It’s hard to approach a client and ask the tough questions. But as salespeople, we have been taught to ask questions that really stretch us, such as: 


What do you want? 

What is your budget? 

What is it going to take for my company to win this bid? 

May I meet with the decision maker? 


However, the hardest question to ask is: Why didn’t we win, or why didn’t we get the deal? 


The failure to ask, “Why didn’t we win?” is killing companies because this is the most important question to ask. When you don’t win the account, do you ask the company: “Why did we lose? What could we have done differently? What would it have taken to win?”  


It’s really a human problem because no one wants to know the truth. It’s akin to the fact that no one wants to know why his or her baby is ugly. It’s like asking, “Why is my baby ugly? 


The failure to ask the question is stopping you from learning or getting better. You don’t necessarily learn from your wins. You learn from your losses, especially when it comes to sales.  

When you ask, “Why didn’t I win?” you get incredible data that you can’t get anywhere else.  


Why don’t we ask this question? The first reason is that no one wants to know. If we find out what’s wrong, we’ll probably have to go do something about it. Or, it could be something that we can’t change. In some cases, you’ll find out the reason for why you lost, and you’ll be happy that you lost.  


Sometimes the reason you lost is because it’s something that you can’t do. IKEA is a great example of this. They lose deals every day, and they are okay with that. They are not going to change who they are to make you happy. They specialize in furniture that is not assembled, and that is flat packed. It costs a lot to ship wasted space. Customers may not like this about IKEA’s model, but IKEA is not going to change. Apple is the same way. They lose a lot of customers because their products are part of a closed system. You can only purchase apps for your Apple phone from the Apple Apps Store. 


Another reason we don’t ask is that we’ve already been rejected, and we don’t want to be rejected for a second time. Most people say, “They’ve already said that they don’t want to do business with me. I don’t want to ask a second time and be rejected again.” It’s like asking a girl to prom, and she tells you no. Then you ask, “Why not?”  


We see it as a waste of time to spend more time on this type of account. After all, we didn’t win. Let’s just move on and go to the next thing. I can see the logic in that, but the challenge is that you’re missing a great learning opportunity.  


I don’t always ask this question, but as a senior leader in business, this is one of the most important things I have had to learn to do after I didn’t win a deal. I have to ask, “Why didn’t I win? What could I have done better?”  


I remember the time I didn’t live this principle out. It was about 2 years ago. I had the opportunity to present my proposal to a company to provide Scaling Up coaching for a year. I had developed an annual contract for this prospect who was is out of town, a long 6-hour drive from my home. After a grueling drive, I botched the presentation. I knew I could have done much better. I knew I wouldn’t get the deal because I fumbled my presentation.  


During my long car ride home, I evaluated my poor presentation and all the hard work my team had poured into winning this account. A couple of weeks later, the prospect called and said, “We went with another coach.”  I was so disappointed in my performance that I forgot to ask why I didn’t get the account. I assumed it was the presentation, but it was probably something bigger, such as what I was offering or the cost.  


I missed an opportunity because I blamed a presentation. Even I look back with regret at missed opportunities. Don’t let anything stop you from asking that question.  


After this fumbled proposal, I came up with some tricks to make it easier to ask the question. The first one is the easiest one, and it’s the trick I rely on. During the sales process, especially if it’s a lengthy process that involves a lot of work on my part, I ask the client for permission to ask the question later. I say, “If I do all of this and I don’t win, would you be willing to share with me why you went with another option? I also want you to tell me how I could improve.”  


Set expectations up front that you are going to ask and gain commitment that they will tell you, because this is the easiest way to get it done.  


If you forget to do that beforehand, ask the question later by appealing to the universal desire to get better. Call them and say, “Thank you for your time. I have one last request. I’m trying to get better. How I get better is by understanding why my company didn’t win. Would you be willing to review that with me?” Everyone wants to get better, and most humans want to help others improve.  


One final shortcut is to blame it on your boss. Just get on the phone and say, “I hate to bother you. I feel awful even asking this, but one of the things my boss makes me do is put down why we lost a deal. I can’t make something up, because he’ll know if I did. So, can I get a genuine answer from you in case he ever checks?” 


The hardest question to ask is, “Why didn’t I win this account?” But, it’s also the most important one. You have to implement this into your sales process today. After you lose—or even after you win—ask why. The answers may surprise you, but they will give you the data you need to get better.