Session 2  ·  AI Chief of Staff Cohort 1

Give Your COS
a Voice

This session your COS gets a phone number. It screens calls, handles inbound, and books meetings – without you.

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Russ Perry
Before We Build Anything
The tools don't matter.
The outcome does.
  • Tools change. Bland today, something else in 6 months. That's fine.
  • Technical paralysis is real. Don't let "which tool is best" stop you from building anything.
  • Hype is louder than signal right now. Ignore 90% of it.
  • The question is never "which AI phone tool should I use?" – it's "what should my COS own on the phone?"
Let Your COS Guide the Build

Tell your COS the outcome you want. Push back on requirements. Ask it to simplify. It will tell you what you actually need.

When someone asks "X vs Y"

Ask yourself: does it accomplish the outcome? Is it the simplest path? If yes – build it. You can swap the tool later.

Infrastructure Tip
Tailscale – Access Your COS Anywhere

Your COS runs on your machine. Tailscale gives you a private, encrypted tunnel back to it – from your phone, a hotel room, anywhere.

  • Access your files and system remotely without exposing anything to the public internet
  • Share screen or control your Mac from anywhere once it's set up
  • Essential once you start building automations that run 24/7
  • Free for personal use, works across Mac, iPhone, Windows
Setup Order
  1. 1. Install Tailscale on your Mac
  2. 2. Install on your iPhone
  3. 3. Sign in with the same account on both
  4. 4. Enable SSH on your Mac (System Settings → General → Sharing)
⚠ Permissions Disclaimer

Once Tailscale is installed, you must grant Full Disk Access and Screen Recording permissions in System Settings → Privacy & Security – otherwise remote access to files and screen share will not work.

Quick Recap
Last Week's Homework

You were asked to write down 3 things you want your COS to handle that you currently handle yourself.

Who brought their list?

We're building those this session.

Session Outcomes
By The End of This Session You Will Have:
  • ✓ A dedicated phone number for your COS (via Bland.ai)
  • ✓ An inbound call handler – screens callers, collects info, routes appropriately
  • ✓ Basic outbound scripting so your COS can call on your behalf
  • ✓ Live tested it – called your own COS number and it worked
This Session
Agenda
  • Part 1
    How AI Voice Works30 min  ·  What's happening under the hood and what your COS should own
  • Part 2
    Bland.ai Setup + Phone Number20 min  ·  Live number in your hands
  • Part 3
    Build the Inbound Handler25 min  ·  Screening logic, calendar link, escalation path
  • Part 4
    Live Test15 min  ·  Everyone calls their own COS number
  • Part 5
    Outbound Script + Open Support30 min  ·  Stretch goal + questions, wins, troubleshooting
Part 1

How AI Voice
Works

What's happening under the hood – and what your COS should own vs. escalate

The Problem
The Phone is
Still Broken
  • Most calls are low-value interruptions
  • You answer anyway – because what if it's important?
  • Voicemail is dead. Nobody leaves them. Nobody checks them.
  • Scheduling a call is a 6-email thread waiting to happen

Your COS should
own the phone.

Bland.ai Capabilities
What Your COS Can Do On the Phone
Screen Inbound Calls

Know who's calling and why before you ever pick up

Book Meetings

Check your calendar and offer times on the spot – no back and forth

Make Outbound Calls

Follow up, confirm, request info – in your voice, on your behalf

Take Intelligent Messages

Not just voicemail – structured data you can search and act on

Decision Framework
What Your COS Owns vs. What It Escalates
COS Owns
  • Cold or unknown callers
  • Scheduling requests
  • Status updates ("is X done?")
  • Vendor follow-ups
  • Intake and triage
Escalate to You
  • Existing clients with urgent issues
  • Anyone you've flagged as VIP
  • Emotional or sensitive conversations
  • Decisions only you can make
Part 2

Bland.ai Setup +
Your Phone Number

You'll have a live number in the next 20 minutes

Live Setup
4 Steps to Your Number
  1. 1Create your Bland.ai account at bland.ai
  2. 2Add a payment method  ·  usage-based, ~$0.09/min
  3. 3Purchase a phone number  ·  $1.15/month
  4. 4Create your first Pathway – we'll do this live together
Open bland.ai now ↗
Part 3

Build the Inbound
Handler

Screening logic, calendar link, escalation path – built live

The Flow
What Happens When Someone Calls
Call
Comes In
→
COS
Answers
→
Collects Name
+ Reason
→
Priority
Caller?
→
YES → Notify Russ via SMS
NO → Take message / Book meeting

We're building this pathway live right now.

Pathway Building Blocks
The 4 Nodes You Need
Greeting

"Hi, you've reached [Name]'s office. This is their AI assistant..."

Question

Collect caller name, company, and reason for calling

Decision

Route based on: VIP list, urgency keywords, time of day

Handoff

Send SMS / book calendar slot / take structured message

Part 4

Live Test

Call your own number right now.

We fix it live if it breaks. That's the point.

Part 5 – Stretch Goal

Outbound: Your COS
Makes the Call

If we have time – and we'll try

Outbound
Where Outbound Pays Off Immediately
  • Appointment reminders – no-show rate drops ~40%
  • Lead follow-up – "You filled out our form – can I get you 15 min with Russ?"
  • Client check-ins – "How's everything going with the project?"
  • Vendor coordination – "Confirming delivery for Thursday"
  • Reference calls – "Quick 5-min call to verify before we move forward?"
Before Session 3
Homework

One task: Use your COS phone number for one real interaction before Session 3.

Screen a call, book a meeting, or make an outbound call. Come ready to share what happened – what worked, what didn't.

Session 3: The Intelligence Layer

Open Floor
Questions. Wins. Stuck?

Ask Anything

Drop questions in the chat or unmute now. No such thing as a dumb question here.

Share a Win

Session 1 breakthrough? Something your COS did this week that surprised you? We want to hear it.

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