Stanford Writing Masterclass: How to Write Emails People Actually Answer with Glenn Kramon
September 7, 2026
AI Summary
5 min readHow to Write Emails People Actually Answer
Glenn Kramon, who spent 37 years as an editor at the New York Times and now teaches Stanford Business School's most competitive writing class, has a blunt diagnosis for most business emails: they're indistinguishable from everyone else's. His class, called Winning Writing, has a waitlist that students fight to get off. The core problem, he says, is that people write the way they think they're supposed to write—and that instinct is almost always wrong.
The First Five Words Decide Everything
Kramon's most provocative rule is simple: never open an email with "Hope you are well." He asks his students to raise their hands if they do it, and at least half go up sheepishly. The problem is that this phrase has become invisible. "People just don't even notice it," he says. "You want them to say, 'Wow,' the minute they start reading."
The logic is brutally practical. Most people read emails on their phones, where they can see only five words at a time. Those five words are your only chance to earn their attention. "Make them smile or just get right to the point," Kramon says. If you absolutely must express warmth, put it at the end: "Cheers. All the best. Hope you're well. They all mean the same thing, but don't waste your time at the beginning."
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What you'll learn
- 1 (01:00) **"Hope you are well" is dead** - Glenn explains why the most common email opener is a waste of your first five words and how to replace it.
- 2 (06:00) **The cold email opening that works** - How to start a cold email without a warm introduction and still grab attention.
- 3 (10:00) **Why writing matters more in the age of AI** - Glenn explains why his Stanford class is more popular than ever, even with ChatGPT.
- 4 (13:45) **How to edit AI-generated writing** - The hosts share practical tips for making AI output sound human again.
- 5 (16:11) **The two qualities that make emails one in a million** - Glenn breaks down warmth and competence with concrete examples.
- 6 (21:52) **The Nardwuar method of email research** - How deep digging on a person makes your outreach undeniable.
- 7 (24:13) **The 12 rules for email, unpacked** - Glenn walks through his famous lecture rules, focusing on the most counterintuitive ones.
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Show Notes
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When was the last time you wrote an email that actually stood out? Glenn Kramon spent 37 years as an editor at The New York Times and now teaches Winning Writing, one of Stanford GSB’s most popular and competitive courses. In this episode, we talk with Glenn about the top writing strategies that can make your emails, pitches, and professional communication “one in a million” instead of “one of a million.”
Tune in for lessons on:
✅ Why you should never begin an email with “Hope you are well”
✅ The two big qualities that make your writing stand out
✅ How to write a cold email people actually respond to
✅ Glenn’s 12 essential rules for writing better emails (and cold emails)
✅ What to write when someone ignores your outreach
✅ The power of a thoughtful gratitude note
Whether you’re applying for a job, pitching an idea, reaching out to someone you admire, or just trying to communicate more effectively at work, this is your masterclass on winning writing.
Timestamps:
00:00: Cold Open
03:55: How to be one in a million not one of a million
05:10: Why you should never say “hope you are well” at top of an email
07:09: Personalizing the beginning of an email
09:10: Why Glenn’s class is so popular
11:40: How to avoid AI “slop”
14:30: What makes a great email from a mediocre one
14:57: How warmth and competence goes a long way
18:20: How to be targeted in your strategy for cold emails
22:22: Golden Rules for writing emails
25:02: Unpacking the “sh*t sandwich” approach
28:37: Start with what your audience doesn’t know, not what it does know
32:40: Golden Rules for writing cold emails
33:18: It’s not about you, it’s about them
36:15: How to create a connection with the recipient of your email
43:10: How to be persistent with your follow-ups
48:00: How to write a great gratitude letter
53:08: Closing thoughts
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