In this episode of "Grown, Not Born," we chat with CJ Daniel-Nield, co-founder of Planes, about his transition from Air Force pilot to tech innovator. CJ shares insights from his leadership journey, comparing military precision with startup agility and discussing the impact of technology on team management. Explore CJ's philosophy on fostering high-performing teams and his approach to navigating the challenges of modern leadership.

Sarah: Thanks for talking to us. Could you briefly describe what you do?

CJ: I'm one of three co-founders of a digital product studio called Planes. Before starting Planes, I worked in product management at a startup, and before that, I served in the Air Force in New Zealand. My current role involves helping new clients determine if they need our services and, if so, devising the best strategy to solve their customer's problems.

Sarah: I didn't realize you were in the Air Force.

CJ: Yes, they funded my university degree. At 17, I aspired to be a pilot. Flying is thrilling, especially in small planes. However, you quickly realize that the plane can fly itself better than you can, making you feel somewhat redundant. Shortly after take-off, the autopilot takes over for the rest of the flight. People are apprehensive about flying without human pilots despite the fact that 40% of crashes are due to human error. I think that the only reason that there are humans flying planes is because people are scared of robots, imagine hopping onto a commercial flight and being told that the robot flying is only responsible for a third of crashes.

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People are apprehensive about flying without human pilots despite the fact that 40% of crashes are due to human error. I think that the only reason that there are humans flying planes is because people are scared of robots, imagine hopping onto a commercial flight and being told that the robot flying is only responsible for a third of crashes.

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Sarah: Sounds almost like a UX problem.

CJ: Yeah, and probably a regulatory problem. Also probably to do with the pilot unions having a lot of power in the US. But, it's not a job where humans are really good. We’re better when there's an emergency. But now with machine learning, I'm sure robots are way better than humans would be. Robots don't panic.

Sarah: Fascinating. Could you share your early experiences as a manager?

CJ: My first significant management role was in the Air Force, which provided extensive leadership training. However, real-world management differed greatly, especially when dealing with personal issues of team members, such as divorces. It taught me the importance of empathy and support in the workplace.

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The Air Force provided extensive leadership training. However, real-world management differed greatly, especially when dealing with personal issues of team members.

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Sarah: How does managing in the military compare to the business world?

CJ: In the military, there's a baseline standard and structure, making management somewhat easier. The base level is developed by both training everyone the same way and the structures in place, some of which are hundreds of years old providing a level of expected performance and roles are defined. Unfortunately, this system doesn’t exist in the civilian sector.

Sarah: What's one significant lesson or mistake you've learned from as a manager?

CJ: Every single person is wired differently, with varied responses to stress and different needs for autonomy and support. Early in my career, I mistakenly assumed everyone preferred the same management style I did, with a high degree of autonomy and a lot of space. But when managing in startup land, I tried to manage every one with really limited guard rails, giving a desired outcome and general push on what we’re trying to do. I found out quickly that everyone is different, some people don’t ask for help when they need it, some people want detailed instruction, and some people want no instruction. Adapting to the employee’s needs in how to manage them is challenging. Also, without defined roles, managing tasks in startups can be challenging. Delegating tasks to people who need to figure out how to do things for the first time without enough support is doesn’t work. It’s important to make sure that you take the time to think about how things look from the employee's side. Otherwise, you end up burning people out as they get too nervous to operate.

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Every single person is wired differently, with varied responses to stress and different needs for autonomy and support. Early in my career, I mistakenly assumed everyone preferred the same management style I did.

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Sarah: How do you balance individual needs with the overall business needs?

CJ: I think when it comes to aligning those two things, the reality is that it doesn't make sense for everyone to work at the same place for a long time. There are two parts of life and they can diverge. It makes sense to be upfront and honest about it. So, I try to create safety within my team so that they can share all of their hopes and dreams regardless of how much they are aligned to Planes’ future. I really like this notion of a tour of duty that employees might have at a business; they are there to achieve a few things that the business wants to get done as well. There's a contract but there's also a relationship that doesn't have to be solely transactional. You get the most out of relationships when both parties understand what they're trying to achieve. I always tell people what we think the next 1,3, and 5 years look like with as much detail as I have. We don't hide anything really at Planes, we share everything. So if someone explains that their goal is to work in another startup, we try to help that happen by asking what do you need to learn here? Or, who can I introduce you to that's gonna help that happen? Do you want to work on one of our client projects? It’s part of our vision that people use Planes as a stepping stone for whatever bigger thing they can do in the future. The thing I took away from the military was this notion of functional leadership. It says that there are three aspects of being a leader; there's the individual, the team, and then there's the mission. You can't decide that one of those things is more important than the other.

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We don't hide anything really at Planes, we share everything. So if someone explains that their goal is to work in another startup, we try to help that happen by asking what do you need to learn here?

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Sarah: What tools or technologies have you found essential for managing your team?

CJ: We use Leapsome for performance management and Notion for its flexibility in managing various management tasks. Regular one-on-one meetings and goal-setting sessions are crucial, regardless of the tools used.

Sarah: Makes sense, is there a tool you wish existed for management?

CJ: Initially, I searched for a perfect tool but realized that managing people requires flexibility. Notion has been the most adaptable tool for me, accommodating the diverse needs of my team, but it means putting the work and time to make it work for you.

Sarah: Finally, what animal would you compare your management style to?

CJ: Ideally, an elephant for its consistency and memory. Realistically though, I'm more like a Golden Retriever puppy – enthusiastic and supportive, but easily distracted.

Sarah: This has been incredibly insightful, especially your perspective on the transition from military to civilian management. Thanks for your time, CJ!