by Barbara Barron | Posted May 26th, 2026 | Subscribe to this newsletter
Here’s the challenge: Do We Have the Right Leader?
Since I began my consulting practice in 2017, I have been asked by a Head of School to evaluate (I say appraise) the advancement program of a school more than a dozen times.
In most cases, those Heads were new to the school and, in four cases, the Heads were in their very first headship. Such a smart choice when you think about it. Who wouldn’t benefit from getting an early, objective, and experienced set of eyes on things at the start of a big job?
How good it is to understand deeply where the opportunities lie and, vitally, where the weaknesses are hiding in plain sight? And those weaknesses are often, sadly, the people in the department.
To say that I don’t relish discovering people in the wrong seats or not well suited to their positions is an understatement. I am, in my heart, a development person. I know the role and its many pressures and tensions. I haven’t always been a stellar leader but, over time, I learned how to spot and promote talent, support bold actions that yield results rather than sticking with the way we’ve always done it, and to give honest, constructive feedback.
Ultimately, I report to the Head regardless of the consulting gig’s purpose. I need to be their trusted advisor. Still. It’s brutal to need to tell a Head that their director (or others on the team) either need to be redeployed or released to industry.
Ouch!
So how to do it, then?
Have you subscribed to this newsletter yet? It only takes a minute.
Tell the truth
Tell the truth. Make a change.
In several instances, the director was not the right person for the job, at that time. Everyone liked them! But that quality – being liked – while essential in our work, is not enough.
Sometimes, the Board has no confidence in the director (a death knell), or other members of the team felt rudderless and unsure about what was the strategy. It can also show up in the Head just not feeling 100% about the advice or strategy the advancement director is advocating. They find themselves asking: Is that the best we’ve got?
As anguishing as that realization can be, what I’ve come to know with a certainty is what’s right for the school is (ultimately) right for the individual, even if it doesn’t feel like that in the moment.
In one case, the director moved into a different and more satisfying position at the school. In another, the director gave up responsibility for marketing and refocused solely on development. That particular change had the nice result of allowing a member of the marketing team ready to lead to flourish.
Of course, in other cases, it meant the director left the school. Painful, yes. But it is essential that the Head fully understand and trust what’s going on in that vital office and that the Board has full confidence.
Here’s their Success:
Happily, after the disruption, in every one of these cases the school is on better footing. Some have had successful capital campaigns, or have seen strong growth in annual giving, or dug deep to start or renew major gifts and planned giving programs. In this work, it’s all about the people. Helping schools find, retain, and mentor great development pros is a joyful part of my work.
Have a challenge? Give me a call! And as always, thanks for all you’re doing.
Barbara Barron
[email protected]
Share this post:
BARBARA BARRON is one of the most respected and highly sought-after independent advancement professionals in the country, having worked with dozens of schools in every corner of the United States.
She has raised over $20 million for schools where she served as the Director of Development. Barbara is a New York Times bestselling author, speaker, and presenter who currently advises dozens of schools in various capacities. She is considered a thought leader in the world of advancement, with her writing widely shared by professionals in development offices worldwide.
More Advancement Articles
