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February 25, 2016

You Win Some, You Lose Some: Learning from Win/Loss

John Timko
Vice President, Marketing Strategy
ConnectWise, Inc.
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Your sales team wins and loses deals every day. How often do you stop and really look at those deals? I know you’re busy, but when you don’t take the time to review your wins and losses, you miss out on the wealth of information that your customers and prospects have already shared with you.

What Happened?

Making sense of deals won and lost happens best through a win/loss analysis. Start by conducting short, pointed interviews with your most recent deals, both won and lost, to get to the bottom of their final decision. From company history to their first introduction to your company, through the entire sales cycle, and finally to their end decision, you can learn so much from just 15-20 minutes on the phone. Gathering this data can help you discover organizational shortcomings, better ways to sell, and why people are really buying (or not buying) from you.

8 Simple Rules

Pragmatic Marketing maintains 8 rules for a successful win/loss analysis. I conduct win/loss interviews 3 times per year and in my experience, most of their rules are spot on. There is one I particularly disagree with though: Outsource if necessary. According to Pragmatic Marketing, outsourcing should happen if a non-sales environment cannot be maintained during the interview.

While I agree that involving sales in any capacity during these interviews is a bad idea, I think you lose out on some of the vital findings when you outsource. Even hearing the inflection in someone’s voice (a sarcastic tone, perhaps) can mean all the difference.

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4 Even Simpler Rules

I have learned so much from our customers and prospects through win/loss analysis, and have developed a few rules of my own:

  1. Make it quick.

When clients or prospects say yes, try to get them on the phone before they’ve had the opportunity to find something about your company they may shift their fresh opinions. If they’ve said no, catch them before they’ve moved on and forgotten about you entirely.

  1. Let them talk.

In almost every single one of the win/loss calls I have done, the customer has quite literally told me their life story within the first minute of the phone call. All it takes is the first question, “So, can you tell me a little bit about your business?” and I usually get about 80-90% of what I’m looking for just in their answer.

  1. Be patient.

If they aren’t chatty, probe a little. Don’t be pushy, but try to word your questions as open ended, to avoid simple, one-word answers. You will get stronger responses that are jam-packed with good sound bites, rather than a yes or a no.

  1. Ask for a follow up.

Case studies are great to have in your arsenal of marketing assets, because they put real-world scenarios out there for people to see. During your win/loss analysis, if you feel like the conversation is going well, ask if they would be interested in a case study phone call 6-9 months down the road. If they agree, ask them to start tracking the important metrics you want to measure against so that you’ll get some hard numbers to utilize later.

Win/loss analysis has to be one of my favorite parts of being a Marketing Manager. I not only get to chat with our target market, but I get to hear the good, bad, and ugly. Then I get to take on the challenge of improving on them to ensuring our company and product are always moving forward.

Interested in what your customers and prospects are thinking, and how to use it to benefit your business? Watch the Webinar.

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John Timko Vice President, Marketing Strategy
ConnectWise, Inc.

As a former pitcher for the Detroit Tigers, John knows the importance of playing for the name on the front of the shirt instead of the back, so he’s always looking out for what’s best for LabTech partners.


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