Why I want my reps to lose more deals

This is a provocative title, so let me explain before you judge me as the worst sales manager in history, or accuse me of shamelessly bragging about my team winning too much.

I started running my first sales team almost exactly a year ago. To date our win rate has been over 90% we lost 5 deals last year out of over 70 opportunities. I should be proud of that stat but instead I find myself anxious, waiting for the other shoe to drop.

I hired a team of hungry millennials where our #squad was for most of them their first experience selling, we completely reinvented the product and our go-to-market strategy for a new start-up customer base, and we started encountering new competitors as we re-focused in a space we had previously neglected. Our win rate is proof that our choice to re-focus on the emerging tech space was a huge success for NetSuite and that our customers were ready for the product.

But is it wrong that I kinda want my reps to experience a really terrible loss?

The longer I’ve been in sales the more I have realized we learn a lot more from our failures than our successes. I can remember very clearly 2 monster deals I ran as a rep where I lost tremendously. I worked with them for months, we went through countless demos, I thought there was no possible way another vendor could have a better relationship with them, and they were going to be the deals that made my year from a quota retirement perspective- then I was completely blindsided when I lost! Well, maybe not completely blindsided, in retrospect my managers had told me for weeks that we had no chance of winning, but I couldn’t see past all the sunk costs I had already invested in the deal.

Today I have a graveyard/shrine of all my lost deals, a display of business cards on my desk from deals I have lost staring me in the face all day every day. In a sick, obsessive way I think back to those losses most days and try to make sure I learn enough from them that I can see the potential risks earlier and more clearly in current deals.

So why do I want my reps to lose more deals? They need to know what it looks like when you’re going to lose, and you can’t see it coming till it’s happened a few times before. I wrote a post a couple years ago about running out of fuel- literally my friend’s gas gauge was broken in her car, and she had to run out of gas and get stranded a couple times to figure out what the warning signs were so she could fuel up earlier in the future.

I love this analogy of a car running out of gas because you can always re-fuel. I can remember the days when I lost those deals feeling completely empty, like I had given everything I had to win the deal and wrestling with the knowledge that my best wasn’t good enough. It’s a difficult set of conflicting emotions to process as a young person especially when you have not faced a lot of rejection in the past. But you can always re-fuel. A new deal will come your way and you can recover and move on.

I know it’s inevitable, we will lose deals. I don’t know how to help my reps prepare for it, and maybe I can’t. My managers certainly tried their best to warn me and I couldn’t be reached. All I can do is celebrate the losses as much as we do the wins because we can learn so much more from them and those stories will stay with us a lot longer.

Kelli Lampkin

Kelli Lampkin is a writer, traveler, comedienne, and entrepreneur.

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