8 tips for effective win-loss analysis

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Win-loss analysis is the practice of systematically capturing and analyzing the reasons why you win and lose sales opportunities which if conducted rigorously can help you confirm and prioritize both the strengths and weaknesses of your product or service offering.

This allows you to refine product strategy, increase marketing effectiveness, boost sales productivity, and foster org-wide strategic alignment - ultimately bolstering organizational success, and in this article, I’ll share eight tips for effective win-loss analysis.

My name's Andrew Peterson, I'm one of the founders of Clozd and I'm excited to write about win-loss analysis.

The back story

Prior to founding Clozd three years ago, I worked for eight years at a company called Qualtrics - that was recently acquired by SAP.

During my first four years there, I worked in sales leadership and then pivoted into becoming the General Manager of a new product line that we launched there. It was kind of like a glorified product marketing position, we didn't have a formal product marketing team or function at the time.

The founders came to me and said, "We want to launch a new product, we need someone to oversee the whole thing, own the revenue number globally for the product". I got a chance to pivot out of sales leadership and start being really closely involved in product strategy and marketing and sales. It was a really enjoyable role for me.

During that span, one thing that we were involved in implementing was win-loss analysis. For those of you who are familiar with Qualtrics, you probably know Qualtrics is a market research technology and feedback data collection company.

We had a lot of Ph.D. researchers on staff, we had strong opinions about how to conduct research and it came to a point when we got to about 500-600 employees that we noticed the executive team was always arguing about why they thought deals are won and lost.

Different executives would have their one anecdote or story that they would cling on to and then they'd hold post mortems after a key deal was won or lost, and try and get everybody in the room to argue about why they thought the deal was won or lost.

The birth of Clozd

We started to realize there was probably a better way to figure out why we're winning and losing than to just rely on these internal stories, this guessing, these post mortems, and we decided as a feedback company that we should probably go to our buyers and start collecting feedback.

Through that experience, through several years of implementing win-loss analysis at Qualtrics, we felt like there was something better that could be offered in the space and a few of us ended up leaving Qualtrics to found Clozd, and since we've been able to work with the product marketing teams at a bunch of great companies.

We work with the product marketing team at Salesforce, Twilio, Tableau, segment. Companies like CH Robinson - a big third party logistics company.

Win-loss analysis is primarily a B2B use case, but we do occasionally work with B2C firms like we just recently did a project for a private school in New York where tuition for these students is about $60,000 a year for a kindergartner. They wanted to figure out why they were winning and losing deals with the parents of those kids - we've seen some interesting stuff.

Hopefully today through this article, I can highlight some tips and best practices that can help you advance and mature in your win-loss efforts.

The first thing I want to do is just talk about what is win-loss analysis?

What is win-loss analysis?

The way we define it at Clozd is this - win-loss analysis is the practice of systematically capturing and analyzing the reasons why you win and lose sales opportunities.

Rigorous win-loss analysis will help you confirm and prioritize both the strengths and weaknesses of your product or service offering, enabling you to refine product strategy, increase marketing effectiveness, boost sales productivity, and foster org-wide strategic alignment.

You can see as you look at this image, why a lot of our buyers that we work with are product marketers. Sometimes we sell win-loss interview programs to heads of product, product managers, a lot of times we sell to sales leadership, sometimes we sell directly to the executive team.

But more and more we're finding that the buyers and owners of win-loss analysis are product marketing teams. That's because you guys sit so nicely at the cross-section of all of these things, product strategy, marketing, messaging, sales productivity and enablement, and trying to align the organization strategically.

In this article, I'll cover eight tips - really high-level tips for effective win-loss analysis.

8 tips for effective win-loss analysis

1) Acknowledge what’s at stake

The first one is really important. It's laying the foundation - you need to acknowledge what's at stake and why it's important to understand why you're winning and losing and have a system or process in place for tracking that.

You don't want to be like Qualtrics was, even though Qualtrics is a very successful company, you don't want to be in a position where you're just guessing or you're relying on internal anecdotes or latching onto one story from one customer to make big decisions.

Too many leaders rely on conjecture, assumptions, and anecdotes.

Knowing why you win and lose is mission-critical for your business and for the success of your product offering. Like I've already alluded to, too many leaders rely on things like conjecture, assumptions, and anecdotes.

Todd Berkowitz, who's a research Vice President at Gartner said this - he said a formal and rigorous win-loss analysis program enables better segmentation, product strategy choices, and sales enablement. Those that take a more comprehensive approach have seen up to 50% improvement in win rates.

What we noticed while we were at Qualtrics, and why we got so excited to leave and found Clozd, even though Qualtrics was on the brink of either going public or being acquired by a big company like SAP, was that as we looked at the various feedback programs that Qualtrics helps run for its clients, things like NPS or customer satisfaction measurement, or employee experience and engagement measurement, or discrete market research projects like product tests, or brand awareness studies.

Those are all incredibly important, but for a company like Qualtrics, we looked around and we said what feedback is most important to us as a business? For us, we really felt strongly that it was understanding why customers were or weren't coming in the front door in the first place.

Something like NPS can measure how happy or loyal they are as an existing customer. But win-loss is what helps you understand perception from the evaluation process and why people are deciding to move forward with your solution or not.

That's incredibly important, especially for B2B brands that are selling something of significant size or value.

2) Secure executive sponsorship

Once you acknowledge how important win-loss analysis is, and the impact it can have on all those areas of your business, the next step is to try and secure executive sponsorship, especially as a product marketer.

You've got so many different priorities, you've got a limited budget, if you can have buy-in from the executive team to help implement the program and fund the program initially, but then also to be ready to adopt the findings and feedback, that's going to be crucial for the success of the program.

Engage leaders

The best in class win-loss programs that we've seen are ones that are cross-functional initiatives, again, often led by product marketing, but they're very good at working and engaging with leaders from other functions like product, sales, marketing, and the C suite.

Pool budgets

We've even seen in many cases, companies pool budgets from multiple functions to fund the win-loss program, because it has so much impact for different organizations.

Product managers, they want to know what features to build, but they don't necessarily trust the loudest sales reps who are claiming that this one feature is the silver bullet that's going to help them win so many more deals, and then later they build it and they find out "Oh, that was just one customer that asked for that". So they're eager to find this out.

Sales leadership is eager to find this out so they can improve sales processes and enable sales reps better. If you're an entry-level salesperson at your organization, how valuable would it be to be able to go back and see the reasons why prospects were or weren't choosing your solution, and who else they were evaluating, and what sales reps successfully messaged on wins, and maybe where they came up short on losses.

It's incredibly valuable for many different teams.

Take each function into account

Then as you're building out the program, you can take into account these types of questions and goals and interests of the various functions to make sure you build a program that addresses all of their needs and answers all of those questions so that there's broader adoption.

And you can help drive more success and more revenue and increased win rates like Gartner talked about.

3) Get direct feedback from buyers

The third suggestion for you is to try as much as possible to go directly to decision-makers for their feedback. There are some instances where organizations build their win-loss analysis programs around sales rep feedback.

There's a funny quote here from Bob Apollo, who was an executive vice president of sales ops at a company called Sybase. He said, asking the sales organization to self-report on wins and losses, is as insightful as asking turkeys whether they might be inclined to vote for Christmas.

Sales reps, they have different motives, there's some self-preservation at stake, I've been in sales, I've been in sales leadership, I know how that goes, I've sat in post mortems where sales teams, sales leaders, and sales reps try to talk about why a deal was won or lost.

You just can't fully trust that insight. It's good to, potentially through your CRM or another mechanism, give them an opportunity to provide some feedback, and give their perspective on the deal, that can shine some light on some things.

Conduct buyer interviews

But ultimately, the richest source of win-loss insight is the buyer - going straight to the buyer to get their feedback is the best method.

Even though at Qualtrics, we were a survey technology company, we even recognized that the best method for capturing win-loss feedback from a buyer is to go and engage them in a conversation. Especially in a B2B context, these are significant decisions that are being made.

There's a lot of different stakeholders involved in making most of these buying decisions, and a lot of different moving factors, moving pieces that influence the buying decision, so getting them on a phone call where they can tell their story is a lot more effective than sending them a rigid survey instrument and hoping that you crafted the right questions.

The best ideal method for collecting win-loss insight is to go straight to the buyer and interview them.

Consider leveraging a neutral third party

Leveraging a neutral third party is a big help, if you can afford it, it's going to help free up your bandwidth, of course, for all the other things you're working on. It can be time-consuming to conduct these interviews on a regular basis, to get them scheduled, to have a methodology in place, to tag and track themes, and report those out to the organization. There's a lot to think about.

So it can help a lot with bandwidth, but more importantly, it's going to help with the candor on the part of the interviewee, if they know they're talking to a neutral objective third party as opposed to talking with an employee of the company.

At Qualtrics, we went out and we tried to find third parties even though we had great researchers inhouse that could have conducted effective interviews, we recognized it's better if we go out and have a third party represent us.

4) Prioritize getting started

As you think about implementing win-loss, if you haven't implemented it before in your organization, you can get into a state of paralysis really quickly because there's so much to think about.

Consider starting small

Just prioritize getting started, don't be perfect, don't think you have to be perfect right from the beginning, just start having some customer conversations post-sell and collecting some feedback. Starting small is better than never starting at all.

You can then improve the program over time. We've also found in situations where product marketers are trying to implement this for the first time at their organization, it might be a new concept to the rest of the org and it might take them a minute for other functional leaders to really buy into the program and why it's a worthwhile investment.

It can help to just start small and just start showing some output to get them engaged and excited and willing to invest in the growth and expansion of the program. Consider starting small, focusing maybe on one pocket or segment of your business, or one product line, and then grow from there.

Sanjay Puri is the VP of Product Marketing at Avalara, and he said this, "Just start the damn program. It doesn't matter how big you make it, start with a few interviews, 2/5/10/20 per month, whatever number makes sense for your business and budget".

5) Tag and track key themes

As you go out and start conducting these conversations, whether it's you or whether it's a third party on your behalf, make sure you have a methodology in place for tagging and tracking themes across these interviews.

Record and transcribe each interview

Some of the recommendations we would make would be to record and then transcribe each conversation. Don't just scribble notes down on a notepad and then try and aggregate your thoughts later and throw together a PowerPoint, it's gonna be a lot more credible if you can take quotes from the actual customers and incorporate that into your deliverables to the rest of the organization.

Tag positive and negative themes

Try as best you can to record and transcribe each interview and then tag positive and negative themes from each interview that influenced the buyers’ decision. As you step back and think through the conversation that you had:

• What were the major factors that were in favor of them moving forward with your solution or product? And,
• What were the major factors against them moving forward with your product and solution?

It doesn't matter if it's a win or a loss, on wins, you're going to find that there are positive and negative themes on losses, there's still going to be positive themes, even though you lost the deal.

That's one mistake we've also seen companies make is that on wins, they try to capture what went well and on losses, they try to capture what went poorly, and then neglect to recognize that there's positive and negatives in both cases.

Tag supporting quotes

Each time you tag a theme tag a supporting quote that gives context to that theme, that's going to be really powerful over time, as you start to see trends emerge, you start to see themes recurring over and over again across interviews, you'll then have quotes associated with those to go help you drive the conversation internally with the product team about that feature they need to build or with the sales team about that aspect of the sales process that they need to fix or whatever it might be.

Track and aggregate over time

Of course, have a method for then tracking these themes and identifying trends across the interviews. It can be a little bit overwhelming, at Clozd we've been building technology for this.

If you've ever had challenges with that, if you have an existing program in place, but you just don't have a great way to accumulate all this information and synthesize it, share it out with stakeholders across the organization, that's one way where Clozd helps out in addition to conducting the interviews, through the technology we've built for summarising findings and sharing them out.

6) Interpret the results in context

The next one is to interpret the results in context, apply proper context to these themes that you're finding. Analyze them, break them down by different metadata that you have, things like region, product, competitor, segment, it's really interesting to dive into the data and see how they vary across those different factors that are important to your business.

Don’t extrapolate

Try not to extrapolate, don't just pivot the product roadmap based on one interview that you did, obviously, you're going to want to wait and conduct a decent number of interviews and find recurring themes before you go and take action on that.

Explore themes by outcome

It's also helpful to explore the themes by outcome. When you first look at your themes, you're just looking at the collective themes across wins and losses. But when you break it down and just look at wins, it's really interesting to see sometimes as you compare that to the themes on losses that sometimes you might see the same issue pop up.

On wins, issue A is a strength and on losses, that same exact issue is a weakness. Then you can start exploring:

• Why is that the case?
• What's the breakdown internally?
• Why do some customers come out of the sales experience believing we're strong at this, and others come out of the sales experience thinking it's a weakness?

As I mentioned earlier, drill into themes by different metadata that you have.

7) Democratize the findings

This one's really important. Tip number seven is to democratize the findings.

Democratize is just a trendy word, we liked to use at Qualtrics for ‘share things widely’, make them transparent. Liberally share the interviews and the themes with stakeholders across the business, this is going to have a huge impact on adoption and the impact of the program and you deriving ROI from your investment.

Because the more people that have access to the feedback the better, even though there's going to be critical feedback in there, maybe about the sales team, maybe about the product itself, you need to have thick skin and just get the information out to the organization so that different people in different functions all have equivalent access and can go in there and explore it and find takeaways that they can then implement.

We see in some cases programs break down because one person is that single point of failure. They want to hoard the information and then use it politically in the moments that are right or that are advantageous to them individually. They don't just push the information out and make it widely available, and that limits the organization's ability to take action.

Drip feed information

Drip published interviews out to key stakeholders and leaders in real-time as they get completed. If you're recording them and transcribing them, and tagging themes and quotes, you could write a little summary, push those out as they get completed to key stakeholders so they can be reviewing them one by one.

Push relevant insights

Push relevant insights out to specific functions and stakeholders, regularly push out key product insights to the product team, push out key insights about the sales process to the sales leadership team and sales operations team. So on and so forth.

You may have a dedicated competitive intelligence team or you may be as part of your role the competitive intelligence person, put together battle cards based on information that you're discovering in these interviews. It's one of the richest possible sources of competitive insight as well because you're talking with buyers who just evaluated you against your competitors.

It's very, very rich to hear their perspective, their perception, based on having just gone through the sales process. Take that information and push it out regularly to the stakeholders that care about it.

Periodic executive summary reports

Develop periodic executive summary reports, make sure that you have a method to transmit this information to the executive team, whether that's a recurring meeting with them, or you review the results or a report that you get put together that pushes out to them. But don't be afraid too to put the executives on the published interviews that are getting dripped out.

Executives that see these individual interviews, it's a great way for them to feel more connected to the customer and develop more empathy, and to keep a pulse on what's happening in the sales trenches, and potentially take action.

Post-interview discovery calls

It's surprising how many individual interviews have actionable insight in them where the company could go address something. We just recently had a customer, I mentioned CH Robinson the big third party logistics company, their contracts are between $1 and $50 million each time and there was one case where it was a win and they were excited to hear the feedback, why did we win?

In that interview, they talked about how poor the implementation experience was and that they were thinking about leaving. That gave the executive team because they were plugged into the program and reviewing these interviews as they came through, it gave them an opportunity to go and address that and make sure that they kept that customer.

If you do have, like CH Robinson, huge deals, then you may want to consider having what we call discovery calls, but just basically action planning calls with the sales team and other people who are involved on that deal, to debrief about it and talk about that one single interview, and how you could perform better in the future based off of that feedback from that one deal.

8) Calibrate and expand the program over time

The last one here, tip number eight is calibrate and expand the program over time. We haven't worked with a single client that just from day one started with a massive expansive program covering every deal in their pipeline.

They all grow into their programs and they all continue typically to expand the program over time, most companies don't address win-loss analysis as a one-time thing that they just analyze it real quick and then move on to other stuff.

This is constantly evolving and changing and so our clients, they continue to run these interviews on an ongoing basis regularly doing a certain number of interviews per month or per quarter to have a discipline and rigor around this so that they're always tracking themes about why they're winning and losing deals.

They're seeing trends, seeing how things change over time. Even if you start small, that will help you established the practice, get buy-in and support from other organizations, other functions so that you can steadily grow the program over time.

Make continual improvements

Make continual improvements to your interview guide, the questions you're asking, your sampling strategy, where you're focusing, what types of deals you're interviewing.

Steadily expand your investment

Steadily expand your investment to cover more of your pipeline, in an ideal world, you would try and interview every deal that came through your sales pipeline, or that at least met a certain stage in the sales process.

But for most organizations, that's just not economically feasible. Our clients all tend to deploy their interviews strategically after a key segment, deals against a certain competitor, the new product line they launched, they really want to iterate quickly and address issues so they might focus the interviews there for a while.

We find that companies tend to get a little bit strategic about how they deploy the limited number of interviews that they're able to afford at a given time. But ultimately, the ideal scenario would be to interview every deal.

Monitor metrics

Pay attention to the impact that these interviews are having. One nice thing about win-loss analysis, if you compare it to other types of feedback programs is it's very closely tied to revenue generation.

If you implement a win-loss interview program for a particular product line, for example, pay attention to win rates over time for that product line to see what kind of impact win-loss analysis is having.

That goes back to what Gartner said earlier that they've seen and the research they've done that win-loss analysis has a direct impact on sales win rates, and ultimately on sales revenue.

If you are at a point where you're looking to implement win-loss, or maybe take the next step in your win-loss program, at Clozd we have a blog on our website that has a lot of great thought leadership content on it as well about the practice.

Thank you.

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