Coaching practices for I Have to Tell Someone Something Hard About Their Work and I'm Dreading it Because Every Time I Do it Lands Like an Attack and They Go Defensive I Want Us on the Same Side of This Not Facing Off Across it
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Does this sound like the set of challenges you might be facing?
- I have to tell someone something hard about their work and I’m dreading it, because every time I do it lands like an attack and they go defensive
- When I finally say the hard thing it comes out as my blunt conclusion delivered like a verdict, and the other person’s walls go straight up
- I’m dreading this talk because I know they’re already thinking the worst of me
- Every time I bring something up it comes out as "you did this, you always do that," and they hear an accusation and dig in
- I have to make an ask that I know is going to land as self-serving or unfair, and I’m dreading the moment they think it
Practices that may help
- Give and receive feedback with courage
Sit on the same side of the table: feedback as a shared problem, not an attack.
Daring Greatly, Made Practical - STATE your path
Share your view honestly but in a way that keeps the other person open: facts first, then story, tentatively.
Crucial Conversations, Made Practical - The accusation audit
Pre-empt their worst objections by saying them out loud before they can.
Tactical Empathy - Lead with how you feel, not what they did
Open with "I feel [emotion] when [situation]" before describing what you want changed.
The Soft Startup: How You Begin a Difficult Conversation Determines How It Ends - Run an accusation audit before difficult asks
Name the worst things the other person might think about you or your request — before they do.
Labeling Emotions in Negotiation, Made Practical - Challenge directly
Say the hard thing clearly, soon, and to the person’s face.
Radical Candor, Made Practical - Name the antagonist: what is the obstacle, not who
Every compelling story has something working against the protagonist — name the force, not a person.
Storytelling for Persuasion, Made Practical - Find mutual purpose
Establish a shared goal both people care about so the conversation is "us vs the problem".
Crucial Conversations, Made Practical - Adapt how you deliver feedback to the person’s style
Deliver the same honest feedback in the form the other person can actually hear it.
The Platinum Rule - Delivering honest feedback without cruelty
Be completely truthful about a problem and completely non-cruel in how you deliver it.
Ahimsa: Non-Violence as a Daily Practice
Related concerns
- Speaking Hard Truths
Share your view honestly but in a way that keeps the other person open: facts first, then story, tentatively.
STATE your path
- When Emotional Agility Emotional Courage
Identify the difficult conversation you’ve been postponing and have it — using discomfort as a signal to act, not avoid.
Social Discomfort: Deliberately Having the Conversation You’ve Been Avoiding
- When Ahimsa Nonviolence Ahimsa In Feedback
Be completely truthful about a problem and completely non-cruel in how you deliver it.
Delivering honest feedback without cruelty
- Confront Brutal Facts
Name the most uncomfortable true things about your current situation before acting, planning, or optimizing.
Confront the brutal facts — regularly and specifically
- How To Give Honest Advice
Deliver the same honest feedback in the form the other person can actually hear it.
Adapt how you deliver feedback to the person’s style
- When Circle Process Open With Values
Shared values create the psychological container that makes honest dialogue possible.
Open every circle by naming shared values
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