Social 333 Podcast #78: Why Do So Many Salespeople Suck and How Can They Improve?

Guest: Benjamin Dennehy ("UK's Most Hated Sales Trainer")
Host: Chris D. Bentley
Date: December 10, 2025

Episode Overview

This candid episode of the Social 333 Podcast dives headfirst into the harsh realities of sales with Benjamin Dennehy, known as the "UK’s Most Hated Sales Trainer." Host Chris Bentley and Dennehy explore why so many salespeople underperform, the root causes of mediocrity in the industry, and how individuals can break the mold to become successful sales professionals. The discussion is unfiltered, loaded with memorable moments, and offers both tough love and practical strategies for salespeople at all levels.

Key Discussion Points & Insights

1. The "Most Hated" Persona: Purpose & Origins

Benjamin Dennehy shares how he intentionally cultivated the “most hated” title as a counterpoint to the emotional neediness rampant among salespeople and trainers.

• [01:12] “I'm the UK’s most hated sales trainer. I travel the world telling salespeople why they're losers, really, and trying to stop them from being losers.”
• Sales trainers typically seek validation—Dennehy deliberately chose the opposite to detach from the need to be liked and focus on results.
• The persona (and signature style, including a red hat reminiscent of Trump’s) served both as branding and as a challenge to the ‘guru’ culture in sales training.

2. Why Most Salespeople “Suck”

• Default, not design: Most salespeople never intended to go into the profession; they end up in sales by accident, not ambition.
  • [03:29] “Virtually everybody, not everyone, say 99% of people that are in sales are there by default, not design. They didn't want this for their life.”
• Minimal Training: Becoming a “professional” often just requires product training, a CRM login, and a suit—no deep mastery.
• Order Takers vs. True Sellers:
  • Most salespeople are not selling but merely taking orders. When times get tough (e.g., economic downturns), “order takers” get exposed.
  • [05:20] “During tough times, order takers are useless. The only ones that were selling are still selling.”

3. Lack of Process, Structure, and Effort

• Winging It: Many pride themselves on improvising instead of following protocols, equating charisma or “personality” with success.
  • [05:54] “They actually see winging it as a badge of honor. It's an element of pride... No, seriously, why did we win it?”
• Aversion to Learning: Few invest time outside working hours on self-improvement (watching sales videos, practicing pitches, etc.).
  • [07:47] Chris: “I don't think any of the sales people that I hired spend any time actually watching sales videos or pitches or high ticket closes. They don't watch any of it.”
  • [07:53] Dennehy: “No. Because they don't want to be there. Why would you spend your personal time on something you don't?”

4. Confrontation Avoidance and Emotional Programming

• Most salespeople hate confrontation, avoid tough questions, and are programmed as “buyers,” not “sellers.”
  • [08:58] “It's pathetic, isn't it? Because their fear is they hate confrontation. They don't like to challenge ... They'll lose something they've never had.”
• They default to “think it over” responses—mirroring what their upbringing taught them (“sleep on it, don’t rush into anything”).
  • This deeply rooted buyer’s mindset sabotages momentum in the sales process.

5. Emotional vs. Intellectual Selling

• Buying is Emotional, Justified by Logic:
  • [14:22] “Everything we buy is 100% emotional. But there's a second part. We have to justify it intellectually.”
  • Salespeople intellectually justify rather than trigger emotional buying drivers.
  • [15:05] “They don't do that because that's hard. Getting someone to emotionally admit they want it ... you need to have both parts.”

6. Ego, Rejection, and the Sales Roller Coaster

• Many salespeople lead with ego-centric pitches and crumble in the face of rejection.
  • [16:21] “Would you go up to a stranger [at a bar] and have that exact opener? ... Why are you phoning up, talking about you? You're a loser.”
• The cyclical emotional highs and lows of sales come from lack of process, emotional neediness, and personalizing rejection.
  • [18:01] “They have a roller coaster. Because one month they do really badly, and they go home and they think, well, I'm crap, but I'm not this crap. So next month, they try harder. ... They're always up and down because there's no consistency to what they do.”

7. The Realities of Recruiting & Retention

• Most salespeople who are looking for jobs are underperformers—top salespeople don’t leave jobs where they succeed.
  • [19:11] “So anyone ... you're looking for someone to hire anyone that applies for your job is probably crap.”
• Interview test: Make candidates do “on the spot” sales calls in interviews to expose real competence under pressure.
  • [20:14] “Most salespeople interview like Tom Cruise, but turn to Mr. Bean.”

8. Advice for Aspiring Salespeople

Should you get into sales?

• [22:04] “Don't. Really don't. Yeah. Unless you actually really want to do it.”

• Sales is akin to entrepreneurship—if you can't handle running a business, it's not for you.

• Focus first on prospecting. Before seeking a sales position, test your ability to prospect—sell yourself or your service, even as a freelancer.

• Read human psychology instead of “sales books.” The skills are about understanding people, not canned scripts.

  • [23:47] “Don't read sales books. They're all bollocks. That's why I've not written one.”

• Speech therapy & communication: Work on clarity and delivery; consider Toastmasters to diversify your communication styles.

  • [24:11] “The worst piece of advice you'll ever get in sales is just be yourself. No, no, no, no, no, no, no, no. Just be yourself is the worst piece of advice ... You need to change your personality to give them the one that'll make them feel comfortable.”

9. Sales Process & Control of the Conversation

• Always be asking questions—never relinquish control of the conversation.
  • [25:27] “The job of a good salesman is to extract, not give it. And the moment you lose control is when you start answering questions.”
• Learn Transactional Analysis—understanding communication patterns is key for conversation control.

10. Why “Relationship Selling” is Overrated

• The notion of “relationships” in sales is largely a myth—loyalty ends the moment financial or practical considerations shift.
  • [34:41] “You don't have a relationship even with customers you've been with for years ... If you go to them and say, look, we're struggling, we're gonna have to put our prices up by 20%, let's just see how loyal they are.”
• Family connections are the only exception; otherwise, everyone is fair game for a conversation.

11. Practical Techniques: Pushing Away to Draw In

• Use reverse psychology—push prospects away instead of chasing them.
  • [37:32] “Your job is to push people away, not pull them. Laura, Physics says if I push something away, there's an equal and opposite force. So if I push away, there's a good chance it'll swing back.”

Notable Quotes & Memorable Moments

• “Most salespeople, if they're honest, are order takers. They're not really... we would have won the deal with a chimpanzee on roller skates sort of thing.”
  – Benjamin Dennehy [04:16]

• “If you're good at sales in your job, why would your boss let you go?”
  – Dennehy [19:00]

• “Books on psychology, though, understanding why people do what they do, study. There's a model for understanding human communication called transactional analysis. If you understand that you suddenly understand why every conversation you've ever had goes the way it goes, gives you a great amount of control.”
  – Dennehy [32:05]

• "Just be yourself is the worst piece of advice because yourself only appeals to about 20% of the population. And sometimes, you're a dick."
  – Benjamin Dennehy [24:11]

• “Selling is easy once you know what you're doing.”
  – Benjamin Dennehy [38:55]

Timestamps for Key Segments

• 01:12 – Dennehy on being “most hated”
• 03:29 – Why most people enter sales by default, not ambition
• 05:20 – Order takers collapse in tough times
• 07:53 – Why most salespeople avoid extra learning
• 08:58 – Fear of confrontation and never really “losing” deals
• 14:22 – Emotional vs. intellectual decision-making
• 18:01 – The emotional rollercoaster of the average salesperson
• 19:11 – The reality of hiring: top talent seldom applies for jobs
• 22:04 – Dennehy’s tough advice for aspiring salespeople
• 24:11 – Why “just be yourself” hurts more than helps
• 25:27 – The importance of keeping control in conversations
• 32:05 – The value of psychology and transactional analysis
• 34:41 – The myth of “relationship selling”
• 37:32 – Pushing away prospects to pull them in

Further Resources / Where to Find Benjamin Dennehy

• LinkedIn: Search “UK’s Most Hated Sales Trainer”
• Website: uksmosthatedsalestrainer.com
• Online Courses: salesmatrixcourses.com
• YouTube: Search for “UK’s Most Hated Sales Trainer”

Takeaways

This episode is a no-holds-barred critique of the sales profession’s shortcomings. Dennehy’s advice is clear:

• Don’t get into sales unless you’re truly passionate.
• Focus on prospecting, understanding psychology, and mastering communication.
• Ditch the ego, stop winging it, and always control the conversation.
• Challenge prospects, don't seek their approval, and learn to push people away.
• Relationships in sales are transactional, not genuine friendships—act accordingly.

For those ready for tough truths and tangible improvement, Dennehy’s cold, candid wisdom offers a wake-up call and a roadmap to selling the right way.