The best coaching session that my team had was when I was the Director of Inside Sales at an educational software company.  One day, out of the blue, the CEO called me to ask if he could “coach” 4 of my Inside Sales team members.  He wanted me to select two top producers and two under-performing team members.  His plan was to spend 1 hour with each Rep.

He did 3 things that made for a great learning experience for my team and a lasting impression for me, as a manager.

1. Lead by example.  The CEO started each of the sessions by making phone calls.  He wanted each team member to see how he approached a first call with decision makers.  He didn’t let any of the prospects know that he was the CEO.  He made several calls, while the Inside Rep took notes.  After the first few calls, the Inside Rep was given the opportunity to make calls.  Back and forth this process went, for the entire hour.
2. Have a goal for your session.  The goal for each team member and the CEO was to generate a meeting/ further conversation with the prospect to uncover need and interest.  The CEO threw down the gauntlet.  Who would get the most meetings, during the hour coaching session?  The CEO beat only 1 team member.
3. Make it “win-win”.  The purpose of the coaching session was to give the CEO a better understanding of the challenges that the Inside team faced, every day.  He also provided team members with insights on how they might improve their messaging and responses to questions. At the end of the coaching period, the CEO came to my office and told me that he learned a lot:
   1. He didn’t realize how difficult it was to get to decision makers on the phone and the number of dials it took to do so.
   2. The team was far more advanced and knowledgeable than he had imagined.
   3. The energy and spirit of the team was very positive and supportive.
   4. He thoroughly enjoyed the session and if time permitted, he would come back.

I asked the team members how they felt about the session.  Hands down – everyone loved it.  While, initially they were nervous, by the end they felt like they had learned from the top sales guy at the company.  They also felt appreciated and understood.

Coaching sessions should be about improving performance and upping the game.  They should motivate and thrill team members.  Establish the goal of the coaching session, lead the team by example and plan to be amazed by your team.  This will be a “win-win” process for everyone involved.