Admitting Failure: Learning From Mistakes in Philanthropy

Posted May 11, 2015
By the Annie E. Casey Foundation
Blog admittingfailure 2015

I was recent­ly invit­ed to speak about mis­takes and learn­ing in phil­an­thropy at the Grants Man­agers Net­works annu­al con­fer­ence. My talk and pan­el pre­sen­ta­tion argued that admit­ting fail­ures con­tributes to high-qual­i­ty imple­men­ta­tion, inno­va­tion of new strate­gies and improved gov­er­nance and trans­paren­cy. It’s good med­i­cine that doesn’t always taste so good. Yet despite increas­ing phil­an­thropic inter­est in mis­takes and learn­ing, many foun­da­tion staff still find it dif­fi­cult to have con­ver­sa­tions about mistakes.

Many fac­tors con­tribute to this chal­lenge. First and fore­most is the jar­ring lan­guage of mis­takes and fail­ure itself, which sug­gests dis­mal final­i­ty rather than a nat­ur­al step in the vir­tu­ous cycle of tri­al and error that leads to bet­ter grants and bet­ter pro­grams. These words also ignore the social sector’s com­mon lan­guage of bright spots” that inspire us to build upon emerg­ing solu­tions to dif­fi­cult problems.

I find the mis­takes lan­guage brac­ing, but many do not. I sug­gest foun­da­tions and non­prof­its adopt lan­guage that works for them, such as do-overs, lessons, mid­course cor­rec­tions, truth-telling or self-reflec­tion. And it may make sense to dis­cuss suc­cess­es and fail­ures together.

Anoth­er ques­tion I fre­quent­ly get is how to start the con­ver­sa­tion about mis­takes and learn­ing. Should one start with the foundation’s CEO, board of trustees or pro­gram direc­tors — or with a few trust­ed col­leagues? There are note­wor­thy exam­ples of foun­da­tion and social sec­tor CEOs — such as Paul Brest, for­mer head of the Hewlett Foun­da­tion, or Jim Yong Kim of the World Bank — lay­ing down the gaunt­let about speak­ing truth about mis­takes, whether in Amer­i­can Idol type con­tests, fail fairs” or fail fests” or annu­al fail­ure reports.

My belief is that there are many ways to start con­ver­sa­tions about mis­takes and at many orga­ni­za­tion­al lev­els. No mat­ter where you start, key ingre­di­ents for pro­duc­tive dis­cus­sions are suf­fi­cient time, a safe place and a cham­pi­on who sup­ports such learning.

Talk­ing about mis­takes only on spe­cial occa­sions is a com­mon mis­take, how­ev­er cathar­tic it may be to blurt out a fail­ure sto­ry. The pur­pose of talk­ing about these fail­ures is to build our capac­i­ty to rec­og­nize mis­takes ear­li­er and to make smart mid­course cor­rec­tions. This requires an ongo­ing com­mit­ment to mak­ing these con­ver­sa­tions a habit.

I learned this les­son the hard way from a group of part­ner grantees. A few years back, I co-edit­ed a book called Mis­takes to Suc­cess that com­piled mis­takes sto­ries in the field of com­mu­ni­ty eco­nom­ic devel­op­ment. We fol­lowed up with a tool­box for start­ing and sus­tain­ing mis­takes con­ver­sa­tions, called the Mis­takes to Suc­cess Roadmap. We then test­ed these tools with grantees.

These non­prof­it part­ners taught me two impor­tant lessons. First, they want­ed to test the tools in the con­text of reg­u­lar orga­ni­za­tion­al process­es like bud­get, strat­e­gy, or pol­i­cy pri­or­i­ty cycles — not one-off expe­ri­ences. Sec­ond, after a few months, they asked me, the mis­takes guy,” how we had insti­tu­tion­al­ized mis­takes and learn­ing at Casey. I gulped. We had con­vened a few mis­takes potlucks, which involve each par­tic­i­pant bring­ing a mis­take to share with the group, and I had shown my super­cool mis­takes Pow­er­Point pre­sen­ta­tion dur­ing a staff devel­op­ment ses­sion. But we hadn’t made mis­takes and learn­ing an orga­ni­za­tion­al habit.

For the past year I have tried to cor­rect my mis­take with­in my team, which focus­es on eco­nom­ic oppor­tu­ni­ty and com­mu­ni­ty change. We have learned about emer­gent learn­ing tech­niques that help look for themes across mis­takes sto­ries (in the Roadmap tool­box), trained staff in facil­i­tat­ing emer­gent learn­ing and prac­ticed before- and after-action reviews to build up our abil­i­ty to rec­og­nize mis­takes and adapt accord­ing­ly. It’s still a work in progress, whether it involves debrief­ing after a board pre­sen­ta­tion, a site vis­it, a new grant-mak­ing pro­ce­dure or a new pro­gram­mat­ic investment.

I con­clud­ed my Grants Man­age­ment Net­work pre­sen­ta­tions by rec­om­mend­ing a few do’s and don’ts for encour­ag­ing and sus­tain­ing mis­takes and learning.


  • cre­ate time and space to dis­cuss mis­takes and learn from them;
  • find a cham­pi­on, test­ing dif­fer­ent tools; 
  • make it reg­u­lar; and
  • have fun!


  • blame grantees;
  • do it only once;
  • gripe rather than find solu­tions; and
  • put off change.

My most impor­tant les­son from talk­ing about mis­takes with col­leagues is that we shared our core aspi­ra­tions, what kept us up at night and the dilem­mas we felt in sup­port­ing change. For me, that shar­ing makes it worth say­ing tough words like mis­takes and failures.

Read more about how oth­ers have learned from mis­takes in this recent piece from the Phil­an­thropy Round­table.

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