What every leader should know before sending people to training

Executive overview

Training is one of many development tools, yet leaders routinely reach for it when the real problem lies elsewhere — in compensation structures, territory assignments, or role design. When training is the right answer, most of its value is lost before anyone enters the room: employees show up without knowing why they're there, and return to jobs that give them no chance to apply what they learned.

The episode lays out a practical framework covering when training is (and isn't) the right intervention, how to prepare employees beforehand, what leaders must do during and after training, and how leaders themselves can be powerful developers of their people.

Training fails not because of bad content, but because leaders skip the conversations and planning that make it stick.

When training is the right intervention

• Training fits three scenarios: building new knowledge, developing new skills, or learning to apply existing knowledge and skills in a new context.
• A seasoned salesperson facing a new product may need only knowledge, not skill-building.
• An MBA graduate with strong skills may need help applying them in a real workplace culture.
• Before committing to training, map the actual performance gap — compensation, territory design, or management structure may be the real cause.
• A sales team performing poorly was found, after 10–12 weeks of assessment, to have a structural compensation and territory problem — training would have fixed nothing.

How to prepare employees before training

• Never let training appear as a surprise on someone's calendar — it creates resentment before the first session begins.
• Have a direct conversation about why this training was chosen and what it is meant to do for the employee's career, not just the team's needs.
• Employees who understand the personal development rationale arrive engaged; those who don't understand why they're there become a problem for the facilitator to manage.
• Get the employee's buy-in; even mandatory training lands better when the employee can connect it to their own goals.
• A 10-minute conversation at enrollment is enough — it does not need to be lengthy, just intentional.
• Ask the training provider in advance whether participants are volunteers or assigned; the facilitation approach differs significantly between the two.

Common mistakes leaders make during and after training

• Treating training time as additional to a 40-hour week instead of part of the job — employees should not be expected to catch up on all their normal work on top of attending training.
• Failing to plan for immediate application: skills not used within a short window after training are lost.
• Rolling out training months before the new system or process goes live guarantees employees will forget everything by go-live.
• The gap between learning and application must be short; the longer the gap, the smaller the return on investment.

How to reinforce learning after training

• The primary method: create real opportunities to practice the new skill immediately — even if the employee "helps" with work the leader could do faster alone.
• Shadowing and ride-alongs work when the employee lacks formal responsibility for a task but needs the practice context.
• When application is genuinely delayed, have the employee teach or present what they learned to teammates — teaching reinforces retention better than passive review.
• Plan the post-training application before the training begins, not after.

Leaders as developers: the overlooked advantage

• Leaders consistently underestimate their own value as trainers and developers.
• Administrative work that could be delegated is often hoarded because it feels faster to do it alone — this calculation ignores the compounding return of developing someone else.
• The math: an hour spent teaching a direct report a repeatable task pays back within a few repetitions; the short-term cost is real, the long-term gain is larger.
• Bringing a team member into work the leader would otherwise do alone — even slowly — simultaneously gets the work done and develops the person.
• Few leaders formally budget weekly time for people development; those who do build stronger teams and create a lasting impact on careers.
• Slow down to speed up: accepting temporary inefficiency during teaching produces lasting capability gains.

Delegation as a development tool

• Leaders avoid delegation for two reasons: not wanting to invest the teaching time, and not wanting to lose control of quality.
• Both reasons ignore the development obligation that comes with a leadership role.
• Even if a task cannot be permanently delegated, walking a direct report through it builds resilience, shared understanding, and backup capacity.
• The leader who says "I can do this in 20 minutes and it would take an hour to teach you" is optimising for today at the cost of every future week.

What great coaching and mentoring actually look like

• The best coaches and mentors rarely label themselves as such — they are simply people who genuinely care about others reaching their potential.
• Effective development relationships often emerge naturally from working alongside someone, not from formal structures.
• Mutual coaching — where both parties teach and learn from each other — can be more effective than a fixed mentor/mentee hierarchy.
• Humility in the senior party is the enabling condition: a willingness to receive feedback and be seen as a learner, not just an expert.

The two things that matter most

• Dialogue: before, during, and after training — about purpose, progress, and application.
• Time: a consistent, intentional weekly investment in people development, not a one-off event.
• Leaders who build both habits develop people who perform better, advance further, and carry the impact of that leadership well beyond the time they spend together.