This month we talked about a few questioning methods. I hope you did your practicing because without it you’re not going to get better at delving deeper with your clients.

The thing is, you can’t just use a single method of questioning — you need to get comfortable enough with the different methods to flow between them. Just asking WHY five times for every facet of the conversation will quickly sound mechanical. Always using echoing will also sound ridiculous quickly. Only with practice and prep can you easily flow between the types of questioning methods so that you sound natural and can build the trust of your prospect.

Prep how?

Do you schedule 15 minutes prep time before every call? I hope you do, at least if you want to win the work.

So you’ve got 15 minutes before each call with a prospect, but what do you do with that time? I open up my email client and read through every email we’ve sent about the current work. I open up Evernote and go over every note I’ve made as we’ve been sending information back and forth.

Out of that reading I generate at least 5-8 questions I need answered about the project by the end of our 30-minute call. The first thing I do when I’m on the call with the prospect is to let them know what those 5-8 questions are and tell them that by the end I need those questions answered.

No, this doesn’t make you less personable and abrupt with your prospects but rather shows them that you came prepared. It increases their trust in you because if you put this much effort into a phone call with them how much effort will you put into the project?


This also sets a clear agenda for the call and at the end allows you to evaluate if the call was a success or not. What I actually say is:

Hey $name, I have 5 questions I need answered by the end of the call. I need these answered to have a successful call. The questions are:…

They weren’t answered

Many of your calls with prospects will result in all your questions answered properly but not all of them. Sometimes there are just too many unknown things in the project and you couldn’t answer them even with two years of phone calls.

If you have an effective call (no waffling around about the weather) and haven’t answered the questions in 45 minutes then the project is likely too big for just sending a proposal. In that case, you most likely need to have a scoping session which is a billed project.

The entire goal of scoping sessions is to figure out the project and make sure that everything is understood. For one I have coming up it means digging into the project and figuring out which of the client needs can and can’t be done with their current infrastructure. If we can’t do what we want then it means we’ll recommend a new option.

Either way, after finishing the paid scoping (or discovery if you prefer) I’ll be able to produce a proper proposal for the client so we can move forward with the rest of the project.

Get better at questioning

Do you want to get better at questioning? Do you want to not sound like a robot as you flow between questioning methods? Of course you do, so start practicing.

If you’re not in a mastermind group to practice with, go find one. If you’d like some 1 on 1 help I’d love to talk with you about how I can help.

Start learning to ask better questions today so that you can land more clients and charge more as you find more value in each project.

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