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 First Thing’s First
Charles and Lynn Schusterman Family Philanthropies and Rockwood Leadership
Institute recently embarked on a journey to learn about the effectiveness of our
flagship fellowship programs.

We each independently collaborated with the research firm Learning For Action
to take a deep dive into the Schusterman Fellowship and Rockwood’s successes
and shortcomings.

Naturally, we were a little nervous about what we might discover. Did our
program curricula strike the right balance between conceptual and experiential
In 2021, our organization’s brand name changed to Charles and Lynn Schusterman Family Philanthropies. learning? Did our participants feel equipped to make a difference in their fields?
This resource was created prior to 2021 and has been updated to reflect our name change.
Had our efforts paid off in tangible ways?

Schusterman Fellowship
The findings from both evaluations illuminated the areas in which our programs
The Schusterman Fellowship, an initiative of Charles and Lynn Schusterman
are succeeding, which you will read more about in this guide.
Family Philanthropies, is a global leadership development program for individuals
who are committed to growing their capacity to exercise leadership in the Jewish
community. It is designed to help strengthen a global Jewish ecosystem by investing
But the results also forced us to be vulnerable and face, head-on, the areas
in exceptional professionals capable of building highly effective organizations and
attracting the best and brightest talent at all levels. in which we could improve. Since the evaluation, both the Schusterman and
the Rockwood teams have been working to strengthen our programs based
Learn More »
on the findings.

Rockwood Leadership Institute As we engaged in this work, we realized that we could learn from each other’s
Rockwood was founded in 2000 to fill a specific niche within the social change experience and from others in the leadership and talent field. In that spirit, we
movement by providing powerful and effective training in leadership and
collaborated to find the common threads in our evaluations.
collaboration to nonprofit and philanthropic leaders, organizations and policy-
change networks. Today, Rockwood has more than 6,000 alumni (of which 68%
are women and 52% people of color), making it the nation’s largest, most diverse
provider of multi-day leadership trainings for the nonprofit community.

Learn More »

Written by Alison Spasser

1
 This guide is a collection of five findings supported by both evaluations, along Empower Leaders. Change Organizations.
with illustrative stories and examples that we hope make them more concrete
and actionable. It is not necessarily a reflection of everything we have gotten Transform Your Sector.
right, but rather the most essential elements of what makes our programs
effective—a distinction we feel is important to note.
Sounds like a tall order. But if you are looking to build a cutting-edge
leadership development program, chances are you already have your eyes set
So what improvements have we made since these evaluations?
on achieving lasting progress in your field…and you recognize that it all starts
with shaping strong, talented leaders.
The Schusterman team is taking significant steps to increase racial, ethnic and
geographic diversity within cohorts. We are also developing ways to help Fellows
But what does that actually mean in practice? What will it take in time, resources
bring their learnings to the workplace and follow through on their real-world
and people power to spark change in your sector? What curricular components
plans to bring change to their sectors and communities.
will inspire personal and professional growth in your participants? How can you
help these leaders share their struggles and forge meaningful relationships?
Rockwood Leadership Institute is investing in alum engagement by hosting local
How can you ensure your program’s impact lasts well beyond its conclusion?
gatherings and increasing our presence at conferences and events. We’re also
exploring new locations and models for our programs to help more people and Without a solid foundation of research to build on, answering the questions
organizations take advantage of our curriculum. above can be overwhelming. And unfortunately, little evaluation exists in the
leadership field to guide your decision-making.
We certainly don’t have everything figured out, but we sincerely hope that
you can glean helpful information from our experiences to maximize the To help fill this void, we decided to assess the leadership programs at our
effectiveness of your leadership and talent initiatives. respective organizations—the Rockwood Learning Institute (Rockwood) and
Charles and Lynn Schusterman Family Philanthropies—and get to the bottom of
Let’s get started! what works and what doesn’t.

2 3
Rockwood and the Schusterman
Fellowship are committed to
creating leadership development
experiences grounded in diversity,
equity and inclusion because we
believe these values are critical Now, we want to share the findings with you. Key Recommendations
to developing successful leaders.
Rockwood and Schusterman Family Philanthropies enlisted
Rockwood has been a pioneer in
the help of Learning for Action (LFA), a strategic evaluation Set the Stage for Vulnerability
this space, and Schusterman is
group that partners with social change organizations to assess Before you can help your participants hone their skills, you have to set the right tone
learning from Rockwood’s deep
experience building cohorts programs, identify areas for growth and chart a course to a to help them share struggles, illuminate strengths and embrace vulnerability.
that reflect the full spectrum of longer-term organizational impact. LFA took a deep dive into Read More »
diversity—including race, ethnicity, both Rockwood’s leadership programs and the Schusterman
gender identity, sexual orientation Fellowship, gleaning valuable insights from program alumni Focus on Emotional Intelligence
and disability—to represent our
through comprehensive surveys and wide-ranging interviews. For leaders aspiring to make a difference, looking forward requires looking inward—and
communities at large. While we
do not include strategies for that means focusing on qualities that rarely get the spotlight in professional development
LFA’s in-depth analyses illuminated areas for improvement programs: mental, emotional and spiritual awareness.
building diverse cohorts and
equitable programs in this within our programs—but they also highlighted key successes Read More »
guide, we provide resources that demonstrate the effectiveness of the leadership
for exploration on page 29. development models employed by the Schusterman and
Be Intentional About Relationship-Building
Rockwood Fellowships. According to the program surveys:
Your participants have diverse backgrounds and hectic schedules, which means you will
have to be intentional about providing ample opportunities to connect, forge bonds and
• 94% of Schusterman Fellows report an increase
learn from one another.
in professional responsibilities, and nearly half have
Read More »
received promotions since the conclusion of the program.
Furthermore, 100% of Fellows say their new peer network
Design the Right Coaching Experience
is one that supports and enhances their personal and
Most leadership programs use coaching to help participants strengthen their skills.
professional growth.1 Read More »
But creating quality coaching experiences can be complicated and costly, and not all
• 98% of Rockwood Fellows say they now deal more effectively approaches are created equal.
with leadership challenges, and 90% report that the program Read More »
had a transformative impact on their lives. LFA also found
that 87% of Rockwood Fellows said they now have a clearer Encourage Sector and Cross-Sector Collaboration
vision for their work.2 Read More » If your program is going to help address the sector-wide challenges that inspired its creation
in the first place, you will need to show your participants the value of working together.
In this resource, you will find our learnings distilled into five key
Read More »
recommendations designed to help you achieve similar success,
all while shaping and supporting leaders as they tackle the
challenges facing your field.

5
Set the Stage
for Vulnerability
Paving the way for growth means breaking
down barriers and building up trust.

This may sound familiar: You have taken time out of your busy schedule to
attend a professional development event, eager to learn from contemporaries
in your field. While you may glean some useful tips and tricks, when the
time comes to dive into the issues that matter, you hesitate. Is it safe to
challenge someone else’s viewpoint? Are you comfortable enough to admit
a professional weakness to a room full of experienced peers?

If that scenario rings a bell, you know firsthand the frustration participants
feel when a development opportunity fails to deliver. Now that you are
building your own program for high potential leaders, it is up to you to
ensure that your participants can be vulnerable (and therefore, honest)
in discussing their strengths and struggles—with both program faculty
and each other.

When building an effective leadership program, it is important to lay the

groundwork for participants to forge strong bonds—without it, efforts
to engage them on a deeper level will fall short. Devoting organizational
resources to creating an environment where it is okay to admit failures,
express fears, ask questions and engage in constructive debate is critical
to achieving tangible results during and after the program.

7
Embracing vulnerability can pay
dividends. One Schusterman
Strategies to Encourage Vulnerability Vulnerability in Practice

Fellowship participant said, “I am When developing your approach, consider these six When it comes to breaking the ice, storytelling is one of the most “I am so much more
so much more self-aware. I know powerful tools at your disposal.
strategies to enable vulnerability and build trust: self-aware. I know
my strengths and weaknesses, and
I am very comfortable speaking
START EARLY. Dedicate time at the beginning of your program
At their initial in-person gathering, new Schusterman Fellows my strengths and
about things I am struggling with share four photos that they feel represent their leadership
to my boss. I feel like I can be to getting everyone together in person—an especially important progression and narrate their personal journey to their peers.
weaknesses, and I
vulnerable and that vulnerability undertaking if participants are geographically diverse and cannot Often, these photos illustrate profound moments of crisis, failure am very comfortable
feels like a source of strength.” meet regularly. or loss, helping participants become more comfortable with each
other—and with being vulnerable—right off the bat.
speaking about things
BE ROLE MODELS. Trust starts at the top. If vulnerability is the I am struggling with to
In another helpful activity, Schusterman Fellows take turns
94% of participants in Rockwood goal, program faculty should be willing to be vulnerable, too.
completing the sentence, “If you really knew me, you would know...”
my boss. I feel like I can
leadership trainings said that Join group discussions, address common concerns up front and
they are more willing to have
As the exercise progresses through multiple rounds, participants be vulnerable and that
show participants that it is okay to let their guards down. become more comfortable in their vulnerability and their responses
a “courageous conversation”
become deeper and more meaningful.
vulnerability feels like a
as a result of the program.
Said one alum, “It was a very
SET THE TONE. A little bit of structure goes a long way. source of strength.”
Before participants dive into the substance of the gathering, One popular Rockwood icebreaker activity, called “Who are your
vivid experience to see the
people?” asks participants to describe qualities shared by the
improvement in confidence and help them establish a mutually agreed-upon set of guidelines,
important people in their lives and those they gravitate toward both
happiness and centeredness or “agreements,” that will steer their interactions—including
personally and professionally. Rather than asking participants to
among people in my cohort from how to engage in respectful dialogue.
discuss their backgrounds point-blank, which would likely result
retreat to retreat. We really opened
in them outlining their résumés, this activity allows participants to
up to one another and shared our
BREAK THE ICE. First-time meetings can be awkward, which bypass formality and tap into something much more personal.
challenges in the first retreat. By
the second retreat, at the opening
means you need to be aggressive in helping participants cut
through formality from the start. Guide them through a series Even deeper emotions tend to surface during Rockwood’s “How do
circle, everyone was standing
you lie?” exercise, in which pairs explore all the ways they deceive
taller and was more confident of icebreakers designed to set the stage for deeper learning.
themselves or the people in their lives—an intense and cathartic
in their leadership.”
experience that participants often remember as a turning point in
PRIORITIZE DIVERSITY. When dividing participants into groups,
their journey to embrace vulnerability.
ensure they contain people of different roles, titles, identities,
While embracing vulnerability demographics, interest areas and life experiences. Diversity However, it is Rockwood’s “vision stands” exercise, during
means stripping away barriers and
means exposure to new perspectives and opportunities for which each participant stands in front of the group and speaks
baring insecurities, the intended for two minutes, that serves as an even more powerful example of
people of different backgrounds to find common ground.
result is increased confidence in vulnerability in action. Speakers must calmly and confidently accept
one’s abilities and potential. One the applause and cheers they receive from their peers without
Schusterman Fellow referred ENCOURAGE SKILL SHARING. By allowing participants to
looking away, hiding their faces, sitting down or deflecting with
to his increased self-belief open up about their individual strengths and weaknesses,
humor—a more difficult task than it seems!
as “quieting his imposter,” a you demonstrate the value of this new peer network as a safe
reference to imposter syndrome, sounding board for ideas and a strong mutual support system
a common phenomenon in which
when coping with professional challenges. Encourage a culture
individuals—no matter how much
of candidness, sharing and reciprocity, in which participants
they achieve—fear that they are
coach their fellow network members in their areas of expertise
not as skilled or knowledgeable as
others think they are and that any and are unafraid to pursue opportunities to be coached by others.
slip-up will expose them as frauds.

8 9
Focus On Emotional
Intelligence
Creating strong leaders means helping them
understand what drives their actions.

Take a moment to envision a leader you admire. How does this person take
charge in a professional setting? What inherent strengths does this person
possess? What particular skills does this person have that you value?

Have you painted a mental picture of compelling public speaking, deftly-

balanced budgets, technological acumen and other “hard skills” that
demonstrate hands-on, practical expertise? Or, does your ideal leader
demonstrate qualities that are more intrinsic to their character—and
far more personal?

Time and time again, when groups of professionals are asked to describe
leaders they admire, qualities associated with emotional intelligence (EQ)
—being aware of, harnessing and expressing emotions in constructive
ways—are mentioned before hard skills.3

Building a comprehensive leadership program demands a focus on what makes

effective leadership possible in the first place: mental, emotional, spiritual and
physical awareness. Without these core competencies, leaders may struggle
to guide staff through crises, get buy-in from stakeholders or highlight their
colleagues’ strengths.

If you fail to emphasize the underlying emotional responses, beliefs, values and
fears that drive behavior, your program’s impact will be short-lived.

11
In addition to more practical
skills, effective leaders value
Strategies to Encourage Emotional Intelligence in Practice

what’s on the inside. As one Emotional Intelligence Rockwood participants gain practical experience in navigating “I am truly a more impactful
Rockwood participant put complex emotions right away. Immediately after learning about
it, “Rockwood helped me When exploring ways to make emotional intelligence ways to manage triggering situations, they are given the results
leader in all aspects. I have
understand what I internally an essential building block of your program, consider of their 360-degree leadership evaluations, which highlight both deepened my listening skills,
bring to the fight—and how
these strategies: strengths and areas for improvement. Confronted with this
those things can both help and multifaceted feedback and constructive critique, participants
expanded my knowledge
hinder how I want to show up.
HELP THEM LOOK INWARD. Emotional intelligence should be more
may experience negative emotional responses and can then on subjects of leadership
Through that understanding, put learned concepts to work.
I’ve been able to build stronger than just the subject of a single training. It should be the foundation of and beyond, and pushed
your curriculum. The emotional and mental components of leadership
relationships, articulate a sharper Likewise, Schusterman Fellows undergo a 360-degree myself personally to take
vision and build more alignment are often dismissed as “soft skills,” so it is up to you to legitimize leadership assessment, the Leadership Circle, which helps
around our shared goals.” them by employing clear, consistent terminology from the start. them to understand their greatest gifts as a leader, what gets
more risks with greater
in their way and how their thought habits translate into confidence.”
productive or unproductive styles of leadership.
KEEP THINGS PRACTICAL. Talking about mindfulness and spirituality
Four out of five Schusterman can get abstract, and their real-world applications can get lost in
Schusterman Fellows are also shown the importance of achieving
Fellows reported that as a result the ether. Make sure that your participants are taking away concrete
emotional awareness by participating in an exercise in which they
of the program, they “feel more
strategies to put these concepts to work, at work. For instance, are asked to list “states of mind” on a scale from -3 to +3.4 For
fulfilled physically, mentally,
practical strategies can include allotting regular windows during the example, -3 might include words like “depressed” or “depleted,”
emotionally and spiritually.”
workday to reflect or identifying ways to best isolate and diffuse and +3 might includes words like “elated” or “euphoric.” When
One Fellow said, “I am truly
workplace scenarios that trigger emotional responses. they examine domains of leadership such as strategic planning
a more impactful leader in
or collaboration through this lens, they discover that +1 and +2
all aspects. I have deepened
are the states of mind that lead to productivity and effectiveness.
my listening skills, expanded SHOW, DON’T TELL. Using emotional intelligence in their professional
They also realize that +3 can be just as detrimental as -3 states of
my knowledge on subjects of lives will be a relatively new idea for some and difficult to replicate
mind. Further, they learn that emotions are not necessarily positive
leadership and beyond, and
without witnessing it firsthand. Ensure that coaches and facilitators or negative; they are inevitable, constantly changing and can be
pushed myself personally to
are not only familiar with the principles of emotional intelligence, but shifted through a leader’s awareness and actions.
take more risks with greater
can effectively model it for participants during one-on-one and group
confidence.”
sessions.

DIVERSIFY THEIR LEARNING. Everyone absorbs information

differently, and opportunities to self-reflect should employ a wide
variety of learning styles. Try exercises that involve internal reflection
(journaling, meditation or art), performance (improv and role-playing)
and informal sharing (paired activities and group discussions).

12 13
Be Intentional About
Relationship-Building
The more opportunities for discussion
and learning, the better.

Does it seem like your calendar is more jam-packed than ever these
days? You are not alone. In today’s rapidly-evolving work culture,
professionals at every level are required to juggle many priorities.
Unfortunately, that means your program is just one of many things
competing for your participants’ attention at any given time. The bottom
line: It is not enough to simply sow the seeds of a solid peer network—
you have to cultivate it as your program progresses.

A participant network needs consistent engagement to keep

relationships flourishing. This is an especially tricky proposition if your
participants are scattered geographically.

While in-person gatherings are ideal for fostering intimacy, you cannot
rely on a handful of face-to-face meetings to do all the heavy lifting,
and you cannot expect participants to forego personal and professional
responsibilities for frequent travel. You will have to take advantage of
digital communication tools for your network to thrive.

15
Rockwood participants and
alumni enjoy regular check-ins,
Strategies to Encourage Relationship-Building in Practice

peer coaching opportunities, Relationship-Building The Schusterman Fellowship includes access to monthly professional “The network of leaders
online and in-person gatherings learning sessions via Zoom. Faculty keep sessions open after the
within and across cohorts and To keep the momentum going during and after formal training concludes so participants can discuss ways to put the
that I am part of – it’s like
access to active email listservs. the program (while also conserving budget and concepts they just learned to action in their professional lives. Each is we ‘know’ one another in
This frequent engagement
resources), consider the following strategies: led by a Fellow and serves as an effective way to maintain existing peer
pays off: 84% of respondents relationships and facilitate the formation of new ones. In addition, Slack,
very profound ways and
build and maintain stronger
CONNECT VIRTUALLY. With minimal organizational investment,
a digital work collaboration platform, is used for easy communication are connected at a very
interdependent relationships between and within Fellowship cohorts, allowing participants to share
as a result of participation your program can use powerful online tools like Zoom, Slack
personal news, professional tips and helpful resources.
deep level.”
in Rockwood programs. One and WebEx to regularly bring participants together for group
alum said, “The network of discussions, professional learning and networking. Digital It is at in-person gatherings, however, when the deepest bonds are
leaders that I am part of—it’s communication can feel impersonal, so make sure that you formed. At their closing gathering, each Schusterman Fellow uses
like we ‘know’ one another in a “design-thinking approach” to create an award for one of their
facilitate smaller group discussions and use video-based
very profound ways and are colleagues, honoring them for the strengths they brought to
technology that lets users see each other.
connected at a very deep level.” the group.5

ENCOURAGE LOCAL LEARNING. Virtual tools are necessary

Schusterman Fellowship alumni are dubbed “Senior Fellows” when the
for building a strong network and keeping participants actively program concludes and gain access to webinars, book club discussions
Program alumni should be engaged, but engagement can—and should—go deeper. and “collaboration grants” for those looking to partner with other
engaged in the program long
Encourage those who live in the same city or region to meet Fellows to tackle key challenges in their sector. The Fellowship staff
after it ends—and the transition
up in person, attend professional events together or lead also call upon Senior Fellows to serve as mentors and facilitators
should be as seamless as possible.
for new participants—meaning bonds are forged both within and
For example, alumni of the training sessions.
across cohorts.
Schusterman Fellowship are
referred to as “Senior Fellows,” PRIORITIZE ALUMNI. The network you built should be actively
The Rockwood program nomination process is designed to ensure
a manifestation of the program’s maintained long after participants become alumni. It is simply candidates are ready to become active, valuable members of the
philosophy that the Fellowship
not enough to leave alumni to their own devices. Without participant network. Before the first session, each new Fellow tells
is an ongoing personal and
program faculty providing coordination, it can be all too easy Rockwood which of their cohort members they already know. Staff
professional community. These
for the busy schedules of your alumni to get in the way of then use this information to pair participants up with people they
Senior Fellows are given regular
don’t know for icebreaker activities. When the session is complete,
opportunities to connect, both preserving their burgeoning peer relationships. Be sure to
a new question is posed: Who do you know now? A map of the
online and in person. take the lead in organizing alumni events, especially in the
cohort’s burgeoning network is drawn, demonstrating visually
months following your program. For more information about
the new connections that were forged during the session.
alumni engagement and actionable strategies for developing
a comprehensive approach, read the Schusterman’s Alumni For Rockwood Fellows, opportunities to build and strengthen
Playbook. relationships are always within reach—whether it is an activity
as simple as eating a communal meal or something as intensive
as participating in a multi-day residential training specific to
PROMOTE CROSS-COHORT SHARING. A great way to keep
their area of the country. Rockwood programs also provide access
alumni in the loop is to encourage interaction with your
to highly active listservs that participants across cohorts can use
current program cohort. Not only do these experiences keep
to connect with each other.
your alumni engaged with you, but they serve as mutually
beneficial learning opportunities for both past and present
participants—allowing both groups to gain new perspectives
and build valuable professional relationships.

16 17
Design the Right
Coaching Experience
Give your participants the support they need
to succeed—and tackle it from multiple angles.

As anyone who has tried (and failed) to uphold even the smallest New Year’s
resolution will tell you, change is hard. Bettering yourself requires a healthy support
system of friends, family and co-workers. As your participants work to expand their
leadership potential, it is up to you to provide them access to the guidance and
encouragement they need to ensure that the impact of your program is long-term.

That’s where coaches come in. Often the bread and butter of leadership
development programs, coaching is a partnership between a trained coach
and a client with the goal of maximizing the client’s potential.6

Its efficacy should not surprise you. Coaches serve as key teachers, mentors,
motivators, cheerleaders and sounding boards, able to adapt to an individual’s
unique strengths and weaknesses. And thanks to your curriculum’s emphasis on
emotional intelligence and the power of vulnerability, the individualized guidance
that coaches offer becomes all the more critical.

As you build your program curriculum, the question you should ask yourself is
not if you should include coaching elements, but what form they should take, how
participants and coaches should interact, and who you will call upon to ensure your
participants are getting the most out of their coaching.

But filling in those blanks can get tricky without a clear vision. What balance
of accredited coaching and on-the-spot mentorship and guidance should you
strike? How do you ensure that diverse participants have access to coaching
that is relevant to their experiences and context? How much freedom should
participants have to design their own coaching agenda? Chances are, you have
options at your disposal that you have not even considered.

19
Data indicates that coaching’s
individualized approach works:
Strategies to Encourage Coaching Coaching in Practice

91% of Schusterman Fellowship

When putting together your coaching game plan, From day one, each Schusterman Fellow is paired with a master- “It’s amazing. Coaching
alumni reported that the certified executive coach. Across 18 individual sessions, the Fellows
program’s coaching component
consider the following tactics: for professionals and
come to rely on their respective coaches as a profound source of
contributed to their growth as support and constructive challenge. But the learning doesn’t stop leaders is a must. It
leaders. One participant said, FORGE KEY PARTNERSHIPS. Believe it or not, there are ways there. Instead of relying exclusively on professional coaching, the
“It’s amazing. Coaching for to provide individualized leadership coaching without taking Schusterman Fellowship promotes a strong culture of peer coaching,
helped me manage my
professionals and leaders is a your program budget sky-high. There are plenty of accredited as well—providing Fellows with opportunities to share their strengths, team better and manage
must. It helped me manage my while also honing their own skills as coaches. Senior Fellows also
coaching programs willing to work pro bono to give their
team better and manage my have ample opportunities to serve as coaches and mentors to the
my transition to a new job.”
students valuable experience in their field. By joining forces
transition to a new job.” cohorts that follow.
with one, you can offer quality coaching while maximizing
your program resources.
Schusterman Fellows build coaching skills throughout the
program. Each workshop includes elements of “deep listening” and
One Rockwood alum said START A COACHING PIPELINE. How can you ensure that “courageous conversations,” and every Fellowship gathering sets aside
of the program’s coaching
your participants always have skilled, enthusiastic coaches time to discuss “leadership dilemmas.” In these sessions, Fellows
elements, “The tools and actively coach their peers through specific leadership challenges, an
to guide their leadership development? By cultivating
support systems were exercise that many Fellows say they internalize and apply to their
strong coaches yourself. Build trainings designed to hone
invaluable in my own own teams and organizations at the conclusion of the program.
transition and serve me coaching skills directly within your program—then call upon
every day in helping others.” participants and alumni who can effectively apply coaching
Schusterman Fellows also work with Robert Kegan and Lisa Lahey’s
practices. “Immunity to Change” map, which shows how our individual beliefs—
along with the collective mindsets in our organizations—combine to
EMPOWER YOUR STAFF. You probably have some highly create a powerful immunity to change.7 Fellows workshop their maps

capable coaches in your midst—people with whom your with their colleagues and often with their executive coaches.

participants are already comfortable sharing their strengths

Coaching serves as the basis of Rockwood programs, and is
and struggles. Take a closer look at your program faculty to
integrated at every level and within every stage of the learning
identify those who can serve as both skilled facilitators and
process. Even the interview required to get into their programs
effective leadership coaches. is its own coaching session! Rockwood also employs a combination
of peer and professional coaching. This format allows participants
HARNESS YOUR NETWORK. Not only do you have program to maintain their momentum in between exercises and trainings,

faculty and distinguished alumni to lean on—not to mention helps establish and strengthen learning habit and offers a stable,
consistent support system for Fellows throughout their program
accredited coaches, should you decide to include them—you
and beyond.
also have a network of professional connections, many of
whom may be interested in donating their time to support
Rockwood’s professional coaches are either the fellowship’s trainers
the next generation of leaders. Consider establishing a or affiliate coaches knowledgeable about the fellows’ movement
mentorship program that can serve as an added layer of or sector. Every Fellow receives one coaching session after every
personal and professional support for participants. general program session, as well as unstructured peer coaching with
a fellow cohort member intended to expand upon the curriculum
elements they are learning.
INCENTIVIZE FURTHER LEARNING. Some of your participants
might require specialized assistance, have a particular coach
in mind or want to take their skills to the next level—but
lack the funds to pursue additional coaching. Encourage
further learning by offering stipends for participants looking
to hire their own coach or take their learning to the next level
beyond what your program can offer.
20 21
Encourage Sector
and Cross-Sector
Collaboration
Extend your program’s impact by emphasizing
the benefits of constructive collaboration.

Let’s take a quick trip into the future. Your leadership development
program was launched successfully and has been running strong for
20 years. Consider the path you and your team took to get where you
are. How did you measure your program’s influence? What positive
change did your participants go on to accomplish? What are some
news headlines that demonstrate your participants’—and thus, your
program’s—impact on your sector and the world around you?

Now, step back into the present. You have likely spent most of
your time so far carefully considering the content of your program
on the participant level. But helping your participants achieve concrete
change, and thus, achieving your larger organizational goals, means re-
examining that content through a wider lens, beyond your participants,
your program or your field.

And that means acknowledging one fundamental truth: Strong

leaders understand the importance of bringing diverse voices to the
table.8 If your objective is to empower people to make a difference,
you’ll have to show them that they cannot always do it alone.

By providing the tools for constructive collaboration, you will set

your program (and your sector) on a trajectory for positive growth.

23
Data shows us that good things
happen when movements align
Strategies to Encourage Collaboration Collaboration in Practice

under shared goals. Thanks Extend your program’s impact by emphasizing the benefits The Schusterman Fellowship employs a “Favor Economy” approach, “What is now possible
to Rockwood’s emphasis on in which Fellows are encouraged to make formalized “requests”
of constructive collaboration. is that I have new
cross-sector collaboration, and “offers” of each other to solidify their network of support,
86% of participants felt CONFRONT CHALLENGES. If your program’s ultimate objective is to ensure that everyone is benefitting from their peers’ strengths strategies for engaging
better equipped to sustain and gain experience passing along their individual skills to others.
transform your sector for the better, fomenting change means tackling
their energy over a lifetime of The program even offers collaboration grants to Senior Fellows to
with allies, partners and
complex issues head-on. Embolden your participants to face challenges
service. An alum of Rockwood’s
through candid discussions that pinpoint these problems, the factors
incentivize them to work together to address key challenges and colleagues when working
Fellowship for Gender and opportunities facing the Jewish community.
Racial Justice Leaders in that contribute to them and key opportunities to address them. In fact, on really tough issues of
the Fellowship can serve as a laboratory for dealing with difficult inter-
the HIV/AIDS Movement Rockwood programs and the Schusterman Fellowship both intersectionality and
said, “What is now possible is group challenges. emphasize the importance of engaging in collaborative dialogue,
that I have new strategies for providing participants with opportunities to dive into topics of
inequality with our
engaging with allies, partners SHARE SUCCESS STORIES. Participants should have access to relevant their own choosing in small groups. In fact, the Schusterman movements.”
and colleagues when working Fellowship calls on Rockwood staff to lead a session on “courageous
case studies that illuminate the advantages of collaboration. Luckily,
on really tough issues of conversations” to provide Fellows with practical experience
you already have a robust network of alumni using their enhanced
intersectionality and in addressing complex issues head-on and reaching out to
inequality with our
leadership to make a difference. Canvass them for real-world examples
colleagues across sectors to workshop solutions.
movements.” of leaders coming together, and share these stories with your current
cohort to demonstrate the power of cooperation. Rockwood‘s program emphasizes “collaborative conversations,”
where Fellows choose topics to discuss during sessions. Trainers
BROADEN YOUR REACH. Nothing beats a hands-on approach are prepared to shift the design of a session to fit in Fellows’
67% of Senior Schusterman requested conversations. The conversations are completely
for demonstrating the importance of cross-sector collaboration.
Fellows have collaborated in guided by the Fellows and often lead to collaborative projects,
Join forces with other leadership development programs—within or
a meaningful way with other partnerships or follow-up gatherings,
Fellows and 75% indicate that
outside your field—to provide practical experience, help participants
the Fellowship has contributed find common ground with unexpected allies and spark opportunities
During the last few months of the Schusterman Fellowship, Fellows
to some form of collaboration for future collaboration. are encouraged to work collaboratively on “capstone” projects.
between their organization Fellows directly apply what they are learning to either make a
and the organizations of other MAKE COLLABORATION EASY. Building bridges across sectors positive impact on their organizations or to ask and explore big
Fellows.
should be a core tenet of your program, and emerging leaders questions addressing a complex issue in the Jewish community.

with big ideas should have access to tools to take this concept These projects are intended to sow the mindset of collaboration
and give the Fellows space to practice working together to
to the next level. Encourage participants to consider ways to
strengthen the community.
incorporate cross-sector collaboration into their own work, and
offer micro grants that enable them to make their plans a reality.
Even if you do not have the budget or resources to create incentive
programs, the simple act of getting leaders in a room together and
giving them a platform to communicate can result in meaningful,
collaborative projects!

KEEP IT CLOSE TO HOME. While some elements of leadership

development are constant, your sector and the social landscape that
surrounds it are likely changing rapidly. Your program should reflect
the community your participants aim to serve. To ensure maximum
relevance, regularly engage key stakeholders, including thought leaders
and community members, in the design of your program’s approach.
This will not only keep your curriculum fresh, but will also equip your
participants to use what they have learned to generate real change on
the ground.
24 25
 BE INTENTIONAL ABOUT RELATIONSHIP BUILDING.
Help sow the seeds of a solid, long-lasting participant network by providing consistent
opportunities for peer-to-peer engagement, both in-person and with the assistance of
digital communication tools.
A Checklist: Building a Successful
Leadership Development Program ✓ CONNECT VIRTUALLY by regularly bringing participants together via online tools
like Zoom and Slack.

Ready to get to work? As you begin to piece together your leadership ✓ ENCOURAGE LOCAL LEARNING by fostering regional gatherings for those who live
in close proximity.
program, remember your key objectives:
✓ PRIORITIZE ALUMNI by continuing to engage past participants long after the core
program ends.
SET THE STAGE FOR VULNERABILITY
Lay the groundwork for participants to forge strong bonds. Devote organizational ✓ PROMOTE CROSS-COHORT SHARING by encouraging interaction between past and
resources to creating an environment where it is okay to admit failures, express present peer groups.

fears, ask questions and engage in constructive debate.

DESIGN THE RIGHT COACHING EXPERIENCE.
✓ START EARLY by getting everyone together in a room at the beginning
Provide participants with regular individualized learning through partnerships with trained
of your program.
coaches, helping them maximize their leadership potential, build up their unique strengths
✓ BE ROLE MODELS by having faculty join group activities and help and address areas for growth.
participants let their guards down.
✓ FORGE KEY PARTNERSHIPS by joining forces with coaching program students willing
✓ SET THE TONE by establishing a common set of guidelines to encourage
to work pro bono.
respectful dialogue.
✓ START A COACHING PIPELINE by helping participants hone their coaching skills and
✓ BREAK THE ICE by leading a series of “get to know you” activities designed
put them to work.
to foster deeper connections.
✓ EMPOWER YOUR STAFF by identifying those who can effectively apply leadership
✓ PRIORITIZE DIVERSITY by ensuring that participant groups vary in
coaching practices.
demographics, interests and experiences.
✓ HARNESS YOUR NETWORK by tapping your own professional connections to serve
✓ ENCOURAGE SKILL SHARING by giving participants the space to open
as mentors.
up about strengths and areas for growth.
✓ INCENTIVIZE FURTHER LEARNING by offering stipends for those looking to pursue
next-level coaching.
FOCUS ON EMOTIONAL INTELLIGENCE
Encourage your participants to harness and express their emotions in
constructive ways—getting in tune with the mental, emotional, spiritual ENCOURAGE SECTOR AND CROSS-SECTOR COLLABORATION.
and physical sides of their personal leadership style. Set up your participants to achieve concrete change by helping them understand the
importance of working together and bringing diverse voices to the table—both within
✓ HELP THEM LOOK INWARD by firmly establishing the importance and outside of your sector.
of “soft skills” from the beginning.
✓ CONFRONT CHALLENGES by emboldening your participants to candidly discuss complex
✓ KEEP THINGS PRACTICAL by providing concrete, real-world strategies
issues facing your sector.
to put concepts to work, at work.
✓ SHARE SUCCESS STORIES by canvassing alumni for real-world examples of constructive,
✓ SHOW, DON’T TELL by having coaches and faculty demonstrate emotional
successful collaboration.
intelligence during sessions.
✓ BROADEN YOUR REACH by joining forces with other leadership programs to encourage
✓ DIVERSIFY THEIR LEARNING by employing a variety of activities that cater
cross-sector teamwork.
to different learning styles.
✓ MAKE IT EASY by helping participants collaborate with others in the program on projects.
✓ KEEP IT CLOSE TO HOME by engaging community leaders and other stakeholders when
building your curriculum.
27
REFERENCES Recommended Resources:
1
Learning for Action. (2017, April). The Schusterman Family Philanthropies: Diversity, Equity and Inclusion
Schusterman Fellowship Evaluation. Retrieved from https://www.schusterman.
org/jewish-community-and-israel/signature-initiatives/schusterman-fellowship/
schusterman-fellowship-evaluations
Jagpal, N., & Schlegel, R. (2015, March 23). Cultivating Nonprofit
2
Learning for Action. (2016, December). Rockwood Leadership Institute’s Leadership: A (Missed?) Philanthropic Opportunity. Retrieved from
Cohort-Based Programs: 2016 Third Party Evaluation. Retrieved from
https://www.ncrp.org/publication/cultivating-nonprofit-leadership-
https://rockwoodleadership.org/2016-evaluation/
missed-philanthropic-opportunity
3
Rund, J. (2016, September 16). Why Young Bankers, Lawyers, and Consultants
Need Emotional Intelligence. Harvard Business Review. Retrieved from https:// Kunreuther, Frances and Sean Thomas-Breitfeld (2017). Race to
hbr.org/2016/09/why-young-bankers-lawyers-and-consultants-need-emotional-
Lead: Confronting the Nonprofit Racial Leadership Gap. Retrieved
intelligence
from http://racetolead.org/race-to-lead/
4
Caillet, A., Hirschberg, J., & Petti, S. (2014, December 8). How Your State of Mind
Affects Your Performance. Harvard Business Review. Retrieved from https://hbr. Meehan, D. (2018, August 01). What Would it Look Like to Bring
org/2014/12/how-your-state-of-mind-affects-your-performance
a Racial Equity Lens to Leadership Development? Retrieved from
5
Design Thinking: A Method For Creative Problem Solving (2018) Retrieved from http://leadershiplearning.org/blog/deborah-meehan/2018-08-01/what-
https://www.ideou.com/pages/design-thinking
would-it-look-bring-racial-equity-lens-leadership-development?
6
MacKie, D. (2014). The Effectiveness of Strength-Based Executive Coaching in
Enhancing Full Range Leadership Development: A Controlled Study. Consulting Phillips, K. W. (2015, April 10). How Diversity Makes Us Smarter.
Psychology Journal: Practice and Research, Vol 66(2), 118-137. Retrieved from http://www.creativitypost.com/activism/how_diversity_
7
Kegan, R., & Lahey, L. L. (2009, January 13). Immunity to Change: How to makes_us_smarter
Overcome It and Unlock the Potential in Yourself and Your Organization. Boston,
Mass: Harvard Business School Press. Thomas-Breitfeld, S. (2017, April 10). How to Think Differently about
8
Becker, J., & Smith, D.B. (2018). The Need for Cross-Sector Collaboration. Diversity in Nonprofit Leadership: Get Comfortable with Discomfort.
Stanford Social Innovation Review, 16(1). Retrieved from https://ssir.org/articles/ Retrieved from https://nonprofitquarterly.org/2017/04/10/think-
entry/the_need_for_cross_sector_collaboration differently-diversity-nonprofit-leadership-get-comfortable-discomfort/

29
For more information, please contact:

ABBY SALOMA
Director, Leadership and Talent
Charles and Lynn Schusterman Family Philanthropies
202-216-2760
asaloma@schusterman.org

SHARON PRICE
Director of Strategic Initiatives
Rockwood Leadership Institute
510-251-2500 ext. 106
partnerships@rockwoodleadership.org