Ever wanted to connect with someone who feels completely out of your league — a CEO, a senior leader, someone well-known in your field? This week's Mentor's Corner covers how to actually do it.
This is Coached Weekly, my career notes where I share the tiny % of ideas that actually work in real careers. It takes 5 minutes to read, but could speed up your career by years. I write this myself (no AI) and I read your replies. —Rohan Mahtani (LinkedIn)
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The 20-second Career tactic
I've coached people for a decade. Here's one idea that moves the needle. I teach it in 20 seconds.
How to say "I don't know" without looking bad
If you're put on the spot in meetings, it's natural to feel like you have to guess or fake an answer. But guessing usually makes you look worse. I've found it better just to confidently say something like:
"I don't have that info right now, but I'll follow up with meeting notes afterward."
Or, "I'm not 100% sure and don't want to give you incorrect info — can I double-check and email you?"
Or even, "That's a great question — it's not quite my area, but let me connect you with Sarah, who would know better."
People love and respect this clarity + initiative.
Heads up:
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It’ll speed up your job search (or your friend’s).
Mentor's Corner
Insights put together by me. One practical lesson a week that will make a measurable impact on your career, delivered right to you — for $0.
How to reach and connect w/ people way out of your league
I'm generally not a fan of trying to network with famous people.
Why? Because how much time does an Elon Musk or Jeff Bezos really have to give you career advice? Two, they're almost impossible to reach.
But note: I didn't say impossible. I said almost impossible.
I've written a lot about networking, and I genuinely believe you get the most value from connecting with people one or two steps ahead of you — they're accessible, they remember what it's like to be where you are, and they give practical advice.
But sometimes you want to reach someone who feels completely out of your league. A CEO, a senior leader at a company you admire, someone well-known in your field. And the normal rules don't apply — these people are bombarded with requests.
If you need to connect with someone like this, here's how I'd go about it.
🐴 Send something outrageously personal
Famous and powerful people are bombarded with attention and requests. If your outreach looks identical to the hundreds of others they receive, it's game over.
So err on the side of craziness, not caution. For example:
A woman once sent Queen Elizabeth a homemade calendar of a rare horse breed they both owned. She got an invite to Buckingham Palace.
A writer called Doberman Dan wanted to work with legendary copywriter Gary Halbert — but so did everyone.
So Dan sends him a fake newspaper with the headline "GARY HALBERT EARNS MILLIONS WITH OHIO WRITER", stuffed with jokes about their small town. Gary calls him. They end up working together.
The takeaway: outrageously personal outreach — something that could only have been sent to one person in the world — is your surest bet.
👤 Befriend the right-hand man
Let's say I was a tailor, and wanted to meet LeBron James.
I wouldn't try to meet LeBron. I'd try to befriend his manager, Rich Paul (or even his social media manager / video editor).
Rich has 1/10,000th the fame (and gets 1/10,000th of the inquiries) but has all the access. If I make Rich an insanely sharp suit, and he wears it meeting LeBron, LeBron might ask: "Where'd you get the suit?"
Boom. I'm in.
This applies beyond celebrities. Want to reach a CEO? Their chief of staff or EA probably has more influence over their calendar than anyone.
Want to connect with a senior partner at a firm? The associates who work under them are far more accessible and can make an introduction that actually lands.
📡 Find their open channel
Some people who seem impossible to reach are surprisingly accessible — just not where you'd expect.
Investor Bill Ackman is constantly on X, posting and actually engaging with replies. The CEO of Shopify, Tobi Lutke, works on open source libraries — you could connect with him by contributing to his GitHub where he’s really active. Some founders are active in niche Slack communities or Discord servers. Others reply to comments on their Substack or YouTube.
Most people default to email or LinkedIn DMs, where these people are drowning. But they often have another channel where the volume is a fraction and they're actually reading. Find that channel.
🔨 Build something, don't ask for something
The biggest mistake people make when reaching out to someone above their level: they ask for advice. "Can I pick your brain?" "Would love 15 minutes of your time."
Busy people get hundreds of these. They're exhausting because the entire burden falls on them — they have to generate something useful for a stranger.
What works is the opposite: show up with something you've already built or done. A prototype. An analysis. A piece of work that's relevant to what they care about. Now you're not asking them to give — you're giving them something to react to.
✉️ If you do cold email, keep it stupidly short
If you're going to email someone directly, brevity is everything. Under 150 words. Ideally under 100.
Auren Hoffman, now a CEO himself, cold emailed Steve Jobs and Steve Ballmer from his college computer lab at 3am. Both replied within hours. His advice: "Most CEOs personally read every well-formed email they get." The key words being "well-formed."
A high schooler sent a short email to Snapchat's CEO Evan Spiegel in 2014. And it worked:
I wrote more about writing strong emails here - worth a bookmark.
👑 Don't put them on a pedestal
One last thing. When you do reach someone, don't give them the ick. Don't over-apologise for taking their time. Don't open with "I know you're incredibly busy and I'm so sorry to bother you." Be direct, be normal, treat them like a person you respect.
But also — and I mean this — think about whether you even need to reach this person. The most useful people in your network are almost never the most famous ones. Someone two steps ahead of you in your field will usually give you better, more relevant advice than any celebrity CEO ever could.
Connect with people at the right level, not the highest level!
Hopefully that’s a piece of advice you haven’t heard before. If you enjoyed this:
Forward it to a friend, family member or colleague. It does truly make a difference.
If someone you know is on a job search, tell them to check out Resume Worded. It’ll make their job search a lot shorter.
Speak soon,
Rohan Mahtani
Founder at Coached & Resume Worded
Btw, I like reviews. They motivate me to keep the quality high. Like this one:
Thanks Mario!
You can leave one here. I’d appreciate it. Thank you so much.
🤭 In all unseriousness
A few laughs to keep you smiling until next week
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