Decoding Digital

The Role of Transparency in Digital Transformation with Jennifer Byrne

By Ideas @ AppDirect / Oct 26, 2021

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Former CTO of Microsoft US and Principal Owner of Digital Future Consulting, Jennifer Byrne, has spent nearly two decades in the technology industry. She has been present for some of the most exciting changes at Microsoft and witnessed first-hand the techniques that people have used to transform organizations.

Jennifer’s own career has also been something of a transformation. Her unique journey to CTO is a clear example of why diversifying your experience can benefit you more than sticking to a traditional linear career path.

In this Decoding Digital conversation, Jennifer sits down with Daniel Saks to discuss her incredible experiences in the digital space so far, the digital heroes that have influenced her journey, and the role of transparency in implementing successful digital transformation.

Hit play to listen to the podcast episode or read on to find out more.

Pivoting into a career in tech

With the big-name companies and positions like CTO at Microsoft to her name, it may come as a surprise to learn that Jennifer hadn’t always plan for a career in tech.

In the late 90s, there was a lot of opportunity in the tech space, so Jennifer made a practical decision to pivot from her career in non-profit social services and go back to school for a year to learn computer basics.

She recalls that, at the time, the bar to entry was low. Her education and business experience led her to a role in a small consulting firm doing cybersecurity work for government agencies.

Here, Jennifer picked up technical skills which would frame many of her future roles and choices. Jennifer moved into sales, then alliance management, partner ecosystems, and other positions across various industries to gain broad competencies.

“I thought, well, I could either go deep, I could be the best cybersecurity engineer and network engineer I'd ever met. Or I could go broad, and leverage my domain experience, but for a bunch of different roles.”

In 2014, Jennifer began the Microsoft portion of her career adventure as chief security officer for the public sector group. She was working for the CTO—a role she would later move into.

“I realized that, although my technology portfolio expertise was relatively narrow, I had learned the business of technology. I knew enough to be able to think very strategically about how to get big customers, organizations and governments around the world to make big moves in their digital transformation journeys. And that's really what a CTO does.”

How to gain technical skills in a non-technical role

So how did Jennifer acquire enough technical knowledge to become CTO? She says the key was to just “lean in, hard.”

“Nothing worthwhile learning is easy to learn. It takes a discipline that you've just got to maintain throughout your career.”

One of the benefits of working at Microsoft is that you have access to some of the best technical talent in the world. By working alongside technical teams, Jennifer traded business knowledge for technical lessons that meant she could hold her own in any conversation, in any part of the business.

Jennifer says that committing to developing your technical knowledge isn’t for the faint of heart. Physics, statistics, software development, and more all play a part in giving you enough context to understand even some of the basics. But the beauty is, you don’t need to be an expert.

“The beauty of having a super broad portfolio and so much technology in the world is that there's zero expectation that any one person knows everything.”

Why transparency is key to digital transformation

Jennifer’s position meant that she had a keen insight into Microsoft’s operational and digital transformation when it began connecting consumers with cloud technology.

Jennifer recalls that before they implemented digital transformation into their own services and offerings, Microsoft did a lot of internal work first. They underwent a culture change that caused a ripple effect throughout the entire business. This started with taking a long, hard look at the problems that employees already knew existed and then doing something about them.

Jennifer credits Microsoft’s CEO, Satya Nadella, and CFO, Amy Hood, as key changemakers in this story. They didn’t just speak about transformation; they combined it with action. But arguably the most important and necessary part to the transformation was the transparency it required.

“We actually got really good at talking about trust and what trust really is. A big portion of trust is to be totally transparent, to show people that, when you say you are SOC compliant, you’ll show them all the audit controls, right? […] Give [people] total transparency, because you have nothing to hide, then there's no way they can't get to a place where they can probably trust you.”

At times, instilling this culture of transparency around technology was uncomfortable. However, CEO Nadella stuck with his promise to be transparent with his employees, partners, and customers. Following this top-down approach, Microsoft put into place processes, procedures, and programs that proved they were being as transparent as possible.

How to build trusting customer partnerships

When it came to delivering software services and platform services to market, Jennifer found that trust doesn’t necessarily happen just because you’re transparent. She describes it as a “function of time.”

In her role, it was important to communicate to the customer that it’s understandable if they don’t trust the company right away. But by forming a relationship, they can work together to build that trust and achieve their goals.

“If you set that expectation with a customer that look, I know you're not going to trust me today or tomorrow. That's not that's the way trust functions, not just in business partnerships, but also in our personal lives. So it’s no surprise that you can give yourself a little bit of space to not be perfect. Understand that trust is this journey that we take together.”

How transparent should you be when things go wrong?

There’s always a risk that something could go wrong with technology, so how do you stick to a transparent ethos even in emergency situations?

Jennifer says that the right answer is very, very complex for a very large organization. Her personal belief is to tell people everything they need to hear as fast as you can. The complicated part is working out what they need to hear.

While complete transparency is a priority, it’s not a viable option for large organizations until they can present their customers with information on exactly what has happened, and a plan for what to do next. It’s about being transparent but doing so responsibly.

Jennifer notes that this responsible yet transparent communication doesn’t only apply within the confines of emergencies; it’s also necessary in conversations between customers and the technical teams. Facilitating digital transformation is a lot about what will and won’t work, or what businesses can and can’t do. So it’s important to develop an open and honest dialog between the two parties.

Why anyone can be a digital hero

Jennifer firmly believes that implementing digital transformation happens at all levels, even in an enterprise-size organization like Microsoft. While she’s seen plenty of c-level executives put their careers on the line to promise big things from digital transformation, Jennifer credits those who put in the ground-level work as the most instrumental figures.

“The true heroes in my mind are the folks who did the quiet work of ushering that transformation through a company.”

Implementing digital transformation isn’t glamorous work. It can be difficult, detailed, and may adversely affect many people. It’s those who figure it out and do the hand-holding that get no credit, says Jennifer. But, in her opinion, they’re also the people who are the lifeblood of transformation.

Listen to Jennifer's discussion with Daniel Saks on the Decoding Digital podcast to hear more about digital transformation, including Jennifer's thoughts on preparing a workforce for a more digital world and what organizations and individuals can do to address the digital divide.

Check out the Decoding Digital podcast series for more insights from inspirational thought leaders and digital innovators. You can listen to the podcast on all the major podcasting apps, including Apple Podcasts and Spotify.