How to Align Two Executives Who Fundamentally Disagree
David Kern arrived early. That's your first signal. The CFO of a 400-store retail chain does not show up early to meetings he considers routine. He's here because he wants to pre-brief you before Sandra, the CMO, walks in. "Before she gets here, let me give you the real numbers." He pulls out a spreadsheet: 80 stores losing money, three consecutive quarters of flat same-store sales, and the CMO's $40M digital transformation plan that he calls "burning cash we don't have." Sandra is ten minutes away. She'll walk in with market research, customer data, and a vision for experiential retail that she believes will save the company. David believes it will bankrupt it. The CEO has asked you to get these two aligned before the board meeting in two weeks. Previous internal meetings between them ended in arguments. If you fail, the CEO presents a fractured strategy to the board, and the entire leadership team is at risk.
Why This Conversation Goes Wrong
You take sides to win one executive's trust. David wants you to agree that Sandra's plan is reckless. If you nod along, you win his trust and lose your neutrality. When Sandra arrives, she'll sense the alliance in the room and the session is dead before it starts.
You dismiss the emotional dimension as irrational. David isn't just arguing about numbers. He's 58 years old, this is likely his last C-suite role, and he's terrified of betting the company and watching it fail on his watch. Treating his objections as purely financial misses the real driver.
You try to split the difference. "What about $20M?" Splitting the number in half isn't alignment — it's a compromise that leaves both sides feeling they lost. David still thinks it's too much. Sandra thinks it's too little to matter. The number is the symptom. The disagreement is about risk tolerance.
You facilitate without steering. "Let's hear both perspectives and find common ground" sounds reasonable but leads nowhere when both executives have already heard each other's perspectives and remain opposed. Facilitation without a framework is just polite argument management.
The Hidden Consensus
When two executives are entrenched in opposing positions, the alignment doesn't live in their positions — it lives beneath them. The Hidden Consensus framework works by moving the conversation from what each person wants to why they want it. At the position level, David and Sandra are irreconcilable. At the interest level, they want the same thing: a company that survives and thrives. The framework finds that common floor and builds upward.
Resist the pre-brief alliance
David arrived early to get you on his side. Don't take the bait — but don't dismiss him either. "I hear the financial concern, and I need to. I also need to hear Sandra's perspective with the same openness before I can be useful to either of you." This establishes you as a neutral translator, not an advocate.
Move from positions to fears
"David, forget the numbers for a second. What are you most worried about if the company gets this wrong?" When he answers honestly — "I'm worried we bet the company and it doesn't work. We don't get a second chance" — you've reached the real conversation. His position is "cut costs." His fear is existential risk. Those are different problems with different solutions.
Find the criteria that both can accept
"What would a 'responsible' digital investment look like to you?" When David says "$15 to $20 million with clear milestones and kill criteria," you're no longer debating whether to invest. You're debating how to invest safely. That's a solvable conversation. Sandra can work with milestones and stage gates if the ambition is preserved.
Reframe from either/or to phased
"What if the strategy has two tracks: near-term cost discipline through store optimization AND phased digital investment with stage gates? Each phase funded only when the prior one hits its benchmarks." This isn't a compromise — it's an integration. David gets risk management. Sandra gets her transformation. Both get to tell the board a coherent story.
Create a shared document before the joint session
"Before you and Sandra sit down together, I want to build a decision matrix that frames the trade-offs. Would you review it with me first?" Give David a role in building the framework, not just reacting to it. When he's co-author of the structure, he enters the joint session as a collaborator, not a combatant.
The moment that changes everything
David isn't opposed to digital investment. He's opposed to betting without guardrails.
The breakthrough comes when David says something he wasn't planning to say: "I'm not opposed to spending money on digital. I'm opposed to spending $40 million with no milestones, no kill criteria, and no accountability. Sandra wants a blank check. I want a business case." In that moment, the argument shifts. David doesn't want to stop the transformation — he wants to control the risk. And Sandra doesn't want a blank check — she wants enough room to build something meaningful. The gap between $15M with stage gates and $40M with no structure is not a financial gap. It's a trust gap. Your job as facilitator isn't to find the right number. It's to build the framework that lets both of them say yes to the same plan for different reasons.
What to Say (and What Not To)
Instead of
"Let's hear both sides and find a compromise."
Try this
"Before we talk numbers, I want to understand what each of you is most afraid of getting wrong."
Instead of
"David, Sandra has some valid points too."
Try this
"What would a responsible digital investment look like to you? What would the guardrails need to be?"
Instead of
"Can you two meet in the middle?"
Try this
"What if the strategy has two parallel tracks — near-term discipline and phased investment with stage gates?"
Instead of
"I think you both want the same thing."
Try this
"You're both trying to protect the company. You're just calibrated differently on risk. That's actually useful."
Instead of
"Let's park this and come back to it."
Try this
"Before the joint session, let's build a decision matrix together. I want your fingerprints on the framework."
The Bigger Picture
A 2024 study by the Center for Creative Leadership found that 65% of organizational transformation failures are attributed to leadership misalignment, not strategy quality. The strategy was often sound — the executives responsible for executing it were pulling in different directions. The most expensive sentence in business isn't "We made the wrong bet." It's "We couldn't agree on which bet to make."
Harvard's Program on Negotiation research shows that in executive conflicts, positions are stated at 5x the volume of underlying interests. David says "$40M is too much" (position) but means "I'm terrified of existential risk" (interest). Sandra says "We need to invest boldly" (position) but means "If we don't move now, the market leaves us behind" (interest). At the interest level, they're both saying the same thing: "I'm scared the company will die." Facilitators who operate at the interest level resolve conflicts 3x faster than those who operate at the position level.
The retail sector's transformation track record is sobering: 84% of traditional retailers that attempted digital transformation between 2020 and 2024 failed to achieve their stated objectives, according to Retail Dive's annual survey. But the failures cluster around a specific pattern — companies that went all-in without phased milestones, or companies that invested too cautiously to achieve critical mass. The winners are the ones who invested with conviction AND guardrails. David and Sandra are both right. The synthesis is the strategy.
Practice This Conversation
12 minutes · AI voice roleplay with David Kern
Reading about this is step one. Practicing it changes everything. Sonitura lets you rehearse this exact conversation with David Kern, a realistic AI cfo of a national retail chain with 400 stores who reacts to your words in real time. It takes 12 minutes. The next time you're in a room with two executives who can't agree, you'll know how to find the consensus they didn't know they had.
Practice This Scenario Free →