Delivering Uncomfortable Messages: Six Guiding Questions

Whether you are a supervisor, project manager, team leader, executive team member, or even the president, delivering uncomfortable messages is simply part of your job.

Consider these examples:

• A leadership team meets to review an important project shepherded by one member. In response to questions, that member comes across as defensive and resentful. You are the head of that team. Do you bring his defensiveness to his attention. If not, why not? If so, how? When?

• You’re in a tough negotiation with a key performer about working in the office vs. remotely. She’s dug in, with a “take it or leave it” mindset. Do you talk about the issue, or about her mindset? What do you say, and when? Or do you cave in and avoid, because…?

• In a situation where a work colleague has bad breath or body odor, do you say something about it? How do you deliver a message like that?

All of these situations offer an opportunity to deliver meaningful, yet potentially unsettling messages. Typically, a leader wants to find a way to deliver that feedback. They often have the will, but not the skill.

Here are six questions to ask yourself before you deliver unsolicited, uncomfortable feedback:

1. Is it wanted?

Sharing unflattering feedback is a risky move that can produce high value.

You can reduce the risk, before jumping in, by asking: “Are you open to some feedback?” Or, “I want to share with you something I’m noticing, that’s sensitive and personal. Are you open to hearing that?”

Pushing unrequested feedback on someone who is resistant may only exacerbate the problem and worsen the relationship. It probably won’t end well for either of you.

If the person shows no interest, be ready to accept that.

Exception: If the resistant individual is a direct report, you might want to explore what their resistance is all about. Dodging feedback would likely be costly to their performance or reputation.

2. Does it serve?

Feedback should serve the other person, not satisfy your need to vent. Before delivering an uncomfortable message, you should be able to clearly see how it would be helpful to the other.

Ask yourself: “Will this help them see something they don’t already see?”

Stay behavior-focused—avoid labeling intent, diagnosing personality, or assuming motives.

3. Is this the time and place?

Consider carefully what setting and timing is appropriate to the message you want to deliver.

In some situations, an immediate response is necessary. For example, I once sat in on a leadership team meeting wherein one of the members whispered a derogatory remark about gay people. The CEO spoke up immediately, saying, “I want everyone in this room to know that the comment you just heard is unacceptable in this company and in the culture I want to build here.” After a few moments of stunned silence, the man apologized, and the meeting continued.

Other situations call for more restraint, a less task-oriented time, or a cooling off period.

The important thing is to decide, not to react.

4. Do you own it?

Take full ownership of your message, without a hint of blame or accusation. Start your delivery with the pronoun, “I,” to make it clear that you are speaking only for yourself.

Resist ducking personal ownership of your message by relying on “We” or People.” Instead, try:

• “I’ve noticed”

• “I’ve observed”

• “I’ve wondered”

Avoid accusatory and exaggerated language that invites defensiveness:

• “You always…”

• “You never…”

5. Is it framed as a perception, or as a fact?

Your feedback is a perspective, not a verdict. It’s important to acknowledge to yourself that what you are observing and saying might be biased, limited, or off-base. Use language reflective of that humility:

• “I could be wrong about this…”

• “This is just my own way of seeing it…”

• “Maybe there’s something I’m missing here…”

6. Are you prepared with specific examples?

A rule of thumb: Instead of telling people what they’re doing, share your specific observations and give time and place examples:

• NO:  "You need to be a better listener.”

• YES:  “In last week’s meeting, I noticed you interrupted three times while others were mid-sentence.”

If you can’t give two or three specific examples, you’re not ready to give useful feedback.