How to bring up our self-assessment to your boss (without making it awkward)

I get it. You know of our tools like the “Am I a toxic boss?! self-assessment ” “How can EU bosses do better? report and conversation starters.

But you're like, “How am I even going to bring this up to my boss? I can't do it. This is too much.”

It can be intimidating, particularly in a stressful review meeting. I hear you.

But the self-assessment tool exists for a reason.

It isn't a public confession of one’s toxic tendencies. We’re all not always perfect. We do need a check sometimes. The self-assessment provides a confidential, safe space for bosses (or aspiring ones) to reflect on their management style and find areas for improvement. It takes about 2-3 minutes to complete and is very relevant to our policymaking needs in Brussels.

500 people have already taken it, and from what I am hearing from people, it has offered a space for self-awareness without others knowing about it.

If you think your boss could benefit from this, here’s how to approach it politely and constructively:

1. Start on a positive note

Before diving into the suggestion, set a constructive tone by acknowledging the positive aspects of your boss’s management style or the team’s achievements. 

For instance:
"I really appreciate the effort you’ve put into helping us navigate this year. We’ve made great progress on [specific project], and your guidance has been key."

This shows respect and gratitude, making it easier to introduce constructive feedback.

2. Frame it as a mutual benefit

Present the self-assessment as a resource that benefits both your boss as a leader and their teams. For example:
"I recently came across a leadership self-assessment tool that I found helpful for reflecting on my own growth areas. It made me think about how useful it could be for all of us to gain insights and refine our practices. It’s a tool designed to be supportive, not critical."

This positions the tool as a shared opportunity for reflection, not a pointed critique.

3. Highlight its credibility and purpose

Explain that the self-assessment is a trusted resource gaining traction in Brussels. Mention that it offers a private, non-judgemental space for reflection.
"It’s become quite popular in Brussels as a way for leaders to evaluate their impact, and many leaders have found it eye-opening and empowering."

4. Offer support, not criticism

Make it clear that your suggestion comes from a place of support and seeing all of us be better bosses.
"I thought it might be a great starting point for conversations about leadership development and team dynamics. It’s helped me see what’s working well and identify areas where we can grow together."

This approach ensures your boss doesn’t feel targeted but instead sees your suggestion as part of a broader commitment to team improvement.

5. Make a gentle request

Politely ask if they’d consider trying it out. Frame it as part of a bigger picture of team and leadership development.
"Would you be open to exploring it? I think it could help us better understand how we can all be part of creating an environment where we can all deliver our best work."

By emphasising the shared benefits and framing your suggestion as part of a collaborative effort, you make it easier for your boss to see it not as a criticism but as a collective development.

Final thoughts

Reviews are tough, especially when you want to stand up for yourself and ask for a raise or promotion. But tools like the self-assessment are intended to get you to encourage or practice making your demands. And self-reflection is also part of their growth.

They’re not about criticism—they’re about seizing the chance to learn how to stand up for yourself and your needs.

Other resources

• Conversation Starters for end-of-year reviews, and

• Our “How EU bosses can do better! report, which provides practical steps toward creating a safe, seen, and supported work environment.

• ”Am I a toxic boss?! self-assessment

If you find these resources valuable, please share them with your peers or bosses.

I hope that such small gestures may initiate a larger shift in how we are led.