Last year, Forbes published an article examining five common fears preventing people from switching career paths, whether within or outside their industry. The list begins with the fear of failure and ends with the fear of uncertainty: “We worry so much about feeling humiliated or disappointing others that we give up on attempting to achieve our dream. The problem with fear of failure is that it can be paralyzing, causing us to do nothing.”

To embrace that paralyzing fear of the unknown and chase your dream, or to play it safe on your current career path? That is the question Lili Fang, who was promoted to senior superintendent last year, found herself grappling with as a project manager (PM) on The Avery and 706 Mission in the years leading up to 2021.

“I was enjoying being out in the field more and more,” she shares. “I went to all the 6 a.m. superintendent meetings and walked the site at least once a day, even as a project manager, and realized those were my favorite parts of the day. Those were the times I felt the most connected with my project and my job. I finally asked myself, do I keep doing what I know I’m good at, or do I start doing what I like? Once I was honest with myself, I knew I had to make a change.”

Jumping head-first into field leadership with minimal field experience meant mistakes and previously undiscovered levels of self-doubt were inevitable—a drastic redirection from her seven years of seamless growth on Webcor’s project management track. At that point, Lili had consistently surpassed expectations and delivered exceptionally high-quality work, first as a project engineer (PE) hired by CEO/President Matt Rossie on SFMOMA, then as an assistant project manager (APM) and eventually PM on The Avery and 706 Mission.

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Despite her clear affinity for project management work and glowing performance reviews from managers and peers, however, she knew she wanted something different. She wanted to build.

Instead of accepting her impending promotion to senior project manager, she boldly decided to dive into the field world and transition to the construction management track in 2021. Today, she is the senior superintendent leading the Buildings 913 and 921 scopes and expansive site utilities scope of work at the Biosolids Digester Facilities Project (BDFP)—arguably Webcor’s most complex, demanding, and community-centric project.

She’s come a long way since joining Webcor nearly a decade ago. Just ask Matt.

“When I interviewed Lili, it was clear that she was technically savvy and excited about building,” he says. “She was outstanding as a PE and PM, but her passion lies in the field. As a superintendent, she embodies the enthusiasm and good nature needed to keep her team and the subcontractors with whom she works together while still having the grit to stand up to them. Heaven help the tradesman who makes the mistake of underestimating her!” (You can hear everything Matt has to share about hiring Lili about 18 minutes into this episode of Webcor’s 50^th anniversary podcast, when he was asked about his best hire.)

Transitioning from Office to Field Leadership

Lili’s knack for “building something” dates back to her high school years, when a CAD drafting class prompted her to ask her school counselors about career prospects that aligned with her newfound interest. She was immediately steered toward architecture and engineering—construction wasn’t even presented as an option—so she pursued a degree in architecture at UC Berkeley while interning at Cahill Contractors. It was there that she finally realized what she couldn’t articulate to her high school counselors all those years ago: She wanted to build a structure, not design one. After four years at Cahill, she left for Webcor so she could experience delivering different building types.

“I ended up on the PM route because the work came naturally to me,” Lili says. “I stuck with it because I was constantly told I was good at it. Looking back, I was doing what was expected of me without stopping to question why I was still doing it.”

Of course, that eventually changed. She found herself increasingly drawn to the idea of working on the front line of a project, directly supporting trade partners, and perhaps most of all, fulfilling her insatiable hunger for construction knowledge and experience.

Following through with the transition proved more complicated, however. For the better part of a year, she struggled with the risks of leaving her comfort zone—a path on which she was enjoying immense and (comparatively) effortless success—to learn a new skillset midway through her career. Then there were the less-discussed risks—the ones associated with leading a field team as someone who wasn’t a straight, white, cisgender man.

“Being a queer woman of color definitely gave me cause for pause,” Lili says. “At the time, Lisa Pierce was the only woman holding a superintendent title at Webcor. I admired her as someone who came up through the trades and hoped to eventually reach her level of field expertise. Unlike Lisa, though, I would be coming into the job with no real field experience, so I was definitely concerned about how I’d be perceived if I were to run a job as superintendent.”

Fortunately, Lili’s fears were quelled once she started voicing her concerns to her Webcor mentors; all of them assured her she’d make a fantastic superintendent and urged her to go forward with the transition, in part because they wanted to see more women in field leadership positions as well. In March 2021, when BDFP was running at a slower pace, her transition to superintendent became official. She hasn’t looked back since.

“Thankfully, my initial fears never came to fruition,” Lili says. “Everyone I’ve worked with in the field just wants someone who knows their stuff regardless of their race, gender/sexual identity, or anything else. All they care about is a superintendent’s competence, attitude, and ability to deliver the work.”

Steadfast Support From Webcor Mentors

Although everyone with whom she discussed the potential transition fully supported her, her conversation with Sr. Vice President Greg Chauhan gave her the final push she needed to finally commit to the switch.

“He told me that some of the best builders he knew had worked in both the office and the field,” Lili shares. “He said he didn’t get into construction to be a project manager or superintendent—he got into it to be a builder. That perspective really resonated with me.”

When she approached Matt Rossie for his thoughts on which projects would be best for her to potentially lead as superintendent, he advised that her focus shouldn’t be on which project, but which manager. He explained that the right path would be with someone patient and supportive enough to guide her through the learning process.

She wasted no time telling Sr. Construction Manager Ryan Fischer, to whom she’d be reporting as a superintendent, about her plans, emphasizing that although she’d be a superintendent learning basic superintendent responsibilities, she’d also be bringing her unique skills and expertise as a project manager. She knew he’d rotated between Webcor departments in the past, so she was eager to hear his perspective as someone who had tackled a similar learning curve.

“Without batting an eye, he said, ‘Sweet, let’s do it,’” she recalls. “That’s the best form of support anyone can ask for.”

“I was instantly on board with supporting the move and excited to do so,” Ryan says. “Lili’s an eager learner, so supporting and mentoring her has been nearly effortless. Having such a strong foundation in project management meant many of the things we often have to keep a close eye on when working with ‘green’ superintendents were naturally at the forefront of her mind. Because of this, we just had to focus on the basics of field management, and she didn’t need much support in getting a good handle on those.”

Lili commends Ryan for carefully guiding her through superintendent responsibilities, initially assigning her scope-specific packages based on a transition roadmap they’d laid out together, then gradually assigning her entire areas to manage while checking in with her along the way. Looking back, she says, she was fortunate to make the transition on a job as large as BDFP; if she’d done so on a smaller job, she might have been the only superintendent on-site with no one above to support her.

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“The worst thing you can do as a manager is drop someone new right into the middle of an extremely fast-paced project and expect them to know everything,” she says. “I really appreciated having Ryan and Construction Manager Colin Azevedo’s on-site mentorship throughout that first year as superintendent.

“When you’re transitioning like that, you really need someone else there doing the same work as you so you don’t feel like you’re on an island figuring out everything on your own. Having two exceptional, experienced field professionals right there positioned me for a smooth transition.”

The Real Challenges of the Superintendent Experience

Once Lili was fully immersed in the superintendent world, she quickly realized that the challenges she’d anticipated before making the switch—mastering the technical basics, adjusting to the male-dominated field dynamics, etc.—weren’t actually the ones keeping her up at night. The true learning curve, which she continues to navigate today as a senior superintendent, challenged her in a way she hadn’t seen coming.

“Disconnecting from work as a superintendent is much harder than disconnecting as a PM,” she says. “If you mess up as a PM, it takes much longer for the consequences of your mistakes to manifest, and that’s only if the superintendent doesn’t catch and prevent them first. Now, as a superintendent, I know all of my decisions will manifest in front of me within a week. If I made the wrong call on logistical planning, I’ll be watching my terrible decision play out in front of me—trucks won’t be able to make the right turn, people will be on top of one another, and they’ll all be looking at me asking ‘What the hell did you do?’

“These days, if something’s keeping me up at night, I’ll stay up until I’m confident I have a plan. I was not expecting that to be the biggest challenge—the personal sense of accountability that comes with the job. These people aren’t just man hours on a spreadsheet; their livelihood and safety are in my hands.”

That people-first, service-minded approach is the true key to a superintendent’s success, Lili’s realized, especially for a field leadership role that’s traditionally attracted men craving the power, authority, and respect seemingly inherent to the job. In reality, she says, that respect is far from immediate; it’s earned by building trust. It means proving to your team that they can rely on you to not only follow through on your commitments, but to prioritize their well-being regardless of project demands.

“Many people drawn to the superintendent route go into it thinking, ‘I want to be THAT guy—the biggest dog in the room making all the important decisions,’” Lili says. “There’s so much more to it than that. I’ve found that leading with humility, going above and beyond to ensure your trade partners have what they need to be successful, and taking the time to really get to know them are the most impactful steps you can take as a superintendent. The only way I can accomplish anything in the field is if my subs trust me, and the only way they’ll ever trust me is if they believe that I truly care about them.

“Construction is a small world. You’re going to see these crew members again, and they’re going to remember if you mistreated them. Leave your ego at the door, solicit buy-in and opinions from subs, and build camaraderie with your team—those efforts will culminate in a harmonious work environment, which is incredibly rewarding.”

Transitioning Career Routes: Benefits & How it Works

Regardless of intent to pursue a permanent transition to the superintendent route, all PMs and aspiring PMs should strongly consider gaining field experience, Lili says. The exposure will equip them with the knowledge they’ll need to grow as not just project managers, but well-rounded builders. From a collaboration perspective, appreciating each side’s unique challenges and contributions through hands-on experience is also tremendously valuable.

“When you work as closely as a PM and superintendent do, it’s so important to know what each other does,” she says. “The PM/superintendent relationship is always going to be one of the most important dynamics on the Operations side of a job site. They’re the ones managing the project and ensuring it’s profitable. Understanding both sides can only help your growth as a construction professional.”

And for those interested in officially making the switch?

“If you’re a PM, don’t be afraid to try out the superintendent side,” Lili says. “It’s totally OK to change your mind later. Pursuing it doesn’t mean you’ve committed to that route forever—my career trajectory is a prime example of that. If you do decide to switch, be prepared for the heightened sense of responsibility, but more than anything, be prepared for the lifelong memories you’ll create in the process.”

Although the transition process varies on a case-by-case basis, Lili’s was lateral, i.e. she went from being a PM to a superintendent, not a PM to assistant superintendent (the field equivalent of an APM). She advises those interested to simply initiate a conversation with their manager and determine if that lateral transition is possible.

“Switching paths at any stage of your career comes with its pros and cons,” she says. “The industry experience that comes with switching sides once you’ve reached a management or senior management role will ease the learning curve. On the other hand, switching earlier in your career gives you a little more leeway when adjusting to said learning curve. You’ll also have someone above to help guide you through the transition more thoroughly. The higher up you are when making the switch, the higher the expectations will likely be right from the start.”

Both Ryan and Vice President Lindsey Blatz agree that experiencing both the office and field sides can only benefit aspiring construction leaders and strongly encourage all Webcorians to embrace the challenge of learning the ins and outs of “the other side.”

“The more roles our builders can experience along their career path, be it self-perform, project controls, design-build, field supervision, subcontract management, estimating, etc., the better they will be at leading all those focused groups toward a collective goal when they find themselves in that project or department leadership position,” Ryan says. “Some of those ’crossovers’ occur somewhat organically; it’s difficult to not be well-versed in project controls if you manage subcontracts, but with others, it takes a conscious effort to gain that exposure.

“I think the roles of project manager and superintendent are sometimes the most difficult to blend together due largely to the work process and our defined responsibilities and expectations we have for them. The more we can expose all our builders to both sides, the sooner we can stop operating like there are two sides. There are defined responsibilities for each role, sure, but those responsibilities need to be fully understood by all. The best way to do that is by experiencing them first-hand.”

Some may be hesitant to transition from one side to the other due to concerns that the process will delay their path to senior-level management, Lindsey notes. As a Webcor vice president, she sees this very differently.

“While it may take longer to get promoted to senior superintendent or senior project manager, the overall trajectory to executive-level leadership will be faster,” she explains. “Executives need to be able to speak to both sides of a project, so having that well-rounded experience under your belt is a major asset to career growth.”

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