Issue 185, September 18, 2026 ✨ Higher Power Coaching & Consulting ✨

For years, I described myself as conflict-averse. I didn’t like conflict, and I assumed avoiding difficult conversations was how I “kept the peace.” But I wasn’t actually avoiding conflict. I was allowing it to take place entirely inside me. I didn’t realize that “keeping the peace” could actually include me.
I would replay what had happened, rehearse what I might say, imagine every possible reaction, and then say nothing. I’d keep doing more than I could reasonably do. I’d agree to deadlines I knew weren’t realistic and then I’d tell myself something wasn’t a big deal. Meanwhile resentment, anxiety, and exhaustion accumulated in my body, mind and spirit.
Silence doesn’t eliminate conflict. It often turns an interpersonal problem into an internal one.
This is especially common at work, where the stakes can be high. Your income, reputation, opportunities, health insurance, and sense of belonging may all feel tied to how you’re perceived. A conversation with a friend can feel risky. A conversation with a supervisor, client, or influential coworker can feel as though your livelihood is on the line.
That doesn’t mean every fear is accurate, and it doesn’t mean every workplace is safe. It means that having difficult conversations at work requires more than finding the perfect words. It requires enough internal safety to remain connected to yourself while you say something another person may not want to hear.
The problem usually isn’t that you don’t know what to say
When people ask me, “What do I say?” they’re often hoping there is a sentence so skillful that it will guarantee a good response. They think something like, “If I just had the right words, they’d hear me, agree, and all would be well.” They don’t want the other person to be disappointed, defensive, angry, or dismissive.
Of course, words matter. Timing matters. Tone matters. Preparation matters. But no script can control another person’s response, and the attempt to find one often becomes another form of avoidance. You keep refining your language because you’re trying to remove all risk before you speak.
The deeper task is to know what’s true for you, communicate it responsibly, and stay true to yourself when the outcome’s uncertain. That’s where workplace communication becomes a matter of self-trust and agency, not just a technique.
A difficult conversation might cover a variety of topics and relationships:
- telling your manager that your workload is no longer sustainable
- correcting an inaccurate assumption
- asking a coworker to stop interrupting you
- addressing a pattern of last minute requests
- negotiating compensation
- saying you need clearer priorities
- acknowledging that you made a mistake
The subject changes. The inner challenge is pretty much the same: Can I tell the truth without disappearing, attacking, overexplaining, or taking responsibility for everyone’s emotions?
How to prepare for a difficult conversation at work
The goal of preparation isn’t to make yourself invulnerable. It’s to create enough steadiness that you can act with intention while you’re still vulnerable. These ten practices can help.
1. Decide what the conversation is for
Before you plan what to say, identify the “job” of the conversation. Are you sharing information, making a request, correcting the record, setting a limit, addressing an impact, or asking for a decision? If you don’t know what you want the conversation to accomplish, fear can pull you into every grievance you’ve ever had.
A clear purpose might sound like this: “I want us to agree on which project takes priority,” or “I need to address how work is being assigned so we can prevent this from continuing.” You aren’t scripting the whole exchange. You’re giving yourself a place to return when the conversation becomes emotionally charged.
2. Separate the facts from the story
Write down what you directly observed before you interpret it. “The deadline moved from Friday to Wednesday” is a fact. “They don’t respect me” is a conclusion. Your conclusion may eventually prove accurate, but leading with facts gives the conversation firmer ground.
Then notice the story your nervous system is adding. You may be telling yourself that speaking up will make you difficult, ungrateful, disloyal, or expendable. Those fears deserve compassion, but they don’t automatically deserve decision making authority.
3. Know what matters to you
Difficult conversations become more manageable when you know what you’re standing for. Maybe it’s accuracy, fairness, sustainability, respect, quality, health, or integrity. Your values aren’t ammunition to use against someone else. They’re the ground beneath your own feet. Stand your ground.
This is one reason boundary work is inseparable from self knowledge. If you don’t know what you want, like, need, prefer and will tolerate, every conversation becomes a referendum on whether the other person approves of you. When you do know, you can listen and remain flexible without surrendering your center.
4. Assess the power and the actual stakes
Advice about speaking up at work can become irresponsible when it ignores power. A conversation with a trusted peer isn’t the same as a conversation with someone who controls your schedule, evaluation, income, or access to opportunities. A healthy response is not always to walk into the office and say exactly what you feel.
Ask yourself what authority this person has, what the workplace culture rewards or punishes, what documentation you may need, and whether you should consult a policy, representative, mentor, or other appropriate resource first. You can be courageous and strategic at the same time. Internal safety doesn’t mean pretending the environment is safe. It means seeing the environment clearly enough to make a conscious choice.
5. Bookend the conversation with safe support
Bookending is a practice I learned in recovery. You connect with an emotionally healthy person before and after doing something difficult. For workplace conversations, choose someone who can be objective and who won’t create additional risk by being drawn into workplace gossip. That person might be a coach, therapist, sponsor, mentor, or trusted friend outside the organization. Let’s call this person your Boundary Partner.
Before the conversation, talk through what happened, what you want, what you’re afraid of, and what you intend to say. Let the other person help you distinguish preparation from catastrophizing. Arrange to reconnect afterward so you don’t have to carry the emotional aftermath alone.
This isn’t asking someone else to decide for you. It’s receiving support while you make your own decision. That distinction matters. Self-trust doesn’t require isolation. And it’s helpful to get an objective perspective.
6. Regulate before you communicate
If your body believes you’re in danger, you may lose access to the thoughtful, capable part of yourself. You may freeze, become overly agreeable, talk too much, forget your main point, or escalate in an attempt to protect yourself.
Before the conversation, slow down enough to notice your body. Feel your feet on the floor or your body in the chair. Let your exhales become longer than your inhales. Look around the room and name what you see. Remind yourself of the date, your age, your role, and the choices available to you now. In other words, ground yourself in the present moment – you’re an adult in an office, not a 7-year-old on the playground being bullied. The purpose isn’t to make anxiety disappear. It’s to help your nervous system recognize that anxiety can be present without running the meeting.
7. Ask for a specific time and name the topic
A vague “We need to talk” can create unnecessary alarm. A more respectful opening gives the other person enough information to prepare: “I’d like to talk about the new reporting expectations and what they mean for my current deadlines. Is there a time today or tomorrow when we can spend 20 minutes on that?”
Getting agreement about timing isn’t the same as asking permission to have a legitimate concern. If the person repeatedly avoids the conversation, decide when you will follow up and what you will do next. Their avoidance doesn’t require you to abandon the issue. Putting a boundary around the amount of time for the conversation (in this case, 20 minutes) lets the other person and your nervous system know this isn’t going to be an endless conversation.
8. Stay with one issue and use concrete language
Choose one finite topic. Describe what has been happening, explain its impact, and state what you need. If the other person introduces every past frustration, you can say, “I’m willing to talk about that, but I’d like to finish this issue first and schedule another conversation for that topic if we need one.”
Concrete language is often kinder than vague language because it gives the other person something they can respond to. It’s easier to wrap your mind around and respond to clear language. For example: “Since the client review was added, I have three priority assignments due Friday. I can complete the review and the budget by then, or I can complete the presentation and the budget. Which two would you like me to prioritize?” That isn’t a complaint. It’s operational clarity.
9. Own your part without taking ownership of everything
Sometimes the most powerful way to begin is to acknowledge your contribution. You might say, “I agreed to this timeline without reviewing my existing commitments, and I need to correct that,” or “I realized I didn’t communicate the risk clearly enough last week.” Owning your part can lower defensiveness and demonstrate integrity.
But be careful. People who chronically overfunction often use accountability as a socially acceptable way to take all the blame. Owning your part doesn’t mean explaining away someone else’s behavior, apologizing for having a need, or accepting responsibility for a system that has been understaffed for years. Your part is your part. Their part is still theirs.
10. Define success before you go in
If success means the other person agrees, approves, changes immediately, and feels pleased with you, your well being remains in their hands. A more grounded measure of success is that you communicated honestly, stayed as connected to yourself as you could, listened for useful information, and followed through on what you said you would do.
The other person’s response is data. A thoughtful response tells you something about the relationship or workplace. So does dismissal, retaliation, avoidance, or repeated failure to change. The conversation may resolve the problem, begin a longer process, or clarify that communication alone cannot make the situation healthy. All three outcomes give you information you didn’t have while you were silently carrying the conflict.
What to do after the conversation
Reconnect with your Boundary Partner (the person who supported you before the conversation), and let your body come down from the experience. Ask them for emotional support and affirmation if they don’t automatically give it. If things went really well, this can just as important as if things didn’t go the way you hoped. That’s because the conversation can help you integrate the experience so your body gets, “I had a difficult conversation and I didn’t die.”
If things didn’t go as well as you’d hoped, they might say things like, “That sounds like it was difficult, and I’m here for you. You don’t have to deal with this alone” or “You deserve to be heard, and didn’t do anything wrong.”
Be sure to write down what was decided, what’s still unclear, and any follow up you need to do. If the conversation involved commitments, a brief written summary that’s emailed to all involved will help everyone remember the same next steps and make sure you’re all on the same page.
Also notice the urge to grade yourself. You may replay every sentence and decide you said too much, too little, too softly, or too firmly. Reflection can be useful, but rumination is often your nervous system trying to regain a sense of control. Ask a better question: What did I learn about myself, this person, and this workplace?
You may learn
- you can tolerate discomfort without collapsing (i.e., discomfort doesn’t mean danger)
- a relationship is more resilient than you thought
- your manager needed information you’d never provided
- the organization depends on your silence and over functioning
If the organization depends on your over functioning, the next boundary may not be another beautifully worded conversation. It may be documentation, escalation, a change in what you are willing to carry, or a decision about whether you can stay in that job.
The conversation is part of a larger practice
Having difficult conversations at work isn’t about becoming fearless, blunt, or endlessly confrontational. It’s about becoming someone who no longer requires herself to internally absorb every conflict in order to keep everyone else comfortable.
Sometimes the conversation will be awkward. Sometimes you’ll wish you had said something differently. Sometimes the other person won’t respond the way you hoped. None of that means you failed. You’re learning to remain in relationship with yourself while you participate honestly in your relationships with other people.
The deepest measure of success isn’t whether they liked what you said. It’s whether you stayed connected to yourself and your truth long enough to say what needed to be said.
For years, I believed avoiding conflict protected my relationships. What it actually protected was the pattern: everyone benefitted from my silence and my over giving pattern, and I paid the price internally. Learning to have difficult conversations didn’t make every situation turn out the way I wanted. It gave me a way to stop abandoning myself while I waited for other people to make my life workable (which never happened).
That is the larger practice: acting on your life instead of only reacting to what happens around you. The conversation is one moment. The agency you build by having it belongs to you long after the meeting ends.
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