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Start Small and Don’t Surprise People: Tips From Our Win/Loss Webinar with Scott Frost

For the second installment of our new Win/Loss Wednesdays series, we had the pleasure of chatting with Scott Frost, who’s led competitive intelligence at Stripe, Adobe, and New Relic.

By the end of the conversation — which covered securing an executive sponsor, building relationships, and more — Scott had shared tons of tips with the audience. Here are 3 of our favorites:

  1. Start small
  2. Don’t surprise people
  3. Find out when your executive team has planning meetings on the calendar

1. Start small

You can answer thousands of questions with win/loss analysis — but you shouldn’t. If your program is in its early stages, you should focus on answering a few questions at most.

Why? Well, first of all, your job isn’t to deliver a lot of information; your job is to deliver good information. The more questions you try to answer, the harder it will be to produce high-quality data. And the quality of your data is never more important than it is in the early stages of your win/loss program. You have to earn trust.

Secondly, your stakeholders don’t want answers to thousands of questions. They’re not interested in knowledge for the sake of knowledge. They want information that will help them make the decisions they need to make and nothing more.

So start small. Work with your executive sponsor (watch the webinar to get Scott’s tips on securing one of these) to identify one or two decisions the company needs to make and then find relevant data. If you do a good job, opportunities to expand your scope will come naturally.

2. Don’t surprise people

That meeting on the calendar? The one where you’re going to present your findings to the executive team? That meeting can go one of two ways: It can be a productive conversation where smart people discuss viable solutions, or it can be an unproductive conversation where emotional people go down rabbit holes.

The former > the latter.

Scott’s advice: Circulate your slide deck a few days before the meeting. Give everyone ample time to process your findings. This will minimize the risk of people feeling caught off guard and allow the group to have the most productive conversation possible. Plus, you may get clarifying questions in advance, which will help guide the conversation. You’re prepared and your stakeholders aren’t surprised — win/win.

3. Find out when your executive team has planning meetings on the calendar

Again, the ultimate goal of win/loss is to help your executive team make decisions. And as you may know, they don’t make decisions willy nilly — they make decisions quarterly and annually.

Which means there’s a good time and a bad time to share insights with them. Sharing insights before they make decisions is good. After they make decisions? Not so good.

So find out when they’re going to make decisions by knowing when quarterly reviews, end-of-year planning sessions, and board meetings are going to happen — and plan your work around that. Again, your executive sponsor can help you here.

Learn how to use win/loss insights to train your sales team

In another installment of Win/Loss Wednesday, we discussed using win/loss insights to improve sales team performance with Sales Assembly's Brad Rosen and TruVoice's Nick Siddoway. Click here to watch the recording!

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Conor Bond
Conor Bond is on the marketing team at Crayon. If, for whatever reason, you were to rip his headphones off his head and put them on yourself, you’d probably hear Weakened Friends or Charli XCX.