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    Freeingthe Socialentrepreneur

    36 STANFORD SOCIAL INNOVATION REVIEW Fall 2010

    Social entrepreneurS are often reluctant

    to relinquiSh control and create Strong

    leaderShip teamS. unleSS they make thiS

    important tranSition, the organizationS

    entrepreneurS worked hard to create are

    unlikely to Scale or have the deSired impact.

    uzanne Morris , a successful in-

    vestment banker working at Lehman Brothers in New York City, decided to make a signi cant life change by going to work for a small nonpro tthat was poised for growth. She accepted a position as chief operating o cer (COO) of an organization that helps female entrepreneurs growtheir businesses through con dence-building tools and training, a mission that resonated strongly with Morris. She came to the job with a loveof problem solving and a penchant for growing and managing teams as well as a deep admiration for the organizations celebrated CEO.

    During her rst week on the job, Morris learned that she was the organizations fourth COO in a year and a half. 1 Morris was told that she would be responsible for human resources (HR), legal, technology, and board management, as well as responsible for managing everyone except

    By Chantal Laurie Below & Kimberly Dasher Tripp

    Illustration by David Plunkert

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    Fall 2010 STANFORD SOCIAL INNOVATION REVIEW 37

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    38 STANFORD SOCIAL INNOVATION REVIEW Fall 2010

    the controller, who reported to the CEO (and happened to be the CEOssister). Morris felt that if shed survived the rough-and-tumble world ofinvestment banking, she could certainly tackle this challenge.

    Over the next nine months, however, Morris learned that the dy-namic CEO whom she had admired resisted processes and systems,asserted tight control over all details, avoided delegation, felt threat-

    ened by opposing views, and contributed to a negative sta culture. Itseemed that the CEO was not prepared for a strong management teamor aware of the opportunity that having a strong team would present. Although Morris felt that she contributed to the organizations overalldevelopment, she decided that her skills could be better used elsewhereand left. By refusing to relinquish control, the CEO missed an oppor-tunity to fully engage Morris and capitalize on her strengths.

    Awkward leadership t ransitions like this one a re not uncom-mon, particularly when an organization is young and growing fast.

    When this type of transition is handled poorly, it can cause highemployee turnover, low morale, ine cient systems, loss of cred-ibility with stakeholders, and decreased impact. When the transi-tion is handled well, it can help vault a small organization into thehigh-growth phase.

    Instead of resisting change, social entrepreneurs must embraceit at this critical in ection point by creating a leadership team ofquali ed and driven individuals. Ultimately, as a recent BridgespanGroup report put it, augmenting the experience and capabilities ofthe senior leadership team is often the most visible sign of change inorganizations that are becoming more strongly managed. 2 Withstrong management come strong systems, infrastructure, talent de- velopment, programming, and, ultimately, meaningful impact.

    To understand how social entrepreneurs can make the transitionfrom running a start-up to creating an organization that is able toscale up, we interviewed dozens of social sector leaders. From theseinterviews we identi ed the steps that social entrepreneurs musttake to build a team and the ve leadership roles that an organizationmust have for it to be successful at this stage of its development: theevangelist, scaling partner, connector, program strategist, and realist.Before exploring these roles in detail, it is useful to look at one socialentrepreneurs successful e ort to create a leadership team.

    Vis ionsp r ing s exper i ence

    In 2001, Jordan Kassalow, a practicing optometrist, and businesspartner Scott Berrie formed the Scojo Foundation, a nonpro t or-ganization that sells inexpensive eyeglasses to the poor, and ScojoNew York, a for-pro t optometry business. Five percent of ScojoNew Yorks pre-tax pro ts are directed to fund the work of the foun-dation (which in 2008 changed its name to VisionSpring.) Since its

    founding, VisionSpring has trained more than 5 ,200 entrepreneurs, who have sold more than 360,000 pairs of glasses. VisionSpring believes that it can help reduce poverty in the developing world byselling a ordable glasses to tailors, mechanics, artisans, and otherprofessionals who need to see well to do their work.

    In 2003, when the Scojo Foundation was just getting off the

    ground, Kassalow and his then senior director, Graham Macmillan,created a strategic plan that wasnt just about programs, but wasalso about people. We tried to envision the organization ve yearsdown the road, says Kassalow. What management roles will weneed at that point? They drew boxes for each role20 in totaland divided the roles between them. Kassalows positions includedCEO, director of development, director of business development, andcountry manager. Macmillans roles included everything related tonance, sales, operations, and HR.

    The two founders then began the process of shedding roles byasking which jobs we hated the most and were least good at doing,says Kassalow. Over time they chipped away at the boxes, erasingtheir names and putting in the name of a new employee with stron-ger skills in that particular eld. The goal was to have Kassalowsname in only two places: the evangelist box and chief fundraiser box. When Macmillan decided to leave VisionSpring last fall, the boardpushed Kassalow and Macmillan to de ne the skills Macmillansreplacement would need so that Kassalow could continue to shedadditional roles. A job description for the positionnow calledCOO instead of senior directorwas created that highlighted deepnancial, accounting, and people management experience, along

    with multi-sector experience and a certain gravitas. Governmentexperience would be icing on the cake.

    Kassalow lled the new position by hiring Sean Mayberry. May- berry has senior executive experience at Population Services Inter-national, Intel Corp., and the U.S. Department of State. As Mayberrygets settled into his role as COO, Kassalow looks forward to replac-ing his name with Mayberrys in a few more boxes.

    Bui ld ing the t eaM

    It is rare for an entrepreneur to begin thinking about how to build amanagement team as early as Kassalow did. More often, entrepre-neurs put o constructing a management team until they have noother choice. Kassalow provides a model for the steps that socialentrepreneurs can and should take to create a strong leadershipteam that is capable of taking an organization to scale: Recognizethat you can no longer do it all alone; hold frank conversations with your board about the transition; and hire strategically rather thanopportunistically.

    One of the remarkable traits about social entrepreneurs is theirability to play many roles. They care deeply about how their visionis implemented and feel personally invested in the outcome. Socialentrepreneurs are often so involved in all aspects of the organizationthat they end up holding up decision making, losing talent, and cre-ating bottlenecks. At some point, grumblings of dissatisfaction fromemployees or frustrating ine ciencies emerge and need solutions.

    To avoid getting to this detrimental stage, the entrepreneur mustrecognize that he can no longer do everything himself and preemp-tively prepare to let go. Before hiring any high-level managers, he

    C hanta l Laur ie B e low is managing director for strategy, talent, and opera-tions at Teach for America-Bay Area. She began her career as a Teach for Americacorps member in Washington, D.C. Below then served as the manager of fellowprograms at the KIPP Foundation. After KIPP, she joined BUILD, where shelaunched the organizations rst expansion site and served as its West Coastregional director.K imber ly D asher Tr ipp is a program o cer at the Skoll Foundation, whereshe manages grant relationships. Before Skoll, she served as program o cer onthe Henry J. Kaiser Family Foundations entertainment media partnerships team.Tripp began her career as a member of the policy studies team for the UnitedNations Association of the United States of America, building its program on post-con ict peace building and the rule of law.

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    Fall 2010 STANFORD SOCIAL INNOVATION REVIEW 39

    needs to assess his own strengths and weaknesses honestly. Socialentrepreneurs must ask themselves questions such as What do Ienjoy doing? What am I really good at doing? What am I not goodat doing? What kind of people do I need around me?

    Board members play a particularly important role at this stage ofthe process. They should instigate conversations with the social entre-

    preneur about building strong, talented management teams, preparingfor leadership succession. To ensure that this happens, entrepreneursshould ll their board with opinionated members who bring skills,networks, and experience to the organization. Entrepreneurs mustuse the start-up stage as an opportunity to build trust with boardmembers and ensure that board members are invested in the visionand long-term sustainability of the organization. This trust enablesentrepreneurs to heed advice that can often feel personal or be dif-cult to hear. Strong boards help entrepreneurs grow comfortable

    with dissenting voices, challenged ideas, and evolving roles.Entrepreneurs should map out their senior management hires

    ahead of time. Too often, they see an oncoming cash ow crisis andhire someone with an accounting background, or decide they are over- whelmed with direct reports and hire a COO. Social entrepreneursare often encouraged or forced to get a person or a skill set in imme-diately, says Sally Osberg, president and CEO of the Skoll Foundation.They often go into it feeling cornered. Kevin Flynn, director of cli-ent services at Commongood Careers, sees this behavior frequently.

    We hear, I need someone who is an entrepreneurial CFO and can dotechnology and fundraising and also code in Java, says Flynn.

    The Leade r sh ip Team

    Once the social entrepreneur has spent time in honest self-re ectionand frank board discussions, its time to create a new leadership team.The entrepreneur must approach leadership team development withthe same thoughtfulness and determination that he applies to creat-ing his vision or he risks making the wrong hires.

    Our research indicates that there are ve essential leadershiproles in an organization that is ready to scale up. These roles mayor may not be lled by ve separate people; in some cases multipleroles can be lled by one person. The ve roles are the evangelist,scaling partner, connector, program strategist, and realist.

    Evangelist

    The most important member of the leadership team is the evange-list the person who is deeply passionate about the organizationsmission and convinces others to help ful ll it. When the founderis still at the organization, he is the person who lls the role of theevangelist. If the founder has been replaced, it is the entrepreneur who is running the organization (often with the title of CEO, presi-dent, or executive director) who becomes the evangelist.

    The evangelist has a number of responsibilities. First, he is the or-ganizations visionary, continually re ning its mission and strategyand making sure that priorities are established and met. He needs toshare his vision with people inside and outside of the organization, es-pecially with the leadership team. Willy Foote, president and founderof Root Capital, explains that the evangelist is going to see new op-portunities that may not t with the current organizations strategy,and his role is to get the team to believe in the value of disruption,

    while being very cautious to court disruption not destruction.The evangelist also maintains the organizations culture. For ex-

    ample, when Mike Feinberg, cofounder of the Knowledge Is PowerProgram (KIPP), served as CEO of the KIPP Foundation, he ensuredthat each conference room held the name of a childrens book thatheld signi cance on the KIPP school campuses. All new hires learned

    the symbolism of these books and embraced the metaphors asso-ciated with them. For example, The Polar Express represented themessage that all KIPPsters (students who attend a KIPP school)can hear the bells even when naysaying communities, peers, oradults try in vain to convince them that college is not an option.Each evangelist will choose a di erent way to keep the organiza-tions culture alive, but he needs to be the person who constantlyreminds others of the importance, characteristics, and values ofthe organizations culture.

    The evangelist is also the external face of the organization. Peo-ple want to understand the evangelists underlying motivations forleading the organization and be captivated by the organizationsfounding story and long-term vision. The evangelist can skillfully weave together the organizations mission and programs with sto-ries that express it in personal terms in order to truly evangelizeand convert nonbelievers.

    Scaling Partner

    The second role that is required is the scaling partner . This person isthe organizations pragmatist, someone who can think strategicallyand make the evangelists vision a reality. Sometimes this positionis called the COO, and other times the deputy or managing director.The scaling partner must enjoy creating and managing systems thatimprove organizational e ciency, as well as creating systems that al-low sta members to enjoy their jobs and feel valued and rewarded.

    A lot of organizations are looking for entrepreneurial people whocan build the plane while ying it, says James Weinberg, founderand CEO of Commongood Careers. But at [the scaling] stage, theyactually do need someone to just build the plane. Or as Osbergsays, the scaling partner is someone who can unleash the produc-tivity of the organization by ensuring that people spend their timein the right way.

    Erin Ganju, former COO and current CEO of Room to Read, isa good example of a scaling partner. In 2001, Ganju rst o ered tohelp founder and executive chairman John Wood manage his bur-geoning organization. Wood recognized right away that Ganju was agood potential scaling partner because she could think big, yet wasalso detail oriented and enthusiastic about tasks that he didnt likedoing. Before joining Room to Read, Ganju had worked as a prod-uct line manager at Unilever and as a nancial analyst at GoldmanSachs. She immediately put her strong project management skills touse at Room to Read. She helped develop a strategy for entering newcountries, formalized program design, and helped channel Woodsfundraising talents into speci c programmatic areas. Ganju enjoyedmanaging operations, talent, and processes while Wood preferredpublic speaking, fundraising, and building a worldwide network ofallies. Ganju was the perfect scaling partner for Wood.

    As crucial as the scaling partner position is, it is also the mostdelicate and controversial of the ve roles. At its worst, the position

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    can become what Gretchen Anderson, former directorof business development for On-Ramps, calls a dump-ing ground for the CEO. The role of the scaling partner works only when it is a y in and yang match with thefounder, a true partnership stemming from trust andleadership. The scaling partner should be the rst per-

    son the founder hires on the leadership team so that hecan be a sounding board for all future hires.

    Connector

    The role of the connector is to ll in the gaps left by theentrepreneur as he focuses on being the evangelist. Tra-ditionally, this position might be called a vice presidentor director of development. It is also akin to the rolethat the chief of sta plays for a politician, maximizingthe politicians time and ensuring access to importantpeople. The connector makes sure that the evangelistis speaking to the right audiences at the right timeand capitalizing on all opportunities. In addition, theconnector ties development e orts to programs andmanages existing funding relationships, freeing theevangelist to spend time on other activities.

    Even with these clearly de ned responsibilities, theconnector role can con ict with the evangelist, particu-larly in the area of fundraising, and cause tensions ifthe roles arent clearly de ned. Donors are the lifebloodof the organization, and having more than one personmanage those relationships is risky. Even though it isdi cult to divide these roles, it is important that it bedone so that the organization can grow.

    Je Berndt, a partner at New Pro t Inc. who over-sees investor relations, communications, and fundrais-ing, is a good example of a connector. Berndt has fourprimary responsibilities. The rst, which he describesas wearing out the soles of my shoes, is meeting reg-ularly with a variety of constituents to build the NewPro t network and deepen its long-term relationships.The second task is to make sure that Vanessa Kirsch,New Pro ts president and founder, meets with the rightpeople. Vanessa is gifted and has great instincts; ourteam has to Navy SEAL her in and out to maximizeher impact. The third task is to make sure that the managementteam, and ultimately the entire sta , has the tools they need to sellthe organization. The fourth and nal task is to build the fundrais-ing team, a complex operation that caters to the needs of the entireorganization.

    Program Strategist

    All organizationswhether they are focused on education, health,or climate changeneed a program strategist who is an expert inthat particular eld and whose role is to ensure that the programsachieve the desired outcomes. The program strategist not only hasissue area expertise, but also understands how the programs areimplemented in the eld. This role brings credibility and expertiseto the organization and its programs that may not have existed.

    The program strategist not only looks at how programs are run-ning day-to-day, but also thinks about how the innovation can bescaled up, diversi ed, and perfected. Foote describes the programstrategist as the sacred ame of the organization, responsible forcreating a bridge between the reality of the programs and the visionof the evangelist. Without a program strategist with a strong voice onthe leadership team, an organization can stray from its mission andend up scaling programs that do not produce the desired outcomes.

    Ajuah Helton, the rst chief program o cer at BUILD, a four- year college preparation organization, is a good example of a pro-gram strategist. In 2007, BUILD evaluated a students performancesolely on his grade point average (GPA), dismissing students below acertain threshold. The policy was intended to honor the programsacademic rigor and motivate students to perform better in school.

    the leaderShip teamYou know youve got the right person lling a leadership role when

    EVANGELISTn He secures a $35,000 donation from a philanthropist who happens to be sitting next to

    him on a ight from Los Angeles to Phoenix.n She has a purse cluttered with business cards that rarely get loaded into Outlook, but

    she can remember each encounter with uncanny precision.n He can convince skeptics not only of the value of what his organization is doing, but also

    why the issue is critical, converting skeptics into believers in just minutes.n She sends one-line e-mails at obscure times of the day and night, many of them ending

    with This is why what we are doing is so important!

    SCALING PARTNERn She keeps a color-coded to-do list and sometimes adds tasks that have already been

    completed in order to maximize the ultimate grati cationcrossing an item off the list.n He has dog-eared copies of the books Good to Great and The Leadership Pipeline and has

    the quote Get the right people on the bus on a Post-it note on his computer monitor.n She often asks for data to back that up, speaks in bullet-pointed lists of three, and

    ends most conversations with a summary of time-speci c next steps.n He asks the founder, after an inspiring proclamation of a new strategy to scale up,

    Have you thought through how this will affect our resources and strategic plan?

    CONNECTOR

    n He sees weddings, reunions, and neighborhood block parties as ideal opportunities toexpand his professional network and share the work of the organization.n She has more than 500 connections on LinkedIn and adds two to ve more connec-

    tions each week, frequently putting them into such categories as potential partnersand advocates.

    n He uses colored tabs to indicate which events are most important for the evangelist toattend and can be seen walking the evangelist to her car telling her the three e-mailsshe should respond to that night.

    n She speaks on a rst-name basis with the baristas at her local Starbucks and once sentowers to her hairstylist after she had a baby.

    PROGRAM STRATEGISTn She weaves words like rubric, metrics, and outcomes into regular conversation.n He subscribes to academic journals and frequently sends out links to articles or videos

    with compelling data such as the latest statistics on micro nance repayment rates.n She displays a framed photo at her desk of the rst class of students she taught and

    the family she lived with in Guinea Bissau while serving in the Peace Corps.n He programs his of ce voice mail to ask that people call him on his cell phone be-

    cause he is in the eld observing the organizations programs.

    REALISTn He uses Excel to help organize his thoughts, even when he is not using any numbers.n She brings a copy of the budget to every executive meeting.n He begins to research international standards for audited nancial statements as soon

    as he hears the evangelist talk about expanding operations into a new country.n She has a note on her desk reminding passers-by to Think Unrestricted when fundraising.

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    The problem with this policy is that it often ended up dismissingthe very students BUILD was designed to help, sometimes in theirsenior year of high school. As chief program o cer, Helton analyzeddata and collaborated with sta to create a new way of evaluatingstudent performance. The result was the BUILD score. Instead of judging students solely on their GPA, the team also began evalu-

    ating students on other characteristics, such as commitment andpassion, which served as strong indicators for longer-term successand better supported BUILDs theory of change. Without Heltonsextensive experience in education, credibility with the team, andoverview of trends, BUILD ran the risk of scaling e orts that wouldhave reduced the organizations impact.

    Realist

    Every organization needs someone on the leadership team who playsthe role of the realist , the person who keeps the organization groundedin nancial reality. This person is often called the chief nancial o cer(CFO). Placing the nancial function on equal footing with other seniormanagement roles ensures consistency, practicality, and coordination within the organization. The nance person is the bedrock position,says Jim Fruchterman, founder and CEO of Benetech. He or she in-serts a culture of frugality and ethics, accountability for nancial results,and reality. The realist is more than a nancial o cer, he is also theperson rolling up his sleeves and minding the store.

    The importance of having a strong and skilled realist is dem-onstrated by the traumatic series of events that a New York-basednonpro t recently underwent. 3 The organization had 26 interna-tional o ces, almost 90 sta members, and only two accountants.The board, evangelist, and scaling partner all understood the needfor a realist, so they hired an executive from a leading New York lawrm. The person had experience managing nancial operations ata for-pro t, but he was not a certi ed public accountant (CPA), hadnever run nancial operations at a nonpro t, and had never directlymanaged accounting. For almost a year he claimed to be revamp-ing the nancial systems and yet very little changed in practice.Because of a host of internal oversights, the organization did nothave the systems to distinguish unrestricted from restricted funds,double-dipped into reserves because of inadequate and decentral-ized expense management practices, and raised new grants withouthaving adequate overhead to meet expenditures.

    In February 2009, believing that the organization was $5 millionin debt, the vice president of nance nally explained the nan-cial crisis to the president of the organization (the evangelist). Inshort order, an interim CFO who had a CPA and strong accountingskills was hired. She personally audited the organizations booksand traveled to every regional o ce to x nancial systems andexpense practices and to institute cost-cutting measures. A recentexternal audit shows that the organization is about $2.5 million indebt. The organization will likely survive because of the strengthof its programs and reputation, new leadership and systems, andcommitted and generous donors. Its long-term future will be de-cided by how the board and management team navigate the nextsix months. As this example shows, organizations with world-classprograms, visionary founders, and strong partners can su er dra-matic setbacks without a talented realist.

    other considerat ions

    The ve roles describe the skills needed in a successful leadershipteam. These roles may overlap, however, and may not always be held by a single person. For example, Julie McGuire, director of develop-ment at Spark, currently plays both the realist and connector roles.By owning cash ow and revenue projections for the organization,

    McGuire is able to connect development directly to the internalfunctions of the organization. Another example is Mayberry, whoplays the realist and the scaling partner roles at VisionSpring, re-sponsible for all internal operations, including managing talent,performance, nancials, and operations.

    There are other roles besides these ve that may be needed in aleadership team as the organization grows. Marketing o cers, chieftechnology o cers, or chief people o cers often appear in organi-zations that have passed the rst major in ection point and are em- barking on another scaling push. These roles are valuable, but can becombined with other positions or outsourced until the organizationcan a ord to have unique positions created. The ve principal roles,however, cant be outsourced or compromised when developing aleadership team for an organization poised for growth.

    Although our research and interviews focused on social entre-preneurs, many of our ndings can also be applied to for-pro tstart-ups. Googles Eric Schmidt, for example, could be describedas a scaling partner to founders Larry Page and Sergey Brin, eventhough Schmidts o cial title is CEO. Schmidt brought sound business pract ices to complement the creative and technical ge-nius of the founders. The connector role at a nonpro t, to citeanother example, is similar to the vice president of marketingand sales position at a for-pro t. Both require someone with ex-tensive networks and the ability to help strategically position theorganization and its CEO. And it goes without saying that the re-alist plays a critical role in the for-pro t sector where the bottomline is measured in dollars and cents and serves as the ultimateindicator of a companys success.

    When social entrepreneurs understand their strengths and pri-orities, and develop a leadership team composed of people with dis-parate and complementary skills, it creates what Wood calls theperfect combination. In a note of caution, however, Wood pointsout that if you only have a lot of corporate refugees who know strat-egy and process, they can scale like champions, but you wont havedeep programs. Conversely, if you only have a lot of programmaticspecialists with nonpro t backgrounds, your programs are incred-ible, but they dont scale. The solution, Wood continues, is to nd your perfect combination and scale the heck out of it. When socialentrepreneurs stop thinking of leadership positions as simply a so-lution to an immediate problem, and begin to create roles and hiretalent with the same vision and foresight that they use to perfecttheir idea and mission, scale becomes a natural progression ratherthan an elusive goal. n

    N o t e s

    In the interest of privacy, Suzanne Morriss name has been changed and the name of1the organization has not been revealed.

    Daniel Stid and Je Bradach, Strongly Led, Under-Managed, The Bridgespan2Group (July 2008): 7.

    Names are not included here by request of the organ ization.3

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    Reproduced withpermission of the copyright owner. Further reproductionprohibited without permission.