A New Focus on Technology Leadership Careers

Thank you to everyone who participated in GeneCon last week. I loved how a long-time community member described it below:

“I love the new format. It’s like a Viewing Party, Panel, and Ask Me Anything, all in one.”  
— Luke Rettig, Senior Director, Target

I’ll be sharing more about the updated programming objectives for the Enterprise Technology Leadership Summit (formerly known as DevOps Enterprise Summit) in another article later. For now, I want to highlight three areas of focus in the 2024 Call for Presentations (both are already open—Europe Virtual & Las Vegas).

Transformation Experience Reports

These have been the hallmark of the conference over the last decade—illustrating how technology leaders have played a pivotal role in helping their organizations succeed.

Generative AI

What are organizations at the frontier of this field doing? What is possible? How can these tools and techniques be replicated in other organizations?

Technology Leadership Careers

How can technology leaders make even larger contributions to their organizations and more effectively accomplish their personal career objectives?

I find the third topic related to technology leadership careers incredibly exciting. We’ve explored this topic at our conferences, such as thriving through disruptions, individual contributor career tracks, and more.

However my observation is that many technology leaders feel like their career has stalled, and they’re not able to advance their own personal goals.

And so, at GeneCon, we explored how leaders can better advance their careers and personal goals. What was so exciting to me is that these skills are teachable and are things that you can take responsibility for.

Below, I’ll summarize some of those fantastic teachings.

All the amazing sessions from GeneCon, are already available in the IT Revolution Video Library for anyone with Individual or Enterprise Memberships. Upgrade here!

(By the way, the unlimited user Enterprise Membership is $5,000/year (normally $15,000/year) through December 13, 2023. Contact [email protected] to learn more.)

The Secret to Keeping Your Career On Track

Dr. André Martin, author of Wrong Fit, Right Fit, previously served as the VP of PeopleDev at Google, and was Chief Learning Officer for Nike, Target, and Mars.

In his session, he shared how technical talent was highly valued at Google versus more traditional companies like Nike, Target, and Mars. I asked, “On a scale from 1-10, to what extent do you think technology leaders can thrive in the non-tech giants? (1 = not at all; everyone should go to the tech giants, 10 = you can be just as successful)

His answer was: “10*” (with an asterisk). He believes you absolutely can but with a couple of caveats.

We also explored questions such as:

• If I know where I want to go, how do I know if I’m actually making progress?
• Is there a limit to how high I can go here? If so, how high is it? To what degree does the Venn diagram of “what company wants” and “what I want” sufficiently overlap?
• What advice would you give to technology leaders who are looking to redefine their career paths, especially when they feel undervalued or overlooked?

Watch the session here.

Annual Performance Review Role-Play

Many of you were blown away by the plenary session in Las Vegas featuring Paul Gaffney, who currently holds the position of Chief Digital Officer at Omni Logistics. Previously, he was the head of software for The Home Depot, CTO of Dick’s Sporting Goods, and CTO and head of supply chain at Kohl’s.

Paul had made the observation that many technology leaders might be doing their subordinates’ jobs instead of their boss’s jobs. So, during a breakout session, I asked him to do a role-play with Jeff Gallimore, where Jeff played his boss, demonstrating a lack of interest in having Paul take over his role.

It was an exceptional modeling demonstration of how to initiate such a conversation, and what to do when there are clearly issues that need to be fixed beforehand.

During GeneCon, Paul and I engaged in another role-play where I assumed the role of the boss conducting his annual performance review. The primary advice he received was, “Keep doing what you’re doing.” This is not particularly helpful advice and certainly doesn’t help advance one’s career.

In the role-play, Paul once again wonderfully modeled the art of taking responsibility for obtaining the feedback he needs, even if it might be difficult for him to hear, and making it possible for his boss to share it, resulting in some surprising feedback.

Watch the session here.

How to Progress in Your Career as a Technology Leader

Ian Eslick is Chief Technology Officer, Enterprise Architecture and Engineering at US Bank. He started there in 2019 after spending years leading a team of 180 people at Amazon. He and I spoke about leader development at US Bank, and he had so many fantastic observations about what can enable it, what hinders it, and what we can do as a community to bring teachable skills to bear.

He provided guidance similar to what you might offer to technology leaders who feel like they’ve hit a ceiling and aren’t able to progress their career: either make a more significant contribution to the organization or strive to achieve their personal goals.

I found the emphasis on succession planning at US Bank particularly intriguing—after all, one can’t move to a different role (laterally or up) without having someone to replace you. Ian provided guidance that he has offered to his team on the steps they could take to fill his role.

He also provided a laundry list of skills and competencies that senior technology leaders should possess and the things they need to care about. His insights and perspective offered fantastic guidance on what it takes to be successful as a senior technology leader.

Watch the session here.

The Impact of Building Connections

Admiral John Richardson served as Chief of Naval Operations for four years, the highest-ranking officer in the US Navy, responsible for overseeing the efforts of over 600,000 personnel. Now that he’s retired from the U.S. Navy, he serves on numerous boards of directors, including Boeing, the world’s largest aerospace company, and Constellation, a Fortune 150 company, which is the country’s largest supplier of carbon-free energy. 

His framework of Competence, Character, and Connections has gained traction within this community as a way to articulate the skills required by leaders. And I’ve hypothesized that technology leaders often don’t have enough or adequate connection with their peers or with their bosses.

As one gets more senior, the needed skills for success are less about Competence and depend more upon Connections. He sums it up so well when he says that the goal is to gain their confidence and trust, especially as one’s area of responsibility grows and the amount of regular oversight goes down.

He shared some remarkable stories of how he’s been in situations where he built Connections, and in one case, having to start from zero, and the impact that had on his ability to get the outcome he, his team, and his organization needed.

Watch the session here.

How to Watch These Talks

I’m so delighted that these incredible experts have shared advice that is applicable to every technology leader across all levels of the organization, and I look forward to even more content like this at our upcoming events.

The leadership talks I mentioned above (see the playlist) as well as all the amazing sessions from GeneCon, are already available in the IT Revolution Video Library for anyone with Individual or Enterprise Memberships. Upgrade here!

(By the way, the unlimited user Enterprise Membership is $5,000/year (normally $15,000/year) through December 13, 2023. Contact [email protected] to learn more.)

- About The Authors

Gene Kim

Gene Kim is a Wall Street Journal bestselling author, researcher, and multiple award-winning CTO. He has been studying high-performing technology organizations since 1999 and was the founder and CTO of Tripwire for 13 years. He is the author of six books, The Unicorn Project (2019), and co-author of the Shingo Publication Award winning Accelerate (2018), The DevOps Handbook (2016), and The Phoenix Project (2013). Since 2014, he has been the founder and organizer of DevOps Enterprise Summit, studying the technology transformations of large, complex organizations.

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