In this solo instructional video, Tristan Wilson distills the practices that separate top construction estimators from the rest. Drawing on observations of elite estimators and the book Atomic Habits, he argues that success stems from systematic habits rather than extra hours. He outlines eleven concrete habits: (1) regular field visits to build on‑site knowledge; (2) a monthly bid‑performance look‑back to compare actual results with estimates; (3) Sunday‑night weekly planning to prioritize deep work; (4) estimating managers periodically bidding jobs themselves to stay sharp; (5) milestone field check‑ins during construction; (6) continuous scouting of new tools and technology; (7) cultivating long‑term, trust‑based relationships with subcontractors and suppliers; (8) taking daily walks or movement breaks to avoid desk stagnation; (9) recognizing when a job exceeds personal capacity and asking for help early; (10) immediately scheduling all bid‑package meetings to avoid procrastination; and (11) tailoring work hours to personal peak productivity. He reinforces these habits with a personal anecdote about losing a $6.5 M airport resurfacing bid due to last‑minute procrastination, illustrating the cost of unpreparedness. Wilson concludes that great estimators are systematic, business‑minded, and prepared, and he offers a simple self‑assessment: would you be comfortable letting a bid go out without reviewing it?
Chapters
What separates the best estimators from everyone else? I have the pleasure of spending a lot of time with what I believe are some of the best estimators in the world. And what I've learned from watching them work day in and day out is that the best estimators have systems. They're not freewheeling it. They have a system and they have structure and they follow a process. There's a great book called Atomic Habits written by James Clear, and he says that you don't rise to the level of your goals, you actually fall to the level of your systems. And that is exactly what I've seen with the best estimators. One of the biggest and most important things an estimator can do is go spend time out in the field. And I know it's really counterintuitive. Because most of estimating gets actually done behind a desk. When you're estimating work, you're basically picturing in your brain how the job should be built. And you're able to build this kind of like mental model where you can actually visualize the project being built and how long stuff is going to take and also understand some of the constraints that the field is going to be up against. You can't really understand all of that and appreciate what the field is up against if you don't Go out to the field. Go physically visit the field. Take a ride with them. Get in the truck. You're gonna get so much knowledge out of that, and I can hear the excuses already. I can hear people saying, "I'm too busy. I've got ten jobs that are bidding in the next eight weeks. I just don't have the time." Make the time. It's totally worth it. Another great habit of an estimator is to build a monthly look back habit and see. A few key things. How are the jobs that I've bid actually performing compared to what I thought they would be bid at? The worst estimators just set it and forget it. They don't even care. The best estimators go out and learn to see how close am I? What patterns are there? Where can I maybe take some of the knowledge that I'm observing from the field and also from the data and use that to help make my future bids even sharper? So looking back at past bids every month, print out the cost reports, print out the job status reports, print out the work in progress or the WIP. How are we doing? How are we doing compared to where I thought we would be? Talk to the project manager, talk to the superintendent if you're not also a project manager, understanding how they feel about the budget. Where did we miss? Where could we have been sharper? You always want to try to learn and grow and be better, and you can't just stay stagnant. One other thing that great estimators do is they plan their week on Sundays. So I used to have this thing called the Sunday scaries where I was an estimator project manager and I would have a ton of stuff to do that week. And Sunday would come around and I'd have these grand ideas of all the work I was gonna do over the weekend. And I probably didn't get to any of it 'cause I was super busy and burnt out 'cause it was a long week. And then I'm freaked out Sunday night and Monday morning 'cause I don't really have a plan for the week. The best estimators sit down and figure out what are my priorities for the week? What do I need to get done this week? What's absolutely necessary? And where am I gonna spend my time? And block out time and put it on the calendar and focus on the deep work that needs to get done in order to really be able to put together great bids. If you if you spend even ten minutes on this putting together a to-do list for the week on Sunday, I guarantee you you're going to feel a lot less worried and a lot less concerned about the week ahead. Another thing that is a little bit controversial, but I believe very strongly in this: If you are the manager of the estimating team. I believe that it is very important for you to every once in a while roll up your sleeves and go bid a job. And the reason why is because it keeps you sharp. It makes you understand all the tools that your team is using. It keeps you sharp and fresh with your bid reviews. If you actually know how to use the tools that your folks are using, you're able to ask the right questions because you really understand the work. What can happen is sometimes you become disconnected and you become so far disconnected that people can tell and they're kind of like, I'm not going to go to them with the hard question because I know that they don't really know how to use this tool. I know that they haven't estimated in years. What some of the best managers, so, you know, VPs, presidents, as well as estimators or estimating managers, every once in a while they'll go and bid an actual job. So having that keeps you sharp and keeps you relevant, frankly. Another one is to really As jobs are getting built, go check in and go spend time in the field and understand at certain key milestones, how are we doing on this job? Aside from what the cost report says, like go talk to the actual people. Like, how is the job going? How is the bid progressing? And do that, especially on big jobs. You want to be doing that, you know, as the job's 25, 50, 75, 100% complete. You don't want to wait all the way until the end. Another thing great estimators do is they're constantly looking at new tools and technology. I mean, We work in the AI space and it changes, you know, monthly, weekly, sometimes even daily, right? So estimator, the best estimators are always out there looking at what's a potential way for me to possibly save time and get my work done really quickly without sacrificing the quality. Another thing that I think gets overlooked by many, many estimators and the best estimators do is they establish long-term relationships with their subcontractors and suppliers. It's easy to hide behind the computer screen, And just simply pick the low bid. And when they call you, if the job's been awarded, send them to the project manager and wash your hands of it. That's not the way that the best estimators work. The best estimators, they get to know their subs, they get to know their suppliers, they build trust with them, and they regularly go out and spend time with them in person. You don't want it to be transactional. These are contractors too. These are great companies. You want to be able to establish strong relationships with them. Don't just live off of RFQs in the email. Go spend time with them. Talk to them. Part of estimating is you're sitting at your desk for long periods of time. So I think taking daily walks, getting outside, moving around a little bit. This is something that I've seen some of the best estimators do. They'll be in the parking lot, maybe having a call, maybe they're listening to a podcast, but they're getting out of their office and they're kind of getting a little, you know, movement. It's very important. If you're sitting at your desk for 8 to 10 hours a day, you can't become, you know, stagnant. You need to get out and move around. It's going to help you. You'll be more productive over time. Another thing that the best estimators do is if they see a job coming up that's going to be too much for them to handle, they have the humility to stop and say, hey, this is a big job. I'm going to need some help on this. The inexperienced estimator tries to do everything themselves and then winds up the midnight before the bid review realizing, oh shit, like I can't finish all of this work that needs to get done on this bid. And then they have to get rescued. And I've been there before and it's, it's not a good feeling. Asking for help early is absolutely critical because you're being realistic. And this is also part of what being a great estimating manager means is you can kind of sense if somebody is overloaded or if they can't handle a whole job and they need, they need some help. In line with that, the best estimators, the second they get a bid package, second it comes in, they schedule every single meeting for that job. And they do all this immediately the second they get the bid because they don't want to wait and they don't want to procrastinate. When you wait on things and you kick the can down the road, you're going to miss important deadlines. And it's important. I'm telling you, like, I can just about track how quickly people would set up the meetings to how well prepared they were. At the bid review. Really cool thing about estimating is that you get a good bit of time. You can kind of control your own schedule. Like, I know some estimators that get to the office at 6 AM every day and they're out of there by 3. Other estimators, maybe they like to work later. Maybe they like to get to the office at 10 and they maybe work till 6 or 7 o'clock. It totally depends on whatever works for you. And provided that, you know, your company and your boss is cool with it, find the best work hours that, that, that are kind of where you're at your peak. And this varies by person. You know, it's not necessarily the same for everybody. So the bottom line is that like the estimators who consistently win more jobs and whose bids are more accurate are not the ones that are the most technical or the ones that are the most experienced. It's more than just like counting quantities and, and pricing items. It's like building up this set of really good and healthy habits that are going to sustain for the long term. So I'm going to tell you a story. I was once the world's worst procrastinating estimator. We had a $6.5 million bid. It was a 40,000-ton airport resurfacing job, a perfect job for the company right in our wheelhouse. And I worked on the bid. I was excited about the job, and I was also busy with a lot of jobs I was managing in the field. And I waited until the last minute to put my bid together. So a few days before the bid, I started working on it and we got an addendum. And it said that we had to have the subcontractors fill out the special form, the ones that we were going to use on the bid. And, and I didn't send it out until the day before the bid. I stayed up almost all night the night before putting together the bid. The bid review, we went through it, everything was good. The bid review was fine. I picked the subcontractors that I was going to use. The bid was due at 10 a.m. We got the last form from the subcontractor that we decided to use at 9:40 a.m. We started scanning the bid package in because we could upload it onto the bidding website. And I was sitting there with my my administrative support team. And at 10:00 AM, we pressed submit on the bid and there was a red error that flashed up on the screen and it said, bid not accepted. Our bid was 37 seconds late. And I was in shock because we found out 10 minutes later we had somebody at the pre-bid. Opening, we would've had the low bid on the $6.5 million bid, and our bid was not accepted because I had procrastinated and waited until the last minute. And when that happened to me, it shook me to my core. And I said, never again will I ever be unprepared for a bid because I absolutely hate this feeling. And I got a really hard time for it, as I deserved. I got the opportunity, thankfully, to improve and to correct. The error that I had had. And I said, I'm never going to be unprepared like this again. And that was kind of a new day and a new awakening for me. And what I learned was that the best estimators are always prepared. They come prepared. They're never rushing. They're never waiting at the line. They're never working on stuff at the last minute. Bad estimators are unprepared. Their items are incomplete. If you ask about something, they say, oh yeah, yeah, yeah, I'm, I'm, I'm going to get to that. I'm gonna call that person. The best estimators, when you sit down to a bid review, they're ready to go. They have done the actual work that's required in order to have a great bid. I think the other thing too is that great estimators think like business people. They're not just saying, I am just purely focused on doing takeoffs and throwing production rates in. They think about how's the job actually gonna get built? What's this owner like to work for? How do I make sure that I get the costs right on this job 100% and that I'm actually taking risks in taking chances that we should be taking. The worst estimators are horribly conservative about everything or tremendously aggressive about everything, and you have to constantly pull them back. Estimators have to be willing to challenge. Estimators have to be willing to be challenged. And the best ones are open-minded and prepared, not just shooting from the hip or lazy. The best estimators ask the right questions. They have looked at the drawings and looked at the specs and talked to the owner. and understand what the intent of the job is and have cleared up any inconsistencies upfront. The bad estimators wait until you ask about it and then they go ask the owner. So the question is, how do you measure how great an estimator is? You ask yourself, how comfortable would you feel if that bid went in without you even looking at it? And if you can say confidently that you would actually be okay, Without you having looked at that bid, you have an awesome estimator. And if you say that you would feel awful and, and would never let them submit a bid without your reviewing every single detail, you've got work to do.
