Overwhelmed by Ambiguity: DevOps, Innovation, and the Search for Clarity with Daniel Lemire (3/4)

Nerd Journey: Career Advice for the Technology Professional

What happens when there is too much change at once after making a job change? Daniel Lemire had learned the principles of DevOps and combined it with his experience as an infrastructure architect to advocate for the adoption of new technologies and processes within a large enterprise. But when Daniel changed roles to focus on innovation and became a senior manager at the same time, there were many challenges for which he was unprepared. In fact, at times it was overwhelming.

In the 3rd installment of Daniel Lemire’s story in episode 325, you’ll hear Daniel’s reasons for focusing on innovation in the first place, why he continued to persevere through challenges, the stress and impact of layoff events, and the unexpected way he found clarity amidst the ambiguity.

Original Recording Date: 03-20-2025

Daniel Lemire is an AI Consultant working for ServiceNow. He’s also the creator of AI Mistakes. If you missed parts 1 or 2 of our discussion with Daniel, check out Episode 323 and Episode 324

Topics – A Personal DevOps Value Story, Planting Seeds of Innovation, The Challenges of Impactful Innovation, Progressing from Overwhelm to Clarity

3:33 – A Personal DevOps Value Story

• Daniel needed a reset and to determine how he could contribute to the organization where he worked. That’s about the time he discovered DevOps.
  • After a recommendation from a colleague within the security organization, Daniel read The Phoenix Project, and it has changed his career trajectory for the better. He read the book not long after its release.
  • Reading the book also changed the way Daniel thinks so he is able to help companies create value.
  • “…When I read it, I didn’t understand what was so great about it. I just knew there was something there that I needed…. I read it and I got really excited about it. But I didn’t really know what to do with it.” – Daniel Lemire
  • Not long after reading The Phoenix Project, Daniel recommended the book to a colleague who worked on the security and compliance team. There was a character in the book named John who starts off being very stressed but for whom things improve greatly during the course of the story.
    • “After he finished the book, he came back to me and he’s like, ‘let’s do something with this….’ I still didn’t know what to do with it.” – Daniel Lemire
    • Daniel’s colleague recommended they start by meeting and having a conversation.
    • After their initial meeting, Daniel and his colleague started meeting on a weekly basis. They started talking about The Three Ways and how these could be applied to make things better. Daniel and his colleague gave a presentation to a large portion of the IT Operations team to share thoughts on the way people do work and how to improve it.
    • “It really helped them think through some of their organizational challenges and the things that needed to be done because that was also a difficult time across our technology organization because of the big changes that were being made. But the lightbulb didn’t really all the way come on for me until The DevOps Handbook came out and I got the concrete ‘these are the things that matter to a technology organization.’ So much of what I think about from a technology manager perspective has literally come out of that story. It is The Phoenix Project helping me related to what was going on and then the handbook giving me the tools to do the things that mattered that have enabled me to grow my technical accumen into an organizational behavior mechanism…. Ultimately if you can’t apply the lever in the right place, it doesn’t matter…. You can have the best people. You can have the best technology. But if you don’t solve the right problem, you’ve done nothing. That is a contextualization on many different levels.” – Daniel Lemire
  • Daniel cites The Goal by Eliyahu Goldratt as another very influential book. He says it helps you understand systems at a bigger level and would recommend it to any technologist, referencing the drum buffer rope concept.
    • We must be able to do the right things within the right context to create value.
    • Daniel achieved continued success applying the principles of DevOps which allowed him to continue into a management role at PepsiCo.
• Before Daniel was a manager, he needed to work with and influence people to do technical work across the organization. These people didn’t necessarily work with him on a daily basis or have a rapport with him. Learnings from his study of DevOps came together in a meaningful and useful way in these situations.
  • Daniel cites understanding the metrics needed to get the kind of feedback you need as an example.
  • Reflecting back on it, Daniel was excited about what The DevOps Handbook promised. The book’s introduction was telling a value story for the application of DevOps, including examples of organizations that had used the principles of DevOps to increase performance.
  • “You needed everything that was in the rest of the book, but what got me excited was what those things could do. Understanding that promise of improving the system got me thinking more about how to build an effective system.” – Daniel Lemire, describing the introduction of The DevOps Handbook as a value story for DevOps

9:26 – Planting Seeds of Innovation

• Daniel was already helping colleagues understand how to make effective technical contributions to building systems. The principles Daniel learned from The Phoenix Project, The Goal, and The DevOps Handbook allowed him to push these conversations beyond just the technical – into the business domain.
  • “You’re never going to be successful in architecture if you’re not able to encapsulate the business domain.” – Daniel Lemire
  • It’s important to be able to explain why we do technical things.
  • “Architects, in my view, are really masters of making tradeoff equations. In the infrastructure space, you can install a single server to do something, and you can get that system in place very quickly. But it’s fragile because if any individual component failure comes into play, you can’t do anything. So, you have to build these failure domains that allow you to maintain the integrity of the system, but that’s more expensive…. When I think about what I learned from DevOps, it is balancing those two equations.” – Daniel Lemire
  • Daniel distinctly remembers a chart having to do with the number of developers working on a given project. It’s the Mythical Man Month concept. He gives the example of a baby’s development. It takes 9 months. This is a known limitation of the system.
    • Daniel says architects understand technical limitations in specific areas but also overall system limitations. The limitations are used to make the right decisions in conjunction with the requirements to meet the business need so the overall program can be successful.
    • “The better you are at putting those pieces together, the more successful you’re going to be in solving the problems that the organization at large has.” – Daniel Lemire
  • According to Daniel, an architect doesn’t just put technical systems together and stop there because it can limit one’s success. Daniel mentions receiving guidance from people in the DevOps community to extend his skills beyond the technical.
  • While learning DevOps did afford Daniel the opportunity to do some interesting work as an infrastructure architect, but he eventually reached the point of needing to do something different.
  • Daniel remembers completing a specific exercise for his personal development plan focused on the kinds of things he wanted to do in his career. Daniel wrote down his desire to be an architect and focus on innovation.
  • Daniel was a competent infrastructure architect who understood the challenges of the role very well. He experienced successes driving new technologies like DevOps and adoption of cloud technologies and was extremely proud of those efforts. The next architectural project for Daniel was building a very critical business system in the cloud. It was interesting but not interesting enough.
    • “I knew exactly where I was headed with that program. I thought it was interesting, but I also thought it was boring. And that’s not what I wanted to do next…. I saw the pain that was coming for me by doing this next big thing. I wasn’t excited about it, and I just couldn’t put myself in that position going forward.” – Daniel Lemire
    • Daniel mentioned many corporations across the world have a lot of work to do when it comes to cloud technologies. We are great at adding new technologies but not so got at getting rid of the old ones. The Phoenix Project describes problems and challenges that are applicable to many companies. We can learn from other companies without having to go through the pain.

15:07 – The Challenges of Impactful Innovation

• “And, oddly enough, an opportunity opened up for me to get to that next level and be a senior manager and go do innovation. Man, I was so excited about that.” – Daniel Lemire
• Reflecting on it, Daniel was very good at introducing critical new things within the company. He points to the beginning of cloud dialogues with colleagues and how their reactions changed from initial confusion and detraction to full support within a couple of years.
  • “I was one of the guys that said, ‘yeah, we need to go do this.’ I don’t think I was wrong, and DevOps was the same way. Some people were like, ‘I don’t know why this is your thing.’” – Daniel Lemire
  • Daniel mentions conversation he had with a mentor who disagreed about DevOps being what the organization needed to solve certain problems. At the time, Daniel knew he would not win that battle.
    • “The challenge I always had with him was – he’d throw me off my game. He’d ask a really intelligent question that I had no way to answer. I liked that about him because every time I got in a conversation with him, he’d point out something I hadn’t thought about…. Any time I showed up with something like, ‘hey, we need to do this’ he would throw a curve ball at me that it would take me weeks to solve or in some cases months…. He wasn’t wrong…it just turned into this wall for me. Even now, looking back on it, I know that I was fundamentally right in saying this is what we need…. You can take the right next step and not be able to explain why it’s the right next step in the moment, but it’s still the right next step.” – Daniel Lemire, on overcoming challenges when presenting new ideas
    • Trying to answer the questions his mentor asked might keep Daniel from getting things accomplished because he was determined to fill the gaps in his knowledge.
  • John has empathy when it comes to the constant question of changing systems.
    • “At least I know the problems of the system that I know, and new systems bring new problems.” – John White, paraphrasing The Systems Bible
    • John highlights the difficulty involved in knowing whether someone is bringing up an 80% objection or a 20% objection. We generally manage to the 80% because managing to the 20% can cause different issues. See also The Pareto Principle or 80/20 Rule.
    • Daniel has emphasized this theme more often lately in his consulting role. Many of the objections people raise are part of the 20%. Looking back, he is not sure if the objections his mentor raised would fall into the 20%, but we as technologists today spend way too much time on the 20%.
    • John says a lot of time will be spent on the 20% regardless of the efficiency of the 80%. Optimizing the 80% provides more time for the 20%.
• “I was just really tired of dealing with the 20% all the time, and I really wanted to be able to do a lot of things…. There’s the 80% of the problems that you can solve very, very quickly, and then there’s the 20% of the problems that you just have to spend a ton of time to get there.” The same is true with expertise, right? You can be 80% effective at a brand-new thing in a short period of time, but to get that last 20% it takes much, much iteration. Having spent a decade in infrastructure, I became far too focused on the little bitty things." – Daniel Lemire
  • When he worked in infrastructure, some of the projects Daniel worked on were measured in years. In infrastructure, one cannot take risks. It’s important to put in a reliable system.
  • Daniel needed something different. The opportunity to move into innovation solved this problem. It allowed for fast iteration on things. Daniel tells us he did more projects in innovation than his entire career in infrastructure because of the nature of the beast.
• Was getting to work on many different projects in innovation something Daniel considered to be a bigger impact?
  • Daniel says no.
  • “So much of the things that I worked on in innovation became shelfware. You can drive a lot of excitement about something new, and you can run an effective proof of concept and show that something is valuable or not valuable. But it doesn’t mean that somebody’s going to stand up and say, ‘I’m ready to go try this,’ especially in an enterprise environment because even ROI often times is not enough to satisfy the ‘why are we doing this?’” – Daniel Lemire
  • Daniel would not say it’s impossible to inject innovations into an enterprise successfully, but he highlights a number of challenges from experience.
• When Daniel began the work in innovation, he didn’t actually know what it took to do the work of innovation at an enterprise level.
  • It took Daniel years to make progress on cloud and DevOps within the organization.
    • This effort requires addressing multiple dimensions – educating others, building technical accumen, governance, politics, governance, the organization in which you’re operating, and the monetary aspect of it.
    • These are also true for innovation.
  • “What I didn’t understand when I started the journey was that I was signing up to do those things in a much shorter period of time than I was really prepared to do. I knew what to do. I had not done enough repetition to be very effective at it. Now the good news is because I was in innovation the repetition happened a lot faster, but it didn’t make my boss happy that I wasn’t very good at it….” – Daniel Lemire
  • What does not very good mean?
    • Daniel says he did not understand the practice of innovation well enough. It requires doing some very specific things, and upon taking on the role, he was ignorant of those things. Daniel did a lot of reading to get up to speed on these items.
    • Daniel refers to a conversation with Jensen Huang and a journalist about Starting NVIDIA. If Jensen had known what he was signing up for when deciding to start NVIDIA, he probably would not have done it. Daniel says this parallels his experience in innovation – not understanding or appreciating what he had signed up to do.
• There were some challenges to taking the role in innovation that Daniel needs to share with us. Daniel knew some members of the innovation team and felt he would have fewer interpersonal challenges. He was ready to tackle something new, excited about this opportunity, and understood it would be a difficult task.
  • “I’m aggressively going after jumping into the deep end because consistently…if I throw myself into the deep end, I’m going to swim.” – Daniel Lemire
  • Daniel accepted the role of senior manager of the innovation team in February 2020 right before the global pandemic really started in the US. He was not prepared for it.
    • In some ways Daniel feels like it may have been a mistake, but in other ways he doesn’t have any regrets about taking the role.
    • “In fact, I can remember very clearly the conversation I had with my manager in completing in completing my objectives review going into my 4th year in innovation…. My manager says to me, ‘Daniel, you’re not good at this.’” – Daniel Lemire
    • Though it was a tremendous challenge to meet his manager’s expectations, Daniel understood his future success hinged on getting good at the different elements required to perform the role well.
  • Daniel’s manager eventually took on a different role within the organization. It was challenging for Daniel to have his manager leave knowing he had disappointed his manager with his performance.
  • “It was basically the next month that things started to click for me. He wasn’t wrong in that I wasn’t performing well for the things he needed me to do well at. It was almost in the next breath that things really locked in, and it all started to make sense for me…. I’m also not going to tell you that I immediately went from being not great at this thing to being the best there is….” – Daniel Lemire
  • Daniel says things start to make sense after a certain amount of iteration and feedback just like some children need to fall down many times before learning to walk.
    • Nick gives the example of James Dyson’s relentless drive to iterate and get to a working prototype. See also Invention: A Life by James Dyson.
    • Maybe Daniel’s manager leaving forced him to step up and do better? Daniel isn’t sure what made the difference, but he knows it was what he needed and has been a major contributor to the work Daniel has done subsequent to the position in innovation.

27:27 – Progressing from Overwhelm to Clarity

• Was the point at which everything started to make sense close to the time of Daniel’s exit from PepsiCo?
  • When Daniel had the tough career conversation with his manager about his performance, he knew he was close to turning a corner. Daniel didn’t plan to seek out a new role just yet.
    • This scenario destroyed Daniel’s confidence. He didn’t fully realize how much of a problem this was at the time.
    • When Daniel’s boss left and he asked about applying for the director position, Daniel said he did not want it.
    • “Somebody had just told me I wasn’t good at doing those things. Why on earth would I sign up for more responsibility when I’m not good at the things I’m already responsible for?” – Daniel Lemire
    • Looking back, Daniel thinks he should have signed up for the director role, feeling he was capable of doing the job.
    • The team had no director for a period of time once Daniel’s manager left. Daniel encouraged one of his very capable peers to take on the director role and had no issues working for a different manager in lieu of removing himself from the director role candidate pool.
    • During this period, Daniel continued to improve his skills as an innovation manager, filling some of those earlier gaps he had.
  • “Right about the time I’m feeling pretty good about where I am and how I’m seeing things and being able to classify and organize and execute the things that I think need to be done…the earthquake happens.” – Daniel Lemire, describing a pending layoff event
    • Daniel could clearly see what was happening over time from his learnings getting the graduate degree. He and his peers in the infrastructure space knew there was a larger organizational plan happening. The only real opportunities in the infrastructure space within the company were if you intended to become a director, senior director, or vice president.
    • "All of us at one point several years ago kind of looked at each other and said, “are you going to hang around until the end, or are you going to jump and go somewhere else?’ I’m a really loyal guy. That’s just part of who I am. It’s really hard for me to pick up and leave because I’m invested. That was what was in play for me. I was just really invested in being a part of the organization….” – Daniel Lemire
    • Daniel remembers getting the opportunity to move into the innovation group. He was moving into a different area and did not feel he would have an “end-of-the-road” problem like in the infrastructure space. It could potentially be the next 10 years of his career.
    • “One of the things I also knew moving into innovation was our innovation team directly reported to the CTO, and the reality of that relationship is if you aren’t satisfying the objectives that the CTO has, you don’t have a reason for existence. So, you have to be very good at delivering on what you’re promising. The stark reality was that as a team, holistically we weren’t delivering to all of the objectives that the CTO had. So, something had to give, and in this case, it was me. I was the one that got cut from the team.” – Daniel Lemire
    • Many were surprised that Daniel was impacted by the layoffs. Daniel doesn’t think performance ratings played into this but isn’t sure. Reflecting back on it, the role in innovation had too much ambiguity for Daniel while he was doing something very different. The time period in which all this happened also made this difficult.
    • “It was too much at once, and it took me years to figure out how to navigate that well and to get back on the horse well.” – Daniel Lemire, thinking about his role in innovation.
• There are some good things that happened during this progression leading up to the layoff event that Daniel wanted to share with us.
  • A couple of years before Daniel was laid off (and before he moved to the innovation team), one specific round of layoffs of his colleagues created an extraordinary amount of stress on Daniel, and that stress made him sick with gastrointestinal issues. Daniel’s direct boss was impacted at the time, which made it very difficult.
  • “But I learned a lot from that situation because I had not learned how to regulate my emotions attached to what was going on. I was so invested in my reputation and my title. That was what was really important to me, and I didn’t understand that I needed to focus on everything about what I was doing, not just my career…. I needed that recalibration, and I also needed to focus on my health a little bit more.” – Daniel Lemire
  • Joining the innovation team took away the immediate stress. Even though Daniel wasn’t performing as well as he needed to within innovation, it did not come with the same amount of stress as when he worked in infrastructure, and it was an entirely new set of challenges.
  • Daniel was able to recalibrate what it meant to be in a future round of people leaving the organization.
  • “I was able to contextualize what that meant and recognize that that really didn’t have anything to do with me and that sometimes these thigns happen and that I just needed to get myself in order. No matter what was going to happen, that was on me to do, and nobody else could take responsibility for that. So, in some ways it was accepting that responsibility of ‘I need to be in charge of the whole me.’” – Daniel Lemire
  • Daniel mentions that his wife made a decision to go and get some coaching to improve herself, and it impacted him in a very positive way. Daniel was in a bad place, and his wife shared some of the learnings from that coaching with him.
    • At one point Daniel’s wife encouraged him to make a vision board that covered all areas of his life. This was close to the time Daniel had the difficult conversation with his manager in innovation. Daniel’s wife had already made one for herself, and it was extremely helpful.
    • “I’ve gotta tell you guys, there’s something much bigger at play because it was almost the next moment after finishing that vision board that things started to happen…. I honestly believe that if I hadn’t done the vision board that none of those things would have happened. I really think that was the trigger. It was me getting clarity on what mattered.” – Daniel Lemire
    • As a result of making the vision board, Daniel had the overwhelming need to get a LinkedIn subscription and to share content with people. Daniel refers to the things that happened next as “a snowball of change.”
    • “I need to be in a position that I can uniquely fill, to use all of my skills and not just be managing tasks, to apply technical experiences to make the organization better, and to build systems that help people and have my contribution valued.” – Daniel Lemire, sharing what he had written on a post-it note after completing the vision board exercise
  • Daniel says it was completing the vision board and getting the clarity that launched him into a “next phase.” For the first time in several years, he knew what he wanted. At one point he had been merely going through the motions so he could recover from the overwhelm of too much ambiguity.
    • While still on the innovation team, Daniel was starting to think about the type of role he wanted next.
    • “If I had the permission to do something or anything, what would that be? One of the things that I outlined for me was doing things that were outside of my specific role because that was part of how I had been successful in my past, and I knew I needed to get back to that.” – Daniel Lemire
  • John pointed out that nothing on Daniel’s post-it note said he needed to be working in innovation or that he needed to be a senior manager. It was much more general. When we cut it down to the core, for Daniel, it wasn’t about the title or the area he was working in. Daniel says he needed to get clarity about what was important first before his “what’s next” could begin.
    • Nick remembers having lunch with Daniel around the time of the layoff that impacted Daniel and hearing his idea. Daniel’s idea and proposed direction seemed extremely clear based on the time at which the lunch occurred.
    • Daniel says Nick observed the output of Daniel getting the clarity he needed. Daniel also tells us he did not appreciate the importance of getting this clarity and at some point along the way had stopped seeking clarity.
    • "…There’s no reason that you have to abdicate your responsibility to understand what it is that you should be working on. We should all be working on something at every moment, and we should be intentional about the things that we’re working on. I let go of my initiative because of the ambiguity. I didn’t have a rudder, and I wasn’t doing the things that I needed to do to get that rudder back. And I take responsibility for that. I really do. I think I could have done a better job of navigating that situation if I had thought about what I needed to prioritize and thought about what it was that I needed to be doing. And I also needed that…because it got me asking…‘ok, that’s all done. Now what?’ I can’t go back and change any of that. It doesn’t matter. What am I going to do now? " – Daniel Lemire
    • Daniel refers to the scene in Frozen 2 where Anna sings about “the next right thing.”
    • “It’s reflecting on those ideas and those thoughts that was also the genesis of how I wound up falling into this AI Mistakes thing that I started.” – Daniel Lemire

Mentioned in the Outro

• This was another story of someone impacted by a layoff event. If that’s you or someone you know, check out our Layoff Resources Page for access to the most impactful discussions on the topic of layoffs with industry experts and technologists like you.
• The clarity Daniel gained allowed him to reframe the layoff event, and in seeking the clarity, he figured out what he wanted and needed in a job role.
  • It was the vision board and going through that exercise that made the difference. Nick suspects there is some parallel or possible overlap in the vision board and the Must Have List that Kat Troyer and Liz Bronson (the hosts of RealJobTalk) shared with us a while back.
  • We usually don’t take the time to perform these types of exercises because we’re overwhelmed or have too much work to do or get distracted by other things. Maybe you need to spend time seeking clarity.
• When Daniel mentioned he wasn’t sure what to do with DevOps after learning about it, Nick thought this sounded like more missing context. It reminded him of the mix of concrete and abstract learning that Erik Gross spoke to us about in Episode 267 – A Theme of Learning with Erik Gross (1/3).
• Daniel’s ‘what now’ question reminded Nick of what Cody de Arkland shared in Episode 86 – Emotional Tech Support and Debugging with Verbose Logging with Cody de Arkland – stating lives and careers are like seasons. It’s more about when is next than what is next.
• Daniel also shared some book recommendations after this recording that we will mention (both available in audio form):
  • What to Do Next: Taking Your Best Step When Life Is Uncertain by Jeff Henderson
  • Imaginable: How to See the Future Coming and Feel Ready for Anything―Even Things That Seem Impossible Today by Jane McGonigal
• What did Daniel mean by starting AI Mistakes at the end of that episode? We’ll share the story next week as we conclude with part 4?

Contact the Hosts

• The hosts of Nerd Journey are John White and Nick Korte.
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• If you’ve been impacted by a layoff or need advice, check out our Layoff Resources Page.