Tell Me About Your Biggest Sales Fail
Sales reps are a breed of human that hear “no” much more frequently than most. It’s an expected part of the role, what we collectively sign up for when we take on this (challenging) career.
In this profession, we’re (all, to some extent) notorious for talking about the wins.
The massive deal we closed.
That kick-ass demo we did.
The multi-year contract that just got flipped back from a name-brand logo.
President’s Club, awards, recognition.
Hell, we slam a gong when something goes our way!
But when you think about the frequency that we hear “no”, why is no one talking about their fails? We’d contend that you’re likely to learn a lot more about what goes poorly than what goes well. And the reality is, that sample size is a lot bigger, too.
Evangelist Pastor, Charles Swindoll is credited with saying, “I am convinced that life is 10% what happens to me and 90% of how I react to it.” You can apply this to many facets of your life, but for sales folks, this rings especially true.
Tell me about your biggest fails in sales, and I’ll tell you why you’re likely better for it.
One of my biggest fails
Here is one of mine:
I remember this one vividly. Fails — at least the big ones — tend to stick with you like this. Moments of impact where you wish you would have acted differently. Hindsight is the great equalizer of these experiences, but damn — in the moment, these hurt.
We were getting to the end of Q3. I was an individual contributor and part of an undeniably talented team, one that was at that point in the year top-5 across the company globally.
But here’s the thing: I was behind my number. My pipeline was strong, and I had largely carried myself — at least to that point — with an air of confidence that it wasn’t a matter of if, but when the pins started to fall that I’d be where I needed to be.
In the moment, however, it can be really hard to grasp that. When you’re in the trenches, it can get really easy to fall prey to the downsides of not seeing your name at the top of the leaderboard. Your peers are executing, why the hell can’t something go my way?!
I started feeling the heat.
One of my deals in particular was super solid:
The primary contact and decision maker was new in his role as a C-Level leader. This was something we knew as a company was especially valuable, with folks new in role converting at alarmingly high rates.
The contact had actually worked with us before in a prior role, and had negotiated budget for our solution as a part of his employment agreement — cha-ching!
I knew the company’s goals for that calendar year and the year thereafter.
We went really deep, understanding what his department was responsible for in contributing to those goals, understanding not just what they needed to do, but what would stand in their way, what their vision of how to solve for those challenges were, and both the business value and personal value associated with successfully pulling this off, and what was at stake if they didn’t.
The plan moving forward was clear; we had presented to the buying team three times, answered all of their questions, brought technical resources that spoke in fine detail as to where we would help, and the last stage was a board meeting. We knew what the board had approved in the past (and why), what they’d turned down (and why), and collectively felt like we were in a really good position.
The legal + procurement processes were also detailed rather thoroughly, and the expectation was that once we sent the agreement, we’d be no more than 2 weeks from contract signing and kick-off. In fact, we had mapped not just the evaluation, legal/procurement processes, but went so far as to map the entire first 8 months of their engagement with us post-contract signing.
All in all, I had run a pretty solid sales cycle to that point. It wasn’t perfect, but I had handled myself very professionally, and was well-positioned to win the six-figure ACV.
But again, I was feeling the heat.
My manager had pulled me into a conference room for a routine pipeline review. We went through this deal + the others that were ranging from the middle of the funnel down. Overall, it was a good meeting. But like me, he knew I was behind and was putting a bit of pressure on me.
“One of these has to pop, man.”
In spite of all of the things that I had going for me, I was feeling desperate. I needed something good to happen, a deal to “pop”, and I was going to go all out to make that happen.
I was hammering the contact with calls, emails, LinkedIn messages. I was leaving voicemails like someone who had been broken up with, begging for “another chance”.
After a week of this, my prospect called me back:
“Steve, what the hell are you doing, man? I told you that I’d get back to you after the Board Meeting. You know that’s in three days. Why have you called me 20+ times in the last 4 days? We were doing so well...”
My contact was calling me to the carpet, and while he wouldn’t say it out loud, I knew that I had diminished some of the credibility that I had worked so hard to win in the first place.
But my blinders were on. Still desperate, I offered a discount — a substantial one at that. There’s an old saying about negotiations and discounting, “You can always come down, but you can never go up.” I had beat up the deal size out of desperation, not because it was a critical element of winning the opportunity.
Flash forward a couple weeks from then, and I had won the deal. I was back towards the top of my team’s leaderboard (yay!) but I had learned a key, super valuable lesson:
Sales Reps Should Be Selfish
Selfishness is largely associated as having a negative connotation. How I’m about to apply it, however, is not negative. In fact, I’d contend that it’s about being “positively selfish”.
Sales reps and their managers — in theory — should have incentives that are aligned.
Reps have quotas. Managers do as well. The rep’s quota often times rolls up into the manager’s quota. Great alignment, right?
Not always. Here’s an example:
Rep = 70% attainment
Manager = 125% attainment
The rep is still fighting to hit their number, but the manager already has. For the sake of the example, let’s assume that until the rep hits 75% of their quota, they are only paid 50% of their variable compensation. Let’s also assume that the manager’s compensation plan has them make 2.5x in variable compensation for every dollar his/her team wins above 100% of their quota. Bolstered by overperformance by the team as a whole, the manager is sitting real pretty.
The manager isn’t necessarily wrong or using faulty judgment in wanting his/her direct report to win the deal as quickly as possible. “Time is the killer of all deals”, they might say. “Create urgency by extending a discount that gets the deal done this week instead of two weeks after.”
[Side note: “Creating urgency” is a total farce. We’ll explain this in a post soon!]
But the reality is that what might be driving this “urgency” for the manager is the fact that they’re already above plan, and the accelerator dollars will pay off in spades. Incentives drive behavior, and in this case, because of the compensation structure and attainment of the plan, the incentives for the manager and the rep are completely out of whack.
The rep, feeling that pressure from his/her manager discounts the deal. The prospect is happy, for sure. But did the rep really need to do that? In my case, I didn’t. I left money on the table for no other reason than I was feeling the heat of being a bit behind, not at the top of my team’s leaderboard, and acted out of desperation.
I should have been selfish. Now, I can’t prove it — but I sincerely believe that the deal would have closed without the discounted pricing. When pushed by my manager, I should have dug my heels into the sand and stood my ground. In spite of the fact that he was my boss, this was my sales cycle more than it was his.
I could have pointed to everything that gave me good reason to believe this. Objectively, this was a solid, late-stage opportunity. My manager and I had a great relationship and candidly, I believe he would have supported me had I been a bit firmer. The value was there. I knew the priorities, the challenges, decision-making criteria, allocated budget, the timeline — it was a textbook sales cycle.
But the pressure of it all got to me. By discounting the deal, it meant that I had to sell more in subsequent deals to achieve my quota. It also meant that my commission payment for this deal in particular was lower than what it could have been.