Construction Leadership Development Without a Playbook — with Lisa O'Brien

Construction's 3 Transformations at Once: Lisa O'Brien on Leading Without a Playbook

In this post: Construction leadership development has been underserved, and Procore's Lisa O'Brien explains why the industry now faces technology, business, and culture transformations at once. She shares three shifts that help veteran executives become the bridge to the next generation.

Lisa O'Brien set out to find the handful of levers that matter most to construction leaders. Her team defined 12 factors and expected three to six of them to rise to the top. All 12 came back equal.

"We're like, what do we do with that data?" O'Brien said on Activating Greatness, the leadership podcast from Velocity Advisory Group.

O'Brien, Director of Industry Culture at Procore, leads a team of culture strategists and coaches. Before joining the company about seven and a half years ago, she had worked in nearly every industry except construction. She expected construction leadership development to be "a copy and paste" of what she had seen everywhere else. The data proved her wrong, and it took months of conversations to understand why.

Construction Leadership Development Has Been Underserved

The first finding was about neglect. Construction, she concluded, has been underserved when it comes to human development, leadership development, organizational development, and culture development.

"The industry itself doesn't know what it doesn't know," she said. "It doesn't know what it needs."

It did not explain why every factor weighed the same.

The Caboose Meets the Fastest Train

The answer came from studying how industries change. Construction has lagged other industries for decades, she said. "It's the caboose at the end of the train." Now it is trying to digitize at a moment when technological change is moving faster than ever.

Industries usually transform over 15 years or more, O'Brien said, and the stages arrive in order. A new technology gets adopted and integrated, a process that normally takes three to five years. Business processes then change to match it, another three to five years. The final stage is culture and people: the new talent those technology and business changes attract.

Construction skipped the queue. "Construction is going through industrial transformation with all three stages at once," she said. She calls it complex nested change, with technological, business, and culture transformations running in parallel.

That is why no single lever emerged from the data. "It's all the levers at once, and there's no playbook," she said. "There are no role models."

Host Alec McChesney added the pressures stacked on top: the pandemic, and a workforce spanning 23-year-olds to 60-year-olds who want very different things from their employers.

Relief, Then a Fork in the Road

When O'Brien walks construction executives through the framework, the first reaction is physical. "There's a dropping of the shoulders, there's an exhale," she said. Leaders finally hear words for an experience they could not name.

After the relief, she sees two paths. Many of these executives are in the final years of their careers, with perhaps three to five years left in the industry. Some decide the transformation is not theirs to lead. "Can I just keep the status quo for now until my three to five years are up?" is how she described their thinking. She sees burnout turning into resignation among the people who hold the industry's institutional knowledge.

The others lean in. "What are we going to do about this?" they ask.

O'Brien has advice for both groups. Executives who are exhausted can take on advisory roles and bring their knowledge to the industry in a different way. Those who want to stay in the fight should "figure out how you can be the best bridge you can be for the industry and for those coming behind you," she said.

The stakes are high. Construction has long struggled with retention and succession, McChesney noted, and a middle generation that never received leadership development tends to keep the style it grew up with.

"They're no longer building buildings, they need to be building businesses that attract people."

Lisa O'Brien, Director of Industry Culture, Procore

Three Shifts for the Leader Who Wants to Be the Bridge

O'Brien starts with a strength. Veteran construction executives, she said, are "the best problem solvers on planet Earth." The gap is applying that same brilliance where humans are involved.

For an executive over 50 who wants to be the bridge, she recommends three shifts, each demanding a significant change in mindset and behavior:

• Listen: Go to your job sites and talk to laborers, employees, trade partners, and owners. "Actively listen without the desire to solve," she said. Listen to learn again.
• Learn: Your body of knowledge comes from the past. Listening shows you the present. Figure out what you need to learn to lead into the future you can already see.
• Mentor: Take what you have heard and learned, and "start to mentor every young leader in your organization."

Behind the shifts sits a larger claim. The construction executive's job used to be knowing buildings, holding technical knowledge, and running projects. As AI and other technology accelerate, O'Brien expects much of that body of knowledge to be taken over within three to five years. The executive's problem solving belongs on the organization, the culture, and leadership development.

"They're no longer building buildings, they need to be building businesses that attract people," she said. "Those people will be building the buildings, but they're building people."

Her rapid-fire answers pointed the same direction. The most underrated leadership skill, she said, is listening with curiosity, "not listening to know, not listening to solve." The habit great leaders should drop is needing to be the expert with every answer. "I think they should stop trying to know," she said.

Building a Better World and Better People

What has to change for people to line up for construction careers? Mindsets, O'Brien said. Legacy mindsets, reinforced by contracts and legislation, persist for reasons that no longer exist. They drive behaviors she described as adversarial, aggressive, and non-inclusive, and they push away a younger generation that wants meaningful work and wants "to be respected and developed at the same time."

The fix is to pair the industry's greatest magic, "literally building a better world," with building better people. The companies doing it, she said, "are growing like crazy." They attract talent from outside construction and bring more diversity of thought to the table.

Other construction leaders on Activating Greatness have made a similar case. Jackie Fisher of Juneau Construction laid out the business case for culture, and Jesse Hernandez explained why trust and culture drive results.

She also sees an opening. As AI-driven layoffs spread through tech and other industries, construction needs tech-savvy workers. The caboose may be where displaced talent finds purpose.

Key Takeaways

1. Construction is changing on three fronts at once. Technology, business processes, and culture are transforming in parallel, so no single lever will fix the problem.
2. Naming the change brings relief. Executives who hear the framework often exhale for the first time. Clear language is the first step toward a plan.
3. Choose your role deliberately. Leaders near the end of their careers can serve as advisers or as bridges. Drifting toward the status quo serves neither the company nor the next generation.
4. Listen before you solve. Talk to laborers, trade partners, and owners with the goal of learning, then mentor every young leader around you.
5. Build people, not only buildings. As technology absorbs technical knowledge, the executive's value shifts to culture, the organization, and leadership development.

The Takeaway: Practice Succession Living

The best leadership advice O'Brien ever received came early in her career: Always be working yourself out of your current job. That meant asking who she was mentoring and teaching to do her work so she could move on to what was next. "There's not ever a need I've noticed for succession planning, because I do succession living as a leader," she said.

For an industry facing all three transformations at once, that mindset is the bridge. Nobody has a playbook for complex nested change. The leaders who listen, keep learning, and hand their knowledge to the people behind them will write one.

Listen to the Full Episode

Hear Lisa O'Brien's full conversation with host Alec McChesney on Activating Greatness. Find it on YouTube, or listen on Spotify and Apple Podcasts.