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Ask Questions, but Don't Die

When I first started in sales, I knew asking questions was the best way to get where I wanted to go with a prospect. I knew because it's what my Dad did to me ALL THE TIME, and he's an incredible sales professional. Someone told me I should study the Socratic Method. He asked many questions and won a lot of arguments, but they killed him in the end... so maybe we need a better example.

Diagnostic Questions

One of the fastest, and most effective ways to establish yourself as an expert

and build trust by asking some relevant questions that show your prospect your expertise with their own business.

I work with a lot of MSPs, so it's easy for me to ask 5-8 questions that:

  1. Gives me insight into their operational maturity, and sales acumen

  2. Moves the conversation about their needs from the general to the highly specific.

  3. Puts people at ease because they know they're talking to an expert and it doesn't feel like an interrogation.

This is obviously much easier if you have a vertical that you've chosen to focus on (which I highly recommend), but it isn't mandatory for the idea to work well.

Good diagnostic questions usually sound something like:

  • Are you using Software X or Software Y for your CRM?

  • Have you started doing A, B, or C to respond to [industry-specific regulation]?

  • My other clients have an EBITDA of around 20%, are you above or below that?

  • When you try to do [task] are you having trouble getting [specific result]?

  • What happens now when [unique, specific problem]? How do you deal with it?

The more specific, granular, and jargon-heavy these questions, the more effective they'll be. If done correctly, somewhere around five or six of these questions, the prospect can't help but think: "Ok, these people already know a lot about my business." Now you have trust. Now you have authority. Now it makes sense to ask penetrating questions to fully understand their relationship to the problems they're facing. You're not just some salesperson looking to earn a client, you're a subject-matter expert who wants to make sure they've completely understood the situation. Now maybe they won't want to poison your coffee.


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