Episode #358: Brynne Tillman

Why You Must Ask Actionable Questions in Your Post-Mortem
Brynne Tillman


Brynne Tillman

Brynne Tillman is the LinkedIn Whisperer, the CEO of Social Sales Link, and The Modern Banker. For over a decade she has taught bankers, entrepreneurs, sales teams, and business leaders how to leverage LinkedIn for social selling. In addition, Brynne is the Co-host of the Making Sales Social podcast and author of The LinkedIn Sales Playbook, a Tactical Guide to Social Selling. 

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According to Brynne Tillman, a win/loss analysis—or in her words, a post-mortem—is about figuring out why you got a deal or you didn’t. You want to learn why your clients chose you. It also helps you understand the playing field even when you win. Most salespeople move on when they lose a deal. But if you don’t know why you lost a deal, you may continue the same behavior. So you have to ask actional questions in your post-mortem to make positive changes to win more deals. 

Outline of This Episode

  • [1:01] What is a post-mortem and why is it important?
  • [2:33] The insights you can gain from a post-mortem
  • [3:55] Common mistakes salespeople make with post-mortems
  • [6:21] How to make sure the feedback you gather is unbiased
  • [7:46] Best practices for conducting post-mortem interviews
  • [10:44] The role of technology in post-mortems
  • [12:08] Brynne’s top three post-mortem dos and don’ts
  • [14:08] Why you should never take a loss personally

The insights you can gain from a post-mortem

Just conducting a post-mortem isn’t enough. You need to ask questions so you can take the answers and act on them. Don’t waste their time on questions that don’t lead to change. Start with 3–4 key questions:

  • What made you decide to go with the other company?
  • Where did we fall short?
  • What could we have done differently?

The goal is to learn from the questions to improve the sales process. As a team, you need to look at all of the reasons you won or lost.

Common mistakes salespeople make with win-loss analyses

Brynne advises choosing 3-4 actionable questions. You don’t want to take up someone’s time because you’re asking them to do you a favor. Ask why they chose the other vendor over you. That will get you the real answer. It might be something you can’t take action on. Maybe the other vendor has a solution you don’t offer. But you need to know if there’s anything you can improve as a team member or leader.

Best practices for conducting win/loss interviews

Brynne prefers to conduct post-mortems so she can see someone’s face, make eye contact, and continue to build rapport. Brynne would rather be vulnerable and learn from her losses rather than continue doing something that is costing her deals. And conversely, she notes that if you don’t know why you’ve won a deal, you can’t teach others to do the same thing. 

She’ll try to conduct an interview as close to when they said “no” as possible. Brynne will tell clients that no matter who they go with they’ll receive great training. She’ll share what her strengths are. She’ll set the expectation that win or lose their business, she’d love to have a conversation about why. 

Why you should never take a loss personally

Brynne had a client who was part of a six-month vetting process where he ultimately lost the bid. He had been so certain he’d get it because of the relationships he’d developed with them. He did his post-mortem and reached out to quite a few of the stakeholders. 

He found out he lost because of his price. So he shared that there’s a chance that the company they went with might nickel and dime them on the backend. If that happened and they had a way out of their contract, he said he’d be there for them. 

Ultimately, he offered his help even though they didn’t choose him. Six months into their contract, they were getting overcharged. They paid a fee to get out of the contract to work with Brynne’s client. Had he not done the post-mortem, he never would’ve known any of that. He’d never have planted the seed. 

Resources & People Mentioned

Connect with Brynne Tillman

Connect With Paul Watts


Audio Production and Show notes by

Learn More About Brynne Tillman

Are there any books on or Win Loss Analysis that you recommend? Win/Loss Analysis: How to Capture and Keep the Business You Want 

In the field of Win Loss Analysis – Who do you most admire and why? Liz Heiman is the structural thinker behind Regarding Sales; a company focused on building B2B sales organizations that deliver extraordinary growth. 

What are your top ten questions to ask during a Win Loss Analysis – Your Golden Question Set? Sales Rep Questions… 1. Were we the right fit?

2. If yes, Did they choose another solution or status quo

3. What was your strategy for approaching this prospect? Cold call, warm intro, we’re they actively looking for our solution?

4. How did you identify and prioritize the prospect’s needs during the sales process?

5. What objections did the prospect raise, and how did you address them?

6. What feedback did you receive from the prospect about our product/service?

7. Looking back on the sales process, is there anything you would have done differently? If so, what? 

What are some of the most important metrics that companies should be tracking as part of their Win Loss Analysi s process? Are there any metrics that companies should be cautious about when conducting Win Loss Analysis?

1. Conversion rate can help identify areas of improvement in the sales process and identify why some leads are not converting.

2. Sales cycle length can help identify bottlenecks in the sales process and areas where the process can be improved.

3. Average deal size can help identify the most profitable sales channels and products, as well as help sales managers allocate resources more effectively.

4. Customer acquisition cost helps identify areas where the sales team is spending too much money and help optimize the sales process. 

Win/loss ratio helps identify areas where the sales team is performing well and where they need improvement. Reasons for wins/losses including feedback from customers on why they chose to buy or not buy from the company. This helps identify areas where the company is performing well and areas where it needs improvement.

Metrics to avoid: Anything that measures busy work activities While it’s important to track activity metrics like calls, emails, and demos, these metrics alone may not provide enough context to understand why deals are won or lost. Sales professionals should also focus on the quality of those activities, such as the relevance of the messaging or the effectiveness of the content and value that engages prospects and creates conversations with the right buyers. 5. How do you handle situations where a loss is attributed to factors outside of your control, such as budget constraints or unforeseen market changes? If the prospect is interested in your product or service, but doesn’t have the budget, provide them with alternative solutions. This can include offering a smaller-scale solution or suggesting a payment plan that can make the product more affordable.

Hobbies, Interests? Tennis and Sales Innovation 

How can our listeners contact with you? https://Linkedin.com/in/BrynneTillman 

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