Diary of an IT Sales Expert

James White
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  • Entrepreneurship
  • Updated Weekly

The Diary of a Sales Expert podcast is all about sales success and sales failures and the whole journey around sales and selling. In the podcast share stories, ideas, mistakes, and learnings to help ensure you can become better at selling. If you would like to find out more visit my website: https://jameswhite.business/ Frustrated at missing your sales targets? Take my scorecard to find out why this is. https://www.missingsalestargets.com/

  1. 3d ago

    Stop Pitching, Start Listening :A CEO’s Guide to Mastering Sales

    In this week's episode James White sits down with David Brooks as they discuss organizational politics, leadership transparency, and how openness can mitigate political challenges within organizations. Chapters 00:51 — David Brooks’ career journey from support to CEO 03:17 — Early inspiration, work ethic, and family influence 08:47 — Why communication became a leadership strength 14:15 — Sales training, role play, and learning by practice 16:09 — Selling outcomes, not just technology 19:55 — Common sales mistakes in tech 22:11 — Selling to CEOs and getting through the door 25:23 — Why niche focus matters in IT services 29:06 — Sales engine, forecasting, and business growth 35:46 — Building and leading the right team 38:06 — Handling politics with openness and honesty 44:48 — Advice for scaling from small to bigger business 51:42 — Pricing pressure in education and premium positioning 54:55 — Work-life balance as a CEO 58:28 — Final advice: stay close to customers and pay attention to AI CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review

    1h 2m

  2. Jun 24

    The Sales Advice That Sounds Right But Doesn't Work

    In this episode, I challenge conventional sales advice, arguing that a focus on "pitching" is often what kills deals. Drawing from experiences with Managed Service Providers (MSPs), the discussion centers on why shifting from a "selfish" sales mindset to a curious, problem-solving approach is critical for success in today’s market. Chapters 00:00 - Introduction: Sales advice that sounds right but doesn't work. 01:33 - Dispelling the myth of the traditional sales pitch. 02:40 - The power of intention: Understanding and listening to the customer. 03:04 - Case Study: Why focus on the customer's agenda over your sales goals. 06:18 - The LAPS Model: Listen, Ask, Probe, Summarize. 09:24 - Positioning: Why being a problem solver beats being a "salesperson". 11:29 - Mastering curiosity and effective questioning. 14:05 - Avoiding the "Pitch Trap": How to handle requests for company history. 17:12 - Powerful discovery questions for current situations and budgets. 20:38 - The "One Question" for sales success and protecting your reputation. 23:00 - Inspirational Story: Salman Khan and the founding of Khan Academy. 24:20 - Podcast wrap-up and final sign-off. CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    25 min

  3. Jun 17

    Why Your Sales Hires Fail As An MSP And How To Fix It

    Many MSP and IT service business owners find themselves in a cycle of hiring a salesperson only for the role to fail within months. In this episode, we dig into the eight critical reasons why these hires don't work out from expecting a new hire to have a founder's drive to failing to provide a documented sales blueprint. Chapters 00:00 - Introduction: Why your new sales hire didn't work out 01:17 - The "25K Experiment": The true cost of a failed hire 03:27 - Reason 1: Expecting them to be exactly like the founder 07:16 - Reason 2: Ignoring personality differences and DISC profiles 10:52 - Reason 3: Not giving the new hire enough time (4-6 month minimum) 14:07 - Reason 4: Failing to provide a documented sales blueprint 16:52 - Reason 5: Poor alignment between sales and marketing 18:37 - Reason 6: Lack of training, mentoring, and support 21:59 - Reason 7: Weak or uninspiring incentive and commission plans 27:06 - Reason 8: No clear, consistent technical stack or offering 28:16 - How to fix it: Focusing on your "sweet spot" audience 29:26 - Building a plan for growth and a sales engine 31:48 - Inspirational Story: Aron Ralston's survival CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    35 min

  4. Jun 10

    The 7 Hard Truths About MSP Growth

    There are 7 Key components of #salesgrowth for MSPs and IT service providers Each has a key role in allowing good companies to scale and become great Do you agree with the 7? Especially point number 2? Have a listen and tell me I'm wrong Chapters 00:00 - Introduction to the 7 Hard Truths about MSP Growth 02:07 - Technical Brilliance vs. Soft Skills and Sales Engines 05:38 - Bespoke Setups Kill Scalability 09:34 - Founders as the Biggest Bottleneck 13:25 - Growth Requires Capital Investment in People and Systems 17:20 - A Niche Beats a Generalist 21:52 - Lack of a Structured, Repeatable Sales Process 25:04 - Sales Cycles in the MSP Space are Long 29:11 - Inspirational Story: Ann Makosinski and the Hollow Flashlight 30:21 - Closing Thoughts and "Eat or Be Eaten" Ethos CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    31 min

  5. Jun 3

    5 amazing gains when you NICHE down & a BIG update about the Podcast

    For years, I've given customers advice on achieving sales success, but during all that time, I wasn't heeding my own advice. I thought I was different. I enjoyed being different. Speaking to people from all over the world about their respective sales challenges gave me a buzz and of course so many of the fundamentals of sales and winning business are the same. But I was not being true to myself And I was also not going to hit an objective I had set for myself WITHOUT making some changes. I had to start drinking my own champagne. Which is what I am now going to do. All shared in this week's podcast episode. Trust me, its worth 20 mins of your time. There are 5 GAME changing reasons why. Chapters 00:00 - Introduction to Personal Change 02:55 - Focusing on a Niche Market 05:46 - Understanding Your Audience 09:08 - The Importance of Relevance 11:56 - Becoming Known for Something 15:02 - Training and Standard Operating Procedures 17:50 - Scaling Your Business 21:02 - Conclusion and Inspirational Story CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    26 min

  6. May 27

    How To Manage Different Personality Types

    James White shares insights on managing different personality types in sales and business, emphasizing understanding, communication, and consistency to build effective relationships and achieve success. Chapters 00:00 Understanding Personality Types in Management 09:49 The Importance of Communication and Relationships 20:07 Managing Emotions and Reactions 24:05 Inspirational Stories and Final Thoughts CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    27 min

  7. May 20

    Lost It All To Multi Millionaire - Andrew Scott's Inspirational Story

    Andrew Scott shares his inspiring journey from early struggles in Belfast to building multi-million pound businesses, overcoming setbacks, and fostering an entrepreneurial spirit. This episode offers practical frameworks, insights on resilience, and tips for growth and success. Chapters 00:00 - From Ireland to Opportunity: Andrew's Journey 05:53 - The Power of Hard Work and Learning 11:53 - Turning Around Distressed Businesses 17:57 - The Importance of Metrics in Business 24:03 - Resilience and Rebuilding After Failure 25:41 - Strategic Planning and Operational Growth 26:59 - The Journey of Scaling a Business 27:57 - Overcoming Imposter Syndrome 30:35 - Celebrating Failure as a Stepping Stone 34:29 - Reviving the Entrepreneurial Spirit 38:21 - The Importance of Experimentation 40:08 - The Emotional Journey of Selling a Business 43:49 - Inspiring Future Entrepreneurs CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review. Guest links Linkedin - https://www.linkedin.com/in/andrewscottgb/ Website - andrewscott.bio

    48 min

  8. May 13

    How To Raise Prices Without Losing Customers

    In this episode, James White Sales shares expert strategies on how to raise prices effectively without losing customers. He covers market insights, customer segmentation, communication tactics, and psychological framing to help businesses navigate price increases confidently. Key topics : Pricing strategies during market changes, Customer segmentation for price increases & Communication techniques for price hikes Chapters : 00:00 Introduction and Gratitude 00:57 Understanding Price Increases 04:59 Customer Segmentation for Pricing 10:39 Framing the Price Increase Conversation 12:34 Linking Price Increases to Added Value 14:02 Strategies for Effective Price Increases 18:15 Communicating Value and Confidence 20:50 Knowing When to Walk Away 22:44 Final Thoughts on Pricing and Value CTA Sales shouldn't feel like guesswork. Get clear, proven tactics delivered weekly — no fluff, just results. If you want to close more and stress less, this is for you. 👉 Subscribe here: https://www.jameswhite.business/newsletter-sign-up/ Enjoy the podcast? We’d love to hear from you! Email hello@jameswhite.business to suggest topics for future episodes. If you’ve enjoyed the podcast, we’d also really appreciate a review.

    28 min
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About

The Diary of a Sales Expert podcast is all about sales success and sales failures and the whole journey around sales and selling. In the podcast share stories, ideas, mistakes, and learnings to help ensure you can become better at selling. If you would like to find out more visit my website: https://jameswhite.business/ Frustrated at missing your sales targets? Take my scorecard to find out why this is. https://www.missingsalestargets.com/

Information

  • Creator
    James White
  • Years Active
    2023 - 2026
  • Episodes
    174
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 James White
  • Show Website
    Diary of an IT Sales Expert

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