How to recruit for Win/Loss Interviews

Designing Your Win-Loss Recruiting Program

Any team’s ability to run a Win-Loss Analysis program depends 100% on the ability to talk one on one with customers and prospects. Getting someone to agree to a long-form interview isn’t an afterthought in Win-Loss, it’s the basis for all the value ever derived from the program, and can take a surprising amount of craft and energy. We call this effort recruiting. Here’s how we do it, alongside some advice based on the last 50,000 (or so) outreach attempts at Kaptify. 

If you imagine the key insights you get from a Win-Loss Analysis program as gold, you can imagine the long-form interview content being the ore that you’ll extract the gold from. That ore is in the minds of users, past users, and those who looked at what you had to offer, but passed. The only way to get the gold is to get the ore. Which means capturing many many long-form conversations. 

Let’s say you set a goal to get 50 Win-Loss interviews. It’s time to do outreach. We’ve found three key things that make up a successful recruiting campaign. We’ll call these the three pillars of recruiting. When any of these pillars suffer, recruiting is hard and goals are missed. If all of these pillars are met, recruiting is easy and goals are exceeded.  

Pillar 1: Quantity

Recruiting is a numbers game. If you had a million contacts to go after, getting 50 would happen by accident. Easy. It’s simply a numbers game. Not everyone will respond, and depending on the type of recruit they are (current customer, past customer, someone who looked at your product but is now using a competitor’s instead), their response rate will vary drastically. More contacts = more bookings plain and simple, so go heavy on the numbers if you have them. 

Pillar 2: Recency or Familiarity

The more recently an individual has interacted with you, or the more familiar they are with you, the more likely they are to agree to a conversation. Imagine you’re trying to recruit someone who passed on your product a year ago. Although you live in your world every day, they do not. They’ve moved on and they might even struggle to recall much about the interaction with your sales or product teams at all. However you’ll still be living large in the mind of someone who is just concluding their selection process. Stick to reaching out to losses who are no more than 120 days old. The diminishing return hits hard as that timeline extends.

Having said that, if this is a churned customer who used your product for five years, they are very familiar with you and will hold onto the context of your product and relationship much, much longer. We call these people “high familiarity” churn customers, and they could be reached out to many more months after leaving your product. 

If a person is neither recent, nor familiar, good luck getting them to agree to a conversation. They simply won’t have the context to add value in a long-form interview.  

Pillar 3: Incentive

Some contacts are willing to have a conversation for free. But for a large portion of the recruiting pool, an incentive is what puts them over the edge. Think of it this way: if every contact was offered fifty thousand dollars at the conclusion of a 20-30 minute conversation, they’d take it. So going back to Pillars 1 and 2 above, with enough incentive, you could have a very low quantity of contacts and even low recency and familiarity, because every single person would agree to an interview. As you decrease this make believe incentive number, you decrease a contact’s willingness to set aside a significant portion of their day for an interview. Incentive matters for many people and will add energy to the effort. We’ve found $50 as a reasonable starting point, but the program will run smoother and faster if you offer a $100 incentive. If you believe in the value extracted from these interviews for the long-term health and revenue opportunity of the business, $100 is entirely reasonable and will go a long way in helping you hit your recruiting goals. 

In a nutshell, our advice is this: make sure your contact list is as big, familiar, and reasonably incentivized as possible. If those three things are hitting, you’ll land your interviews and create the basis for a winning Win-Loss Analysis program. 

If you want more advice or for us to do this for you, reach out.