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Should Your Mentor Join The Board? – It’s… It’s Complicated

“Trust your own instinct. Your mistakes might as well be your own, instead of someone else’s.” — Billy Wilder

The question of who you should trust when it comes to sitting on your board of directors is a tricky one.

Recently I was asked whether I thought that one should bring a mentor onboard. This person had 20+ years of experience in tech, been a CEO, and was currently retired.

Here’s what I told them.

Look, it’s really hard to tell. It could be a great idea, a mediocre idea, or a really bad idea. Only time can tell for sure.

But what I would advise you to do is to put yourself in as good a place as possible to ensure that you have a good outcome regardless of whether you choose to bring your mentor on board or not.

Part of that is understanding the dynamics of influence and power. While aspirational books like “Start With Why” by Simon Sinek might be good for making sure you’re clear on where you want to go, there’s a bit of a darker side to it as well.

To help balance this out you might want to check out books like “Leadership BS” by Jeffrey Pfeffer. Some might even call this outlook Machiavellian.

Leadership BS

The “BS” isn’t short for “Belieavble Stuff”.

However, while consulting businesses and startups in various fields I’ve seen that both approaches are equally as valid and valuable.

Understanding that an optimistic view helps us keep our eyes on the bigger picture is great, but we also need to look at the seedy underbelly of how some people play power games.

There are two excerpts I’d like you to read from Pfeffer’s “Leadership BS”:

A few years ago, Bob, the CEO of a private, venture-backed human capital software company, invited me to serve on the board of directors as the company began a transition to a new product platform and sought to increase its growth rate and profitability.

Not long after I joined the board, in the midst of an upgrading in management talent, the CEO hired a new chief financial officer, Chris. Chris was an ambitious, hardworking, articulate individual who had big plans for the company — and himself. Chris asked Bob to make him chief operating officer.

Bob agreed. Chris asked to join the board of directors. Bob agreed. I could see what was coming next, so I called Bob and said, “Chris is after your job.” Bob’s reply was that he was only interested in what was best for the company, would not stoop to playing politics, and thought that the board had seen his level of competence and integrity and would do the right thing.

You can guess how this story ended — Bob’s gone, Chris is the CEO.

What was interesting was the conference call in which the board discussed the moves. Although there was much agreement that Chris’s behavior had been inappropriate and harmful to the company, there was little support for Bob.

If he was not going to put up a fight, no one was going to pick up the cudgel on his behalf. People who are complicit in their own beheading don’t garner much sympathy or support. Taking care of yourself sometimes means acting in ways that may seem selfish.

A woman who worked in a nonprofit organization valued collaboration — so much so that she failed to press an advantage in gaining influence over an important strategic planning exercise:

The executive director asked me to set up some time with her to discuss the plans for the strategic planning session. I knew that if I alone were the one to have this initial meeting with her, I would be the main person involved in setting the direction of the project and would be viewed as the key point person; I would be the leader and my colleague would be there to help get the work done.

I wrestled with whether or not I could actually just schedule the meeting without my colleague, but I couldn’t bring myself to do it, despite the voice in my head saying it was all right. This is an indication for me of the areas where I am most challenged in acquiring power.

One wonders if her colleague would have been as considerate. And remember, in hierarchical settings, colleagues are also competitors for promotions and status. It’s not just that the world is not always fair so you should stop counting on the triumph of your merit.

People align with who they think is going to win. If you don’t stand up for yourself and actively promote your own interests, few will be willing to be on your side.

Since observers will see you as not trying to triumph and therefore losing, they will either not join you side or desert you, making your organizational demise more certain.Therefore, although self-promotion and fighting for your interests can seem unattractive, the alternative scenario is invariably much worse.

I’m not saying that this scenario is all that likely to play out in your case. But being aware of its potential will prepare you to handle it better than you would have if you were blindsided by it.


Sometimes you might see it coming from a mile away.

And even if you trust your mentor to back you up, there might be others vying for your position, or influencing you (or your mentor) in ways that are beneficial for them, but not so much for you.

Here’s a simple truth: the higher you rise and the more powerful the position you occupy, the greater the number of people who will want your job. Consequently, holding a position of great power creates a problem: who do you trust?

Some people will be seeking to create an opportunity for themselves through your downfall, but they won’t be forthcoming about what they are doing. Some people will be trying to curry favor with you by telling you what they think you want to hear so you will like them and help them advance. And some people will be doing both.

Gary Loveman, the former Harvard Business School professor who is now the CEO of Harrah’s Entertainment, commented that the higher you rise in an organization, the more people are going to tell you that you are right. This leads to an absence of critical thought and makes it difficul for senior leaders to get the truth — a problem both for the company and its leaders, as you can’t address problems if you don’t know about them.

Loveman tried to overcome this problem by regularly and publicly admitting the mistakes he made so that others would be encouraged to admit where they had messed up too. He also placed a lot of emphasis on the process by which decisions got made — particularly, the use of data and analytics — and almost no emphasis on who was making the decision. Gary was conscious of the tendency for people in power to become deeply self-righteous and believe their own hype.

This problem is difficult to overcome as it plays into our natural tendency to want to think highly of ourselves, but Loveman tried to overcome this tendency by seeking the opinions of outsiders with no stake in Harrah’s and by encouraging open debate and critical self-reflection within the company. Loveman’s success at Harrah’s and his position as a leading executive in the gaming industry insulated him, to some extent, from coup attempts. But no one in a position of power is completely immune from palace revolts.

Patricia Seeman, a Swiss executive coach and adviser to numerous high-ranking executives, particularly in the financial services industry, told me that in the typical senior management team, all the people reporting to the CEO believe they could hold the CEO position, many think they could do better than the incumbent, and most direct reports aspire to their boss’s job.

Some people are going to be willing to take their turn and hope that they will be chosen when the incumbent steps down, but others will be more proactive in their efforts to move up.

Therefore, for CEOs to survive in their jobs, they need to be able to discern who is undermining them and be tough enough to remove those people before they themselves lose the power struggle. What’s true for CEOs is also true for other senior-level executives with ambitious subordinates.

Ross Johnson, formerly CEO of Nabisco, is justly famous for his role in the first huge leveraged buyout, the RJR Nabisco transaction described so well in the book Barbarians at the Gate.

But where Johnson really excelled was maneuvering himself into CEO jobs and eliminating rivals who naively trusted him. When Johnson engineered the merger of Standard Brands, where he was CEO, into Nabisco, the huge cookie and cracker manufacturer, he was ostensibly in the number two role and faced numerous internal Nabisco rivals.

One was Dick Owens, Nabisco’s chief financial officer — at the time of the merger promoted to the title of executive vice president and appointed to the board of directors. “Whatever Owens wanted, Johnson got him. He approved a steady stream of Owens’s requests for new aides…. In Johnson’s warm embrace, Owens’s financial fiefdom grew greatly.”That is, until Johnson went to the CEO and told him that Owens had built too large and too centralized a financial empire. Owens was then replaced for a time by Johnson himself.

Next, Johnson gracefully pushed the CEO aside, doing it with flattery and kindness. Johnson had Nabisco endow a chair in accounting at Pace University in the name of the CEO, Robert Schaeberle. He ensured that the board named the new Nabisco research center building after the CEO. Soon, Johnson was the CEO of Nabisco. As Johnson’s allies realized, “a man who had his name on a building… might as well be dead.”

When you are in power, you should probably trust no single person in your organization too much, unless you are certain of their loyalty and that they are not after your job. The constant vigilance required by those in power — to ensure they are hearing the truth and to maintain their position vis-à-vis rivals — is yet another cost of occupying a job that many others want.

I’ve worked with clients who’ve experienced similar things as well.

A client (let’s call her Lucy) told me about having a casual chat with her new colleague (let’s call her Edna) one day when Edna made, what I felt was, an odd remark for the conversation they were having: “You know, I’m not interested in these power games. I don’t care about hierarchy. I’m so beyond that.”

The next couple of days Edna started asking Lucy about what she thought about various issues within the company. Edna said that this person or that person had said such and such, and wondered how Lucy felt about it.

It was clear that Edna was gathering intel, and if Lucy said anything damning Edna would go blabbing about it to someone more senior, and Lucy would be called in for a meeting.

What Edna didn’t know was that Lucy had already built up a good rapport with the CEO (Why not Bill?), and had gained his trust.

The next couple of weeks Lucy would come in and Edna would have done things “for her”, like scheduled meetings with accounting so that Lucy couldn’t make it and where they both should have been present. Since Edna had proven herself more than capable for her current assignment she was now vying for Lucy’s position.

What Edna said next was even more revealing: “I don’t want to step on your toes, or take your job. I just want things to run smoothly. So please tell me if I exceed my boundaries.”

To paraphrase Chandler Bing: Could you BE any more transparent?

So, in her infinite wisdom Lucy told Edna: “That’s great! In fact, it’d be amazing if you could take my job. That way I can finally focus on that opening in marketing!”

Edna tried not to look too surprised/disappointed. Lucy went to Bill and told him that Edna was an up-and-comer and that they should really keep an eye out for this gem.

I never got to follow up on what happened exactly, but a couple of months later Edna had apparently left the company.

Given Edna’s behavior, I’m guessing she probably didn’t endear herself to Bill. Probably by saying something bad about Lucy. And Lucy had nothing but good things to say about Edna.

So, what about Lucy? Well, she went on to work in marketing. Funny how things sometimes work out.

Again, nobody’s going to be able to give you a definitive answer. Given you kind of trust in the person may indicate that they might be able to help you understand and navigate the field.

Does that mean they should have power or direct input in where your business/company is going? Maybe not.

If you want to get a better feel for the situation then you might want to ask your mentor some purposeful questions.

Things like: “How did you become CEO? What were the power struggles like?”, “Have you been on any boards? Tell me more about that experience”, and so on.

It’ll give you some data to work with. If you’re not good at discerning that kind of information, or are genuinely just not interested in those aspects, then I’d suggest you surround yourself with people who are.

It’ll serve you in the long run.

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Have a kick-ass ₢eative day!

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