Someone reached out recently. Returning to fractional work after some time away.
She had a warm lead. A friend's company, a real need, genuine interest. And she was stuck.
Not on the work. She knew what to do there.
She was stuck on how to start. How to walk into a client relationship with no clear scope, no defined deliverable, and no formal ask beyond "I think we need design leadership."
I've had this same conversation dozens of times.
This is the system I told her to use.
The Problem With Vague Opportunities
When a potential client says "I need strategy help" or "I am not sure what we need exactly, but we want to work with you," most designers do one of two things.
They either undersell (agree to something vague, get overwhelmed, burn out quietly) or overcompensate (send a long proposal before they understand anything).
Both are wrong.
The real move is to use the ambiguity as information.
When a client does not know what they want, it tells you exactly what they need: clarity. And clarity is what you are going to provide before you quote a price, sign anything, or scope a single deliverable.
Step 1: Extract the Problem List Before You Meet
Before you book anything, reach out to your contact.
Ask them one question: "What are the biggest problems your team is actively debating right now?"
Let them braindump. Do not edit. Do not filter. Just collect.
If there are multiple stakeholders, ask all of them. You will get different versions of the same few problems, described in slightly different language.
That is the point.
You are not solving yet. You are listening for patterns.
Step 2: Stack Rank With Your Contact
Once you have the list, bring it back to your main contact. This is usually the founder, or whoever you are closest to.
Ask: "If you had to rank these by urgency, what are the top three?"
This does two things:
- It forces them to make decisions before the room fills up with opinions
- It tells you which problems have real traction, versus pet projects and noise
You now have a working hypothesis for the session.
Step 3: Write the "How Might We" Questions
This is your facilitation prep.
Take the top three problems. For each one, write a How Might We (HMW) question.
The format: "How might we [solve the core problem] for [the right people] so that [the outcome they actually want]?"
Send them to your contact before the session. Ask for a quick gut check. Small adjustments are fine. Big changes mean you misheard the problem. That is useful data too.
Now you have an agenda. The session has a spine.
Step 4: Run the 90-Minute Session
Book 90 minutes.
Bring the two or three people closest to the problem. The ones who have been living with it, not the ones who only manage it from a distance.
Your job is not to arrive with answers. Your job is to extract what is already in the room.
Months of shared anxiety, competing opinions, and untested assumptions are sitting inside these people's heads. Your job is to get it out, organize it, and reflect it back.
Use FigJam, a shared document, or sit in a room with a whiteboard. Run through the HMW questions. Let people react. Let it get messy. That is the point.
By the end, you will have:
- A clearer picture of the real problem (often different from what they said initially)
- A rough ranking of where design can actually move the needle
- Enough context to write a real scope of work
Step 5: Send the SOW Within 48 Hours
Do not wait.
Within two days of the session, send a simple scope of work. Structure it like this:
- Problems we identified — what came up in the session, in plain language
- What I will tackle, month by month — three month breakdown, concrete but not over specified
- What I need from you — access, decision making power, availability
- Cost — monthly and flat, with no surprises
Three months. One focus per month. Clear deliverables by the end. That is the offer.
If you want somewhere to run this system from, including problem lists, sessions, scopes, and follow ups, that is exactly what Juggle is for. You can join the beta at joinjuggle.com.
On Charging for the Session
Here is the question everyone asks: "Do I do the 90 minutes for free?"
Ideally, no.
There are three situations.
Charge for it if the relationship is new, the company is funded, and you do not yet know if you want the work. The session is the product. Price it like one.
Do not charge if you have a strong existing relationship and you genuinely believe there is a three month engagement on the other side. Think of it as a free diagnostic, a gift that signals you are serious and builds goodwill. Be honest with yourself about the tradeoff.
Never work for free by default. If someone is not willing to pay for 90 minutes of your strategic attention, that tells you something about how they will treat the engagement.
Protecting the relationship is not about being generous upfront. It is about defining what the relationship is built on.
Why This Converts Better Than Any Proposal
Most freelancers and fractionals try to scope before they understand. They send proposals into fog.
This approach does the opposite. It uses the ambiguity as a forcing function.
The diagnostic session is not a favor. It is a product. It creates alignment before money changes hands, which means that when you do send the scope of work, both sides know what they are agreeing to.
The result is cleaner engagements, fewer scope surprises, and clients who feel like you solved something before the real work even started.
The System, In Short
- Ask for the problem list before you meet. Async, low pressure, honest.
- Stack rank with your contact. Understand what is urgent versus noise.
- Write HMW questions. Facilitation prep, shared before the session.
- Run the 90 minute session. Extract, organize, reflect, clarify.
- Send the scope of work within 48 hours. Three month structure, clear cost, no guessing.
Fuzzy opportunities do not go away. With this process, they do not stay fuzzy for long.
Gev Marotz is a fractional creative director and product designer based in Toronto. He writes about the business side of fractional work — the stuff design school never covers — and works with a small number of seed-stage startups each year on brand, product design, and positioning. gev.design
If you want a simple way to keep track of all these fuzzy opportunities, including warm intros, "we should talk" messages, and half scoped leads, I am building Juggle. It is a small CRM for fractional designers that helps you capture leads, track conversations, and turn them into scoped three month engagements instead of forgotten maybes. The beta is live at joinjuggle.com. Sign up if you want in early.
Thanks for reading,
Gev
