Leadership Academy

About the Leadership Academy

The CCIAOR Leadership Academy is a dynamic multi-session program held at diverse locations throughout the region and focused on improving leadership skills and community knowledge with the goal of empowering you to be a better leader at work and in your community.

The sessions cover topics related to skills enhancement, community building, diversity and awareness of today’s significant topics in our industry which will provide you with a foundation to build and execute your own leadership style.

Throughout this program, you will have the opportunity to interact and have thought-provoking discussions with colleagues and community leaders at various stages of their careers who bring their own experience and perspective to each session.

The CCIAOR Leadership Academy is proudly supported and sponsored by Guild Mortgage.

The 2023 Leadership Academy

2023 Leadership Academy Sessions - click on the session name to see details

The Art of Leadership & Alumni Meet & Greet Reception
Thursday, March 9 | 3:00pm - 6:00pm

The first session starts with a casual welcome and introduction to your new classmates and Leadership Academy alumni. At this session you will learn how a local community helped rescue an architectural treasure that is now the Cultural Center. Get inspired to participate in a fun art project with your fellow Leadership Academy classmates as ‘artists in residence’ and get to know each other better in the process.

Leadership Academy alumni and CCIAOR Leadership will join directly afterward for a Meet & Greet Reception.

Location: Cultural Center of Cape Cod, 307 Old Main Street, South Yarmouth

Discovering Your Leadership Presence
Tuesday, March 21 | 10:00am - 12:30pm

Research shows that the #1 most critical factor for leadership effectiveness is the leader’s capacity for self-awareness, which is at the core of finding your leadership presence.

Presence, which is different from charisma, has to do with presenting yourself in a way that generates trust, interest, and engagement of others using your unique authenticity. You can have a profound impact on others when using your leadership presence in a thoughtful and honest manner.

Exploring and understanding your belief system opens you up to appreciating and embracing your presence and how you want to show up as a leader. During this session, you will use a values assessment to deepen your self-awareness, explore ways to build trust, and learn more about how you carry yourself, influence others and act with intention.

Location: Gestalt International Study Center, 1035 Cemetery Road, South Wellfleet

Cape Cod Real Estate Summit
Tuesday, April 4 | 8:30am - 4:30pm

Spend the day at one of the most spectacular locations on the Cape hearing from dynamic local, state and national experts in their field who will educate and inspire you.

At lunch, you will have an opportunity to further network and engage with your fellow classmates along with keynote speaker Paula Monthofer.

Includes optional breakfast, lunch, social reception, and lots of networking opportunities.

Leadership Academy participants attend the Summit at no additional charge as part of the academy. Special overnight accommodation rates will be available if you want to make a ‘workcation’ around the Summit!

Location: Wequassett Resort, 2173 MA-28, Harwich

Making Room at the Table
Tuesday, April 25 | 10:00am - 12:30pm

In honor of Fair Housing Month, this Session will focus on the three fundamentals of Diversity, Equity & Inclusion (DEI) that leaders need to understand to successfully invoke change in the real estate industry: bias, privilege and fair housing. This informative, thought-provoking session will feature current chairs of CCIAOR’s Diversity & Inclusion Committee for an in-depth discussion where they share their knowledge, insight and experiences. You will end this session with a deeper understanding of the areas where the real estate community can change to be a more inclusive and diverse industry.

Location: Cape Verdean Museum & Cultural Center, 67 Davisville Road, East Falmouth

Navigating Difficult Conversations & Building Consensus
Tuesday, May 9 | 10:00am - 12:30pm

Conflict is going to happen, but it doesn’t have to blow up deals or destroy relationships.

Learn ways on how to prevent or resolve conflict using collaborative and mediation problem solving techniques through more constructive communication. Hands-on exercises, break-out groups and real life scenarios will introduce you to important tools to help you better understand conflict and how to work toward consensus and resolution.

Location: CCIAOR Conference Center, 22 Mid-Tech Drive, West Yarmouth

Understanding Cape Cod's Economy
Tuesday, May 23 | 10:00am - 12:30pm

Real Estate is deeply woven into the fabric of the Cape’s economy. The Cape Cod Commission team will take you on a deep dive into the factors impacting the economy on Cape Cod and how real estate plays a major role in driving the direction of the Cape’s economy. The accessibility of this highly relevant information and data will greatly assist you in doing business with your clients.

Location: Cape Cod Commission, 3225 Main Street, Barnstable

Advocating in Your Back Yard
Tuesday, June 6 | 10:00am - 12:30pm

Hear from Wendy Northcross, former Cape Cod Chamber of Commerce CEO and current Executive Director of the JFK Museum and Ryan Castle, CCIAOR CEO about the Cape’s housing and development history and strategies for sustaining our community by building regional resilience. Bring your questions!

You’ll also participate in an interactive activity to understand how you can create positive change and share your voice at the town level with Amanda Bebrin, REALTOR® and co-founder of The Take Your Seat Initiative.

Location: Family Center for Civic Engagement at the JFK Hyannis Museum, 3225 Main Street, Hyannis

REALTORS® Are Good Neighbors Volunteer Activity
Between June 4 - 11 | Two hour minimum commitment

The group will plan a volunteer activity where you can make a difference as you serve our neighbors and strengthen our community during NAR’s 2023 National REALTOR® Volunteer Days.

Experience Leadership First-Hand
Attend one Association Board of Directors Meeting

Once selected to participate in the 2023 Leadership Academy, you will be expected to attend one board meeting of your choice in order to better understand how the Association operates. This will give you a transparent view of how your Association does business at a local level.

You will have the option of participating in one of the following Board Meetings: May 24, July 26 (dates subject to change). Meetings are held from 10:00am to 1:00pm at the Association Office

Location: CCIAOR Office, 22 Mid Tech Drive, West Yarmouth

Apply to the 2023 Leadership Academy

The Leadership Academy is limited to 16 or fewer participants. Please be sure that you are able to attend all or most of the sessions and will be able to devote the time and resources required to complete the program. Note you must be a CCIAOR member in good standing to apply. Candidates from all experience levels will be considered however, the selection committee generally looks for a minimum of 2 years experience as a REALTOR® and some history of production in the market.

The 2023 Leadership academy program fee for participants is $250. This fee includes admission to the April 4th, 2023 Cape Cod Real Estate Summit at no additional cost (a $175+ value). If you have any questions regarding the program or fee or are unable to cover the cost, please contact Patricia Pry, Events & Partnerships Director at ppyr@cciaor.com.

Apply for the 2023 Leadership Academy

Want to be a part of the 2023 Leadership Academy? Tell us about yourself and why you want to participate using the application below.

The deadline to apply is Monday, February 13th, 2023 at 5 PM.

Apply for the 2023 Leadership Academy!


2021 Leadership Academy graduate Amanda De Oliveira talks about her experience in the Leadership Academy.

From 2022 Graduate Dawn Marie Boynton

"It was such an honor to be part of the leadership academy. The sessions were chock-full of opportunity to become familiar with our professional real estate organization and the Cape community. My eyes were opened to new and interesting non profits and support organizations which I have become part of today. Not only did the academy help me professionally, I grew personally. I was impressed with the camaraderie of the other agents and those who support us at the association. I feel I am a better REALTOR® and person as a result of being in the academy."

From 2022 Graduate Jack Sullivan

"The Leadership Academy exceeded all expectations! I really enjoyed learning more about the Cape community and the unique venues we discovered along the way. As a result, we all came to realize there are some wonderful hidden gems on the Cape. Each session was powerful and offered interesting ideas and resources that really got us thinking and the relationships developed with other members in the class was an added bonus! The Program was very well designed and executed."

From 2020 Graduate Katie Dawson

“It was such an honor to be in the 2020 CCIAOR Leadership Academy, in fact it was a highlight of the year. The programming was inspiring and the relationships that we built have a solid foundation for growth. I especially enjoyed learning more about the association and how hard the leadership works for our REALTORS® as well as the communities they work in. I left the program feeling optimistic which was a challenge this year!”

From 2020 Graduate Tara Franklin

“I got so much out of the Leadership Academy! Even though it was virtual, it was incredibly educational and informative. I learned things about the Cape that I otherwise would never have been exposed to. I also met wonderful colleagues that I look forward to working with in the future. I highly recommend this program to anyone that wants to deepen their experience as REALTORS®.”

Need more information? Contact:

Patricia Pry
Events & Partnerships Director 508-957-4327 email