How I Mentor

“Mentoring is a process for the informal transmission of knowledge, social capital, and … support perceived by the recipient as relevant to work, career, or professional development; mentoring entails informal communication, usually face-to-face and during a sustained period of time…”   (source Wikipedia. Bozeman & Feeney)

In searching for this definition of mentoring, I also came across this article “What the Best Mentors Do”  by Anthony K. Tjan. I highly recommend reading it.

Since the writers above provide a far better definition of mentoring than I could, this post focuses on Why I mentor and How I mentor.


I mentor people for a number of reasons:

  • To pass on to others what my mentors have done for me.
  • To be of maximum service.
  • To extend kindness and generosity – which always brings positive results.

And finally, as it turns out, mentoring has been the single most rewarding activity of sales management for me. It makes me feel like I’ve accomplished something worthwhile.


Mentoring begins much earlier than you might suspect.  

If you are a manager, your people are watching you all the time.

They might not always seem to be paying attention but they are always watching to see see how you handle stress, conflicts, and challenging situations.

They are watching to see how you treat your subordinates, your superiors, your peers, your waiter, the janitor, and your family.

They are watching to assess your character – by judging your actions –  before approaching you for help.

They are seeking answers to the questions:

  • Are you someone I can admire?
  • Do you exemplify what I aspire to become?
  • Can I trust you?

How do I know this?  Because I’ve done it myself. Plus, I’ve can’t count how many times someone has said to me, “I heard you say this… and that’s why I came to talk to you.” What I thought was a casual conversation, a team meeting, or a sales presentation took on deeper meaning for someone.

So if I want opportunities to mentor, I have to earn them with my actions.

What I attempt to do is be open and approachable. I take responsibility for my failures and mistakes. I try to make things right when I have harmed someone.

I’m far from perfect, but on balance, I do the right thing more often than not. From this behavior, I have found that mentoring opportunities turn up.


How I’ve Been Approached to Mentor

I’ve never participated in a formal mentorship program.  I simply observe people at work, make myself available, and offer assistance if I think I have experience that might be helpful.

In some cases someone who reported to me or worked in less “prestigious” role than mine would ask me a question like:

  • What should I do to get promoted?
  • How would you handle this problem?
  • Is this the right career path for me?

Other times, as mentioned earlier, mentoring starts as a follow up to a conversation from a sales meeting, a presentation, or in a 1-on-1.

With the exception of employees with whom I have weekly 1-on1’s, all mentoring started on an ad-hoc, as needed basis. I’ll get asked, “Do you have a few minutes to talk?” Or “Can I run something by you?” and we go from there.

Sometimes these situations are one-offs. We have a conversation, I try to help with a specific situation, and that’s it. Other times, we may make a connection that opens the door to more conversations and ongoing mentoring. I try to make time to help anyone who shows a genuine interest and who is willing to do the work.


How I Mentor

This is surprisingly simple. There’s little difference for me in helping someone vs. mentoring someone except that mentoring may evolve into a longer term relationship.

  • Be present.  Paying attention and giving someone my total focus is critical. To do this, I close the office door, shut my laptop,  turn off my cell phone ringer, clear my schedule, and give my total focus to the person.
  • Listen intently. For me this includes taking notes, asking questions, showing curiosity, expressing concern, and probing for more details.
  • Be a calming presence. Often someone comes to me when he’s upset or wound-up about a situation. If I help him calm down and think through the problem, he usually doesn’t need my advice. He knows exactly what to do. At times, I’ve taken someone for a walk, let him have a small meltdown in my office, walked him through breathing exercises, helped him see the humor in a situation, confessed similar feelings of rage or despair, and at times have even said “you just need to suck it up and accept the situation.”
  • Offer reassurance and express confidence in him. For me, having someone I admired express confidence in my abilities worked wonders. This is one of my favorite mentoring techniques. I follow this up by helping create an action plan with clear next steps. This is where my experience with similar situations is valuable.
  • Make a connection. If I have no relevant experience, I will refer my mentee to someone who does. When possible, I make a warm introduction.
  • Provide expertise.  Notice how far down the list I’ve placed expertise. Most of the time, my role is to help someone discover his own answer.  Occasionally, I’ve had direct expertise and can provide specific recommendations.

Here are a few of my favorite mentoring experiences.


Miss Underrated was outstanding in her sales support role, but in our Type-A, male-dominated sales culture, other managers saw her as “not cut out for sales”because she was soft spoken and not in-your-face.

I wasn’t so sure about that. So I took her under my wing to help her build up her sales skills and product knowledge. At the same time, I began planting the seed among my colleagues that she was an All Star in the making.

After she’d built up her sales skills, I scheduled a 2-on-1 interview with her for an Inside Sales role on my team. During the interview, she was well prepared but we could see her struggling to give us the perfect responses. At one point, she was trying so hard, tears welled up in her eyes.

Then I said to her:

“You were a nationally ranked concert pianist. You graduated from a top tier school with honors. You even auditioned for American Idol. Then you joined our company and quickly became our favorite sales support rep. Tell us how you accomplished all this. What motivates you to succeed? “

She paused, took a deep breath and replied:

“It’s like I have this little voice that sits on my shoulder and says ‘you’re not good enough and you’ll never be good enough’ and I have to fight against that voice to prove that I am good enough.”

Almost simultaneously, both my rep and I exclaimed:

“We all have that voice! Everyone does. It’s what you do with it that matters.”

That week, I hired her. She became a strong inside rep then was promoted to field sales and then moved onto a more senior sales role with another company.


The Sergeant had been an inside rep who was promoted to Field Sales but then laid off within a year. He rejoined our company 12 months later as an Inside Sales rep once again. When I took over his team, senior management had expressed concerns that he wasn’t cut out for sales.

Once again, I wasn’t so sure about that. He had a really good handle on pipeline management & forecasting, he made great customer calls, and he maintained a ‘heads down, get my work done’ focus while avoiding company politics. As far as I could tell, his only shortcoming was that he needed someone to guide him through the corporate bureaucracy and get him recognition for his work.

That’s where I was able to help.

I told him that I wanted to groom him as my replacement. In return, I’d need his help in managing my team. He accepted the challenge. In time, he was covering for me in leadership meetings, running team meetings, and participating in strategy sessions. When I was promoted into a new position, he took over the team and they crushed it for years. Even better, I’ve been able to see him take others under his wing and do for them what I did for him.


There are many other stories I could share:

  • The Sales Manager who questioned whether management was his best career path. After working with me for a few months, he built up the courage to move to a challenging Enterprise Sales role and years later returned to management.  
  • The  Jr. Manager who met with me monthly for mentoring. With 3 years he left to run sales for a startup. He’s now the Director and grown annual revenues from under $1M to over $5M in 3 years.
  • The Career Switcher who we hired as an entry level rep despite the fact that he had 20 years of unrelated work experience. He’s now VP of Sales for another tech firm.  

I could go on and on.

But my stories are not important. What is important are the stories that you will create by extending your hand to help others.

Go out and make it happen. You’ll be glad you did.

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