A Coach's Journal: The Anatomy of a Breakthrough With One on One Training
The Frustrating Plateau of a Rising Star
This journal is a chronicle of a transformation. It’s a story I’ve seen play out many times in my career, and it’s the reason I am so passionate about the power of true one-on-one training.
It begins with a call from a VP of Sales I’ve known for years. He’s frustrated. He has a sales engineer—let's call him Alex—who should be a top performer. Alex is technically brilliant, knows the product inside and out, and has a great work ethic. But his numbers are flat. He’s stuck in the middle of the pack, and the expensive, high-energy sales seminar the whole team attended last quarter had zero lasting impact on his performance.
The VP’s story is a classic case of the "post-seminar slump." The data on this is painfully clear: an astonishing 84% of sales training is forgotten by attendees within three months. The motivational buzz fades, the binder of notes gathers dust, and old habits return.
The company had invested in a training event, but what Alex needed was a developmental process. He didn't need more generic information; he needed targeted, expert guidance. He needed one-on-one training.
The Diagnosis - Why One on One Training Begins with Listening
Our first one on one training session with Alex was today. As with all my initial coaching calls, my primary goal was not to talk, but to listen. Group training delivers a monologue; effective coaching starts with a dialogue.
I asked Alex to walk me through his last few deals—the wins and, more importantly, the losses. We didn't focus on metrics; we focused on the conversations. What questions did he ask? How did he handle objections? When did he feel the momentum shift?
The root issue became clear within an hour. Alex was a brilliant technical expert, but he was selling like one. He was leading with product features and technical specifications, overwhelming prospects with data. He wasn't connecting the technology to the prospect's actual business problem. He was an expert presenter, but not yet a trusted advisor.
This is a nuance that a group seminar could never uncover. It’s a specific, individual roadblock that requires a personalized solution. This is the core of our engineered approach at Legacy Sales Engineering: we don't apply a template; we diagnose the specific point of failure and engineer a targeted solution. This is the fundamental power of one on one training.
The Breakthrough - From Presenting Features to Selling Value
This week, we had our breakthrough. The focus of our one on one training session was to shift Alex's entire approach from "what our product does" to "what our product does for you."
We role-played a scenario based on one of his stalled deals. I played the part of a skeptical CFO who didn't care about the tech specs; I only cared about ROI, risk mitigation, and competitive advantage.
The first time through, Alex fell back into his old habits, explaining the technical superiority of the product. I pushed back with objections: "That sounds expensive." "How does this actually save my team time?" "Your competitor is 20% cheaper."
He struggled. So, we broke it down. We worked on crafting value-based discovery questions and building a compelling ROI model based on the prospect's own data. We practiced articulating the cost of inaction—the real-world price the prospect was paying every day they didn't solve their problem.
The second time we role-played, the change was dramatic. Alex led with questions about my business challenges. He listened. He then connected his product's features directly to solving those specific problems, speaking the language of business value, not just technology.
This is the kind of deep, behavioral change that drives real results. It’s why organizations with effective sales coaching see significantly higher win rates and revenue growth. A generic online training module can tell you to "sell value," but only personalized one on one training can give you the confidence and skill to actually do it under pressure.
The Reinforcement - Integrating Skill with Process
A skill is useless if it isn't applied consistently. The greatest weakness of event-based training is the lack of a system for reinforcement. This week, our one on one training focused on embedding Alex's new skills into his daily workflow.
This is where our holistic, engineered approach becomes critical. We didn't just work on his pitch; we looked at his entire process.
Process Integration: We mapped his new value-based questioning techniques to the specific stages of his company's Sales Process. Now he has a clear blueprint for what to do and when.
Technology as a Tool: We configured this Custom CRM to prompt him with key discovery questions at the right stage and to make tracking the "cost of inaction" a standard part of his qualification process. The CRM is no longer just a database; it's an active part of his sales methodology.
By integrating the training directly into his established process and daily tools, we are turning a new skill into an ingrained habit. This is how you defeat the "forgetting curve" and ensure that the investment in one on one training produces a lasting return.
The Result - Measuring the ROI of Potential Unlocked
I had my follow-up call with Alex's VP of Sales today, three months after our coaching began. The transformation has been remarkable.
Alex is no longer stuck in the middle of the pack; he's now in the top 10% of the sales team. His average deal size has increased by 30%, and his sales cycle has shortened because he's qualifying deals more effectively on the front end.
The VP was ecstatic. He saw the initial cost of the one on one training not as an expense, but as one of the highest-ROI investments he's ever made. The data backs this up: the average ROI on effective sales training is a staggering 353% base on The Sales Collective. For every dollar invested, the company gets back over four dollars in performance.
More importantly, Alex is re-energized. He's more confident, more engaged, and is now informally mentoring some of the junior sales engineers. We didn't just fix a performance issue; we unlocked a future leader. This is also a powerful retention tool. As a landmark report from LinkedIn Learning found, 94% of employees would stay at a company longer if it invested in their career development.
Conclusion: A Final Entry on the Power of Personalized Investment
Alex's story is a powerful reminder that your people are not a monolith. Each member of your team has unique strengths and specific roadblocks. A generic, one-size-fits-all approach to training will always produce generic, one-size-fits-all results.
True growth—the kind that transforms performance and builds careers—requires a more precise, more personal, and more engineered approach. It requires one on one training. It's an investment not just in a skill, but in a person's potential. And in my experience, that is the greatest legacy a leader can build.
If you have a rising star on your team who has hit a plateau, let's talk! Contact us and let's engineer their breakthrough together.
Frequently Asked Questions (FAQs)
How is one on one training different from group team training?
Group team training is excellent for establishing a consistent, foundational methodology across an entire team. One on one training, however, is a personalized process designed to address the specific, individual roadblocks that are holding a salesperson back. It's a diagnostic and prescriptive approach that targets the unique challenges and opportunities for a single team member, leading to deeper, more lasting behavioral change.
How do you measure the success of one on one training?
Success is measured through a combination of leading and lagging indicators. Leading indicators include the adoption of new skills (observed in call reviews and role-plays) and improvements in key sales activities. Lagging indicators are the business results: increased win rates, shorter sales cycles, larger average deal sizes, and higher quota attainment. The ultimate measure is a clear and significant return on investment.
Who is the ideal candidate for one on one training?
One on one training is ideal for several profiles: the new hire who needs to ramp up quickly on a proven process, the talented mid-level performer who has hit a frustrating plateau, or the high-potential sales leader who needs to develop advanced strategic and coaching skills. It's for anyone in whom the company sees a potential for significant growth that isn't being unlocked by current methods.
Is it worth the investment compared to cheaper online courses?
While generic online courses can be useful for information transfer, they are rarely effective at creating true behavioral change. The investment in one on one training delivers a much higher ROI (averaging 353%) because it is contextual, personalized, and reinforced over time. It solves the specific problem that is costing you revenue, making it a far more strategic and financially sound investment.
How does this integrate with our existing sales process and CRM? Our coaching philosophy is built on integration. We don't teach skills in a vacuum. We work to embed the new techniques directly into your existing Sales Process and leverage your Custom CRM as a tool for reinforcement. This ensures that the training is not just a temporary lesson but becomes a permanent part of your team's daily workflow.
