Football is a complicated sport. There's so much strategy, talent, and agility required simply to get the ball from one end of the field to the other. It's a game that requires carefully laid out plans and perfect execution 99 percent of the time. The other one percent of the time is luck.

When football players throw a Hail Mary pass, it means they've given up on their original strategy and are relying on luck. The team's shot at winning the game is all but lost, and the only resource left is a desperate toss as far down the field as you can go. We admire the Hail Mary pass that pays off, pity the desperation of those that do not, and scorn the pass when the passer gave up too soon.

Sales resembles football in many ways, and the Hail Mary is a good example of this. The sales equivalent of a Hail Mary scenario is taking a desperate measure to regain an opportunity that has practically no chance of converting.

Sadly, unlike professional football players, salespeople far too often invoke a Hail Mary way before the game has ended.

Understanding What Truly Warrants a Sales Hail Mary

Sales is not a pure science, and intuition is a huge factor. For example, how do you really know when a deal is close enough to being extinct to throw the Hail Mary? Unfortunately, most people's intuition is clouded by an innate need to do something proactive when hope is fading. This predisposes them to do too much too soon.

So how do you make the decision? My advice is that you actually stop relying on sales intuition and make a decision based on fact. My calculus here is simple: The only time it's appropriate to "Hail Mary" an opportunity is when you have real, hard evidence that the customer is moments from signing with someone else.

If you know that a prospect is in the process of signing with one of your competitors, you know the opportunity is practically lost already. In those rare cases, a Hail Mary sales tactic is absolutely justified. And if you get lucky, it might just save your sale.

How to Turn a Hail Mary Into a Touchdown

The number one way to sway customers away from their commitment to another competitor is to establish new value. The first and most important thing that any sales rep in a tough spot should ask themself is: Is there anything I can offer them that I haven't already? Is there anything I can do to make this deal irresistible, even if it isn't what I would normally do? If the answer is yes, then you may just have your answer. If it's no, then you'll have to dig deeper.

Oftentimes in a deal, salespeople end up working with multiple different contacts at the customer company. In those situations there are often both allies and detractors. In a deal that's souring, it's likely that there is one person at the prospect who is being particularly troublesome and he or she is hiding from you, making it difficult to deal with those "reservations." In a true Hail Mary scenario, the play is to either force a confrontation with that person (which very rarely turns out positively) or go above that person's head--even knowing that if you do so and it goes poorly, you've likely hurt the relationship for good.

Earlier in my sales career, I was working to land a very large Silicon Valley-based technology company. It was a deal that I really, really wanted and my company in many ways "needed." The CFO of the company in question was incredibly opposed to using my product, for no justifiable reason that I could understand. I'd been working on the opportunity for nine months, had mapped the organization from top to bottom and nurtured my advocates and turned around my detractors (all but the CFO as it turned out). On the day that procurement presented the contract for final signing by the CEO (which had previously been described as a process-based formality), the CFO told me that he had strongly recommended that the CEO sign with my competitor, which would happen that day. His reasons didn't make sense to me and were different from any other objection he'd ever mentioned. Worse, I knew this was a terrible decision for the company I was trying to sell to.

I realized the deal was clinically dead so I picked up the phone and called the CEO of the company directly. I explained to him exactly what had happened and why I thought his company was at a disadvantage as a result. I was careful to remain calm and rational and to explain clearly and succinctly the advantages I thought our product could have for his company. I begged him to take a bet on me and my company and that if he wasn't personally satisfied with the decision in 3 months' time I would send him my commission check made out to his favorite charity. He didn't exactly agree on the spot but after a couple more weeks of wrangling with the CFO, we got the deal... and when I called the CEO three months later he told me I had earned my commission.

Making a Hail Mary in sales is an extremely risky decision. If it must be done, it should be done thoughtfully and strategically, with as much control as possible. Draw on as much data as you can to support your point. Be prepared for the likely consequences of it failing, but pray that it doesn't.