“We got (or lost) the order” – Now What Next?


Why having a sales “retrospective”  matters

Complex sales consume lot of time and effort of the sales team. A large deal win is a celebration, a large loss spreads disappointment across the entire team. Large losses are always dissected, broken apart and discussed. Month after month, meetings usually have an “order lost” item on the agenda. Most times, this is done in a mechanical manner. The prime reason of order lost is faithfully put as “Price was High”. While this may be true in some cases, it is certainly not the sole reason in all cases. Very few teams have a deeper and robust conversation on why they won or lost the business. Why a customer said “yes” to our proposal and another seemingly similar one said “No” is important to understand.

Lisa Earle Mcleod and Ian Gross in their article 3 Questions Sales Teams Should Ask After Losing (or Winning) a Deal published in Harvard Business Review dated June 24, 2023 spotlight three questions which should be answered after big wins or losses. 

These, according to McLeod and Gross, can improve future win-rates of the team, a critical element for sustainable business success

Here are those 3 questions: 

  1. 1. How would the customer articulate the value of their choice? 
  2. 2. Who was the most influential voice in and out of the room? 
  3. 3. Beyond price, what were the key deciding factors in the client’s decision?
  • 1. How would the customer articulate the value of their choice? 

This question challenges the team to go beyond the obvious, shifting the focus to how the customer would articulate the impact of implementing the solution, be it ours or our competitors’. 

The first important nuance here, is looking at it from the lens of the customer rather than ours. The second important nuance is that this question helps us become sensitive to the impact of implementing the solution (outcome) rather than just features and benefits. 

If an order loss is being investigated, it helps the selling organization to take a close, hard look at its positioning afresh. The positioning can be corrected and articulated in a more convincing way in future deals, ensuring better conversions.

There is merit in analyzing wins also. Doing an order-won retrospective reminds the sales team about the other departments which get involved in decision making, which the team may not be meeting as a routine process. Or it may uncover insights on what are the acceptable behaviors while selling to such customers.

  • 2. Who was the most influential voice in and out of the room? 

Complex deals usually involve a “Decision making Unit” (DMU). Analyzing this DMU in terms of decision-makers, influencers, gate keepers and end users is critical. Figuring out whose voice was the most influential in and out of the room becomes extremely vital. That was the voice which probably determined the “value” to the buying organization, by listening the proposal and picking out the most important feature, impacting the buying organization. 

  • 3. Beyond price, what were the key deciding factors in the client’s decision?

Of course, there is no denying that price is one of the important factors on which decisions are made. But it is not the only one. Decisions are based on what is seen as “value” by a customer. And this differs from customer to customer. The success or failure in a deal depends on how good the team gets in understanding what is perceived as value by customers.

All deals need not go through a retrospective 

The question remains as to which deals need to put through the retrospective lens. Not all warrant very close inspection. McLeod and Gross suggest one deal per executive per quarter. Such an exercise throws up interesting actionable insights for different functions in the company.

Key Takeaways – Sales retrospective of one deal per executive per quarter

The key takeaways we can pick up from the article is are:  

  • Analyze one deal won or lost per executive per quarter to get powerful actionable insights.
  • This will also help in gaining sustainable business results over long term 

The article 3 Questions Sales Teams Should Ask After Losing (or Winning) a Deal published in Harvard Business Review dated June 24, 2023 is here. 

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Author Information 

Lisa Earle McLeod is a sales strategist and expert in sales transformation.

Ian Gross is a go-to-market leader in the technology sector having served in technology and consulting majors. He is an MBA from University of Chicago, Booth School of Business, and a BA from University of Maryland




In Essence annotates published articles of value to the Sales Community. It is an effort to bring insights within reach of Sales Leaders in ways that enable quick assimilation and action. Mercuri International acknowledges the authors and the publications for the insights.

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