The Executive's Claude Guide
How to Use Claude: A Practical Guide for Busy Executives
How to use Claude AI, in one sentence: open claude.ai, paste your context, describe what you need in plain English, and refine the draft it gives back. This guide expands that sentence into a practice—what Claude is, how to get your first useful answer in ten minutes, and the five workflows, with exact prompts, I teach every client first.
1-on-1 with Pete Enestrom, on your actual work
Written by Pete Enestrom
Yale & Columbia, ex-Microsoft & Intel — 1-on-1 AI coaching for executives
Your coach’s background
Claude is an AI assistant made by Anthropic. If you've never used one, here's the honest one-liner: it's a very fast, very well-read colleague who lives in a chat window. You describe what you need in plain English—a summary, a draft, a second opinion—and it writes back in seconds. There's nothing to install, nothing to code, and nothing to be embarrassed about not knowing.
People ask why I start most executives on Claude rather than the other tools. Two reasons. It's unusually good with long documents—it will actually read the 80-page board pack you paste in—and its writing is measured and plain, which is what business communication demands. ChatGPT, Gemini, and the rest are fine tools. But for the work executives do all day, Claude is where I begin.
This is the guide I wish someone had handed me four and a half years ago. It's the same material I cover in the first hour with a new coaching client, written down. If you're wondering how to use Claude AI in a real business—not demos, not party tricks—this is the shortest path I know.
Getting started: five steps to your first useful answer
Everything below works on the free plan at claude.ai. Here's how to use Claude from a standing start—the same sequence I walk clients through in week one.
Open an account at claude.ai
Sign up with your work email. The free plan is genuinely enough to learn on. Move to the paid plan only when you hit the usage limits or want more room for long documents—by then you'll know exactly why you're paying.
Bring one real task from this week
Don't ask it trivia to “test” it. Open your to-do list and pick something you actually owe someone: a summary you keep putting off, a difficult email, a document you've been avoiding. Real stakes produce real learning.
Brief it like you'd brief a person
The single biggest unlock. Before the ask, give Claude the same context you'd give a new hire: who you are, who this is for, and what a good result looks like. Then paste the source material—the email thread, the draft, the notes. Context in, quality out.
Treat the first answer as a first draft
The first response is the start of the conversation, not the end. Push back: “shorter,” “less formal,” “the second paragraph is wrong—here's why.” The third version is usually where the value is, and getting there takes two minutes, not two days.
Keep the prompts that work
When something produces a great result, save the exact prompt in a note. Within a month you'll have a personal playbook—your board-prep prompt, your email prompt, your meeting-notes prompt—and each one gets better every time you reuse it.
Five workflows I teach first
These are the five uses that land with every founder and executive I coach. Copy the prompts verbatim, replace the brackets with your material, and adjust the last line to taste. The prompt is the easy part—your context is what makes the output worth reading.
I'm preparing for our quarterly board meeting. Below is last quarter's board deck and this quarter's draft numbers. [paste] Write a one-page pre-read for board members: the three numbers that moved the most, why they moved, and the two decisions I need the board to weigh in on. Plain language, no jargon, under 400 words.
Paste the actual documents. Claude reads all of it—the deck, the spreadsheet export, the appendix—and the summary gets dramatically better.
A long-time customer just emailed us, upset about a price increase. Their email: [paste]. Draft a reply that acknowledges the frustration directly, explains the increase in one honest sentence, and offers a call this week. Under 150 words. Warm and direct—no corporate speak, no “we value your business.”
The closing instruction—“warm and direct, no corporate speak”—is what separates this from the email you'd delete.
Here are my raw notes from today's leadership meeting: [paste]. Turn them into three lists: decisions we made and who owns each one, questions we raised but didn't resolve, and anything I personally said I'd follow up on. Bullet points, no filler, no commentary.
Run this the same afternoon, while you can still correct it. By Friday the notes are an archive; today they're a management tool.
I run [one line about your company]. A competitor, [name], just announced [what they announced]. Their announcement: [paste]. Explain what they're likely trying to accomplish, which of our customers would care most, and three questions I should put to my team on Monday. If you don't know something, say so instead of guessing.
That final sentence matters. It gives Claude permission to say “I don't know”—which is what makes its answers trustworthy.
I want to document how we onboard a new client; right now it only exists in my head. Here's my messy description: [describe it]. Before writing anything, ask me up to five questions about steps I might have skipped. Then turn it into a numbered SOP a new operations hire could follow, ending with a checklist.
“Ask me questions first” is the highest-leverage sentence in this entire guide. Steal it for every prompt you write.
Claude vs. ChatGPT: an honest note
I use both, and I tell clients the same thing I tell friends: the honest differences are smaller than the internet wants you to believe. Claude is where I go for long documents and careful writing—it reads more at once and pushes back less about tone. ChatGPT is a strong generalist with a larger ecosystem of extras around it. If a colleague swears by one, that's fine. The skill transfers almost completely.
What doesn't work is splitting your attention across four tools and going shallow on all of them. Pick one, use it daily for a month on real work, and only then form an opinion. Everything in this guide applies to whichever you choose.
The mistakes I see smart people make
After coaching many executives through exactly this, the failure modes are remarkably consistent. None of them are about intelligence—they're habits, and they're all fixable in a week.
- Asking questions instead of assigning jobs. Claude is strongest when you hand it a task with materials, not when you treat it like a search box.
- One-line prompts. “Summarize this” gets a generic summary. Who it's for and what you'll do with it—that's the brief.
- Accepting the first draft. The edit conversation is where the quality lives; skipping it is like hiring someone brilliant and never giving them feedback.
- Pasting confidential material without a policy. Treat anything you paste as shared with an outside vendor. Get your company's rules straight first—there's more on this in the FAQ below.
- Using it for last week's news. Claude has a knowledge cutoff and doesn't browse the live web on every plan. For anything time-sensitive, paste the source or verify elsewhere.
When teaching yourself stops working
Everything above, you can do this week, alone, for free. A lot of people should stop there for a while—self-teaching absolutely gets you fluent. But there's a ceiling I've watched many executives hit around month two: the generic workflows are running, and the question becomes which of your workflows—the board process, the sales follow-up, the way your firm actually writes—should be rebuilt around these tools, and in what order.
That's the point where a human teacher—not an AI coach bot, not another course—earns its keep. In a 1-on-1 session we open your real workload, find the hours these tools can genuinely hand back to you, and build the prompts and habits around your business, your voice, and your risk tolerance. This guide is the map. Coaching is walking it together on your terrain.
1-on-1 coaching
Want a teacher, not another tutorial?
Guides get you started. A 1-on-1 session gets you fluent—built on your actual work, at your pace.
Your coach
Coached by Pete Enestrom
Yale and Columbia grad, former Microsoft and Intel, and a venture-backed exited founder. Pete has spent the last four and a half years going deep on every major AI tool, and he teaches the way operators learn: on your real work, at your pace, with nothing assumed.
Common questions
Straight answers, the way I'd give them across a table.
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