What to do when you lose.

Posted on May 31st, 2021 to Uncategorized

Last week I heard from a client who had lost a piece of business she was hoping to win. It would have been her biggest corporate engagement yet, and she was understandably disappointed. She had delivered a stellar proposal, navigated tough objections and was feeling confident about her chances of getting the contract. 

But it doesn’t always go the way we want. 

As a small business owner, I know you can relate. Even as a pretty darn good salesperson, I can relate, too.

I’ve sold many, many millions of dollars worth of products and services over my career in sales, and I’m very proud of that. However, getting there meant losing about ~3x as much business. 

The question isn’t if we’ll lose business, it’s what we’ll do when it happens. 

It’s healthy, in my view, to take some time to feel bummed. We work hard to serve our potential clients throughout the sales process, and when it doesn’t work out, it’s normal to feel exhausted, deflated and maybe even a little scared. After all, as a small business owner, you are your sales force — for this thing to work, you’ve got to win business.

But my hope is that you won’t stay down for too long. If I’ve learned anything over the past 20 years, it’s that we can learn just as much from the business we lose as we do from the business we win (sometimes more). 

The next time you’re ready to bounce back from a “no,” I’ve got three things I want you to do.

1. Reflect on what went wrong. 

Sometimes not winning the contract has absolutely nothing to do with us — forces out of our control render the proposal moot for the time being. However, it’s always a good idea to reflect on what part we may have played so that we can improve our efforts going forward. Years ago, I heard sales expert Jill Konrath speak on this subject, and I’ve used the following questions ever since to evaluate my losses.

Ask yourself:

  • Was I speaking with the right person? When we’re selling to companies, sometimes deals go south if we’re not working with the right internal champion. Was there someone better suited for this conversation in the organization? 
  • Did I really understand the situation at hand? Sometimes we make assumptions, move too fast, and fail to grasp our prospect’s reality before delivering a proposal — and this can be a deal killer. 
  • Did other priorities steal my spotlight? At any given time, our prospects are juggling a number of needs — did one of those other needs take priority? Is there anything you could have done differently to show the prospective client that your services are a “need to have” and not a “nice to have?” 
  • Did you show enough value? Showing value doesn’t start when you send a proposal. Rather, communicating the benefits of working with you is a steady drumbeat throughout the entire sales process — from warming up leads, to hosting powerful sales conversations, to supporting your prospects through the proposal and contract process. How well does your prospect understand the value of what you can do for them?

2. Keep nurturing the relationship.

According to Hubspot, 60% of customers say no four times before saying yes — and 48% of salespeople never even make a single follow up attempt.

Don’t let an initial disappointment keep you from future business. This stat reminds us that it isn’t over when a potential customer says “no.” Rather, it could be just the beginning of a fruitful relationship. Continue to follow up periodically, adding value to their lives and work. Show them consistent care and support, and look for the inflection points and trigger events that could signal it’s time to reconsider working together.


3. Focus on client attraction.

If I’ve said it once, I’ve said it a thousand times: There’s no rejection a full pipeline can’t fix.

What does this mean? Hearing “no” from a potential client will sting a lot less if your pipeline is full of other exciting opportunities. 

How are you keeping proactive at the top of your sales funnel? Are you actively engaging in warming up new leads, or are you sitting back and waiting for referrals? Understanding what works in your business to bring in new clients is the single most potent skill you can learn to feel steady, confident and safe. 


Please don’t misunderstand, I want you to win contracts, and I 100% believe in building your sales system and gaining the skills needed to year “yes” more than “no.” However, I also want you to normalize failure as part of your entrepreneurial journey, understanding that there’s much to be gained from the learnings of “no.”

If you’re ready to finally build a sales system that works — and to gain the confidence and resiliency needed to implement a strong sales approach — I encourage you to check out the Sales Breakthrough Mastermind here. We’re currently enrolling for the next cohort, and I’d love to connect with you, learn more about business, and help you plan your next right sales step.

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