4 powerful lessons I’ve learned from the most painful sales deals I’ve lost.

I truly believe that those of us in sales who love it and have made a career out of it will always be learning. In fact, I personally believe that’s what it really takes to be successful in sales for the long haul.


Because as anyone who has been in this profession for any extended period of time can attest, making a career in sales will never be a smooth ride. No matter what you do, you’re just not always going to get it right.  


I’m certainly no exception to that rule. While I’ve had my share of success over the years, I’ve also had my fair share of deals gone south.


There’s no question that some major deals I’ve lost hurt bad. But as I reflect on them from a distance these days, they’re usually the ones I credit for some of the biggest lessons I’ve ever learned both professionally and personally.


I’m certainly not advocating that you intentionally go out and make mistakes to learn lessons. But I do think it is a necessary practice for us as salespeople to do some serious dissecting of the things that go wrong so we can improve for the future.


So that said, I want to share a few of mine so you don’t make the same mistakes I have. Here are the 4 biggest lessons I’ve learned from a few of the most painful lost deals I’ve had in my career.


1. The power of discovery and rediscovery trumps all.


I think it’s safe to say that most people who read my content regularly know I have a very firmly planted “why” for what I’m doing these days – using my sales, startup and recruiting experience to help startups win at building/scaling sales teams.


That said, I was a bit foolish in early days of ATP on to assume that my background would speak for itself in this regard.


Quality is everything for me (it’s also why our clients love working with us). Where many recruiters opt to send a bevy of non-vetted people hoping they’ll stick, my process can take a couple of weeks on the front end to surface the right people (though it depends on the search).


And sadly, a miscommunication on expectations bit me hard when I had an opportunity to work with a potential client who had a few mishires to scale their sales team early on.


They were looking for help fast (like NOW). We spoke the same language and hit it off, but I made a critical error and neglected to ask them what their priorities were (quality vs. speed). And after I’d already invested a lot of time on my part, it turned out they ended up only caring about speed.


Needless to say, the deal fell through.


When all was said and done, it was okay that we weren’t the right fit. But shame on me for not embracing the power of true discovery and figuring that out ahead of time. I assumed because all of their verbal cues were on, they were expressing interest, and were wanting more that they were on board with the way I work.


But had I really spent time drilling into that it before we began, I could’ve saved a lot of time and energy for both of us.

2. Always keep the door open… it’s usually a timing thing.


It’s really easy for us as salespeople to be selfish. You know, when the end of the quarter is approaching and you’re still a little short… it’s so tempting to let the pressure get the best of you and to go “all in” on a prospect to make your numbers.


But I’ve got to be honest… you and I both know this rarely works. And most of the time, it ends up hurting us more in the long run.


I learned this very early on in my career when I was working within a very specific corner of the healthcare market. So many times, I’d have a fantastic meeting with a potential client where everything clicked – the product was a perfect solution, the client got it and was excited, and that chemistry we all crave as salespeople was totally there.


Then I’d send a proposal and it would come back with a “thanks, but not right now.”


I wish I could say it didn’t get under my skin, but I’d be lying.


It turns out, these particular buyer’s had a purchasing cycle that was all driven on a specific trigger event and there was just no way they were going to buy at proposal time regardless of how well-oiled my sales machine was. It wasn’t until after a few painful attempts where I got it wrong that I figured that out.


In some cases, it took almost 2 years of relationship building, connecting the dots for their business, being helpful, and staying top of mind to close a deal. It was incredibly hard work and it was nothing short of demoralizing at times to be turned down when I really did everything right pitch wise on each deal.


However, good things come to those that wait AND put in the sweat equity. And finally signing those deals taught me one of the most important sales lessons I’ve ever learned (and one that has been cemented in my head ever since): we always have to play on the buyers timeline NOT our own.


As the very wise Alessio Artuffo articulated, “Don’t treat deals as deals. They are projects. Sometimes they are programs. Think PM.”  I couldn’t agree more… if we get a no today, it’s critical to keep that door open and then some for the future.


Just because it’s a no today doesn’t mean that it’s a no forever.

3. There is such a thing as bad business.


I think we are often taught as salespeople to think every deal is a good deal. But simply put, this is a lie. And it took some trial and error as a new business owner to really see this for the truth it is.


Here at ATP, it’s CRITICALLY important that we understand who our ideal customer is and who we just aren’t a good fit for. After all, we’re dealing with scaling businesses and peoples lives/careers – and that’s not to be taken lightly.


So when a company that was growing their team by 3X (think lots of opportunity for me) was beating me up about one of my key terms that I’m afraid I’ll never budge on, I really found myself caught in a tough spot.


On one hand, I wanted/needed the business (I mean, that’s a lot of potential placements and revenue).


But on the other hand, I knew that if I want to have the kind of impact on a business that we’re capable of and insist on having for our clients (like every newly placed rep closing a deal inside of the first 2 months) I needed to have a mutual commitment to our partnership.


So when my contact at said company kept telling me to work with them on good faith and to trust the verbal agreement (this is not my first rodeo) I decided that I needed to step away. And it hurt.


But I didn’t feel so bad after I had a look into their Glassdoor reviews and heard through some back channeling that this was the epitome of the bad business I work hard to shield myself and team from.


Long story short, take the time to know who your ideal customers are and spend your time on the prospects who are the right fit for your business. Otherwise you’ll end up wasting all your energy selling to people who will never be excited to buy (and it’s critically important to do so if you want to grow).


(Note: Looking for more on this? This article from Entrepreneur breaks down 5 good ways to know if a client will be more trouble than they’re worth)


4. Don’t let your ego get in the way of progress.


I come from a family of sales masters who (along with extensive training) drilled the idea that “crushing” the competition was the mindset you need to be the best.


So needless to say, it’s a hard pill to swallow when I’ve made a great case, confirmed that it was made, confirmed the buyer was excited about the opportunity, mapped out the buyers in the process correctly, and my prospect would turn to a competitor for a lame reason that I knew would come back to haunt their business.


But as Simon Sinek posted recently,


“Our best competitors reveal our weaknesses. The goal is not to “beat” our competition but rather to improve ourselves.”


I can’t deny the wisdom in that statement, even though it’s been one heck of a hard lesson to learn over the years for yours truly,.


At the end of the day, we can’t control our competitors. But we can control ourselves. And I’ve got to be honest… as hard as it is to admit it out loud, I’ve failed to do this on more than one occasion throughout my sales career (but I have always kicked myself hard for it later).


My solution? I try to channel my inner competitor against myself instead of others, I find it a lot less work to improve. It’s much easier to absorb the lessons that life is teaching you when you own them than when your ego has you blind to the reality in front of you.


It’s not always an easy lesson to apply, but practice makes perfect!


What have you learned from the deals you’ve lost?


I’ve said it before and I’ll say it again, there’s a reason why we have two ears and one mouth. The ability to gracefully lose is just as important as the ability to win a deal. And the power of paying attention to the details and truly listening to feedback on some of what I’ve described above has served me incredibly well.


As any sales veteran will tell you, continuous learning is the most important skill to have in this profession, especially when things don’t go as hoped. Because those moments are some of the best chances we have to improve and progress as professionals in this field.


So that said, I’d love to hear from you all…


What’s the biggest lesson you’ve learned from a deal that hasn’t gone the way you wanted it to? Leave a comment below and help us learn!


-Amy Volas