Why Smart Leaders Seek Counsel and Recruit a Wingman

By Dr. Barrett Mosbacker

January 5, 2025

Dear Bill,

When I walked into this office just now I felt the same sense of wonder and respect that I felt four years ago. I know you will feel that, too.

I wish you great happiness here. I never felt the loneliness some Presidents have described. There will be very tough times, made even more difficult by criticism you may not think is fair. I’m not a very good one to give advice; but just don’t let the critics discourage you or push you off course. You will be our President when you read this note. I wish you well. I wish your family well. Your success now is our country’s success. I am rooting hard for you.

Good Luck, George

That is the letter George H. W. Bush left on January 20, 1993, for Bill Clinton during Clinton’s transition to the presidency. Many presidents have followed the practice of leaving a letter of encouragement and advice to their successor.

While it is customary for a departing president to leave a letter of advice for the incoming president, this is not customary for a departing school administrator, nor is it common for an incoming leader to seek guidance from the successful leader being succeeded. That is unfortunate, as both practices would benefit the new leader and the school he or she leads.

The Scriptures tell us that wisdom lies in many counselors (Proverbs 11:14; 15:22; 24:6). One of your best sources of wisdom is the effective leader who came before you. That leader was successful for a reason and possesses a wealth of knowledge that can prevent you from making costly mistakes and guide you toward success. Squandering this resource is like winning the lottery but refusing to claim the prize.

Assuming the former leader is available and willing, there are two reasons why an incoming leader may not seek advice from the prior successful leader: fear or pride.

The fear is that consulting the former successful leader will somehow diminish or overshadow one’s own leadership and credibility. This fear is unfounded. Seeking advice is not relinquishing your leadership; it is a way to strengthen it. Every school has its landmines. The former leader will know where they lie and can help you avoid stepping on them. That leader is also aware of the sacred cows, who the most influential people are — they are not always those holding formal positions of authority — who the troublemakers are, and what has and has not worked in the past. Take advantage of this knowledge and wisdom.

The other reason for not seeking advice from the previous successful leader is pride. 1 Kings 12 recounts the story of King Rehoboam, who succeeded King Solomon. Can you imagine following Solomon? One would think that Rehoboam would be wise enough to learn from those who had advised the wisest man who ever lived — but he was not. He chose instead to follow the advice of young men who had grown up with him (1 Kings 12:8). The counsel he received, and his subsequent response to the people, was filled with pride:

And the young men who had grown up with him said to him, “Thus shall you speak to this people who said to you, ‘Your father made our yoke heavy, but you lighten it for us,’ thus shall you say to them, ‘My little finger is thicker than my father’s thighs. And now, whereas my father laid on you a heavy yoke, I will add to your yoke. My father disciplined you with whips, but I will discipline you with scorpions.’” So Jeroboam and all the people came to Rehoboam the third day, as the king said, “Come to me again the third day.” And the king answered the people harshly, and forsaking the counsel that the old men had given him, he spoke to them according to the counsel of the young men, saying, “My father made your yoke heavy, but I will add to your yoke. My father disciplined you with whips, but I will discipline you with scorpions” (1 Kings 12:10–14).

The Scriptures warn:

Pride goes before destruction, and a haughty spirit before a fall (Proverbs 16:18).

Do not allow pride to keep you from soliciting the advice of the successful leader who came before you.

In one school I led, I scheduled a monthly lunch meeting with the former head of school. We enjoyed good food and warm fellowship. I made a habit of covering three things during our meetings: I kept him updated on my progress and initiatives; I shared any challenges I was facing and sought his advice; and I asked for his insights on my leadership and any suggestions he might offer. Those meetings were invaluable.

Seeking the advice of the former successful leader honors that leader and pleases the Lord. It also sends a powerful message to the community — that you are wise enough and humble enough to listen and learn from those who came before you. The result will be increased credibility, trust, and respect for your leadership. You will gain much and lose nothing by mining the wisdom earned through the successes, mistakes, and many years of experience of the leader who preceded you.

Find Your Wingman

Over the years I learned the importance of recruiting a wingman. A wingman is a pilot who flies alongside the leader of a flight formation, offering protective support and backup. The wingman acts as a second pair of eyes, ensuring the safety and success of the mission by covering the lead pilot’s rear and flanks.

You need someone to cover your rear.

Your wingman is someone discreetly supportive who stands by you whenever someone tries to undermine your decisions or leadership. The ideal wingman is a person of impeccable character who offers constructive criticism, wise advice, and unwavering belief in you. This person is widely respected by school leaders and the entire school community. The wingman might be a former leader, a trusted board member, a member of your senior team, or someone else entirely. The crucial thing is having someone watch your back and support you when others seek to undermine you, your decisions, or your reputation — someone you trust implicitly to protect you from those who wish you harm.

Find a trusted wingman. You have everything to gain and nothing to lose.