One specific piece of advice he received at Microsoft helped him transform his career at the company, where he eventually became an executive, and beyond.
"At Microsoft, my boss cared a lot about not only substance, but form," Medina tells CNBC.
In other words, Medina learned that how you say something is just as important as what you say.
"[My boss] instilled in me this belief: How you do anything is how you do everything," he says. What his boss meant by that, he explains, is that, "If you want to see long term impact in your life, act the part. Look the part. Speak the part."
Looking and acting the part isn't just about dressing nicely, Medina says. It means taking a whole different approach to work, and to coworkers.
Having come from Amazon, where the culture was numbers-driven and competitive, he says, Medina initially came across as "a bit abrasive" at Microsoft.
He quickly realized that if he wanted to succeed in this new environment, he needed to spend more time developing his social skills. Being able to communicate ideas effectively and show empathy, he learned, goes a long way.
It worked. After adjusting his communication style, he saw results. Medina rose through the ranks at Bill Gates' company, eventually becoming a director of business development and helping expand the company's business in Latin America and Canada.
Medina now works to model the values that helped him to his employees at his company Outreach, a sales automation platform.
If you want to get ahead, develop the way you present yourself, in person and online, the former Microsoft executive suggests.
To make sure you appear professional and friendly, "change your behavior and your tone in everything that you do," Medina suggests.