As a general contractor, I pride myself on being a "COMMUNICATION FIRST" professional. For me, effective communication is not just about clarity—it’s about responsibility. It ensures that all parties involved in a project are aligned, expectations are clear, and commitments are honored. In my experience, a contractor who fails at communication and accountability is a risky bet.
That brings me to Ben.
When I first worked with Ben, I quickly realized he did not meet my top two criteria: strong communication and commitment to documentation.
Challenges of Working with Ben:
Avoids signing detailed contracts or making detailed commitments in writing. While verbal agreements were made in details but many of those details were not reflected in the written contract to hold him accountable and therefore there was no written record of what was discussed.
Spotty communication. He would sometimes go radio silent, leaving me guessing about the status of our project.
Minimal responses. If I sent a detailed email, he’d often reply with only two words, addressing just one of my questions while ignoring the rest.
Unreliable payment agreements. He would agree verbally to a payment schedule, only to later demand the full amount unexpectedly.
Given these issues, after the first small project we worked on, I thought: This is not the kind of person I want to work with long-term.
But then, I took a step back.
The Flip Side: The Pros of Working with Ben
Despite all the challenges, Ben had some undeniable strengths:
He delivered. While he wouldn't put any detail in writing, he always got the job done on time and often exceeded expectations.
A good personality. He was pleasant to talk to and had a likable demeanor.
Valuable referrals. He introduced me to high-quality contractors that became valuable additions to my network.
Competitive pricing. His rates were unbeatable, and the quality of work he delivered was excellent for the price.
The Second Chance
Instead of walking away, I decided to give Ben another chance—but with a different approach.
I recognized that his weakness wasn’t his ability to deliver but rather his communication style. Instead of forcing my structured approach on him, I adjusted. I gave him more freedom and less pressure in communication. I provided the necessary resources upfront and gave him space to work on his own terms.
The result? This time, he initiated communication with me. He asked for timelines and resources. By adapting my approach, I saw a shift in how he interacted with me, and we were able to collaborate much more effectively.
The Takeaway: A Lesson in Adaptability
The experience taught me a valuable lesson: Not everyone operates the way we expect them to. Many of the challenges we face in work and life come from our rigid expectations. When we insist that everything be done our way without flexibility, we might miss out on great opportunities and strong relationships.
By giving people space while keeping them in check, we can create a win-win situation. It’s about finding a balance between structure and adaptability.
My Tips for Working with Different Personalities in Work and Life:
Identify the person's strengths and weaknesses early on. Don’t dismiss someone just because they don’t fit your ideal mold—see if their strengths outweigh their weaknesses.
Adjust your approach when necessary. Some people don’t work well under rigid structures. Giving them room to operate can sometimes yield better results.
Set clear boundaries without micromanaging. Provide clear expectations but allow flexibility in execution.
Communicate expectations upfront. If someone struggles with documentation, find alternative ways to ensure accountability (e.g., voice memos, recorded meetings).
Keep your risk management in place. Don’t allocate more risk than you can bear—whether financially, legally, or operationally. No matter how much you trust or like someone, never risk the farm with them if they are unwilling to take proper responsibility for their commitments.
Know when to walk away. If adaptability doesn’t work and someone consistently disrupts workflow, don’t force a partnership that isn’t beneficial.
Final Thought
Taking a chance on people doesn’t mean tolerating unreliability—it means finding ways to maximize their strengths while managing their weaknesses. Not everyone will fit into our system, but sometimes, with a little adjustment, they can still deliver extraordinary results.
Would love to hear from you—have you ever given someone a second chance and had it pay off?
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