3 Strategies for Jumpstarting Stalled Deals

Posted by Chris Ceballos on June 4, 2018

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When sales cycles drag on, as they often do, it can be a real test of patience. At some point, whether your product is stuck in procurement or the subject of a continuously rescheduled meeting between decision-makers, you want an answer—even if it's negative—to at least put you out of your misery and allow you to move on.

But if you gave up every time the sales cycle dragged on longer than expected, you'd probably never make your number. Lengthy sales cycles are an unfortunate reality, but how you go about navigating them can help determine when—and if—you finally seal the deal.

Our Emissaries, former executives from companies like Kellogg's and Refinery29, tell you what to do from the outset to prevent lag later on and how to win back momentum when your deal stalls.

Free trials can set you free

Your prospect’s done their research, and if your solution is more expensive than the rest, they’ll know it. Hesitancy around pricing has a tendency to halt sales cycles and kill deals entirely. While you may not always be able to lower costs, that doesn't mean you should give up. Our Emissaries suggest offering a free trial or pilot to break out of pricing purgatory and keep things moving.

“Trials and pilots give buyers the opportunity to see more about the actual service. Based on that, you can determine if you can go at a regional or global level for a solution. That's really helpful before you're signing a global deal,” said the former VP of IT at Kellogg’s.

While the initial reveal of your solution's cost may have given your prospect pause, if you can prove that greater cost means greater value, they'll be much more willing to sign on. Yes, you may be giving something away for free, but with current free-trial conversion rates over 60%, that's a bet worth taking.

Communicate (and address) your product's shortcomings

No product is perfect. So when selling, it may seem intuitive to avoid discussing where your solution falls short. But our Emissaries agreed that fighting this instinct and being transparent about your product's shortcomings often takes you further than just sweeping them under the rug. Sidestepping these talks may reduce resistance upfront, but it can lead to a longer sales cycle later on, if buyers become wary about your product's newly discovered drawbacks. Being honest about where your product is weakest will help shorten the sales cycle and build the crucial trust you need to close the deal.

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But where do you go from there? After all, you just exposed your product, and everything about it is now out in the open, warts and all. Whatever goodwill you acquired through this show of good faith can only take you so far, and buyers will need reassurance that your offering has a backup plan built in to address its shortcomings.

“If you see in the RFP there’s a need you cannot satisfy, you need to look for other options. Especially when the requirement is specifically stated in the RFP, you need to get creative to fulfill that need. As a customer, it's really important to see that you have spent quality time putting together an RFP that really is going to meet the business need,” said Kellogg's former VP of IT.

Our Emissaries suggested getting creative and devise workarounds that address your prospect's major areas of concern when they're beyond your product's reach.

Is there some feature in their existing tech stack that could be activated to lighten the load? Or could you look to partner with another vendor on a combined offering that more fully addresses your target's needs. It's not the end of the world if there are areas where your product doesn't cut it, but you must act quickly to redress them.

Start a dialogue when they go dark

The sales cycle has gone on long enough. You haven't heard from your contact in weeks and at some point there's only so much you can do. If the buyer really wanted what you're selling, they would have bought it by now, right? With new leads in sight, the urge to simply jump ship can be strong. But, if you do, you could be leaving a potentially lucrative deal on the table.

Our Emissaries said it's crucial to reach out to your prospect at this point to reel them back in, but when you do, avoid spamming them with standard "just checking in" emails and messages. Open a more thoughtful dialogue with your buyer that clearly expresses your interest in learning more about their concerns.

“I told one vendor that I was hesitant because they were NYC-based, and that made them less responsive, so I was talking to an LA-based vendor. He said he was going to try harder, and he did,” said the former director of engineering at Refinery29.

It could be that your prospect was going to eventually communicate to you what was holding them back from pulling the trigger on a deal, but being proactive helps accelerate the process. By initiating this dialogue on your own rather than waiting days between correspondence, you'll have more time to understand the problem and develop solutions to ease your buyer's worries.

Executive Insights

Long sales cycles and drawn-out deals are some of the biggest challenges facing enterprise sales teams today. Fortunately, there are steps you can take to accelerate the process and increase your odds of winning the business. If your product's high price tag is scaring away buyers, offer a free trial or pilot to demonstrate how your product excels and that it's worth the cost. Get ahead of as many potential roadblocks as you can. For example, don't wait for your product's major weaknesses to be revealed down the line during review—be upfront and honest about them from the start. Discussing your solutions glaring holes, and providing solutions to address them, creates trust and is one less issue to worry about later on in the sales cycle. When communication with your prospect reaches a standstill, reach out and start a meaningful dialogue with them to learn about what's holding them back and address it.

Topics: Information Technology, Sales Intelligence