Building a relationship with my boss’s boss used to feel like trying to hug a cactus:
Prickly and awkward.
I pictured stiff formal emails and nerve-wracking meetings. All while wondering if my own boss would think I was plotting a corporate takeover.
It felt weird, risky, and downright uncomfortable. So I avoided it.
Until I realized my career growth was stalling because I wasn’t making those crucial connections.
Turns out, connecting with higher-ups doesn’t have to be so intimidating.
And you don’t need to schedule an “official meeting.”
I’ll show you how in this email.
The Problem
You know it’s crucial to build a relationship with your boss’s boss.
But the idea of scheduling an “official meeting” feels like too much right now.
The Big Small Thing
Start with these informal, low-pressure ways to connect:
1. Sit next to them in a meeting. Just sitting close can spark a conversation.
2. Ask a quick question in passing. A casual “Hey, do you have a minute to answer a quick question?” is a great place to start.
3. Speak up in meetings. If you never speak, they won’t know who you are! Make sure you’re not just the person who nods like a bobble-head.
4. Give a small holiday gift. I used to think gift-giving at work was a waste of time and money. Until I observed how that little box of chocolates from my financial advisors each holiday season legit made me feel closer to them. (Kids, paws off that milk-chocolate sea salt caramel!)
5. Reply to their emails or Slack. Engage with their weekly mass emails by responding with a comment or question. If they have a quick feedback survey/button, smash it and make them aware of your existence.
6. Pop into office hours. If they have office hours, take advantage of the opportunity to chat. Do this at least 2x/year at a big company, more often at a smaller one.
7. Give out some props. Tell them something great about your boss. Compliments go a long way, and it’s a win-win-win situation!
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How This Helps You Chase What You Want
These small actions help build rapport without the formality of “scheduling a meeting.”
You’re creating opportunities to be noticed and remembered.
Plus, by sharing great feedback about your boss, you’re seen as a positive and supportive team player—key traits of future leaders.
Building a relationship with your boss’s boss doesn’t have to be intimidating.
Start small with these easy strategies to stand out.
