Anticipate a No, Worry Early, and Follow the Map

Dean Gonsowski, CRO at Gimmal, shares his sales mantras and the secret to his bottom-of-the-funnel strategy.

October 02, 2024

By Dean Gonsowski

There’s an old sales mantra that goes: Expect the yes. Embrace the no.” Both notions are sound, of course. Initially, you want to be optimistic and oriented toward success—hence the expectation of a “yes.”  And at the same time, a “no” (of which there will be many) can’t be soul-crushing. So, you must learn to persevere. 

Also, a “no” today might not be a “no” tomorrow, especially if it’s handled gracefully.

But let me flip this axiom on its head… Despite its inherent wisdom, this saying appears to be best suited for a one-on-one sales process, where a single buyer’s “yes” is all that’s needed to consummate a sale. Unfortunately, in my line of work (as a CRO for an enterprise software company), there’s literally never just a single person who can simply say “yes” to a deal. Therefore, I coach my team to “anticipate a no.” The “nos” can come from anywhere. And with an enterprise sales process that routinely has nine or more disparate stakeholders, the divergence of opinions is often legion. 

The most common “nos” come from the finance department that says “no” to the price, presumably because it’s out of line with their budget. Or a “no” can come from the legal department that refuses to pay for software before it’s fully deployed. Or the challenge can come from procurement, which says “no” to year-over-year (Consumer Price Index-style) price increases. 

Fortunately, none of these issues by themselves are fatal, but they do take time to “whack-a-mole”—referring to the sometimes painful and often tedious dance of discussion and negotiation. Each “no” takes time to resolve, and with that loss of time, the likelihood of a successful closing diminishes. Hence, the even more famous “time kills all deals” truism.

How you anticipate these “nos” is certainly subjective, but one thing is clear: you need to deploy a “closing map” as part of your bottom-of-the-funnel sales process. The first challenge you’ll need to overcome is the rep’s hesitancy in putting a closing map in front of a prospect. Many AEs perceive this step to be too pushy. In my experience, however, if handled properly, it’s just the opposite, especially for prospects who don’t routinely buy enterprise software. 

The benefits* of a closing map are numerous and include ways to:

  • Uncover information about the prospect’s decision-making process.
  • Uncover risks that might come up in your deal.
  • Track micro conversions, including:
    • Hitting milestones to which they agreed.
    • Missing milestones without a good reason.
    • Missing milestones with a legitimate business reason.
    • The prospect updating the closing map between meetings.
  • Run processes in parallel to decrease your sales cycle (e.g., work with legal and IT concurrently).

*Kudos to the Maestro Group for letting me leverage their Closing Schedule Playbook (although we call it a “map”).

The exact format of the “map” is highly variable, but the core elements are what really matter. In many instances, the buyer simply won’t understand all the steps in the sales process, so without a closing map, your reps will simply be knocking down one issue at a time. This is suboptimal as it doesn’t account for any long poles in the tent, and it also doesn’t identify and prioritize any potentially fatal issues.

For example, if your prospect’s legal team requires a blanket “cancellation for convenience” term in the contract (which wreaks havoc with revenue recognition), and such a term will be categorically refused by your contracts team, it makes the most sense to solve this issue at the outset of discussions. Why invest all the time and calories into getting the deal to the one-yard line only to discover a deal breaker? It’s not only inefficient but also guaranteed to inflate your pipeline and kill your win rates.

So, as you map out your steps to close, anticipate the “nos”—who might have them and when might they crop up in the closing process? That way, you can “worry early” instead of fretting at the closing moments of a quarter.

If you need a closing map/closing schedule template, you can check out Maestro Group’s version here!