How I Learned To Handle The Most Frustrating Client Objections

A.K.A. The Questions Tom Hopkins Leaves Us Asking

I don’t always close the project right away. When I was starting out, I didn’t even know how to begin approaching people for business. In fact, I used to walk away from so many opportunities the moment I smell rejection. Growing out of my own fear of failure, I learned how to win over the most difficult clients by familiarising myself with Tom Hopkins’ Buyer Personas. If you’ve ever encountered your own versions of clients from hell, then it’s highly likely that they are one or a couple hybrids of these Buyer Personas. Instead of ranting away about your frustrations on social media, why not try asking them the following questions instead:

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If your client is always asking for free stuff or discounts, we’ve got to make them feel important through follow-ups and giving service with a more personal touch.


“How can we make this deliverable more tailor fit to your needs and budget constraints?”

If that doesn’t work, let them know that you’ve got your own thing going on and ask them how they’d prefer to deal with it. After all giving them the stage, lets them know that they’re in control.

“Since I also need to consider my overhead expenses for running my business, how can we make this a win-win for us?”

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If your client is always asking for numbers and is keen on taking everything word per word, always make sure keep everything well documented.

Ask them:

“What kind of assurance can we provide to make this set-up more comfortable for you?”

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If your client is always hesitating to talk about their budget or set up appointments, ask “What could go wrong if we don’t succeed with this project?” to make them realise how valuable your service would be for them.

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If your client is always complaining about every little nasty detail (or being a Karen), always ask for their insight and listen to them to make them feel that their suggestions matter to your business. Because people love giving advice, it would also warm them up to trusting you.

Drop questions like:

“What do you think is missing?”

Followed up with:

“How does this make you feel?”

“Is there anything else?”

“How can we make this better for you?”

The key is to extend your patience as much as possible and try to look at things from their point of view. Your extended empathy could help you build lasting relationships with them and earn their trust.

But hey, let’s keep in mind that there’s always two sides of a story. Maybe it’s not them? Maybe it’s us. Either way, let’s go out there and find our own people to serve.



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Jessica Gulapa | Jesscadoodles

Jessica Gulapa | Jesscadoodles


I share ideas that help you get smarter at making a business using your own talent & skills. Conversion Designer (