It’s such a pleasure to have James as one of my business guests.  James was my hiring manager when I moved into the role of Business Manager for the Original Equipment Manufacturing (OEM) group at Microsoft. I certainly thank him for that opportunity. I enjoyed learning from him and am very pleased to still remain connected. Moving into that role provided rapid change, not only to both our immediate roles, but to the global environment of the OEM business. James has an amazing tenacity to stay the course while developing creative solutions which provide much needed sanity. I developed a deep respect and admiration for his crazy, mad business skills while he continues to remain cool and calm. His broad scope of business experience provides value to all levels of businesspeople, from entry level to senior executive. Enjoy the following interview with James.


We all have accomplishments and “opportunities for learning”. Many times, we focus too much on the opportunity for learning and don’t dwell long enough on our accomplishments. Each has the potential to provide future career growth. James, what are your three biggest business accomplishments? Were these repeatable and if so, what did you do to ensure these were implemented with future opportunities?

First Business Accomplishment: This question was intriguing to me as I have not truly thought about how to characterize over 30 years of business experiences into top three accomplishments. I believe business accomplishments are closely aligned with life accomplishments. Thus, I believe my first and greatest business success was graduating from college with a Computer Science degree and getting commissioned as a 2nd Lieutenant in the Air Force, becoming a Computer Systems Development Officer. This foundation of Technology and Leadership skills framed my future career and life achievements. I was the first-generation college graduate in my family with very modest beginnings. As an Air Force Officer, one of my first roles was running a section of the Data Center. The focus on continuous computer availability honed my thinking of precision in execution and contingency options planning. These were the days of “Maintenance Windows for Hardware and Software Modifications” and then ensuring all access was restored to the systems with new functionality immediately after the scheduled maintenance window. Here, I learned first-hand about building trusting relationships with team members from the perspective of “seeking first to understand, then to be understood”; as well as getting feedback from asking thoughtful questions. This in turn provided a platform for always “inspecting what I expected” with significant activities. What a unique opportunity for a 21-year-old!

James S. Pinckney
Second Lieutenant James S. Pinckney, USAF, Systems Development Officer

Second Business Accomplishment: Served as a key leader in the successful design and execution of Microsoft OEM division transformative organizational change to align OEM field teams into local subsidiaries around the world. This ambitious 90-Day initiative aligned over 1100 colleagues globally to strategically drive future revenue growth while instilling improved collaboration and accountability between OEM Segment and country leadership.

Details: The goal was to ensure the successful transformation of the Microsoft OEM Division from a direct line reporting structure globally into a bifurcated reporting structure strategically aligned, within 90 days. The primary goal was to continue to execute this multi-billion revenue business as a cohesive strategically aligned business unit globally. Rick Wong and I were selected by the Corporate VP, Scott Di Valerio, to co-lead the 90-day initiative. We outlined the strategy which was: Large Multi-National (MNA) OEM colleagues continue to report direct line to OEM division and local OEM colleagues globally report direct into the Microsoft Country Leaders structure. The OEM leaders in HQ would set the global strategy and metrics with input for the countries facilitating execution at the country level. The countries would receive revenue credit and all revenue globally would roll into the OEM Division. This fostered cooperation with the Country Leaders to maximize revenue opportunities locally, while maintaining a global strategy for the business to minimize conflict with Top 10 MNA OEM partners and Local OEM partners. This was an incredible opportunity to work with leaders across the world in a focused manor. Rick and I worked seven days a week, 14 to 16-hour days to successfully complete this ambitious initiative. A key lesson in dealing with many agendas and driving compromise demonstrated it was paramount to keep everyone focused on the primary goal of a global, strategically aligned business unit driving local execution for revenue growth. The initiative covered defining: Organizational Structure, Roles & Responsibilities, Business Cadence, Key Metrics, to name a few.

Third Business Accomplishment: Successfully transformed the Spiceworks revenue organization into a high-powered precision execution and results oriented team focused on business performance and customer impact. Key to success was establishing a culture of open communications and accountability operating as “One Team” across the entire company. There would have been limited to no success without the great collaboration with executives and cross-functional teams overall. Much of this work contributed greatly to preparing and positioning the company for a successful sale.

Were these repeatable and if so, what did you do to ensure these were implemented with future opportunities?

Yes, these all established shared goals and ownership at all levels.

The song says it so well, “Regrets, I’ve had a few, but then again too few to mention.” But let’s mention one or two, shall we? What career decision was the most significant decision you regretted and why?

I made the decision to stay in a Director role early in my career, turning down an opportunity for career growth, when I knew it was time to move on for professional growth. I stayed out of a sense of loyalty to my manager. It resulted in me feeling as if I was being held hostage. Key lesson learned was jobs roles should be mutually beneficial to all parties and if not, seek an appropriate opportunity to change. It’s your responsibility to make career changes and fully examine the rationale for your decision.  

On the flip side, what was your best career move and why?

My best career move was joining Microsoft mid-career. I took some risk as I was doing very well in my career working with various technology companies at the Vice President level; however, nothing as large as Microsoft. I went to Microsoft as I believed there would be greater opportunity for different roles to make contributions. Microsoft was the  company I have worked for the longest (nearly 10 years) during my career. I truly believe with great humility, I made significant impact while at Microsoft from multiple perspectives: contributing to business performance, my colleagues career growth and improving customers value. As a result, I grew professionally, and my family benefited economically.

You’re a complex businessperson with many layers. As a business leader you realize the value of brevity. As employees in any capacity we are always ‘selling’ ourselves.  If you were asked to describe yourself in one word, what would the word be and why?

Purposeful. I selected “Purposeful”  as I tend to always think about not just today, but the past and future to assess next actions to achieve the expected for whatever I’m engaged in. It’s like always having a north-star in mind.

Change is the only constant in business today.  Those who don’t embrace it are doomed for failure. Yet it’s one of those things that is tough to get agreement on and harder at times to implement. How do you approach change to ensure it is inclusive and has long term balance and impact?

I fundamentally embrace change by recognizing that the value of change must be clearly outlined and articulated. To ensure ownership and inclusiveness, the key stakeholders impacted and those required to execute the change must be engaged with the key rationale as well as provided a platform for collaboration on refinements and how best to implement. Just as important, what success looks like with the expected outcomes and metrics to measure success must be defined and clearly articulated.

Most of us have a slightly different personality at work vs. at home. What are you really like outside of work? How would your wife, JoElla, and your sons describe you?

I’m pretty much similarly focused on getting things done with a level of high integrity and strong values. I love just enjoying life (outings with my wife, a little golf and sometimes tennis) and eating different foods (Sunday and holiday brunches with family and friends). JoElla and my sons would describe me as too work focused, but a loving and caring husband and dad. My wife would say: “I do not need to listen to you – so stop it – you are not at work.” My sons would say, “Dad you were too hard on us when we were growing up, but we understand it was to prepare us for our future successes and failures.” Now, they just say: “That’s our Dad, he likes to educate.”

Learning is such an important element of growth. There are many ways we learn. We learn by doing, experience, practice, personal development, formally and informally and by involvement. Understanding and honoring learning styles is important for an individual’s career growth as well as a leader’s growth. How do you assess your employees learning style to provide them with the best opportunities? How do you adapt your learning style to your manager as well as your employees?

I work with employees on a development plan by identifying what the most important skills are for their current job and future aspirations that align with business needs. The learning style assessment from my perspective requires understanding how best to communicate with the employee by understanding their communications style as well. Regarding my learning style, I focus on open and effective communications with employees and my manager. I adapt to some elements of their style to foster greater engagement. I typically ask clarifying and probing questions to connect, resulting in effective engagement and alignment.  

I understand you are in the process of writing a book. Can you share a little bit about it?

Certainly! The premise of my book is to express a set of “LIFE” and “LEADERSHIP” tenets to help others find their individual foundation to greatness and “SUCCESS” in life and business. We each have a position in life that is only limited to the boundaries we set or let impede us. These boundaries are set based on our level of desire and commitment to pursue goals leading to outcomes. There will always be obstacles to navigate through, around or over. It is important to anchor ourselves with a level of integrity and morality in our pursuits for excellence. (Note: The book is due for release no later than early Q1 of 2021. We will come back to James for a follow up interview at that time.)

Companies and employees today realize the importance of giving back to the extended community. You share this belief. You have participated in the non-profit, Thumbs Up, which is a charity in Beaufort County, South Carolina, your hometown area. Thumbs Up supports under-privileged children from a holistic perspective of education and family support. Why is giving back so important to you? What is the most positive impact giving back has had on you and your family?

I came from modest beginnings; growing up in a family where kindness and helping others was always important.

My core is centered on education and hard work as a foundation for success. I believe everyone has any opportunity to give back and it does not need to manifest as bold sets of activities. Sometimes simple actions of goodwill have enormous impact. Such as: I will give a smile and greeting to a homeless person and other times I may provide a monetary gift. We tried to instill helping others as a core value within our sons, James II & Jeremy, and are proud of them as young adults.

We are all currently living under the cloud of COVID-19. How has this pandemic changed your life and your outlook both personally and professionally?

Clearly, everyone recognizes this pandemic is unprecedented certainly within the last 100 years as it can significantly effect mortality globally without a war.  It has further heightened my sensitivity to the value of every relationship personally and professionally. I continue to believe people overall are resilient and we will move past this in time and be better in the end; however, the impact will require us to find new and innovative ways to live safely inside and outside of work.

You’re a busy person. Husband, father, executive, community member. We hear so much about the continual challenges of work life balance. How do you achieve work life balance while remaining professionally successful? How does your family shape that balance?

I strongly believe work-life-balance is each individual’s opportunity to manage. What works for me, may not work for someone else. I set boundaries on priorities for work and family, which I modified as different stages of my family life evolved from small children to young adult phases. A key family priority (principle) was to never miss one-time or first-time events such as: graduations, recitals, games, parent-teacher sessions, etc., unless extreme emergency / extenuating work situation. I always called my wife everyday no matter where I was around the world. I worked long hours starting early every day and targeted to be home for dinner or by kids’ bedtime, then I would get back on the PC a few hours later at night after family time, if required, which for me was most of the time. I enjoyed my work and family and even on days when I was exhausted, I went the extra mile for either. There were many early Saturday mornings tee-ball, soccer, school activity, etc., where I wanted to sleep-in; however, instead I got up with my family and always found I enjoyed being at the activity anyway.

Having good role models is very important to everyone today. What do you feel we can offer each other to ensure that we are a good role model to each other?

I feel taking the time to reflect on the impact of “how”: What we do and say affects others’ lives is important with a level of frequency. Most importantly, what we “do” typically has the greater impact (good or bad) over what we just “say”.

What person has influenced you the most in your life and why?

My father is the person that influenced my life the most. He worked extremely hard at multiple jobs and was dedicated to seeing a better life for his children. Primarily, by making education and learning a top priority in addition to all the other things we were required to do. He and my mother always inspected our homework even as we got older, and they did not fully understand if it was correct. My father never walked away from a challenge and always appeared to do the right thing even when it was most difficult.

Knowing what you do today, what advice would you give your 20-year-old self?

I would say: slow down just a little and enjoy every different opportunity in life as this journey is long; however, continue to be who you are.

What are three key pieces of advice you have for today’s job seekers?

  • Believe in yourself; self-assess your skills and differentiators for the job opportunities you seek; Do not be afraid to modify your aspirations post-assess; then go after the job with great vigor.
  • Do not become discouraged as these are unprecedented times for everyone. Seek support from family and friends.
  • Resilience will always prevail!

If you were a superhero what would your superpower be and would you wear a cape?

Simply, my super power would be harvesting the best out of people. I definitely would not wear a cape! ?

What are the top 1-5 things that you are looking forward to in 2020?

  • Completing my book (Note: The book is due for release no later than early Q1 of 2021. We will come back to James for a follow up interview at that time.)
  • Professional interest only focused on select endeavors
  • Spending more time with family and friends
  • Building on my physical fitness to ensure quality of life
  • Global Covid-19 Pandemic impact being migrated with better therapeutics and eventually vaccines

Please include any sources that people can use to connect with you.

Jamespin00@hotmail.com