AI Mistakes: Focused Resilience and a Specialization Bet with Daniel Lemire (4/4)

Nerd Journey: Career Advice for the Technology Professional

If you had something to share, what would you say, and how would you say it? Daniel Lemire asked himself the same question in the process of creating AI Mistakes. As it turns out, AI Mistakes isn’t just a platform for learning in public. It’s something Daniel must be doing. Want to know why?

After completing the vision board and gaining more perspective on the layoff event that would change his direction, Daniel knew where to begin. But it took time to translate what he had written on the post-it note about his needs in a role to a role at a specific company. Through intentional mindset shifts, feedback from others, and additional help from a mentor, Daniel chose to make a bet on generative AI.

Join us for episode 326 and the exciting conclusion of Daniel’s story. We’ll discuss how the specialized pre-sales role at ServiceNow really is a culmination of Daniel’s experience to this point and how he’s filling some of the sales and marketing gaps from back when he was an independent consultant.

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 1-3 of our discussion with Daniel, check out Episode 323, Episode 324, and Episode 325.

Topics – The Next Right Thing and the Genesis of AI Mistakes, Gaining AI Expertise, Mindset Shifts and Greater Clarity, A Role in Pre-Sales, Transition to Working for a Technology Vendor

3:14 – The Next Right Thing and the Genesis of AI Mistakes

• John wants to hear more about the genesis of AI Mistakes.
  • The timeline starts when Daniel found out that he was in the group of people being laid off.
  • “So, here I am…I think I’ve got things figured out. I’ve done really well. I think I’m going to get a really great appraisal for having taken care of business and done a good job, but actually, I got nothing…. Even now I still don’t know what anybody actually thought of my performance that year that I figured things out.” – Daniel Lemire, on not getting a performance review
  • Though Daniel’s role had been eliminated, he and others were asked to stay on at the company until sometime during the following year (required to get a severance).
  • Daniel recounts having to comfort his team about his departure. They had not learned to regulate themselves as Daniel had.
    • “You’re going to be fine. You know what you’re doing. We’re putting you into a position to be successful going forward. You don’t need me to be successful. You just need to know that you can do this, and you’re good at what you do…. It just means that my next thing isn’t here, and that’s ok. I would not have been capable of having that conversation even a year prior because I hadn’t done the work that I needed to do to understand.” – Daniel Lemire, on comforting his team when delivering the news of his role being eliminated
    • Daniel says this moment was a big confidence builder, and he feels he handled it very well with his team.
  • Many of Daniel’s colleagues who were also part of the layoff did not handle it well. They were very angry. He reminds us these kinds of events are very difficult to go through.
    • Having a severance package certainly helped provide Daniel time. Daniel mentioned his brother went through this kind of situation and did not receive a severance.
    • Years early, Daniel had planned to stay as long as the company would let him, believing if the company decided to end his employment that it would likely result in some type of severance. He and a number of colleagues decided to focus on doing a good job and to deal with job loss if and when it came rather than living in fear about it. Daniel cites this mindset shift as an important point in his maturity to prepare for when the layoff eventually impacted him.
  • “When I got the announcement that that road was going to end, that was like a golden ticket for me.” – Daniel Lemire
    • Daniel ended his consulting business in 2009 after signing an agreement to work at PepsiCo. He was going “all in.”
    • Once he knew his employment would be ending, Daniel continued to do great work until the very last day nearly 6 months later (something he’s very proud of).
  • This was the catalyst for starting AI Mistakes. Daniel filed the paperwork and started developing a plan. He had learned a lot over the years since his last stint as an independent consultant and wanted to be ready for a potential return to it.
    • “Sales and marketing is a thing that matters, and you’re going to have to do it. And I’m ready for this.” – Daniel Lemire
    • Daniel assessed his preparedness for the uncomfortable parts of consulting if he was to return to it after the layoff. It was at least an option.
    • “But the name AI Mistakes came out of the recognition that that is how we learn the best. Even at a very technical level…you have to learn doing it the wrong way to understand what the right way looks like…. That’s why you don’t become an architect the minute you step out of college. You haven’t had enough opportunity to make big enough mistakes…. Everybody’s made a big mistake. If you talk to anybody in operations, I guarantee you they have a sev 1 story.” Daniel Lemire
    • Daniel highlights some of his biggest growth moments being when he really broke something. During these times other people had to pitch in to help fix the problems. We want to foster work environments so people can make mistakes that are not career ending or that they cannot recover from.

9:20 – Gaining AI Expertise

• Was AI a focus for Daniel when he worked on the innovation team?
  • Daniel says there were several projects the greater innovation team worked on which were AI heavy.
  • The exposure to AI for Daniel began by observing other members of the team and learning about it in the background. Someone was building models to improve manufacturing, and Daniel was able to see the progress and the outcome of that work, which sparked an interest in AI.
  • “The difficulty for me was I couldn’t do any of that work. I just knew that that was the right thing to be doing…. Sometimes my role in innovation more often exactly opposite of what I had been doing previously in my career. Every job I’d had at PepsiCo was being the subject matter expert. I was the big brain. The moment I stepped into innovation, all of that basically went away. The only thing I was really good at that I brought to the team was helping with architecture and mapping out how the systems should interconnect and how we should prosecute the program of dealing with all of the things. I was no longer the expert that knew how to do the specific thing. I was working with the team to make that happen.” – Daniel Lemire
  • A colleague on the innovation team told Daniel about GPT-3 and how it was actually beginning to work. After this conversation, Daniel got an OpenAI account, but despite thinking it was interesting, he didn’t really know what to do with it.
    • At least initially, Daniel couldn’t find the value in this tool.
    • “That is the number one thing I took away from my time in innovation…. What is the value, and how do you succinctly articulate that? …It can be the best technology. You can have the smartest people. But, if they are not willing to put their money to it, it doesn’t matter.” – Daniel Lemire
    • Especially when communicating with executives, being unable to clearly articulate the value of something means it will not get funded.
  • When ChatGPT happened, Daniel recognized it was going somewhere and began spending his time using it.
  • While he initially did not know what to do with GPT-3, Daniel had used Stable Diffusion to generate images for some of the presentations he built during his time on the innovation team.
    • Daniel had originally bought a couple of desktop computers with NVIDIA graphics cards to mine Ethereum as part of his innovation work. He mentions researching cryptocurrency and blockchain (and specifically NFTs).
    • The best way Daniel knew to learn about these technologies was to build a lab at home.
    • Once there was no way to mine Ethereum any longer, Daniels’ lab environment was left idle. He decided to use it for Stable Diffusion and began to learn how the models worked.
    • “So, I quickly became very familiar with those AI things, and then everything just kind of fell into place…. I’ve learned enough in an enterprise environment that I can actually consult and help people understand what the next thing is that they need to do…. A colleague at work said to me, ‘you know a lot, and you’re not sharing enough.’” – Daniel Lemire
  • The feedback from his colleague is what prompted Daniel to start a YouTube channel for AI Mistakes. See also the YouTube Feed on the AI Mistakes Website.
    • “If I really do have something that’s useful to share, who am I going to share it with, and how am I going to do that?” – Daniel Lemire
    • For many years Daniel would watch YouTube videos in the evenings to keep up with technology trends. Since this helped him learn things, he could provide content for other people to learn in that format.
  • Daniel was also used to writing newsletters for innovation, and he began his own AI Mistakes newsletter. You can view the newsletter and subscribe to it here.
    • He also had the previous consulting experience to lean on.
    • When Daniel was thinking through what would come next for him, he felt AI Mistakes could be that paycheck. He decided to treat it seriously and focus on it.
    • “I went from one day going into the office at PepsiCo to the next day sitting here working the same amount of time building all of the things around AI Mistakes…. I get excited about something, and I get after it. And that’s what I did…. But, having done that vision board, I also knew that…I’ve gotta focus on all of the things. I can’t just be narrow on one thing. I’ve got to think about the bigger picture.” – Daniel Lemire
    • Daniel reiterates that he did take a trip with his wife at one point to celebrate their anniversary.

15:11 – Mindset Shifts and Greater Clarity

• Daniel feels the work for AI Mistakes (preparation, getting better at speaking, building more expertise, etc.) and the repetition put him in the position to be successful in his interviews at ServiceNow.
  • He knew what to say and how to say it in these discussions, which was backed by proof of work and expertise (his content). Having the public proof of work helped tremendously.
  • Daniel has been able to monetize his YouTube channel as well (something he is very proud of).
  • “It was the iteration and the feedback that I got from doing that that helped me get better and put me in a good position for the next thing, and the mindset things that I tackled in the process gave me the confidence I needed to go into that room and have that conversation on the interview…why I was the right guy for that next thing.” – Daniel Lemire
  • Daniel also mentioned some mindset shifts during all of this such as needing to be working on something even if he could not immediately show the payback on that effort.
    • Daniel needed to have confidence that he was doing the right work focused in the right area and that if he kept doing it good things would happen.
    • When the severance check ended, Daniel did not yet have the next thing figured out. That was a very stressful time. Not long after this, Daniel once again gave up and relied on his faith just as he did after learning a career as a pilot in the Air Force was out of the question. The act of giving up and the steps afterward shaped what happened next.
    • Shortly after giving up, Daniel applied for the role at ServiceNow.
  • John mentions the post-it note did not mention anything about making a living as an AI influencer and coach.
    • “I was looking for insights in many different places.” – Daniel Lemire
    • At the DFW Prayer Breakfast, someone introduced Daniel to a CIO who would end up mentoring him. After a brief phone conversation about mentorship, the CIO sent Daniel a list of questions he needed to answer before they could continue. The questions were to help Daniel determine what he wanted.
    • “To be fair, my needs were pretty ambiguous as it came to a role, and the questions that he was asking me were very much more focused on ‘what kind of role do you want from a career perspective…what job do you want?’ I couldn’t answer it. I didn’t have that answer.” – Daniel Lemire
    • Daniel tells us the job role didn’t matter compared to what the job would do to fulfill Daniel’s needs as a contributor to an organization. He had applied to jobs as an architect, a product manager, an engineer, a leader, and even some focused on DevOps. None of the interviews for these types of roles worked out.
    • After answering the questions the CIO / mentor proposed, Daniel clearly understood he was willing to make a bet on AI. It was a trend / area he believed to be bigger than cloud and mobile combined. A new role needed to be something with generative AI within the scope of things which were familiar to Daniel.
    • The questionnaire from his mentor also helped Daniel sort out the type of company where he wanted to work. Initially, Daniel did not think enterprise was where he needed to be, but it turns out after further reflection, Daniel’s skillset would provide more value to a large enterprise.
  • If Daniel had insisted on his future being an independent consultant, it might have been driven by ego.
    • “AI Mistakes is one of the things I must be doing. There is a very clear calling for me to do that. The calling for me in doing that though isn’t that’s where I need to be earning what helps me take care of my family. That doesn’t mean there’s not a future for that to be the case, but that’s not the reason for the existence.” – Daniel Lemire

20:38 – A Role in Pre-Sales

• In the last couple of years, Daniel has recognized his lack of deep sales and marketing experience. He is consistently learning new things in his role within the go-to-market organization inside ServiceNow. Daniel says he’s not putting a limit on the number of years he plans to stay in the role.
  • “It’s creating value. I love having the conversations. I feel like I’m really actually helping people… It is fulfilling the post-it note in ways that I could not have imagined…. I think the reason I needed that job was that I wasn’t going to get all of those things from just doing AI Mistakes. Or perhaps I couldn’t get to those things in the time that I needed that to be the case.” – Daniel Lemire, on his role with ServiceNow
• Daniel confirms his current role is a pre-sales role and that back when he knew things were going to change for him at PepsiCo, pre-sales wasn’t even on the consideration list for what might be next.
  • Daniel loves his current role working in pre-sales and mentions it contains so much of what he needed.
  • John thinks another role which could have fulfilled the post-it note for Daniel is technical marketing.
  • “The thing that I didn’t understand about sales from the very beginning was that it’s not about getting somebody to give you their money. That’s what we all think about when we think about sales, right? It’s transactional.” – Daniel Lemire
    • Daniel has read a lot about sales in the last 24-36 months, recognizing that even if AI Mistakes could make money, he would eventually need to make a sale.
    • “And that’s probably a big part of why I was able to get a role in pre-sales because I didn’t walk into that just being a technician. I walked into that with many volumes of sales learnings in my back pocket. And having done inside sales doing innovation at a corporation meant that I had many conversations trying to convince somebody to give me their money to go and do the innovation thing.” – Daniel Lemire
    • Nick says Daniel’s role as an architect even contained a sales element, especially when encouraging colleagues to adapt cloud and DevOps.
    • The role at ServiceNow was a good fit for Daniel because of the time investment he made.
    • “There’s no reason to buy the technology unless it solves a problem, and you have to get to the heart of the problem. What is the why? Why does this thing matter?” – Daniel Lemire
    • We need to be able to answer those why questions both for us and for other people.
    • John mentions taking a value selling course when he first got into pre-sales and the emphasis on understanding the buyer’s metrics for business success. After a decade in IT Operations, John had never once asked for his manager’s metrics for success.
    • Daniel said he never really had to do this until he was on the innovation team. As an architect, he usually had to convince technical people that something was the right answer, and it never really left the technical domain. Daniel recounts a professor from his graduate program saying, “we have an alignment problem. People that do technology don’t know how to explain to the businesspeople why the technology matters, and until you solve that problem, things are going to go sideways. It really is that simple.”
    • This alignment problem is the number 1 problem both technologists and businesspeople have to solve.
    • John says many people don’t know if they are working on something which makes their company money. It is often easier to keep your job when you work on something aligned with revenue as opposed to something viewed as a cost center. Within a cost center, there is always pressure for the cost to go down. When something is generating revenue, the discussions are more about return on investment.
    • Daniel says it took him reading The Phoenix Project to understand these things even after obtaining his graduate degree. It took the enterprise context as well.
    • All things considered, Daniel says he would not change a thing.

26:51 – Transition to Working for a Technology Vendor

• What other challenges does Daniel see based on his experience moving from being a technologist to working for a technology vendor?
  • Daniel says he needed to separate himself from needing to have a specific level or title and be willing to put himself in a different position.
  • Daniel is a higher-level individual contributor at ServiceNow in his pre-sales role, he has no direct reports. He works with sales executives and other solutions consultants to help customers.
  • “I had to have the experiences in being a manager and being in charge of the technical things and being the architect and driving the programs to be able to sit down with the people that are at our customers to help them negotiate the challenges that they’re in. But that has nothing to do with a title. That was something that I didn’t understand until I got into it. The reason I was able to get the role at ServiceNow…was because I wasn’t overshooting where I could add value.” – Daniel Lemire
  • John mentions often times an entry level pre-sales position is a mid-career position. There are more junior versions of this role to allow entry for people earlier in their career. In order to generate value in a pre-sales role, it takes many different types of experience and skills.
  • Overall, Daniel doesn’t think he is missing any of the other challenges of stepping into the role. He gives credit to the team who interviewed and hired him and recognized he could do well in this role.
  • In his current role, Daniel works with many different sales teams as a technical overlay / specialist. He is not dedicated to a specific set of customers but rather is a dedicated resource to internal sales teams for supporting their customers.
    • Daniel shares a recent story of getting some very positive feedback on a customer presentation from the account team he was supporting and stresses the importance of feedback for his own improvement.
    • “I tell the account team…‘when we’re done, I want your feedback. If it’s bad or good I need to know because I’m going to touch a lot of other customers, and if there’s something I can improve, I need to get to work now.’” – Daniel Lemire
    • Daniel is very mindful of trying to balance being confident with preventing himself from being too confident.
    • Nick re-iterates what Daniel told us earlier in our discussions – “in the absence of feedback, you can be open to experimentation.”
    • John likes to label his performance in situations as performing well or performing poorly. Doing well or doing poorly does not make a person good or bad.
  • Daniel didn’t expect this but views himself as a performer. It’s about how he can serve others in the moment. Nick says it’s the value he can deliver.
• If you want to follow up with Daniel on this conversation, you can:
  • Contact Daniel on LinkedIn
  • Learn about his work with AI Mistakes, including his YouTube Channel

Mentioned in the Outro

• Daniel needed additional clarity from a mentor to gain the clarity necessary to translate what he had written on the post-it note to a role at a specific company.
• If you or someone you know has been impacted by a layoff event, 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.
• Daniel’s statement of “you don’t need me to be successful” and the need to comfort his team about his departure reminds us of Marni Coffey’s story. Go listen to Episode 280 – Life after Layoff: A Leader’s Sense of Duty and A Series of Good Conversations with Marni Coffey (3/3) to hear the parallels.
• Daniel made a bet on generative AI. When we make a bet on a technology, we want something with longevity in the market that needs the attention of our skillsets. We want it to still be relevant by the time we have enough expertise in the area to get a new job, for example. Compare the way Daniel decided to that of Brad Christian in Episode 264 – Back to Basics: Technology Bets and Industry Relationships with Brad Christian (2/2). Both are valid sets of reasoning.

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