Every agency pitch is designed to answer the questions you're most likely to ask. The agencies that have been doing this for a while know exactly what founders want to hear and know how to deliver it convincingly.
The questions that reveal what working with an agency is actually like are the ones they don't expect.
The Questions That Cut Through
Tell me about a campaign that didn't perform as expected and how you handled it. This is the most revealing question in the process. Every agency has had underperforming work. How they talk about it — whether they take responsibility, whether they have a clear account of what happened and what changed, whether they can do so without deflecting to external factors — tells you more than any case study.
How do you communicate when things aren't going well? Agencies that communicate proactively when performance is below target are fundamentally different to work with than ones that wait to be asked. Ask this directly and watch whether the answer is specific or vague.
Who specifically will be working on our account? The senior team presents. The account is often managed by someone more junior. This is not inherently a problem, but it should be disclosed clearly. Ask to meet the people who will actually be doing the work.
How do you measure success for a brand at our stage? The answer reveals whether the agency understands your stage and your specific constraints, or whether they're applying a generic success framework that may not match your situation.
What would you not do for a brand at our stage? The agencies that are honest about the limits of what's appropriate for your specific situation — the channels that aren't right yet, the investments that don't make sense at this scale — are the ones operating in your interest rather than their own.