5 uncomfortable questions product marketers must start asking in win-loss interviews today

Win-loss interviews are one of the toughest parts of the gig, right? If you log a loss, no one is interested in dwelling on it. When you win, who has time for looking backwards? There’s not a lot of incentive to examine the process when sales is riding high and everyone be like:

So, why bother? Why devote valuable time to hearing a lost customer explain in detail why and how you failed? Because it will help you next time. If you do it right, it should almost guarantee a win the next time you’re selling in the same scenario — maybe even to the same buyer. It’s your job to understand where things broke down and how to fix it. It will probably be awkward. Get over it. Make them feel comfortable and get on with it.

Why

Why did they begin the process? They had a problem. They thought you had a solution.

Do you? Is there a problem with your messaging? Perhaps you need to look at the lead qualification process and implement training that level. Maybe your inbound content isn’t doing its job. It’a big waster of money and time all-around when there is a gap between what a buyer thinks your product will do and what it actually will do. That’s a positioning problem you need to fix right away.

Now, for the one that makes everyone squeamish, but it is hands down the most important question you can ask: “Why not me?” Why didn’t they choose you? They may try to deflect or give a generic (useless) response. But! You have to make them feel comfortable enough to be straightforward, so just be honest. This information will help you. You’re a professional who wants to be the best — so are they!

Who

Who identified the need in the first place? This is important because it tells you how important it was to them. If Evan a junior coordinator in a 200+ organization proposed a change, then chances are it was never a priority. They likely squashed the whole thing in favour of status quo-ing whatever was already in place. Sit down, Evan!

Who was involved at each stage of the process? Understanding the stakeholders gives you insight into where your personas are working and where they need to be updated. Increasingly, IT is weighing in on martech decisions. Marketing is managing sales enablement and a chief innovation officer (CINO) rules them all. It is crucial to manage messaging to the unique org charts appearing in enterprise level organizations. Win-loss interviews are a great way to get this information.

Who else was considered? Who made it to what stage in the process? This intel will help you categorize competitors based on their own success throughout the selling cycle. Does Company X consistently fall out during the demo stage? Do you always see Company Y on specific deal sizes or certain industries? Does Company Z kick your ass every time during discovery?

How

How did they research options initially? How did they become aware of your solution? Understanding where prospects are finding you and accessing your content will help define personas and build your content strategy. How did they build their shortlist? How did they make a final decision? Was it by committee or did one key player have the final call?

What

I kid, I kid…

But. You do need to understand what sent the deal in another direction. It’s often not what you think. Sales reps like to lay blame at the feet of Price. Marketing throw it back to Product, who pitches it to Sales again. (And they all secretly blame Management.) It could be as simple as qualifying gaps or as complicated as implementation timelines and required resources. Maybe your champion left or was influenced by evil forces? Perhaps your selling guides emphasize This but buyers are interested in That. It might be an easy fix or require a complete overhaul. The point is, you can’t fix it until you know what it is, and you won’t know that unless you ask.

When

When did the implementation begin and end? Does the timeline match what they expected? Does the budget? Ask questions about the post-purchase environment. Get a feel for the delights and disappointments they’re feeling. That intel goes directly on your battlecards and competitor profiles. It also primes you for another pitch, if the opportunity should arise.

There’s a good chance, too, that they didn’t make a decision at all. In that case, you’re in a great position to maintain the relationship and follow-up regularly without it seeming offside. Knowing this will also keep you from hurting your win rate with erroneous data.

It goes without saying that this is much more fun when you’ve won and you’re meeting with someone equally as flushed by the excitement of a New Thing. It’s still as important to find out as much as you can. You can uncover blips that, though they didn’t sink the ship, should be addressed before damage is done. It’s also the best way to find out about your competitors, so you can beat them again the next time.