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Choosing an agency

7 questions to ask a marketing agency before you sign

…and what strong answers sound like

By Kim Fitkin · June 2026

Picture the first real conversation with an agency you're excited about.

The deck is gorgeous. The case studies gleam. Someone across the table is finishing your sentences about your own business like they've been quietly in love with it for years. You're nodding. You're a little giddy. You can already see the two of you building something great together.

It's a date. A really good first date. And like any good first date, everyone's leading with the highlight reel — best stories, best angles, no mention of the ex who still won't hand back the Google Ads account.

That's not a knock on them. We all do it. You did it on your last sales call too 😉

But somewhere under the butterflies, there's a quieter version of you doing math. This is your business. Depending on the month, it's thousands — sometimes hundreds of thousands — of your dollars. And the most charming person in the room isn't always the one you want holding that.

So here are seven questions to ask before you sign.

Not gotchas. Just the ones that slip past the highlight reel and show you who you're actually about to date.

One rule, and I mean it: don't take the first answer and move on. Ask again. Lean in. Watch what happens in the pause. The pause is where the truth lives.

Ready? Let's go!

1. What other brands do you work with?

Watch what happens when you ask this one.

Some agencies reach straight for the logo wall, the grid of recognizable brands they keep ready for exactly this moment.

It's impressive for about four seconds. Then it hits you that a logo doesn't tell you a single thing about what they actually did.

So drift right past it. Ask for one client who looked like you on day one — same size, same model, same beautiful mess. Then settle in and listen for a story with a before and an after.

👉 "Here's where they were when we met. Here's where they are now. Here's what we changed in between."

And while they talk, notice which word they keep reaching for: we or they. "We launched fourteen campaigns" is a story about the agency. "They went from $90 a lead to $40" is a story about the client. Only one of those is the thing you're paying for.

2. Who's going to be assigned to my account — and how many accounts do they carry?

(okay this is a 2 in 1 question)

Small question. Big door.

See the org chart hiding behind the smile. Are you getting this person — the sharp one who's been charming you all meeting — or are you about to be walked down the hall and introduced to someone you haven't met?

Either can be fine.

New faces are how agencies grow. But you're allowed to wonder out loud. A fresh hire might mean they're scaling. It might also mean they're stretched thin, or someone just walked out the door last week. Ask, and watch how easily the answer comes.

Then do a little math right there in your seat. Weekly calls, they said. Forty accounts per manager, they also said. What does that calendar look like? Now picture where, exactly, your account fits into it, and when the actual work happens.

You don't have to say any of that out loud. Just file it away. (And keep it handy. Question 7 comes back for it.)

3. What's your biggest success story?

Everyone's got a favorite story. Let them tell you. Then gently turn the lights up.

Before they even start, decide privately what success means to you. More leads? More pipeline? More money in the bank by spring? Hold that quietly in your head while they talk.

Because most success stories show up dressed in adjectives.

"Transformational." "Game-changing." "Unbelievable synergy."

Amazing stuff. Now picture yourself asking, very pleasantly, "Sure, by how much?"

The good ones don't blink. "We took them from $2M to $10M in a year, mostly by rebuilding their paid search and unclogging a checkout flow that was leaking sales."

A number and a reason. That's a story. Everything else is just a nice mood.

4. Have you ever had a client fire you?

This one's my favorite, because you learn the most from the flinch.

Picture three different answers landing across the table.

  1. The first one blames the client — bad fit, wouldn't listen, never gave it time. File it. You're watching a preview of how they'll talk about you someday.
  2. The second is worse in a quieter way. "Honestly? Never." Picture keeping your face perfectly still. Anyone who's been at this a while has been let go at least once. That answer isn't confidence. It's a tell.
  3. The third is the one you're rooting for. They walk you through a relationship that fell apart — why it fell apart, how they handled the breakup, what they changed afterward. Which sets up the best follow-up in the whole conversation: "So…how am I different from that?"

Lean all the way in for that answer. Because somewhere down the line, on some unremarkable Tuesday, they're going to get something wrong. Everyone does.

You're not shopping for a partner who never stumbles. You're shopping for the one who gets back up and tells you the truth about it.

5. What happens when it's not working?

Every relationship gets a honeymoon. Imagine the morning it ends.

A campaign goes quiet. A platform rewrites the rules overnight. A whole quarter just… doesn't. It's coming, for all of us. The only real question is whether you two already talked about it — or whether you're discovering it together at 9pm on a Friday.

So ask now, while it's all sunshine: "When the numbers dip, what actually happens? How fast do I hear from you?"

Then picture the answer you're hoping for. They don't sit on bad news until the monthly report. They come to you early, with a theory and a next move instead of a shrug. You find out about the problem from them — not from your own dashboard at midnight.

And while the mood's honest, slip in the unromantic questions too.

6. How do you actually use AI?

Go ahead, ask the 2026 question out loud. Then watch their faces.

AI is in everybody's workflow now — yours too, probably. So this isn't a trap. It's a "show me your hands" moment.

Picture the two answers you don't want. One is the agency quietly charging you premium rates for something a chatbot produced in about ten seconds. The other is the team that won't touch the stuff, moves at half speed, and charges you full price for it.

Now picture the one you do want.

Relaxed. Specific. "AI handles the grunt work — research, rough drafts, sifting the data, running the tests. People handle the thinking — the strategy, the judgment, the calls that actually move money." Tools in one hand. The thinking held firmly in the other.

That's who you want in your corner.

7. Who's actually doing the work — and how does it get done?

Remember that 40-accounts math you filed away back in question 2? Pull it back out. Here's where it earns its keep.

Ask them to walk you through a normal month on your account, and really picture it as they talk.

None of those are wrong, by the way. Juniors, automation, freelancers — that's how good work gets made at scale. You're not hunting for villains. You're just checking that the movie matches the trailer: that the people, the hours, and the promises all add up to the same story.

If they can paint that month for you without breaking a sweat, great. If they're clearly building it as they go, you'll feel that too.

The thread running through all of this

Here's the part none of these questions admit out loud: not one of them is really about catching someone out.

They're about finding the person who can take a hard question and give you a straight answer, because that's the same person who'll give it to you straight when a hard month rolls around too.

So ask. Then ask again. Dig a bit deeper. Let it get uncomfortable. Get curious. Get a little nosy. Enjoy yourself. The right partner won't flinch.

They've been hoping the whole time that you'd turn out to be the kind of client who cares enough to ask.

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