5 Questions to Ask Before Hiring an Agency or Freelancer

Here are the five I always ask before committing to any external partner.

1. What does success look like in the first 90 days?

This forces them to get specific about outcomes, not vague promises.

2. Can you show me results from businesses like mine?

Relevance beats flashy logos. If they can't prove experience at your stage, that's a red flag.

3. Who will actually be working on my account?

Agencies often pitch with senior talent but hand you off to juniors once you sign. Ask before you commit.

4. What will you need from me to succeed?

A good partner knows this is a two-way relationship. They should have a clear answer.

5. How do you handle reporting and transparency?

Without clear data sharing, you'll be flying blind. Get specifics on cadence, format, and access.

The best partners answer these questions confidently and without hesitation. If they can't, you've already learned what you need to know. The full Hiring the Right Agency bundle inside The DTC Operator includes my complete vetting filters, how I structure agency contracts, and the onboarding process I use to set partnerships up for success. It's $29. [Get the bundle →]