Episode #470 – Lisa Earle McLeod

We’re joined once again by Lisa Earle McLeod, renowned author of “Selling with Noble Purpose” and a global leader in purpose-driven business strategies. This time, Lisa dives deep into the transformative role that artificial intelligence is playing in negotiation strategy and tactics. We discuss how AI is changing the sales game—not just by giving us better tactics, but by helping us see through our customers’ eyes to uncover what truly matters to them.

Lisa shares fresh insights on crafting more effective negotiation approaches by leveraging AI to understand customer risks, uncover hidden pain points, and create compelling questions that drive value-based conversations.

Plus, she unpacks the do’s and don’ts of using AI, highlights common pitfalls, and shares a real-world story of closing a challenging deal using these cutting-edge methods. This episode is packed with practical advice on how to harness AI for more genuine, successful negotiations—while keeping the client at the heart of it all.

Outline of This Episode

• [00:00] AI missteps in sales negotiation.
• [06:00] Customer-centric discovery emphasizes ROI by highlighting competitive consequences.
• [08:46] AI improves business strategy by generating unexpected, insightful questions.
• [11:52] Use AI as a nonjudgmental coach available anytime for negotiation advice.
• [15:11] AI communication dos and don’ts.
• [18:28] Lisa’s story of using AI to highlight the cost of inaction.

Rethinking How We Use AI in Sales Negotiation

AI tools have flooded the sales landscape, promising quick wins and smarter decisions. But, as Lisa warns, the way most sellers use AI can actually backfire. Too many reps default to self-serving prompts—focused on expressing their own value or outshining the competition—instead of truly stepping into their client’s shoes.

Instead, Lisa suggests using AI to uncover the risks, concerns, and goals that matter most to your buyer. For example, rather than asking, “How can I win this deal?” prompt AI with, “What risks does my client face if they don’t act on my proposal?” or “What might the CFO of a large manufacturing company be worried about right now?” By doing this, AI becomes a discovery partner—not just a generator of clever closing lines.

The Power of “Cost of Inaction” in Persuasion

Too often, sellers build polished ROI arguments, only to watch stakeholders do nothing. Why? Highlighting what a company could lose by standing still is often far more compelling than dangling the prospect of what they might gain.

AI can be a powerful ally in quantifying and articulating these hidden risks. By prompting AI to brainstorm implication questions—“What happens if your competitors outpace you next year?”—sellers can stimulate genuine urgency within decision-makers. It’s not about scare tactics; it’s about helping clients confront realities they may have overlooked, with the help of AI’s outside-the-box perspective.

Best Practices: Do’s and Don’ts for AI-Driven Negotiation

Harnessing AI’s power in negotiation requires more than clever prompts; it demands ethical considerations and a client-centric mindset. Lisa shares these essential ground rules:

Do:

• Start with the Client: Frame AI prompts around your buyer’s role, goals, and pains—not your own pitch.
• Unearth Strategic Goals: Have AI help uncover what truly matters to your client’s business, even if it’s unrelated to your product.
• Ask for Better Questions: Use AI to generate implication and discovery questions that go beyond the obvious, elevating sales conversations.

Don’t:

• Don’t Overshare: Never input confidential or proprietary information into public AI tools—treat them as you would social media.
• Don’t Be Self-Serving: Avoid focusing AI on “how to win” at the expense of the client’s needs—this erodes trust and effectiveness.
• Don’t Sound Like a Robot: Use AI’s polished language carefully. While it’s great for proposals, it can sound canned in conversation. Personalize and adapt its suggestions.

Transparency is also key. If you use AI to prepare, be open about it: “I put your profile into AI to think more deeply about your goals—here’s what came up. How does that resonate with you?” Such honesty builds authentic rapport.

Flipping the Script and Winning Deals

To prove the methodology, Lisa shares her own recent experience: her firm faced a client paralyzed by indecision—the status quo seemed easier than change. By using AI to map out the tangible and long-term risks of doing nothing, and then presenting these “costs of inaction” back to the client, the conversation shifted. The client moved from hesitant to decisive, signing a high-value contract immediately. The lesson? When sales teams use AI to spotlight what’s at stake for the buyer, outcomes transform.

Sales negotiation isn’t just about tactics—it’s about deep discovery, empathy, and helping clients make the best decisions. AI, when harnessed thoughtfully, amplifies a seller’s consultative skills.

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1. What was a pivotal moment in your career that shaped your approach to negotiation, and how did it influence your strategy and tactics?

In my twenties my boss said “Everything in life and I mean everything from your spouse, to your job, to your kids, is a negotiation.”   I thought I would hate to be married to you. I realize,  there is a time to negotiate, but if you approach every single interaction that way, you will wind up with a very transactional life. 

2. Can you share a specific negotiation tactic that has consistently helped you close deals more effectively? Please provide an example where it worked.

When negotiating, I always make a practice to ask what outcome they’re hoping for. I make a list of everything they want, I ask them why those things matter to them. This makes them feel heard and they relax. They often wind up taking things off the list themselves. People thinking asking them what they want is a weak more. It’s not, it’s the ultimate power move. You’re guiding the conversation, and you are becoming the person helping them instead of lording over them.

3. What is the most challenging negotiation you’ve ever faced, and what strategy or tactic helped you turn it into a win? 

Many times, our contracts are turned over the purchasing, who only care about the bottom line price. Before I meet with purchasing, I I ask our buyer, who cares about the impact of our solution, to send an email describing why they bought, and saying – I want them to put their top people on our project, so don’t hard ball them on price and force them to put less resources on our job.

Often purchasing is oblivious that when they whittle the price down, you are substituting in cheaper people and tools. 

4. What are your top three must-have tools, frameworks, or resources that sales professionals should use to improve their negotiation skills? Must have tools 

– Lookup how your buyer gets evaluated by their org 

– Be clear about the positive impact of your solution before you start negotiating

– Make sure your buyer has bought into the impact – don’t just repeat, ASK them, what positive impact will this have on your organization, if we implement successfully. 

– Start your negotiation saying, let’s figure out how we can have the most impact on your and your org possible. 

5. With buyer behaviors evolving and AI playing a larger role in sales, how do you see negotiation strategies and tactics changing in the future? 

What should sales professionals do to stay ahead? USE AI TO KNOW YOUR CUSTOMER BETTER!!   If you’re calling on an organization of any size, you should know their business objectives  their biggest challenges, what success looks like for them beyond your product. 

6. What’s are some simple but powerful negotiation tactics that most salespeople overlook?

Prove your value and don’t negotiate. Just because they ask you to negotiate doesn’t mean you have to do it. My firm charges top tier fees. When someone asks us to negotiate, we say, We spend our time increasing the net positive impact for you.  We don’t spend our time whittling down our price.