The Ten Advantages Of Working With Mentors

“Sit up here with the white people!” The CEO then banged his palm on the chair next to his.

“Huh,” I said to myself. I had a quizzical look on my face.

“Sit up here with the white people!” The CEO banged his palm on the chair next to his again.

I was shocked. I had just joined the company a week ago.

It wasn’t just the CEO and I in the room. There were lots of other senior executives, including the VP of Human Resources, in the room.

They all seemed fine with the CEO’s behavior. Or maybe they were just used to it.

I’ve had all sorts of bosses over the years. I’ve never had a boss quite like that CEO.

I have had 18 different bosses (including board members and investors) during my career.

I asked myself a simple question about these 18 bosses. It’s a good exercise for you to do with your bosses too:

What are the first three things you think of when you think of each boss?

The results were interesting:

Only five of the 18 bosses have been really outstanding:

The rest were mediocre, or, like the bigot CEO, abysmal.

You can see why when you look at the words to describe each boss. I broke them into three groups:

The Mentors (5):

Boss #1: Mentor, teacher, theoretical

Boss #2: Retiring, supportive, puts his people first

Boss #3: Mentor, giving, puts his people first

Boss #4: Mentor, confidant, secretive

Boss #5: Supportive, creative, friend

The Mediocre (5):

Boss #6: Master delegator, tunnel vision, yeller

Boss #7: Too much the engineer, data driven to the extreme, indecisive

Boss #8: Bad habits, conformist, fearful

Boss #9: Hubris, common sense, fear and greed

Boss #10: Genius, insecure, unorganized, left me alone

The Disasters (8):

Boss #11: Wrong fit, power consolidator, dishonest

Boss #12: Burned-out, over his head, wimp

Boss #13: Power consolidator, egomaniac, out for himself

Boss #14: Disorganized, seat-of-the-pants, looking for martyrs

Boss #15: Dishonest, slick, no follow through

Boss #16: Out of touch, yeller, dishonest

Boss #17: Liar, super-smart, dishonest

Boss #18: Bigot, out of touch, out for himself

The takeaway is no big surprise:

You want to maximize your time with the Mentors:

Roughly one of every four people I have worked for has been great. Each one of my mentors has moved me to the next level and then some.

Here are my top 10 takeaways from working with my Mentors:

I learned a ton working with these mentors. From tactics, to strategy, to management, to life lessons - you name it, I learned it.
I worked harder working with my mentors then with any other type of boss. The mentor didn’t force me to work hard, but I wanted to work hard when I was working with a mentor.
I had more fun working with my mentors. I had a blast. I was learning a ton. The relationships were always peer-to-peer. What more could you ask for?
I felt a strong loyalty to my mentors. I would take bullets for any one of them.
I advocate for my mentors. I have been a reference for each and every one of my mentors. Sometimes they ask me to be a reference, and sometimes I just do it.
The relationship was always collaborative. I never felt like the relationship was boss-to-employee. It was always a relationship of equals. That’s great for your self-esteem.
Most of my mentors became friends outside of work. That’s as it should be. Great friendships can develop from great work relationships.
We could disagree and still respect each other. We could have and did have very healthy disagreements, but at the end of the day, there is always respect.
Mentors are helpful at every stage of your career, even as CEO. You always can use a coach, even (or especially) as a CEO. Three of the best mentors I had were when I was CEO.
Mentors teach you how to manage. Being a mentor to your employees is the best thing you can aspire to as a boss. Think about it. You want to be treated a certain way. Won't your employees want to be treated well too?

Mentors are the most important factor to my success. I owe everything to them.

You will find, if you haven’t already, that mentors are very rare. Five out of 18 bosses in my case.

I asked Blossom how many truly great bosses she has had in her career. My wife’s answer was only two out of 11, and she also described the great bosses as mentors.

I will bet the number of mentors you will have is going to be in the 20-30% range too.

Take full advantage when you are working with a mentor because the next person you work for is not likely to be one.

Did Things Work Out For Me At The Company?

Over the next three years, I learned the CEO was an equal opportunity bigot. Jews, Muslims, Blacks, and gays were frequent targets.

Why didn’t I just quit?

You’re right. I should have quit.

One day, the CEO said in a meeting, “Let’s say ‘Sieg Heil to our F ürher,’” when a German employee walked into the boardroom.

“No, the CEO didn’t just say that. Did he?” I thought to myself. “That’s the Nazi salute!”

20 sets of eyeballs were trained on me: the one Jewish person in the company.

I didn’t know what to do.

I froze.

I sat there stewing for the rest of the meeting.

I should have had the guts to quit that day. Instead I just took it.

Six months later the CEO fired me in a very public way.

It was the best thing that could happen:

I had stopped growing
I lost my self-confidence
I had no motivation
I hated going to work
I was depressed

It was the worst experience of my career: the exact opposite of being mentored.

The impact of an abysmal boss is extreme.

Yes, there are times you have to tough it out, but you need to get out as fast as you can:

Something better is out there waiting for you.

Leaving that company led me to my next thing: Becoming an Entrepreneur In Residence at a venture capital firm in San Francisco.

That led to me starting me starting my own company.

What ever happened to that abysmal CEO?

There are two great lessons here:

It is very difficult to prove bias in the workplace
Abysmal bosses make enemies and mentors build loyal followers

Somehow or other the CEO survived longer than he deserved to, but he didn't survive nearly as long as he wanted to.

The CEO’s enemies were waiting to pounce. You make a lot of enemies when you treat people poorly.

And me? I’m enjoying mentoring people and working with my mentors.

That’s the way it should be.

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