How to Use Questions to Challenge Assumptions in Negotiation

Here's a discovery question that helped me sell my first 7-figure Enterprise deal as an AE. Prospect was looking for negotiation training. The company I was working for didn't sell negotiation training. Instead of trying to convince her negotiation wasn't the right answer, I sought to understand why they were looking to solve for negotiation. I asked, "How did the leadership team arrive at negotiation as the right problem to fix?" Her: "Because we sell a commoditized product. Customers don't see a difference between our parts and our competitors'. We keep losing to low-cost competition. Every deal is turning into a price war." Me: "This may be an awkward question, but, is there actually a difference?" Her: "When it comes to our ability to outperform on reducing plant downtime - yes." Me: "And, how often are customers factoring the cost of excess downtime into their decision?" Her: "Not enough. They're usually just looking for the cheapest replacement part." Me: "Does the negotiation phase feel like the right time to raise that?" Her: "No - it's too late in the sales cycle." Boom. That was the magic moment. That was the moment SHE introduced doubt that negotiation was the right problem to solve. It became her a-ha moment. Her realization. Her idea. It opened the door for me to share a different POV on an alternative root cause of the known problem. That led to a meeting with the ELT to discuss root causes, not solutions. TLDR: People hate to be told they are wrong. Help them revisit their own beliefs/assumptions by seeking to understand HOW they arrived at a conclusion. There's a lot of insight to be gained by asking, "How did the team arrive at X as the right problem to solve?".

Your challenger training may have taught your reps to start fights they can't finish. You spent $50K on a sales methodology. Flew in consultants. Ran workshops on "constructive confrontation." Then your AE challenges a buyer's assumption and gets hit with: "Actually, we've been doing this for 15 years and know our business better than you do." What happens next? They fold. Apologize. Start pitching features. Because you taught them to throw punches, not take them. The big thing about challenger selling is that it only works if your reps can handle the emotional backlash that comes with disagreeing with prospects. And many of them can't. Which, to be clear, isn't necessarily their fault. They just haven't been provided any psychological resilience training. Before you teach reps to challenge assumptions, teach them to: 1. Expect emotional resistance as validation rather than rejection. When a buyer gets defensive, that means you hit something real. Most reps interpret pushback as "I said something wrong" instead of "I said something that matters." Train them to lean in: "It sounds like this is something you've put a lot of thought into. Walk me through your current approach." 2. Master the "third question" technique. Most reps ask one question, get pushback, then retreat. Encourage your reps to have the confidence to dig deeper. - First push: "That's an interesting perspective. What's driving that approach?" - Second push: "And how long have you been using this process?" - Third push: "What metrics are you tracking to measure success?" Each question shows you're genuinely curious, not just challenging to challenge. 3. Practice the uncomfortable pause. When buyers push back hard, it's natural to try and fill silence with backpedaling. Just let the tension breathe, people! Count to three. Then ask: "What's working well about your current approach?" 4. Reframe resistance as qualification data. Every objection tells you something about their pain tolerance, decision-making process, or internal politics. If they can't handle being challenged in discovery, they DEFINITELY can't handle change management post-sale. To be clear, challenger selling works. It just works better when your reps can handle the emotional backlash that comes with disagreeing with prospects. Don't let your reps crumble at the first sign of friction. Train the psychology first. The methodology second. In a world where every rep has the same playbook, resilience is the real differentiator.

On this episode of "How Sales Managers can run more effective Pipeline Reviews"...we're back with the next step of the framework I used to help HubSpot scale from 40 >> 400 sales managers from 2018-2022. Step 2: 𝗵𝗼𝘄 𝘁𝗼 𝗽𝘂𝘀𝗵 𝘆𝗼𝘂𝗿 𝗿𝗲𝗽𝘀 𝘁𝗼 𝗯𝗲 𝗰𝗿𝘆𝘀𝘁𝗮𝗹 𝗰𝗹𝗲𝗮𝗿 𝗼𝗻 𝘄𝗵𝗮𝘁 𝗶𝘀 𝗿𝗲𝗮𝗹𝗹𝘆 𝗵𝗮𝗽𝗽𝗲𝗻𝗶𝗻𝗴 𝘄𝗶𝘁𝗵𝗶𝗻 𝗱𝗲𝗮𝗹𝘀 𝘁𝗼 𝗱𝗲𝗰𝗶𝗱𝗲 𝗶𝗳 𝗶𝘁'𝘀 𝗿𝗲𝗮𝗹 𝗼𝗿 𝗻𝗼𝘁. First of all...No one should make assumptions; not reps or sales managers.  When people assume, they lose.  Objective facts are what matters.  Your job as a sales manager is to help remove assumptions.  You need to help your rep think through and remove assumptions from each deal, so you Sales Manager can fully understand what’s going on and give yourself the best opportunity to ‘call the right play’ with your rep. (See my recent posts for what 'calling the right play' actually means.) Just like we teach our reps to ask their prospects second and third layer questions to dig deeper during discovery calls, you need to do the same during pipeline reviews.  Why are you digging deeply?  You're trying to find the objective facts that are needed in order to sell something. What do second and third layer questions that I like to ask sound like? I'm so glad you asked! - “How did you come to that conclusion?” - “What evidence do you have?”  - “Can you remember their specific answer, the exact phrase they said?” - “What else did you consider before deciding on that as a next step?” - “Why do/did you feel like that’s the best path forward?” ^^ Asking these next layer questions should help you get a more accurate understanding of your reps' initial responses to questions like: - "If they don't buy, why would that be?" - "Why should this prospect change anything?" - "Why are they thinking about a purchase decision now?" - "Why are we on their short list?" - "What's going to get in the way of closing this?" Example: - You: "Why should this company make a change from the status quo?" - Rep: "Because they told me they need to do A and B, and C just happened" Many managers stop here ^^ they take this answer at face value and move on. Don't do this. Keep going: - You: "Sounds like a couple solid use cases, promising. How did they come to the conclusion that they have to change from the status quo to solve this?" - Rep: "They told me XYZ." You: "And what about you, what do you think...do you agree?" Awkward pause. Your rep will likely stare at you because they believe this should be overly obvious. Rep: [will start to justify/sell you on their opinion and assumptions will surface] You: - Pressure test - Decide if the deal is real - Help your rep understand why you think what you think - Confirm you have their buy-in that they agree with what you think - CALL THE RIGHT PLAY (Step 3) If you don't take the time to figure out if a deal is real, then it's pointless to talk about "next steps". End scene.