Today’s episode is for you if you’ve ever put your hopes into one conversation with your manager, thinking this is the talk that’s finally going to solve the issue that;s been bothering you, or get you clarity you next career step. Only to walk away feeling like nothing actually shifted. If any of that sounds familiar, you’re going to discover why we pin everything on one conversation, what’s really happening when these talks don’t deliver the clarity we’re desperate for, and the approach that actually gets you what you need—without so much of the frustration or second-guessing yourself.

This has happened to me countless times over my career, and I wanted to do an episode on it, because it’s a phenomenon we see again and again inside our program Speak Like a Senior Leader too where we work with accomplished mid level leaders who feel like their expertise isn’t matching how they come across. And when this pattern of disappointment keeps repeating—when you keep having conversations that feel like they should matter but don’t seem to change anything—you start to doubt yourself. You wonder if you’re just not cut out for these high-pressure moments. If you don’t know how to communicate in a convincing way or get your point across… and maybe you never will! If maybe you don’t have what it takes to hold your own with senior leaders or influence the people who control your opportunities.

But we see it ALL THE TIME. Once we explain and unpack what’s really happening here—it’s like a lightbulb goes off. And it’s often one small unlock that can totally transform how you show up with leaders across the board and up your chain of command. And speaking of which, make sure you have grabbed your spot for my upcoming FREE training, Earn Up to $200k more in 2026: 5 Steps to Speak Like a Senior Leader. Just go to melodywilding.com/training or the link in the show notes. I’ll be giving you 5 small tweaks you can make TODAY to articulate yourself with more polish and precision. 

So here’s what usually plays out: you have something important you need to bring up with your boss. Maybe it’s about your workload—you’re drowning and need to push back on taking on another project. Maybe it’s about decision-making—you keep getting left out of things that should be within your scope. Or maybe it’s simpler than that—you just need your boss to stop CC’ing you on every single email they send because it’s unnecessary. 

Whatever it is, there’s usually a whole journey that happens before you ever say anything out loud. Typically 3 phases: 

Phase one: Should I even bring this up?

You bat the idea around in your head for days, maybe weeks. You notice the problem. You think about mentioning it. Then you talk yourself out of it. Maybe it’s no big deal. Maybe it’ll go away on its own or was a one time thing. Maybe it won’t matter after a certain deadline passes. Maybe I’m overreacting. But it keeps nagging at you. It comes up again. You reconsider. Finally, you make the decision: OKAY, I’m going to say something.

Phase two: When should I bring this up?

Now you’ve spent all that energy deciding TO say something, and you have to devote even more energy figuring out WHEN to say it. Do I bring this up in our regular one-on-one? Or should I schedule a separate meeting? If I wait until our next check-in, that’s two weeks away—is that too long? But if I ping them now asking for time, will they think something’s seriously wrong? You go back and forth, but you finally land on a plan. Great. 

Now onto Phase three: How do I actually say this?

This is where things really ramp up. You start plotting exactly HOW to frame it. You turn over different talking points in your head. What’s the best opening? Should I lead with the problem or maybe my request? Should I be more direct or ease into it? You rehearse versions of this conversation in the shower. You type out drafts in your notes app. Maybe you even practice with ChatGPT, asking it to play your boss.

The day before, maybe you’re thinking about it so much it’s a distraction from the rest of your work. You’re visualizing yourself delivering the words. You can picture the room, the moment, how you’ll sit, how you’ll start.

What I want you to pay attention to here is how ALL of this mental and emotional prework has happened before you even utter a single word.

Then the moment of truth comes. It’s go time. You walk into your one-on-one or grab your boss for a quick chat. You say your piece—maybe a little more nervously than you hoped, but you get through it. 

And sometimes—not that often, but sometimes—you DO get the resolution you were hoping for. Your boss says, “Wow, I’m so glad you brought this up. Let’s figure this out right now.” They’re engaged. They ask good questions. They make a decision on the spot or commit to a clear next step with a specific timeline. Everything gets tied up in a nice bow in that one conversation. You walk out feeling lighter, validated, like the mental and emotional energy you invested actually paid off.

Those moments? They’re great. They reinforce the belief that if you just prepare enough, say it the right way, pick the perfect time—the conversation will deliver.

But most of the time? That’s not what happens.

Most of the time, your boss responds… fine. They nod. They acknowledge what you said. Maybe they ask a clarifying question or two. They say something like “Let me think about that” or “Good to know, let’s circle back” or “I hear you, let’s see what we can do.”

Or maybe you get some resistance. Not hostile, just… hesitant, maybe a bit dismissive. “I don’t know, this isn’t something I can think about today” or “We’re in a really tight spot right now, so I’m not sure how realistic that is” or “Let me see what I can do, but I can’t promise anything.”

And then… the conversation just kind of ends. It gets punted. No clear resolution. No decision made. No timeline. So the meeting ends and you walk away feeling… crumby. Deflated and definitely frustrated.

What’s confusing is: objectively speaking, the conversation wasn’t a complete disaster.  If you had to rate it, you’d probably say it was on the lower end of neutral.  If it was, then your disappointment might feel more justified or at the very least you could pinpoint where it’s coming from.

You feel so bad because it feels incomplete. Like you brought up a problem but there’s no ending. Just loose ends. An open loop that you’re not sure how or when will close. 

And what’s worse, in your head, you weren’t preparing for neutral. You were preparing for a turning point. You built this conversation up as a moment – the moment – things would shift—and instead, it just… happened, yet there was no immediate relief or resolution. It feels unsatisfying because nothing got fixed. 

Let me tell you what I call this, because I’ve seen the same thing play out so many times in my coaching career that I had to give it a name.

I call it “conversational perfectionism.” It’s this phenomenon where we fixate on one conversation like it’s going to solve everything. We pin all our hopes, all our expectations, all the relief we’re craving onto this single interaction with our boss.

Now, consciously, you probably wouldn’t say “I think this one conversation is going to fix all my problems” or “This talk will definitely get me promoted.” That sounds unrealistic when you say it out loud and you LOGICALLY know better than that. 

But look at your behavior. Look at all those phases we just walked through—the deliberation, the mental rehearsals, the emotional buildup. That’s how we prepare for something we believe is make-or-break, not how we prepare for something we think is just one small step in a longer process.

We’re treating this conversation like it’s the conversation. The one that will finally give us clarity. The one that will establish a new normal. The one that will resolve the tension we’ve been sitting with for weeks or months.

Part of it is how we talk about difficult conversations in the leadership and professional development world. We’ve created this mystique around them—like they’re these high-stakes moments you have to get RIGHT. That you only have one shot.

Think about the language we use: “Have the hard conversation.” Singular. We frame it as this one defining moment. The implication is that if you prepare enough, say it the right way, choose the right time—you can nail it in one go and boom—it’s done, everything’s all good after. Now I do want to acknowledge that I wrote an entire book framed around 10 conversations to have up the chain of command. My latest book, Managing Up: How to Get What You Need From the People in Charge, is all about that. But  I make a point right at the beginning to clarify: these aren’t ten one-time talks. They’re categories of ongoing dialogue. They’re cyclical. They happen in small doses, repeatedly, as situations evolve and as you build the relationship with your leadership and things change.

So we put a lot of weight on this one discussion. We want it to work. We want the relief of finally addressing something that’s been bothering us. We want validation that bringing it up mattered. We want some proof that we can influence the people who have power over our day-to-day work life.

And as you’re going through those pre-phases I mentioned earlier, something else is happening beneath the surface. You’re building this conversation up into something bigger than it actually is or can be. You start attaching outcomes to it that no single conversation can deliver. In your mind, once you have this talk, your boss will finally understand your value. The workload problem will be solved. The path to promotion will be clear. You’ll walk out of that meeting with relief, with clarity, with a plan.

It becomes a fantasy version of the conversation—perfectly laid out and executed, where you say exactly the right thing in exactly the right way, and they respond with exactly the validation or commitment you’re craving. The pressure builds because you’ve convinced yourself that this one interaction will change everything. That if you just nail this conversation, you’ll finally get what you need.

And this is where the “perfectionism” part comes in.

Because what you’re really doing is holding this conversation to an impossibly high standard. You’re not just hoping it goes well—you’re expecting it to go perfectly. All of the chips need to fall exactly into place as you’ve laid out in your head. It’s the same mentality as perfectionism in any other area: if I just prepare enough, control enough variables, execute flawlessly—I’ll get the outcome I want. 

You’re emotionally investing in a specific outcome that you’ve imagined but have absolutely no control over. And the more you rehearse, the more attached you become to that imagined version going exactly as planned. When it doesn’t? It feels like failure—even when nothing actually went wrong.

But conversations don’t work that way. They involve another human with their own constraints, pressures, and decision-making process that you can’t script or control. So when that ONE “big talk” doesn’t deliver all of that—when it’s ambiguous or incomplete or gets punted—we feel disappointed. Sometimes deeply so. Even when, objectively, the conversation went fine.

Okay, now that you understand what conversational perfectionism is and why it happens—even outside your best intentions and awareness—you’re probably wondering: what do I do about it?

The biggest place things need to shift is at the level of your expectations and framing going into these conversations. Because that’s what sets off the cascade of everything that happens after. If you go in believing this ONE talk will solve everything, you’re setting yourself up for disappointment before you even open your mouth.

So here’s the big lightbulb moment that happens for so many clients inside our Speak Like a Senior Leader program:

Hard conversations are a campaign. They are rarely—almost never—a one-and-done thing.

Let me say that again: these conversations are a campaign.

Think about the times you HAVE successfully pushed a change through or be able to get movement from your boss on something important. You bring something up once. Then you revisit it. You follow up. You check in. You bring it up again from a different angle. You provide updates. You ask clarifying questions. You reinforce your point with new evidence or examples. It’s an ongoing thread, not a single event.

And when I tell clients this, I can literally see the relief wash over them. Because suddenly, all that pressure they’ve been putting on ONE conversation? It loosens. It’s like they can deep breath because so much is no longer riding on it. They’re not trying to achieve EVERYTHING in 30 minutes anymore. They’re thinking strategically about how to move something forward over time, which is much more manageable. 

Hard conversations a campaign rather than a one-time thing. There’s a few reasons: 

From a practical perspective: you might catch your manager or leader off guard. Even if you’ve been thinking about this issue for weeks, this might be the first time they’re hearing about it. They weren’t mentally prepared to discuss your workload, or your career, or whatever the topic is. They need time to process what you’ve said because their mind and attention was probably on a completely different track. 

You’ve had weeks to formulate your thoughts. They’re getting this information in real-time, in the middle of everything else they’re juggling that day. Of course they’re not going to have a fully formed response on the spot.

Second, they often can’t act in that moment—even if they want to.

Let’s say you’re asking for additional headcount for your team or to put a new process in place. Your boss probably doesn’t have unilateral authority to make that decision. They need to get approval from their boss, or from HR, or from finance, from your partners in other departments. That takes time.

Or maybe you’re asking to be taken off a project or to have your responsibilities shifted. That creates dependencies—who’s going to pick up that work? Do they need to hire someone? Reassign tasks? Those logistics don’t get solved in a single 30-minute conversation.

And your boss doesn’t want to make promises they can’t keep. So instead of saying “yes, absolutely, consider it done,” they say “let me think about it” or “let me see what I can do.” That’s not them blowing you off. That’s them being realistic about what they can commit to in that moment.

Third, sometimes things just need time to pan out.

Maybe you’re bringing up concerns about a project’s direction, but there are details still being worked out with a client. Your boss might be waiting on information before they can make a decision. Or maybe there’s a bigger org change happening that impacts your situation, but it hasn’t been announced yet and your manager can’t disclose the details.  There are so many variables at play in any workplace situation that aren’t visible to you in that moment. Your boss might be thinking, “I hear what they’re saying, and I actually agree, but I need to wait until X happens before I can move on this.”

So when they give you a vague or noncommittal response, it’s not always them straight up resisting or dismissing you. 

What’s even more important to understand from a psychology standpoint is that influence doesn’t happen in a single conversation. It happens through repetition and exposure over time.

There’s a concept in marketing called the “Rule of 7″—the idea that a potential customer needs to see or hear your message at least seven times before they’ll take action. Some research suggests it’s even higher now, more like 20+ touchpoints before someone makes a buying decision.

Now, I’m not saying you need to have the exact same conversation with your boss 20 times. But the principle applies: people need to hear something multiple times, from multiple angles, before it really sinks in and they’re ready to act on it.

The first time you bring something up, you’re planting a seed. You’re getting it on their radar. You’re making them aware that this is something you care about.

The second time you mention it, you’re reinforcing that this isn’t a passing thought—it’s a real priority for you.

The third time, maybe you’re providing new information or context that helps them see it differently.

By the fourth or fifth time, they’re starting to take it seriously. Because they realize YOU are taking this seriously and this wasn’t just a passing request. 

When you approach that “big talk” not as a one time moment with all this build up, but approach it as a campaign, yes it DOES take more time. But you’re also WAY MORE likely to get what you want.

Because you’re not forcing your boss to make a snap decision. You’re giving them time to think, to consult with others if needed, to see how things play out. You’re showing persistence without being pushy. You’re demonstrating that this matters to you—not in a desperate, one-time plea kind of way, but in a consistent, grounded, “This is important” kind of way.

Managers respect that. They respect people who can advocate for themselves without beating them or others over the head with their demands, who understand that influence takes time, who don’t give up after one lukewarm response. 

It takes confidence and maturity to come back to the table, to bring something up again even after you’ve been somewhat rejected or dismissed. 

When you approach that “big talk” not as a one-time moment with all this build up, but approach it as a campaign, yes it DOES take more time. But you’re also WAY MORE likely to get what you want.

Because you’re not forcing your boss to make a snap decision. You’re giving them time to think, to consult with others if needed, to see how things play out. You’re showing persistence without being pushy. You’re demonstrating that this matters to you—not in a desperate, one-time plea kind of way, but in a consistent, grounded, “This is important” kind of way.

Managers respect that. They respect people who can advocate for themselves without beating them or others over the head with their demands, who understand that influence takes time, who don’t give up after one lukewarm response.

It takes confidence and maturity to come back to the table, to bring something up again even after you’ve been somewhat rejected or dismissed.

This is a skill. It can be learned. It can be practiced. It’s not something you’re born with or have magically bestowed on you once you reach a certain level. 

And this is exactly what we teach inside Speak Like a Senior Leader. Where you get world-class training and coaching on how to stay calm and composed leading up to those high-pressure moments so you’re not a bundle of nerves going in. We show you how to respond with dignity and gravitas when you don’t get the answer you were hoping for—when your boss is vague, or hesitant, or pushes back—and not let that derail you. 

And we teach you how to diplomatically raise the topic again. How to follow up without seeming pushy or like you’re nagging and get the outcome and result you need . 

Because let’s be honest: most of us were never taught this. We weren’t given a playbook for how to influence people who have more power than we do. We’rejust dripped into our roles and figuring it out as we go, making mistakes, second-guessing ourselves constantly.

Speak Like a Senior Leader gives you that highly tactical playbook to communicate at an executive level. And It’s my best-selling coaching program for a reason—because it’s the full system you need to be taken seriously at work. To have your level of expertise finally match how people treat you and the opportunities that come your way.

We show you how to translate the run-of-the-mill tasks you do every day—the stuff that feels like “just your job”—into business impact language that gets you pulled into strategy meetings and decision-making conversations.

We teach you how to distill complex ideas down quickly so when your meeting time gets cut in half or an executive asks you a question out of nowhere, you can deliver a crisp, confident answer instead of rambling or freezing up. And so much more.

We’ll be officially opening the doors for the next enrollment in Speak Like a Senior Leader™ at my upcoming free training on December 3rd that’s very aptly called Earn Up to $200k more in 2026: 5 Steps to Speak Like a Senior Leader. 

I’ll take you step by step through the exact roadmap you need to go from overlooked to sought for bigger projects and better roles. So just head to the show notes or melodywilding.com/training to grab your spot for that free event. 

If you take one thing away from today’s episode, I want it to be this reminder to yourself: The conversation you’ve been waiting to have doesn’t have to be perfect. It just has to happen.

You don’t need to nail every word. You don’t need your boss to give you a definitive answer on the spot. You don’t need everything tied up in a bow by the end. 

You just need to start the thread. Say the thing. Get it on the table. And then commit to keeping it going.

That’s all for today. If this resonated with you, do me a favor and share it on Linkedin or Instagram or with a friend or colleague who could use this.

Thanks again and I’ll catch you on the next episode.