Win-Loss Deal Strategy: Build an Organizational Competency and Win More


Tim Caito:                                            

Hello, I'm Tim Caito with Force Management. We specialize in helping selling organizations drive profitable revenue. I personally help those same organizations win better deals faster. Win the kind of ones you want to win. Now, today, we want to leverage that focus and experience to share our perspective on building your win-loss deal strategy. That's a phrase I'm going to explain as we go along.

Now, overall, it's great to be part of this virtual conference focused on capturing more value from your win-loss analysis. In fact, that's my value proposition for you today in this session. Share a perspective that will help you get more value from win-loss deal reviews. Now, to do that, we have to start with a traditional goal of win-loss analysis, and that is to generate retrospective insight. Help us better understand why we won so we can replicate it. Help us better understand why we lost so we can prevent it. Now to capture more value from your win-loss analysis, we think there's an important additional consideration you have to keep in mind.

In my role at Force Management, I frequently coach our customer sales teams on how they might win a particular deal, and it's not uncommon for that coaching to occur mid to late in their sales cycle. Now all too often, those coaching sessions reveal some pretty predictable BGOs or blinding glimpse of the obvious. For example, we find there are some significant gaps in either knowledge or position on this deal. Number two, the deals are so big or so significant, we can't afford to lose them. And then number three, we have to do something to save those deals, and sometimes that something are some very dramatic actions.

Now to be fair, some of those deals we win, and those usually get analyzed to figure out how in the world did we win from such a bad starting position. Frankly, some of those deals we lose which are almost always analyzed to understand why we lost. Now, in hindsight, that retrospective insight that we uncover during win-loss reviews on those kinds of deals, are again almost always the same. Because we had to do some extraordinary things to get the win, some of those deals didn't end up being so great. In fact, in hindsight, what we realize is those deals never had a chance to be great. And in fact, some of those deals we should not have been involved with in the first place, right? Which is likely why we may have lost them, or at least had to do some extraordinary things to save them. But eventually on those kinds of deals, someone always asks the same question, "How did we get in this position?"

Now the answer to that question is frequently, the insights from win-loss reviews conducted previously did not find their way into this deal pursuit, right? Especially in three high leverage areas: guidance, process, and discipline. So this insight needs to be factored into our approach for conducting win-loss analysis, not just to win more, but to put a strategy in place, to win more of the kind of deals we want to win. We call that a win-loss deal strategy. So today we're going to talk about building organizational competency to drive your win-loss deal strategy so that you can win more of the deals you want to win.

Now to do this, you have to keep two key perspectives in mind: the engineering perspective and the organizational competency perspective. The engineering perspective... Now, to be fair, I'm not an engineer, but I understand this perspective, right? This perspective says, "The results that you achieve are the perfect and predictable results of the system that produce them." With that perspective in mind, you want to change the results, you have to change the system. So that's one thing to keep in mind. Second perspective, organizational competency. Winning the deals you want while avoiding the deals you don't want is, in fact, an organizational competency, not just an outcome that's driven by the sales team.

So let's look at this and dig in a little bit deeper. As I just mentioned, one of the fundamental challenges we see most selling organizations struggle with is realizing they have big problems with their deals either too late in the sales cycle, or unfortunately after they either won or lost the deal, and when you have this realization, you must take action to address it. We call this being in the reactive state. So when you take that engineering perspective and step back to analyze the system that produced that reactive state, you often see there are three common root causes.

The first one: lack of defined guidance to the field organization on what constitutes a good or a bad deal. You don't give them guidance, don't be surprised on what you get back. Now, you might say to yourself, "This seems like it would be intuitive to know what a good deal is." One may ask you a question, "How many of you have had your definition of a good or bad deal change within the last few months?" I would venture to say most of you had a pretty good idea of what good looked like in December of last year or January this year, then we hit a global shutdown. Has the definition of good changed? Have we shifted from number of products, number of services to let's just generate cash, that's what we need to do? Well, whether yours has changed or not, I will assure you most of your customers' definition of good and bad has changed, so we must react accordingly.

Second big root cause of this reactive state: lack of organizational process. Now, what I mean by that is relative to the trajectory of these deals. Lack of organizational process to check in on the trajectory of those deals early enough that we can either keep them on the right trajectory towards winning the kind of deal we want to get, or make some course corrections if we're off track, not waiting till we're too far into it before we get into that reactive state.

And then the third root cause is this idea of lack of discipline. Lack of discipline that consistently applied the guidance on good and bad deals and the organizational process to make sure that we keep things on the right trajectory. Now, retrospective insights are great. Don't get me wrong. We are big fans of win-loss analysis, but to be most valuable, those insights have to be leveraged proactively in future deal pursuits as well. Everybody gets that. The problem is that these insights have not very frequently been operationalized to be able to be leveraged on those future deals. So to get more value from your win-loss analysis, we found you need to develop and commit to a set of organizational competencies that can be leveraged proactively to win more of the deals you want to win, right? So let's look at each of those three root cause areas as actually places where we could put some organizational focus and build some organizational competency to, in fact, be able to put ourselves in a position to win more of those kinds of deals we want to win.

At a high level, first, from a guidance standpoint, define and keep current the definition of good and bad deals. We owe that to our team. It's a very dynamic definition, right? We've got new people that are coming on that maybe learned the definition somewhere else, we got to give them the best definition of what we mean, and what we mean now. Did you go through any kind of merger/acquisition? My guess is the definition of good and bad has changed. Are you aiming at a new segment? Are you migrating your business from on-prem to on-cloud to omni-channel? It doesn't matter, right? If the definition has changed, we owe it to our team to give them more guidance on that, and odds are: the more we align our efforts around the guidance of what good and bad is, has a huge impact on our ability to win or lose.

Second area: that area of organizational process. There's actually a couple high level things there. Number one, put in place an ability, a process that allows us to check in on the trajectory of these deals early enough that we could keep them all in the right way or make course corrections. And then secondly, from a process standpoint, define and execute the strategies to win the kind of deal we want.

And then that third area, discipline. Consistently applying the guidance and the process so that we can win those kind of deals we want and have the discipline to make sure everyone sees this as a normal part of our operating rhythm.

Now, to get very specific with you, some things you can walk away from this session and do to be able to best leverage insights gained from your win-loss analysis, to be able to move them into your current deal pursuits, couple of items here, right? Seven items for you. In the guidance area, three quick things. Number one, identify that kind of customer pains that your customers are focused on that you're best suited to address. Don't just give your team use cases for your solutions, right? Help them understand that kind of customer problems that you're specialist, that you've got a proven track record to help people resolve. You spend more time in your area of strength, my guess is you win more deals.

Second thing that goes along with that, define the required capabilities your teams need to target. When they're in those conversations about those big problems you specialize in, leverage your expertise to say, "By the way, no matter who you work with customer, if you've got these kind of problems, you're going to need to put these required capabilities in place to address those. Oh, by the way, let's make sure your people are targeting the required capabilities that not only help the customer achieve their big outcomes, they also align very nicely with your differentiators." Right? We're giving them the keys to be able to set up our differentiation.

And then lastly, when they get into the deal pursuits in the final stages of reaching agreement, give them guidance on the components of a final agreement that would make a deal great for you. Not just good, not just acceptable, great. Does a great deal include multiple solutions sold? Does it include certain T&Cs if you need to adjust those or change them? Does it include inclusion of your services or maybe your customer success team? Does it include tracking of metrics we help them achieve? However you define good, give them the details beyond solution and price, right?

In the area of process, what do we owe them guidance on? Well, most of us have a sales process in place. We've got to have the processes that not only define what those are, but hold people accountable to executing them. This is not the time to get freelance. We put processes in place for a reason, make sure people are held accountable to execute them. From a qualification standpoint, let's give our team the processes that allow them to qualify opportunities based on the most contemporary version of the guidance. If we've defined what good or bad looks like, let's make sure that people are qualifying accordingly.

And lastly, we have to have processes in place that hold frontline managers accountable to managing the process, not just managing the deals. These processes are defined to find... To be able to help us move forward, we've got to make sure our frontline managers don't become super sellers, they stay managers of the process. I love that they can sell. I love that they know how to get deals done. But let's have them do that within the parameters of the process we've identified.

And then lastly, from a discipline standpoint, let's make sure that we've established that cadence for opportunity coaching. In other words, to provide a discipline that ensures those processes that have its check-in or opportunities early, to make sure they're aimed at the right way, let's make sure that we've put organizational discipline in place to conduct those on a regular cadence. Just a normal part of our management operating rhythm. You know that operating rhythm. We forecast monthly. We hold weekly team meetings, weekly. We conduct regular opportunity coaching sessions. It's just the way that we roll so that we maintain this discipline to make sure we apply the guidance in the process at all times.

Now that's kind of a high level view. So what does good look like in organizations that have this in play? Well, what good looks like is a nice interchange between win-loss reviews and opportunity coaching or remember win-loss reviews, the benefit. We got the clarity of hindsight. We know exactly why we won or lost. The challenge is you can only leverage that insight on future deals. You can't do anything on this one, and that's where opportunity coaching comes in. Let's put a system in place that allows us to take those insights gained from our win-loss reviews and channel them into our opportunity coaching on current deal pursuits, right? The benefit there, we could leverage those insights so that we stay focused on the winning trajectory, and we're operationalizing those insights from guidance, process, and discipline, right?

When you think about it, a win-loss review and opportunity coaching, they share a lot of similar structural points. They're both focused on customer business issues. They're both focused on understanding the key decision makers, the political landscape. They're focused on how we stack up and differentiate against competitors. They're focused on how we differentiate and all that. So there's a lot of similarities between the two. It's just one is designed to be able to capture insight that we can leverage into the next one. All right?

So with that in mind, let me start wrapping things up. Creating that great win-loss deal strategy through guidance, process, and discipline. It looks like distant execution before teams pursue. All right? Ensure that your prospecting and expansion opportunities are aimed at high gain targets of yours. The business, the customers, the segments that you want to win. The more we're aimed at that kind of business, the more we're likely able to win those kinds of deals. We also want to make sure we're providing the team guidance on what good and bad looks like so they can factor that into their business development activities.

Now during deal pursuits, let's make sure we're absolutely targeting our selling activity on setting up a good opportunity, that kind of opportunity we want to win. How do we do that? Give them great qualifying guidance on how to qualify according to that definition of good. And then lastly, put in place opportunity coaching as a normal discipline in how we operate our business, our operating rhythm, right? You get those things in place in the pursuit of opportunities, you increase the likelihood of leveraging that great insight you gain from your win-loss analysis.

So to wrap this all up from Force Management, to create your own win-loss deal strategy, it's all about creating alignment relative to the guidance you provide to your customer-facing team on what good looks like. You might even also sneak in what bad looks like so that they can avoid it. It's all about proactively managing the process to ensure the deals that you're pursuing are on that winning trajectory, or at a minimum, do it early enough that you can make some course corrections as needed. It's all about ensuring discipline across your entire organization, not just the field organization, your entire organization, to execute on the guidance and the process you've put in place.

Oh, listen, thanks for your patience and attention during the session. I hope you got some tangible ideas on how you can get more value out of your win-loss analysis. If you want some more information on how to operationalize those insights from your win-loss analysis, you might want to consider viewing our Create and Capture Value Webinar that's been noted in the footnote of my slides here. Now with all that said, get out of here, take these ideas, and go win more of the kind of deals you want to win.