The Upside Session

How this works

You drive it. They answer. This is a call, not a form. Share your screen, ask the questions out loud, and click their answers in as they talk. Seeing their own words go down is half of why it works.

Anything marked Ask them is a question you ask. The last section, marked You fill this in, is your fee and your estimate of their time. Don't show them a price until the end.

Every question is written in their voice, so you can read it straight off the screen. "What do you charge for an hour of your time?" means exactly that. Ask it, type their answer.

Setup

Ask them

Fill this in while they're talking. Share your screen. Click the pills that fit and type anything else in the box underneath.

Who we're talking to

Date

What do you charge for an hour of your time?Their normal rate. All the time questions run off this number.

How many weeks a year do you work?Leave it at 46 unless they say different.

Why now

Ask them

Click what fits, then add their own words. Looking for a real trigger. If there isn't one, the deal isn't ready and you've just saved yourself a proposal.

Why now? You could have done this last year or next year. What changed?

What happens if you do nothing for another twelve months?

Has this already cost you something? A client, a launch, a weekend?

Who it hits

Ask them

Same question, three angles. Most people only arrive having thought about one of them. Widening this is the part they can't do alone.

Your clientsWhat's different for them? What do they get that they don't get today?

YouWhat's different about your week? What do you stop doing?

Your businessWhat can the business do that it can't do today?

Make more money

Ask them

This is usually the biggest number, and the one they walked in without thinking about. Push here.

What could you sell that you can't sell today?Group program, lower tier, licensing to a company, the people you turn away.

What would you charge for it?

Charged how?Per what, exactly?

How many would you sell in the first year?Give me three guesses. Start with the slow year. That is the only one the maths uses, so nothing here rests on the best case.

A slow year

A normal year

A good year

Any other money this brings in?Clients staying longer, work you turn away today, anything not covered above. A year's worth.

A slow year

A normal year

A good year

Bucket total: $0 low

Save money

Ask them

Money they stop spending. Usually smaller, but it's the easiest number for them to believe.

What are you paying for now that this replaces?Staff hours, contractors, tools. Or: if you hired someone to do this, what would you pay them?

How much is that a year?

Save time

Ask them

Hours only turn into money if they would actually have sold them. Be straight about that. Being straight here is what makes the rest of the number believable.

What are the hours going into today?

How many hours a week does that take?

What is an hour of that time worth?If these are your hours, use your own rate. If it is your assistant or a staff member, use what you pay them.

What would you do with those hours?If the honest answer is "not sell them", tick the box below.

They would not actually have sold those hoursTicked, this time stays out of the payback number. It still shows up on the page, just not in the maths.

Bucket total: $0 a year

Look better, or lower the risk

Ask them

Real, but you can't prove it. Tell them out loud you are leaving it out of the numbers. Leaving something out on purpose is what makes the rest believable.

What does this do for how you're seen?Deals won, referrals, standing against competitors.

What breaks if you're unavailable for a month?

Not counted. None of this goes into the maths. That is deliberate.

What it costs

You fill this in

This part is your numbers, not theirs. Include their time as well as your fee. Counting the annoying parts is what buys you trust.

What you are charging them

Anything they pay you every month after that?Leave at 0 if there is nothing ongoing.

How many hours will this take of their time?Interviews, reviewing drafts, sending you material. Across the whole build.

What is an hour of their time worth?

The payback number uses the slow year, and only counts real money coming in. Time saved is left out. If it works on the gloomy version, you never have to argue about the good one.