5 Reasons Sales Pitch Training is So Hard

1. The "One-and-Done" Event Mentality

The single biggest reason training fails to stick is that it's treated as a one-time event (a two-day workshop, an annual sales kick-off, etc.), not an ongoing process.

• No Habit Formation: Sales is a performance skill, like playing a sport. You can't master handling an objection by hearing a lecture; you need immediate, repeated practice and feedback. A one-off event inspires, but it doesn't rewire habits.

• The Forgetting Curve: Research shows that salespeople typically forget 50% to 84% of what they learned in training within 90 days if there is no systematic reinforcement.
  
  

2. Lack of Contextual Relevance (Not Tied to Real Deals)

Sales reps struggle to connect theoretical content with the chaos of their actual sales calls.

• Too Much Theory, Not Enough "How": Training often focuses on what the sales methodology is (e.g., "Always find the economic buyer") but not how to execute it effectively in a live call (e.g., "Say exactly this question to uncover the economic buyer").

• Generic Content: A new rep needs help with prospecting, while a top performer needs advanced negotiation tactics. A one-size-fits-all training program alienates the top performers as a waste of time and overwhelms the new reps.
  
  

3. Missing Manager Reinforcement and Accountability due to Lack of Time

Training can only succeed if the sales manager is equipped to champion the new skills.

• Managers Are Coaches, Not Police: Too often, managers are not trained on how to coach the new methodology. They revert to focusing only on metrics and deals (what the rep is doing) rather than behaviours and skills (how the rep is doing it).

• No Accountability: If a rep attends training but is never held accountable for using the new pitch or discovery questions, they quickly revert to their old, comfortable habits—even if those habits are less effective.
  
  

4. Salespeople Have No Time

Sales reps are driven by daily activities and immediate quotas. Pulling them off the phone for training creates resistance.

• Missed Commission: Reps view time spent in a classroom as time they are not selling, which directly impacts their commissions. This creates low engagement and a sense of resentment.

• Information Overload: Trying to cram too much product knowledge, CRM processes, and soft skills into a short session leads to cognitive fatigue, and the rep leaves feeling overwhelmed, not empowered.
  
  

5. Training Isn't Always the Solution

Sometimes, sales training is misdiagnosed as the cure for a deeper organizational problem.

• Hiring Problem: No amount of training can fix a fundamental mismatch between the individual's core attributes (drive, resilience) and the sales role.

• Process/Systemic Problem: If the CRM is clunky, the compensation plan is confusing, or the lead quality is poor, training on new closing techniques will not solve the underlying issue.
  
  

So how do you UPSKILL your team:

Systemise Upskilling into

a Continuous Process…

To overcome these five persistent challenges, the key is to stop viewing coaching as a standalone, sporadic event and instead systemise it as an integral, automated part of the sales workflow, just like your CRM updates or forecasting. (we automate that too)

This means building a continuous coaching framework that:

1. Easy to apply: Support must happen at the point of friction, in pitch. Integrate guidance directly into the rep's workflow, providing prescriptive advice (e.g., "Ask this question now") exactly when a challenge arises. This ensures the new methodology is applied correctly in a real deal, instantly converting knowledge into practiced behaviour.
   
   

2. Delivers Contextual Guidance: Offers prescriptive, real-time feedback and advice directly within the live sales call or meeting workflow ("Say this now").
   
   

3. Empower Sales Managers: Equip managers with specific, easy-to-use tools and playbooks to coach behaviours, not just metrics, without adding significant time to their busy schedules.
   
   

4. Empower Sellers: Give the team the tools they need to help improve but in a positive and proactive way rather than the negative connotations of previous approaches. 
   
   

5. Create Automatic Accountability: Embeds the new skill usage directly into performance metrics and manager check-ins, making the adoption of new pitches and methodologies non-negotiable.