Diary of an IT Sales Expert

In this episode, James is joined by Richard Few, renowned sales expert and founder of Sales Geek. Together, they explore how the world of sales is evolving and why genuine human connection is becoming increasingly valuable for salespeople. Richard shares his journey from a traditional sales background to building Sales Geek, a fast-growing organisation dedicated to improving the sales profession a...

In this episode, James breaks down what it really takes to build a scalable sales system as we move into 2026 and beyond. Rather than chasing quick wins, he explains why sustainable growth comes from clarity, structure, and consistency across your entire sales operation. James walks through the foundational steps every business owner must get right before scaling, from clearly defining your produc...

In this final episode of 2025, James focuses on one of the biggest challenges facing sales professionals and business leaders as we head into 2026: consistently generating meetings and new opportunities. He breaks down the full journey from first contact to conversion, explaining why early conversations matter just as much as closing the deal. James shares 19 practical, daily actions designed to h...

In this reflective end-of-year episode, James looks back on 2025 — a year defined by rapid change, particularly the continued rise of artificial intelligence and its growing influence on business and everyday life. He shares key lessons, challenges, and wins from the year, while also thanking listeners for their continued support as the podcast approaches an incredible milestone of 10,000 download...

In this episode, James tackles one of the most common challenges in sales: price objections. Rather than seeing price as the problem, James explains why objections are often a symptom of something deeper, misaligned expectations, unclear value, or unanswered questions earlier in the process. He breaks down the real reasons prospects push back on price and shows how better questioning, earlier qual...

In this episode, James dives into one of the most important responsibilities of any sales leader: promoting the right people. Drawing on years of experience appointing both high-performing and underperforming sales leaders, James outlines a clear, structured framework to help you identify who is truly ready to step up. He shares eleven essential criteria that every sales leader should consider bef...

In this episode, James breaks down the strategy behind selling multiple services to the same company, one of the most effective ways to increase revenue, strengthen relationships, and boost long-term client retention. James explains why clients who buy more than one service are far more likely to stay loyal and continue growing with you. He shares the data behind customer “stickiness” and outlines...

In this episode, James tackles one of the most frustrating experiences in sales: being ghosted. When a prospect suddenly stops responding after positive early conversations, it can leave even experienced sales professionals confused and second-guessing what went wrong. James breaks down the four core reasons ghosting happens: human nature, poor questioning, missed signals, and the energy you proje...

In this episode, James breaks down the essential steps for managing inbound sales leads, a critical part of the sales process that many professionals overlook. While inbound leads put you in a strong starting position, they are not guaranteed wins. James explains why diligence, speed, and professionalism are vital in turning these enquiries into real opportunities. He highlights the importance of...

In this episode, James tackles one of the most misunderstood parts of the sales process: the discovery call. Far too often, salespeople approach these calls with the wrong mindset, treating them as a pitch instead of what they truly are: a conversation to determine fit. James explains that a great discovery call isn’t about pushing your product or service. It’s about listening, understanding, and...

In this episode, James explores what it will take to truly stand out as we move toward 2026, a time when authenticity, connection, and creativity will matter more than ever. As artificial intelligence becomes woven into every aspect of business communication, James argues that being human is now your biggest competitive advantage. He shares why showing up authentically, by sharing your story, expe...

In this episode, James breaks down the power of proactive selling and why waiting for leads to come to you is no longer enough. Using the vivid metaphor of “swimming out to the ship,” he highlights that success in sales demands initiative, strategy, and consistency. James challenges the misconception that outbound sales is outdated, showing how a value-led approach can still generate strong result...

In this episode, James reveals what truly separates the top 1% of sales professionals from the rest. It’s not just about closing more deals; it’s about mindset, discipline, and the ability to build long-term influence. James explains that while 80% of salespeople focus on their own targets, the elite few concentrate on creating value for their clients. He explores how personal branding, strategic...

In this episode, James challenges one of the most enduring clichés in sales, the old “always be closing” mantra. He explains why this outdated approach, rooted in high-pressure tactics, no longer resonates with today’s well-informed and discerning buyers. Instead, James explores how modern sales success comes from empathy, trust, and genuine value. By focusing on understanding buyer psychology, re...

In this episode, James reflects on the true meaning of exceptional customer service, drawing on his own experiences to highlight the stark differences between perception and reality. Using a recent stay at a so-called five-star hotel and contrasting it with the world-class service at Coworth Park, he reveals how small details and personal touches can transform an ordinary experience into an unforg...

James welcomes the remarkable Gemma McGrattan to the podcast, who shares her inspiring journey of co-founding a highly successful business that grew from humble beginnings to working with prestigious brands across the UK. What started at a dining room table flourished over 17 years and ultimately attracted the attention of a global creative agency, leading to its acquisition. In this enlightening...

In this episode, James takes a moment to thank listeners for their ongoing support and feedback on the podcast. Building on that appreciation, he shares twelve actionable sales tips designed to help professionals improve their communication, build stronger client relationships, and ultimately close more deals. Each tip is practical and easy to apply, covering common pitfalls that often hinder sale...

In sales, things rarely go as planned. That’s why adaptability isn’t just a nice-to-have skill, it’s essential. In this episode, James shares why the ability to pivot in the moment is one of the most powerful tools in a salesperson’s toolkit. Drawing on personal stories, including lessons learned from military training, James shows how adaptability can mean the difference between landing the deal...

What does the world’s most famous tennis tournament have to do with sales? A lot more than you might think. Fresh from a visit to Wimbledon, James shares the powerful lessons every sales professional can take from the Championships. From world-class branding to premium pricing and the mindset of elite athletes, Wimbledon isn’t just about tennis; it’s a masterclass in marketing, value, and dedicati...

Should you ever give up on a prospect? It’s a tough question, but one every sales professional has to face. In this episode, James digs into the balance between persistence and practicality. While following up is a vital part of winning new business, there are times when pushing harder just isn’t worth it. James explains how to spot the red flags that show a prospect doesn’t value what you offer,...

As James hits the milestone of his 50th birthday, he’s taking a moment to look back and share the 50 lessons that have shaped his career, his business, and his life. From the early days of learning the sales ropes to leading a successful business, these lessons are packed with hard-won insights, practical wisdom, and a few personal stories along the way. You’ll hear about the importance of finding...

Why do some businesses smash their goals while others seem stuck in neutral? In this episode, James breaks down the seven key differences between companies that thrive and those that struggle to get off the ground. From the mindset of the leadership team to the systems that keep things running smoothly, James reveals the patterns he’s seen time and time again in businesses that achieve remarkable...

In a crowded marketplace, being “good” isn’t enough; you’ve got to be different. In this episode, James dives into one of the most critical (and overlooked) parts of successful selling: your Unique Selling Proposition (USP) . Sharing a personal story from his very first business, where he secured funding in a highly competitive industry, James reveals how having a clear USP helped him stand out wh...

Ever wondered what a typical week looks like for a sales trainer who’s still in the trenches ? In this episode, James gives you an honest, behind-the-scenes look at how he structures his sales week, from lead generation and client calls to content creation and strategy planning. Sparked by a throwaway comment that assumed sales trainers are just failed salespeople, James sets the record straight a...

If there’s one thing that separates average salespeople from great ones, it’s this: follow-up. In this episode, James dives into one of the most overlooked yet most powerful elements in sales. Too many professionals give up after one or two touches, worried they’ll come across as pushy or annoying. But the truth? Most deals are done between the fifth and twelfth interaction. James unpacks the mind...