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Diary of an IT Sales Expert

Diary of an IT Sales Expert

James White 174 Episodes Aug 19, 2026

The Diary of a Sales Expert podcast shares stories, ideas, mistakes, and learnings about sales success and failures. Host James White discusses the journey of selling, offering insights to help listeners improve their sales skills. The podcast also provides a scorecard for those frustrated with missing sales targets.

Episodes

The Right (And wrong ways) To Handle Competitors In Sales
The Right (And wrong ways) To Handle Competitors In Sales Aug 19, 2026 27:09 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 competitionChapters00:13 - Selling against a liked or incumbent MSP competitor.01:40 - Qualifying the oppor
How To Know Which Clients Your MSP Should Walk away from
How To Know Which Clients Your MSP Should Walk away from Aug 12, 2026 24:48 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 tim
Should MSP Founders ever stop selling personally
Should MSP Founders ever stop selling personally Aug 5, 2026 15:39 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 r
What To Do When Referrals Dry Up.
What To Do When Referrals Dry Up. Jul 29, 2026 18:29 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 e
How to build an MSP that doesn't rely on you as the Founder
How to build an MSP that doesn't rely on you as the Founder Jul 22, 2026 28:57 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
The Best Time To Cold Call
The Best Time To Cold Call Jul 15, 2026 29:31 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
How I Manage Long Sales Cycles
How I Manage Long Sales Cycles Jul 8, 2026 27:55 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 thi
Stop Pitching, Start Listening :A CEO’s Guide to Mastering Sales
Stop Pitching, Start Listening :A CEO’s Guide to Mastering Sales Jul 1, 2026 01:01:48 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.Chapters00:51 — David Brooks’ career journey from support to CEO03:17 — Early inspiration, work ethic, and family influence08:47 — Why communication became a leadership strength14:15 — Sales training
The Sales Advice That Sounds Right But Doesn't Work
The Sales Advice That Sounds Right But Doesn't Work Jun 24, 2026 25:22 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 d
Why Your Sales Hires Fail As An MSP And How To Fix It
Why Your Sales Hires Fail As An MSP And How To Fix It Jun 17, 2026 34:33 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 7 Hard Truths About MSP Growth
The 7 Hard Truths About MSP Growth Jun 10, 2026 31:18 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 Sca
5 amazing gains when you NICHE down & a BIG update about the Podcast
5 amazing gains when you NICHE down & a BIG update about the Podcast Jun 3, 2026 26:00 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

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