Dealing with Difficult Stakeholders & The Stoic Response

From the beginning, they are demanding, uncommunicative about their own decisions, and when you can’t control their behavior, control your virtue, and watch relationships transform.

[Side note from Ryan: Welcome to all of our new subscribers from the LinkedIn Newsletter and the parent site at TheStoic.PM (I know, pretty on-the-nose, 'eh?)! I sincerely hope you get something out of these posts. If not, I want to know. I'm always open to feedback and suggestions. ~r]

The email landed in your inbox at 7 PM: “Why wasn’t I consulted on this decision? This is completely unacceptable. We need to meet first thing tomorrow to discuss your approach.” Your stomach tightened. This stakeholder had been difficult from the beginning, demanding, uncommunicative about their own decisions, and then critical when things didn’t align with unstated expectations.

You drafted three responses, deleted them all, and closed your laptop feeling defeated. 🙇🏻‍♂️

Every project manager faces difficult stakeholders: the executive who changes priorities weekly, the client who ghosts decision requests and then complains about delays, and the department head who sees your project as a threat to their turf (turf wars are the worst). These relationships drain energy, derail plans, and test your leadership to breaking points. Traditional advice would be to offer tactics such as active listening, managing up, stakeholder mapping, and so on. Still, it rarely addresses the deeper challenge of maintaining your composure, judgment, and integrity when someone else’s behavior pushes every button you have.

The Stoics lived this challenge daily. Marcus Aurelius managed a fractious Senate, rebellious generals, and scheming advisors while leading the Roman Empire. His solution, recorded in Meditations, wasn’t to control others but to master himself. That ancient wisdom offers modern managers/project managers a framework for transforming stakeholder conflict from an emotional battleground to an arena for practicing virtue.

Marcus Aurelius' Morning Meditation

Marcus Aurelius opens Book 2 of Meditations with brutal honesty, “Begin the morning by saying to thyself, I shall meet with the busy-body, the ungrateful, arrogant, deceitful, envious, [and] unsocial“ (Book 2, 2.1).

Begin the morning by saying to thyself, I shall meet with the busy-body, the ungrateful, arrogant, deceitful, envious, unsocial.

Read that again. The Roman Emperor, the most powerful person in the known world at that time, started his day expecting difficult people. This wasn’t pessimism or cynicism. No, it was rational preparation. By rehearsing the reality of human nature through negative visualization, Marcus eliminated surprise, the enemy of rational judgment.

But he didn’t stop there. He continued, “But I who have seen the nature of the good that it is beautiful, and of the bad that it is ugly, and the nature of him who does wrong, that it is akin to me…” (Book 2, 2.2). This is the Stoic move that changes everything. Difficult people act from ignorance, not malice. They’re struggling, just like you, to navigate competing pressures and incomplete information.

Their behavior is external, outside your control. Your virtue, i.e., wisdom, justice, courage, and temperance, remain entirely within your power. This distinction is the foundation of Stoic stakeholder management.

Why Stakeholder Conflicts Derail Projects

Difficult stakeholders aren’t edge cases; they’re the norm. Research shows communication breakdowns and stakeholder misalignment are among the top causes of project failure. The specific manifestations vary, but you can count on executives who demand scope additions without timeline adjustments, clients who delay approvals and then blame you (or your team) for missed deadlines, or functional leads who protect their territory rather than support cross-team collaboration.

Not to sound like a list of medication side effects, but common sources of stakeholder difficulty include competing priorities across organizational silos, information asymmetries that breed frustration, resource constraints that create zero-sum competition, and unclear roles that foster blame games. Add personality clashes, political pressures, and past organizational baggage, and you’ve got a powder keg that ignites regularly.💥

Traditional project management responses fall into three categories, and all are flawed:

Appeasement: Say yes to every demand, overwork your team, burn out, and still face criticism when impossible commitments fail.

Avoidance: Minimize stakeholder interaction, hope issues resolve themselves, and discover too late that misalignment has doomed the project.

Aggression: Push back hard, escalate quickly, win battles but lose wars as relationships deteriorate and future collaboration becomes impossible.

These approaches fail because they focus on trying to control externals; the stakeholder’s behavior, opinions, or decisions, which lie fundamentally outside your power. The Stoic approach inverts the strategy to “master your controllables“ so completely that the relationship transforms without requiring the other person to change.

Stoic Principles for Stakeholder Relationships

Two Stoic concepts form the foundation for dealing with difficult people: sympatheia and the dichotomy of control.

Sympatheia, often translated as “mutual interdependence,” holds that all parts of a system are connected like organs in a body. Marcus wrote, “For we are made for co-operation, like feet, like hands, like eyelids, like the rows of the upper and lower teeth. To act against one another then is contrary to nature; and it is acting against one another to be vexed and to turn away” (Book 2, 2.4-5).

Applied to projects, this means your difficult stakeholder isn’t your enemy. Rather, they’re part of your ecosystem. Their resistance, demands, or poor communication likely stem from pressures you don’t see, e.g., board scrutiny, budget threats, competing initiatives, or personal insecurities. Understanding their context doesn’t excuse harmful behavior, but it depersonalizes conflict and reveals collaborative solutions.

The dichotomy of control divides everything into two categories: what’s up to you and what isn’t. Epictetus taught that suffering comes from trying to control externals such as other people’s thoughts, actions, and outcomes, while neglecting what we actually command: our judgments, choices, and responses.

For project managers facing difficult stakeholders:

Not in your control:

• Their communication style, tone, or timing
• Their availability or responsiveness
• Political pressures on them from their leadership
• Past organizational experiences that are shaping their distrust
• Whether they like you or approve of your approach

In your control:

• The data and options you present
• Questions you ask to understand their constraints
• Boundaries you establish around scope, timeline, and resources
• Your tone, patience, and emotional steadiness
• Follow-up actions and documentation
• When and how to escalate issues

The Stoic PM focuses 100% of their energy on the controllables and releases the rest. This doesn’t mean passivity; it means strategic, virtuous action on what actually moves the needle.

Five Stoic Moves for Difficult Stakeholders

Here’s how to apply Stoic philosophy to transform stakeholder relationships through virtue.

Move 1: Morning Expectation Setting

Adapt Marcus’s morning meditation before high-stakes stakeholder interactions. It will amaze you what spending five minutes writing can do (I'll even do this on the bus or carpooling (when I'm not driving)):

“In today’s steering committee meeting, the CFO may interrupt, dismiss my risk data, or demand we cut timeline by 30%. I cannot control their reaction. I can control my preparation, my calm tone, my advocacy for the team, and my willingness to present hard truths with evidence.”

This practice eliminates surprise. When the CFO does interrupt aggressively, you’re not emotionally hijacked because you anticipated this possibility and preset your virtuous response. You stay centered while others react.

Move 2: Real-Time Dichotomy Sorting

During tense stakeholder exchanges, practice mental dichotomy sorting. When the client says, “This timeline is completely unacceptable,” your internal dialogue runs:

• External (release): Their frustration, their board’s pressure, whether they respect me, and their approval of this timeline.
• Controllable (engage): Presenting alternative scenarios with trade-offs, asking what outcome matters most to them, maintaining professional tone, and documenting agreements.

This prevents defensive reactions and possibly a visible skew of your face. You’re not arguing with their feelings (external); you’re engaging their problem-solving with options (controllable).

Move 3: Practicing Sympatheia Through Empathy

Stoic empathy means understanding context without condoning harmful behavior. When a stakeholder acts difficultly, ask yourself, “What pressure is this person under that I don’t see?”

The executive demanding scope additions may be facing a board ultimatum about market share. The department head resisting your project may fear that their team’s jobs are threatened. The client's ghosting decisions may be a result of navigating internal chaos.

Turn this analysis into action with one powerful question before responding, “Help me understand the constraint you’re navigating—what would success look like for you?” This shifts the conversation from positions (my timeline vs. your scope) to interests (we both need delivered value and manageable risk).

Move 4: Clear Boundaries Rooted in Justice

Justice, in Stoic terms, means giving each person their due, including your team. When stakeholders demand unreasonable scope, compressed timelines, or rule-breaking shortcuts, Stoic leadership requires courageous boundaries.

The technique: State facts calmly, present trade-offs transparently, and hold the line on what serves the project and protects the team.

Example, “I understand the pressure to add these features. Adding them mid-sprint requires either extending the deadline by three weeks or removing Features X and Y from this release. Both options are viable, but which aligns better with your strategic priority?”

Notice the elements:

• Wisdom: Frame choices, not refusals
• Justice: Protect team capacity and quality standards
• Courage: Present reality even when uncomfortable
• Temperance: No over-explaining, defending, or emotional pleading

You’re not controlling their decision (external); you’re controlling the clarity, options, and boundaries you provide (controllable).

Move 5: Strategic Distance When Warranted

Marcus advised keeping your guard up with people who bite and scratch, and limiting exposure to those who consistently harm you. Stoicism isn’t martyrdom.

In project terms, if a stakeholder engages in verbal abuse, unethical demands, or consistent sabotage, use controllables to create a protective structure:

• Shift from open-ended meetings to time-boxed, agenda-driven sessions
• Use written communication for decisions to create documentation
• Delegate the relationship to a sponsor or project liaison better positioned to manage it
• Escalate to governance when behavior violates organizational values

This isn’t avoidance; it’s rational risk management of your controllables (your time, your team’s exposure, your communication channels).

Real-World Case: The Hostile Sponsor Transformation

A healthcare IT project faced a classic difficult stakeholder: the executive sponsor sent aggressive emails criticizing decisions, skipped steering committee meetings, and then demanded last-minute scope changes, blaming others when timelines slipped.

The project manager (who happened to study Stoicism) conducted a dichotomy analysis:

Externals (not controllable):

• Sponsor’s communication style and emotional state
• Their attendance at meetings
• Political pressures on them from the board
• Their past experiences with failed IT projects

Controllables:

• Meeting structure and communication cadence
• Information provided and format
• Change control process and boundaries
• My tone and empathy in responses
• Escalation path if behavior becomes abusive

The PM took four actions:

1. Empathy conversation: Requested a one-on-one with the prompt, “I want this project to succeed for you. What outcome matters most, and what obstacles are you facing?” Discovery: The sponsor was under intense board scrutiny after a prior IT failure. They feared this project’s failure would cost them their role, hence the controlling, anxious behavior.

2. Structured communication: Replaced ad-hoc email battles with a 15-minute weekly status call plus a simple dashboard showing progress, risks, and decisions needed. This gave the sponsor predictable visibility and control, addressing their underlying anxiety.

3. Transparent change control: Implemented a lightweight change request form, “Happy to adjust scope, however, here’s the timeline and budget impact. Your call on whether the trade-off serves our goals.” Shifted from arguments to informed decision-making.

4. Morning preparation: Before each sponsor interaction, the PM practiced Marcus’s meditation, “They may be curt or critical. I cannot control their tone. I will stay calm, listen for the underlying concern, and advocate for the team’s needs.”

Results over 8 weeks (yes, it can take a while):

• Hostile emails dropped by ~80%
• Sponsor attended 100% of steering meetings
• Scope change requests came through the proper process with thoughtful trade-off discussions
• Project delivered on time; sponsor became a vocal advocate for the team

The transformation didn’t require the sponsor to change (external). It emerged from the PM’s mastery of controllables: structure, empathy, boundaries, and virtue under pressure.

When to Escalate or Exit

Stoicism is not doormat philosophy. Marcus also wrote about protecting yourself from wrongdoers and avoiding people who consistently cheat or abuse.

If a stakeholder demands unethical actions, verbally abuses team members, or consistently violates organizational values, Stoic courage means escalation or exit. You control your boundaries, “I cannot deliver this project under conditions that harm my team or compromise our professional standards.” Then escalate to governance, request a reassignment, or, in extreme cases, leave.

This is justice, protecting what’s right and giving your team their due, even when the outcome (the stakeholder’s reaction, organizational politics, your reputation) remains external. Virtue matters more than comfort.

Practice: Build Your Stoic Stakeholder Habits

Theory becomes power through daily practice. Three exercises this week:

1. Morning Stakeholder Meditation (5 minutes): Before a challenging stakeholder interaction, write, “This person may [specific difficult behavior]. I cannot control that. I will respond with [specific virtue—wisdom, justice, courage, or temperance].” Review before the meeting.

2. Dichotomy Mapping (15 minutes): Choose your most difficult stakeholder. Draw two columns: “In My Control” and “External.” List everything about the relationship, their behavior, your responses, meeting structure, communication patterns, and outcomes. This week, take action only on items in the controllable column. Notice what shifts.

3. Empathy Question Practice: In your next tense stakeholder conversation, pause before presenting your solution. Ask one genuine question about their constraints or priorities, maybe, “What’s the biggest pressure you’re facing on this?” or “What would success look like from your chair?” Listen fully to their answer before responding.

Final Thought

Marcus Aurelius wrote his reflections not as an emperor addressing subjects but as a student coaching himself through difficulty. One of his most famous passages addresses difficult people directly: “Begin each day by telling yourself: Today I shall be meeting with interference, ingratitude, insolence, disloyalty, ill-will, and selfishness.” But he continued, “All this has happened because they do not know the difference between good and evil.”

Your difficult stakeholders aren’t villains. They’re people under pressure, navigating competing demands with incomplete information and their own fears. You cannot control their behavior. However, you can control your preparation, your boundaries, your empathy, and your virtue.

It's almost a paradox. When you stop trying to control their response and master your own, the relationship often transforms. Not always, unfortunately. Some stakeholders remain difficult no matter what you do. But even then, you’ve won what matters. You’ve acted with wisdom, justice, courage, and temperance. You’ve led your team well. You’ve maintained your integrity under pressure.

That’s the Stoic victory. Not changing others, but becoming the kind of leader who handles difficulty with grace.

Who’s your difficult stakeholder? This week, practice one Stoic move. Control what you can. Release the rest. Watch what happens.

Aurelius, M. (n.d.). Meditations (G. Long, Trans.). The Internet Classics Archive. https://classics.mit.edu/Antoninus/meditations.2.two.html