Dear Professor
"I'm feeling unconfident and wanting reassurance from my boss. What should I say or do?"
A former student recently wrote to me with a common concern:
"I'm feeling overwhelmed at work. Everyone on my team is nice and patient, but I'm struggling with some of our recent projects and I’m in need of assurance that I'm bringing value to the team. I want to ask my boss for reassurance. Is that a good idea? What should I say?"
Dear Student,
First, the very premise of your message means you care. Frankly, it is a gift when we find ourselves feeling overwhelmed and in need of reassurance. That means we are working outside of our comfort zone and striving to make progress. That being said, there are three key "Don'ts" and three "Do's" when it comes to initiating an "Am I doing okay?" conversation with your boss. Let’s start with the traps to avoid and then pivot to the winning moves.
The Three Don'ts:
1. Don't lead with emotion.
Many people feel stressed or anxious about their performance and start the conversation with their raw emotions—stress, concern, or self-doubt. It is never a good idea to bring your agitated self to a meeting with your boss. Your boss is NOT your therapist. So, instead, lead with data: "Here's what I'm working on, here's what I’ve accomplished, and these are the roadblocks slowing me down." This approach demonstrates a proactive mindset and keeps the conversation constructive.
2. Don't ask for "reassurance."
As tempting as it is to ask, "Am I doing okay? Do you think I’m doing well?"—resist that urge. Instead, refine your question to seek direction on action plans: "I'm evaluating whether I should be putting more energy into X or Y. Here's how I currently see things. Does my view align with your vision for the team?" This positions you as a problem-solver rather than someone seeking validation.
3. Don't bring up other people in a negative way.
I know of a former student who complained to their boss about a colleague "not being a team player" and "being frustrating to work with." This never goes over well. Keep the focus on your efforts, your energy, and how you align with the team’s mission and goals.
The Three Do's:
1. Do come prepared with specifics.
Outline what you’ve been working on, key milestones, and areas where you see opportunities for growth. This shifts the conversation from an emotional plea to a results-driven discussion.
2. Do ask for guidance, not validation.
Frame your ask around where to focus next, not whether you’re "doing okay." A strong question might be: "Are there any areas where I should shift my focus to better contribute to the team’s goals?"
3. Do close the conversation with an action plan.
At the end of the conversation, summarize what you’ve discussed and confirm your next steps. "Thanks for this conversation—my key takeaways are X and Y, and I’ll focus on implementing them over the next few weeks." This signals accountability and proactive follow-through.
Final Takeaway:
Feeling uncertain about your value at work is natural, but the way you frame the conversation with your boss makes all the difference. Avoid emotional appeals, focus on results, and seek direction instead of reassurance. Your boss will see you as engaged, strategic, and solutions-oriented—exactly the qualities that make a valuable team member.
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