not the same I should say and oh, so in the revised edition. I decided I was going to solve that problem by having pre work that happens. There's the five components, which are the five steps of the core exercise and then there's post work that happens in the last episode I talked about that there were a set of decisions that you have to make. Before you do a positioning exercise because a lot of the things will happen downstream from that and specifically one there was this idea of a positioning readiness check like is now a good time for us to do a positioning exercise. Are we in market have we sold some stuff if we haven't can we all be in agreement that we're not actually doing positioning we're creating a positioning thesis. But let's say we agree on that and then the second thing is ensuring or getting agreement that we're doing positioning for customers and not looking for positioning for investors or positioning that we might use to attract a new employee or something like that this methodology was built for customers and that's different. The third thing was defining what exactly it is you intend to position is it the company is it a product is it a specific grouping of products and then once we figured that out we need to think about who is the actual persona that we're going to target for that positioning. And so once all those decisions have been made and you know whoever it is that's instigating this positioning thing has gotten agreement on that then you're ready to go to the next phase which is you know there's a set of work that needs to happen before we actually do the positioning exercise so that's what I want to cover in today's episode specifically. The first and the obvious one is we need to assemble a positioning team now if you've read the first edition of this book you know that I feel really strongly about this that positioning is not a thing that can just happen in the marketing department and before I really got my head around this I struggled with this myself as an in house marketing person. I was always taught that positioning was a marketing exercise it was the thing that the marketing team did but what I noticed is that whenever we came up with positioning on our own in marketing. It often did not survive the jump to sales so we would do this positioning we would often create sales support materials including pitch decks throw it over to sales and sales would look at this and say what is this hot mass why have you done this well our these decisions made. We disagree with a lot of the things that are assumptions in here and they would generally not use our pitch materials they wouldn't use our sales support materials and we wouldn't be grumpy sitting over in marketing saying those idiots in sales don't appreciate our hard work and sales would be sitting over over on their side saying. All those folks at marketing should like you know get out of the office once in a while and understand customers the way we understand customers we are often a similar thing going on in product like product was often dealing a lot more with customers than we were you know we would bake in assumptions to this positioning that the product team would not necessarily agree with and then lastly there's you know the elephant in the room would be the CEO or the founder who obviously had opinions about this. And it became very apparent that if we did not include that person in the decisions we were making about you know why we win in a market and what part of the market we wanted to go after and and you know what is the best fit customer look like and things like this. If we didn't include the CEO or the founder in those discussions of the decisions that we made then often the founder would not agree and then we would have a fight on our hands and so it became obvious to me having done a lot of positioning work when I was in house that the best way to do it would be to get a group together and that would have a few positive impacts one would be. You know we could ensure that everybody got to say their peace and we would have a higher chance of getting agreement and alignment but the second thing is that everybody actually came with good input into the process like for example the sales team knows more about the competitive landscape the true competitive landscape then anybody else on the team does and product often knows a lot about who we should be competing with or who we might be competing with or who we could be competing with. But only sales can tell us who actually shows up in a deal similarly when we got talking about differentiators or differentiated capabilities product management team knows more about that than anybody else and often there's cool differentiators that you know marketing is not marketing because they don't understand it sales isn't selling because they don't understand it but product understands it a lot. So if we have product evolved then we get the benefit of that and then in my experience particularly if we've still got a founder around the founder often has this kind of depth of understanding of where the product came from and the point of view on the market that formed the product in the first place. This is often really interesting perspective even if it's years later and the product has really changed in the market has really changed there's often this kind of kernel of truth in what the founder can bring to the table that you don't necessarily get from other folks in the team and so I've always found it really really helpful if the founder still involved with the founder to be there and then obviously the CEO cares you know if you're going to make some decisions about what a good fit customer looks like and how we win in the market. Good CEO has got some big opinions about that so you know it would be way better to have those opinions on the table while we're working this stuff out then to try and sell the CEO on it afterwards so we need to figure out who needs to be in the room beyond the obvious attendees so obviously we need marketing sales product I usually have customer success in the room often customer success that you and cross sell and up sell it. And it's really good to have whoever leads that team in the room and then CEO founders these are the obvious people I find it's often good to round it out with a few more so often it's good to have multiple sales voices in the room because sales folks don't always agree on stuff and frequently we have a sales leader sometimes the sales leader is newer and maybe hasn't been around as long and then it's helpful to have some perspective of folks that maybe been excellent. Folks that have maybe been exposed to more deals it's also helpful like if you have sales leaders in different regions or sales leaders that focus on different parts of the market it's good to see those other perspectives there so I think that's usually a good idea to have some experienced account executives in the room and to make sure that you have coverage across all the geographies are all the different places where you focus. And I think goes on the product side so if the company is done let's say acquisitions there might be product folks that are more familiar with the acquired products than the core product and so we would want to have a mix of people in the room that could speak to the capabilities of the major products that we are trying to cover in the workshop itself. The last thing I'd say about forming a team is that when I've done these workshops often will have folks that you might not think would normally be in an exercises like the head of HR or the head of legal obviously if you have a strategy person if you're big enough to have a head of strategy or someone focused on strategy but sometimes we have a COO or somebody that has a role that maybe isn't it is an obvious that that person should be involved. The way I usually look at this is if there is someone on the executive team that has big opinions about this stuff then we want to include. include them. And we want to include them because it is much easier and better to get those opinions out on the table while we're forming the positioning than to have to go to those people later and try to defend the positioning and have them say, "I just fundamentally disagree. I fundamentally disagree with the things that you have assumed here. I fundamentally disagree with all of this." It's very hard to get people on board afterwards. It's much easier that if those people care about this stuff, have a big opinion about this stuff, let's bring them in the room. In my experience on this, we're trying to keep the room as small as we can, but also have the right mix of people. So in the work I do, it's usually about a dozen people. Sometimes it goes up to 15. If we get beyond 15 people, it starts getting really hard to facilitate the conversation and there's just too many voices, so that's hard. The other thing I would say here is it's okay to have observers as long as they understand that their role is mainly to be observers. For example, we usually have one or two marketing executives in the room, but there might be some folks in marketing that are ultimately going to be responsible for content creation and messaging and building sales support materials and things like that. Often, the executives are there sitting at the table to give their input, but it's often not a bad idea to have the folks that are going to be tasked with doing some of the downstream work, actually in the room, so that they can understand the nuances of how we got to where we got to in this positioning. So it's not unusual when I do these things that there's maybe a handful of people kind of sitting on the sidelines who occasionally pipe up with some good perspective, but their primary role there is to be observers to understand how we got to where we got to and to see the process as it moves along so that it all makes sense to them. So that's the first thing. We need to decide who needs to be in the room. Now, once we've gotten this list of folks in the room, there's a couple of things that you want to do to make sure that those folks are prepared. So one of them is this idea of thinking about who's a good fit customer versus a bad fit customer. Now, let me tell you, and obviously, awesome, the first edition. I had a chapter on this in the chapter to bad title. I can't remember exactly what it is probably because I put it out of my mind because I hate it so much, but it said something like, you don't figure out who's your good fit customer, which is not what I meant. So all kinds of people sent me email and said, wait, I don't understand it April. We haven't even started yet. And you're asking me to figure out who my good fit customers are. Isn't that the fourth component of positioning? And don't we figure out best fit customers after we figure out value? And oh my gosh, I hate this thing. And people would send me emails. And they'd say, you know, on page, whatever you said this thing. And I'd always be writing them an email back saying, I know I said that man, but that's not what I meant. Why can't you read my mind on this? And anyways, it's probably the thing I hated the most about the first book. So it wasn't my intention. So I've rewritten it and hopefully I've done a better job this time because oh boy, if y'all fill up my inbox again with this, I'm going to I'm going to feel bad. Here's what I mean by this. In B to B, it is not unusual for us to have clients that pay us money, customers, and some of them are very good fit and some of them are a bad fit. And what I mean by that is, at a very macro level, some of these companies, we probably should never have closed business with them in the first place. It made sense at the time and somehow we managed to get that deal over the line. But looking back on it, we'd say, you know what, they were weird and probably not a good fit for us. So I give you an example. I worked at a startup long time ago, early, early in my career. And when I joined, the company had six customers. Five of them were all kind of the same. And then there was the sixth one and the sixth one was this big insurance company. None of the other ones were insurance. This big insurance company. And they were terrible. They were just weird. Everything they did was weird. They were so weird. They had written their own relational database. Like at a time when relational databases were purely commodity and not even expensive. But they were so convinced that everything they did was such such a special snowflake thing. They had written their own stuff. Like they were just super, super weird. Anyways, they bought from us and they were by far our biggest customer. So we had maybe a couple million revenue. And these guys accounted for almost half of that. But they were such a bad customer. So they couldn't find anything else they like. They settled with buying our thing partially because we were cheap, but partially because we were so flexible. Like if they asked us for some weird feature, we would build it for them, which, you know, trust me, you don't want to do that. So they were kind of treating us like their own little private custom development shop where they didn't have to pay for any of the custom work. They just had to pay the license fee every month. And oh, it was terrible. And anyways, when we finally got the team together to look at the positioning for this, we made a conscious effort to not include that customer. Because if I asked a question like if we didn't exist, what would a customer do? The answer for them would be different than it would be for all the other customers we had. And if I said, well, what have we got that, you know, everything downstream from that? If I said, what have we got that the other alternatives do not, it would be all the same for the rest of our customers, but for that one, it wouldn't be. And so at this step, we don't have to understand why a customer is good fit or bad fit. If we're B2B, we know that often there's a handful of customers that we just know in our gut, they're not good fit customers. We are unlikely to sign another customer again. We look at them and we say, yeah, yeah, yeah, there's those guys, but they're weird. So in a positioning exercise, it's very important that we don't attempt to do positioning that works for every customer that we've ever closed. So if there's some weird ones out there like this, our big weird insurance company, for example, we want to write them on the board and put an X through it. That's it. So we don't have to figure out exactly why they're a good fit or why they're a bad fit, but trust me, if you're B2B, every company I've worked with, we have this conversation and I say, look, now have you guys got some customers that are bad fit and there's this, you know, look and everybody usually laughs and they say, oh, yeah, yeah, yeah, there's these guys right there. Okay, so we just write them on the board and put an X through and that's all we're doing at this step, but it's good to have that conversation before we get into the positioning exercise, because people will want to bring up these one off weird examples, especially when we're saying something like, who do we compete with? They'll say, oh, well, there was that one time that we sold the Walmart or we sold to all state or we sold to Goldman Sachs and you know, and we just want to say, look, this doesn't have to work for everybody and it certainly doesn't have to work for weird one-off outliers. So what we want to do is take these big, weird, bad customers and even if they pay us a lot of money, we want to recognize that these are kind of one-offs and we are not likely to see another company like that in the pipeline again. That's it. I hope I did a better job of explaining this this time around because let me tell you, that caused a lot of confusion. People were sending me email like, they probably can't even get started on this thing because I don't know why my customers are good or bad and I'm like, oh man, I wish I did a better job of explaining that. So I think that's a good thing for us to get aligned on, particularly B2B, every company's got some weird ones like that. Then there's a handful of other things that I think are really good to happen before you get into the exercise. So one of them is this idea of let and go your positioning baggage. This is usually done by just having kind of an open conversation about it and it helps if the CEO maybe leads this discussion and gets everybody feel uncomfortable with this. But this is to kind of back up and say, look, we've always thought of ourselves this way. And when we started the company, we built it to be this thing. But a few years have gone by and the product is different and the market is different and the customers are different. And when we look at it now, maybe what we are is something different. It's okay if our thinking about who we are and who we serve and what the value is that we can really deliver to customers, it's okay if that changes. I find this is really helpful, especially when you have a mix of new employees and some really longer term folks that have been around since the very beginning that have kind of really internalized whatever the positioning was back when they joined. So, you know, I'm thinking specifically of a company that I worked for once where, you know, there was a group of folks that had been there since the very beginning and this thing was positioned as a database. And they literally would say, "We're database people." Like, "We are database people and we are delivering a database." And that's what we are. And eventually we shifted the positioning to be more of a data warehouse. And it was hard internally for some folks to get their heads around that because they, you know, they really identified with this database positioning like a couple of the founders had PhDs in database technology. They didn't consider themselves a warehouse people. So, I think it's good to kind of have that discussion. And if the CEO founder is leading the discussion, I think that's even better to sort of say, "Hey, like, you know, I know we've always thought of ourselves in this way. I know we've always thought about the value we deliver this way. I know we've always thought about the people we serve this way. But we're just going to park that. And we might get to the end of the positioning exercise and nothing changes. But we may not. And we should be open to the idea that things can change. So, this, I think, is another good discussion to have before you start the positioning exercise. Personally, in all the workshops I do, there's a little kind of prep work thing that goes around that folks read. You know, a lot of people that come and work with me have read my book before. This is good in that the book kind of defines when we say positioning, this is what we mean. And when we talk about the component pieces of positioning, this is how we define those. So, I think there's a good step to do, which is just kind of aligning your positioning vocabulary. So, if you're listening to this and you think, "Hey, I want to run one of these exercises, you know, by myself inside my company." I think it's worthwhile having, you know, and I do this with a little presentation. And, you know, it's a little five or six slide PowerPoint that basically says, "How do we define positioning?" Give us an example of what we mean by that. Give us an example of something that was poorly positioned and something that was well positioned. And then let's talk about the component pieces of positioning and just define what we mean in each of those components. I think this is a really good thing to do before everybody gets in the room before we start the positioning thing, just to kind of level set everybody. Because there's a lot of misconceptions about it. And let's be honest, like if you're not in marketing, this might be the first time you've ever even heard the word positioning or ever really thought about it. So, a lot of people think positioning is the same thing as messaging, for example. And it's good to sort of lay that on the table and say, "Well, no, it isn't." And actually, a good way to think about positioning is kind of a set of fundamental inputs to the things we're doing in marketing and sales. And that includes messaging. And then I also think it's good to just kind of lay out some of these things in advance. So, what is positioning not? And when we say positioning, what do we mean? And when we talk about the component pieces, like, what exactly do we mean by competitive alternative? What do we mean by a market category? What are these things? So that people have at least enough of a background in this that we aren't spending the first hour, two hours of the positioning workshop trying to define all this stuff. Or worse, we get to day two. And somebody pops up and says, "Well, I didn't think that's what you meant when you've said competitive alternatives. I didn't think you meant that. We don't want to have that." So, it's way better to kind of define it up front. You may be send around a little pre-work, maybe give people something to read. Or, you know, at the very beginning of the workshop, maybe start with this common language, common definition. And that way, we could just move forward without, you know, get halfway through the process and having somebody put up their hand and say, "Wait, hang on a second. I didn't think that's what we were doing here. Let's back up." And then, you know, it just waste a lot of time. So I would recommend you do that. The last thing I would do before the positioning exercise starts is a review of what we have decided so that we can frame the positioning exercise. So these were all the decisions we made before we formed the team. So those decisions being what exactly are we positioning? So, you know, I think it's good to come to the team and say, "Look, we've already made a decision. This is the product we're going to position. Or we're going to position the whole company. Or we've decided to take this one platform and we're going to position that. And explain the thinking around that and just tell everybody, "This is it. So forget about the rest of the stuff. We're just doing this. This is the boundaries of the exercise." And I think also reviewing the personas that we've decided to focus on and say, "Look, there's this concept of a champion. In this case, the champion is this. Or maybe it's this combination of this person and this person. When we go through this exercise and we talk about things like value, we want to have that persona in our mind when we are doing this exercise. So I think it's helpful to review that with everybody on the team too." So those are the big things I changed that in the setup part of the book, which I think is quite a lot of change from the initial book. A lot of these concepts were covered. They were just organized in a different way. And some of it, I didn't go as deep on it that, as I probably shouldn't, because a lot of people came back and talked to me later that they were super confused about that. So anyways, I hope that clears things up. That's it for this episode. Next episode, I'm going to cover a couple of things. But the main one I want to cover in the next episode is the first step to the proper positioning exercise, which I don't know what step it was in the first book, but where we start talking about competitive alternatives. I've changed my thinking a lot about what matters and doesn't matter in the competitive alternative step. And I also think underestimated how important it was to really nail that step at the beginning of a positioning exercise. Now I think it's one of the most fundamental things to get right in an exercise because we really get that one right and everything downstream flows really well. So that's what I'm going to cover in the next one. So again, thanks so much for joining me. Again, what we're doing here in the next few episodes is sort of a mini series covering things that are new in the second edition of my book on positioning called obviously awesome, which is releasing February 2026. I can't wait for you all to read it. And I'll see you again next time. Thanks.