Use these 5 proactive strategies when emailing your senior leaders

Picture this:

Your heart’s racing and palms are sweaty.

You’re hovering over the “send” button on an email to a senior leader at your company.

You know connecting with them could boost your career, but you’re unsure of the “rules of engagement.”

What if you say the wrong thing and land on their “Who’s this?” list?

What if it’s not the norm to email your skip-level?

What if they don’t respond and then you lose sleep, worried you made the wrong call to email them?

Reaching out to higher-ups is intimidating, but here’s the thing:

There are 5 smart strategies you can use when reaching out to senior leaders.

I’m breaking them down for you in this email.

The Problem

Meeting with senior leaders is one of the most powerful ways to advance your career, but most people shy away from it because the nerves kick in.

The fear of saying the wrong thing or making a misstep feels too risky.

But avoiding it has a price: It can seriously stall your career and keep you from advancing at your company.

The Big Small Thing

Here’s how to confidently reach out to a senior leader and leave a great impression:

1. Ask about office hours: Shoot them a quick ping, “Hi X! Do you hold office hours?” If they do, great. If not, you might prompt them to say, “I don’t, but I probably should!” This could lead to a meeting slot anyway.

2. Keep your email short: Precede your meeting with an email that includes what you want to cover. And get to the point quickly in that email. Senior leaders don’t have time for long emails. Keep it to 3 bullets max and under 150 words.

3. Be clear about your request: Want advice, more responsibility, clarity on a team goal, or a promotion? Be specific about what you want. However, note, if it’s a promotion, frame it as a “career development conversation.”

4. Get your manager’s buy-in: Have your manager review your draft email. This gets their support and allows them to make edits based on what they know about the senior leader.

Remember, people need to weigh in to buy in. If they feel participated in the email, they’ll feel invested in the outcome. (i.e. they might say in their next 1:1 with their boss, “How’d the meeting with [X] go? Aren’t they great?”)

5. Respect their time: Use the “seniority/time inversion” rule: the more senior someone is, the less time you ask of them.

Here’s a guideline:

• Boss: 30 min
• Boss’s boss: 20 min
• Boss’s boss’s boss: 15 min
• Boss’s boss’s boss’s boss: 10 min

Pro tip: If you ask for 10 minutes, it’s likely going to be 15 anyway. (It’s not practical for an admin to block something for 10 minutes.)

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How This Helps You Chase What You Want

Connecting with senior leaders opens doors, and it positions you as a proactive professional.

Use these 5 strategies to make a strong impression, get noticed, and create new opportunities for career growth.