“CREW Leadership Academy allowed me to re-assess my priorities at professional level, enhanced my negotiations skill, and led me in intentional path that set in motion a promotion. Above all, to know my professional value.”
Carla Cabral, Senior Compliance & Portfolio Manager
Massachusetts Housing Partnership
Click here to apply to the 2025-2026 CREW Boston Leadership Academy. The deadline to apply is Monday, June 16, 2025.
"Participating in the CREW Boston Leadership Academy was truly a transformative experience for me. Through thoughtful discussions, practical workshops, and the support of an inspiring cohort, I developed the confidence to step into leadership opportunities and advocate for ideas I believe in.
One of the most impactful aspects was the camaraderie within our group. Being surrounded by a diverse, driven group of women who were all working through similar challenges and aspirations created a strong sense of support and accountability. We lifted each other up, celebrated wins—big and small—and built relationships that I know will last well beyond the program.
CREW Boston didn’t just help me grow professionally; it reignited my motivation and drive to lead with purpose and authenticity."
Lindsie Tosca, Managing Director - Accounting
Jones Street Investment Partners
2025-2026 Leadership Academy Program Overview
Friday, October 17, 2025 - Leadership Vision and Assessment
8:30 a.m. - 1:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
This session introduces the cohort, the program and the program facilitator. Expectations and group guidelines will be agreed upon. Participants will conduct a leadership self-assessment and set goals. Using the assessment, participants define their leadership vision, specifically incorporating their values, hopes and career ambitions in the context of the organization.
- Reflect on self within context of organization
- Develop ability to think big picture about leadership
- Reflect on one’s inherent values and beliefs and connection with underlying actions
Friday, November 14, 2025 - Understanding Your Bias
8:30 a.m. - 12:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
Unconscious biases women have about themselves are an invisible threat to women’s careers. In the current situation, these unconscious biases are more visible than before and manifest as women take on more of the “home” work. This module focuses on helping women recognize and overcome these limiting assumptions through case studies to improve decision-making and risk-taking. Inter-sectional aspects of bias will be introduced. Within this context, the systemic biases will be discussed and participants will learn how to manage and overcome these barriers. Within this context, the systemic biases that exist in the Real Estate industry will be discussed and participants will learn how to manage and overcome these barriers.
Learning Objectives
- Identify how flawed assumptions might get in the way of our own career story
- Practice re-framing for improved decision making and risk-taking
- Redefine our career narrative
Friday, December 5, 2025 - Developing New Business
8:30 a.m. - 12:30 p.m.
Facilitator: Haley Ayraud Haggerty, Next Level Training, Inc.
In this module, participants learn to develop a pipeline of opportunities. Whether participants are in an active business development role or not, selling is an important part of business, both externally to potential clients and internally with your organization. Learn practical tools that will enhance current business development activities through strengthened attitudes, new/improved behaviors and tech- niques. Each person will walk away with a tool kit and the start of a business development playbook. The group will be split into those that experience where they will focus on owning their sales process. The second group with less experience will focus on owning their networking behavior.
Learning Objectives
- Develop practical tools that will enhance current business development activities through strengthened attitudes, new/improved behaviors and techniques.
Friday, January 9, 2026 - Managing the Team
8:30 a.m. - 12:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
This module introduces what makes a successful manager, opportunities for management within Real Estate, the importance of delegating and engaging within the team environment, and how to create an environment to cultivate collaboration and innovation.
Learning Objective
- Define effective team concepts
- Explore team styles and their impact on team effectiveness
- Explore and apply tools to improve team performance
Thursday, January 22, 2026 - Mid-Program Check-in Zoom
12:00 p.m. - 1:00 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
Mid-program check-in with all participants and facilitator.
Learning Objectives
- Check in on program learning goals
- Give advice and feedback on challenges related to the goals
Friday, February 6, 2026 - Promoting Your Value
8:30 a.m. - 12:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
In this module, participants will think strategically about their value and strategically assess how to leverage the “silver lining” in the current situation. Participants will learn how to frame theiraccomplishments in ways that showcase the value they bring to the organization and build their skills in thinking more strategically. Participants uncover and overcome resistance to self- promotion. They learn how to increase visibility and how to build meaningful networking, mentoring, andsponsorship relationships to accelerate their career – and to model this behavior for their women colleagues.
Learning Objectives
- Identify ways to promote one’s value-add authentically
- Quantify their business value to their employer and themselves
- Understand the relationship between self-promotion and value-based impact
Friday, March 6, 2026 - Promoting Your Value
8:30 a.m. - 12:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
This workshop equips participants with the mindset and tools to shift from reactive problem-solving to proactive, strategic leadership. Effective leaders don’t just respond to challenges—they think ahead, expand their influence, and take smart, calculated risks. Participants will learn to think and plan strategically, view their careers through a broader lens, and develop a forward-looking plan to measure their progress while confronting common barriers such as risk aversion and reluctance to seek support. By focusing on long-term leadership impact rather than day-to-day execution, participants will leave better prepared to anticipate future challenges and make high-impact decisions that drive organizational success.
Learning Objectives
- Shift Perspective to Enhance Leadership Impact
- Expand Influence Through Strategic Networks
- Take Strategic Risks for Growth
- Create a Personal Strategy for Leadership Growth
12:00 p.m. - 1:00 p.m.
Pre-Close Progress Check-in with all participants. Participants will check-in in small groups and discuss their goal and skill progress. There will be an admin facilitator only.
Learning Objectives
- Check in on program learning goals
- Give advice and feedback on challenges related to the goals
Friday, April 10, 2026 - From Insight to Impact: Integrating Skills for Strategic Impact
8:30 a.m. - 12:30 p.m.
Facilitator: Katrina Graham, Orange Grove Consulting
The final module pulls together the key learnings across the program to transform the participants fromindividual contributor to strategic business leader. Participants learn how integrate their skills for strategic impact in their careers. Participants also celebrate what they’ve learned and how they’ve developed in the program.
Learning Objectives
- Review, reflect and debrief lessons learned across the program
- Develop way forward plan including how to measure progress
- Commit to behavioral change plan
April 2026 - Graduation held at CREW Boston's Annual Achievement Awards
5:30 p.m. - 9:00 p.m.
May 2026 - Graduation Celebration Dinner
5:30 p.m. - Location TBD
“The CREW Leadership Academy has helped me gain more self-confidence as a professional working woman. The interpersonal skills I learned from the program are practical. I have grown to be a better leader to myself as well as others.”
Nicole Ng, Director
PKF O'Connor Davies LLP
Location
All classes will be held in Boston MA
(In case a session is cancelled due to snow, the make up session(s) will be take place on one of the following dates, to be determined at a later time)
Eligibility
Applicants should be professionals working in the commercial real estate industry who have demonstrated leadership within their organization, including managing small teams.
Applicants should have 10-15 years of experience in commercial real estate, however, more or less experience will be considered if otherwise qualified.
Applicants should be available for all sessions, as 100% attendance is required for the program.
Applicants must have the desire to gain insights, and leadership skills, and also have a strong aspiration to positions of greater influence within their organization.
Cost for the 2025-2026 Program
Member fee: $2,900
Non-member fee: $3,685 (includes application and membership to CREW Boston)
Deadline
Application deadline: Monday, June 16, 2025
Space is limited. Curriculum subject to change in an effort to provide the most value to participants. Click
here for a pdf outline of the program. If you have any questions about this program, please contact
laura@crewboston.org
“The CREW Leadership Academy provided me with a unique opportunity to explore and organize my ideas, including biases and self-doubt, about personal leadership and professional growth. The facilitator immediately created an atmosphere where everyone could be vulnerable, feel supported and get comfortable being challenged. The program content was informative and engaging each session. The bonus factor really came from exchanging personal stories with such a diverse and talented group of CREW women.
As a result, I have an actionable leadership vision and a fabulous new group of inspiring friends. My advice to others: don’t wait until you feel fully prepared—apply when curiosity strikes!”
Amy Apfelbaum, Principal
McPhail Associates, LLC