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9 questions to ask before you sign a marketing retainer

By Jay Corey • October 21, 2026 • 2 min read

A retainer is a promise to pay every month. It deserves a little more scrutiny than a bagel order.

Here are nine questions to ask before you sign anything. Get the answers in writing. If someone gets weird about that, you’ve learned something.

The questions

  1. What exactly will you do each month? Not “social media management.” Which platforms, how many posts, who writes them, who approves them.
  2. Who will actually do the work? The person pitching you and the person doing the work are often different people. Ask to meet the second one.
  3. How will we know it’s working? Ask for the specific numbers, in plain English, and how often you’ll see them.
  4. What does the monthly fee include, and what doesn’t it? Ad spend, tools, design, extra revisions. Know what’s extra before the first invoice.
  5. Who owns the accounts and the work? Your ad accounts, your website, your files. They should be yours, always.
  6. How do we get out? Ask about the term, the notice period, and any fees. A good partner is comfortable with this question.
  7. What happens if something goes wrong? Missed deadlines, bad results, a mistake. Ask how they handle it.
  8. What do you need from me? Marketing fails when the client can’t give feedback or approvals on time. Know your side of the deal.
  9. What would make you tell me this isn’t the right fit? Honest partners can answer this one. Most won’t have thought about it.

How to read the answers

Clear, specific, a little uncomfortable? Good sign. Vague, shiny, or “we’ll figure that out together”? Be careful.

You’re not being difficult. You’re about to hand someone a lot of money and a piece of your reputation. Nobody who deserves the work minds the questions.

If you already signed one and you’re not sure, a Second Opinion is built for exactly that.

Less talk. More done.

Talk to a human Stan, the Constant mascot, on the phone saying you got a human.

30 minutes. No pitch deck. No synergy.