Somebody says “yeah, we can do that.”

And sure. They can do it. But do they have any idea what they’re doing?

That gap is where most of the damage happens. A website goes down. A domain lands on a blacklist. You burn through $10K in media spend when the budget was $5K. No tagging, no tracking, so a year of reporting is worthless. The tech stack is held together with tape.

Some of that shows up right away. Some shows up months later as a problem nobody can explain.

None of it is usually malice. It’s a mismatch between what you thought you were buying and what the other side thought they were selling, and almost all of it is catchable in the first conversation.

What am I actually paying for: traffic, leads, or customers?

Traffic, leads, and customers are three different purchases and they look identical on an invoice. Traffic is visits and impressions. Leads are form fills and inquiries. Customers require everything upstream to work plus someone accountable for the outcome. Ask which one is being sold.

A good partner answers this plainly. Hedging is the signal.

Most disappointment in marketing relationships comes from paying for one of these and expecting another. The vendor delivers exactly what they sold, the reporting is honest, and the business result never arrives. Nobody did anything wrong and nobody is happy.

Who is actually doing the work every week?

The person in the pitch is often not the person on the account. Ask who touches your work weekly, how many other clients they carry, and who picks up the phone when something breaks. Vague answers here predict vague accountability later.

This isn’t a gotcha. Senior people selling and other people delivering is a normal structure and plenty of good work happens inside it.

The problem is only ever not knowing. If you expected the person you met and you got someone three months into the industry, that’s a surprise you could have avoided by asking.

How will we know if this worked?

Agree on what success looks like at 30 days and at 90 before anything starts. At 30 days you’re looking for early movement in things like engaged visits and replies. At 90 you should see results or have a clear reason why not.

And ask the harder half of the question: what would failure look like?

If nobody can describe failure, nobody will recognize it. You’ll be eleven months in, vaguely dissatisfied, with no agreed standard to point at.

What happens if this isn’t working in 90 days?

Ask before you sign. The answer tells you how the relationship will actually go. Look for a specific response about what gets reviewed, what can be changed, and what the exit looks like, rather than reassurance that it will work.

Contracts matter less than the reaction. Somebody who has thought about this has an answer ready. Somebody who hasn’t will tell you it won’t come to that.

What does this not include?

Every engagement has edges. Ad spend, design beyond templates, specialist work, new tool subscriptions, and strategy are commonly outside a retainer. Find the edges before you’re standing on one.

This is the question people skip because it feels adversarial. It isn’t. A clear answer protects both sides, and most of the friction in marketing engagements is scope ambiguity that nobody named at the start.

Who owns the accounts and the data?

Make sure your business owns the ad accounts, analytics properties, domain, CRM, and website, with the vendor added as a user. If you leave and the data stays behind, you lose your history permanently and you can’t reconstruct it.

This one costs nothing to ask and is expensive to discover later. Historical data can’t be rebuilt after the fact.

Can you tell me about something that didn’t work?

Ask for an engagement that went badly and what they learned. Anyone with real experience has one. An inability or unwillingness to answer usually means either limited experience or limited self-awareness, and both are a problem.

You’re not looking for a confession. You’re looking for whether they can think critically about their own work, because that’s the same skill that will catch problems on your account.

What should you listen for in the answers?

A few patterns worth noticing:

• Specifics instead of reassurance. “We’ll make sure it works” is not an answer to any of these questions.
• Willingness to say what they don’t do. Someone who claims every capability usually has depth in none of them.
• Questions coming back at you. Good partners interrogate the brief before they price it.
• Comfort with the uncomfortable questions. Defensiveness about accountability now predicts defensiveness later.
  
  

The bottom line

Most marketing relationships don’t fail because somebody was bad at their job. They fail because two parties agreed to something without ever defining it, and the gap only became visible once money had been spent.

Twenty minutes of questions at the start prevents most of it.

If you’re about to hand a meaningful part of your marketing to someone and you want a second set of eyes on the decision, that’s the kind of thing I do.  https://taralilly.com/contact/