Don’t Wait to Say It

When you step into a new working relationship, especially with a new boss, you’re not just learning how they operate. You’re quietly teaching them how to work with you.

And here’s the part most people miss:if you don’t do this intentionally, it still happens… just by default.

The early days of a relationship matter more than we think. Patterns form quickly, such as how work gets assigned, how decisions are made, how feedback is delivered, and how boundaries are respected (or not). Most people stay quiet during this phase. They don’t want to rock the boat. They tell themselves they’ll speak up later if something becomes a real issue.

But that silence? It becomes the blueprint.

I learned this lesson early in my career. I worked with a senior leader who had a habit of publicly criticizing people. Meetings, hallway conversations, it didn’t matter. If he was frustrated, everyone knew it. When I found out he was going to become my boss, I had a choice. I could stay quiet and hope it wouldn’t happen to me, or I could address it head-on.

I chose the harder path.

I sat down with him and told him that if he was disappointed in my work, I absolutely wanted the feedback, but I wanted it delivered privately. I asked him to give me the opportunity to address it before it became public.

It wasn’t an easy conversation, but it was a defining one.

And it changed everything.

That conversation didn’t damage the relationship; it strengthened it. He respected the clarity, and I demonstrated that I wasn’t going to avoid difficult conversations. More importantly, it built trust early. It also opened the door for ongoing, honest conversations about prioritization, workload, and decision-making. Because once you establish that kind of transparency, it becomes part of how you work together.

These conversations take courage, especially when your boss is overloading you, stepping into your responsibilities, or making decisions you feel you should own. It’s easy to rationalize staying quiet by telling yourself they’re new, or now isn’t the right time, or it’s not worth addressing yet.

But waiting rarely fixes the pattern. It reinforces it.

The goal isn’t to confront – it’s to align. The most effective approach is grounded in curiosity. Assume positive intent. Your boss may not realize the impact of their actions. They may be trying to protect you from something you don’t see. Or they may have questions about your readiness that haven’t been voiced yet. When you approach the conversation with openness rather than defensiveness, you create space for a real dialogue.

And even if the conversation is uncomfortable, you gain clarity. You learn how they see you, what they expect, and where you stand. That information is far more valuable than guessing.

Every interaction is shaping the relationship. Every time you stay silent, you reinforce a pattern. Every time you speak up thoughtfully, you have the opportunity to redefine it.

So, the question isn’t, “Should I say something?”

It’s, “What am I teaching them if I don’t?”

“T.E.A.C.H.” Them How to Work With You

If you’re not sure how to approach these conversations, here’s a simple way to think about it:

T: Timing Matters
Address patterns early, before frustration builds. Choose a calm moment rather than reacting in the heat of the issue.

E: Express the Impact
Share what you’re noticing and why it matters. Focus on outcomes, not blame.

A: Assume Positive Intent
Lead with curiosity. Ask questions and seek to understand before jumping to conclusions.

C: Clarify Expectations
Get specific about roles, responsibilities, and decision-making authority to prevent future misalignment.

H: Hold the Line (Respectfully)
Be clear about what you need to be successful and reinforce it consistently over time.

You don’t have to control the relationship, but you do have the power to shape it, one courageous conversation at a time.