A Conversation With Craig Plescia About Confidence, Risk, and Building Something That Lasts
As the founder and CEO of Plescia Construction & Development, he has spent more than 20 years working in commercial construction and learning how to make decisions when the stakes are high and the outcome is never completely guaranteed.
A graduate of the University of Rhode Island who is also continuing his education through Harvard Business School, Craig Plescia has learned as much from difficult projects as successful ones. Early in his career as a business owner, he accepted a project that was not properly scoped or priced. The experience hurt margins, but it also changed how he approached future opportunities. He introduced stronger qualification standards, clearer scopes, and more disciplined pricing.
Other challenges came with growth. Limited brand recognition and inconsistent deal flow made the early years unpredictable. Plescia invested in visibility, built a more deliberate business development process, and created systems that allowed the company to operate without every decision running through him.
That preference for preparation extends well beyond construction. Plescia is interested in mountaineering, rock climbing, aviation, skydiving, and rugby. He also coaches youth rugby, where he has seen how confidence often develops through repetition, teamwork, and learning how to respond after mistakes.
Whether he is thinking about a construction project, a climb, or a personal goal, Plescia tends to return to the same principle: focus on what can be controlled, prepare carefully, and keep moving.
What gives you confidence when you are taking on something difficult?
Preparation gives me much more confidence than motivation does. Motivation changes depending on the day. Preparation is something you can control.
That applies whether I am looking at a construction project, climbing, flying, or setting a business goal. I want to understand the situation, identify the major risks, and know what I am going to do next. You will never eliminate uncertainty, but you can reduce the number of surprises that come from being unprepared.
I also break large challenges into smaller actions. If you only look at the entire mountain, project, or business goal, it can become overwhelming. Once you identify the next few moves, it becomes manageable.
Has your relationship with risk changed over the course of your career?
Definitely. When you are younger, it is easy to think taking more risk automatically means being more ambitious. I do not see it that way anymore.
One of the most useful lessons I learned came from taking on a project that was not properly scoped or priced. We wanted the work, but wanting the work was not enough. The margins suffered, and the project showed me what happens when enthusiasm gets ahead of discipline.
After that, we became much stricter about qualification, scope, and pricing. I still believe in taking risks, but I want them to be understood risks. Saying no to the wrong opportunity can create room for a much better one.
Where do you find inspiration when you are trying to grow?
A lot of it comes from being around people who operate at a higher level than I do in some area. Seeing what someone else has built can change your idea of what is possible.
I do not look at that as comparison in a negative sense. I use it as information. If someone has built a strong company, completed a difficult climb, become excellent at a skill, or created more freedom in their life, I want to understand the habits and decisions behind it.
That is one reason I try to keep raising the bar. Comfort can be useful for recovery, but I do not think it is where much growth happens.
How do you inspire confidence in other people when a project or idea is still uncertain?
I think people become confident when they see that there is a process behind the idea. Telling someone, “Trust me, this will work,” is not very convincing.
I would rather explain what we know, what we do not know, what the biggest risks are, and how we plan to respond. In construction, people are dealing with budgets, schedules, design decisions, subcontractors, and a lot of moving pieces. Pretending there is no uncertainty does not build trust.
Being clear about the challenges usually creates more confidence than trying to sound completely certain.
Was there a point when you realised the business could not continue depending on you for everything?
Yes, and it was an important transition. In the early years, I was wearing too many hats. At first that feels productive because you are involved in everything. Eventually it becomes a limitation.
We had inconsistent deal flow, limited brand recognition, and too much depending on my individual time. We began investing more deliberately in SEO, advertising, industry involvement, and business development. We also created better systems around operations.
The goal was not for me to become less involved. It was to make sure my involvement was focused where it had the most value.
What have activities like mountaineering and rock climbing taught you about business?
They reinforce the importance of making good decisions before you are under pressure. When conditions become difficult, you usually fall back on your preparation and habits.
They have also taught me that turning around is sometimes the correct decision. People can become attached to reaching a summit because they have invested time and effort into getting there. Business can be the same way. You can become attached to a deal, project, or plan simply because you have already invested in it.
Sometimes discipline means continuing. Other times discipline means recognising that the conditions have changed.
How do you stay focused when self-doubt shows up?
I try not to spend too much time arguing with it. I go back to action.
I look at what I can control, break the problem into smaller pieces, and follow the routine. Execution creates momentum. Once you start making progress, even small progress, the problem usually feels different.
That is why I rely more on routine than motivation. A good routine keeps you moving on days when your confidence is not particularly high.
What do you hope younger people you coach or work with learn from you?
I hope they learn that consistency matters more than looking impressive for a short period of time. That is true in rugby, construction, business, and almost anything else.
You build credibility by doing what you said you would do repeatedly. You build confidence by preparing, making decisions, learning from mistakes, and then doing it again.
I also want them to understand that professional success and personal stability should support each other. Building something meaningful is important, but so is having the health, relationships, and control of your time to actually enjoy what you have built.
