One common prospecting advice in freelancing circles is initiating a prospect contact with specific feedback and suggestions on how to improve their content or content strategy.

It makes me cringe and want to look away.

That’s a risky move that could kill your sale. 

Let me explain. A few years ago, I was your ideal prospect: a marketing manager with a big content budget, looking to outsource some creative work. Over the years, I had quite a few vendors and job candidates approach me with specific criticism or recommendations for how to make my company’s website/content/materials/whatever better. I don’t remember a single time that went over well. (Keep in mind we’re talking about our first interaction here.)

That’s because they often failed to realize a few things:

  • I wrote the content they were tearing apart, and the unsolicited critique felt like personal criticism.
  • Sometimes I agreed with their assessment, but couldn’t act on it. Maybe an internal committee shot down the idea, my boss didn’t like it, legal wouldn’t let me, or someone higher on the totem pole made me change it.
  • Their recommendation lacked knowledge of our company goals, audience dynamics, past/failed experiments, or other issues that made the advice wrong for us, even if it seemed reasonable on the surface.

Without those insights, those interactions felt presumptuous, and put my team and me on the defensive. I mean, how would you like it if a stranger walked up to you and pointed out all they deemed wrong with your outfit, hair, and personal grooming? That’s how it felt, and it’s something I never want to do to a prospect.

Am I saying you shouldn’t offer guidance on how a prospect can achieve better results? NOT AT ALL.

What I’m saying: Don’t offer a prescription before you diagnose your prospect’s pain.

You wouldn’t trust a stranger peddling a pill for a condition you don’t even think you have, would you? So why should a prospect change their strategy, pull out their credit card, and implement the advice of someone who knows nothing about their organization, audience, goals, and obstacles?

(If you’re in our Facebook group, you’ve likely noticed I’m fond of the doctor/patient metaphor to illustrate how to be perceived as a trusted advisor instead of a money-hungry vendor.)

As it happens, positioning yourself as a trusted advisor is easier than it sounds.

First, stop talking so much.

Stop pushing solutions before your prospect has a chance to speak.

Instead, ask questions. Then listen. Ask follow-up questions. Listen some more.

Sample questions you could adapt to your target:

  • Tell me about your sales/marketing goals. What happens if you don’t meet those goals?
  • How do you attract, convert, and retain customers today?
  • What’s working? What’s not working? How do you know that? Are you basing it on data or a gut feeling?
  • Where do your most profitable customers come from?
  • Who’s your ideal customer? What problems do they want you to solve for them?
  • At what point do potential buyers seem to stop responding?
  • Do most of your customers come back for repeat buys? Why do you think that is?
  • What common objections or tripping points have you observed in the buying process?
  • What questions, requests or complaints does your customer support team hear often?
  • What do you do differently or better than your competitors?
    … and so on.

As it happens, the best persuaders are the best listeners.

When you uncover clear problems you can alleviate with compelling content, that’s when you present your recommendations. By then, you’ll have a ton more respect and rapport with your prospect than you started with.

Diagnose before you prescribe.

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