How to Find A Good Advancement Leader: Ask the Right Questions

You’ve had a least one bad boss or worked in at least one depleting advancement operation. Now you’re interviewing for a job and want to make sure it doesn’t happen again. Remember the word “interview” means “to see one another.” Ask good open-end questions and listen carefully to how your potential boss reveals him or herself.

Example question: What multi-year goals have you set for the operation and how much time will it take for someone in this position to be as successful as you would like?

Listen for: Someone who understands the power of patient persistence and the interdependencies of sustained success. A good boss will give you enough runway to succeed and define how you should contribute to the team, and they to you.

Example question: In which professional achievements do you take the greatest pride?

Listen for: How often this potential boss says “I” versus “we.” The complete absence of “I” should be just as concerning as the persistent use of it. Friendly Fred can use consensus building to avoid decision-making and fail to stand up for his team, even when their work is extraordinary or the criticism coming down on them is extraordinarily unfair. On the other hand, Mimi can dazzle you in the first meeting, seem oh-so-chummy and charming but, once onboard, you’ll discover you’ve been cast in a role reversal – it’s not her job to create conditions that will allow you to succeed, it’s your job to prop her up, make her look good and provide endless adulation.

Example question: Who or what has been most influential in your career growth?

Listen for: Mimi has a hard time with this. She depicts herself as a foundling who was suckled on wolverine milk and succeeded by living off the lichen beneath bat droppings on the sheer cliffs she climbed. She sees herself as self-made, not the beneficiary of good teachers or lucky breaks. Friendly Fred gushes but doesn’t share any gritty moments in his schmoozy journey. He spreads praise so far, wide and thick that it becomes clear being so overly grateful to everyone is a mask for being grateful to no one.

All kidding, or Fred and Mimis aside, good bosses are blend of characteristics, not caricatures. There are no end of social media posts portraying the perfect boss as endlessly self-denying and supportive of his or her team. Yet, some elements of ego are essential to leadership and to withstanding pressure. So, the two biggest mistakes in looking for a boss are:

1. To look for a perfect boss
2. Fall for someone who pretends to be one

Traits we pay too little attention to include courage, character and fairness. Below are other attributes of good bosses that we don’t look for, recognize or appreciate often enough.

Five Important but Under-Appreciated Characteristics of Good Bosses
  1. Cordial, but they don’t pretend or aspire to be your friend; to be fair they need to keep a certain professional distance.
  2. Hold you to high standards but not higher than those they hold themselves to.
  3. Invested in your professional development and committed to creating productive work conditions but don’t feel the need to keep everyone happy all the time.
  4. Give everyone a voice but not a vote; leaders make tough, often unpopular calls.
  5. Don’t share their struggles with their higher ups with you; they support their staff but don’t expect their staff to support them or feel sorry for them.


Jim Langley is the president of Langley Innovations. Langley Innovations provides a range of services to its clients to help them understand the cultural underpinnings of philanthropy and the psychology of donors and, with that knowledge, to develop the most effective strategies and tactics to build broader and more lasting communities of support. Jim has authored numerous books including his most recent book, The Future of Fundraising: Adapting to New Philanthropic Realities, published by Academic Impressions in 2020. 


Related Resources:


Notify of

Inline Feedbacks
View all comments
Get smarter with the SmartIdeas blog

Subscribe to our blog today and get actionable fundraising ideas delivered straight to your inbox!