Questions to ask before paying for a content strategy

Most businesses burn money on content strategy because they skip the hard questions upfront. They assume a strategist "gets it" and hope for the best, then six months in they realise nobody agrees on what success looks like, or the plan doesn't fit how their business actually operates. The difference between a wasted investment and a solid strategy often comes down to whether you asked the right things before signing anything.

The questions below are not academic. They force a strategist to show their working, reveal what they actually know about your business, and expose whether they're selling a template or doing real thinking. Good strategists welcome them. Evasive ones dodge, fluff, or flip the question back to you immediately.

What does "success" mean in your world, and how will we know we've got there?

This is the first filter. Listen carefully to the answer.

A weak response sounds like: "We'll increase engagement," or "build brand awareness," or "grow your audience." These are not measures. They're wishes. A strategist who says this hasn't asked you what actually matters to your business.

A strong answer ties strategy to your business outcome. It might be: "Your services are booked through your website. We'll track how many qualified leads come from content, which channels send the most bookable inquiries, and how many of those convert to revenue." Or: "You want to be known in your region as the expert in your niche. We'll measure that through search rankings for your core keywords, inbound inquiries mentioning your content, and how often competitors' prospects cite you." The strategist should ask *you* first—what does winning look like for you?—before they suggest metrics.

If they talk about vanity numbers (followers, views, likes) without connecting them to your real goal, keep interviewing.

Walk me through how you'd figure out what to write about and who you're trying to reach.

This reveals their research depth. A real strategist doesn't guess. They investigate your market, your audience's actual questions, and where they're already searching or gathering information.

Evasive answers sound like: "We'll post three times a week" or "We'll create content about your services." Neither explains *why* or *for whom*.

A credible answer sounds like: "I'd interview five to ten of your recent clients to understand what problem they had before they found you, what they searched for, and what nearly stopped them buying. I'd map your competitors' content to see where they're winning and where there are gaps. Then I'd look at search data for your industry to see what people in your region are actually asking about." They might also ask you about your quieter and busier seasons, because content strategy should account for when people are actually ready to buy.

Ask them how they plan to understand *your* customers specifically, not just your industry in general. Generic is cheap. Tailored costs real time.

If we go ahead, what happens in week one, and what do you need from me?

This question separates professionals from hobbyists. It also exposes unrealistic expectations early.

A vague answer is a red flag: "We'll start creating content" or "We'll set up your socials." These don't tell you what's actually happening or what you're supposed to do.

A useful answer names concrete steps: "Week one is discovery. I'll send you a brief questionnaire, schedule three calls—one with you, one with someone from sales, one with a team member who handles customer questions daily—and I'll audit your website and current content. By end of week, I'll give you a summary of what I found and my initial thoughts." They should also tell you: do they need access to your analytics? Do you need to brief your team? Will they want monthly check-in calls? Can they work independently or do they need your input weekly? Real strategists are clear about the time commitment they expect from you, because strategy fails when the business partner disappears.

If they won't say what happens first or how much of your time it takes, they haven't thought it through.

A good strategist interview will feel less like a sales pitch and more like a working conversation. You should leave it knowing what they'll actually do, how they'll measure it, and whether they understand your business. On Strove, you can request detailed briefs from verified strategists and compare their answers to these questions side by side before you decide.