Montieth Illingworth
Montieth Illingworth

Imagine that you’re young, rich, admired by your professional peers and the titans of your industry. Congressional leaders want to know what you think, as does much of the world. As CEO, you have your hands on the levers and dials of the most important technology in more than a generation in terms of its potential impact—very good or potentially very bad for humanity.

Then the board of directors decides to fire you because your lack of consistent candor with them hindered its ability to exercise its responsibilities. The fact that your board is of a non-profit that oversees the for-profit company you run is unusual but arguably doesn’t matter in the board’s decision. You serve at the pleasure of the board.

This is about Sam Altman, of course, and the power struggle between him and the board of OpenAI. What happened in the weeks following is relevant and an under-appreciated issue when we look at these events through the lens of CEO mentoring, an often-overlooked aspect of why CEOs are able to make good decisions, and sometimes make bad ones, all of which intersects with the role and duties of a board.

There are volumes written about mentoring—what it is, how it’s done, and all of its benefits. Most of that clearly important and helpful analysis is focused on employees and managers. Less is written about CEO mentoring. One notable exception is the 2015 Harvard Business School survey of 45 notable CEOs. 71 percent said that their mentoring improved company performance. Some 69 percent said they were making better decisions and 76 perccent said they more capably fulfilled stakeholder expectations. Notably, 84 percent said that mentoring helped them avoid costly mistakes.

But that’s just raw data. The most valuable insights to be had are in the core principles of CEO mentoring and how they’re applied in practice:

  • The CEO, or would-be corporate leader, has to want it. A case can be made that the best CEOs—those that can lead and manage most effectively through good times and bad, with heavy doses of inspiration, empathy, nimbleness, adherence to corporate policies, ethics and a strong moral compass—actively sought out mentors, informal and formal.
  • The mentor, typically an already accomplished corporate leader, needs to be completely frank in her advice and counsel. Someone with their sights on a CEO leadership role doesn’t need more fuel to fire their ambition. They need wisdom grounded in experience and much of that is comprised of hard truths that can be tough to hear, especially when the receiving CEO feels she’s already successful.
  • Truly effective CEO mentorship never ends. It’s not a graduate degree. It’s a process, a journey, and one that changes as the path of a leadership role unfolds. And a CEO who actively finds mentors knows when to find a new one for that new stage in her career.

All of which is fine, except theory needs to meet practice. Intention and reality are two different things. In the end, it’s all about the outcomes that are produced and who is impacted.

Consider former GE CEO Jack Welch. In 1999, he popularized the concept of “reverse mentoring” defined as a system for sharing what can be learned amongst managers with various backgrounds. Welch was also dubbed “Neutron Jack,” who since his passing has spawned a virtual industry in his name and brand for teaching leadership based on his accomplishments. When he left GE it was soon clear how his decisions led to a series of disastrous strategic errors and failures of management. The shareholder value he created was a mirage and later greatly suffered.

It’s key, therefore, to think about what we’re measuring when we look at mentoring models. Is it about generating shareholder returns alone? Is it about facing and overcoming enormous challenges, whether within the business or in the market against competitors? Is it about just delivering a product or solution that the world loves (despite its negative impact a la Facebook, let alone other social platforms)? Or does it all come down to the ethical and moral fortitude of the CEO, let alone that of the rest of the C-Suite and the board? (look no further than Fox Corp.).

It’s all those things and more and one lesson from recent CEO history is certain: CEO mentoring, however it happens, is something that should also be seen by employees, and stakeholders, as ingrained not just in the Star Chamber workings of the C-Suite but also in the culture of the organization. CEO mentoring is not an exclusive club—it also has to be an expression, however broadly, of principles, values, and practices that the organization stands for, believes in, and practices.

Stress-testing institutionalized mentoring—look at CEO succession

Typically, people reference the multitude of lists of the world’s best managed companies, then conflate that with good, institutionalized CEO mentoring. Maybe. Well managed companies typically have CEOs with strong leadership abilities but that doesn’t mean they have right practices in place, however informal, to mentor the CEO’s replacement. Succession is always tricky. Doing it right requires intention, and mentoring that successor should be central to a achieving a smooth and effective transition.

How do you recognize effective institutionalized mentoring? Consider IBM, which routinely celebrates National Mentoring Month. But mentoring within the organization and at the top are two different things. That said, just about every IBM CEO since Lou Gerstner—a long chain of succession triumphs—has expressed gratitude for the mentoring he or she received there and very publicly. Mentoring, for IBM, is central to its corporate identity and brand. That’s because it’s legitimately ingrained within the organization. It’s done right at the CEO level because everyone below the C-Suite has their eyes on the outcomes.

Is hunter/gatherer mentoring better?

Some of the most effective CEOs are hunters who surround themselves with gatherers. Hunters have a vision; they know what they want, and they go and get it. They array the people around them to achieve the mission. Many such CEOs create concentric circles of gatherers who take the direction from the CEO to execute. The one (and it’s usually just one) who can rise from gatherer to hunter gets a shot at becoming CEO.

The right kind of mentoring here means “managing to the person”. That is, seeing that this potentially next CEO is not just a good hunter but a different kind of one that improves on her predecessor. That is, unless the successor is sabotaged.

There are numerous examples of this in recent corporate shake-ups. Most vividly, how Bob Iger hand-picked Bob Chapek to replace him at Disney only to later cut him off at the knees. Take also the short tenure of Chris Licht as CEO of CNN. Extensive media reporting portrays Licht as being mentored by parent company Warner Bros. Discovery CEO David Zaslav. Whether it was the mentoring failure of the hunter (Zaslav) or the inability to perform at the higher-level gatherer and his ambition to become the new uber hunter (Licht) is the question. Shades of The Hunger Games.

Peter Pans make good CEOs, kind of

Peter Pan CEOs come in two variations: the ones whose innovations truly change the world and the ones which could have but for their massive implosions as leaders. Think of Steve Jobs vs. Sam Bankman-Fried. Think of Bill Gates vs. Adam Neumann.

Many people don’t know that Steve Jobs was mentored by none other than Bill Hewlett, the co-founder of Hewlett Packard. As a twelve-year-old, Jobs called Hewlett at his home looking for advice and connection. He also sought out for mentoring from Intel CEO Andy Grove and Polaroid pioneer Edwin Land. What’s important here is that Jobs sought out his mentors. He also challenged them with his own ideas

Contrast that to Sam Bankman-Fried, who once said he “was very skeptical of books.” WeWork’s Neumann was frequently quoted saying much more seemingly worthy things (e.g., “as the world becomes a more digital place we cannot forget about the human connection”). He also tried to trademark the word “we”. Of course, both created businesses that ended up in bankruptcy. Did they have mentors? Doesn’t seem so. But Neumann famously wrote a piece for Fast Company saying he was glad he never had a mentor. Mind you, he highlights one of the partners at a VC firm that funded WeWork as an important “advisor.”

That raises the question of whether VCs and private equity firm owners are good mentors to Peter Pan CEOs, or any newly minted CEO of any kind for that matter? That points to whether the people who invest millions (even billions in the case of Microsoft in OpenAI) can truly be mentors to the CEOs whose futures they in effect essentially control—will commercially driven self-interest displace frank and objective counsel?

Which brings us back to Sam Altman. He may well have had mentors. Some of the media reporting on his dismissal, his fight against the board and his return, references various Silicon Valley luminaries he turned to for advice. Whether these relationships are more of a circle of like-minded commercial interests or there are examples of some who challenged his thinking and decision-making, is uncertain. But the larger question is this: given the power, promise and potentially damaging impact of generative AI, doesn’t Altman need mentors who will challenge his decision-making?

A related issue is whether a more institutionalized architecture should be in place for CEO mentoring at OpenAI, a la IBM. And for a company that early in its development, is institutionalizing at almost any level even possible given its rate of growth and evolution? IBM has decades of institutional learning under its belt. It has a long track record of successes and failures (recall the short and happy life of the IBM PC). But it made learning an institutionalized priority on that journey. IBM learned to learn.

What is of concern for a company like OpenAI now is the potential scale of the mistakes relative to the learnings that can be achieved at the CEO level. The reasons why OpenAI was a nonprofit was for its board to have a laser focus on the public interest. Altman was terminated by the then board because it thought he failed to protect that interest. The fact that in a few days’ time Altman was back in power and those board members who most acutely expressed concern about him were turfed out gets to the heart of why CEO mentoring here is vital. Did Altman, essentially, in his countercoup get rid of potentially good mentors?

Everything with generative AI is happening fast. The mistakes will come fast. Can any one person with the power of the CEO really see those mistakes before they happen, and course correct in real time? No, not without mentoring, if there’s time.


Montieth M. Illingworth is CEO of Montieth & Company, a global, specialist marketing communications firm with offices in New York, London, and Hong Kong. He is a former journalist and author of a biography of former heavyweight boxing champion Mike Tyson.