War Room to Board Room: Recent Episodes

MaShon Wilson

This short episode overviews all the topics we plan to cover: transitions, careers, and leadership. Some topics include: Preparing to Transition (18-24 months out), Finances, VA/Medical, Positioning yourself, Career, Networking, and Management/Leadership Challenges.


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Alana is a Holistic Health Practitioner, Women’s Health Advocate, Author, and Entrepreneur. She is a graduate of the United States Naval Academy at Annapolis. She served as a Surface Warfare Officer during her time in the Navy.


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Wayne Robinson is a dynamic thought leader in talent and organizational transformations, Advocate of Empowerment, successful Entrepreneur, and Award-Winning Veteran. His journey epitomizes the essence of transition- igniting change and purpose in individuals facing life and career evolutions.

As a seasoned Global Leadership Strategist, Robinson orchestrates the rise of exceptional leaders in critical industries like healthcare, technology, and business. At Moderna, as Senior Director of Global Talent, he marshals the brightest minds to spearhead groundbreaking healthcare solutions, with a vision to elevate global well-being.

During his tenure at Google, Robinson played a pivotal role in founding The Google School for Leaders, cementing the company's executive echelon with strategic acumen to navigate complex global landscapes. At Deloitte, he co-founded the Deloitte Resilience Academy, redefining leadership development through grit and practical growth.

Robinson's strategic leadership ethos is deeply rooted in his 26-year military journey, where he served as an Army Command Sergeant Major and later dedicated nearly a decade to supporting veterans. His initiatives, like Vets in STEM and Student Veterans of America, have set benchmarks in aiding veterans' transition into civilian life and expanding educational opportunities. His impact extends to advisory roles with the US Department of Veterans Affairs, where he provided strategic counsel on programs supporting veterans and their families' educational and training needs.

Robinson's academic accolades include an MBA from the University of Chicago Booth School of Business, complemented by certifications from MIT Sloan and The Wharton School. His unique blend of education and experience embodies the transformation driving change, empowerment, innovation, and integrity-driven leadership in shaping the future


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BG Bernie (BBB) Banks is the Director for Rice University Doerr Institute for New Leaders, Former Associate Dean of Leadership for Northwestern University’s Kellogg School of Management, Independent Director for Customer’s Bank, Senior Advisory Partner for Sentinel Partner (PE Firm), Principal of Bank’s Talent Solutions, and former US Military Academy Professor and Department Head for Behavioral Science and Leadership, and Former White House Aide/Staff Officer. He was a Ranger-Qualified Aviation Officer and Artillery Officer, commanding organizations from the platoon to the battalion level. He holds a BS from the United States Military Academy, an MPA from the Harvard Kennedy School, an MBA from Northwestern Kellogg, an MA from Columbia University’s Teachers College, and a PhD and MPhil from Columbia University.


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Dr. Jolene Erlacher is an adjunct faculty member, a leadership coach, and a professional speaker. She works with U.S. Army Special Operations Soldiers and focuses her research on leading intergenerational teams. She is a long-time military spouse. She is a graduate of the University of Saint Thomas.


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Jabe is an IFBB bodybuilder and personal trainer at Equinox, He is the founder of War Ready Clothing Brand, and a screen actor in the Los Angeles area. He was a Ranger-Qualified Airborne Artillery Officer and my battle buddy from the 173rd Airborne Brigade. He is a graduate of Indiana University and Purdue University in Indiana.


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TJ is a Senior Director, Engines Strategy and Growth Leader for Honeywell and U.S. Army Reserve Aviation Officer, Former National Guard Aviation Battalion Commander, and Former Product Director for Dow Chemical. He was an active UH-60 Blackhawk Aviation Officer before leaving active duty. He is a 2000 graduate of West Point and a 2011 graduate of The University of Chicago - Booth School of Business.


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Landon is a First Officer/Pilot for Frontier Airlines, Volunteer with Several Non-profits, and a Real Estate Developer. He was a Ranger Qualified Aviation Officer for the 160th Special Operation Aviation Regiment. He is a 2010 graduate of West Point.


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Hon. Adrian Perkins, JD is a private equity partner and a teaching fellow at the University of Chicago. Adrian is a Board Member for Service to School, and HLS’s Visiting Committee, United States Conference of Mayors, and the Federal Communications Commission. He served as a Field Artillery Officer. He is a graduate of the United States Military Academy at West Point and 2008 Class President. He is also a graduate of Harvard Law School, where he was a part of the Harvard Business Law Review and a Pat Tillman Scholar.


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Kafi is an Operations Lead for CEO Advisory + DEI at Accenture, Former Lead Associate at Booz Allen

Hamilton, and a Manufacturing Project Manager at Fairbanks Morse Engine and National Air Cargo. She

served as both an active and National Guard Military Police Officer and former FW West Point Outreach

Officer. She is a graduate of West Point, George Washington, and Georgetown University McDonough

School of Business.


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Alijah Talley is part of the Affinius Capital(formerly USAA Real Estate Development) Team, an avid Real Estate Investor, and Executive Director of the Qonnection . He also served as Air Defense Officer and West Point Diversity Admissions Officer. He is a graduate of the United States Military Academy at West Point and University of California, Berkeley Haas School of Business.


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Shawnette Rochelle is the President, an executive coach, and a public speaker at Excellence Unbounded. She also served as a Military Police Officer, Operations Research Analyst, and West Point Assistant Economics Professor. She is a graduate of the United States Military Academy at West Point, University of Pennsylvania Wharton School of Business, and Georgetown University.


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Alice Garcia is a Senior HR Strategist at a Large Bank and a Real Estate Investor/Property Manager. She also served as a Business Strategy & Planning Director at USAA, an Adjutant General (HR) Officer and West Point Outreach Admissions Officer. She is a graduate of the United States Military Academy at West Point and St. Mary’s University.


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Marcus Harmonis a consulting manager at Simon Kucher. He also served as a Ranger NCO in the 3rd Battalion of the 75th Ranger Regiment and Reconnaissance Surveillance Leadership Course at Fort Benning. He graduated from the University of Dayton in Ohio and Georgia Institute of Technology – Scheller School of Business.


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Albert Vallejos is a Regional Service Manager at Siemens Healthineers and Co-founder at Service First Jewelry. He also served as a Field Artillery Officer and a West Point Diversity Admissions Officer, Partnership Manager at Johnson & Johnson, and Project Manager at GE Healthcare. He is a graduate of the United States Military Academy at West Point and New York University Stern School of Business.


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Devin T. Adams is an Associate Attorney at Big New York Law Firm, President and Founder of WarBevCo (alcohol beverage production/distribution company), and the Mala Mia Mezcal Brand. He was an Airborne, Ranger-qualified Artillery Officer in the 173rd Airborne and West Point SE Outreach Officer. He is a graduate of West Point and Vanderbilt Law School. 


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Michael Burns is the Managing Partner of Burns Brothers, SXSW Advisory Board Member, and Co-Founder at Service First. He also served as an Aviator (Apache AH-64 Pilot), the Head of West Point Diversity Admissions Officer, the Head of Diversity at Citibank, and the Head of Transformation for its Call Centers at Conduent. He is a United States Military Academy graduate at West Point, University of Notre Dame – Mendoza School, and Columbia University – Executive & Organizational Coaching Program.


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Aditya “Sunny” Sundaresan is a Content Creator (4 million viewers) and Founder of Zuvier (Adventure x Travel Fashion Retail). He also served as an Infantry Officer at Fort Wainwright, AK. He is a graduate of the University of California at Santa Barbara and a current student at New York University – Stern School of Business.


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Jerry Varnado is a part of the cross-functional Strategic Initiatives at Meta (formerly Facebook) and is an Angel Investor. Before his time at Meta, Jerry was Chief of Staff at both Hewlett Packard Enterprise (HPE) and ChargePoint. He also served as Air Defense Officer and West Point Diversity Admissions Officer. He is a graduate of the United States Military Academy at West Point and Columbia Business School.


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Jessica Lucas, STMP (Senior Talent Management Practitioner) is the Director of Talent and Culture at Risk3sixty, after time as both an active duty Army AG and Georgia National Guard AG Officer. She is a graduate of West Point and the Georgetown University – McDonough School of Business. 


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Michael Dames is the President of Lusk Reserves (Search Fund) and President of Colorgraphy, after time as a Process Engineer and Operations Manager, Airborne, Jumpmaster, and Sapper-qualified Engineer Officer. He is a graduate of West Point, Missouri Science and Technology University, and the University of Chicago – Booth School of Business. 


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Shante Frazier is the Founder of Wellcapped, a rent-the-runway style wig company, after time as a Management Consultant and Retail Merchandising manager, an Progressive Insurance Analyst, National Guard Intelligence Officer. She is a graduate of Spelman and New York University Stern School of Business.


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Omar T. Ritter is a Senior Vice President, Diversity, Equity, and Inclusion at Wells Fargo, after time as a Corporate Finance Executive and Investment Banker, Cavalry Officer, and West Point Outreach Officer. He graduated from West Point and Columbia University’s Business School.


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Kenny Vaughn is a Senior Manager, Transformation & Operations at Indeed, after time as an Air Defense Artillery Officer and West Point Head Outreach Officer. He graduated from West Point and the University of California – Haas School of Business. 


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Marcus A. Jackson is a Management Consulting and former Operations Executive in (Supply Chain and Healthcare), after time as both a Field Artillery and Intelligence Officer. He is a former West Point NCAA D-I Football Player. He is a graduate of both West Point and Columbia Business School.


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Juliet, BSN working Neonatal Intensive Care Unit for University of North Carolina Healthcare system, after time as an Airborne, Combat Engineer Officer and an EMT/Paramedic. She is a graduate of West Point and the University of North Carolina at Greensboro. 


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Stephane, MBA and MS in Design Innovation, is the CEO and Founder of TruFiktion. TruFiktion is an education technology company that leverages comic books to teach untold stories from underserved and underrepresented communities. He served as a Special Operations Engineer Officer and then an Accenture management consultant. He graduated from West Point and the Northwestern University – Kellogg School of Management.


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Anthony G. Ruizcalderon is the President/Co-founder at Circular Hospitality, after time as an Infantry Officer and a Private Equity Vice President at Heitman based in Chicago and London. He graduated from West Point and the University of Chicago – Booth School of Business. 


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Natoshia Clinton is an HR Business Partner at Hover and Cornell Executive Coach. After time as an AG Officer and a Cornell Leadership Program Officer/Instructor/Leadership Coaching. She is a graduate of West Point and Cornell University. She is also a mother of two, sharing the challenges of balancing family life. The key tenants she shared with us are Introspection, Mentorship, Collaboration, Discipline, and Humility.

"Take inventory of the things you enjoy. I enjoy connecting with people" "Is it aligned with who I want to be in the world" "If there was a problem to be solved, what problem would you ask me to solve?"

"Lean heavy into unpacking who I am and who I want to be in the world"

"Be grateful for the lessons you had to learn, the experiences you had to go through. Be in gratitude for the leaders modeling the behaviors you want to emulate”

"I used to view it [Black, female West Pointer] as a hindrance, but now I embrace my unique lens and as a superpower."

  • Military brat settled in Brooklyn, NY, before coming to West Point.
  • Mentors like LTG (R) Linnington recommend she come back to West Point Admissions.
  • MBA at Cornell led to a great deal of self-discovery, both personally and professionally
  • Business functions like Human Resources, Marketing, Finance, Banking, etc.
  • Then a mentor recommended returning to Cornell to help MBAs figure out who they want to be as leaders.
  • Becoming an executive Coach, "Learning how to unpack all the magic inside her."
  • Her manager was the type of mentor that knew what she was capable of, the ability to create and co-design an elective, "Leading across differences."
  • COVID and Broader societal awareness of racial injustice pushed her to make a career change
  • She found COVID that she liked a less stressful life, so when the "Return to the office" came. She decided to make a change.
  • She pursued a transition path through Breakline; she optimized for culture versus chasing the brand.
  • "What kind of work excites you? What gets you up in the morning?"
  • In what areas do I like doing things?
  • "A focus on her as a person, holistically."
  • It is hard to uncouple the things I do (programming) versus passion/enjoyment.
  • Have friends outside of the military, then you'll start to broaden your horizon.
  • There are opportunities outside of the military and government.
  • Breakline is an easy and fast pass, sales, account management, customer-facing, "invitation to some custom tables,"
  • "Be Comfortable taking a walk in your career exploration after the military."
  • The Alchemist "The Treasure is inside of you."
  • Adam Grant's podcast
  • Brene Brown
  • Oprah (Fairy God-mother) – Super Soul Sunday: Interviews with influential leaders
  • Oprah's Journal
  • "Lean heavily into unpacking who I am and who I want to be in the world."
  • Who am I in the world versus who someone else tells me I should be
  • "Be grateful for the lessons you had to learn, the experiences you had to go through. Be in gratitude for the leaders modeling the behaviors you want to emulate
  • Humility "Being more receptive to feedback in the military, especially" taking and processing the feedback as a young leader.
  • Being disciplined and taking time to transition (12+ months) well
  • Do you have transferrable skills? Is the graduate school required? Writing my resume?
  • Finding an assignment where you have the headspace to think? Balancing the requirements
  • Identity: There are only 300 or so Black female West Pointers worldwide. "It is the icing."
  • "I used to view it [Black, female West Pointer] as a hindrance, but now I embrace my unique lens and as a superpower."
  • Now I stand proudly in my skin, so perhaps I bring another 1 or 2 behind me.

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Paul Bryant, Esq. is an Associate at Cravath, Swaine,& Moore LLP in New York, after time as an Infantry Officer and a West Point Diversity Outreach Officer. He is a graduate of both West Point and Columbia Law School. He balances the challenging demand of Legal Transactions and Mergers & Acquisitions while still making time for his beautiful family and young daughter.

“Law School gives you a broad-based education with jargon and tools, but the firm is the finishing school for client, organization, and project management.”

“Finances-Saving Money is one of the things that scares most junior military officers.”

“What can I do now as 2LT to be a great attorney? My mentor responded focus on being a great 2LT and taking care of your soldiers.”

“Have the right attitude and reputation, which enables greater latitude in your role.”

  • Build your 4–5-year plan and then factor in contingencies
  • Focus on being a great officer FIRST, and knock out BOLC/KD assignments. Then once settled, start thinking about other phases.
  • In the military, the habits you build are based on your attitude.
  • If you think you can wave things off in Army, you’ll wave them off as an attorney.
  • Military habits are what distinguish you from your peers.
  • Standardized Tests for Law, Business, and Medicine are full-time jobs.
  • LSAT studying 6-12 months before applying, developing a study plan
  • Saving Money – When the Army money stops, what am I going to do
  • Looking at financial resources early
  • He did not have a family when he transitioned
  • Leverage your network, “Life is a people sport.”
  • If you do not have the stories, you cannot make those up or the respect that comes with them.
  • Consider what assignment(s) would enable you to best transition, “Ranger PL vs. Staff Position/Broadening Assignment.”
  • Key Development (KD) jobs are usually the least flexible.
  • Selecting Broadening Assignments (Minimal Field Time)
  • As Civilian Job as possible
  • Communicating his intent with his manager, enabling greater flexibility
  • Leveraging your network to see what’s the requirement and if it’s possible

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Mr. William T. Osilaja, a Human Capital Consultant at Deloitte, LLP, Infantry Officer, Former Diversity Outreach Officer, and Charter School Business Operations Officer, explains his strategy and tactical steps to transition.

Before coming to West Point, Mr. Osilaja was a native of Evanston, IL. He graduated from West Point (BS) and the University of Michigan – Ross School of Business (MBA). During our conversation, he explores his decision to serve, transition, and choose his subsequent career.

“Everyone wants to save the world and be a millionaire.”

“Bloom where you’re planted”

Key Points:

  • Understanding different types of people and personal awareness of your identit(y)/(es)

Multi-racial

Immigrant parent

Grandparent and parents served

  • Understanding your passions and leveraging your skills (People Management, Operations)

  • Developing muscle of checking in with yourself (Constant introspection/reevaluation)

  • Humility and Perception is essential (Direct Military Feedback vs. Indirect Civilian Back)

  • The importance of communication in different environments

Low context vs. high context communication

Consulting leverages improvisation of “Yes and …” versus the hard yes and no of the military

  • Culture selection is vital as the initial shift/shock can quite significant

  • Deloitte’s Business Chemistry and Michigan Model of Leadership

Communication, learning, and leadership styles

Creator, collaborator

Increased self-awareness and better communication

  • Greater intentionality in the transition process

Talk to more mentors to collect as many data points as possible

People are full of information, so leveraging them and transition programs like MLT

Please connect with Tunde Osilaja on LinkedIn.

https://www.linkedin.com/in/tunde-osilaja-33a39175/

https://youtu.be/uyHFz_SMN-U


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Dr. Hise O. Gibson, a Harvard Business School Senior Lecturer, Combat Aviator, and Retired Army Colonel, explains his strategy and tactical steps to transition after 25 years of service. 

Dr. Gibson is a native of Lubbock, Tx, before coming to West Point to play football. He is a graduate of West Point (BS), the Naval Postgraduate School (MS), and Harvard Business School (DBA). During our conversation, he explores his decision to serve, transition, and choose his subsequent career while balancing family life.

“Don’t be scared of transitioning.”

Key Points:

  • Finding time to think about your transition (24 months before)

  • Putting yourself out there, leveraging your network with mentors/peers

  • Recognizing your unique value

Please connect with Dr. Gibson on the HBS Faculty Page and LinkedIn

https://www.hbs.edu/faculty/Pages/profile.aspx?facId=660784

https://www.linkedin.com/in/hisegibson/