Dear Naveen,

Your question on the subject reflects a common fear: that having a crucial conversation with a supervisor might come across as disrespectful or out of line. However, silence often does more harm than good. Avoiding the issue can lead to frustration, resentment, and disengagement—not just for you but potentially for your team as well.

The truth is, a respectful, candid conversation can strengthen trust and collaboration, even with someone in a position of authority. Here’s how you can approach this challenging situation thoughtfully and effectively.

Work on Yourself First

Before engaging in a conversation, reflect on your own role in the situation. For instance, you mentioned withholding information to prevent premature or inappropriate sharing. While understandable, this may contribute to a cycle of mistrust and miscommunication.

Ask yourself: Am I doing anything that might escalate the problem or reinforce my supervisor’s behavior? Recognizing your part doesn’t excuse theirs, but it helps you approach the conversation with greater self-awareness and balance.

Start with Good Intentions

Request a private meeting and set a constructive tone from the outset. Thank your supervisor for their time and express your desire to strengthen your working relationship. For example:

• “I appreciate you making time to talk. I wanted to discuss a concern because I value our collaboration and want to ensure we’re working as effectively as possible.”

Positioning the conversation as mutually beneficial demonstrates respect and aligns you both toward a shared goal.

Focus on the Most Pressing Issue

It’s tempting to list every concern—micromanagement, oversharing, and boundary issues—but tackling everything at once risks overwhelming the conversation. Instead, focus on the most critical issue first.

To decide, ask yourself:

• What’s having the biggest impact on my work or the team’s success?

• What do I want most for myself, my supervisor, and our working relationship?

For instance, if micromanagement is eroding trust, start there. Once progress is made, you can address other issues in future conversations.

Stick to the Facts

When raising your concern, describe specific behaviors without jumping to conclusions or assigning motives. For example:

• “On Monday, after assigning me a project, you checked in three times throughout the day asking for updates. I felt rushed and struggled to stay focused because I was anticipating more interruptions.”

This approach avoids blame and keeps the discussion grounded in observable actions.

Suggest Solutions

After sharing your concern, offer constructive alternatives. For example:

• “It would help me stay on track if we could check in on the project once every two days instead of several times a day. I could also send a daily email summarizing progress and next steps to keep you updated.”

By proposing a solution, you show initiative and demonstrate your willingness to collaborate. If necessary, brainstorm together to find a plan that works for both of you.

Clarify Next Steps and Show Gratitude

End the conversation by summarizing what you’ve agreed to do:

• “So, I’ll send you a daily progress report, and we’ll plan for check-ins every other day. Does that sound good?”

Express appreciation for their openness and time:

• “Thank you for being willing to talk through this with me. I’m confident this will help us work more effectively together.”

Why This Approach Works

This method respects your supervisor’s role by addressing concerns privately and constructively. It separates facts from assumptions, seeks mutual solutions, and emphasizes collaboration over confrontation.

Of course, there’s no guarantee your supervisor will respond as hoped. If they’re unwilling to engage or improve, you may still face disengagement and frustration. However, by taking these steps, you can confidently say you’ve done your part to address the issue thoughtfully and respectfully—and that’s all anyone can ask.

Best wishes,

Yogesh