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Why mentors are pillars of MSSA—and essential to helping students succeed

Change is rarely easy, no matter how much we’ve experienced. This can be especially true for the nearly 200,000 U.S. service members transitioning to civilian life each year.

When it comes to changing or advancing our careers, having someone to turn to for advice, job skills, or even just an empathetic ear can make a big difference in how we navigate new terrain and pursue new goals. And as the COVID-19 health crisis has brought even more dramatic change to how we live and work, it is clear that human connection remains just as essential as ever.

That’s why mentorship has been a core component of Microsoft Software and Systems Academy (MSSA) from the start. Mentorship is fundamental to how we help veterans and service members make the shift to a new career in a corporate environment. As part of the program, two teams of volunteers—all full-time employees at Microsoft—are matched with participants to help them learn new technical skills in computing and IT, while other volunteers instill crucial “soft skills,” including those that build confidence around interviewing and adapting to unfamiliar corporate cultures.

These efforts stem from our desire to take a holistic approach to the ways we support service members transitioning to the civilian workforce. At Microsoft, we recognize the skills and experience these talented men and women already bring to our business. Through MSSA we create the pathways and opportunities that set them up to thrive.

MSSA mentors play a key role to bring it all together. Many have relevant military and/or technology experience that deepens the value of their connection with mentees. Through small-group, team-style mentorship, they become go-to resources for transitioning service members working to apply the unique skillsets they gained through military service to build successful careers in the private sector.

My MSSA mentors were a gateway into the professional life that lies beyond the military, providing crucial insight into technology careers. Even beyond that, my mentors were a lifeline; their eagerness to help in any way possible has been critical to my success, both in how I carry myself professionally and how I demonstrate my worth to potential employers.

Christopher Smith—MSSA graduate, May 2020, San Diego Cohort #7

The camaraderie between mentors and MSSA participants often bolsters the resolve of service members navigating new private-sector roles, who may feel uncertain about how their military experience has prepared them for a new career or stacks up compared to others with more tenure in their new workplace. Mentors can help assure and remind MSSA grads that veterans and service members embody some of the most sought-after skills and traits in the tech industry.

As a former transitioning service member myself, I think it is incredibly important to have a mentor in the tech industry. Veterans are some of the most resilient, creative, and adaptable people I’ve ever met. I feel the role of the mentor is to help mentees articulate their individual journey and the unique value they each have.

Heidi Connelly—MSSA soft skills mentor, Fort Campbell

But it isn’t just the mentees who benefit. “Something I’ve noticed in the six cohorts I’ve mentored is that mentoring is a two-way street,” says Casey Stabler, a longtime technical and soft skills mentor for MSSA at Hampton Roads. “I’ve left every cohort feeling driven to better myself and like I’ve learned something new.”

Beyond the personal reward MSSA mentors have expressed, these volunteers can amplify their impact through Microsoft’s Give program. Microsoft matches each hour volunteered by a cohort mentor with a $25 donation back to MSSA’s academic partners, which in turn safeguard the donations to fund scholarships that support future MSSA applicants.

To date, MSSA mentors have amassed over $270,000 in such donations from over 10,000 volunteer hours. Between January and May 2020 alone, more than 3,200 mentor hours were donated, spanning 14 MSSA cohorts. It is the single-biggest mentor hours contribution in MSSA’s history over a single cohort cycle —and represents the exponential impact MSSA mentors have on the future promise of the tech industry.

“The MSSA community—its mentors, students, and staff—can make transitioning a lot easier,” says Tristan Kevin Cacho, an MSSA graduate from May 2020, Schofield Barracks Cohort #2.

For more information about MSSA, visit, and for Microsoft employees interested in learning more or registering to volunteer as a mentor, visit