The 7 Questions I Ask Before Every Proposal

“We need help” isn’t a brief.

I run gev.design, a fractional creative studio working across product, brand, marketing and development.

Most leads arrive without much of a brief.

“We need help with product.”

“Our marketing isn’t working.”

“We need someone senior, but we’re not ready to hire.”

That’s the entire email.

Before I write a proposal, I need seven answers.

Seven questions to ask first

1. What changed?
   Did a leader leave? Did a launch slip? Did the team grow?

2. Why does it matter now?
   What happens if they wait another three months?

3. What decision has no owner?
   The roadmap? Positioning? Priorities? Performance?

4. What’s waiting costing the company?
   Time? Revenue? Morale? Momentum?

5. Do they need leadership, production or both?

6. Who’ll do the work?
   Their team? My collaborators? Me?

7. What should be different in 90 days?
   Name something everyone can see.

If I can’t answer these questions, I can’t write the proposal.

Find the decision underneath

The first call’s spent working out what’s happening inside the co and why it’s become difficult to manage.

A launch may be slipping.

A leader may have left.

The roadmap may change every time the founder talks to someone.

Marketing may be doing a lot of work without knowing what the company wants to be known for.

The client experiences this as a collection of problems.

I’m looking for the decision underneath them.

Founders rarely say nobody owns a decision.

They say the team needs to “get aligned.”

and I’ve learned to be suspicious of that phrase.

It might mean nobody has decided which customer matters most.

It might mean every product request is urgent.

It might mean product and marketing tell different versions of the same story.

Sometimes everyone’s waiting for the founder to settle it.

That’s usually where my work starts.

Who chooses the customer?

Who decides what gets built?

Who has the final say when two teams disagree?

What should the company stop doing?

A fractional engagement needs a clear area of ownership.

“Help us with marketing” leaves too much open.

“Own our positioning and demand strategy for the next six months” gives me something I can shape.

Choose the right engagement

About halfway through the call, I can usually tell what kind of help the company needs.

Fractional leadership

The decisions need an owner, but the company doesn’t need that person every day.

Interim leadership

The company needs heavier coverage for a limited period.

Execution support

The decisions are clear. The company needs people to do the work.

A paid diagnostic

The problem’s real, but still too unclear to scope.

Nothing yet

There’s no urgency, budget, authority or clear buyer.

Here’s the simple test:

If the decisions are unclear, they need leadership.

If the decisions are clear but the work isn’t getting done, they need execution.

If neither is clear, start with a paid diagnostic.

If nothing happens when they wait, they probably don’t need anything yet.

Define the role

I often do hands-on work as part of a fractional engagement.

The trouble starts when nobody defines the mix.

How much of my time will go toward making decisions?

How much will go toward managing people?

How much will go toward writing, designing or building?

If everything’s in scope, I don’t own a function.

I absorb chaos.

I also need to know whether the role can even be done part-time.

Some companies need a senior person once or twice a week to settle priorities and keep the team moving.

Others need someone answering questions all day.

At that point, I’ve accepted a full-time job and agreed to send a part-time invoice.

So I think about and ask:

• How many decisions will need me each week?

• Which meetings matter?

• What counts as urgent?

• Can the team keep moving when I’m not there?

Then I ask the question that causes the most trouble when nobody answers it:

Once I make the decision, who does the work?

Every strategy eventually becomes production.

Someone has to write the copy, change the product, launch the campaign or rebuild the forecast.

Sometimes the client has a capable team.

Sometimes I bring in collaborators.

Sometimes I do part of the work myself.

If the answer remains unclear, I assume I’ll do it.

I usually do.

Describe what will change

Most proposals are full of activities.

Run workshops.

Review the strategy.

Meet the team.

Build a roadmap.

Attend leadership meetings.

Those tell the client how I plan to spend my time.

I’d rather describe something we can see.

The team knows what to build next.

The founder no longer approves every campaign.

Product and marketing describe the company in the same way.

Everyone knows who gets the final say.

These changes become the backbone of the engagement.

They also give us a way to see progress before the larger business results arrive.

Vagueness isn’t a reason to write a broader proposal.

It’s a reason to keep asking questions.

Send this follow-up

After the call, I send something like this:

Based on our conversation, the main problem appears to be [problem].

This is causing [cost or consequence].

I recommend [type of engagement] for [period or commitment].

I’ll own [decisions or responsibilities]. [Person or team] will handle [execution].

Within 90 days, we should see [three visible changes].

Here’s what that might look like:

Based on our conversation, the main problem appears to be ownership of product priorities across product, design and engineering.

Your team can execute, but the roadmap changes whenever a new request reaches the founder. Work keeps restarting and the launch is slowing down.

I recommend a 30-day diagnostic followed by one day a week of fractional product leadership.

During the first month, I’ll define the priorities, who gets the final say and how the team will make decisions. After that, I’ll own the roadmap and work with the existing team to keep it moving.

Within 90 days, the goal is one agreed roadmap, a clear decision process and fewer priorities changing halfway through the work.

That gives the client something concrete to respond to.

It describes their problem, the role I’ll play and the result we’re working toward.

That’s much easier to buy than:

Here’s my fractional product package.

“We need help” isn’t a brief.

Helping the client turn it into one is often the first useful thing I do.

Keeping it clear is harder.

Across several clients, decisions, promises and next steps disappear quickly.

That’s why I’m building Juggle.

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No extra admin.

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Thanks for reading,

Gev