In this installment of the IT Leaders Fast-5 — InformationWeek’s column for IT professionals seeking peer insights — Rob T. Lee, chief AI officer and chief of research at SANS Institute, describes how moving too quickly with AI can cause “everything to tilt,” using a recent example from his own team. In Lee’s experience, employees will often “default to older processes” so introducing AI too quickly without organizational buy-in can trigger resistance and stall progress. He also discusses why curiosity and the will to keep learning are essential to working in technology today.
At SANS Institute — a cybersecurity training, certification and research organization — Lee focuses on AI governance and security, advising boards, CISOs and government leaders on how to deploy and defend AI systems. He also serves as an amicus curiae technical advisor to the Foreign Intelligence Surveillance Court through the U.S. Department of Justice.
The Decision That Mattered
What decision — technical or organizational — made the biggest difference recently, and why?
I’m really trying to influence not only my organization, but other organizations, by instilling a learning mindset. The biggest influence I’ve had isn’t just on [how to deal with] cybersecurity, but really trying to persuade my friends, neighbors and co-workers to admit how much they’re struggling [with AI], and to be okay with that. Just go try — you’re not going to be running the marathon tomorrow.
You need to work on AI like you exercise — on a daily basis. You need to spend about 30 minutes daily learning AI. It’s also about leading by example, including demonstrating vulnerability by saying “Hey, I’m struggling, ‘Don’t come to me for all the answers that I might not know.'”
The Hard-Won Lesson
What didn’t go as planned recently — and what did it force you to rethink?
People default to older processes. It’s really hard once you become almost an “AI superpower” because you start moving at the speed that AI is able to achieve.
A recent use case example is that there was a discussion [at SANS] about creating a microsite. I was told it could take weeks or a month and the team would need to do site design, AB testing — all those things.
I used Replit [AI] — and not being a skilled web designer — I threw together a microsite in about an hour and a half. I shared it with the team leads to have a discussion on it, and they liked it, but then they shared it with the team that does website design.
Everything kind of went tilt because you end up challenging old dogma — at the same time showing the potential velocity of AI when not everyone is caught up yet. There’s a palpable fear in how fast you went and what it means for what your team does on a daily basis. There’s a balance between the shock and awe of being able to leverage AI and getting the organization to mentally open itself up to using these new technologies. It’s something I think most organizations are going to struggle with, even outside cybersecurity.
It causes a disruption amongst your normal workflows … that push/pull is definitely hard. More than just the fear of the AI, it almost flies in the face of the folks that said it would take weeks or months and then you almost say, “Well, you’re wrong.” And people just don’t like being told that they’re wrong.
But, I’m definitely sensitive to how that’s perceived by current teams. Introducing it, messaging it right — that needs to be shown by the example of the leaders. I may have messed up by not messaging it right to the other leadership. [The response] was either very positive or very negative — it was very polar. Ultimately, the organization said, “Let’s do it,” and everyone was on board with trying to figure it out.
The Talent Trade-Off
Where are you investing in talent right now — and what are you consciously not investing in?
It’s very easy to say that I would like folks who are AI skilled to come in, but that’s way too binary, and it doesn’t exist right now. What I’m really looking for is a capacity and will to consistently learn, and a passion to be the expert in your job.
The desire to learn almost becomes the most important quality in hires. It’s that ability to get through those initial humps that are a struggle. It’s similar to exercising — it’s hard to motivate yourself to go in there and feel frustrated. I always tell people if you’re not frustrated, you’re not learning. If you’re not frustrated, you’re one of two other things — you already know it, or you don’t care.
The External Signal
What recent external development is most likely to change how your organization operates, even indirectly?
Some of the recent developments [with AI] are really about trying to figure out workflows that can be optimized through the tools that are available to the workforce. Working through a couple workflows with folks to get them going is essential, but that requires mentorship. When I’m starting out with folks [on using AI], we’re using ChatGPT for basic analysis, or even writing and consolidating email or Slack messages. You could use AI to potentially make suggestions on how to improve message receptivity. Just basic communication input through AI has been one of the biggest advantages in the company to be able to change our cultural understanding of each other. So I start small.
The Perspective Shift
What have you read, watched, or listened to recently that changed how you think about leadership or technology — even slightly?
I plowed through this book in about a weekend, I listened to it on audio. It’s Pablos Holman’s book Deep Future: Creating Technology That Matters.
It gets to the core of how different technologies need to be viewed, and the concept of hacking — just figuring things out. It gets you to pause and look at things through a different lens.
My biggest thing is to never stop learning. And learning sounds very kitschy, but … [learning] is not just for work purposes …It could be learning a new sport, painting or piano. Podcasts that offer that kind of inspiration and learning are also helpful for me.
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