Back to Guidebook

16 Questions

An Organizational Guide for Great Character Formation

“By their fruit you shall know them…”


The world is full of organizations that seek to transform character and improve lives, but how can you tell which ones are successful and which ones aren’t?

The following questions should provide a guide to help you make these judgment calls. They fall into 16 categories, corresponding to the 16 crucial features that truly formative institutions tend to possess:

1. TELOS: Does the organization have a clear, strong reason for being in the world, embraced and pursued by all of its members? Does it give its members organizing criteria for what to love? 

2. LITURGIES & RITUALS: Is there a covenant or creed that is affirmed regularly as a community, in word and deed? Are there communal rhythms, routines, and rituals?

3. FULL ENGAGEMENT by ALL MEMBERS: Are all members of the organization, regardless of position or stature, engaged in the mission and aware of the significance and contribution of their roles?

4. POWER of the PARTICULAR: Does the organization have a particular identity, a thick set of norms that gets passed on to its members? Does it have a unique quality that is recognizable in those it has shaped? 

5. WHOLE PERSON: Does the organization have a clear conception of the whole person—head, heart, and helping hand—and seek to develop it? Are employees and departments integrated across domains, serving constituents in complementary, mutually reinforcing ways? 

6. HEALTHY RELATIONSHIPS: Does the institution put relational health as the foundation for its success? Does the organization foster social trust? Does it have a strong sense of community? 

7. TECH-WISE: Is the institution careful about the latest technological advance, embracing it insofar as it promotes healthy relationships and individual skill, and setting limits when it makes those objectives more difficult?

8. INTENTIONAL PLURALISM: Does the institution foster opportunities to relate to those unlike yourself? Are members consistently exposed to other worlds, trained in the arts of civility, deep listening, and cross-cultural agility?

9. STRUGGLE & GROWTH: Are there opportunities for growth and tests of character? Does the organization have a process by which such struggles are given meaning and direction?

10. VULNERABILITY & ACCOUNTABILITY: Has psychological safety been established such that individuals feel free to be honest? Is there a structure of mutual accountability? 

11. REFLECTION: Are there built-in processes for reflection, and excavation of one’s inner life and public fruits?

12. EXEMPLARS: Are there attentive and conscientious authority figures who serve as role models, coaches, and mentors? Does the leader set the character standard for the organization?

13. AGENCY & INITIATIVE: Are members of the organization empowered to act, create, initiate? Are they encouraged to be responsible moral agents, not simply passive consumers?

14. JOY: Is there joy in the house? Are hospitality and unconditional welcome a key part of the institution’s DNA? 

15. TRANSFORMATION: Are there consistent testimonies of whole-person change in a positive direction? 

16. GENERATIVITY: When people depart from this formative institution, do they promote a similar culture in other contexts? Has the institution imparted a set of ideals that members want to live up to ever after?

It’s important to note that the features of effective character-­building institutions are fundamentally interrelated: they are both interdependent and mutually reinforcing. This is particularly key in today’s philanthropic and academic climates, which tend to cobble together a creed out of lots of disparate pieces. Instead, we should understand the fabric of character as precisely that: a fabric—interwoven, and much of the time, indivisible.

Feel free to test these against your own experience. When you reflect upon the most profound encounters in your own life, the most transformative institutions and relationships, do the memories share the above characteristics? You may be attracted to some traits over others, depending on your area of interest, expertise, and foundation portfolio. That is fine. Start with what resonates. In the pages ahead I will peel apart the questions and the contexts that best embody them. Oftentimes these organizations struggle to articulate the magic that makes them work; a common weakness that could almost be included in this list of signaling criteria. They instead succeed at the most demanding of tasks: transforming souls, and cultivating character by way of a healthy ecology of norms and relationships.

dowload link source