Get to know

Dennis Henry

Quick facts

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Lifelong Floridian
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Human Factors student
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Neurodivergent leader
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Ally and advocate

Five Questions with Dennis

You have a “Top Servant Leadership Voice” badge on LinkedIn. How would you describe servant leadership and why is it important to you?

Yeah, so for the longest time in my career, I was in management. I started as a low-level supervisor in my last company and rose up the ranks to become the Chief Operating Officer. Then I moved to Auth0 as an engineering manager and became a Director at what’s now a part of Okta. One of my biggest mantras when I was in management was “be a part of the team, not against the team”. Servant leadership is all about the idea that you work for the team, not the other way around. I think it's hugely important and one of the most key aspects of leadership in any organization. 

What does servant leadership look like during incidents? Any examples?

In incidents, it's showing that I am there to help others, that I am there to be a part of the process, and that I'm not above any sort of policies or procedures. I work for the team and more importantly I work for our customers. I'm not there to be forceful in any way with them. In fact, I strongly believe in a really good blameless culture and thus far I've been working closely with the organization to implement that. I've actually done a whole podcast with a different company about incident management and blamelessness because I believe it's strongly needed and something that a lot of organizations get wrong. I used to get it wrong myself. I didn't understand what the hell “blameless” meant. I thought it meant don't talk about who did anything, when in reality it's all about talking about mistakes but in a collaborative way where we’re bringing them to the table intentionally to look at what went wrong and how we can do better next time as an organization.

You're currently pursuing a Master's degree in Human Factors. What are "human factors" and what drew you to that area of study?

I’ve been really interested in incident response for a while now, but what I realized is that incident response is actually so much more than just “responding to incidents''. I wanted to dig deeper, so I did some research and stumbled upon the career of John Allspaw. He’s kind of a father of the incident management space. He was CTO of Etsy back in the day and has done countless talks about human factors in incident management, and reliability and resilience engineering. He did a Masters in Human Factors and strongly spoke to the connection between human factors and incident management. 

It's basically the study of failure—how people, processes, procedures, and systems fail and how to architect things to be more resilient. There's a lot of study of human cognition, physiology, psychology, adaptation, and how all those things interplay when failure quote, unquote “occurs”, and it's been fascinating. I'm four classes in of the ten class Master's program through Embry-Riddle Aeronautical University and so far I've been truly blown away by the content and just loving it.

You’ve held an impressive range of leadership roles from COO to technical lead roles (without necessarily being a “people manager”). What are your thoughts on the benefits of oscillating between management and individual contributor roles throughout a career?

I think what people need to understand is that leadership can be represented in many different ways. Even though I’m not directly managing people, what I'm doing now still involves a lot of leadership, I'm just leading people in a different capacity. I'm leading them technically, architecturally, and through thought leadership rather than managing people day to day. I made the choice to move into this role because at the end of the day when you get to a certain level, especially in an organization of Okta’s size—I've always fancied myself a hybrid leader where I'm both operating as an IC but also as a manager—but that becomes really hard to do when you're getting up to the Senior Director or VP level of a very large organization. When I worked for a company called HostDime as the Chief Operating Officer, it was a company of around 100 people and you're expected to wear multiple hats at a company of that size, but to truly lead at an exceptional level in an organization as a manager, you really need the ability to focus on management. The same thing is true as an individual contributor, to lead technically you need to be able to focus on that. In either type of role, you do your best work when you can focus where you need to. Thinking about my move into this role, I weighed managing people against dropping the technical leadership side like coding and building things, and the choice was obvious for me. Especially because we have a great career laddering system at Okta where ICs have the same room for growth on the technical track that managers do towards roles that take on more leadership up to the executive level.

As a lifelong Floridian, what’s the best thing about living in Florida?

The weather is definitely a good thing. The beach is somewhat nice. But I gotta say, the best part has got to be the diversity. I grew up in a very small town that was not very diverse and I didn't really see much outside of that when I was growing up, but I came to college at University of Central Florida here in Orlando and the amount of diversity that I was able to experience in this one little city has been amazing. You can also go down to Miami and experience wonderful diversity and the world of Hispanic culture that exists down there. You can go up to Gainesville, Jacksonville, you can go across to Tampa—there's a lot of wonderful communities in this state. We're not all “Florida Man”...I mean, we are, but we aren’t. There’s a flourishing LGBTQ scene too. Of course, I’m not naive to Florida’s worse aspects, and there are things that make me not love it as much as I did as a kid, but I still love being here. It's where my family is and that's truly important, too.