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Highly Profitable LIVES

We'll teach you everything you need to know about living a profitable life as a 21st century lifestyle Entrepreneur. Curious how?

We Help Entrepreneurs Build Highly Profitable Lives.

We'll teach you everything you need to know about living a profitable life as a 21st century lifestyle Entrepreneur. Curious how?

Future Publications & Features

Future Publications & Features

Who Is Wayne Veldsman?

Wayne Veldsman, owner of Vel.Consulting and Journey To Legacy, began his career by building several digital businesses out of his college dorm room....


Wayne is an accomplished business growth strategist, success coach, and entrepreneur. He specializes in helping entrepreneurial minded individuals to grow both their mindsets and their income.


After starting his first business in 2014, Wayne successfully launched and scaled a digital marketing agency to a 7-figure valuation before deciding to exit in 2019 to move to Denver, Colorado and start chasing his passion of coaching and public speaking.


Wayne actively works with entrepreneurs and businesses who are looking to take massive action and create drastic changes in their lives.

Not Sure How To Make The Drastic Change Necessary To Live The Life Of Freedom That Comes With Being A Lifestyle Entrepreneur?

Discover the stupid simple method to growing businesses digitally on autopilot, so that you can get back to your life.

Some of Our Successful Students

Our students and clients aren't just satisfied, they're building life-changing businesses, doing what they want when they want, and living their lives chasing passion, not just profits.

Media Spotlights...

Join My Free Facebook Community!
Join my free Facebook Strategy group to connect with like-minded individuals, get access to exclusive resources and trainings, and get access to LIVE interviews from top industry leaders so you can learn directly from the best in the businesses!
Join My Free Facebook Community!
Join my free Facebook Strategy group to connect with like-minded individuals, get access to exclusive resources and trainings, and get access to LIVE interviews from top industry leaders so you can learn directly from the best in the businesses!
Products & Resources

The 3-Step Strategy To Growing Businesses Digitally

Are you an Agency Owner, Service Provider, or Entrepreneur who sells online and want your pipeline filled with 300+ appointments with your idea client every single month? Are your SERIOUS about growing your business and want to work with Wayne 1-on-1?


Launch Into Digital Entrepreneurship is a course and coaching program specifically designed to take agency owners and online service providers from manual prospecting and wondering if this is ever going to work out, to having a very specific system in place which is going to allow you to generate 20 to 30 booked appointments every single day!


You're going to get a step by step process to building out your prospecting, sales and fulfilment system, and building your sales team so that you can close clients while stepping away from your sales process.

Ready Leads Software

Price - $1,997 $97 (Limited Time Offer!)

Need Marketing Agency Clients? Let Us Take Care of the Hard Part For You! Get Pay-As-You-Go, 'Ready-To-Buy', Inbound Leads Sent Straight To Your Phone Every Day!

You'll get your own ReadyLeads Dashboard & CRM so that you can keep organised with all your leads, conversations and manage all of your automated follow up sequences with ease!


Every time we generate you a new lead interested in your marketing services, your dashboard will automatically add the new lead into your CRM, and send the new lead an SMS, email, and even automatically call you to connect you right away!

Become More Focused, Be More Productive, Burn Out Less

Price - FREE training

Want to know how to close high-ticket deals with ease by simply following a tried, tested and proven, sales script and formula?
Tired of not knowing what to say on a sales call to properly frame the call and your offer so that it sells? Want to have your potential clients selling themselves to you, rather than the other way around?
Get our Sales Masterclass training and transform your sales game so that you can close high-ticket deals on the phone like a pro!

From The Desk Of Wayne Veldsman (blogs)

business professionals engaged in a deep meaningful conversation due to their ability to ask better strong meaningful questions

The Art of Asking Better Questions

December 04, 20243 min read

Have you ever asked someone "Why did you do that?" and immediately sensed them becoming defensive? There's a good reason for that reaction, and it points to a crucial skill that many of us need to develop: the art of asking better questions.

The Problem with "Why"

Our brains are wired to react defensively to "why" questions. When someone asks us "why," it often feels like an accusation rather than a genuine inquiry. This triggering of our fight-or-flight response can shut down productive dialogue before it even begins.

Enter Calibrated Questions (*Term coined by Chris Voss of The Black Swan Group)

Calibrated questions represent a more sophisticated approach to information-gathering and problem-solving. These are thoughtfully crafted, open-ended questions that cannot be answered with a simple yes or no. But their power goes beyond just gathering information – they can actually help shape thinking and guide problem-solving processes.

The "What" and "How" Revolution

The most effective calibrated questions typically begin with "what" or "how." Consider these examples:

  • Instead of "Why aren't we meeting our goals?" try "What obstacles are you encountering in reaching these targets?"

  • Rather than "Why didn't this work?" ask "How do you envision this working more effectively?"

  • Instead of "Why did you choose this approach?" try "What factors influenced your decision-making process?"

These reformulated questions invite reflection and dialogue rather than defensiveness and justification.

The Strategic Impact

When we use calibrated questions effectively, we achieve several important objectives:

  1. We create psychological safety, allowing others to share their thoughts without feeling attacked

  2. We encourage deeper thinking and more detailed responses

  3. We empower others to participate in finding solutions

  4. We gather more accurate and useful information

The One Exception to the "Never Why" Rule

Interestingly, there is one strategic use for "why" questions: determining commitment levels early in a relationship or negotiation. The Black Swan Group calls this the "Proof of Life" question. For example, asking a potential client "Why did you choose to reach out to our company specifically?" can reveal whether you're their preferred choice or just one of many options they're considering.

Putting It Into Practice

To improve your questioning skills:

  1. Start paying attention to how often you use "why" questions and consciously replace them with "what" or "how"

  2. Practice formulating questions that require detailed responses

  3. Listen carefully to the quality of answers you receive – more detailed responses often indicate better questions

  4. Pay attention to your tone of voice – even well-crafted questions can be undermined by an accusatory tone

The Bottom Line

As Voltaire wisely noted, we should "judge a person by their questions rather than their answers." In our professional and personal lives, the ability to ask good questions is invaluable. By mastering the art of calibrated questioning, we can foster better communication, build stronger relationships, and achieve better outcomes in our interactions.

Remember: It's not just about asking questions – it's about asking the right questions in the right way.

Start practicing today, and watch how the quality of your conversations transforms.

At Journey To Legacy and the JTL Community, we focus on educational communications coaching to help you build stronger relationships and sell better. Join us and take your business and life to the next level, guaranteed.

salesactive listeningcoachingcommunications coachingquestion askingasking better questions
blog author image

Wayne Veldsman

Wayne Veldsman, owner of Vel.Consulting and Journey To Legacy is an accomplished online business growth strategist, success coach, and entrepreneur. He specializes in helping global nonprofit organizations to change the world by helping them grow both their mindsets and their NPO's revenue. After starting his first business in 2014, Wayne successfully launched and scaled a digital marketing agency to a 7-figure valuation before deciding to exit in 2019 to move to Denver, Colorado and start chasing his passion of coaching and public speaking. Wayne actively works with executive directors, entrepreneurs and businesses who are looking to take massive action and create drastic changes in their lives.

Back to Blog
Products & Resources

The 3-Step Strategy To Growing Businesses Digitally

Are you an Agency Owner, Service Provider, or Entrepreneur who sells online and want your pipeline filled with 300+ appointments with your idea client every single month? Are your SERIOUS about growing your business and want to work with Wayne 1-on-1?


Launch Into Digital Entrepreneurship is a course and coaching program specifically designed to take agency owners and online service providers from manual prospecting and wondering if this is ever going to work out, to having a very specific system in place which is going to allow you to generate 20 to 30 booked appointments every single day!


You're going to get a step by step process to building out your prospecting, sales and fulfilment system, and building your sales team so that you can close clients while stepping away from your sales process.

Ready Leads Software

Price - $1,997 $97 (Limited Time Offer!)

Need Marketing Agency Clients? Let Us Take Care of the Hard Part For You! Get Pay-As-You-Go, 'Ready-To-Buy', Inbound Leads Sent Straight To Your Phone Every Day!
You'll get your own ReadyLeads Dashboard & CRM so that you can keep organised with all your leads, conversations and manage all of your automated follow up sequences with ease!


Every time we generate you a new lead interested in your marketing services, your dashboard will automatically add the new lead into your CRM, and send the new lead an SMS, email, and even automatically call you to connect you right away!

Become More Focused, Be More Productive, Burn Out Less

Price - FREE Training

Want to know how to close high-ticket deals with ease by simply following a tried, tested and proven, sales script and formula?
Tired of not knowing what to say on a sales call to properly frame the call and your offer so that it sells? Want to have your potential clients selling themselves to you, rather than the other way around?
Get our Sales Masterclass training and transform your sales game so that you can close high-ticket deals on the phone like a pro!

From The Desk Of Wayne Veldsman (blogs)

business professionals engaged in a deep meaningful conversation due to their ability to ask better strong meaningful questions

The Art of Asking Better Questions

December 04, 20243 min read

Have you ever asked someone "Why did you do that?" and immediately sensed them becoming defensive? There's a good reason for that reaction, and it points to a crucial skill that many of us need to develop: the art of asking better questions.

The Problem with "Why"

Our brains are wired to react defensively to "why" questions. When someone asks us "why," it often feels like an accusation rather than a genuine inquiry. This triggering of our fight-or-flight response can shut down productive dialogue before it even begins.

Enter Calibrated Questions (*Term coined by Chris Voss of The Black Swan Group)

Calibrated questions represent a more sophisticated approach to information-gathering and problem-solving. These are thoughtfully crafted, open-ended questions that cannot be answered with a simple yes or no. But their power goes beyond just gathering information – they can actually help shape thinking and guide problem-solving processes.

The "What" and "How" Revolution

The most effective calibrated questions typically begin with "what" or "how." Consider these examples:

  • Instead of "Why aren't we meeting our goals?" try "What obstacles are you encountering in reaching these targets?"

  • Rather than "Why didn't this work?" ask "How do you envision this working more effectively?"

  • Instead of "Why did you choose this approach?" try "What factors influenced your decision-making process?"

These reformulated questions invite reflection and dialogue rather than defensiveness and justification.

The Strategic Impact

When we use calibrated questions effectively, we achieve several important objectives:

  1. We create psychological safety, allowing others to share their thoughts without feeling attacked

  2. We encourage deeper thinking and more detailed responses

  3. We empower others to participate in finding solutions

  4. We gather more accurate and useful information

The One Exception to the "Never Why" Rule

Interestingly, there is one strategic use for "why" questions: determining commitment levels early in a relationship or negotiation. The Black Swan Group calls this the "Proof of Life" question. For example, asking a potential client "Why did you choose to reach out to our company specifically?" can reveal whether you're their preferred choice or just one of many options they're considering.

Putting It Into Practice

To improve your questioning skills:

  1. Start paying attention to how often you use "why" questions and consciously replace them with "what" or "how"

  2. Practice formulating questions that require detailed responses

  3. Listen carefully to the quality of answers you receive – more detailed responses often indicate better questions

  4. Pay attention to your tone of voice – even well-crafted questions can be undermined by an accusatory tone

The Bottom Line

As Voltaire wisely noted, we should "judge a person by their questions rather than their answers." In our professional and personal lives, the ability to ask good questions is invaluable. By mastering the art of calibrated questioning, we can foster better communication, build stronger relationships, and achieve better outcomes in our interactions.

Remember: It's not just about asking questions – it's about asking the right questions in the right way.

Start practicing today, and watch how the quality of your conversations transforms.

At Journey To Legacy and the JTL Community, we focus on educational communications coaching to help you build stronger relationships and sell better. Join us and take your business and life to the next level, guaranteed.

salesactive listeningcoachingcommunications coachingquestion askingasking better questions
blog author image

Wayne Veldsman

Wayne Veldsman, owner of Vel.Consulting and Journey To Legacy is an accomplished online business growth strategist, success coach, and entrepreneur. He specializes in helping global nonprofit organizations to change the world by helping them grow both their mindsets and their NPO's revenue. After starting his first business in 2014, Wayne successfully launched and scaled a digital marketing agency to a 7-figure valuation before deciding to exit in 2019 to move to Denver, Colorado and start chasing his passion of coaching and public speaking. Wayne actively works with executive directors, entrepreneurs and businesses who are looking to take massive action and create drastic changes in their lives.

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Need help? Email our support team at: wayne@vel.consulting