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In Antifragile: Things That Gain From Disorder, author Nassim Nicholas Taleb explains that humans are not very good at making predictions. Instead of trying to guess about the future, a better and more effective strategy is to determine if something is fragile. Sales leaders often believe they will succeed in reaching their goals by ensuring their sales team has many more opportunities than they should need. This results in an incredibly fragile pipeline made up of mostly fragile deals.

The reason sales leaders and sales managers struggle to commit to a forecast is because they are trying to predict which deals each member will win and which deals will be lost. Regardless of what the salesperson or their client says about the deal, if your deal is fragile, you have a greater chance of losing it.

Identifying Fragility in Your Sales Pipeline

We will explore what makes a deal fragile by looking at certain things that suggest fragility. We will endeavor to describe what might make your deal more likely to win. This is my list, and I invite you to add to it.

Not Compelled to Change: The salesperson that called me to pitch me his software did not understand that I had no compelling reason to do something different. When a client isn’t compelled to change, a deal is terribly fragile. If you are a sales manager that loves a large pipeline, you are ensuring you have a fragile pipeline due to false and fake deals. When predicting the strength of a potential deal, ask the salesperson exactly what is compelling the client to change. Any lack of clarity surrounding the client’s motivations means the deal is fragile.

Delivery Model Fit: You have a higher price because it allows you to produce better results than your competitors. You know the client is known to be a miser because they are a low-price provider to their clients or customers. If the client’s model is low price and your pricing is more than they are able to afford, your deal is something more than fragile, even though the client would benefit from buying from you.

The Stakeholders Engaged: The number and titles engaged in the sales conversation can provide evidence of fragility. It may be okay to start the conversation with one contact, but if the second meeting finds your salesperson sitting across from that same person and no one else, the lack of additional stakeholders is evidence of fragility. It can be difficult to know who has influence and who doesn’t. But a lack of the titles that you normally find in meetings or no leaders means the deal is fragile.

Willing to Engage the Company: When we talk about enterprise-level sales pursuits, you need the company to engage with the salesperson and their sales champions, who are vertical and horizontal on the org chart. The vertical means you are working with the department that needs your help. The horizontal is the other departments who will have to be part of the conversation. The larger the deal, the more you can sniff out fragility if the people in the meeting are not representing other departments.

The Client’s Effort: If your contact agrees to do something and two weeks pass, you may be looking at a fragile opportunity. It may be that you are only getting their time so your contact can suggest they looked at three sales organizations, allowing them to choose the one they prefer. This evidence is underrated. If your contact is working to move forward, you have some evidence that your deal has a good chance of being won.

The Buying Process: You can ask this question in a way that isn’t self-oriented by saying, “Can you tell what we will need to help you through your buying process, and what your team might need?” Anything you would communicate in a self-oriented way can be better said by making it about your client and their needs. If you have no idea what the client needs to be able to buy, the deal is almost certain to be fragile.

Client Implementation Date: A sales leader who loves the pipeline may not love this evidence of fragility. When every date in your CRM is the end of the month or the end of the quarter, you can be certain the salesperson has no idea when the client will sign a contract and begin implementing your solution. If you ask a client when they will be able to implement, suggesting something specific, like Tuesday morning on the 17th, you can get information about when their team will be able to make a change. Not knowing when the client can take possession of your solution, the deal may be fragile.

The Number of Competitors: It’s not true that your opportunity stages allow you to know the percentage of your chance of winning. This makes you and your deal fragile. Perhaps your opportunity stage suggests you have a 70 percent chance of winning the deal, but there are still two competitors in this contest. This means your chance of winning is 33 percent. Using the opportunity stages makes your forecast fragile.

Strategies to Strengthen Fragile Sales Deals

Instead of looking at your opportunity stages, look at the number of the fragilities of each deal. The more evidence you have that the deal is fragile, the more likely it will be lost. This is a better strategy than trying to predict which deals cross the line and which will die in your pipeline. But what is more, by looking at fragility, you can do something to improve your chances of winning. Intervening early will also help you avoid losing due to the fragility of your opportunities.

Leaving this article, look at the deals in your pipeline and determine which deals are likely to become clients and which will not. If you want to improve your results and the way your team sells, this list will provide a way to project the future.


Sales 2024
Post by Anthony Iannarino on March 30, 2024

Written and edited by human brains and human hands.

Anthony Iannarino
Anthony Iannarino is a writer, an international speaker, and an entrepreneur. He is the author of four books on the modern sales approach, one book on sales leadership, and his latest book called The Negativity Fast releases on 10.31.23. Anthony posts daily content here at TheSalesBlog.com.
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