1. What problem would you work on first, and why?
Explain the situation before asking for a package. Share what you sell, who buys it, what is happening now, and where progress seems to stall. Then listen to the questions the agency asks.
A useful answer may be provisional. They may need access to the site, reports, or customer feedback before recommending a scope. That is reasonable. Ask what they would examine and how those findings would change their recommendation.
If the answer is immediately a new website, a content retainer, and three ad campaigns, ask how they arrived there. A menu of available services is not yet a diagnosis.
2. What would you measure, and what would you need from us?
Ask what success would look like and which measures would help assess it. Have them distinguish business outcomes from the activity they control. Publishing articles is a deliverable. Suitable inquiries are an outcome influenced by more than the publishing schedule.
Discuss the baseline, reporting rhythm, sales cycle, and any gaps in tracking. Ask how your team will contribute information about lead quality and won work.
Listen for dependencies: your offer, pricing, approvals, sales follow-up, and capacity. An agency that can explain those dependencies is giving you something to manage. An unconditional promise of growth is giving you something to question.
3. Who will actually do the work?
Ask who leads the project, who you speak to, and who handles the specialist tasks. Understand whether the delivery team includes employees, freelancers, or partner businesses.
Contracting specialists can be a sensible way to assemble the right expertise. What matters is who checks the work, coordinates it, and remains responsible when something needs attention.
Ask how decisions and feedback will be recorded. Find out how often you will review progress and what happens if your usual contact is unavailable. You should be able to picture the working relationship after the salesperson leaves the call.
4. What is included, and what changes the price?
Get specific about deliverables, revisions, content responsibilities, required access, and timing. Identify subscriptions, advertising spend, and third-party costs that sit outside the quoted fee.
Ask how changes are estimated and approved. A project can evolve without becoming an invoice surprise if there is a clear way to discuss additional work before it begins.
Compare proposals on an equivalent scope. A lower quote may exclude writing, migration, testing, or support that another includes. It may also be a more appropriate, smaller project. Understand the difference before deciding which number represents better value.
5. What happens if we stop working together?
Clarify control of your accounts, access to the work, documentation, and the process for handing things to another provider. Discuss any notice period, outstanding fees, licenses, or platform limitations before signing.
Ask how unfinished work is handled and what ongoing services would stop. If advertising or hosting is involved, make sure you understand the operational consequences of ending the arrangement.
You are not predicting a bad relationship. You are checking that the arrangement is clear enough to manage. The strongest proposal should explain how the work begins, how it is assessed, and how it can be handed over. The slide transitions are optional.
Put the thinking to work
Compare answers, not just prices.
Put the five questions beside each proposal. Note which answers are specific, which depend on further discovery, and which are missing. Resolve the gaps before choosing.
See how we approach a project
Written by
Dan Reed
Founder of Multicomma. I design and build websites, ecommerce experiences, and custom tools, with a focus on what the business needs them to do.
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