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Win/Loss Blog Series: Pitfall #1 - Not Getting Sales Buy-in

Welcome to a new series of blog posts where I [virtually] sit down with subject matter experts to discuss the pitfalls and best practices surrounding comprehensive win/loss programs. These interviews and blogs will help provide excellent insights and guidance when building or expanding your own win/loss efforts!

In this interview, I’m speaking with win/loss expert and practitioner Ken Schwarz about how to get sales buy-in, one of the key issues in running a win/loss program.

Ben: Today, I’m kicking off a new series of chats with Ken Schwarz about some do’s and don’ts of running a win/loss program. Ken, for as long as I’ve known you, you’ve been involved in win/loss.

Ken: Yes, I got started in win/loss back in 2008, when I ran the market intelligence program at Progress Software. I ran similar programs at Pegasystems and HPE SimpliVity, each time refining the approach and expanding the scope. Richard Case at PSP Enterprises did our customer interviews. Hundreds of them. Then, in 2019 I made a big career change and became a win/loss consultant myself. I bought PSP--the company--from Richard Case and since then have been working with Richard and the rest of the PSP team to do win/loss for my clients.

Ben: You liked the service so much that you bought the company?

Ken: (Laughs.) Yeah, it’s true! It’s great to be interviewing buyers and advising clients after being a client myself. I find that I draw from my experience on both sides.

Ben: Well, I can appreciate that because I ran win/loss for VMware for many years, so I’m really excited by doing this series with you. But today, let’s talk about some of the mistakes you see people make in setting up or running a win/loss program.

Ken: Sure. There are several common pitfalls that everyone should be watching for that we can talk about over time. But today, let's start with the big one. The number one issue facing most programs in my experience is not getting enough buy-in and support from the sales organization. Whether you, as a win/loss program manager, are calling customers yourself, or using a consultant to do it for you, cooperation from sales reps is critical to both getting interviews done as well as making changes based on what you discover from the interviews.

Ben: Absolutely, this was a challenge for me in my career as well. We came up with a number of strategies to deal with it, but I feel at the end of the day that a big problem is that corporate asks the reps for a lot of special project help, and that they start to tune out anything that distracts them from their main business of selling. What’s your ask from the reps?

Ken: Yes, you have to keep the asks to the bare minimum. The most important ask of the reps is to validate that the deals you find in the CRM system were in fact competitive and that you have identified the right people in the accounts to contact. That’s because for a win-loss interview, we are generally looking for deals where the client competes for business to the bitter end--win or loss. So, no add-on deals or renewals and no early disqualifications or cancelled projects. We want to talk to the head of the selection committee, the person who knows the details of the decision. The rep is going to know if the deal is appropriate and who we should speak with. Sometimes that’s accurately and clearly recorded in the CRM system, but unfortunately that’s the exception more than the rule.

Ben: But if you ask the reps to do this, isn’t there some risk that they will cherry-pick deals?

Ken: Yes, that’s a good point. In fact, that’s why I don’t recommend asking the reps for “nominations.” Rather, it’s best to develop a list of deals from the CRM system and review them with sales management first to get their priorities and then the reps to validate and get the contact information.

Ben: Unfortunately, in my experience anyway, Salesforce CRM records can be pretty inaccurate. This was a major thorn in my side running win-loss! Often you couldn't tell from the records who to call, how to reach them, or even if the deal was a good one for a call or not. What do you recommend?

Ken: This is exactly why you need to validate the deals and key details on who to reach with the reps one way or another. We could do a whole blog on this topic, and how to make a repeatable and efficient process to do it, but you have to assume that the records will be inaccurate and will need the help from the sales organization to pick appropriate deals, identify the right contacts for a potential interview, and make sure that details like phone numbers and email addresses are correct. Nowadays, desktop phone voicemail isn't used as much any more--people just use their mobile phones--but the mobile phone numbers aren't always in Salesforce. It's definitely a problem. So yes, you are going to have a good relationship and communications with the sales team to get this info. But even if the information in the CRM system were perfect, I think it's still a best practice to check with the sales rep before doing any customer outreach so that the sales rep feels assured that the program isn't "spying" on their work. Trust is essential.

Ben: How about the reps? Do you interview them as well as the customer?

Ken: Absolutely. I like to schedule a short debrief with the rep before speaking with the customer so that I can better prepare for the call. I like to find out what business and technical issues motivated the purchase, what my client offered, who they were talking to, and if there were any surprises. All good background. However—and this is really important—I don’t ask the rep to tell me why he or she won or lost. In part, that’s because I don’t want to be biased going into the customer call, but mostly because it’s not a reasonable question for them. They are not mind-readers! Coming out of a competitive negotiation, it’s to be expected that customers would not share everything they were thinking, and especially in losses they are often in the dark. It’s my job find out for them why they won or lost when I talk with the customer.

Ben: What do you ask the reps to tell the customer before you interview them?

Ken: It depends if the interviews are blind or non-blind. If they are blind, then the customers won’t know who we are working for, so of course they mustn’t tell the customer we are calling. But if it’s non-blind research, then often the reps will introduce the customer to us, and we follow up. But blind or non-blind, our interviews are always anonymous, so any identifying information of the customer and the rep is redacted. This is very important so that both customers and reps feel comfortable to participate.

Ben: Yes, I've done both blind and non-blind. In Europe, due to privacy rules, we did them non-blind. But blind everywhere else. They both worked, but I always thought that the blind ones were most compelling, especially for sensitive questions around things like pricing and the performance of the sales teams.

Ken: Yeah, it’s definitely easier to get customers to speak openly in a blind interview. But it is much harder to get them on the phone without the rep introduction! So, they’re more work for us, but in the end, worth doing if you can. There will be no doubt that you get information that you cannot get from the reps. Over time, as they see these interviews, the reps come to appreciate how valuable they are.

Ben: But when you are starting you, what can you do? Getting traction with reps, especially in the beginning, was the hardest part in my experience.

Ken: I’ve come to see that the key is organizational buy-in and a good communication plan. Usually, win/loss programs are run by people in marketing or product management, not sales. So, the first step is to make sure at the outset that the executive sponsor for the program is aligned with the executive leading the sales organization and that there is buy-in at that level. Then, have that sales leader send out communication about the program to the whole sales organization, making clear expectations for participation by the reps and the benefits that they should expect. In addition, the win/loss program manager should address the sales management team in a leadership meeting as well as the sales force in a general sales meeting. It might require several meetings. Shortcuts here are usually pennywise and pound foolish.

Ben: Yes, this has been my experience, you've got to have top-down alignment. Working without that air cover can be impossible. The reps won't pay attention, or they'll help you once and then their interest dies. That's why we've had incentives for the reps, and that has helped as well.

Ken: Yes, that’s very smart! Spiffs help get attention but they also show the reps that the program is to be taken seriously. Like we were talking about earlier, reps get LOTS of requests from headquarters for all kinds of work that subtracts from their selling time. It’s common for reps and their direct managers to get jaded. You need to make sure that reps understand that their managers are watching their participation in win/loss and that it’s taken seriously, or you can have a very hard time getting their attention and cooperation. Reps can be expected to sell and to do what their line managers ask them to do. Outside of that, it’s all pro bono and no matter how well-intentioned, programs that depend on reps volunteering time and energy to special projects are frequently doomed.

Ben: Anything else?

Ken: Yes, one more thing: make sure that reps get a copy of the transcript of the interviews. It’s just human nature to feel nervous if there’s a report about you that you never see. You must win the trust of the reps with the program and the best way to do that is to promise them and then give them the transcripts. Anonymous interviews can be shared without fear of embarrassment. Once you get these in their hands, they will see how valuable the program is to THEM and they will become your biggest supporters. They will start to proactively reach out to you with contacts for win and loss interviews because they want to see the results. The management buy-in communication plan is much more critical during the first few quarters of the program or when there is a change in senior management. After that, it becomes self-sustaining.

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