Reorg fatigue is real. Ask these 11 questions to quickly align with a new boss, protect your energy, and lead your team with confidence.

There was a stretch in my career where I had seven different bosses in eight years. Nearly one per year. And that was just at the top level of the organization.

To say it was draining is an understatement. I was fried!

Each time, I had to quickly understand the new leader’s expectations, adapt my style, and keep my team steady while everything around us shifted. My head was spinning, but my people were counting on me to make each transition feel seamless or at least less rocky.

Looking back, I realize I spent too much time guessing instead of asking. If I could do it all over again, I’d start each new relationship with a simple, powerful tool: a set of questions.

The Questions I Wish I Had Asked

Here’s the list I would put on the table right away with a new boss:

  • What’s your preferred communication channel?
  • Do you prefer scheduling consistent 1:1s?
  • Would you like me to continue to make decisions for my team and escalate when necessary?
  • What level of involvement do you want in my business strategy?
  • Are there reports you need—and at what frequency?
  • Do you have “protected hours” (evenings, weekends)? Here are mine.
  • What are your top three priorities right now, and how will you define success in my role?
  • Do you prefer to be involved early in decisions, or once I’ve narrowed recommendations?
  • How do you like to give and receive feedback?
  • Who are the critical stakeholders you expect me to stay in sync with?
  • What’s one way I can make your role easier?

On the surface, these seem straightforward. But they do more than gather information—they establish clarity, alignment, and trust from the start.

Awareness, Willingness, Energy

Here’s where the messy middle of leadership gets real: the answers you hear may not always match what you want to hear.

And that’s when these questions become more than logistics—they become a test of your willingness to adjust.

This is why I lean on my AWE framework:

  • Awareness: The questions create awareness of the new environment and expectations.
  • Willingness: If the answers bump into your non-negotiables, it’s your moment to explore whether you’re willing to flex—or if you need to hold firm.
  • Energy: Your willingness (or resistance) directly impacts your energy. And your energy shapes how you show up as a leader—for yourself and for your team.

You can’t control how often the org chart changes. But you can control how you show up, what you ask, and how you bridge the gaps for yourself and others.

That’s AWE in action.

A Reflection for You

If you’ve been through reorg whiplash (and let’s be honest—most of us have):

✨ What’s one question you’ll commit to asking the next time a new leader enters your world?

The messy middle of leadership isn’t about avoiding change—it’s about learning how to navigate it with clarity, courage, and AWE.

You Don’t Have to Go Through This Alone

Endless reorganizations aren’t just disorienting for you as a leader—they’re disorienting for everyone around you. And carrying that weight on your own can feel lonely.

Here’s the truth: you don’t have to navigate it by yourself.

This is the work I do every day—helping leaders find clarity, steady their teams, and reclaim their energy in the messy middle. If you’re going through reorg whiplash and want support, I’d love to talk.

💌 And for weekly inspiration on how to incorporate AWE and thrive in the messy middle, sign up for my newsletter.

Remember: You are the Most Worthwhile Project You Will Ever Work On!