The Right (and Wrong) Way to Handle Tough Conversations
Practical tips guiding women from reliable team player to well-paid leader.
TL;DR: Difficult conversations are challenging on both sides - we struggle to deliver criticism effectively, and we tend to internalize negative feedback disproportionately. Research shows women and people of color receive more personality-based feedback and less actionable criticism that would help them improve. Learning to both give and receive feedback effectively is essential for career growth and leadership development, and it's a skill you can master with the right approach.
Hey there 👋
Why are difficult conversations so… difficult?
If you’re like me, you can remember every negative comment you’ve ever received—but the positive ones? A blur. And when it’s time to give feedback, it’s easy to either soften it too much or come across too harsh.
I once had to let someone go, and I was so indirect that they thought they were getting a promotion. Another time, I agonized over the best way to say it, until a friend gave me a reality check:
"That’s disrespectful. If you want to treat them with dignity, be clear and direct."
It was hard, but I did it. And it taught me a critical lesson: how we give and receive feedback shapes our careers more than we realize.
The Problem Pattern: Why Difficult Conversations Undermine Authority
Have you ever caught yourself in these scenarios?
Spending hours crafting an email about performance issues, only to water it down beyond recognition
Sitting through a performance review where you only hear the one negative comment amid a sea of praise
Giving someone vague feedback that leaves them confused about how to improve
Internalizing criticism so deeply that it shakes your confidence for weeks
These patterns aren't just annoying habits—they're career-limiting behaviors that undermine both your authority and your ability to grow.
Research from Textio shows women receive 22% more personality feedback than men and far less actionable guidance. Black employees face even greater disparities, receiving twice as much unactionable feedback as their white and Asian counterparts. What's worse, this kind of vague, personality-based feedback triggers stereotype threat, where people worry about confirming negative stereotypes about their identity group.
These feedback inequities create a vicious cycle: without clear guidance on how to improve, historically marginalized groups are less likely to advance and more likely to internalize negative messages about their capabilities.
How Most People Try to Solve It (And Why It Fails)
The standard approaches to feedback often miss the mark:
The "Sandwich Method": Burying criticism between compliments seems kind but typically fails because:
People see through the formula
The actual feedback gets lost
Recipients focus on either only the positive or only the negative
It comes across as inauthentic
The "Just Be Direct" Approach: Simply "being more direct" without the right framing can backfire because:
Blunt criticism without context feels personal
Different groups may interpret directness differently
It doesn't provide a path forward
It can damage relationships without strategic delivery
Neither approach addresses the psychological and social dynamics of difficult conversations. They ignore how different groups experience feedback, how power dynamics affect these exchanges, and how our brains process criticism.
In that Textio report (super interesting - worth a read) the researchers (from Stanford) note we need a much more nuanced approach to feedback that takes into account both the message and the messenger.
The Real Cost of Avoiding Difficult Conversations
Avoiding or mishandling difficult conversations carries significant costs:
For Teams: Performance issues fester, bad patterns become ingrained, and team trust erodes when problems go unaddressed.
For Recipients: Without specific, actionable feedback, people can't improve—they're left guessing what's wrong or, worse, internalizing vague criticism as character flaws.
For Leaders: Your authority diminishes when you can't have straightforward conversations. Research suggests high performers actually value constructive feedback—and leave when they don't receive it.
For Underrepresented Groups: The feedback gap becomes a career advancement gap. According to the Textio report, people who receive low-quality feedback are 63% more likely to quit within a year—even when that feedback is positive in nature.
The real issue isn't about being "nice" versus "mean"—it's about providing clear, specific guidance that helps people succeed while preserving their dignity.
A Strategic Approach: 5 Common Mistakes and What to Say Instead
After 30 years of tough conversations—firing people, navigating divorce and remarriage, raising four kids, and managing teams through crisis—I've learned that most people make the same mistakes in difficult conversations.
Before diving into those mistakes, let me share a powerful framework that research shows reduces anxiety for both the giver and receiver of feedback. The Center for Creative Leadership's Situation-Behavior-Impact (SBI) model provides a simple structure that keeps feedback specific and actionable:
Situation: Describe the specific context. "Yesterday during the client presentation..."
Behavior: Focus on observable actions, not assumptions or personality traits. "You interrupted Sarah three times while she was explaining the financial projections."
Impact: Share the effect this had. "This caused her to lose her train of thought and made it seem like our team wasn't aligned."
Intent: (Optional, but powerful) Ask about their purpose. "What were you hoping to accomplish in that moment?"
This structured approach is particularly valuable for women because it helps navigate the "double bind" of needing to be both warm and authoritative. It keeps the focus on specific behaviors rather than personality traits—particularly important since research shows women receive 22% more personality-based feedback than men.
Now, let's look at the 5 common mistakes people make when giving feedback, and how to avoid them using this framework:
1. Stop dancing around the point
Why it fails: Dancing around the issue prolongs discomfort, creates confusion, and actually feels less respectful to the other person.
What women can actually say: "I wanted to talk with you today about some concerns with recent performance. Specifically, [clear issue]."
"I need to share some difficult news. The company has made the decision to eliminate your position. Let me walk you through what this means."
Why this works: This approach clearly sets up the situation before addressing the specific behavior, following the SBI framework.
2. Master the art of silence
Why it fails: Jumping in to fill every quiet moment prevents the other person from processing, blocks authentic responses, and often leads to backtracking or over-explaining.
What women can actually say: [Attentive silence with open body language]
"I understand this is a lot to take in. I'm here to listen when you're ready."
"Take whatever time you need. I know this is significant information."
Why this works: Creating space without creating awkwardness demonstrates empathy without apologizing and maintains professional boundaries.
3. Own your words
Why it fails: Phrases like "You always" and "You never" create immediate defensiveness, focus on personality instead of behavior, and escalate emotions.
What women can actually say: "I've been looking at the project timeline, and I noticed the last three deadlines weren't met."
"When we discussed client communication, we agreed on a different approach than what happened with the Anderson account. I'd like to understand where the disconnect happened."
Why this works: This approach focuses on observable patterns, uses "I" statements without apologizing, and creates opening for problem-solving rather than blame.
4. Keep your cool
Why it fails: Losing emotional control escalates tension, undermines your message, and creates moments you'll later regret.
What women can actually say: "This is obviously a challenging conversation, and I appreciate your willingness to have it."
"I recognize this feedback may be difficult to hear. My intention is to find a path forward that works for everyone."
Why this works: Acknowledging emotions without centering them maintains a professional tone while showing appropriate empathy and redirects the conversation toward solutions.
5. Don't get derailed
Why it fails: Allowing the conversation to go off on tangents loses focus, prolongs the process, and often leads to capitulation on important points.
What women can actually say: "I understand your perspective on [side issue]. For today, we need to focus on [main issue]. Can we come back to that other point afterward?"
"Those are important points about past situations. Right now, we need to address the current situation and next steps."
Why this works: This approach acknowledges their concerns without getting sidetracked, sets boundaries without seeming rigid, and creates a pathway back to the main discussion.
Remember, your goal is to be:
Clear while maintaining relationship
Direct while showing appropriate empathy
Boundary-setting while remaining professional
You are not responsible for:
Managing their emotional reaction
Solving all related problems in one conversation
Answering for decisions you didn't make
The Structure of Effective Feedback That Works For Women
Research from on feedback bias shows that the most impactful feedback follows a specific structure that helps women navigate the double bind of needing to be both warm and authoritative:
Receiving Feedback Strategically
Women tend to internalize criticism more than men do. Here's how to receive feedback without letting it undermine your confidence:
4. Adjust for Cross-Cultural and Gender Differences
Awareness of how feedback is received across different groups is crucial:
Women tend to internalize negative feedback as reflective of their abilities, while men often attribute it to external factors
High-context cultures may expect more nuance and relationship-building before direct feedback
Stereotype threat can cause historically marginalized groups to experience even constructive criticism more negatively
5. Follow Through After Difficult Conversations
The conversation is just the beginning:
Document key points and agreements
Schedule follow-up discussions
Acknowledge progress and improvement
Rebuild the relationship through positive interactions
👉 Power Practice for the Week
Monday: Reflect on the last difficult conversation you had. What went well? What could have gone better?
Tuesday: Tuesday: Practice the SBI (Situation-Behavior-Impact) framework for one piece of feedback you need to deliver.
Wednesday: Ask a trusted colleague for specific feedback on one aspect of your work. Practice receiving it without defensiveness.
Thursday: Have the difficult conversation you've been avoiding, using the structure outlined above.
Friday: Follow up with the person you spoke with, acknowledging the conversation and reinforcing your support for their growth.
A friend recently told me about a session with her executive coach, aimed at helping her giving feedback to a team lead who was alienating team members. Instead of saying "You're too aggressive in meetings" (personality feedback), she counseled her to say: "When you interrupt colleagues during presentations, they disengage and valuable ideas get missed. How might we ensure everyone's contributions are heard?" This perfectly illustrates the SBI framework: she identified the situation (presentations), the behavior (interrupting colleagues), and the impact (disengagement and missed ideas).
The Short of It ⚡
Specific, behavior-focused feedback is more effective than personality commentary
Different groups receive and process feedback differently—women and people of color get more personality-based criticism
The best feedback addresses behavior, impact, and creates a path forward
Psychological safety dramatically improves how feedback is received
High performers actually value constructive criticism when it helps them grow
How you receive feedback is just as important as how you give it
Following up after difficult conversations reinforces the message and rebuilds trust
Remember, the goal isn't to make difficult conversations easy—they rarely will be. The goal is to make them effective, respectful, and growth-oriented. Difficult conversations are unavoidable, but with the right approach, they don’t have to be career-limiting.
With you all the way,
- Kara
P.S. Next week we'll tackle the "broken rung" - that critical first step to management where women are significantly less likely to be promoted than men. For every 100 men promoted to manager, only 87 women receive the same opportunity, creating a bottleneck that affects the entire pipeline. I'll share strategies for navigating this barrier and positioning yourself for that crucial first promotion.
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