One-on-one AI coaching built around your own work

Show me the tasks that eat up your week. In four sessions, we’ll build tools to handle them, and you’ll learn how to build the next ones yourself.

Book a free 30-minute call with Steve

Here’s what happens on the call

Steve Silverman

AI coaching is for you if

  • You’ve dabbled with AI and know you’re barely scratching the surface.
  • You’re expected to be your team’s go-to AI person, but you’re learning it on your own.
  • You run your own business, but scheduling, follow-ups, and admin eat up time you’d rather spend with clients.
  • There’s a new AI thing every week, and you need someone to show you what’s worth your time.

Your progression in four sessions

Four 75-minute Zoom sessions over six to eight weeks, built around your work.

  1. Session 1:

    Connect AI to your work

    First, we’ll securely set up Claude or ChatGPT, switch on its memory, and connect it to your email, calendar, and files. By the end, it can find that one email you thought you lost.

  2. Session 2:

    Delegate your busywork

    Next, we’ll take the repetitive tasks you named on your free call, like booking meetings or writing weekly reports, and practice handing them to AI while keeping you in the loop.

  3. Session 3:

    Point AI at your biggest goal

    Now we’ll tackle that project you thought was too big, like a personal agent that keeps hundreds of clients or donors feeling special. You’ll see the payoff in your real work.

  4. Session 4:

    You take it from here

    We polish what we built, and you learn to teach your AI new tricks just by describing what you need. By now, you’re ready to share your know-how with colleagues and clients.

Beyond our four sessions, you get

  • A fifth session at no extra cost if we need it to reach your goal
  • Ready-to-use prompts and tools I build for you between sessions
  • A privacy and security check of your AI setup
  • A recap after each session with your top three action items
  • The setup, agents, and apps we create are yours to keep

What it’s done for people as busy as you

1 click

replaces an hour of formatting research tables

“Your tool would have saved me 5 hours a week, at least.”

See how we built it
Liz BakerLiz BakerProfessor, University of Alabama at Birmingham

$25,000 saved

by using Claude to replace unreliable contractors

“Oh, that’s going on my yearly review!”

Read her story
IT DirectorDC-based privacy nonprofit

5 meetings

booked the same day as his first session

“I’ve used Claude to schedule five meetings today. Game changer.”

Kris L.Fundraising Professional

The coaching package

Four 75-minute sessions, plus a fifth if we need it, and everything listed above

$2,400

or two payments of $1,200

Book a free 30-minute call with Steve

Want this for your whole team? Let’s talk.

Frequently asked questions

How is my work kept private?

Privacy is built into how I work. Your work stays between us, and I never share it without your explicit OK. For example, I always get clients’ approval before publishing their stories on this website.

When we set up your AI, we’ll turn off settings that let the company learn from your chats. To protect your privacy and security, we’ll turn on two-step sign-in for any accounts it connects to. Also, if your work involves other people’s information, such as clients, members, or customers, we’ll set up your AI to keep each person’s details separate.

Read my full privacy policy

Do I need to be technical?

No way. All you need is curiosity and a willingness to try new things. The main skill is describing what you want by typing or dictating. I’ll handle the technical setup with you in session 1. From there, you’ll mostly just talk to your AI.

Which AI do I need?

I teach Claude and ChatGPT, the two leading AI assistants. You’ll need a paid personal plan for one of them, starting at $20 a month. If you don’t have one yet, I’ll help you choose the one that works best for you.

Can I use the AI my work already provides?

It depends. If your work account gives you Claude or ChatGPT with the main features turned on, including connections to your email, calendar, and files, that works. If your work plan blocks any of those, or if you use Microsoft 365 Copilot or Google Gemini, I’ll ask you to get a paid personal plan with Claude or ChatGPT. That way, nothing holds back what we build.

What if we don’t finish in four sessions?

Then we take a fifth session at no extra cost to finish the same goal. You’re paying to finish what we build, not for a count of sessions.

How do payments work?

The package is $2,400. You can pay in full up front, or in two payments of $1,200: one to start and one before session 3. I take Zelle, and I can send a credit card invoice if you prefer. If your organization is paying, I can bill it directly.

What if I need to reschedule?

No problem. Please give me at least 24 hours’ notice, and we’ll find a new time. Emergencies happen, so your first late change is on me. After that, I’ll count a cancellation with less than 24 hours’ notice as one of your four sessions.

Still deciding? Let’s talk it through.

On a free 30-minute call, you’ll do most of the talking. Here’s what I’ll ask:

  1. How are you using AI in your work right now?
  2. What repetitive computer work do you want to hand off?
  3. What would you build if you had the time and skills?
Book a free 30-minute call with Steve