You’re in another meeting that should have been resolved three meetings ago.
Finance is digging in their heels. Again. You can feel your jaw clenching as they bring up the same concerns you’ve already addressed. Don’t they get it? This initiative is critical. The data supports it. But here they are, blocking progress with their spreadsheet myopia.
Everyone’s talking. Nobody’s listening. And you’re starting to wonder if this organization is even capable of progress.
Here’s what you don’t see: Every single person in that room is thinking the exact same thing about you.
The Pattern You Can’t See When You’re In It
Let me tell you what’s actually happening in that meeting:
You walk in focused on YOUR objectives. You need this initiative approved. Your performance review depends on it. You’ve put weeks into this proposal.
Finance walks in focused on THEIR objectives. They have to report to the board next week. Margins are tight. The last “strategic initiative” went over budget. Their job security depends on those numbers looking good.
Sales walks in with THEIR pressures. Quotas to hit this quarter. Marketing support they need. Processes Operations keeps changing mid-quarter.
Everyone walks in convinced they’re right. And everyone walks in seeing the others as obstacles.
This is called being “in the box.” And when everyone’s in their box, collaboration becomes impossible—no matter how talented the team.
The Signs You’re In the Box
Here’s how you know you’ve gone into the box:
You’re building a case. Listing all the ways they’re wrong. Collecting evidence. Getting ready to “prove your point” instead of understand theirs.
You’ve stopped seeing them as people. That CFO isn’t a human being with real pressures and legitimate concerns. He’s “the guy who always blocks innovation.” He’s become a character in your story.
You feel righteous. Of course you’re right. The data supports you. Anyone reasonable would see this. If they can’t, that’s their problem.
You’re justifying your behavior. “I had to get aggressive—they weren’t listening.” “I had to go around them—they were being unreasonable.”
You blame them for the dysfunction. If they would just be more open-minded… If they would just think strategically… Then things would work.
Sound familiar?
What’s Really Happening
Here’s the thing about the box: When you’re in it, you genuinely can’t see that you’re in it.
From your perspective, you’re being reasonable and they’re being difficult. Your concerns are legitimate and theirs are political.
But from inside their box? They’re thinking the exact same thing about you.
The CFO isn’t thinking “I’m being an obstacle to progress.” He’s thinking: “I’m the only one here who understands fiduciary responsibility. I’m trying to protect this company from another expensive mistake.”
The VP of Operations isn’t thinking “I love blocking innovation.” She’s thinking: “I’m trying to maintain the systems that keep this company running. Every time we chase the new shiny thing, my team cleans up the mess.”
Everyone is convinced they’re the reasonable one. That’s the box.
Why Your Team Can’t Collaborate
You’re leading a cross-functional project. Everyone’s aligned on paper. Everyone wants it to succeed. Everyone’s talented and well-intentioned.
But somehow, it feels like herding cats.
Here’s what’s actually happening:
Finance sees a budget they’re responsible for, board members who will question every dollar, pressure to show ROI on everything.
Marketing sees brand reputation to protect, campaigns they’ve committed to, Sales making promises they have to deliver on.
Sales sees quotas to hit, customers who need solutions now, Marketing creating materials that don’t actually help close deals.
Operations sees processes that keep things functional, efficiency metrics, chaos that happens every time someone “innovates.”
Everyone walks into the room in their box. Finance sees your team as “unrealistic idealists.” Your team sees Finance as “bean counters who only care about money.” Nobody’s seeing each other as people with legitimate pressures.
What the Box Does to Sales Conversations
You have a quota. You need to close deals. So you walk into a meeting laser-focused on: “How do I get this person to buy?”
The moment that becomes your focus, you’ve gone into the box.
Now they’re not a person anymore. They’re a “prospect.” A “qualified lead.” An object you need to move from Point A (not buying) to Point B (buying).
You might think you’re hiding it. You’re asking questions. You’re nodding. You’re doing all the “active listening” things.
But they can feel it. On some level, their nervous system picks up that you’re not really interested in THEM. You’re interested in their signature.
So they go into their box too. Now they see YOU as an object—the “salesperson trying to get my money.” The “pitch I need to sit through.”
Now you’re trapped:
- You’re trying to “overcome objections”
- They’re putting up more resistance
- You’re having the same conversation on repeat
- They’re saying “I need to think about it”
- Nothing’s moving forward
You leave thinking: “They just weren’t ready to buy.”
They leave thinking: “Another pushy salesperson who doesn’t care about my problems.”
You’re both right.
What This Actually Costs You
Let me tell you what being in the box costs beyond deals you’re not closing and projects that aren’t moving:
You’re exhausted. Not from the work, but from constant pushing. The resistance. Feeling like you’re dragging people toward what’s obviously right.
You’re frustrated. Why can’t people just see reason? Why is everything so political? Why does it feel like you’re working against your own team?
You’re lonely. Even in rooms full of people, you’re fighting battles alone. Nobody really gets it.
You’re starting to doubt yourself. Maybe you’re not as good at this as you thought. Maybe you’re not cut out for leadership.
And underneath all of that: Something isn’t working. But you can’t quite see what.
Here’s what you can’t see from inside the box: You’re not the victim of difficult people. You’re participating in a system of mutual self-deception.
The Meeting That Changed Everything
I was consulting with a company on social impact integration. The VP was convinced the CFO was blocking everything. The CFO was convinced the VP was being financially naive.
They’d had the same fight in five different meetings.
I asked the VP: “What pressures is the CFO dealing with?”
She paused. “Well… he has to report to the board quarterly. They’ve been pushing him about margins. The last social impact initiative went over budget and he had to explain that. He’s probably scared that if this goes wrong, it’s his job.”
I asked the CFO: “What’s the VP actually trying to accomplish?”
He thought. “She’s seen poverty and climate change firsthand. She can’t unsee that. She’s probably frustrated because she sees long-term value but I’m focused on short-term numbers. She probably thinks I don’t care about impact.”
Just asking those questions started cracking open their boxes.
We restructured their next meeting. Instead of competing proposals, they came in with: “How can we build sustainable impact that ALSO meets our financial obligations?”
Different question. Different outcome. They created a phased approach addressing both concerns.
Because they stopped seeing each other as obstacles and started seeing each other as people.
The Cost You Don’t See Until It’s Too Late
Here’s what the box costs that doesn’t show up on any spreadsheet:
Your best people leave—not because of the work, but because they’re tired of the dysfunction.
Your projects fail—not because the strategy was wrong, but because nobody was actually collaborating.
Your sales pipeline stays stuck—because prospects can feel you’re trying to close them rather than help them.
Your innovation dies—because nobody feels safe sharing ideas that might be criticized.
You stay stuck in patterns that don’t work, having the same fights, running into the same walls, year after year.
The Question That Changes Everything
“How can I help things go right?”
Not: “How do I get what I want?” Not: “How do I convince them?”
But: “How can I help this whole situation go right—for everyone involved?”
When you genuinely ask that question, something shifts.
You stop seeing the CFO as the obstacle and start wondering: What’s he worried about? How can I help him look good to the board while moving this forward?
You stop seeing the prospect as the sale you need and start wondering: What problem are they actually trying to solve? What would make them a hero?
It’s a simple question. But it requires getting out of your box to ask it.
The Truth You Need to Hear
Right now, you’re probably in the box with someone.
You’re convinced they’re the problem. You can list all the ways they’re wrong, short-sighted, difficult, unreasonable.
And they’re doing the exact same thing about you.
The question isn’t whether you go into the box. You will. We all do.
The question is: How long are you going to stay there?
Because every day you spend in the box, you’re fighting battles that don’t need to be fought, missing opportunities to collaborate, and exhausting yourself pushing against resistance you’re partly creating.
You can keep being right. Or you can get out of the box and actually solve the problem.
But you can’t do both.
If you recognized yourself in this scenario, developing an outward mindset could transform your team dynamics, sales effectiveness, and leadership impact. Schedule a strategy session to explore how.
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