Giving the Toughest Feedback

I’m changing the way I give the toughest feedback. A former team member helped me see a blind spot–as their manager, I had given what I thought was clear, principled feedback about performance concerns. I had the data, used frameworks, and provided a path forward. I thought I was being a good leader.

I missed something simple: I hadn’t created space for their perspective. I went straight into script mode, with SBI observations and action items. While the feedback itself was necessary, my approach left them feeling unseen and undervalued. But I did see them, and I did value them, and I let them down by not inviting their perspective when it mattered most.

Psychological safety, core engagement, empowerment, and fierce communication are all north-star principles for my leadership style. Yet in this crucial moment, I didn’t practice what I teach. I chose efficiency over empathy, confusing directness with one-way communication.

The cost was huge. It damaged a relationship I valued, hurt trust, and the feedback ultimately landed as judgment rather than opportunity for change and growth. In this failure, I learned something vital: true leadership isn’t just about having the courage to give hard feedback - it’s about that moment and the moments after that make feedback effective and keep high trust and safety.

This is how I’m changing my approach to difficult conversations.

Principles

• Clarity is kindness - unclear feedback deprives people of the opportunity to grow
• Everyone deserves to be heard - gaps in perspective may create blind spots
• Create the path forward together - ownership drives lasting change
• Don’t be a good leader and a bad manager - principles without practice harm relationships

Antipatterns

• Softening feedback to protect feelings (actually makes things worse)
• Rushing to corrective actions or solutions before understanding context
• Focusing on intention (“I meant well”) over impact
• Avoiding documentation of clear expectations

Before the Conversation

The first step is ensuring you’re prepared to have the conversation, and because specifics matter, they need to be collected and documented.

1. Document specific examples
2. Write down 2-3 key questions
3. Define clear success metrics
4. Schedule adequate time (45-60 min)
5. Choose a private, neutral space

During the Conversation

Opening: Set boundaries

• “I want to discuss (specific situation/pattern) because it’s impacting (bottom line outcome). It might be a little heavy.”

This explains the situation and sets the tone for the conversation by setting the boundary: what is the most important thing to discuss, and why does it matter to the business?

Exploration: Invite their perspective

• “How do you see this situation?”
• “What might I be missing?”
• “What factors are influencing your approach?”

Everyone deserves to be heard. While you may have a fact pattern, it’s important to let the other person qualify the situation in their own words.

Direct feedback: Clear + specific

• “Here’s what I’m observing: (specific examples)”
• “The impact is: (concrete outcomes)”

Clarity is kindness; the goal isn’t to soften the feedback, but to clearly state why this matters and what the observational impact is.

Joint problem-solving:

• “What support would help you address this?”
• “Here’s what success looks like: [clear expectations]”

This empowers the other person to take ownership of the solution and externalize what they may need to meet the expecations. It respects their agency while holding them accountable for change.

I’ve opted for more directness in feedback, which is important, but I’m also trying to bring more openess to the conversation.

Phrases that maintain directness while showing openness:

• “I have specific concerns we need to address. First, I’d like to understand your view.”
• “This pattern needs to change. Help me understand the barriers you’re facing.”
• “I’m being direct because this matters. What am I missing from your perspective?”

For the next tough feedback conversation

For managers:

• What am I trying to protect by softening this message?
• Have I gathered multiple perspectives?
• Am I clear on the non-negotiables?
• What support am I prepared to offer?

For the conversation:

• Did they feel heard?
• Were expectations clear?
• Is there a documented path forward?
• Did we address root causes?

After the Conversation

• Document agreements
• Schedule check-ins
• Watch for early wins
• Provide specific positive feedback when you see change

Resources

• Don’t soften feedback
• Advanced Coaching Questions by Paloma Medina, author of BICEPS.