Catharine O’Leary: How Entrepreneurs Can Use Questions To Attract Ideal Clients

Catharine O'Leary

As an entrepreneur, you know that attracting new clients is essential to your success. But what if you could do it in a way that was fun and easy? It turns out, you can. All you need are some well-chosen questions.

Here are four steps to use questions to attract new clients:

Step 1. Use questions to “Stop the Scroll”

If you want to attract ideal clients, you need to get noticed first and you don’t have a lot of time to catch their attention. A goldfish has an attention span of 8 seconds while our attention span is just 7 seconds!

A key question, or question hook, is a great way to stop the scroll and get your ideal clients’ attention with an ad, a promotion, an email subject line, etc… One of the best questions to ask is the one that your ideal clients are losing sleep over. What’s the one question that is keeping your ideal clients from getting a good night’s sleep? That’s what they want help with.

For example, let’s say you are an executive business coach, and you serve entrepreneurs who want to scale their business from 6 to 7 figures. That’s a big mindset shift for the entrepreneur and keeps many up at night! You could start with a question like, “What’s the #1 thing stopping you from hitting 7-figures in your business?” or “What’s your 7-figure superpower?”

The people you want to serve are already looking for the solution keeping them up at night and that you happen to help solve. You just have to catch their attention and then help them learn more about your solutions.

Step 2. Use questions to start a conversation.

Once you have your ideal clients interested in finding a solution to the problem keeping them up at night you can then use questions to continue the conversation with them.

Use questions to help your clients better understand their current situation, challenges, and hurdles to reach the next level they desire. Asking questions that are specific to your ideal client’s key problem creates a rapport with your clients, helping them to get to know, like, and trust you.

For example, let’s say you have a Virtual Assistant business, and you serve entrepreneurs who need to delegate certain tasks. You likely want to know more about their business to best serve them with solutions to their delegation needs. By asking questions like “How long have you been in business”, “How many team members do you have”, “What systems do you use”, and “What’s a challenge you have faced when delegating tasks in the past?” you are gathering information about what they need conversationally.

This is especially effective if you can develop a conversation that takes your ideal client on a journey from the problem that they need to solve to the solution that you and your business can offer.

Step 3. Use questions to lead to insights

As you’ve stopped your clients in their tracks by posing a problem they need to solve, you’ve asked them about their current situation and where they’d like to go, and now it’s time to fulfill the promise of a solution to the problem. Don’t leave your clients hanging!

For example, let’s say that you are a speaker coach, and you help people get on 100 stages in 1 year. You’ve captured their attention with a question like “What’s your secret weapon to booking 2 stages a week?”. You’ve gone further asking about where your clients are in their speaking careers now, what challenges they are currently facing, and what they’d like to achieve in a year from now. Now is when the rubber hits the road. You have to deliver on your implied promise of a solution to get on 100 stages in 1 year.

This is when you can offer insights into the problem. Tips and tricks to findings stages, creating talk titles that get attention, contract tips, etc. You can offer your insights as a thank you gift for having the conversation with you. It’s a nice way to appreciate the time your ideal clients just spent with you, even though it was likely only 60 seconds.

People will be amazed that you were able to give such personalized insights to them and appreciative that there are some “insider tips” that they have to help them immediately with the problem they want to solve.

Step 4. Use questions to invite ideal clients into your community

Now that you have demonstrated that you understand the problem your ideal clients are struggling with, engaged them in a conversation about their unique situation, and offered them your insights on how they can proceed with some tips and tricks now you have built the know, like, and trust factor to a point that you can invite them to the next step of working with you.

The last step is the cherry on top of the sundae and it’s the easiest one to complete. Simply invite your ideal clients to continue the conversation with you where you can go more in-depth with the solutions you have to the problem they are solving. This can be an invitation to your 1:1 call, your webinar, your masterclass, or even your sales page. Whatever that logical next step is for learning more about the solutions you offer.

For example, let’s say that as a money mindset coach you’ve had a conversation through the questions you’ve asked about what is keeping your ideal clients stuck at a certain revenue level and you’ve given some insights on how to reframe the money conversation so that money can flow more freely to the business. We all know that there is more to money blocks than a few insights may fix, and you’ve created a full course on improving your money mindset to create the business of your dreams. This is when you can extend an offer to your ideal clients to learn more about what it would be like to take the course and work with you.

This invite comes after a conversation with them, so they are no longer “cold leads” but ideal clients you’ve already connected with and had a conversation regarding their most pressing problem. Who doesn’t want to do business with the person that takes the time to have this conversation and better understand the individual situation before ever offering a solution?

The questions you ask your clients are important for understanding their needs and helping them to see how you can help. By posing a problem that they need to solve, you can get them talking about their current situation and where they’d like to go. From there, you can offer insights into the problem as a thank-you for having the conversation with you. Finally, use questions to invite ideal clients into your community so that they can continue learning about the solutions you offer.

This all may seem like a lot of effort and a long conversation, but it can all be done in just 60 seconds with 5-8 questions within a Quiz. Quizzes are an amazing way to not only understand what your ideal clients are struggling with but also a way to engage them in a conversation, offer some value, and invite them into your community so that you can continue working with them.

If you want to attract only the best and release the rest the only question that remains is what questions will you ask your ideal clients today? Let us know in the comments below!

If you’d like to learn more about what’s the best quiz to attract your best clients you can reach out to Catharine O’Leary, aka “The Quiz Queen”, at Better still take the quiz to learn what’s the best quiz to attract your best clients at

Catharine O’Leary

Catharine O’Leary is the creator of QUIZ-alicious: An easy formula to attract your very best clients year-round…in just 60 seconds. After 25 years of writing thousands of quizzes, surveys, and assessments for fortune 100 corporations Catharine has created a process to develop quizzes that take the pain and frustration out of prospecting and create a client attraction journey that leads to profits for your business.

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