Back to Basics – Week 7: Are you running a three-legged race?

Want to know the superpower of every great salesperson?

It’s not a fancy closing technique or a killer slide deck.

It’s one simple phrase: “What might get in the way?”

This question is pure gold because it uncovers the stuff that kills deals — the internal politics, budget constraints, competing priorities, and decision-making drama that your prospect might not volunteer on their own.

Here’s why this matters more than ever:

In today’s market, contracts aren’t won or lost on your ability to do the job (you’re already brilliant at that). They’re won or lost on your ability to help your champion navigate the obstacles between “yes, we want this” and “here’s the signed contract.”

The secret to getting really good at B2B sales? Your job is far less about convincing your champion you’ve got what it takes to help them, and much more about supporting them to get internal buy-in and jump through all the hoops it’s going to take to get to contract.

During your sales conversations, try asking:

“I’m curious; is there anything that might get in the way of us working together on this?”

When you ask this question, you’ll uncover things like:

• “Well, our CFO is pretty conservative about new spending right now”
• “The last consultant we hired didn’t go well, so there might be some skepticism”
• “We’re in the middle of a re-org, so timing could be tricky”
• “I’d need to get buy-in from two other department heads”

Now you’re cooking with gas. Instead of sending a proposal into the void and hoping for the best, you can address these concerns head-on and help your champion build the internal case for working with you.

This is how you shift from running a relay race to running a three-legged race with your prospect.

In a relay race, you pass the baton (your proposal) and hope they can carry it across the finish line alone.

In a three-legged race, you’re tethered together, working as a team to overcome obstacles and reach the goal together.

Your homework: Ahead of sending your next proposal, be sure to ask, “What might get in the way?” Then actually listen and dig deeper. 

If your prospect reveals potential issues, ask follow-up questions to explore how you might support them in getting the support they need:

• “What would your CFO need to see to understand the ROI of this investment?”
• “What do you think it would take to overcome any skepticism that exists in the wake of your former consultant?”
• “Let’s talk about your re-org so we can be sure my proposal is well-timed and adding value — not stress.”
• “Tell me more about these department heads — what do they care about?”

Remember: Those obstacles they mention aren’t roadblocks — they’re your roadmap for closing the deal.

P.S. If you’re thinking, “Cool, Allison, I’ll do this going forward — but how do I handle deals that have gone cold?!” Don’t worry, I’ve got you. Check out this blog post where I share an email script to re-engage prospects who have ghosted you! 👻