How to deal with skeptical customers

You just delivered the perfect pitch. The conference room is filled with smiling faces, all nodding along and eagerly discussing how your solution would solve so many of their problems—all, that is, except for Frank. We’ve talked about Frank before. He doesn’t do much, but he’s somehow got veto power on major purchases. And he clearly isn’t buying what you’re selling. 

Frank could be scowling for any number of reasons. Maybe he doesn’t see the merits of your solution. Maybe he doesn’t agree with your pricing. It could be that your service might present a challenge to his authority or disrupt an internal process that he personally helped develop. Heck, maybe he just doesn’t like your face. Whatever his problem may be, you’ve got to address it quickly before he derails your deal for good. 

So, how do you get buy-in from a clearly skeptical executive like Frank?

To find out, we spoke with Zack Duncan, an Emissary who’s currently president and principal digital consultant at Root and Branch and a former marketing executive at GNC and Dick’s Sporting Goods. Duncan’s been on both sides of the table, and he gave us key sales enablement pro insights on how to prepare for—and respond to—even the most skeptical stakeholders in a way that still gets them to sign on the dotted line.

Prospects are people, not titles

Titles can give you directional insight into who makes the buying decisions, but they’re far from foolproof. With six to 10 people involved in the average B2B purchase in 2023, the odds are good that the skeptic in the room may not be the one with the most senior title. In fact, they may not even be the decision-maker—but that doesn’t mean their opinion doesn’t count. The junior stakeholder at the table may wield unexpected influence over his VP. The director from another department could have had a poor experience with a similar solution, and she may be poised to poke holes in your pitch. To get ahead of this, Zack noted that it’s important to know each stakeholder’s priorities, influence, and personal preferences.

“Make sure to have an in-depth conversation about this with your internal advocate,” Zack said. “The person who’s making the meeting happen has a vested interest in your pitch going well. He or she should be able to provide a pre-read of the room, including personal quirks and past experiences.”

You should also know why they’re at the meeting in the first place—and what their reaction will likely be. More importantly, what role does each stakeholder see themselves having in your engagement?

Sales Enablement Pro Tips:

Subtle details about people like Frank can help you prepare a presentation that addresses their pain points quickly. As Zack noted, your point of contact might not offer this information, so it’s on you to ask questions like: Do they value customer testimonials? Do they need hard ROI figures or analytics to be convinced? These will help you understand how to speak their language and improve the chances of your pitch landing.

As another Emissary and former marketing executive at Cisco noted, it’s also a great idea to inquire about each stakeholder’s preferences when it comes to pitches themselves.

“Some people are visual learners, and some people are verbal,” she said. “You want to cover all the bases in advance because your audience’s preferences are likely mixed. Some people really want to see the slides, while others just want you to talk through it without making them see a huge deck.”

Get ahead of the objections

Now that you know Frank’s going to play hardball, it’s time to craft a plan to win him over. According to Zack, that starts well before the actual pitch. He recalled a former boss who declined every meeting invite unless it specifically spelled out why she personally needed to be there. He noted that this approach—earnestly telling people why you want their personal contributions—can give even the most skeptical stakeholders a sense of validation, which may go a long way to warming the room when it’s time to pitch.

Once you’re in the room, Zack stressed that giving Frank a platform to explain his objections can go a long way toward diffusing the situation. Prepare for strenuous objections and give him time to air them, but not so much time that he derails your meeting entirely.

Sales Enablement Pro Tips:

He suggested asking Frank some very specific questions, like:

• If this isn’t the right approach to solving your problem, what do you think the right approach is? Zack noted that this is a great way to both give Frank room to vent and be seen as an authority, as well as giving you the opportunity to align your solution with Frank’s preferred approach. Take note: if Frank doesn’t have a right approach in mind, move on quickly so he doesn’t feel embarrassed or put on the spot. Frank hates that.
• If you choose not to go with our solution, what will you do instead? If he brings up another vendor, ask for specifics about which features or functions he prefers. This can be a valuable way to inform the room about your own solution’s features and position your offering as equally, if not more, desirable.
• What do you think I missed or misinterpreted? This is a simple question that can unlock a lot of valuable insight into pain points and priorities. Zack also pointed out that it can give you the opportunity to gently correct misconceptions about your solution.

Work with your own sales enablement pro team to identify as many smart rebuttals as possible. If you get a request for information you don’t have, Zack said it’s best to simply say exactly that—then promptly follow up with the right answers after the presentation so no stone is left unturned.

Be empathetic

The real reason Frank’s resistant to your solution may have absolutely nothing to do with you or your pitch. In fact, you may never know the real reason—so it’s important to imbue your sales process with empathy from the start.

Zack recalled a particular naysayer at a former company: “The reason that he would object to any new technology was because he saw his role within the organization as being the go-to guy for anything new in the world of marketing and tech,” he said. When he was blindsided by a sales pitch for a new CRM, Zack pointed out that the stakeholder saw the new solution as a threat to his very job—so of course he was opposed. In that situation, he suggested the salesperson offer to connect one-on-one to get a better understanding of his concerns and show him that his role wasn’t threatened after all.

Winning over stakeholders like Frank will require you to be creative, understanding, and flexible. Get as much insight as you can ahead of time so you can prepare accordingly, and have a strategy in place to keep them from derailing your entire meeting. You won’t be able to win over every objector you encounter, but with the right prep and a solid plan, you can easily keep most of the Franks you encounter from turning a sure thing into a deal that’s DOA.

Executive Insights

All told, there’s no silver bullet to winning over a skeptical prospect, but our Emissaries gave us some actionable sales enablement pro tips for bringing them around. For some, it can be as easy as providing case studies ahead of time and showcasing ease of integration. For others, it may mean letting them be heard and giving them one-on-one attention. The most important thing is getting insight on the skeptics in advance and crafting a plan to help address their objections before they start.

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