Worst Practices of a Social Entrepreneur: You can learn more from your mistakes than from your successes

8/3/2019 Worst Practices of a Social Entrepreneur: You can learn more from your mistakes than from your successes

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Stanford Social Innovation Review

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On the Frontlines

Worst Practices of a Social EntrepreneurYou can learn more from your mistakes than from your successes

By Paul Schmitz

Stanford Social Innovation Review

Fall 2007

Copyright© 2007 by Leland Stanford Jr. University

All Rights Reserved



As president andCEO of Public

Allies, a nationalleadership develop-ment organizationheadquartered in

Milwaukee, I’ve learned a lot from the best practices of other social entrepre-neurs. But I’ve learned even morefrom our “worst practices” – what wesuck at, how we’ve screwed up, andwhat we’ve done to get better.

Every time I present my list of worst practices at conferences andmeetings, nonprofit leaders approach

me with their own secret shortcom-ings, saying that they have no onewith whom to discuss them. Yet itturns out that our shortcomings usu-ally aren’t so secret. My staff was notshocked when I showed them the listof things I suck at, which include

being punctual, thinking throughprocesses, completing administrativepaperwork, and dealing with interper-sonal conflict.

As painful as it may be, though,

when we own up to our weaknessesand strengths, others can better com-plement our

leadership. Once in a managementteam meeting, for example, a VP

asked me about my process for plan-ning an upcoming board meeting. Aswas my habit, I created one on thespot. But my process of creating aprocess frustrated the team. The VPsaid, “Why can’t you just say, ‘I don’tknow, what do you think?’ and let ushelp you create a process?” I thankedher for “driving into my blind spotand honking” – a phrase I’ve come touse when someone steps in to makeup for my faults. Now when I amasked for process, I more likely say: “I

don’t do process. Please suggest one,”instead of inventing one on the fly.

After 14 years on the job, I havewrestled with this and other worstpractices, which are classic foibles not

just of social entrepreneurs, but of allleaders. Here is a sampling:

Fake it until you make it. Early inmy career, I attended a community-

building retreat with staff and partici-pants in our leadership program. As a25-year-old social entrepreneur with

no management experience, I was stillin that “fake it until you make it”period. I thought I was doing a pretty

good job until the facilitator pulledme aside to diagnose the problemwith our community – me.

Apparently, my perfectionist,micromanaging, seat-of-the-pantsmanagement style was creating a cul-ture of fear and dishonesty. I asked thefacilitator how he figured me out, andhe told me my shortcomings wereobvious to everyone. Although I wasshocked and a bit wounded by myunveiling, I was also relieved to stop

pretending. Fortunately, the facilitatordonated his services for many weeks,meeting with my team to help usdirectly address our interpersonalchallenges, understand and value eachother’s work and leadership styles,and learn how to communicate morehonestly and openly with each other.We became a stronger team.

Twelve years and a few dozenteam-building retreats later, I stilldon’t hide my shortcomings verywell, nor do I try to. Instead, I have

learned that when I accept feedback,ask for help, and commit to improve-ment, things are better than when Idon’t own my stuff. Admitting myshortcomings also sets a tone for oth-ers on my team to reveal their vulner-abilities and allows us to build a moreeffective team.

Strive to be liked, rather thanrespected. Leaders like to be liked.We need people to follow us, andwe don’t want to disappoint or upset

them. Social entrepreneurs in particu-lar face skeptics, naysayers, and evenopponents on our road to making social impact. And so we like ourinternal space – our office and staff – to be nice.

But being nice can hurt. I devel-oped a bad habit of avoiding toughdecisions like budget cuts or staff dismissals because I did not want tohurt people’s feelings. Rather than

on the frontlines

www.ssireview.org fal l 2007 / STANFORD SOCIAL INNOVATION REVIEW 23

Worst Practices of aSocial EntrepreneurYou learn more from your mistakes than from your successes by Paul Schmitz

PAUL SCHMITZ is president and CEO of Public Allies, a Milwaukee-

based nonprofit organization that trains young adults from diverse and

underrepresented backgrounds to begin careers in nonprofit and commu-

nity leadership.



24 STANFORD SOCIAL INNOVATION REVIEW / fa l l 2007 www.ssireview.org

preparing people for bad news, Iwithheld information, hoping to pro-tect them while I found the heroicfix. When I couldn’t find the fix,I apologetically “suggested” a deci-sion that no one liked or respected.

In one case, an employee was nota good fit for our organization. Butrather than tell him, I stopped giving him projects. My friendly manner didnot mask my passive-aggressiveactions, and he eventually resigned,

disgruntled. By trying to be nice andnot making the hard choice, I actuallyhurt him more.

A few years ago, a strategy consul-tant sat in on our management teammeetings and helped us build ourdecision-making muscles. We learnedthat although not everyone may haveliked our decisions, we were morerespected, created less conflict, andrespected ourselves more when wemade tough decisions and steadfastlystood by them.

Give freedom first, and then build fences. From the beginning, our orga-nization’s culture prized local leader-ship and local innovation. Believing ourselves to be very progressive, welimited structures, rules, and require-ments. For instance, our supervisorsdidn’t manage. They coached. Weended up with a network of localchapters that created distinct missionstatements, operated alternative pro-grams, opted out of evaluation

processes, and even offered employ-ees different benefits.But in the end, we were a single

501(c)(3). The clash between our cen-tralized structure and our decentral-ized culture grew worse. For exam-ple, one local site signed a lease tomove into a larger, more expensiveoffice. When we disagreed with themove because of the expense and lia-

bility, the local site passionately

argued that we were defying theirlocal autonomy and acting contraryto our own philosophy. Conflicts

between sites only grew as we soughtto standardize our mission, programrequirements, evaluation systems,and operating policies.

To reconcile this clash of cultureand structure, we eventually formeda team of local directors and nationalstaff that created a new operating agreement with explicit standards of

accountability. We realized the hardway what I heard from a Fortune 500CEO: “By building fences up front – clear goals, expectations, and decision

boundaries – you allow people thefreedom to innovate because theyknow their limits and are account-able. It is a lot easier to open a gatewhen people’s performance and inno-vation earns them that right than to

build fences around people who’vehad free rein.”

Say “yes” to everything. For many

years, we believed that strategymeant, among other things, experi-menting with mission-related pro-grams. Our strategy was an opendoor with few parameters for evaluat-ing new ideas or innovations, whichmeant we said “yes” too often. Beforelong, we had an unwieldy network with sites operating new programswith inconsistent activities of varying quality, which compromised our sig-nature program.

In time, it became clear that weneeded to hone our strategy. Weassembled a team, conducted focusgroups, and hired a managementconsultant to help us create a theoryof change – a statement of the prob-lem that we are trying to solve, activi-ties that address the problem, and ourdesired intermediate and long-termoutcomes. Our theory of changehelped us understand that instead of

operating multiple programs, weshould grow our signature program,support alumni of our signature pro-gram, and disseminate our practicesthrough a new consulting arm. Thisnewfound focus helped us expandwithout confusing our brand or com-promising quality. It also taught usthat a good strategy helps an organi-zation say “no” more than “yes.”

The Best Policy

As social entrepreneurs, we often fearthat exposing our weaknesses willhurt our funding. Indeed, many fun-ders communicate – often betweenthe lines – that our mistakes and fail-ures will end their support. Thisencourages dishonesty.

Nonprofits and those who sup-port them benefit much more fromhonest discussions of challenges.Organizations that share their worstpractices can benefit by inspiring public confidence, encouraging

learning and innovation, and building greater trust among leaders andorganizations. Sharing worst prac-tices can also prevent us from rein-venting bad wheels.

In Good to Great , Jim Collinswrites about leaders with both per-sonal humility and organizationalambition. Embracing one’s worstpractices is a great way to beginexpressing that humility. And weak-nesses are not all bad, because often

they are related to our strengths. Peo-ple may struggle with my lack of organization, but they still appreciatemy inventiveness, passion, and drive.

And I may struggle with someone’stype A personality and lack of cre-ativity, but I still appreciate her time-liness and attention to quality. All ourglasses are half empty and half full – none of us can be fully defined byour fullness or our emptiness.

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Worst Practices of a Social Entrepreneur: You can learn more from your mistakes than from your successes