Author’s Note
Welcome to another exciting week of marketing! Remember: If you have questions, just hit ‘Reply’. I read every email. Have a great week!
Ask Matchbook
This week's questions from readers:
Q: My agency wants a 6-month contract. Is that normal?
A: Yes, 3-6 months is standard. Agencies need time to test, optimize, and prove results. But make sure the contract has clear performance milestones and an out-clause if things aren't working by month 3. If they're pushing for 12 months upfront with no flexibility, that's a red flag.
Q: Is it normal for my agency to ask me to write the ad copy?
A: No. Writing ad copy is the agency's job. If they're asking you to do it, they're either (a) understaffed, (b) lazy, or (c) not actually good at what they do. You should provide input (offers, messaging, brand voice), but they should be creating the copy. Use the Vendor Scorecard to clarify responsibilities before you sign.
Today you’ll read about:
Hiring a marketing agency feels risky because sales polish can mask operational reality — the fix isn’t learning marketing, it’s asking better questions.
Strong agencies design around your actual business systems, not assumptions
Early success should have clear milestones, not vague promises
Roles and responsibilities must be defined before work starts
Mature agencies can calmly explain how they handle stalled results
Communication structure matters more than friendliness during the sale
Most business owners don’t feel confident when they hire a marketing agency.
There are real reasons for that.
Hiring marketing doesn’t feel like a normal purchase. It feels like stepping into a conversation where the other side understands the rules and you don’t.
Most owners assume the solution is learning more marketing, trying to catch up to the agency on the other side of the table.
While that would be great, it’s not actually the right fix.
You don’t need to become a marketing expert to hire one. You just need a structure for evaluating what you’re hearing and distinguishing between confidence and competence.
If you talk to a dozen agencies, all are going to sound capable. They’ll explain their process clearly, show case studies, talk about strategy. Some of them will genuinely be strong operators. Some will be average. A few might be bad.
In a sales conversation, most agencies sound identical.
Sales environments reward polish. Confidence is part of the job, and it’s completely human to interpret confidence as safety.
What helps is asking questions that expose how an agency actually operates. Not trick questions or confrontational questions, just ones that force clarity.
Here are the questions I recommend you ask to any agency you’re considering working with:
What does success look like in the first 30 to 60 days?
This question tells you whether the agency understands your side of the deal.
A lot of strategies quietly assume things about your business: That you have a CRM, that someone owns follow-up, that leads will get contacted quickly, that your budget is stable.
If those assumptions are wrong, the strategy collapses and everyone blames the channel.
A good agency will immediately start asking you questions back. How are leads tracked right now? Who handles incoming calls? How fast can you respond? What systems already exist? They’ll want to design around reality.
If they don’t care what’s happening inside your business, there’s your red flag.
What specifically are you responsible for and what am I responsible for?
Most breakdowns don’t come from bad strategy but from silent assumptions.
Content approvals. Offers. creative assets. follow-up. internal communication. Someone always assumes the other side owns it.
Good agencies draw clean boundaries. They’ll tell you what they deliver, what they need from you, and where collaboration actually happens.
If the answer sounds like “we’ll figure it out as we go,” that usually means you’ll be figuring it out under pressure later.
What happens if results stall?
This question tests maturity more than optimism.
Every channel has failure modes. No serious operator pretends otherwise.
You want to hear how they diagnose problems. What they test first. When they pivot. How they decide to change direction.
A good answer is calm and procedural, it shows they’ve seen failure before and built a response to it.
A bad answer tries to dodge the premise entirely. Agencies that can’t talk about failure honestly tend to stretch timelines instead of solving problems.
How do we communicate once we start?
Sales communication is not delivery communication.
Some agencies are incredibly responsive while they’re closing the deal and then disappear into a ticket system afterward. That shock alone causes a lot of owner panic.
The details matter less than the structure. You want to know what the relationship feels like after the contract is signed.
If communication sounds informal or undefined, expect to chase updates later.
Need more help?
Not sure which channel makes sense for your business? Get a Channel + Readiness Review.
Tried marketing before and it didn't work? Book a Marketing Reset.
Ready to find an agency but don't want to vet them alone? Matchmaking is for you.
Already working with an agency but something feels off? Get an Agency Reality Check.
Bottom line: Some business owners hesitate to ask hard questions like this because they don’t want to come across as “difficult to work with”.
Trust me, any good agency would LOVE to answer these questions for you. It indicates seriousness, which to an agency signals longevity and trust.
If someone gets irritated that you’re asking operational questions, imagine how they’ll react when you raise operational concerns three months in.
Till next time,
