John Kenney, CPRC, CEO, Cotney Consulting Group - October 2026
I have worked with roofing companies where nearly every significant estimate passed through one person. That estimator knew the customers, the systems, the crews, the production history and all the small details that never made it into a written procedure. For years, the arrangement seemed to work well. The company trusted the estimator, the bid pipeline kept moving and everyone assumed the knowledge would always be there when needed.
Then something changed. The workload increased. The estimator took time off. Retirement moved closer. In some cases, the person left. Suddenly, the company realized how much estimating knowledge had been held by any one individual and how little of it had been transferred to others. That is when estimator development stops being a training issue and becomes a business risk.
Roofing contractors understand the importance of accurate estimating because every job begins with the numbers developed before the work is sold. What is often overlooked is how long it takes to groom someone who can produce those numbers with sound judgment. A new estimator can learn to use takeoff software, measure roof areas, enter material pricing and apply labor rates. Those skills are important but they represent only part of the job. The harder part is learning how to think like an estimator.
An experienced estimator recognizes when a drawing is incomplete, when a specification introduces risk or when access conditions will affect production. That person understands that two roofs with similar square footage may perform very differently because of staging, height, congestion, detail work or schedule restrictions. Those decisions are rarely obvious to someone who is only learning the technical process.
Experienced estimators also make hundreds of small decisions during the course of a bid. Many of those decisions have become instinctive. They may question a production rate without stopping to explain why. They may recognize a missing scope item because they have seen the same problem before. They may add contingency because the phasing creates a risk that is not immediately visible in the quantities. A junior estimator sitting nearby may see the final number without understanding the reasoning that produced it. That is why simply watching a senior estimator work is not enough. Real development begins when that reasoning is explained.
The next generation of estimators can come from several areas within the company. Some of the strongest candidates begin in the field because they understand installation sequencing, crew movement and the realities of working on a roof. Others come from project management and already understand scheduling, cost control, coordination and customer expectations. Technical salespeople may bring strong system knowledge and supplier relationships. Each background provides an advantage but each also leaves gaps.
A field employee may understand how the work is installed but need help reading construction documents, building scopes, applying pricing and writing clear proposals. A project manager may understand execution but need stronger takeoff discipline. A technical salesperson may know products and assemblies but have limited experience with production rates and labor planning.
There is no single path into estimating. The company’s responsibility is to recognize what a candidate already knows and then build the areas that are missing. Attention to detail matters but so does curiosity. The best developing estimators tend to ask why one job performs differently from another. They want to understand where labor is gained, why certain details create risk and how an estimator decides whether a project fits the company. Those traits are often more valuable than prior experience with a particular software platform.
Once the right candidate is identified, responsibility should increase gradually. A new estimator might begin by completing quantity takeoffs on limited scopes. From there, the person can begin pricing selected portions of a project, attending pre-bid meetings, participating in roof walks and reviewing specifications with a senior estimator. The next step may involve preparing a complete estimate for internal review before taking ownership of smaller or less complex opportunities. That progression gives the developing estimator room to make mistakes, ask questions and learn before those mistakes become customer commitments.
Internal review is one of the most effective development tools a company can use. However, the senior estimator should not simply correct the junior estimator’s work and move on. The review should become a discussion about scope, production assumptions, exclusions, schedule risk and overall bid strategy. A good review should challenge not only the quantities and extensions but also the assumptions behind labor, access, sequencing, exclusions and risk.
Why was that labor rate selected? What conditions could slow the crew? Is the specification asking for something the drawings do not show? Has access been accounted for? What assumptions need to be clarified in the proposal? Those discussions are where judgment starts to develop.
Even experienced estimators benefit from review, particularly on complex work. A second set of eyes can identify missing scope, unrealistic production assumptions or unclear exclusions. When review becomes part of the estimating culture rather than a response to mistakes, it strengthens both accuracy and development.
The field also has a major role in building the next estimator. A developing estimator should attend jobsite visits before work begins and return during production when possible. Seeing the difference between what was drawn and what the crew actually encounters creates understanding that cannot be gained from a screen. Access limitations, material movement, rooftop congestion, protection requirements and coordination with other trades become much more meaningful when viewed in real conditions.
I also believe developing estimators should see completed work and, when possible, difficult jobs. Successful projects show what worked. Problem jobs often teach even more because they reveal where assumptions, planning or production broke down.
Project closeout is equally important. When a new estimator compares the original labor assumptions with actual performance, estimating stops being theoretical. The person begins to understand how crew composition, weather, site conditions, subcontractor coordination and planning affect production. A job that exceeds budget should not simply be labeled a bad estimate or poor execution. The estimator needs to understand where the variance occurred and why. This connects directly to cost history. A company cannot develop strong estimators if completed job information never makes its way back to the estimating department. Production rates, material usage, equipment costs and project-specific conditions should all inform future decisions. The developing estimator should learn not only how to retrieve historical data but also how to interpret it.
One unusual project should not automatically reset a production rate. At the same time, recurring labor overruns on the same type of work should not be dismissed as isolated problems. Learning the difference requires both data and judgment.
Technology has changed estimating significantly and younger estimators often become proficient with digital tools very quickly. That is an advantage but it can also create false confidence. A digital takeoff can measure with remarkable precision but it cannot always tell the estimator whether the crew can realistically achieve the selected production rate under the conditions shown. It may identify a quantity but not recognize the risk buried in a specification, a phased schedule or a difficult access plan. Software supports the estimator. It does not replace the need to understand roofing.
Documented estimating standards also help development but they should provide a framework rather than become a substitute for thinking. Production rates, cost codes, markup practices, proposal language and review procedures should be clearly defined so new estimators are not forced to learn everything through memory and informal instruction. At the same time, standards need room for judgment because roofing projects are rarely identical.
Communication is another area that cannot be overlooked. Estimators interact with owners, sales teams, project managers, suppliers and general contractors. They need to explain assumptions clearly, identify exclusions and defend pricing without becoming defensive. An accurate estimate can still create problems if the scope is poorly communicated.
Having developing estimators present their work internally helps build that skill. It forces them to explain how they arrived at the number and where they see risk. It also reveals whether they truly understand the estimate or have simply completed the process.
Succession planning should begin while the current estimating structure is still stable. Many contractors wait because the senior estimator is productive and the system appears to be working. That is exactly when development should start. Knowledge transfer is much easier when there is no immediate crisis and the experienced estimator still has time to teach, review and explain.
Once retirement is close or the workload becomes unmanageable, the senior estimator is often expected to maintain the bid pipeline while also transferring years of knowledge, a difficult task to accomplish in a few months. Production intuition, customer history, vendor relationships and system familiarity are built over time.
Companies should also think about estimating as a leadership path. Estimators influence which work the company pursues, how risk is priced, what production expectations are established and whether the backlog supports the company’s margin goals. Senior estimators are not simply takeoff specialists. They help shape the future workload of the business.
When employees see a clear career path in estimating, they are more likely to treat the role as a profession rather than a temporary assignment. Mentoring opportunities, defined levels of responsibility and visible advancement all help build that commitment.
After more than 45 years in this industry, I have seen roofing companies spend years building estimating knowledge and then realize too late that most of that knowledge lived with one person. The risk usually is not obvious while that estimator is still producing. It becomes obvious when the company suddenly needs someone else to carry the responsibility.
Developing the next generation of estimators is not about replacing one individual with another. It is about making sure the experience, judgment and lessons built over years do not leave the company when someone retires or moves on. The strongest estimating departments I have seen are the ones where knowledge is shared, reviewed and carried forward.
Every estimate should help develop the estimator who prepares it. Every completed project should add to that person’s judgment. If a company can build that kind of learning into its estimating process, it is doing more than preparing the next bid. It is building the estimating leadership it will need for the future.
John Kenney, CPRC is CEO of Cotney Consulting Group, Plant City. He has decades of experience on commercial roofing projects, providing him with a unique understanding of what it takes to succeed in roofing – on the roof, in the office and at scale. John saw the need to provide contractors with strategic guidance built on real-world field knowledge. Cotney Consulting offers COO on Demand, online training, technology solutions, business advisory consulting, collections, contracts, Castagra estimating training, safety and OSHA training. John partners with FRSA to provide educational seminars. For more information, contact John at jkenney@cotneyconsulting.com or 813-851-4173.