How to Choose a Sales Trainer: Strategic Investment or 1 More “Quick Fix”?

Selecting a sales trainer sounds simple enough – get a few quotes, pick the one you “fancy,” do a quick phone interview and Robert is most definitely your Uncle. Job done. But it’s not that simple.

For me, sales is the most important role in any company but, having been in sales since nineteen hundred and never you mind, I may be biased.

So here are a few checkpoints to ensure you get James Bond, not Mr Bean!

Does Your Sales Team Know Your Company’s Story?

• Can they articulate it in a compelling way that resonates with prospects?

• Do they understand how your company benefits your clients, not just what it sells?

• Can they explain your unique value proposition with confidence?

A great sales trainer won’t just teach techniques—they’ll help your team own your company’s story so they can sell with clarity, passion, and conviction.

So, before you sign off on a day rate, take the time to ask yourself:

• What frustrations do you have with your sales?

• What are they doing well, and what must they improve?

• Where do you want them to be in three months, six months, three years?

Your sales training should align with your business strategy and equip your team with modern, effective techniques.

The 7 most important considerations when choosing a Sales Trainer.

1. Do They Have Real Sales Experience?

A great sales trainer is not just a presenter reading from slides. They should have:

• Real-world sales experience—they’ve closed deals, built relationships, and handled objections.

• A track record of success in relevant industries.

• The ability to teach from experience, not just theory.

Would you trust a football coach who has never played professionally? Then why trust a sales trainer who has never actually sold?

2. Are They Focused on Long-Term Results?

How committed are you to sales training? Is this a one-day, hit-and-run session, or a strategic investment to elevate your team’s professionalism and performance?

Instant red card for anyone who just sends over a day rate and generic agenda is this how you want your salespeople to treat your clients? Or do you want them to build relationships, add value, and understand real customer needs?

3. Will They Let Your Sales Team Fail in the Room to Succeed in the Field?

Real learning happens when salespeople are pushed outside their comfort zone. The best trainers:

• Create safe failure environments where salespeople can make mistakes and learn from them.

• Simulate high-pressure situations so they’re prepared for the real world.

• Deliver constructive feedback that builds confidence and skill.

Sales isn’t learned through theory – it’s learned through doing, failing, refining. Your trainer should embrace that.

4. Do They Use Multi-Media Tools to Demonstrate Sales Excellence?

Role-playing exercises are cringeworthy and so last century. The best trainers will use media to illustrate brilliant sales behaviours – e.g. Hollywood movie scenes:

• The Wolf of Wall Street – Aerotyne Phone Call: Teaches the importance of being an outstanding communicator.

• The Pursuit of Happyness – Cold Calling: Demonstrates the power of resilience, efficiency, and emotional intelligence.

• The Godfather – Sollozzo’s Pitch: A masterclass in persuasion, in-room power dynamics, and handling objections.

A top-tier sales trainer will analyse and break down scenes like this to help your team memorably internalise great selling techniques.

5. Do They Align Training with Your Business Strategy?

Your sales training shouldn’t just “feel good.” It should align with:

• Your specific sales challenges and goals.

• The realities of your market and industry.

• The wider business strategy, ensuring long-term impact.

If your trainer doesn’t ask about these things, they’re probably delivering a one-size-fits-all training that won’t drive meaningful, enduring change.

6. Can They Actually Sell Themselves?

A sales trainer should be able to sell their own training. If they can’t:

• Personalise their approach when pitching to you,

• Demonstrate credibility with real-life examples,

• Follow up professionally,

…then how will they teach your sales team to sell effectively? A great trainer doesn’t just talk about selling—they demonstrate it at every touchpoint.

7. Are They More Than Just a Trainer?

Is your sales trainer:

• A real salesperson with proven experience?

• A motivational communicator who can engage teams?

• A modern sales strategist who understands LinkedIn, AI, and digital selling?

Or are they just someone who delivers PowerPoint slides? Sales training is too important to leave to someone who has never sold at a high level.

Conclusion: 3 Top Recommendations for How to Choose a Sales Trainer

Choosing a sales trainer is a serious investment, not a casual decision. Take the time to evaluate your options properly.

1. Prioritise real-world experience. Trainers should have a proven sales pedigree, not just a teaching background.

2. Look for engagement beyond the classroom. Ditch role-playing and use movie scenes and real-life sales scenarios instead to teach behaviours that stick.

3. Make sure the training aligns with your business strategy. Sales training should drive measurable improvement not just be a one-off event.

By taking the time to consider these factors, you’ll understand how to choose a sales trainer, ensuring your investment in sales training transforms your sales team into a high-performing, strategically aligned powerhouse.

Invest wisely and your sales team will go on to deliver enduring sales growth and your shareholders will thank you too!