I need to tell you about a relationship I completely botched. Not like it was “ok” and I am just being hard on myself. I mean a stakeholder relationship that truly did not work.

Not a personal relationship: a stakeholder relationship. One that should have been collaborative and energizing but instead became something I actively dreaded. The kind where you see their name on your calendar and feel a weight in your chest that sits there all morning.

I'm sharing this not because I've solved it (I haven't, not fully), but because I suspect I'm not alone in this experience. And because the patterns I've recognized might help you avoid the same trap.

It started subtly. A few meetings where the energy felt off. Suggestions that landed flat. Proposals that were met with "but have you considered..." followed by a litany of reasons why the approach wouldn't work.

At first, I adjusted. Different angles. More data. Better framing.

But the pattern persisted:

present idea → get pushback → revise → present again → get different pushback.

What I didn't recognize at the time was that we were building a negative reinforcement loop. Each conversation reinforced the same dynamic:

No positive reinforcement. No "yes, and..." No building on ideas together. Just a steady drip of "not quite right" that accumulated into something much heavier.

Within a few months, I was experiencing something I can only describe as existential dread before our meetings. Not anxiety about specific outcomes, but a deeper feeling that I fundamentally didn't know how to navigate this relationship successfully.

It took me too long to realize what was actually happening: we were misaligned on altitude and had no shared agreement about what we were even there to discuss.

They wanted final strategy with no collaboration.
They would come with strategic direction, fully baked. No workshopping. No thinking out loud. Just "here's the plan" with no room for me to ask questions. They weren't interested in co-creating strategy—they just wanted to present the finished thinking.

Ok so if they had all answers I guess we needed to talk about the details. The “how” will we make this work.

But as you might have expected…they also rejected tactical discussions.
When I pivoted to tactical execution ("here's how we're implementing the strategy we aligned on"), they viewed it as beneath the conversation. Too in the weeds. Not strategic enough and definitely meant for “other people” to have but not us.

So I was stuck in a bizarre middle ground: can’t talk about the high-level vision and no room to talk about the tactical problems and opportunities.

And let’s be clear: I took it extremely personally. I thought it was my problem to fix soley. That I was being a bad partner. Taking it too personally also didn’t help the cycle we were in.

However, the problem wasn't my altitude. It was that we had no shared understanding of what altitude we were supposed to be operating at together.

But the story doesn’t end here. It got even worse.

Since we had no shared altitude we fell into what I call: the ownership mentality.

I own this function. My name is on the work. I'm accountable for the outcomes.

That sense of ownership is usually an asset—it drives quality, urgency, and accountability. But in this relationship, ownership became a trap.

Because I felt so much ownership, every piece of feedback felt like a referendum on my competence. Every pushback felt like evidence that I wasn't delivering what they needed. And the more I tried to prove I had everything under control, the more I reinforced a dynamic where they just evaluated rather than collaborated.

On their side, they likely felt ownership of the strategic direction in a way that made them protective rather than generative. When someone says "I own this," they're signaling "don't just approve my plan—own the outcome with me." But when the other person also feels ownership, they respond with "I need to ensure this is right" rather than "let's build this together."

Both parties owning the same thing doesn't always create shared accountability. Sometimes it creates competing control.

1. Negative reinforcement loops…well they suck

Once established, they're self-perpetuating. Each negative interaction makes you more defensive or more elaborate in the next one, which often just gives more surface area for criticism. You start bringing solutions that are so comprehensive they can't be picked apart but they also can't be collaborated on because they're already fully formed.

The fix isn't more preparation. It's breaking the pattern entirely. Sometimes that means explicitly naming it: "I notice we keep getting stuck in this dynamic. Can we try a different approach?"

2. Altitude misalignment is a hidden killer

You can be great at strategy and great at execution and still fail if you don't have explicit agreement on where you're meeting. The most useful question I didn't ask enough: "For this conversation, what level are you hoping we operate at?"

These are different conversations. Treating them as interchangeable creates the feeling that everything is wrong when really, you're just having the wrong conversation.

3. Existential dread is a diagnostic tool

When you feel that weight before a stakeholder meeting—not nervous about a specific outcome, but fundamentally unsure of how to succeed—you're likely dealing with one of two things:

Both are fixable, but only if you name them explicitly.

4. Ownership without collaboration is lonely

Feeling like you own something is motivating. Feeling like you own something alone is exhausting. The "name on the page" mentality should drive quality, not isolation.

And in reverse if you sense you own something together with another stakeholder and they believe they own on it independently creates a toxic environment. Trust me no one should be arguing about how owns a Google Document in 2025.

If you find yourself constantly defending your work rather than co-creating it, something about the ownership dynamic is off. Maybe you're holding ownership so tightly that others can only react, not contribute. Maybe they're holding it so tightly that you can only execute, not influence.

Either way, ownership becomes a burden instead of a motivator.

I'm still working through this. These types of relationships aren’t magically fixed. But here are the small shifts that are helping:

Naming the altitude explicitly
Before meetings, send a one-line frame: "This conversation is for [workshopping approach / aligning on principles / reviewing execution / course-correcting]." It sounds painfully obvious, but it removes ambiguity.

Asking for co-creation explicitly
Instead of bringing finished plans, bring frameworks with intentional gaps. "Here's the structure I'm thinking. Where would you push on this?" It's vulnerable because the gaps are visible, but it invites collaboration instead of evaluation.

Seeking small wins to break the cycle
Look for low-stakes opportunities to get a "yes" or a "yes, and..." Something that builds a single data point of positive reinforcement to start shifting the pattern.

Reframing ownership
Shift from "I own this outcome" to "we're co-accountable for this outcome, and here's how I'm thinking about my part." It's semantic, but it changes the energy from defensive to partnership.

The hardest part of this reflection is acknowledging my role in it. It's easy to say "the stakeholder was difficult" or "we just didn't click." But the reality is I contributed to this dynamic at every turn.

I let negative patterns establish without interrupting them. I brought increasingly polished work when what was needed was messier collaboration. I never asked directly: "What do you actually need from me in this relationship?"

Stakeholder relationships go wrong for lots of reasons. Sometimes it's genuine misalignment of values or vision. Sometimes it's politics or personalities. But often, it's a series of small misalignments that compound into something that feels insurmountable.

The good news? Small misalignments can be corrected. You just have to be willing to name them.

If you're struggling with a stakeholder relationship right now, ask yourself:

You might find, like I did, that the relationship isn't fundamentally broken it's just operating on mismatched assumptions that were never made explicit.

Currently, I am the Managing Partner and COO at AlignedCX, where I help companies build scalable customer education programs and academies. Previously spent over a decade scaling HubSpot Academy globally. Want to connect with me to learn more about how I can help your organize? Reach out to me on LinkedIn.

Learning by Design as a newsletter written by Courtney Sembler a customer education and customer experience executive. It focuses on customer education that drives retention, adoption, and revenue—by design, not by accident.

The newsletter is not just about learning and customer education. Courtney explores topics about leadership, reflection, and overall how to be a good human leader into todays AI-focused world.