Most heads and chairs of nonprofits generally recognize that they should retain outside assistance when the board needs to learn or review the principles of good practice or when the board chair/head relationship is about to go “off the rails.” Yet most heads and chairs rarely think that they need or would benefit from professional coaching even though many CEO’s of for profits companies, even experienced ones leading famous corporations, seek professional coaching as a recent article published by Harvard University Business School demonstrates.

Heads of schools and board chairs can benefit periodically from professional mentoring and in most cases the head’s or the board’s professional development budget covers the cost. The head or chair may seek to sharpen their skills in such areas as board relations; conflict management; resolving a specific crisis; transitioning into the head’s or chair’s role in a demanding setting; guiding a board towards becoming strategic thinkers; or managing a constituent’s need for more communication or involvement. Still others may be seeking enrichment as part of their personal journey towards continuous professional improvement.

Regardless of an individual’s goals when he or she enters into a coaching arrangement, the process is most successful when the individual approaches it with a sense of inquiry, a desire to learn and a understanding that the organization is the beneficiary as well. Coaching is also most rewarding when it takes the form of a healthy and robust debate and when ego is not a factor. The cases below show that the format is often an exchange of “stories” which in turn translates into lessons in leadership.

I. Case Number 1

This Head has been the leader of a well-known, financially strong US School for eleven years. She is passionate about the School’s mission and vision but her occasionally abrupt style can rub her Administrators and a few key donor trustees the wrong way. While her strengths have always outweighed her weaknesses so that her position has not been threatened, a disgruntled staff member attempts to undermine her with the Board. The situation appears in the local press and reflects poorly on the School.

Three key Board members, including the Chair, contacted Littleford & Associates with the goals of shoring up the Head; opening her eyes to her own mistakes; and ensuring that the rest of the Board acknowledged their own misbehaviors. The coaching began by listening to the Head and her description of the incidents leading up to the story. These revealed some serious board missteps and examples of boundary crossing. Yet she was reluctant initially to acknowledge some of the weaknesses in her own leadership style that caused disloyalty to her as well as her ultimate inability to mentor, and if necessary terminate dysfunctional employees who repeatedly undercut her.

After six months of coaching the Head and interviewing the entire board, this Consultant conducted a workshop to attempt to rebuild damaged “fences” and to persuade all parties to move on. As a result, the Head’s near-term tenure seems assured as all parties have reflected upon their own actions and have agreed to make some important changes in their relationships with one another and with the staff.

II. Case Number 2

This Chair is overseeing a head search process which is presenting all sorts of challenges. The faculty is insisting upon a controlling role, such as the right to review the resumes of all candidates. This is actually their attempt to fill a power vacuum created by the Head’s own politically diminished state. A few Board members are engaging in inappropriate conversations with teachers and parents about the search and checking candidates’ references without prior approval.

This somewhat dysfunctional Board is influenced by a few trustees who do not like, or choose to ignore the core principles of good governance. The Chair is discouraged and prepares his resignation letter, but the rest of the board implores him to stay on for the good of the School and the search.

The Chair contacts our Firm in order to help him see a way forward. The Chair has a legitimate need to talk through his thought processes on a number of complex and interrelated problems. He is not sure whom he can trust with his deeply felt concerns, so the coaching role is one of listening, encouraging, asking probing questions and occasionally suggesting options for him to consider.

He has decided to continue to serve as Chair and to remain committed to the search. He intends to play a key role in building a healthier Board. He realizes that one or two well-meaning but micromanaging Board members are “off the reservation” and may require disciplining but also knows that the outgoing Head’s own leadership style has led to a number of challenging issues now confronting the Board.

III. Case Number 3

A Head of School retired after being the Founder and Head for almost 50 years. The Founding Head had achieved almost saintly status with the Board and members of all constituent groups. It would have been very challenging for an outsider to survive the transition.

The Board asked our Firm to mentor the internal Hire who is very capable, qualified and respected. Some staff members are making end runs to the Board with their issues concerning long overdue changes that the new Head has introduced. The Founder left the Board in the dark for so many years that a few Trustees eagerly embraced an opportunity to “help” by entertaining meetings with staff and parents.

So far, the coaching seems to be helpful. The new Head is listening carefully, reflecting thoughtfully, bouncing ideas off the Consultant and then moving deliberately to make and implement decisions. It is reasonable to expect that he will succeed although certainly, following a 50-year adored “spiritual” leader is difficult no matter how much mentoring a new head may receive. The Board was wise and generous to request and fund such outside coaching, and the Head appreciates it. The Board, in turn, is learning about the best ways to support the new Head.

IV. Case Number 4

A new Board Chair is feeling both honored and beleaguered. The Board that he inherited is engaging in the same activities that it did ten years ago which led to the untimely departure of the prior Head. Key Board members have linked up socially with several members of the current senior leadership team and other staff, not realizing that that same behavior threw the School into disarray years before.

In addition, the Chair is dealing with factions on the Board: one that wants this Head to depart early; another that wants the Head to stay and stand her ground despite her trials with her Team; and another that wants her to finish her contract but then not renew. At the recommendation of a long term Board member, the Chair contacts our Firm because we worked with the School during the prior crisis and warned in writing and on site of the same behaviors that are now recurring. He has read the reports from ten years before and asks us to help guide him through the current crisis to avoid a similar outcome.

This Chair is calm, thoughtful, reflective, dedicated, but increasingly discouraged by a few difficult Board members and the seeming inability of the Board to unite behind the Head, get past the recent crisis and focus on the mission. Again, this Consultant is playing the role of a sounding board, reminding him of the past and suggesting specific strategies to handle some important players.

V. Case Number 5

In this case, a solid Head, leading a growing school for a number of years stumbled on several personnel decisions, stirring up a hornet’s nest among staff and even some board members. A caring Chair, who wanted him to succeed, asked for our coaching which the Head gladly accepted and received. Over several months, we talked about the unfolding crises he was facing and the importance of regaining Board support. Just when he had forged new connections with Board members and negotiated a new contract, he avoided responsibility in a public context for an unpopular decision all knew he had made. Conflict avoidance was his unfortunate downfall, and it was then clear that he could not remain long in his current position.

In this case, the coaching then took the form of working with the Chair and Head to come to an amicable separation, with strong board financial support for a “soft landing.” The Head has an opportunity to find a situation that is a better fit for him.

VI. Case Number 6

This Chair has had a personal conflict with the Head for several years but managed it successfully by acquiescing to the Head in most situations. Recently, when the Head announced his decision to retire, and a search was launched, the Chair contacted Littleford & Associates who serves as the governance Consultant to the School. The Chair expressed serious concerns that the Head was attempting to influence the search inappropriately. The Head was pressing for his favorite inside candidate to succeed him and was actively attempting to thwart the search by asking his senior staff to contact the Board members to indicate that the search is “in trouble” and that they should turn to the internal candidate for resolution.

At this point, the Chair feels a need to inform the full Board of this issue, but he does not want to prompt the Head to resign prematurely or jeopardize certain donor connections that the Head has made. The The conundrum for the Chair is that he does not want to personalize the conflict with the Head but the search needs to continue on schedule and towards a conclusion that is best for the future of the School. Should someone else manage this aberrant Head behavior? This is a stressful and delicate problem and a fresh outside perspective is helping the Chair.

VII. Case Number 7

This is the case of a very successful Head of several excellent Schools who is committed to striving for self-improvement and leadership development. He initiated the arrangement with this Consultant for twice monthly mentoring/coaching sessions which focus on how he manages the faculty, the administration and how he interacts with and guides the Board. He is also focusing on his own goals, Board goals and the evaluation of the Head and Board as ways for both to learn going forward. He seeks an outside ear to listen and off of whom he can bounce ideas, and this Consultant is in turn learning from his innovative approaches to leading his School. Unvarnished debate and discussion seems the rule

The Board is paying for this coaching and in this Consultant’s mind, this is an example of what more heads should pursue and what most boards would support. It may well be that this Head and this Consultant will collaborate on an article for the Newsletter on this process and how it may be a model for other heads worldwide.

VIII. Case Number 8

This is about a Search Chair who is about to become the new Board Chair and who will be partnering with a new Head replacing a long term highly respected Leader. The Chair respects the Head, but has some serious doubts as well, most of which he is keeping to himself. His doubts are partly on target but partly misguided as he had enormous respect for the prior Head and is not processing fully that the transition will take at least three years. He needs to give the new Head the time to build his own team and for constituents to adapt to his style.

The Chair is having difficulty keeping some Board members in line and preventing them from contacting staff members and parents who do not like some of the decisions the new Head is making. So on a personal level, he has some doubts. On a board governance level, he knows his board is misbehaving and cannot be allowed to sabotage the new Head’s chances. He reaches out to this Consultant for guidance and assistance.

IX. Conclusion

It should never be embarrassing for a Head or a Board Chair to ask for outside one-on one-counsel. As any head knows, being a head is a lonely job, and as any board chair knows, the role of chair is a volunteer position that takes enormous time and energy.

Executive coaching can help leaders navigate challenging situations and allow them to grow personally and professionally which in turn benefits the schools they serve. Another beneficiary is the coach who enjoys the lively exchange of ideas and develops his or her skills as well. It can be a “win-“win”for all.

John C. Littleford
Senior Partner