How to Become a Leader in Digital Engineering with Devon Middleditch

Construction has a habit of promoting its strongest technical people into leadership and then watching them struggle. The skills that earned the promotion, deep tool knowledge, clean code, precise models, are not the skills the new role demands. Many try to do both jobs at once and end up doing everything poorly.

Devon has lived that transition across AECOM, KBR and Transport for New South Wales and his lessons are unusually candid.

When you are promoted into leadership, the organisation is asking you to change. The sooner you leave the old job behind, the sooner you become effective.

Get off the tools, deliberately

The pull of the technical safe space is strong. Devon describes reaching a breaking point where he was juggling CAD management, code, and people leadership simultaneously, and being ineffective at all of it.

What tends to work is a forced experiment. He once asked a talented deputy who kept drifting back to design work to spend a full month without opening his design tool of choice, focusing only on people and operations. At the end of the month, the deputy wanted to go further. His career has climbed through stronger leadership roles ever since.

Organisations expect you to do one role really well, not two roles adequately. Structure your calendar so the old role cannot creep back in.

Culture is measured under pressure, not in surveys

Annual engagement surveys try to capture something soft and analog through a tick-box exercise, and they mostly fail. The real signal lives elsewhere: water cooler conversations, coffee chats, and above all how people behave when a project is under stress.

Teams that stay calm under pressure, and rally around whoever is carrying the load, are telling you the culture is healthy. Consistency from the leader matters more than style.

If you want to know what your culture really is, watch how your team treats each other in the hardest week of the project, not what they write in the annual survey.

Scale with a 70-30 core

Rapid growth is where cultures quietly die. Devon’s rule of thumb is to keep roughly 70 percent of a team as full-time employees and no more than 30 percent as contingent workforce. Flip that ratio and the culture erodes.

Just as important: treat contractors exactly like employees. He has seen environments turn toxic when hourly-rate staff were isolated and treated as a different class, and the whole team’s performance suffered for it.

A stable full-time core carries the culture. Contractors extend capacity, but only if they are brought inside the team rather than kept at its edge.

You cannot tell people digital, you have to show them

Innovation communicated through slide decks rarely lands. At Transport for New South Wales, Devon’s group replaced death by PowerPoint with a physical Innovation Hub: simulators, AR and VR, drones, robotics, and 3D metal printing that project teams could touch.

The outcome was not just awareness. Teams walked in with delivery problems and walked out proposing co-developed solutions. Even finance teams started to understand what a budget line item actually bought.

Demonstration converts sceptics faster than description. If you want investment in digital, build an experience, not a presentation.

Critical thinking is the next core skill

An engineer using machine learning and AI agents will be a far stronger engineer than one who does not. But as more results arrive machine-generated, the differentiator becomes the ability to look at an answer and sense that it does not smell right, then trace how it was calculated.

Earlier generations built that instinct by working from first principles. The next generation will have to build it deliberately.

The more work machines produce, the more valuable the human who knows when to distrust the output.

Practical Takeaways

• When promoted, name what you are leaving behind and stop doing it. Do not attempt both roles.
• Trial the transition: take four weeks fully off the tools before deciding it is not for you.
• Invest in self-awareness training such as understanding and managing self and others, early in your career.
• Keep your team at roughly 70 percent full-time employees when scaling quickly.
• Onboard contractors exactly as you onboard employees, with no separate treatment.
• Lead innovators with space and big-picture goals, not utilisation targets and tight controls.
• Judge culture by behaviour under project pressure, not by survey scores.

The industry’s pipeline problem is not a shortage of technical talent. It is that we keep asking that talent to become something different without telling them what the new job actually is. The leaders who make the jump are the ones who accept that leaving something behind is the price of moving forward.