A reusable kit for proposals, retreats & workshops.
Twenty-four slide layouts, designed against four real WBT decks. Mix & match — every layout in this deck is a working template you can duplicate, fill, and ship.
1:1 Coaching
Through a Career Transition
Prepared for Planned Parenthood Federation of America
Dear {Client Name},
I am honored that you reached out, and so excited about the possibility of working together. What follows is a proposal for a structured journey specifically designed for senior leaders like you — folks who have led significant work and are now ready to step back, breathe, and think expansively about what comes next.
We can begin as soon as you are ready with an initial cycle of six sessions. Following that, you are welcome to continue with additional one-off sessions or a full engagement. I am here to support you through whatever timeline and depth feels right.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
1:1 Coaching
through a career transition.
A structured journey for senior leaders ready to step back, breathe, and think expansively about what comes next.
What is this coaching engagement?
Built for leaders in high-stakes, mission-driven roles who are ready to pause, reflect, and dream before deciding what's next. We believe you are deeply knowledgeable about your own growth — our process draws out that wisdom through inquiry, curiosity, and compassionate challenge.
What to expect
- Partnership. A confidential, trusting, professional 1:1 coaching relationship.
- Personalized goal-setting. A collaborative process where you set the focus and goals.
- Safe space to practice. Real situations, real relationships, real stakes.
- EQ development. Growth in emotional intelligence, self-awareness, and leadership skills.
Structure
- Each session is 60 minutes. Walking sessions are encouraged as an option.
- Goals are set at the outset, revisited along the way, and assessed at the close of each cycle.
- Clients typically engage in 6–12 sessions over four months.
- Between sessions, brief check-ins are available via email or text.
Two distinct levels of senior leadership.
Each tier has its own depth of experience and its own texture of what 'what's next' means. Both share a hunger for expansive thinking before decisive action.
Director Level
- Ready to step back (or currently stepping back) from execution
- Questioning whether the current path still fits
- Seeking permission to want something different
- Navigating identity beyond the job, role, or title
C-Suite Level
- Wrestling with legacy and long-term impact
- Feeling the weight of "who am I without this title?"
- Ready to lead differently, lead somewhere new, or step out of work
- Craving space to think beyond the organization
Coaching through a career transition.
Each session builds on the last. Reflection deepens, the aperture widens, and clarity comes into focus.
Who have you been, and how did you get here?
Tell your full career story — not just the résumé version. Pivotal choices, paths not taken, identity built to date.
Where have you honored or buried your values?
Move past optimizing for what looks right from the outside. Talk intrinsic drive, motivation, energy.
What does the wide-open version look like?
Expansive, generative session. Imagine multiple possible futures. Widen the aperture on what 'next' could mean.
What's enduring, and what are you ready to let go of?
Examine what's non-negotiable versus familiar. Surface limiting beliefs disguised as constraints.
What's true, what am I here to do, and for whom?
Synthesize values, energy patterns, future visions, and constraints into a coherent purpose.
What am I carrying forward, and what are my next steps?
Both completion and momentum. Honor the work, translate insight into intention, name next steps.
A flexible structure, built around your rhythm.
I am available to begin this engagement as soon as you are ready. The arc below is the spine — it's also responsive: if a real-world conversation or decision emerges that warrants a shift in our attention, we'll talk about it and adjust together.
- Six 60-minute sessions as an initial cycle, scheduled bi-weekly or weekly as schedules allow.
- At the close of the initial cycle, you may continue with an additional cycle or one-off sessions.
- Between sessions, I am available for check-ins or support via email or text message as needed.
- If an interview or conversation emerges that warrants a shift away from the arc as described, we'll talk about the shift and decide how to proceed in whatever way best supports your work.
A custom experience, shaped with you.
We work alongside our clients to design a powerful plan for your time together — before, during, and after the room.
Discovery & Planning
- Understand strategic priorities, current team climate, and clarify retreat objectives.
- Conduct pre-retreat consultations with key stakeholders to surface context and opportunities.
- Develop a comprehensive agenda aligned with your objectives, incorporating your feedback.
- Propose pre-retreat activities to prime the team.
Facilitation
- Hold an emotional and intellectual container for participation, collaboration, and clear communication.
- Facilitate interactive sessions that encourage active participation across the group.
- Guide discussions, navigate complexity, and ensure all participants have meaningful opportunities to contribute.
Follow-up
- Create and distribute a retreat evaluation to gather participant feedback and insights.
- Analyze evaluation data and synthesize key themes to share back with you.
- Facilitate a post-retreat debrief to share findings, recommend next steps, and close our work together.
Six pressure points that will be in the room whether named or not.
Change imposed from above
The reorganization felt done to the team, not with the team. No input. No co-design. Departures happening in silence breed anxiety.
Not one team yet
Almost no one identifies with the team. People don't know each other's names, roles, or daily realities. Remote staff feel invisible.
Talking points without meaning
Nearly half can't say what the vision means for their day-to-day. Heard it. Can't live it. Some feel attempts to live it have been sidelined.
Unprocessed pain is present
The interim VP situation, a key departure, favoritism, and perceived promotion inequity sit in the room, named or not.
Invisible labor, stalled growth
Directors carrying outsized workloads without title changes or recognition while watching others advance.
Territorial across EA
Cross-EA work feels like 'hunger games.' R&P is routed around, not sought out. Ownership disputes block progress.
A retreat designed in response.
“To answer, together for the first time, what our cumulative value is as research and data experts, federal and state policy experts and strategists, and sex education experts — and to build the identity and ways of working that let us deliver on it.”
— Maya Carrington, Executive Director, Center for Reproductive Equity
Each names a step toward the purpose.
Close the gap between talking points and day-to-day meaning through concrete conversation and interaction.
Commit to norms the team can hold each other to — not a document that lives in a drawer.
Collective identity has to be discovered in the room. Build it together, not handed down from above.
Name and experiment with collaboration at two levels: within R&P, and across External Affairs broadly.
Name the hard stuff, without defensiveness.
Principles that shape every session.
Priya Parker's disputable purpose
Every design decision is tested against the retreat purpose. If a session doesn't serve it, it doesn't belong.
Gestalt / Cape Cod Method
Awareness before action. Solo → pairs → small groups → full group. Day 1's relational ground makes Day 2 possible.
The Name Wall
A shared physical space that accumulates across both days for observations, needs, offers, and 'I See You' statements.
Two rounds of vision articulations
The leader shares once when the team is relationally warm, once when ready to do something with it. The second responds to what was heard.
Collaboration ideas chart
Open from Day 1, created by the team in real time, brought to life on Day 2 in an open fishbowl. Ideas belong to the team.
Pairings driven by data
Each person identifies who they know least. We share back so people can prioritize the low-familiarity connections for walks and small groups.
A purposeful sequence — not a packed agenda.
Arrival, Awareness & Who We Are
Day 1 is relational and awareness-building. Before the team can do substantive work together, they need to know each other — not just by role, but by what they carry, what they need, and how they're wired.
- Name what's true about the moment this team is in.
- Test the retreat purpose against their own experience.
- Begin to see each other's actual work and actual needs.
- Hear the leader's vision and respond to it honestly.
Substance, Vision & What We Build
On Day 2, the team moves from knowing each other to building something concrete together — identity, agreements, and real collaboration ideas. This is possible because of the relational work built in Day 1.
- Map what each workstream does and what it needs from the others.
- Discover what only this team can do at the intersection.
- Return to and wrestle with the retreat purpose statement.
- Commit to real norms, routines & rituals — and live collaboration ideas.
Arrival, awareness & who we are.
-
09:30Threshold openingTwo-word check-in: how you're arriving, how you hope to leave. Sets the tone. Introduce the Name Wall + Collaboration Ideas Chart.30 min
-
10:00Stephanie opensAcknowledges what the team has been through (without defending), then introduces the retreat purpose statement as the reason they're here.20 min
-
10:20Purpose walk-and-talkCross-workstream pairs walk with two questions: honest reaction to the purpose; what would need to be true for it to feel real in six months.40 min
-
11:00Purpose conversation (full group)Open conversation about what surfaced from the walk-and-talks.35 min
-
11:35Break15 min
-
11:50The work I do, and want you to seeIndividual writing, then small-group shares. Each group adds observations to others' Name Wall spots — first contributions to the wall.40 min
-
12:30Lunch60 min
What the team carries back to work.
An answered purpose
A shared understanding of this team's cumulative value — what research, policy, and education can do together that none could do alone.
Named identity
A team that has begun to discover who it is — not just who its members were before they got here.
2–3 real working agreements
Specific norms, routines, and rituals organized by WBT's resilience framework. Typed and distributed within 48 hours.
Live collaboration ideas
2–3 cross-workstream collaboration ideas with named owners and first steps — developed in the open fishbowl on Day 2.
The Name Wall
A physical artifact of being seen — observations, needs, offers, and 'I See You' statements that accumulated across both days.
A new starting point
The leader's vision — heard twice, wrestled with, and connected to what the team itself identified as possible.
Investment & payment terms.
The structure below accounts for our time across two days of in-person facilitation, plus project management, planning, and follow-up.
Payment terms
- Invoiced 50% at start, balance after the engagement.
- Net 30 from invoice date.
Optional services (price upon request)
- 360-degree feedback facilitation.
- Leadership self-assessment and debrief.
Selected engagements & case studies.
Engagements most directly relevant to your focus areas — leadership communication, supervisory practice, cross-team collaboration, and values-aligned leadership in mission-driven organizations.
Two partners. One brain trust.
WBT is a collaboration between Jenna Shapiro and Stacy Berger. We've worked as leaders in presidential campaigns, across all levels of school systems, at the senior leadership level of action-driven organizations including Planned Parenthood Federation of America, and alongside individuals and teams from the New York City Department of Education to Fair Fight in Georgia.
We are passionate about doing work we love alongside people we respect. We partner with movement, government, and non-profit leaders — including at the DNC, Empower, and Emily's List — because we understand their unique challenges. Like them, we believe in the possibility of redesigning our social systems to interrupt inequity and build toward a more just future.
Meet Stacy.
Stacy Berger
She/her · ICF Professional Certified Coach · Partner
Stacy is a seasoned leadership consultant with over two decades of experience in advocacy, campaign strategy, and organizational development. A former community organizer who cut her teeth as a Field Organizer on the Kerry campaign, she has led national and grassroots efforts across the nonprofit and political sectors.
She served as Deputy National Training Director and GOTV Director at Obama for America, then spent eight years at PPFA directing coaching, facilitation, and employee engagement initiatives. Stacy specializes in leadership development, strategic planning, facilitation, and partner engagement, with a focus on supporting nonprofit and campaign leaders.
Meet Jenna.
Jenna Shapiro
She/her · ICF Professional Certified Coach · Founder + Partner
Jenna is an ICF Professional Certified Coach with more than two decades of experience across education, nonprofit, and public-sector systems. She began her career as a New York City Teaching Fellow and later served as a Fellow Advisor, mentoring incoming teachers.
She joined the founding team of KIPP AMP Academy as Dean of Teaching and Learning, then served as a School Director at Teach For America's NYC Institute and an Education Pioneers Fellow at DREAM Charter School. Jenna specializes in adult learning, team facilitation, and organizational change, helping leaders build teams rooted in trust, accountability, and humanity.
Organizations we've worked with.
Not sure what you need? Take our Leadership Reflection Survey to determine if coaching with us is the right next step, or book a chemistry call. We'll help you reflect on readiness, goals and alignment, and then put together a package tailored to your specific needs.
Coaching equips leaders and teams to navigate complexity with impact and resilience.
of people who receive coaching report increased self-confidence.
of leaders improve performance, communication, and relationships.
of companies and organizations report a positive ROI on coaching.
Three pathways to grow, connect, and lead.
Leadership Coaching
Coaching focuses on one individual leader's growth, supporting reflection, skill-building, and more intentional leadership.
Learn More
Team Coaching
Team coaching is an ongoing partnership that treats the team as the unit of change, strengthening how people work together over time.
Learn More
Facilitation + Training
Training and facilitation supports team development through key conversations, helping them think clearly, surface what matters, and make decisions.
Learn More