Strategy 2: Prepare

Get ready for a high-stakes interaction before it happens.

The episode: A routine checkup turns serious. Jill takes the boys in for their physicals, and the doctor finds something on Randy’s thyroid that needs more tests. Tim and Jill find themselves in a waiting room facing a conversation with a doctor that matters — and neither of them has prepared for it. Tim is confident and capable in his domain: fixing things that weren’t broken, optimizing equipment. His domain is not this room. He has no questions written down. He does not know what the tests mean. When the doctor uses clinical language, Tim nods along.

The conversation that mattered happened without preparation. The outcome was worse for it.

The lesson: Preparation is not about being smart enough to know what to ask. It is about doing the work before you’re in the room, while you still have time, before the stakes activate your stress response and your recall degrades. The billionaire class has always had someone prepare them for important meetings. That person wrote the question list, reviewed the documents, identified the three things that mattered most. Now you have one too.

My Man Jeeves: The conversation that matters arrives, as a rule, at the least convenient juncture — in the waiting room, at the salary review, on the contractor’s walkthrough — by which point the faculties required to conduct it with competence have, regrettably, already been spent on stress. The preparation that would have been useful a day earlier is, one finds, perfectly available a day earlier. The billionaire class has, for some centuries, retained someone to do it.

What Prepare is for: Any situation where you are about to interact with someone who has more information or authority than you, and the outcome matters.

The core spec pattern:

I have [appointment/meeting/conversation] with [person/institution]
on [date] about [topic].
My goal is [specific outcome].
I’m worried about [specific concern].
Please help me prepare a list of questions to ask and
key points to make sure I cover.

Preparation does not require expertise. It requires 10 minutes and a list. The doctor, the HR director, and the contractor all expect you to show up without one. The list is what changes the power dynamic in the room. Every example in this chapter follows the same pattern: tell your Agent what’s coming, answer its clarifying questions, and walk in with a list on your phone. That is the entire strategy.

In the Field Guide: H-2 (Doctor’s Appointments), Li-1 (Difficult Conversations), IRL-1 (Government Offices), IRL-2 (Customer Service), Tr-4 (Air Travel).

Example 1: Before an Oncology Appointment

The situation: your primary care doctor called about your blood work. Something is elevated. They’re referring you to an oncologist. The appointment is in 10 days. You don’t know what to ask, what the blood work means, or what the appointment will involve. You’re scared, and the fear is making it harder to think, not easier.

Your opening message:

My doctor is referring me to an oncologist because
something in my blood work is elevated. The appointment
is in 10 days. I’m scared and I don’t know what
questions to ask. Please help me prepare.

Here’s what I know:
- My LDH level was 280 (normal is under 225)
- My doctor said it could be many things, not just cancer
- The oncologist is at [Hospital Name]
- I have a high-deductible health plan through my employer

Give me the most conservative framing. I will verify
everything with the oncologist.

Your Agent’s clarifying questions:

I understand this is stressful. Let me help you walk
into that appointment prepared. A few questions first:

1. Did your doctor mention any specific conditions they’re
ruling out, or just the elevated LDH?
2. Did you have other blood work done at the same time
— CBC, CMP, anything else? If so, were those normal?
3. Have you had any symptoms — fatigue, weight loss,
night sweats, swollen lymph nodes, unexplained pain?
4. Is this your first time seeing a specialist for
something like this?
5. Will someone be coming with you to the appointment?
6. How do you best absorb information — do you want
everything written out, or a short list you can
have on your phone?

Your answers:

1. They said elevated LDH can mean a lot of things —
liver issues, infection, or something more serious.
They didn’t name anything specific.
2. Yes, CBC and CMP were both normal.
3. I’ve been more tired than usual, but I started a
new job recently so I assumed that was it.
4. Yes, first time.
5. My partner is coming with me.
6. A list on my phone would be perfect. I know I’m
going to freeze up in the room.

Your Agent prepares you:

Here’s your preparation kit. Save this to your phone.

What you probably have:
First — LDH is a nonspecific marker. It goes up with
liver problems, infections, muscle damage, anemia, and
yes, some cancers. But your CBC and CMP are normal,
which rules out several of the scarier possibilities.
An oncology referral does not mean cancer. It means
your doctor wants someone who specializes in ruling
it out.

Questions to ask the oncologist:
Print these or have them on your phone. Read them
from the list. Doctors expect this and prefer it.

1. Based on my blood work, what are the most likely
explanations for the elevated LDH?
2. What tests are you ordering today, and what will
each one rule in or rule out?
3. When will I get results, and how — phone, portal,
follow-up appointment?
4. If additional testing is needed, what’s the sequence
and timeline?
5. What symptoms should I watch for between now and
when results come back?
6. Is there anything I should or shouldn’t do before
the tests? (Fasting, medications, exercise.)
7. What is the most likely outcome here? I’d rather
know the probabilities than wonder.

QUESTIONS FOR THE BILLING OFFICE (before or after):
8. Will today’s visit and any tests be coded as
diagnostic or preventive? (This affects your
deductible.)
9. Can I get a cost estimate for any imaging or
procedures before they’re scheduled?

For your partner:
Your partner’s job is to write down what the doctor
says. You will be listening. You will not be
transcribing accurately — stress degrades note-taking.
Give your partner this list so they know which answers
to capture. Two people hearing the same conversation
retain different details.

What to bring:
— This question list (on your phone or printed)
— Insurance card
— A list of current medications, including supplements
— The name and contact for your PCP, in case the
oncologist needs to coordinate
— A notebook or your partner’s phone for notes

The night before:
Write down the one thing you most want to know when
you leave that appointment. Not five things. One.
If you get nothing else answered, get that one
answered.

Your follow-up:

What if they want to schedule something right away,
like a biopsy? How do I know if I should say yes
on the spot?

Your Agent:

You don’t have to decide anything in the room. The
sentence is: “I’d like to understand the full picture
before I schedule anything. Can I call back tomorrow?”

The only exception: if the doctor says the word
“urgent” or “we need to move quickly,” ask why —
“What changes if we wait a week?” — and then decide.
Most diagnostic workups are not emergencies. The
pressure to schedule immediately often comes from the
office’s scheduling system, not the medicine.

If they do schedule something, ask: “Is this
pre-authorized with my insurance, or do I need to
call first?” Unauthorized procedures on a high-
deductible plan can cost thousands. Five minutes on
the phone with your insurer prevents that.

Example 2: Before a Salary Negotiation

The situation: you’ve been at your job for two years. Your annual review is next week. You’ve been told informally that “it went well” — but nobody has mentioned a raise, and you’re making $12,000 less than market rate for your role. You’ve never negotiated salary before. The thought makes you nauseous.

Your opening message:

I have my annual performance review next Tuesday and
I want to ask for a raise. I’ve been here 2 years,
I know I’m underpaid compared to market rate, but I’ve
never negotiated salary before and I don’t know how
to bring it up. Help me prepare.

Details:
- Current salary: $62,000
- Role: Marketing Coordinator at a mid-size company
(~200 employees)
- Location: Denver, CO
- I’ve taken on project management responsibilities
that aren’t in my job description
- My review feedback has been positive both years

Your Agent’s clarifying questions:

This is exactly the kind of conversation that
preparation changes completely. A few questions:

1. Do you know what the market rate is for your role
in Denver, or is that a guess? (If you haven’t
checked, I can tell you where to look.)
2. What’s the additional project management work —
can you name two or three specific projects or
responsibilities?
3. Do you know if your company does raises at review
time, or is it a separate process?
4. Who is conducting the review — your direct manager,
or someone in HR?
5. Is there a number you’d be happy with, and a number
below which you’d be disappointed?
6. Is leaving the company a realistic option if they
say no, or do you need to stay?

Your answers:

1. I looked on Glassdoor and it says $72,000–78,000
for Marketing Coordinator in Denver. So I’m about
$12,000 below the midpoint.
2. I’ve been managing the quarterly campaign calendar,
coordinating with the design team (that used to be
my manager’s job), and I ran the product launch
project last fall by myself.
3. I think raises happen at review time but I’m not
100% sure.
4. My direct manager. They’re great — I don’t think
they’ll be hostile. I just don’t know how to start.
5. I’d be happy with $72,000. I’d be disappointed
with less than $68,000.
6. I could leave but I’d rather stay. I like the
work and the team.

Your Agent prepares you:

Here’s your preparation for Tuesday. Practice saying
these out loud once — not to memorize, but so the
words aren’t new to your mouth when it matters.

Your case in three points:
(These are the only three things you need to say.
Everything else is supporting detail.)

1. “I’ve been here two years with strong reviews both
years, and I’d like to talk about adjusting my
compensation to reflect my current responsibilities.”
2. “Over the past year, I’ve taken on project
management work that wasn’t in my original role —
the campaign calendar, design coordination, and the
fall product launch. I want to make sure my comp
reflects the role I’m actually doing.”
3. “Based on market data, the range for this role in
Denver is $72,000 to $78,000. I’m currently at
$62,000. I’d like to discuss moving to $74,000.”

Why $74,000 and not $72,000:
You anchor slightly above your target so there’s room
to meet at $72,000 — your actual happy number. If you
open at $72,000 and they negotiate down, you land at
$68,000 — your disappointment floor. Always open above
where you want to land.

The conversation map:
Here’s what will probably happen, in order:

1. Your manager will go through the review feedback.
Listen. Take notes. Don’t bring up money yet.
2. They will ask if you have any questions or anything
to discuss. THIS IS YOUR OPENING. Say point #1.
3. They will either:
a) Say they need to check with HR or their manager
→ “I understand. Could we set a follow-up
within two weeks?”
b) Ask what you’re looking for
→ Say points #2 and #3.
c) Say the budget is tight right now
→ “I understand constraints. Can we set a
specific timeline — say Q3 — to revisit
this, with a clear target number?”
4. DO NOT say “I’ll leave if I don’t get this.”
Even if it’s true, the threat changes the
relationship. The data speaks for itself.
5. DO NOT apologize for asking. “Sorry to bring
this up” undermines everything that follows.
You are not asking for a favor. You are
correcting a market discrepancy.

What to bring:
— The Glassdoor data (screenshot or printout).
If they ask where you got the number, “Glassdoor
and LinkedIn Salary Insights” is enough.
— Your list of added responsibilities with dates.
Be specific: “I’ve managed the campaign calendar
since March 2025” is stronger than “I’ve been
doing more.”
— A one-page summary of your key contributions.
Not a portfolio — just bullet points. Leave it
with them if they need to take it up the chain.

If she says yes:
Ask for it in writing — email is fine. “Thanks so
much — could you send me a quick email confirming
the new number and effective date?” This is not
paranoia. It is documentation.

If she says no:
“I appreciate you hearing me out. Can we agree on
specific milestones that would justify a raise at
the next review cycle, so I know what to aim for?”
This turns a no into a documented roadmap.

Your follow-up:

I’m worried that if I ask for a raise right after a
good review it’ll seem like I’m only in it for the
money. Is that a real concern?

Your Agent:

No. The annual review exists for this conversation.
This is the institutionally designated time to discuss
compensation. You are not ambushing anyone. You are
using the process for its stated purpose.

The discomfort you’re feeling is the same information
asymmetry the book keeps naming: employers benefit
from employees who feel awkward asking for market rate.
That awkwardness is not a personality flaw. It is a
feature of a system that saves money when you don’t
ask. You are asking.

Example 3: Before a Contractor Walkthrough

The situation: your kitchen faucet has been leaking for a month. You called a plumber. They’re coming Thursday for a “walkthrough and estimate.” You have no idea what a reasonable price is, what questions to ask, or how to tell if they’re recommending work you don’t need. Your last contractor experience ended with a $3,000 bill for what turned out to be a $400 repair.

Your opening message:

A plumber is coming Thursday to look at my leaking
kitchen faucet and give me an estimate. Last time I
hired a contractor I got badly overcharged and I don’t
want that to happen again. Help me prepare for the
walkthrough.

Here’s what I know:
- The faucet drips constantly from the spout, even
when both handles are turned off
- It’s a two-handle faucet, probably 15 years old
- I rent (landlord said I can hire someone and deduct
from rent, with receipts)
- I’m in a second-floor apartment

Your Agent’s clarifying questions:

Good — getting prepared before the plumber arrives
saves money directly. A few questions:

1. Do you know the brand of the faucet? (Check the
base or under the sink for a label.)
2. Is the leak only from the spout, or also from the
base or under the sink?
3. Have you noticed any water damage to the cabinet
below or the floor?
4. Did you get this plumber from a recommendation, or
from a search?
5. Do you have your landlord’s permission in writing
(text or email)?
6. Is there a cap on what the landlord agreed to
reimburse?

Your answers:

1. I’ll check — I think it says Moen on the front.
2. Just the spout.
3. No water damage that I can see.
4. My neighbor recommended them and said they were fair.
5. Yes, I have a text saying “go ahead and get it
fixed, save receipts, I’ll take it off rent.”
6. They didn’t mention a cap.

Your Agent prepares you:

Here’s your preparation for Thursday.

What’s probably wrong:
A 15-year-old two-handle Moen faucet dripping from the
spout is almost always worn cartridges. Moen uses
replaceable cartridges (not traditional washers) in
their two-handle faucets. The cartridge costs $10–20
per side. The repair is straightforward — a competent
plumber does it in 30–45 minutes.

What it should cost:
— Cartridge replacement (both sides): $150–250
including parts and labor. This is the most
likely repair.
— Full faucet replacement (if the plumber recommends
it): $250–450 for a standard kitchen faucet
installed. Parts + labor.
— If the quote is over $500 for a dripping faucet
with no water damage, get a second opinion.

Questions to ask during the walkthrough:

1. “What do you think is causing the drip?” (Listen
for “cartridge” or “valve seat.” If they say
something vague, ask them to be specific.)
2. “Can this be repaired, or does the whole faucet
need replacing?” (The repair is almost always
possible. Replacement is only necessary if the
valve body is corroded.)
3. “What does the repair include — parts and labor?
Is the estimate flat-rate or hourly?”
4. “How long will it take?”
5. “Is there a warranty on the work?”
6. “Can I get that estimate in writing before you
start?”

The sentence that protects you:
“I’d like a written estimate before any work begins.”
Say this before they touch anything. A professional
plumber expects this. Anyone who pushes back on a
written estimate is telling you something about how
they do business.

Red flags to watch for:
— Recommending full faucet replacement without
attempting the repair first. A cartridge swap is
cheaper and faster. If they skip straight to
replacement, ask why.
— “While I’m here, I noticed…” followed by
additional work. This is the most common upsell
in plumbing. It may be legitimate. Ask: “Is this
urgent, or can it wait? Can I get a separate
estimate for that?”
— Refusing to itemize. “$400” is not an estimate.
“$180 labor + $40 parts + tax” is an estimate.
— Starting work before providing the estimate.
Stop them. “I asked for the estimate first.”

For your landlord:
Save the written estimate and the final invoice.
Take a photo of the faucet before the repair. Text
your landlord the estimate before work begins — not
for permission (you already have it), but for
documentation. If there’s ever a dispute about the
rent deduction, you want a paper trail.

Your follow-up:

What if they say the whole faucet needs replacing and
quote me $800? How do I push back without being rude?

Your Agent:

You don’t push back. You ask questions. The questions
do the work.

“Can you help me understand why a repair isn’t
possible? Is the valve body damaged?”

If the answer is convincing and specific — corroded
valve body, obsolete parts, damage to the supply
lines — it may be legitimate. $800 is still high for
a basic faucet replacement, but ask for the line items.

If the answer is vague — “these old ones aren’t worth
repairing,” “you’re better off with a new one” — say:
“Thanks for the assessment. I’m going to get one more
estimate before I decide.” You owe them nothing for
the walkthrough except courtesy and, if applicable,
a trip charge (ask in advance if there is one).

Being prepared is not being rude. It is being a good
client. The plumbers who are worth hiring prefer
clients who ask questions.