Stop Avoiding Feedback: A CEO’s Guide to Honest, Relationship-Building Conversations

You Can Be Direct Without Being Unkind

If you hesitate to give constructive feedback because you value your relationship with the person, that hesitation is understandable. As a founder or CEO, you may have worked alongside them through difficult launches, changing priorities, and long stretches of uncertainty.

But protecting a relationship is not the same as protecting someone from uncomfortable information. When you delay, expectations remain unclear, frustration can accumulate, and the employee loses an opportunity to improve.

The goal is not to make feedback painless. It is to make it clear, fair, and useful. You cannot guarantee that someone will feel positive immediately, but you can treat them with respect throughout the conversation.

1. Turn Your Concern Into Something Observable

Before scheduling the conversation, separate what happened from what you assume it means.

Instead of writing, “They don’t take ownership,” identify the behavior: “The last two project updates arrived after the agreed deadline, without advance notice.”

Prepare three things:

• The observation: What specifically happened, and when?
• The impact: What did it affect—customers, colleagues, decisions, or delivery?
• The expectation: What needs to happen differently?

Check your own contribution, too. Was the deadline explicit? Did you change priorities without acknowledging the trade-off? Feedback becomes fairer when you distinguish a performance gap from an unclear agreement.

If you cannot describe the concern without labeling the person, spend a few more minutes clarifying it before you speak.

2. Choose a Private Setting and a Clear Opening

Give feedback reasonably close to the event, once you have checked the facts and can speak calmly. Avoid public criticism, surprise confrontations between meetings, or saving several unrelated frustrations for one conversation.

You do not need an elaborate introduction. A possible opening is:

“I’d like to talk about the timing of our project updates. My aim is to understand what’s getting in the way and agree on how we handle them going forward.”

Then explain the observation and impact:

“The last two updates came after Tuesday’s deadline. That meant we entered the planning meeting without current delivery information.”

Be warm, but do not hide the concern inside so much reassurance that the message disappears. Genuine appreciation matters; it does not need to serve as packaging for criticism.

3. Ask for Their Perspective Before Solving It

After describing the issue, pause and ask:

“How do you see it?” or “What was happening from your side?”

Listen for information that could change your understanding: competing instructions, missing resources, skill gaps, or an expectation you thought was clear but never explicitly agreed on.

Listening does not mean withdrawing the feedback. It means testing your interpretation before deciding what should change.

If the person disagrees, return to the specific example rather than debating their character. If your facts are wrong, correct them. If priorities were unclear, acknowledge your part and clarify the expectation now.

4. Agree on a Next Step You Can Both Recognize

“Communicate better” is not an actionable agreement. Define what improvement looks like in everyday work.

For example:

“Going forward, please post the update by noon Tuesday. If that deadline is at risk, flag it Monday with a proposed alternative. What support would make that workable?”

Confirm:

• What the employee will do differently.
• What support or clarification you will provide.
• When you will review progress.

Ask them to describe the agreement in their own words—not as a test, but to catch different interpretations. Send a brief recap when useful, especially for recurring concerns. Serious or repeated performance issues may also require your organization’s formal process and HR guidance.

5. Make Room for Discomfort Without Retreating

Someone may be disappointed, defensive, or quiet. That reaction does not automatically mean you handled the conversation badly.

You can acknowledge the discomfort while staying clear: “I can see this is frustrating. I want to understand your perspective, and we still need to resolve the missed updates.”

Avoid demanding immediate agreement. If emotions rise, take a short break and set a specific time to resume.

Afterward, follow through on your commitments, recognize genuine progress, and keep interacting normally. Trust grows through consistent treatment—not one perfectly worded conversation. Your next step is simple: choose one concern, prepare the facts, and schedule a private conversation rather than waiting to feel completely comfortable.

For a practical way to prepare, explore Jessica Hill Holm’s workbook, Feedback That Builds Trust, which helps leaders deliver honest, constructive feedback that strengthens trust, improves performance, and builds accountability without damaging relationships. If you would like personal support with a conversation you are avoiding, consider a coaching call with Jessica.