Mastering Feedback: How to Have Difficult Conversations at Work
- amberkinser0
- Sep 16
- 3 min read
Updated: Sep 28
When I first became a department chair, one of the hardest lessons I learned was this: leadership is as much about the conversations you dread having as it is about the ones you look forward to.
I'll never forget a difficult work conversation with a faculty member whose classroom performance was slipping. I cared deeply about this colleague, but I also had a responsibility to the students and to the department. My fear? That raising the issue would damage our relationship.
It didn't have to. Over time, I learned that giving honest feedback is not only possible without harming relationships, it can actually strengthen them. Here's how.
Get my ready-to-use free guide to difficult conversations and keep it handy the next time a tough conversation shows up on your calendar.
Whey Feedback Feels So Hard
In my early leadership days, I sometimes avoided direct conversations, hoping issues would resolve themselves. Spoiler: they didn't. What I learned is that postponing feedback only increases tension and resentment.
Concern About Damaging Trust
I used to believe honesty would create distance between me and colleagues. What I discovered was the opposite: handled well, feedback builds trust by showing you're invested in growth, not avoidance.
Lack of a Clear Framework
Most leaders were never formally trained in how to handle a difficult work conversation. Without a framework, it's easy to either soften the message too much or come across too harsh.
Want a practical framework? Download my free guide to difficult conversations for step-by-step strategies you can use right away.
Strategies for Honest Feedback that Builds Relationships
Lead with Curiosity
When I entered conversations with assumptions ("This person just isn't trying"), I usually hit a wall. But when I led with curiosity and asked about their perspective first, I opened the door to dialogue rather than defensiveness.
Balance Directness with Care
It took me a while realize: clarity is kindness. Saying, "Your grading turnaround time is too slow" is more helpful than vague hints like, "Maybe you could get grades back sooner." Pairing directness with a caring tone kept the relationship intact.
Anchor Feedback in Shared Goals
One way I reframed conversations was by connecting them to goals we both valued: student success, departmental reputation, professional growth. This shifted the feedback from me vs. you to us working toward the same thing.
Use Structure to Stay Grounded
The most effective feedback conversations I had followed a structure: describe the behavior, explain the impact, invite dialogue, and co-create solutions. This kept me focused and less likely to spiral into defensiveness or over-explaining.
For more details on structuring these conversations, check out How to Have a Difficult Conversation with Your Employee.
The Leadership Advantage of Honest Feedback
When I avoided hard conversations, problems festered and morale dipped. But when I leaned into them with care and clarity, I noticed something powerful: relationships often grew stronger. Colleagues felt seen, respected, and supported, even if the conversation was tough.
This is especially true in academia, where relationships can span decades. Preserving long-term trust while addressing immediate issues is essential. In fact, I wrote about this unique challenge in The Dean's Guide to Difficult Conversations.
Giving feedback doesn't have to mean damaging relationships. Actually, the opposite is often true: by leaning into curiosity, clarity, and care, you show that you're invested in the other person's growth as much as your own.
As leaders, we don't get to avoid difficult work conversations but we do get to choose how we approach them. When handled with structure, empathy, and transparency, feedback becomes less of a threat and more of a bridge.
If you're ready to build your confidence in these moments and stop letting difficult conversations derail you, let's talk.
Schedule your free Discovery Call today.
Comments