(This Post was Assisted by Claude)
As the president of our board of directors, I interface with the representative from the management company the previous board had retained to help manage our community. I have no information on the points previously discussed regarding expectations and benchmarks for determining effective performance. I do have a copy of the signed contract, but the individual assigned to our neighborhood is a portfolio manager, rather than fully on-site; so having a clear benchmark is often a moving target as additional communities are added to his portfolio and our needs become more complex.
And my dilemma extends to the independent contractors who supply services to the community. When do I step in and when do I turn my attention to a more pressing issue?
Here are a few suggestions from Claude.
Assessing competency and handling underperformance well are two distinct skills. Here’s how to think about both:
Assessing Competency
The most reliable signals are observed outputs and behavior, not credentials or confidence:
- Can they do the work? Give real tasks and evaluate the quality. Resumes and interviews are poor predictors; actual work samples are much better.
- Do they understand the “why”? Competent people can explain their reasoning, not just execute steps. Ask them to walk you through decisions they make.
- How do they handle the unknown? Strong performers say, “I don’t know, but here’s how I’d find out.” Weak ones either bluff or freeze.
- Do they improve with feedback? Learning rate matters as much as starting point.
- Peer and stakeholder signals. The people working closest to someone usually know within weeks whether they’re pulling their weight in doing the job correctly.
A useful framework: separate skill (can they do it?) from will (are they trying?). These require different responses.
Handling Incompetence Compassionately
The compassionate approach is also the effective one — be direct early rather than letting problems fester.
Be honest and specific. Vague feedback (“you need to step it up”) is useless and unfair. Name the specific gap: “The last three reports had calculation errors that required rework. That’s the pattern I’m concerned about.”
Distinguish the cause. Is it a skill gap (they don’t know how), a fit issue (wrong role), a resource problem (no training, bad tools), or something personal (health, burnout)? The cause determines the remedy.
Give a genuine opportunity to improve. A clear improvement plan with defined expectations, support, and a timeline is both fair to the person and protects you legally and ethically. Some people genuinely turn it around when they understand what’s expected.
Separate the person from the performance. “This work isn’t meeting the bar” is very different from “you’re not good enough.” The first is a solvable problem; the second is an identity attack.
Act when improvement doesn’t come. Compassion doesn’t mean indefinite tolerance. Keeping someone in a role where they’re failing — and everyone knows it — is bad for them, the team, and the work. Ending the arrangement clearly and respectfully, with honest feedback and whatever support you can offer (references, transition time), is kinder than prolonged misery.
The hardest part is that most managers either avoid the conversation entirely (unkind in the long run) or deliver it harshly (unnecessary). The goal is to be honest, specific, and human — treating the person as capable of handling the truth.
