This past Monday, after six months of hard work, I got hit with a deal-killing email from a major enterprise prospect.
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Let me set the stage...

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It's Monday morning and I've just returned from a week-long family vacation, and a very long 15-hour drive home (with kids) the day before.

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It's a super busy week ahead, I have a full meeting schedule and as a bonus, I have less than a day to prepare for my upcoming QBR (Quarterly Business Review) with my Founder and executive leadership team (woohoo!).

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But despite all of that, I was feeling recharged and ready to hit the ground running and then, suddenly, it happened...
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A new email hit my inbox. Subject line: "Final Decision"

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To paraphrase the email: Jesse, we've made the difficult decision not to move forward in partnership. For blah blah blah reasons. You were such a great resource and partner, and this decision has nothing to do with you or your product. In fact, you should get a raise for being such a badass Sales Player in this process.

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(Okay, I might have made up that last part about giving me a raise and to be real, only a small % of my buyers have ever taken time to learn about Sales Players).

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To say I was crushed would be a huge understatement.

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How dare they send me a canned rejection email after six months of A+ effort and hard work.

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I ran multiple calls a week, delivered several custom demos, negotiated a no-brainer proposal that aligned with their budget, brought my Founder in to meet with the team, deployed a TON of internal resources to help with the evaluation including an airtight mutual action plan.
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I ran almost every sales play I know on this deal cycle, but in the end I lost.

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Why am I sharing this?

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Now that I've had some time to process everything and do a post mortem call with the prospect, I can confidently share what I think is an important lesson in our line of work:
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​You can do everything right and still lose.

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This is a tough pill to swallow, especially early on in your selling career, but it is the absolute truth. You can run a perfect deal cycle — sell your value, multi-thread, do exec-peering, handle all objections, structure a no brainer deal proposal and there's still always a chance you will end up walking away empty handed.

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This is why the ability to detach from the outcome will be critical to your long-term success in tech sales.

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Now, with all of that said, let's talk about the silver lining.

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This might sound crazy, but every lost deal is actually a new opportunity. It's a chance to review your current process, team, skills and playbook.

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It's a chance to reflect on the small things you might have missed along the way. It's a chance to check yourself and make sure you didn't have "happy ears" with the prospect.

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It's also a chance to get aggressive and find a way to backfill the lost pipeline (I was fortunate to have another deal enter my pipeline with the potential to backfill the loss).

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Losing deals is part of the game.

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Unfortunately, many sales leaders and most sales influencers will never open up about their losses. I guess they probably think they won't sell as many courses or brand deals if they are transparent about how much they actually lose.

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The result of this is an echo chamber of reps who believe that if you just follow the script, the process or buy another sales book or course then you will always win.

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This is not reality.

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If you've read this far, you're in for a treat. Without revealing the details of my deal and prospect (a brand you've 100% heard of) I'm going to quickly share my learnings from losing this deal. Here goes:
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Ultimately the decision had more to do with a MAJOR shake up across the enterprise. In fact, the project was fully cancelled, so I didn't lose to a competitor (phew).
​✅ Lesson: I should have worked to get higher up in the org earlier on since it's likely senior execs would have been aware of this big shake up.
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​Throughout the deal, there were some signals that I noticed, but ultimately ignored. One example was senior decision makers missing key meetings and being disengaged in certain parts of the process.
​✅ Lesson: I could have trusted my instincts and named the emotion during calls with my champion. "Hey why do you think your VP didn't show up for the business case read-out last week?"

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This was an exciting deal. 6-figure proposal, a well known logo and an eval team that I enjoyed interacting with in the cycle. Because of this, I likely developed happy ears or the tendency to only focus on the good news I was given by my champion.

✅ Lesson: Bring a healthy amount of skepticism to your deals. Buyers might tell you everything is on track and it's just a waiting game. Behind the scenes, they may be facing budget cuts, competing priorities, internal politics and any number of other things that could kill your deal.

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In closing, remember that it's not enough to be right. You can run a nearly flawless deal cycle and still lose.

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The big lesson here is for every lost deal, there is an opportunity to tighten up your process and work to get a little bit better.

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I hope you enjoyed reading my candid thoughts on losing deals and here's to your success building on your losses to create wins.

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-Jesse