Why Coaching
Having personally been coached in different areas of my life for the past 10+ years, I think I have a pretty good understanding of why coaching seems to work so well for contractors, and why you might want a coach of your own. There are six reasons:
Being Held Accountable
Being Questioned And Challenged
Being Listened To
Being Recognized For Your Achievements
Being Accepted
Being Motivated
Different people have different needs at different times in their lives, but I find most contractors share all six of these to varying degrees.
For us, the daily grind is unique. We're constantly balancing job site management, crew coordination, client expectations, and financial pressures. Most days, we're so busy putting out fires that we rarely get the chance to work on the business itself. That's where coaching comes in, not as a luxury, but as a necessity for growth.
Accountability
How many times have you promised yourself you'd implement that new CRM, or finally get around to creating those standard operating procedures? As contractors, we're accountable to everyone our crews, our clients, our families, but rarely do we have someone holding us accountable to ourselves.
I remember when I first started working with my business coach. He had me commit to three specific action items between our sessions, nothing overwhelming, just focused tasks that would move my business forward. Things like implementing a new follow-up system for estimates or creating a more efficient hiring process.
The difference was huge. Knowing I'd have to report my progress made me prioritize these business-building activities over the everyday emergencies that used to consume my time. Just like how the great athletes all had coaches who reviewed their "game film," analyzed their performance, and held them to higher standards than they might have held themselves.
There's a joke in our industry: the good news and bad news about being a contractor is that you're your own boss! Without that external accountability, it's too easy to let critical improvements slide. Having someone guide you in committing to specific actions between meetings, then having to report on those things, dramatically improves your follow-through on your own best ideas.
Questioned and Challenged
The more successful your contracting business becomes, the less people around you will challenge your thinking. It’s easy to end up surrounded by “yes men/women”. Your employees aren't likely to push back on your ideas. Your spouse might not understand the complexities of your business decisions. Your buddies just want to talk golf.
That's the value of having someone who can be objective and frank. When I told my coach about my plan to expand into commercial work, he didn't just nod along. He asked tough questions: "How will this affect your cash flow during the longer payment cycles? What additional equipment will you need to invest in? How will you handle the different permitting requirements?" Having someone with no agenda challenge my thinking, helped me refine my approach and avoid costly mistakes.
Being Listened To
Running a contracting business can be incredibly isolating. You carry the weight of every decision, but often have no one to really talk to about the challenges you face. Your employees look to you for certainty, not vulnerability. Your family cares but may not understand the specific challenges of our industry.
There's power in having someone who truly listens, not just waiting for their turn to speak, but actively engaging with your thoughts and concerns. I found my coach became my sounding board, and the person I could talk to about anything from cash flow worries to difficulties with a problem employee.
A Newsweek article once described business coaches as "part therapist, part consultant," and that rings true. Having someone who listens without judgment or agenda often leads to discovering your own solutions. I've often talked through a challenge with my coach and arrived at the perfect answer simply because he created the space for me to think out loud.
If you were to decide to have a business coach, I think there’s additional value in having someone like myself who comes from your world - the contracting world. Someone who understands the unique challenges you face from seasonal fluctuations to supply chain issues to labor shortages, etc.
Being Recognized For Your Achievements
Every contractor knows the feeling: you land that big project you've been chasing for months, or you finally implement that new scheduling system that increases your crew's efficiency by 30%, and... nobody really gets it. Your employees might be happy about steady work, but they don't understand the persistence it took to win that contract. Your family is supportive but they don't grasp the significance of the improvements you've made.
We rarely take time to acknowledge our own victories. Having someone who recognizes your accomplishments, who understands the blood, sweat, and tears behind them, provides validation that we all need but rarely receive. Being part of a coaching program gives you an appreciative audience who "gets it," who understands the significance of what you've achieved, and who is secure enough in their own success to genuinely celebrate yours.
Being Accepted
We contractors often approach business differently than what's taught in business schools. We're mavericks; practical, hands-on problem solvers who often rely on unconventional methods. I've found that many successful contractors feel like outsiders in traditional business settings because we don't always follow the conventional wisdom.
I remember sitting in a chamber of commerce meeting, listening to people discuss theoretical business concepts while thinking, "None of this applies to what I do every day." It felt like being a fish out of water, and that feeling followed me through most business interactions outside my immediate industry.
There's profound relief in being accepted for who you are, without needing to mask or cautiously edit your thoughts. We all have those industry-specific quirks and approaches that might seem strange to outsiders but make perfect sense to fellow contractors. This acceptance creates a space where real growth can happen because you're not wasting energy trying to fit into someone else's idea of how a business should operate.
Being Motivated
Even the most driven contractors experience periods of burnout and frustration. When you're dealing with weather delays, permit issues, problems with material, and crews calling in sick – all while trying to keep clients happy – it's easy to lose sight of why you started this journey in the first place.
Motivation isn't just about high-energy pep talks. It comes from being around others who share your challenges but continue pushing forward. Just as professional athletes earning millions still need coaches to motivate them to do the behind-the-scenes work that leads to peak performance, contractors need that external spark to maintain momentum through the inevitable ups and downs.
In my experience, seeing other contractors overcome obstacles similar to mine renewed my determination. Hearing their success stories provided practical blueprints I could adapt for my own business. The accountability, recognition, and community all contributed to a sustained motivation that I couldn't generate alone.
While all motivation is ultimately self-motivation, there's no denying the powerful influence of the people you associate with, the environments you put yourself in, and the successes you're exposed to.
If any or all of these six items resonate with you, then the single best investment you can make isn't in new equipment or expanded facilities – it's in finding the right coach or coaching program for your contracting business. The return from improved decision-making, increased accountability, and clearer strategic thinking will dwarf any other investment you might make.
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