Three critical moments for me came in the form of a generic turkey sandwich, a cup of cold coffee, and a really great pizza. After almost 15 years of developing and collaborating on mentoring programs, I look back on these three moments as some of the best lessons I have ever learned about mentoring.

Moment Number 1: Mentors and Sandwiches That Both Needed Some Help 

Early in my career, a top salesperson in a large organization invited me along to lunch, where she would be meeting her mentee for their scheduled mentoring chat. This salesperson—let’s call her Meredith—was one of the highest-rated mentors in a well-established and highly structured program. Her mentee, whom we will call Ben, had joined the company a few months earlier. They had been meeting twice a month since he’d been hired.

Once we had a table and our (mediocre) food, Meredith started the conversation with some small talk: “How was your weekend? Did you make it out to see your parents? Are you still planning to head to Cancun next month? Did you catch the game?” Now, I was there to observe a top-notch mentor, so I was eager for the real mentoring conversation to start. But it never really did. I spent about 45 minutes listening to polite chatter and picking at my bland sub. The conversation was like my sandwich: rushed and underwhelming.

Meredith and Ben were building a great social relationship, but neither of them had a goal or a plan for turning it into a developmental partnership. Meredith, to her credit, was great at warming up her mentees and building lasting friendships—but she didn’t have the first idea about how to drive someone toward targeted growth. Ben, like Meredith’s previous mentees, was satisfied with a lunch buddy and didn’t push for anything further.

I would love to give you a resolution to Ben and Meredith’s story, but the truth is, I’m not sure how they did in the long run. I do know that neither one was ever promoted to a leadership role in the company. Without the ability to effectively diagnose and coach an employee, Meredith would not have done well in a senior leadership role. Ben, not having received the development advice he needed from Meredith, was probably one of the hundreds of employees who left the organization each year.

That day in the deli, I realized how little support and oversight mentors in a typical program receive. The success of formal mentoring programs completely hinges on the ability of mentors to guide, coach, challenge, inquire, and advocate—skills that many just don’t possess. Of all the mentors I have had the opportunity to evaluate, most do not even truly understand the root cause of a performance issue.

Although every organization, program, and mentor has a unique set of needs, here are some general tactics I have found helpful in developing mentoring skills: 

• Set precise and clear expectations from the time mentors join the program.

• Provide the criteria by which mentors will be evaluated.

• Invite mentors to participate in role plays of difficult mentoring scenarios.

• Collaborate to create an individual development plan for the mentee.

• Host occasional town hall–type opportunities for mentors to share thoughts, challenges, and ideas.

• Distribute conversation starters and ways to address performance gaps. 

I know that if Meredith had been observed sooner, provided support, and evaluated constantly, she would have left a tremendous legacy of talent development in the organization. Great mentors are the most crucial part of the formula for great mentoring programs. Failing to invest in their development is inviting failure for the entire project.