Leadership Services

Dr. Jolander Headley Pink Blazer with Glasses

Where to Begin

Starting the Journey

It is not always clear cut on whether you need a coach or if you should seek out a mentor, or sometimes you need both.

We are here to support individuals in making the right decision—whether they’re seeking a coach, a mentor, or both. She offers a variety of tailored options designed to meet each person’s unique needs.

Before beginning any journey together, we invite prospective clients to a complimentary 30-minute session. This no-obligation conversation is the perfect first step to connect, explore possibilities, and gain a clearer understanding of your goals—and how we can best assist in achieving them.

Let's Connect to Discuss

Discovery Process

Let's Get Personal

Leaders today understand and acknowledge they and their team would benefit from leadership development training. However, with so many training providers and programs options available in the marketplace, it’s difficult to know who and what will get you the results you need.

One thing that let’s us standout from many in the industry is our Discovery Process, where we get personal with you and your team. This allows us to listen to you, and get to know your goals, and concerns. This allows us to recommend and deliver a customized program that works on your particular situation the unique challenges.

Our Discovery Process consists of deep conversations,  questionnaires, and leadership & behavioral assessments.  These discussions and assessments will help us understand your company’s relationships, strengths, challenges, goals, budget, expectations and other pertinent information.

Dr. Jolander Headley Fiji 2025

Building Effective Teams

Introducing My Process

We provide effective team communication and structure that is important for forging relationships equipping your team with the proper attitudes to develop leaders within.

We will work through goal setting and communication exercises that will bring cohesiveness to your group ultimately increasing productivity due to the positive influences each member will have on the group as a whole.

In addition, we will, at your request, incorporate your organization’s meeting theme, mission / vision statement or build on your existing training schedule to best fit the needs of your group.

Service Delivery Options

We invite you to take a few moments to explore the diverse range of services we offer. Each one is thoughtfully designed to provide exceptional value and tailored solutions to meet your unique needs. Whether you’re looking for expert guidance, innovative strategies, or hands-on support, you’ll find services that can help you achieve your goals.  We’d love for you to discover how we can assist you and your team—let’s start to build something great together!

John Maxwell Introduces Dr. Jolander Headley

Keynote Speaker
Delivering at Your Event
Available for various speaker event options: Keynote, Presenter, and Panelist.
Click here to learn more.
Workshops
Build a Collaborative Culture
Our workshops will help you establish a culture of leadership, improve collaboration & relationships.
Click here to learn more.
Coaching/Mentoring
Personal and Team
As a coach I am here to help you tackle specific tasks and objectives. I work with you to set the objectives to meet your goal.
Click here to learn more.
Destination Retreat
Become Immersed
As the world becomes more global, our exclusive retreats and conferences have a “glocal” (global + local) focus.
Click here to learn more.
Virtual/On Site
Bringing Programs to You
Often large company teams want my services, no one should ever be left out so I will come to you with my programs.
Click here to learn more.
Masterminds
Bringing The Synergy of Energy
Sharpen your business and personal skills with a combination of masterminding, peer brainstorming, education, accountability and support as a group.
Click here to learn more.
Lunch & Learn
Nuggets of Knowledge
A Lunch & Learn event is an opportunity for colleagues from different teams to meet and share their skills and expertise.
Click here to learn more.
Mentoring is the facilitation of the lifelong development process whereby individuals move through various stages of human, emotional, spiritual, educational and intellectual development.
Dr. Martin Sanders
Dr. Jolander Headley Fiji 2025

Keynote and Event
Speaking

Engaging and Exciting

Let us bring our experience and insights to your next event.  We are available in various capacities from keynote to presenter to panelist.

Keynote & Event Speaking

Key Benefits

Jolander Headley is a dynamic keynote speaker, presenter, and retreat host who captivates audiences with her energy, authenticity, and ability to deliver both inspiration and actionable insights. Whether for a corporate event, conference, or retreat, she offers powerful presentations grounded in her transformative H.E.L.P. Program—or tailored to a topic of your choosing to meet your audience’s unique needs. Bring Jolander’s passion and expertise to your next event and leave your attendees energized, empowered, and ready to take action.

Contact Me About Keynote Speaking

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Jolander Headley teaching course

Workshops

Build a Collaborative Team

Our workshops help you establish a culture of leadership, improve collaboration & relationships, get your team and leaders on a path of growth & development, and they never fail to kick-start team momentum!

Workshop Content

Culture Building

Your workshop is uniquely tailored and designed just for you, while addressing your organization’s unique challenges, opportunities for growth, and leadership goals.

Our process and customization ensure your workshop is as impactful as it can be. When applicable, we send materials & assessments in advance, shift content as gaps are uncovered throughout the workshop, and analyze results in a debrief call at the end.

Contact Me About Your Workshop

H.E.L.P. Experience

Available Options

  • Healing for Leaders

  • Equipping with Excellence

  • Leadership Development

  • Plan & Purpose

Dr. Jolander Headley Fiji 2025 - Signed Book

Coaching & Mentoring

For Personal or Teams

As a coach we are here to help you tackle specific tasks and objectives. In role as your coach, we work with you to set the objectives, and determine the number of sessions needed to meet the goal. Our relationship is most often short term, and you may make use of several coaches depending your needs at a given time.

Personal Coaching

Key Benefits

When working with you one-on-one, it is our highest objective to help you reach your purpose, vision and goals by working through programs specific to your needs. Together, we will create a powerful plan for you to gain clarity through a weekly process including, interaction and accountability.

  • What are you doing to invest in yourself?
  • What are you doing to invest in others?
Purchase Personal Coaching

Team Coaching

Key Benefits

When working in a group setting – although it’s not singular in nature – having the entire group’s input in thinking magnifies the richness of the discussions and results in developing solutions that are above and beyond what any individual can create. The cohesive bond that is formed empowers each person to develop the leader within and shine in a safe environment that nurtures the group as a whole. It is an experience unlike any other and follows the same premise as an academic think tank.

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Your feet will never take you where your mind has never been.
Dr. Cindy Trimm
Jolander Headley Retreat Pool Side

Destination Retreats

Immerse Yourself

As the world becomes more global, our exclusive retreats and conferences have a “glocal” (global + local) focus.

Introducing The Villa Reino Resort

Villa Reino Resort is a premier destination for those seeking a luxurious, purpose-driven retreat in the heart of the Caribbean. With customizable programs, world-class amenities, and a deep commitment to holistic growth, it offers a transformative experience unlike any other. As the visionary founder, Jolander is dedicated to redefining luxury wellness hospitality through the H.E.L.P. principles, ensuring that every aspect of the retreat fosters renewal, personal growth, and meaningful transformation.

Learn More About My Villa Reino Retreats

Destination Retreat

Key Benefits

We believe to impact and affect global leadership change we must have a diverse and expansive approach. Any exciting adventure comes equipped with a destination, a splash of the unknown and the courage to step into the experience. Venues include destinations around and cruises customized for your organization.

While most retreats are scheduled on weekends, conference duration varies. These events are conducted in a trusted and will challenge your team to make the change you want to see in your organization. Participants are inspired and energized while gaining insight, clarity and tools required to scale their impact.

Your event can be local retreat or as a destination retreat.

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Dr. Jolander Headley TEDx 2025

For Your Convenience

Bringing It To You

It is not always the case that you can attend one of my programs in-person, or your organization has too many people who want to attend.   No need to pack bags or travel at all, and learn from the comfort of your own home or office.  Well, we believe no one should ever be left out so we offer two options: webinar and in-person service.

Virtual

Delivering Digital

We understand that it might be difficult to get to participate in one of my other services. In our online service we can still work together across any distance via video chat and webinars.  Some of my programs are also self-paced that you complete via your computer.

On Site

Delivering In Person

Sometimes you simply have too many people (more than 50) that need to participate in one of my programs. In those cases, we can come in to your organization or school, and conduct the program onsite.

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Jolander Headley Workshop

Masterminds

Bringing the Synergy of Energy

There is synergy of energy, commitment and excitement that participants bring to a mastermind group. Our facilitated groups offer a combination of masterminding, peer brainstorming, education, accountability and support in a group setting to sharpen your business and personal skills.

Mastermind Groups

Key Benefits

By bringing fresh ideas and a different perspective, my masterminds can help you achieve success.

Some of the key benefits you will experience in one of my Masterminds:

  • Increase your own experience and confidence
  • Sharpen your business and personal skills
  • Add an instant and valuable support network
  • Get honest feedback, advice and brainstorming
  • Borrow on the experience and skills of the other members
  • Study Leadership, Communications and Growth principles/practices in a group setting, create an action plan and have the group hold you accountable for fulfilling your plan and goals.
  • Receive critical insights into yourself
  • Optimistic peer support in maintaining a positive mental attitude
  • A sense of shared endeavor – there are others out there!

Masterminds are offered for 6, 8, and 10 week long programs, and includes all required materials.  Sign up for a 10 week program and receive one-on-one development PLUS 2 seats on any other programs I offer.

Contact Me About Your Mastermind

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Dr. Jolander Headley DISC Team Work

Lunch & Learn

Nuggets of Knowledge

Lunch & Learn events are sessions that typically lasts for between 30 and 45 minutes over a lunch hour.  They are small digestible bits of knowledge.

Lunch & Learn

Key Benefits

Some of the key benefits you will experience in one of a Lunch & Learn:

Because they take place during lunch, they are generally voluntary and have a less formal atmosphere than a structured training session or seminar.

A Lunch & Learn event is an opportunity for colleagues from different teams to meet and share their skills and expertise. It could be on-site or off-site.

Contact Me About Your Lunch & Learn

H.E.L.P. Experience

Available Options

  • Healing the Soul

  • Equipping with Excellence

  • Leading with Strategy

  • Plan for Purpose

Have Any Questions?

Contact Jolander Today
If you are you ready to discuss developing you or your team’s productivity, performance and profitability – please reach out, we’d be happy to create a program that works for you. 

You will always leave our programs with practical, applicable ideas and concepts you can use as soon as you walk out the door. Our training is designed to enrich your attitude, rekindle your determination to succeed, and expand your self-confidence. You will leave empowered and focused on your desired goals.

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Jolander Headley keynote speech
Dr. Jolander Headley Fiji 2025 Book Signing
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Jolander Headley Villa Reino Poolside
Dr. Jolander Headley Fiji 2025 Org Team
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Dr. Jolander Headley