Negotiating With Your Boss
Especially one with an ego
So your CEO just rewrote your carefully crafted plan…with ChatGPT.
If you’re a CTO, that sentence might sting because it’s not hypothetical. A friend of mine who coaches technology leaders told me about a situation where a CTO presented a detailed organizational strategy to their CEO. Hours of thought went into it. The CEO’s response? “I don’t think this is a good plan.” Then, as if to add insult to injury, the CEO fired back an alternative strategy that was clearly a copy-and-paste job from ChatGPT.
If you’ve ever been in this situation, maybe not AI specifically, but some form of “the boss rewrote my work”, you know the cocktail of emotions:
My CEO doesn’t trust me.
My CEO is doing my job.
Why am I even here if they can just replace me with a chatbot?
All understandable reactions. None of them are useful.
The real question is: how do you navigate this kind of moment without blowing up the relationship, or your own credibility?
Note: I’m writing this as a conflict between the CTO and CEO but substitute any managerial relationship here, e.g. IC <-> line manager, manager <-> director, Marketing VP <-> CMO, CEO <-> BOD, etc.
One of the hardest parts of being a senior leader isn’t the technical challenges. It’s the human ones, especially when it comes to working with someone above you in the org chart.
In theory, the CEO should stay at the strategic, big-picture level, and the CTO should handle the details of how technology supports that vision. In reality, boundaries blur. Some CEOs stay hands-off. Others dive headfirst into the weeds. And when they do, it can feel like encroachment.
Steve Jobs was famous for his ego and his brutal feedback. But what’s less remembered is how much he did incorporate feedback, sometimes after initially rejecting it. For instance, early iPhone prototypes had no App Store. Jobs dismissed the idea of third-party apps. After persistent advocacy from his team, he reversed course. That decision arguably became the cornerstone of the iPhone’s dominance.
Jobs didn’t always admit he was wrong. But he often quietly folded others’ ideas into his vision. Working for someone like that requires resilience. You can’t simply “win” by proving them wrong, even if your reasoning is airtight. The power dynamics don’t work that way.
In the ChatGPT plan example, the CTO had a few obvious options:
Re-argue for the original plan, hoping logic would prevail.
Pick apart the CEO’s cut-and-paste strategy and highlight its flaws.
Do a side-by-side comparison, showing why their plan was superior.
On paper, all these approaches make sense. In practice, they backfire. Why? Because they all amount to telling your boss: “You’re wrong, and I’m right.”
Even if you are right, the conversation turns adversarial. And once it’s framed as a battle of egos, you’ve lost. Here’s the move I recommend instead: find aspects of your boss’s plan to incorporate into your own.
This doesn’t mean capitulating. It means reframing the work as a collaboration. By weaving in some of their ideas, even if they’re not great, you demonstrate that you listened, valued their input, and can adapt.
In the strategic plan example, the CTO could have:
Taken the CEO’s ChatGPT-generated framework as a “strawman” and refined it.
Highlighted a few specific elements worth keeping (“I like the emphasis on X and Y; let’s merge those into the existing plan”).
Presented a revised version that felt like a fusion rather than a rejection.
This way, the CEO sees their fingerprints on the plan. Their ego is intact. And the CTO still gets to guide the strategy with their expertise. It’s less about conceding technical ground and more about managing perception. You’re negotiating, not litigating. A phrase that I like is “Yes, and…”
This approach works for a few reasons:
It shows respect. Even if the CEO’s plan is half-baked, acknowledging the good parts of it signals that their voice matters.
It diffuses defensiveness. Instead of setting up a confrontation (“your plan vs. mine”), you frame the conversation as, “how do we get to the best plan together?”
It preserves influence. If you go to war and lose, your ability to shape future conversations diminishes. If you collaborate, you maintain trust and a seat at the table.
It buys you flexibility. By choosing which pieces to integrate and which to let slide, you protect the most important parts of your work while letting go of non-essentials.
In other words, it’s not about being right. It’s about being effective. This principle of incorporating feedback, even when it feels wrong, reminds me of how Pixar approaches storytelling.
Pixar is legendary for its “Braintrust” meetings. Directors present storyboards or early cuts of films, and a roomful of peers, often including Ed Catmull, John Lasseter, or Pete Docter, tear them apart. The feedback is brutal, sometimes contradictory, and occasionally flat-out unhelpful.
The magic is in how directors respond. They don’t treat feedback as commandments, but as signals. They look for patterns, extract useful nuggets, and fold those into the next version. The result isn’t anyone’s singular vision, it’s a collective refinement. That’s why Pixar films rarely flop.
The key takeaway: treat every plan, proposal, or document as a work in progress. The less tightly you cling to “ownership,” the easier it is to absorb criticism without losing momentum.
When my friend coaches technology leaders, he will often ask: Do you want to be right, or do you want to be effective?
Being right feels good in the moment. Effectiveness builds trust and influence over the long run.
Here’s how to shift the mindset:
See feedback as raw material. Even if it’s clumsy, irrelevant, or ego-driven, you can usually extract something useful.
Detach identity from output. Your worth as a leader isn’t tied to any single document or plan.
Play the long game. One concession today can buy you more autonomy tomorrow.
Reframe the goal. The end game isn’t to “win” against your boss. It’s to advance the organization’s goals together.
Let’s revisit that CTO and their ChatGPT-wielding CEO.
If the CTO had gone into defensive mode, the outcome would have been predictable: friction, erosion of trust, and a frustrated CEO who felt ignored. Instead, by folding in some of the CEO’s ideas, even if superficial, the CTO could reframe the entire exchange:
The CEO feels heard.
The CTO preserves the essence of their strategy.
The company moves forward with a unified plan, rather than a tug-of-war.
Negotiating with your boss, especially one with an oversized ego, requires restraint, empathy, and strategic thinking. The instinct to defend your work is natural. But often, the smarter move is to absorb, adapt, and evolve.
Remember:
Don’t litigate. Incorporate.
Don’t cling. Iterate.
Don’t aim to be right. Aim to be effective.
Every plan you write is just a draft. Every conversation with your boss is a negotiation. And the leaders who thrive are the ones who can set aside ego, not just their boss’s, but their own.
Very insightful and practical. Thank you!