How to Conduct an Effective Win-Loss Interview

Title: How to Conduct an Effective Win-Loss Interview

Presented by: Clozd

Featuring: Jonathan Stevens, Consulting Team Lead

Date: June 16, 2020

Clozd's consulting team lead, Jonathan Stevens, shares tips and best practices for conducting effective win-loss interviews. Jonathan's team of consultants have conducted 1000s of win-loss interviews for industry leaders like Salesforce, Adobe, SAP, Patterson Companies, C.H. Robinson, and more.

Presenter

Jonathan Stevens

Consulting Team Lead, Clozd

Jonathan is a consulting team lead at Clozd, a leading provider of win-loss analysis services and technology. Jonathan's team has conducted 1000s of win-loss interviews for industry leaders across various industries including enterprise software, logistics, healthcare technology, financial services, and more.

Webinar Transcript

Braydon Anderson:                                    

Awesome. We would like to welcome everyone out to today's webinar. We're really excited to talk about how to conduct effective win-loss interviews. We are going to give everyone just a couple of minutes to jump on. We know there are a few stragglers out there, so we will start the webinar in about one to two minutes. For those of you that are here, this is a great opportunity for you to win some Clozd swag. Simply go to clozd.com/webinarsurvey. There'll be a two-question survey, just simply asking you how your win-loss program is going and we will randomly select five winners to receive an environment-friendly metal straw and a Clozd t-shirt. So go ahead and take that for the next couple of minutes and we'll get started here shortly.

Great. Well, thanks to everyone that took the survey. If you just jumped on, go ahead and still take that survey. It gives you an opportunity to win some Clozd swag, but for now let's get jumped into the survey, or rather into the webinar. So for all intents and purposes, this webinar is being recorded. We will actually distribute this to everybody that attended today's session. If you have questions throughout, feel free to ask. There's a chat box that you have just within the Zoom interface that we will get notifications and if you questions, we'll try to answer them either throughout the session or at the end. So in way of introductions, my name is Braydon Anderson. I run all of our operations here at Clozd and we're fortunate to be joined by Jonathan Stevens. So Jonathan is one of the consulting team leads here at Clozd and has conducted interviews for some of the biggest brands out there, and have been able to shape what a lot of our clients are doing to run their win-loss programs.

So, Jonathan, thanks for being here today.

Jonathan Stevens:                                    

Thanks for having me Braydon.

Braydon Anderson:                                  

Of course. So as I mentioned, Jonathan and I are really the two that help drive a lot of our win-loss programs and as I mentioned earlier, we've been very fortunate to work with some of the biggest brands out there and running their win-loss programs, which takes us to really the goal for today is to share the best practices that we have learned as we've conducted and run these programs for some of the biggest programs out there. So with that, John, I'll turn it over to you.

Jonathan Stevens:                                  

Thanks Braydon. As Braydon said, I want to discuss best practices and really the way we're going to break this presentation out is conducting, scheduling and sharing insights from win-loss interviews. The bulk of our focus is going to be on conducting, but you can't really talk about how to conduct them without focusing on scheduling and sharing, because that's a huge part of the entire win-loss process and really important to get right, to be able to do this well. So question number one, how do I conduct effective win-loss interviews? There's really three components to this that we feel are critical for conducting win-loss interviews. There's a couple of extra nuances, but for the purposes of today, I just want to talk about the main things that make an effective win-loss interview.

First, create the right interview guide. You can't go into these things cold, you have to design a guide with some questions, some topics that you want to address. That's critical. Planning is everything. Second, have a conversation. This isn't a phone survey. We want to engage the people that we're talking to and really have a conversation with them. And third, which may seem obvious, but for reasons that we'll discuss later, gets missed a lot of the time, we need to find out why the deal was won or lost. That's critical. Okay. So now that we've talked about these main points that create the framework for conducting effective win-loss interviews, I want to dive into each of them separately. So first, let's talk about creating the right interview guide. So ideally what you want to do is to create an interview guide that directs the interviewer to the questions that matter most. I've outlined this in a handful of do's and don'ts.

So first, what you want to do. Develop your guide around discussion topics. There will be a temptation as you start doing this to immediately just start writing questions, but it's really important to focus initially, what do I want to even talk about? What are the main topics that I want to address with this person? Typically, in a win-loss interview with a software type company that we work with, the main topics will be overview and origination, so in other words, why the deal was won or lost. What are some of the main drivers here? And then we'll dive into some of the more nuanced topics of product, pricing, sales process, competitor feedback, things like that.

That's not necessarily a tried and true list that has to be worked every time, but those are the main topics we typically use. Depending on your situation and your business, you might want to address different topics. So that's one that's really critical is think about these main things that will allow the interviewer to skip around if necessary and be adaptive in the interview. Instead of trying to follow a pre-written question script, they can go topic by topic and move with the interviewee as they discuss these different aspects of the deal.

Braydon Anderson:                                    

So, John, I'm curious then, you mentioned it's not a survey, it's a conversation. Do you feel though, like you lose some quantitative structure by having it set up in this format rather than having it be the exact same every time?

Jonathan Stevens:                                  

That's a really good point, and a lot of time academic market researchers will push us on this topic and they say, "Well, we want it the same way every time so these things are comparable." Well, there's a couple of fallacies around that. One, it's really awkward to do it the same thing every time, because you miss a lot of the critical feedback that people want to give, because you're going robotically question after question, instead of adapting to what the interviewee has to say. The other thing you need to remember is this is qualitative feedback. We're not trying to create something that's purely quantitative, replicable, statistically, significant. That can be done and we actually recommend that that's done in a post-interview survey. So the primary mode of research here is the win-loss interview. The post-interview survey is where you can collect that kind of quantitative feedback and get really rigid and that's what we do in most of our interview programs.

Braydon Anderson:                                    

Gotcha. Makes a lot of sense.

Jonathan Stevens:                                  

Yeah. Great question, Braydon. So the second do is crafting essential questions for each discussion topic with optional "drill-downs". The purpose of this is double-clicking. Basically people will provide interesting feedback. You want to know more, so arm the interviewer with questions that they can use to find out more and to really gain the richness that they're looking for out of these interviews. So let's say for example, that I said, "So tell me what did you really like about the product?" They said, "Well, the integrations were strong and it connected to one of our main systems that we need to work with." Well, that's a pretty vague answer. If you just go onto the next question, you're missing a lot of important data. You want to say, "Well, what are those systems? Well, what data did you need integrated and was it a one-way integration? Was it a two way integration? Was this something that this software had natively built or had an open API?" There's a whole bunch of drill-downs that you can use to find out more and get a lot richer feedback than just a high level initial question.

So let's move to the don'ts. So what we don't want to do and we already addressed this a little bit is create a rigid structure that must be followed the same way each time. If you do that, basically what you're doing is creating a survey that is done over the phone. That's something that really hasn't been done well for several years, there's other methods of doing surveys. The point of this is to have a conversation. A rigid structure in the interview guide will not facilitate a conversation.

Finally, don't design your questions the same way you would in a traditional survey. So traditional research surveys say things like, "To what extent did you like this product?" Typically, people don't speak that way when they're having a conversation in everyday speech, right? They may use colloquialisms. They use slang. You want to be professional, but at the same time, you don't want to seem overly rigid and formal to where the interviewee is uncomfortable because of the way you're speaking. So design your questions in the way that you would traditionally only speak in a professional manner.

So let's go to the next high level topic. The next key to having a good win-loss interview conducted, and that is have a conversation. So we want to conduct the interview like a conversation and be willing to adjust the approach as you go. One of the ways we do that is asking qualitative questions. Braydon addressed this earlier about asking quantitative questions, but one, those are really long, when you're actually doing an interview, you don't want to go through survey responses and options as you're conducting a win-loss interview. You want to ask them open-ended qualitative questions that allow you to get the rich feedback and allow them to give you an answer that really is crafted towards the question that you're trying to ask. So be qualitative, save the quantitative for a post-interview survey or for a broad customer survey some other time.

Another do, listen to the interviewee and be adaptive. The last thing you want to do is not listen and once the interviewee gives a great answer to a question, just move on to the next question without thinking about what they said and thinking about any potential changes in direction that you need to take, as a result of what they've said. So listen, be adaptive. Don't be afraid to totally change direction, sometimes multiple times, as you go through the interview. We do this all the time, and it really depends on what the interviewee is saying and what they deem was most important to the win-loss decision. So let's talk about a couple of don'ts. Don't conduct a phone survey. This starts with the interview guide as we've already discussed, but then as you're executing the interview, you want to make sure that you are going in a conversational manner. You're not asking question by question in the manner that you would a phone survey.

Braydon Anderson:                                  

Yeah, and John, I wonder, it just feels like it's more you want to ask open-ended questions rather than closed ended questions. Is that basically what you're saying here?

Jonathan Steven...:                                    

That's right. That's right. Don't ask yes or no questions. Sometimes the yes or no questions can be helpful if you have a really good follow-up question, but asking questions that start with why and how, those are the good types of questions. Don't try to quantify it by saying to what extent did you, or how often do you, or something like that, that it's going to give you a one word answer.

Braydon Anderson:                                    

Yeah, and I feel like part of that is to also stay away from scaled questions, like on a scale of 1 to 10, that should be kept for a survey, not for an interview.

Jonathan Steven...:                                    

Yeah. I mean, you can ask that, but it's just not the most efficient way and it's not the best use of you or the interviewee's time to ask questions that are scaled, in that way.

Braydon Anderson:                                    

Got it.

Jonathan Stevens:                                  

Save it for a post interview survey or another survey format. Then finally, don't ignore critical pieces of information by moving robotically to the next question. So this is the opposite of listening. You don't want to, when they give you a really interesting nugget of information, make sure that you double click into that. That starts with your interview guide and having these follow on drill-down questions, but make sure that when they give you some interesting information, find out more, because those are the kinds of things, as you're going to present to your executives about why you win and lose, those are the kinds of things that they're going to want to know. They're going to want to dig down and get to the details of what drove the decisions here. So that's number two, have a conversation.

Number three, and this was probably the most critical and often the most overlooked part of win-loss interviewing is find out why the deal was won or lost. At the end of the day, you want to focus on the core reason, why are you conducting this interview in the first place? If you don't really know why the deal was won or lost when you get done with this interview, you've wasted your time and you've wasted the interviewee's time, and often this interviewee is a high-level executive at one of your buyer organizations, and you don't want to waste their time. This is critical. It takes a lot of work to get them on the phone. Don't waste it. So how do you do that?

First, start broad and accomplish your core objective really. You might want to take the first minute or two of your win-loss interview to introduce yourself, gather a little feedback on the deal, but then say, "Why was this deal won or lost?" Or if you have a little bit more context, say, "What gave competitor X the edge in this deal," but ask it straight up like that. Don't beat around the bush, make sure you understand. Typically when you do, people will give you the main reasons why the deal was won or lost. What that enables you to do is direct the rest of the interview to those core reasons and not waste questions on things that just didn't matter and didn't drive the deal.

Braydon Anderson:                                    

Yeah, and I don't think it's to say that diving into these other areas aren't important. I think they are really important, but it's, if you can't answer at the end of that, I feel like a lot of people over bake these interviews and try to make them so complex when at the end of the day, you're trying to find out why a deal was won or lost, and so it's really just making sure you're focusing your efforts on finding out that core reason, and then everything else is just supplemental to that. Is that accurate?

Jonathan Stevens:                                    

Yeah, I think that's right, Braydon, and the interesting thing that you'll find if you do win-loss interviews right, that most of the other feedback that you want will come as a natural result of finding why the deal was won or lost, but don't lose sight of that core objective. So a lot of people use this for competitive intelligence. They want to find out what were the strengths of my company versus competitor A, what were the strengths of my company versus competitor B? Well, when you're talking about why the deal was won or lost, people are going to naturally volunteer that information. So you don't necessarily even have to ask it many times.

So second do, focus on topics critical to the purchase decision. And I put why, why, why here. So once you understand why the deal was won or lost, then focus on those topics and this goes back to your interview guide and organizing it in a topic-oriented format. You can focus most of your energy on those critical topics, and then drill-down, say, "Why?" Three times often, people often won't volunteer information, or sometimes they haven't even thought about really the deep down reasons why a certain decision was made until you ask them. So you need to walk them through that. So now for the don'ts. Don't get lost trying to capture obscure competitor or product details. So this speaks to what Braydon was talking about. Really specific nuances about products and competitors. One buyers often don't even know, they don't think about this nearly as much as you do, and you're not going to get as much of that from these interviews, as you might like.

And number two, if you waste your time on this, you're sometimes going to finish the interview, not really knowing why the deal was won or lost, which was the purpose of the doing the interview in the first place. Then second, don't assume the buyer thinks about your product as much as you do. So this goes back to that first point under the don't column, but basically very specific things about your product and about your competitors and what their product does that your product doesn't, the buyer may not even know. So you need to put yourself in their shoes and think about, "Okay, what do they really care about?" They might have just chosen you because you were the cheapest or not chosen you because you were the most expensive. To them, the nuances of your product didn't really matter that much. So think about that. Put yourself in their shoes, understand that they're seeing this from a completely different angle than you are, as the company that's doing the interviews.

So at a high level, those are some of the main things that you need to do, as you're going through and conducting win-loss interviews. That's what we do here at Clozd. We create interview guides, we have conversations and we focus on why the deal was won or lost. If you do those three things, you've already accomplished a great foundation for successful win-loss interviews. So with this in mind, the next question is, how can I efficiently schedule win-loss interviews? We talk a lot about conducting these things, but you have to get the right people on the phone in the first place. And it may seem easy to do that but once you start getting into the details of how you do that, it's not as simple as you initially may think.

So let's talk about some best practices to arm you with the tools to do that. So, as I said, getting the right people on the phone is half the battle. First, you need to gather a list of names and get appropriate approvals. Be strategic, think about the people that are actually going to have the answers to the questions that you want to ask, and then make sure that you go through the right channels to get approval to talk to these people. Often, that involves the permission of sales leadership. Be careful about doing this. We recommend having salespeople opt out instead of opt in. So to be more specific, give them a list of names and say, "Is there anybody that you would not like us to interview here?" As opposed to having them volunteer names for you to interview.

Braydon Anderson:                                  

So tell me more about this, John. Why can this be such a challenge? Like this sounds so easy, like gathering a list of names to go and interview, is it that easy or is it more complex than that?

Jonathan Stevens:                                  

Yeah, so it really depends on the organization, but we found that that's actually the biggest hurdle to getting win-loss interview programs done. There's a couple of challenges here. One, it's just the logistics of finding the names. Usually you pull that out of the CRM, but then once you have that, there's organizational hurdles. Salespeople sometimes don't want you to reach out to them. You need to get buy-in from critical people in your organization about this.

Braydon Anderson:                                    

So John, how do you even do that?

Jonathan Stevens:                                    

Yeah, so if you're waiting until you get the list of names to do that, you're already probably too late. You need to have buy-in when you first start crafting the idea for a win-loss program. People need to be bought in. Depending on the organization, it's going to be different people, but people in product, people in sales, sales operations, customer success, a variety of different people may need to know about this and they need to be okay with it because you're going to be going to some of the biggest customers that your company either has or missed, and there's going to be some sensitivity around reaching out to those people and there's going to be some sensitivity around the feedback that they might give.

So that's a big do, make sure you get the list of names and get appropriate approvals. So that's the first thing to do, is you need to get a list of names and get the appropriate approvals. After you've gathered a list of names and received the appropriate approvals, what next? You need to reach out to these people. You can do that through a couple of different channels. You can call them, you can email them, but then the next question is who does it? Somebody from sales, marketing, third party consulting firm, sales operations, there's a variety of ways you can do this. What we recommend is first emails are a lot more efficient than phone calls.

You might get to the point of calling, but start with emails. Most people don't respond on the first email. So you need to send multiple emails. If you're reaching out to 50 people, and you reach out to them five times, that's 250 emails. You can do that all manually, but what we found as the best practice, use some sort of automation tool. Use Marketo or HubSpot or Eloqua, something of that nature that allows you to automate this process and allows you to track who's responding and who's not responding. That's really important as you try to get responses from your invitations. Those are some of the things you should do, which leads us to the main don't. Don't try to do all of the scheduling manually. It is going to take a ton of your time, and unless you are doing this full time, like we are at Clozd, this is probably one project of many things that you have to do, you want to automate as much.

Braydon Anderson:                                  

Yeah, and I feel like, just from my perspective, this is something that people underestimate the amount of time and bandwidth it likely will take. Have you seen that as well, John?

Jonathan Stevens:                                  

Oh yeah. And in fact, that's often why people will end up hiring Clozd because they've tried to do this by themselves and they realize it's a ton of work and these are processes that need to be honed over time. So you can try to do it yourself, and granted, there are companies that do it successfully, but it's a big undertaking to really get it right. Making sure you sent emails on the right day, making sure your wording is right in your initial emails and follow up emails, making sure that you get the right people that you need to talk to. That's all a big process, and if you've never done it before, it can be extremely intimidating.

So, let's get to the point where we've scheduled somebody for an interview, we're equipped to conduct a great interview. How do we want to publicize our win-loss interviews and drive change in the organization? That's the whole point of doing this anyway, right? If we conduct these interviews and they sit in some PDF in somebody's Google drive somewhere, they're not going to do anybody any good. So this is the final step and arguably the most important, right, is how do we drive change? Here's some best practices for sharing the win-loss feedback. Like I said, gathering win-loss data is pointless, unless you can effectively communicate it to the people with the power to take action.

So one way you need to do that is record and transcribe the interviews. One big mistake people make, as they're starting out a program like this is they create their interview guide, they go through their interview and they take notes as they go, but the notes are never going to be complete. They're never going to have all of the information that you need to really gather the richness of the feedback you get from the interviews. And furthermore, nobody's going to believe you, because you're not going to have direct quotes from the buyer. So if you go say, "Oh, the buyer said this," they're going to say, "Well, prove it to me. Where is their quotation?" And you're not going to be able to provide them with anything. So it's really useful to use a recording tool. There's a lot of things like that. Zoom, GoToMeeting. So then once you've recorded it, you want to transcribe it. You want to get into a document format so people can read it and consume the information more quickly.

There's a lot of great tools out there to help you do that as well, so leverage technology. So once you've recorded and transcribed the interview, so what? How do you get into a format where people can consume it? The entire interview transcript is actually going to be pretty long. Some people are going to have the time to read the whole thing, but if you want to get the attention of executives in the organization, you need to package it in a way where they're just seeing the most important parts of the interview. So the way we recommend to do that, and the second do for best practices for sharing is, develop a method for tagging and aggregating key themes across interviews. At Clozd, we've developed a methodology around this, and we have a handful of themes that we typically use and we also customize themes based on the clients that we work with, but for each interview that you do, you want to identify what were the key drivers that motivated this person to either purchase or not purchase here? That'll be critical.

Braydon Anderson:                                  

Do you have any examples of what some common themes are that you've seen John?

Jonathan Stevens:                                    

Yeah, absolutely. So we have a client where the APIs and integrations that they have on their product are a key reason people choose to purchase or not to purchase. So they make a software that hooks into a lot of other softwares and the other software that hooks into will be part of somebody's tech stack, and if it doesn't easily connect, they're going to choose a competitor. So APIs and integrations may be one. On the sales front, empathy and communication is one that we see. A lot of these interviews, people will say, "The sales person just didn't really listen to me and it was so frustrating that I just decided it wasn't worth pursuing this anymore." That's a classic example of sales, empathy and communication. So typically these themes are going to be centered around your main topics that you create in your interview guide, but it's good to have sub themes that really identify the specific nuances of why the deal was won and lost. Pricing themes, themes about the company like M&A issues or macro economic challenges that they're running into.

There's a variety of different themes that you can use, but at a high level, the most important thing you want to identify is what are the main reasons this deal was won and lost and be able to track those across interviews, which is why you're tagging these themes in the first place. So let's say I tag three themes in an interview. I tag five in the next interview. I have three in the third interview and one theme is consistent across all three. Well then you're starting to see a trend here and you're starting to see some evidence of something that's either a core reason why many of your deals are won or lost and that's something that executives can take action on.

Braydon Anderson:                                  

Do you have any recommendations for how many themes I should be tagging per interview?

Jonathan Stevens:                                    

Yeah, that's a really good question, Braydon. So there's not a magic number here, but typically what we find is three to five is the general range that we see. The reason for that is because usually there's not just one thing that's driving these deals and that's a mistake that a lot of people make, they think, "Oh, it was just because of price," and a lot of CRM win-loss feedback that sales reps fill out, will require the sales rep to attribute only one reason for why the deal was won and lost. There's often multiple reasons and there's often positive and negative reasons. So there are things driving the person to buy and driving the person not to buy.

Braydon Anderson:                                    

So you're saying one interview could have positive and negative themes?

Jonathan Stevens:                                  

Yes, absolutely.

Braydon Anderson:                                    

Interesting.

Jonathan Stevens:                                    

Depending on the strength of those themes, the person chose to purchase or not purchase. You can have a loss where there's only one negative theme and five positive themes.

Braydon Anderson:                                    

And is there too many themes?

Jonathan Stevens:                                  

Yes, that's a really good question. If you put too many themes in here, which is a mistake a lot of times people make, when they're first starting to do this, what you end up with over the course of 10, 20 plus interviews, is you have all of these different things, and you actually don't know why you're winning and losing at the end of the day, because you've tagged everything under the sun that the interviewees have said.

Braydon Anderson:                                  

Yeah.

Jonathan Stevens:                                    

So when you're tagging these themes, focus on the critical drivers that influence the outcomes of deals.

Braydon Anderson:                                  

Yeah, you're almost creating a long tail at that point, rather than letting things boil up and see what actually is emerging to the top. It feels like if you tag too many themes.

Jonathan Stevens:                                

Yeah, exactly. You just get a bunch of data that doesn't allow you to make decisions. So here's the do's. Don'ts, don't only take notes of the interviews. We talked about this already. There's a lot of reasons for it, and don't share only a data dump of the interview transcripts. I've actually seen this done, but basically somebody will do a bunch of win-loss interviews. They will take PDFs of all those interviews, word for word, and then they'll give it to people to read. That's going to be a lot of work and nobody's going to take that much time. You need to have summaries of each interview and then tag themes that you find in each interview with the company in quotes. That will enable the people that are consuming the data, to see it in a much more concise package and a much more actionable package. So make sure that once you do these interviews, you package it in a way that's digestible and actionable for people so they see analysis, not just interviews.

Braydon Anderson:                                    

A follow up question I have there, John, is, are you seeing typically clients and individuals running their own programs are wanting to deliver these insights, do they just do a quarterly project and then deliver it? Are they doing this on an ongoing basis and still delivering it every quarter? What are you typically seeing there and what would you recommend?

Jonathan Stevens:                                    

Yeah, so that's a good question. So Braydon, before I came to Clozd, I worked for a great consulting firm that did a lot of good work and they did a lot of interview-based projects like this and basically the final deliverable that they created was a big PowerPoint deck, 50, sometimes up to 60, 70, or more slides, and they delivered that to the client and they said, "Here's what we found."

There's a couple of problems with that. One, it's a lot of information to consume, it takes awhile, and it's not timely either. You might be delivering this three to six or more months after the actual deals took place. So what we do at Clozd is every interview that we do, we tag themes, we write a summary and we push it out to our clients so they can see, as soon as we did the interview.

Braydon Anderson:                                    

Instantly.

Jonathan Stevens:                                    

Yes, instantly. They can see the outcome. So this might've been just a few weeks after the deal was actually closed. So you can start to take action on these interviews in the upcoming deals instead of waiting three or more months, and then by that time, the feedback that you get might be obsolete anyway. The timeliness of this is critical. So having a drip of these interviews coming in and understanding how you win and lose so the client organization can adapt as they're receiving the information is critical.

Braydon Anderson:                                  

Awesome.

Jonathan Stevens:                                    

So that's it. Those are some of the best practices. We talked about conducting interviews, scheduling interviews, and sharing the feedback. We hope this was useful, and I'll turn this time over to Braydon.

Braydon Anderson:                                    

Yeah. Thanks, John. This has been awesome. We really appreciate you jumping in here and giving us some of these thoughts and sharing your insights from doing all these programs. So we have some additional resources. The first thing is you can download our definitive guide to win-loss right now. Pull out your phone, pull out your camera and just scan this QR code on the right, and that will take you right to our page to download the win-loss guide, so feel free to download that. That gives you a lot of great insights. You can reference our blog Clozd.com/blog. We have a lot of great work with Pragmatic Marketing as well. And lastly, email John. He'd be more than happy to answer any of your questions. That's Jonathan.Stevens@clozd.com. We really appreciate you taking the time to join us today and hope everyone has a great day. Thanks a lot.

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