Executive Leadership and Values Program

Virtual Cohort Starting Wednesday, June 7th, 7:00 A.M. – 8:30 A.M. CT

The Executive Leadership and Values Program at Oak Bluffs Therapy Group is designed for high potential and senior executives who seek to hone their leadership skills and business acumen while exploring how they can live and work more authentically.

Our Facilitators

This program will be facilitated by Shawn O’Connor, Oak Bluffs CEO and Executive Coach, who also teaches graduate business courses at Harvard (his alma mater) and Alex Frascino, LMFT-S, Oak Bluffs DFW Clinical Director, who has an unparalleled track record working with countless top executives in a variety of developmental settings. 

Shawn O’Connor, MBA, JD
CEO and Executive Coach

Shawn O’Connor, CEO and Executive Coach, has extensive experience as a successful founder, business leader, and management consultant. For the last six years, Shawn has also taught graduate-level business courses and executive education at Harvard.  

Shawn has worked at McKinsey & Company, Lehman Brothers, and Mercer Management Consulting (now Oliver Wyman) and consulted for numerous fortune 500 companies. In 2006, he launched Stratus Prep, a global tutoring and admissions counseling firm. Over the next eight years, he grew the firm which served students in over 40 states and 50 countries without taking any outside capital. Shawn sold Stratus Prep to a private equity firm for an eight-figure valuation in 2016.

Alex Frascino, M.S., LMFT-S
DFW Clinical Director

Alex Frascino, LMFT-S, serves as Oak Bluffs Therapy Group’s DFW Clinical Director. In this role, Alex develops curricula and protocols for the practice’s individual and group therapy sessions while also providing individual and group therapy, leveraging an Accelerated Resolution Therapy (ART) advanced certification. Alex directly supervises other practitioners to ensure that each client at Oak Bluffs receives exceptional, comprehensive care.

Alex brings over a decade of clinical experience to her work at Oak Bluffs Therapy Group. During that time, Alex has developed a focus on collaborating with executives striving to improve their professional and personal lives.


Build a Robust and Supportive Network of Like-Minded Peers from Across a Variety of Industries.

Each cohort is strictly limited to 15 participants to ensure the highest possible levels of engagement. Secure your spot soon.


Wednesday Mornings

7:00 A.M. – 8:30 A.M. CT

The Seminar Begins Wednesday, June 7th


Week 1: Finding Your Authentic Leadership Style

It can sometimes feel like there is an ever-growing list of leadership styles: Servant Leader, Consensus-Building Leader, Visionary Leader, etc. But the truth is that effective leadership stems from developing an authentic style that best fits your values and your organization’s needs. This week, we will explore a variety of leadership styles and then hone in on the style or, more likely, styles likely to be most successful for you and your organization.  

Facilitated by Alex Frascino and Shawn O’Connor

Week 2: Managing Stress at Work and in Life

As executives, we will almost inevitably confront anxiety at work and throughout our lives. While anxiety can be a strong motivating force, how do we ensure that it does not overwhelm us (or those around us)? This week, we learn practical skills that will help us thrive personally and professionally even in the face of challenging circumstances. 

Facilitated by Alex Frascino

Week 3: Building Resilience

Even the most successful executives occasionally face challenges that prove difficult, if not impossible, to overcome. How do you build resilience when you are not accustomed to disappointment? This week, we will learn and begin to put into practice strategies for coming back from disappointments in a positive and productive way so that we can craft the future to which we aspire. 

Facilitated by Alex Frascino

Week 4: Managing Through the Full Economic Cycle

For many of today’s leaders, the Great Recession may feel like a distant and fading memory. For others, it may feel more like a haunting, potentially recurring nightmare. With persistent inflation, an inverted yield curve, initial rounds of layoffs under way, and the likelihood of a recession in the next six to twelve months, this week, we will refine existing management tools and perhaps develop a few new ones so that we maximize our effectiveness throughout the economic cycle.

Facilitated by Alex Frascino and Shawn O’Connor

Week 5: Living True to Your Values at Work

To optimize our work performance and feel good about ourselves, it is essential that we live true to our values at work (as well as at home). But this may be easier said than done. This week, we will explore the following questions: What are my core values? Is my work today consistent with these values? How could my values further enhance my work performance? How do I live true to my values at work if/when some of my colleagues have distinct value systems?  

Facilitated by Alex Frascino and Shawn O’Connor

Week 6: Negotiating Distinct Generational Perspectives in Your Organization

Each generation has a unique set of collective attitudes and attributes when it comes to work and life. In today’s workplaces, the perspectives of baby boomers and Gen X often conflict with those of millennials and Gen Z. This week, we will explore these generational differences and their causes so that we can build more cohesive, more productive organizations where these distinct perspectives represent a strength, rather than a point of contention. We will also have a frank discussion regarding the best way to address others’ perspectives that run counter to your core values. 

Facilitated by Alex Frascino and Shawn O’Connor

Week 7: Finding and Developing Your Personal Passions

Many executives have achieved great success because of their passion for their work. Many of us may be fortunate to love what we do and, even more broadly, to simply love working. Yet, research overwhelmingly indicates that we will be even more successful at work and happier throughout our lives if we can find another true passion (or two or three) outside of work. This week, we will share our personal passions, explore those passions that we may not have yet cultivated, and explore how these passions fit together with work. 

Facilitated by Alex Frascino and Shawn O’Connor

Week 8: From Globalization to Regionalization

Covid-19 illustrated the fragility of global supply chains. Trade tensions, particularly between the U.S. and China, have exacerbated a shift from globalization to regionalization. This tectonic shift in the world economic order will profoundly affect businesses large and small. It will meaningfully impact not only manufacturers but also the providers of professional services. This week, we will explore how each of our organizations is likely to be impacted by the shift from globalization to regionalization and how we can best lead our organizations through this and other challenges that lie ahead.  

Facilitated by Alex Frascino and Shawn O’Connor

Registration Fees

$ 990 $ 799

Full Seminar

  • Eight-Week Seminar
  • Small Virtual Cohorts
  • Ongoing Resource Database
$ 2,750 $ 2,499

Full Seminar & Indiv. Coaching

  • Full Eight-Week Seminar
  • Weekly 60 min, 1:1 Coaching
    Sessions with Alex Frascino
$ 5,450 $ 3,399

Full Seminar & Indiv. Coaching

  • Full Eight-Week Seminar
  • Weekly 60 min, 1:1 Exec. Coaching Sessions with Shawn O’Connor

We also accept payment from employers who wish to sponsor their employees for this program.

Group members may wish to complement their participation in the cohort with individual executive coaching with Shawn O’Connor or individual coaching with Alex Frascino.  

Please reach out to us at (214) 471-5138.