Diary of an IT Sales Expert

Hosted by James White

Business Entrepreneurship

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Episodes

180

Latest episode

Aug 2026

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About the show

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/

Listen to episodes

60 recent

August 19, 202627 min

The Right (And wrong ways) To Handle Competitors In Sales

In this episode, we tackle a challenging sales scenario: how to effectively sell against an incumbent or competitor MSP that your prospect already likes. Learn how to qualify the relationship early, stay in control of the sales process, and highlight your unique value without criticizing the competition Chapters 00:13 - Selling against a liked or incumbent MSP competitor. 01:40 - Qualifying the opportunity and understanding relationship dynamics. 05:42 - Asking open-ended qualifying questions. 06:21 - Discovering why a prospect is exploring options without criticizing competitors. 08:48 - Acknowledging competitor strengths while highlighting your unique future vision. 11:08 - Embracing the idea of not being the right fit to build trust. 12:00 - Focusing on future security and productivity trends to give a reason to change. 16:13 - Using third-party articles to reinforce your value. 17:06 - Addressing the psychology behind human resistance to change. 20:53 - Focusing on the core drivers of buying: problems and desires. 21:24 - Explaining the customer onboarding journey and the four phases of sales. 23:49 - Walking away early from low-chance deals to save time. 25:00 - Inspirational closing story about John Parry's charity walk. -------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos!Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

August 12, 202624 min

How To Know Which Clients Your MSP Should Walk away from

Join me as I discuss how to identify which Clients your MSP Business should consider walking away from, focus on profitability, treatment of your team and alignment with your business model. Chapters 00:59 – The "BMW" client acronym. 03:01 – Sign 1: Mistreating your team. 04:39 – Sign 2: Low profitability vs. high support costs. 06:08 – High pain vs. high profit framework. 07:43 - Sign 3: High time and emotional energy drain. 08:56 – Sign 4: Ignoring security or tech advice. 14:52 – Sign 5: Late payments or unrealistic demands. 16:04 – Sign 6: Mismatch with your updated service model. 18:16 – Handling termination/restructuring talks. 21:57 – Revenue impacts and opportunity costs. 22:24 – Inspirational closing story. ---------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos! Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

August 5, 202615 min

Should MSP Founders ever stop selling personally

In this episode, we address a crucial question for Managed Service Provider (MSP) owners: Should you completely step away from sales? While many founders dream of handing off sales entirely, the goal shouldn't be removing yourself from the process altogether , it's about removing the company's sole dependency on you. Learn why you will always be your company's best salesperson and how building a repeatable "sales engine" can scale your business and protect its valuation. Chapters 01:12 - Why founders are always the best salespeople. 01:48 - The difference between a company cheerleader and a sales bottleneck. 02:56 - How lacking a sales engine slows growth and lowers business value. 03:49 - The authority and credibility founders bring to closing deals. 05:21 - The need for structures and processes beneath the founder. 06:29 - Using trained staff to qualify leads and involving founders for big deals. 09:16 - Removing total sales dependency on the founder, not removing the founder entirely. 11:20 - How technical founders can use their experience in meetings without walking away from sales. 13:46 - An inspirational story about a refugee engineering solar projects in Germany. ---------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos! Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

July 29, 202618 min

What To Do When Referrals Dry Up.

Are you relying entirely on word of mouth to grow your MSP business? In this episode we discuss why relying on referrals isn't a sustainable growth strategy and what actions you need to take when that source dries up Chapters 00:00 – Topic intro: Referrals and MSP growth. 00:41 – Defining business goals and growth limits. 02:07 – Evaluating customer satisfaction. 02:44 – Customer Happiness Score explained. 05:27 – Asking for referrals proactively. 07:24 – Implementing outreach strategies. 09:37 – Documenting sales success. 11:00 – Alternative lead gen and budgeting. 13:21 – Measuring data and the sales cycle. 16:06 – Weekly inspirational story. 17:41 – Outro and final remarks. ----------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos! Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

July 22, 202628 min

How to build an MSP that doesn't rely on you as the Founder

Does your MSP business totally rely on you? Can you take time off and know that existing customer issues are solved and more importantly new business can be brought in, WITHOUT you having to be there. Many MSP founders do NOT have this luxury. Even after many years of running their companies, the business still relies on them. Within this podcast, I outline the steps you need to take as a founder to build a team and business that can operate and grow without you. Chapters 00:41 - The core challenge of building an MSP that does not depend on the founder. 02:18 - Speaker's background running a SaaS/MSP business starting in 2005. 03:30 - Evaluating personal strengths and weaknesses (using tools like the DISC test). 05:22 - Identifying tasks and critical decisions that still rely directly on the founder. 06:41 - The importance of documenting standard operating procedures for consistency. 07:54 - Delegation vs. involvement: Learning to let go day-to-day. 08:30 - The rule of three: Automating or delegating repetitive tasks. 09:21 - 10:43: Resolving sales process issues when onboarding new salespeople. 10:43 - Cultivating a corporate culture centered around values and customer satisfaction. 12:12 - How detailed operational processes impact business valuations and M\&A due diligence. 13:51 - Empowering managers with authority and allowing them to learn from mistakes. 17:00 - Addressing sales as a core organizational weakness rather than just relying on referrals. 20:13 - Shifting expectations to build a leadership team capable of challenging decisions. 21:44 - Reframing sales for technical teams and leveraging customer service for referrals. 25:38 - Measuring business health while away and bridging operational gaps with external experts. 26:59 - Personal reflections on budget alignment failures vs. modern team autonomy. 27:57 - Inspirational story regarding domestic abuse law campaigns and closing remarks. - ---------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos! Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

July 15, 202629 min

The Best Time To Cold Call

This won't apply to many Who think that use of the..... Phone is dead. But contrary to what many think, speaking to people on the phone still works. If you do it well. It's harder than it ever was to get through for sure. But if you combine calls along with other forms of cold outreach (such as email and direct mail) then it still works. Not to sell there and then but to create enough intrigue and interest to make someone want to have another conversation. Many would say there is no good or bad time to call but over the last 6 months as I have made calls for both my business and that of some customers, some trends have appeared. All covered in this week's podcast. Links below. If of course you think I am the Devil incarnate by even suggesting people should still pick up the phone and speak to people they don't know then you won't want to listen. It's ok, I understand. I guess those inbound leads are just flying in...... 😉 Chapters 00:00 - Introduction to Cold Calling and Its Relevance 01:54 - Why MSPs Need a Consistent Sales Engine 03:49 - The Seven Methods of Outreach 04:45 - Preparing for Cold Calls: Targeting and Scripts 06:08 - Is There a Best Time to Cold Call? 08:00 - Timing Tips: When to Call for Better Chances 09:52 - Testing Different Call Times and Days 1 11:46 - Targeting Decision-Makers and Relevant Contacts 14:13 - Best Days of the Week for Cold Calling 16:02 - Avoiding Weekend Calls and When to Call During Incidents 18:05 - Using Relevant News and Events to Trigger Calls 20:05 - Measuring and Recording Call Results 22:01 - The Power of Longer Calls and Engagement 23:01 - Final Tips: Consistency, Practice, and Planning 26:07 - Conclusion and Inspirational Story ----------------------------------------------------------------------------- SUBSCRIBE and hit the ALERT button for upcoming videos! Want to know the secrets to sales growth? Sign up for my weekly newsletter to get weekly insights on how you can grow and scale your business or Sales career. https://www.jameswhite.business/newsletter-sign-up/

July 8, 202627 min

How I Manage Long Sales Cycles

If you want to close larger deals, you HAVE to be prepared for the deal to take time to complete. For many MSPs and service businesses, large deals can often take six to twelve months to close if not longer. What is critical are the actions you take in that time period to ensure your deal continues to move forward. You don't want to undo months of hard work by taking the wrong action and so in this podcast I explain the steps that I take to ensure larger and longer deals get closed. From identifying the real pain, the prospects options, building an internal champion and navigating different departments and people, this podcast will give you all you need to win high value contracts. Chapters 00:00 - Introduction to the Sales Cycle 01:59 - Common Mistakes: The Engagement Gap 03:39 - Phase 1: Effective Lead Qualification 06:31 - Qualification Methodologies: MEDDIC & BANT 07:55 - Phase 2: Identifying Decision Makers & Internal Champions 10:31 - Phase 3: Building Multi-Level Organizational Relationships 12:35 - Phase 4: Maintaining Consistent Value-Based Engagement 14:50 - Strategic Planning: Mapping the Journey with Your Prospect 16:05 - Understanding Pain, Impact, and Priority 18:23 - Using Org Charts to Predict Future Roadblocks 19:36 - The Cost of Doing Nothing: Assessing Risk 23:08 - Knowing Your Red Lines: When to Walk Away 24:51 - CRM Best Practices for "Plate Spinning" 26:02 - Inspirational Story: Rob Franks and the Laptop Donation Project 27:30 - Q&A 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.

July 1, 20261 hr 1 min

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

June 24, 202625 min

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.

June 17, 202634 min

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.