When You're a Startup CEO: Four Ways to Optimize the Relationship With Your Mentor

The latest issue of Harvard Business Review has a terrific article titled, "CEOs Need Mentors Too." It's based on the outcome of a two-year scholarly research study and we found it to be comfortable validation of what we do at Junto. The article was brought to our attention by one of our CEO Mentors, Kevin Rafferty. 

For context, our nine-month program in entrepreneurial leadership has four elements - JuntoForum, JuntoClasses, JuntoTutoring, and JuntoMentoring. In the latter, each company enrolled in Junto is matched up with six mentors. Five serve together as a Mentor Team, similar to an advisory board. The sixth one serves as an individual mentor to the CEO, focusing on leadership development. Kevin Rafferty is a CEO Mentor in our current cohort, JuntoIII. 

I haven't asked him directly but I believe the reason he shared it might have been that he saw parallels between the article and the Junto way of mentoring. And in comparing the two, we concluded that there are four distinct strategies that help optimize the mentoring process and relationship:

  1. The Match

  2. Empathy

  3. Structure & Rigor

  4. Experiences Over Advice

What follows are passages from the HBR piece along with what we do with JuntoMentoring.


We are convinced that more CEOs should connect with mentors rather than assume that theirs is a burden to be shouldered alone. But we also discovered aspects of such arrangements that make them trickier than the mentoring that takes place at lower organizational levels. At the CEO level, special considerations must go into making a match between mentor and mentee, structuring their sessions to deliver the intended benefits, and prioritizing the process so that it isn’t crowded out by other demands.

When a cohort begins, we spend hours mulling over who gets matched with whom in the mentoring program. We consider industry (we don't match people from the same one), personality, location, age, experience, and several other factors. JuntoMentoring sessions are structured and process-driven but not constraining. We let the mentors and apprentices set the agenda but will ask that they are aligned with the CEO's and the company's goals for the program. And finally, we "prioritize" the process by recommending monthly meetings or shorter bi-weekly meetings, and then ask to be included in the calendar invite so we're aware of the meeting schedule.


CEOs need wise mentoring. That’s not the same as coaching. Although executive coaches are often superb at providing feedback and closing gaps in specific managerial skills, precious few have actually worked in equivalent roles themselves. Mentors, by contrast, are role models who have “been there and done that.” They can offer timely, context-specific counsel drawn from experience; wisdom; and networks that are highly relevant to the problems to be solved.

A requirement for the CEO Mentors is that they are seasoned CEOs who have "been there and done that". They must have the ability to empathize with the less experienced CEO, being able to understand emotionally (wisdom) what that person is going through, in addition to understanding the rational and intellectual side (knowledge). This is the kind of thing that can't be accessed by a Google search or a Quora question. Wisdom is highly contextual, highly detailed and, obviously, very personal.


...the expectation that both parties will prioritize and prepare for meetings that are set and organized by the mentee. It’s never easy to carve out time on a CEO’s calendar. But to engage in the kind of mentoring described here and stick with it, the executive must make it a part of his or her workflow. Sessions should have formal agendas, defined by the problems currently confronting the CEO and shared far enough in advance to allow mentors to reflect on their experience. Robert Swannell, the chairman of Marks & Spencer, describes why he chose this kind of mentoring arrangement for a new CEO: “We wanted it to be a formal program where people knew we were spending money on it, it would be taken seriously, and there would be a certain rigor to it.”

We know that Junto is a big investment for the enrolled companies, in both time and money. And we've learned that the more rigor there is, the more seriously they take the process, and the more they get out of the program.

So when the CEO Mentoring begins, each Apprentice sets goals and metrics for his/her leadership development during the program in a dashboard document that is shared with the Mentor. Before each meeting, the Apprentice then updates the dashboard with outcomes since the last meeting and a brief agenda for the next one. After each meeting, the CEO Apprentice updates the dashboard with key takeaways, action items and to-do's, and relationships/connections to make. In addition, the CEO Mentor updates the dashboard with his/her own notes, ideas, and reflections.


Finally, and despite such a disciplined structure, the mode of knowledge sharing generally preferred by both parties is storytelling. Most mentors told us that they shared specific and relevant examples from their own careers—including not only triumphs but also poor decisions that resulted in bad press, tarnished reputations, employee layoffs, or share price declines. [Stories] evoke emotion and empathy, they prove far more memorable than other forms of information and idea sharing. By presenting a chronological series of events, decisions, and consequences, they suggest lessons without asserting them aggressively. They are always about someone other than the listener, so they create psychologically safe spaces in which to ponder “What would I do?”

One of the core operating principles in Junto is that we discourage advice-giving in favor of shared experiences and stories. Giving advice, in our view, is presumptuous on many levels. But real experiences are something that cannot be argued, judged, or dismissed. They are what they are, and they usually contribute to contemplation and conversation.

Unlike the rest of the Junto program, our team is not in attendance during the CEO Mentoring sessions so we trust both parties to follow this guideline. They admit that it's hard. But we've learned that, over time, the Apprentice is exposed to so much experience-sharing in the rest of the program (where our team can enforce it) that they bring that expectation to the CEO Mentoring sessions. In turn, the CEO Mentor begins to adapt his/her contribution, resulting in a much better mentoring experience for both.