How to Have Difficult Conversations With Your Manager
Difficult conversations with your manager fail for a reason most advice misses. Here's the real problem — and what both people in the room actually need.
By Dr. Latisha Chisholm — July 20, 2026
Subversive leadership is the stance, agency, and action to disrupt cultural reproduction — to stop harm you see, have seen, or have experienced. When the conversation about workload breaks down between an employee and a manager, it usually isn't because someone communicated badly. It's because neither person in the room was developed enough to see what they were actually looking at. Naming that gap is the first move.
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### The scene most of us have lived
One of my former team members reminded me of the time she told me I was gaslighting her. We can laugh about it now, but it wasn't funny for some time.
She had just finished telling me she was overwhelmed with her workload and asked me for solutions. My first suggestion was that we look at her calendar together. I think my suggestion offended her as much as her comment offended me.
She wasn't wrong to name her experience. I wasn't wrong to suggest the calendar. We were both operating without the framework to understand what we were actually looking at — and that gap is what made the moment land as harm.
Fortunately, we had a year of a supervisory relationship under our belt. There was a foundation of significant trust. She was skeptical but open to the possibilities I mentioned.
Over two months — with weekly calendar reviews as one of our strategies — she built the muscle to better assess her own capacity and priorities. Sustained retooling proved the intervention was right. But she had to go through two months of discomfort.
Most people don't get two months. They get one conversation.
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### What we think the problem is
The advice on this topic is almost universally about communication. Come prepared. Bring data. Document your tasks and time. Frame it as a business problem, not a personal complaint. Don't say "I'm drowning." Say "here's the impact on deliverables."
All of that puts the labor on the employee and quietly accepts one premise: the problem is how the conversation was delivered, not what it was trying to name.
That's the first layer. Underneath it is something more important.
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### What neither person in the room has been given
Overwhelmed and bad at planning look the same from the outside. They are not the same problem and they do not need the same response.
Resource problem: The workload genuinely exceeds what one person can do. The right response is organizational: redistribution, reprioritization, a real conversation about what gets dropped.
Capacity problem: The employee hasn't yet developed the skills to assess and manage competing priorities. The right response is developmental: a thinking partner, a structured tool, sustained retooling over time.
The calendar works for one, but is a misdirection for the other.
Most employees don't have the language to know which problem they're in. And most managers — even thoughtful ones — haven't been developed enough to reliably tell the difference. Without that shared language, the right intervention lands as harm. The wrong one goes unchallenged. This is one of the most concrete ways the hidden curriculum of professional workplaces shows up — not as missing information, but as missing vocabulary for what you are actually experiencing.
There is a cost to this that doesn't get named. When a resource problem gets incorrectly reframed as a capacity problem — when "my workload is unsustainable" becomes "let's work on your time management" — the employee pays twice. Once for the original problem, which still isn't solved. And again for carrying the weight of a structural failure that has just been handed back to them as a personal one. Research on code-switching and emotional labor documents how measurable that cost is — it shows up in how long people stay, in how much they trust the people above them, and in whether they ever bring the real problem forward again.
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### The manager's responsibility that rarely gets named
When you accept responsibility for leading people, you accept something most managers are never explicitly told: you are now accountable for their development, and for your own.
I am because we are. The Ubuntu principle that grounds the Subversive Leadership framework is not a platitude. It is a structural claim about how development actually works: the manager's capacity and the employee's capacity are not separate projects. They are co-constituted. To effectively develop others, you must also ensure you are effectively developed. And it is difficult to see what kind of problem they're in if no one has ever helped you learn to read the difference.
This is what the framework calls the two-layer liberation fantasy. The first layer is the vision for the people you serve. The second is the development of the adults doing the work. The second is not a secondary concern. It is the floor the first layer stands on.
That accountability isn't about having all the answers. It's about staying in the work long enough to find them. The calendar review was one move. What made it right wasn't the tool — it was the two months that followed. Showing up every week. Reassessing. Adjusting. Holding the thread of what we were trying to build together.
And it did not look like progress at first. Development that's doing real work rarely does. I have watched cohorts of young people move through a site I rebuilt from a team of three. The first cohort — recruited while the team was still forming, while the culture infrastructure was still new — retained at 42%. The cohort that arrived two years later, after sustained investment in the adults, retained at 84%. The work compounded. It just didn't announce itself in month one.
The skills to distinguish a resource problem from a capacity problem, to hold a long arc of retooling, to explain your reasoning in a way that lands rather than alienates — those don't come with the job title. They come from having had someone do that work with you. Most managers haven't. So they give what they were given, or they give nothing, and either way the person across the table is left to make sense of it alone.
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### What difficult conversations with your manager actually need
The difficult conversation about workload doesn't fail because of communication skills. It fails because both people are usually working without the one thing that would make it possible: development support that gives them language for what they're looking at.
When you have that language:
- You can name what kind of problem you're actually in — resource or capacity — before you walk into the room - You can hear "let's look at your calendar" as a diagnostic move, not a dismissal - You can say "I don't think this is a planning problem" and know what you mean when you say it - As a manager, you can explain why you're prescribing what you're prescribing, and hold the longer arc of what you're building with someone
Getting that language is exactly what leadership coaching actually does. Not scripts for managing up. Not frameworks for softening hard news. The capacity to see clearly what you're looking at, so the conversation you need to have becomes possible.
The villain in the workload conversation isn't the manager who suggested the calendar review or the employee who called it gaslighting. The villain is the absence of development support that left both of them in that room without the tools to understand what was happening between them.
That absence is what Subversive Leadership is built to name — and to change.
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### A question worth considering
Think about the last time a conversation about workload broke down — as the person asking or the person responding. What was the real problem? Did either person in the room have the language to see it?
Subversive Leader members: bring this to Zmara. She can help you name which problem you're actually in — before the next conversation.
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Dr. Latisha, EdD, LICSW, is the founder of Subversive Leader and the developer of the Subversive Leadership framework. She has spent two decades developing professionals in education, social work, and nonprofit leadership. Subversive Leader is an Ai-powered coaching platform built for early and mid-career professionals leading within systems that were not built for their success.