scared to email your boss’s boss? read this
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Hi Reader, That’s how long it took me to feel comfortable meeting with my boss’s boss regularly at Google. Because let’s face it: It’s intimidating as heck. 😳 I always thought… a) They’re so busy — they’d never have time for me b) My impostor syndrome would be on full display c) I don’t know what to talk to them about, and anything I do share would have to be perfect 👉 The Problem This poll shows over a third of people never meet regularly with their boss’s boss. Wowza. That's a lot. 👉 The Big Small Thing It’s time to schedule a meeting with your boss’s boss. Because your boss’s boss plays a major role in your career trajectory. 👀 Um, Jenny? Going above my boss’s head for a meeting? No thanks, I’d rather be chased by a swarm of bees! I get it. Respecting the chain of command used to be the norm. But in modern organizations, developing a relationship with your boss’s boss is encouraged. Just give your boss a heads-up before you reach out. (Note: If you’re already well-acquainted with your boss’s boss, apply the following to the next rung above them.)
✅ Here’s how to schedule a meeting with your boss’s boss: Pro tip: To arrange a meeting, lead with praise. Boost your chances of a yes by starting with a genuine compliment. Here’s an email example you can use: “Hi [Boss’s Boss Name], Hope you’re doing well and that you survived the heatwave this weekend! I appreciated your recent team update. The way you explained the thought process behind the new changes was so helpful. It gave me a much better understanding of our direction as a company, and I appreciated your openness. I noticed that [insert project] is a key focus this quarter. I’m eager to discuss how I can contribute. I also have some achievements from [related project] that I’d love to share. Could we schedule 15 minutes to chat? I’ll coordinate with your assistant.” 👉 How This Helps You Chase What You Want Does sending this email scare the heck out of you? It probably should. I still get nervous before emailing powerful people, and that’s okay. Here's the thing: You can offer value to your boss’s boss regardless of your experience level. New to the company? Share fresh perspectives on hiring and onboarding. Been around longer? Provide unique insights, customers, and active projects. These ground-level perspectives are incredibly valuable. You’d be shocked to know how little your leaders sometimes know about what's happening on the ground day-to-day. They WANT to learn this stuff from you. Plus, when you reach out and build these connections, you strip away the mystique surrounding the higher-ups and position yourself as a bold, proactive go-getter. Let’s do this, P.S. I’m curious. What is the norm around meeting with higher-ups at your company? Hit “reply” and let me know. |
