How to conduct win-loss interviews

In their simplest form, win-loss interviews help you find out why a sales opportunity converted into a customer or fell from your fingertips. They take the guesswork out of the equation, put qualitative data at the heart of your efforts, and enable you to understand what is and isn’t working for you.

Sound like something you want in on? Awesome. Before you go in all guns blazing though, you need to know:

Who’ll take the lead,
What criteria to select people on,
How and when to reach your interviewees,
What questions to ask, and
How to record and analyse your findings.

We’ll be ticking off everything you need to confidently answer one to five confidently.

Why are win-loss interviews important?

If you’re not asking people why they did or didn’t pick your product how are you getting the answer? Guessing? Assuming? Generalising? Neither’s good enough.

It's imperative you are talking to your customers.

Getting to the root of people’s decision-making process helps you understand:

How you’re perceived by the market,
Where your gaps are,
The parts of your product people care about most, and
Which competitors win over you - and why.

With this kind of intel in tow, if trends emerge, you’re primed to act pronto which can only better your product and improve your future ratios.

Did you know: teams who consistently conduct win-loss interviews benefit from a 14.2% increase in win rates?

Somewhat contradicting that stat though, it’s said less than 20% of companies bother to actually invest in post-decision research. Why? Because they’re not seen to have actionable outcomes or prescribed templates and are often batted to the sales team - who offer up nothing but a one-word explanation in their CRM.

That number’s both good and bad though. If you’re part of the stat you’ve potentially got one-up on your competition but if you fall into the 80% that don’t conduct win-loss interviews, you’re 100% missing out.

If those stats haven’t already swayed you, here are a few more that ought to do it:

So, here’s everything you need to know to start implementing a successful strategy and win more, lose less.

Win-loss formulas

For the quantitative side of things (we’ll touch on this again at the end), the calculations you need are:

# won opportunities / # lost opportunities = win/loss ratio

# won opportunities / # total opportunities = win rate

Who's responsible for win-loss interviews?

To be truly effective, win-loss research needs to be entirely unbiased.

If customer A hates feature B you need to know about it. If customer C wasn’t keen on sales rep D’s approach that’s important. And if customer E already chose competitor F, sales rep G shouldn’t be using the post-decision discussion as a last-ditch attempt to win their business.

You can probably see where we’re going with this, but win-loss interviews shouldn’t be done by sales teams. You want and need the prospect/customer to give uncensored feedback in a sales-free environment and that’s really tricky to achieve if the person they’re speaking to was involved in the process.

Some popular and conducive teams who could take ownership include:

Product marketing
Marketing
Sales enablement
Customer success
Product management*.

The reason we put an asterisk alongside product management (PM) is although they could be a viable team to support with win-loss interviews, you may need to proceed with caution. Sometimes, PMs can be too focussed on the mechanics of the actual product and its features, so if you’re assigning some of your research to them just make sure they don’t go in with tunnel vision.

How many win-loss interviews should be completed?

There’s no set number but the more the merrier. We get resource can be tight though so to make the whole process more achievable, it could be worth building it into people’s schedule - for example, every Friday afternoon each responsible team member’s tasked with conducting two/three/four/etc. interviews.

The more manpower you’ve got the more you can collect but remember to only bring people on board who can be impartial, otherwise, odds are, you won’t squeeze all you can out of the opportunity.

If you’re super pushed for time and resource another option could be to outsource the whole process to a third-party. This will enable you to:

Ensure complete objectivity, and
Hit a guaranteed, set quota (by tasking them with X interviews per week/month/year).

Here are just a handful of companies who can help:

And while we’re on the topic of numbers, whether you’re running your research in-house or not, remember to get an even number of won and lost cases so your results aren’t statistically skewed. Naturally, it’ll probably be tougher to get lost prospects on the phone but that doesn’t mean they should be neglected, in fact, quite the opposite, more effort should be put into pinning them down.

Tip #1: if you’re struggling to get people to take part consider attaching an incentive to the call - a simple gift card will do.

Tip #2: you’ll almost never get a ‘yes’ from everyone you ask to interview so invite more people than you need. For example, if you want to speak to five people, ask 20.

Tip #3: make sure the people you invite are the decision-makers.

When to conduct win-loss interviews

The sooner the better. The longer you leave your interview the less fresh the person’s thought process and feelings will be and you want accurate info.

For deals you’ve won, try to make the conversation happen before the customer’s had a chance to get set-up with your product. That way, post-purchase events won’t weave their way into the interview or affect their perceived reason for choosing you.

Similarly, for lost deals, strike before the prospect’s embedded within a competitor’s product or service so their current situation doesn’t skew their memory or emotion towards you.

Anyway, to put a number on it, aim to conduct any win-loss interviews within four weeks of the deal converting or crashing.

Tip: aim to keep your interview length within 20 minutes. Any longer and you’re eating into people’s day too much and potentially putting them off.

Recommended methods for win-loss interviews

Without a doubt a phone call or in-person and there are a couple of key reasons for this:

Win-loss interviews rarely just go by the script. Yes, there’ll be a standard set of questions you want to ask (more on this next) but more often than not, someone’s answer will trigger another question or deeper digging and surveys don’t offer the opportunity to explore those openings.
By seeing and/or hearing the interviewee you can gauge their true inflections. Do they sound particularly happy or disgruntled? Do they give a long pause before answering? Do they sigh before mentioning event X? All can change the intent behind someone’s answer, all go unnoticed without human interaction.

Here’s how Andrew McCotter-Bicknell, Associate Product Marketing Manager at ZoomInfo powered by DiscoverOrg, streamlines his company’s process:

“I use Calendly to set up win/loss calls for my product team. The tool automatically syncs with each product manager’s Google calendars - that way, when a recently won or lost customer is open to having a conversation, there's little to no barrier in finding a time that works for both parties. While many parties are "open" to having a conversation, many don’t follow through if the process takes too long. We've found that once we implemented Calendly, most (if not all) parties scheduled time after confirming that they were open to having a conversation.”

Win-loss interview templates

While we’re on the subject of increasing uptake, don’t gloss over the words you use to invite people to partake - they alone can make or break your efforts, so make sure they’re simple, short and flexible - i.e. instead of giving someone a time and date, give them the autonomy to dictate the when.

Here’s some sample text you could use for prospects you’ve won:

Hi [insert name],

Thanks for picking Product X and welcome to the team!

We’re always working on ways to make what we’ve got even better for our customers and to help us do that, we’d love to talk to you about why you chose us over others.

The call will only take X minutes and we’ll just be asking you a few questions about how we’ve done so far.

If you’re in, you can book a time and date that suits you here.

Speak soon, hopefully!

Thanks,

[insert name]

And with some modifications, here’s a template for prospects you’ve lost:

Hi [insert name],

Thanks for looking into Product X and I’m sorry to hear you went elsewhere.

To help us learn and grow, we’d love to hear about your journey with us and how you felt we did - there’ll be zero sales pressure, promise!

The call will only take X minutes and you can book a time and date that suits you here.

Speak soon, hopefully!

Thanks,

[insert name]

And if you’re not getting the numbers you need, as with any type of email campaign, A/B test your text and continue to refine your message until you find that magic formula.

Win-loss interview questions

Before you start the interview, first things first, make sure you’re prepared and that means knowing the person’s name, job title, company, involvement, deal outcome and any additional notes left by the sales team.

The questions you then ask will depend on your specific circumstances, but here are a load you can use, modify or take inspiration from:

What were the main criteria you based your decision on?
Which pain-points were you trying to solve with our product?
How would you rate the personalisation of our marketing?
Did you read any reviews about our product before making a decision? If so, where did you find them? And how did they make you feel?
How would you describe the contact you had with our sales reps?
How do you think our sales reps could be better?
How do you think we could improve our emails?
How do you think we could improve our website?
How do you think we could improve our product?
Was there any collateral you wish you’d had but didn’t? If so, what?
How did you first hear about our product?
How do you prefer to research and digest information?
How did you feel about our sales process in terms of the timeline and touchpoints?
Do you think our product is missing anything? If so, what?
Who else was involved in the decision-making process?
What were your thoughts on our pricing? And how did it compare to other quotes out there?
What parts of our product did you like and dislike the most?
When you were doing your research, is there anything you thought we were missing that others had? If so, what?
What was the main reason you did/didn’t buy our product?
Which other providers did you explore?
What’s the reason you did/didn’t choose those providers?
When you were researching our product, how did you rate our collateral?
How would you describe our reputation in the industry?
Do you have any other comments or feedback you’d like to give us?

We briefly touched on it earlier, but remember, win-loss interviews aren’t prescriptive and whoever’s conducting them should be prepared to go off script. If you’re too focused on working your way through a templated set of questions you could miss out on some golden tangents and opportunities.

Tip #1: keep your questions open-ended. One-word answers don’t tell you much and the call will flow much smoother if you’re not constantly probing the interviewee to expand on their answers.

Tip #2: this doesn’t mean you can’t go off script, but keep your standard set of questions consistent so you can easily compare them and identify trends.

Tip #3: hopefully these are a given, but don’t get defensive or let your win-loss interviews turn into a sales pitch and do express your appreciation for the person’s time.

How to analyse win-loss results

If you outsourced your interviews the analysis should be done for you and the results hand-delivered. If you kept it in-house though, here’s what you need to do.

Step 1: pull your interviews apart

Go through all your recordings and notes and see if there are any patterns. Win-loss data isn’t about one prospect saying jump and you saying how high, it’s about spotting, understanding and reacting to trends.

To speed up the analysis of call recordings consider getting a leg up by using a transcription app - here are a few that come rated by PMAers and on G2:

And pay particular attention to things like:

Is there a specific feature we’re missing that’s causing us to lose deals?
Is our pricing a sticking point?
Is our sales process too long? Short? Pushy?

Step 2: set action points

Once you’ve identified a trend(s) it’s time to act by putting a plan in place to overcome it and improve your win ratio - and remember, your action plans should be nice and specific. So, for example, if the pattern you uncovered was lack of a feature, your POA might be to:

Understand the cost and resource requirements of introducing it
Depending on the scale of the feature, conduct further market research
Work out how it fares priority-wise against other tickets
Pencil out a timeline of what’s needed and how long it’d take
Pitch the new feature to key stakeholders.

Or, if the problem was your sales team was too pushy, the action could be as simple as running a training session on how long to leave in between prospect calls and emails.

And on a more positive note, if the consensus was your product is easier to use than anyone else’s, this can be highlighted in marketing materials and briefed to sales teams to include in their conversations.

There are tonnes of people outside of product marketing who can benefit from the insights gathered - like sales, marketing, product management, customer service and engineering, so don’t hold back on the communication front.

Turn your findings into a slide deck, include the good and bad, and make sure everyone knows the part they play in accomplishing the next steps.

Step 4: measure your metrics

To keep abreast of your win-loss ratios make a point of periodically (monthly, bi-monthly or quarterly, for example) running the numbers to make sure you’re heading in the right direction.

Try to marry your qualitative and quantitative data up so you can attribute future ratios to certain events too. For example, if you discover prospects don’t like the length of your sales cycle in March, implement changes in April and see an increase in your numbers in May, could the two be linked?

We said it a couple of paragraphs ago and we’ll say it again, communication is key. As well as helping others improve their way of working, by vocalising your results and the improvements they earn, you’ll increase business buy-in to the win-loss process as a whole and that can only be a good thing.

Got a question about your win-loss interviews? Or wondering how other product marketers go about analysing their data? Whatever’s on your mind, there are plenty of people in our Slack channel on-hand to help.

Want to learn more?

Product marketing is and always will be a customer-centric role. A core part of your job is to value the voice of the customer and advocate for their wants, needs, and pain points. It’s your responsibility to make them feel heard. Therefore, customer marketing is an integral part of what you need to do to ensure that you’re staying true to this.

The Customer Marketing Certified: Masters course has been designed to give you invaluable, practical insights into streamlining your customer marketing approach so that you can ensure that:

Your customers are happy,
Your products are the best they truly can be,
Your brand reputation is consistently positive, and
That you bring in increased revenue for your organization.

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