The Right Way of Letting Team Members Go: Signals, Checklists, and Fair Steps

This article should help any founder, manager or leader to recognize when you need to let a team member go

Letting go of a team member is one of the hardest decisions an engineering leader can face. But keeping someone who underperforms or misaligns with your team can drag down morale, quality, and trust. This article gives you a practical, no-nonsense guide — backed by engineering leaders like Gergely Orosz and Michael Lopp (Rands) — to help you recognize the signs, do your due diligence, and handle the process fairly.

Spotting the Warning Signs

Watch for red flags across delivery, behavior, and cultural alignment. For example, delivery problems might include chronic missed deadlines, incomplete features or constantly buggy code. In Gergely Orosz’s terminology, a “low performer” is someone doing “less or poorer quality work than expected” – essentially coasting or lacking key skills. On the behavior side, look for repeated conflicts, insubordination, or a defensive attitude. Someone who ignores feedback, complains constantly, or undermines teammates can sap morale. Finally, a cultural misfit might breach core values or norms – for instance, repeatedly disregarding team agreements, showing a lack of integrity, or blatantly disrespecting inclusivity or rules. As Ron Koerth points out, keeping a misfit on the team sets a bad example and drags morale down and can poison the whole team feeling. In fact, when high performers see a coasting colleague tolerated, they often become frustrated or start looking elsewhere.

Consider these common symptoms:

• Delivery gaps: Constantly missing goals or generating poor-quality output (e.g. frequent bugs, incomplete pull requests).

• Behavioral issues: Chronic negativity, lack of collaboration, or blatant rule-breaking. Note if peers begin to avoid collaborating or bring up concerns – a good manager’s “sixth sense” often feels when “the team is off”

• Culture/fit problems: Values conflicts that can’t be overlooked (e.g. harassment, dishonesty, or consistent disrespect of team practices).

If you see multiple such signals persisting over time, it’s a strong cue that something deeper is wrong.

Manager’s Checklist Before Deciding

Before deciding on letting someone go, go through a structured checklist to ensure you’ve given every realistic chance to improve:

• Clear expectations: Have you defined the employee’s responsibilities and success criteria explicitly? Rands (Michael Lopp) emphasizes documenting exactly “what success looks like” and reviewing it with the employee. If expectations were vague or moving, you must fix that before proceeding.

• Regular feedback and conversations: Have you raised the issue early and often? Rands famously asks managers: “Have you had multiple face-to-face conversations over multiple months… where you have clearly explained and agreed there is a gap in performance?”. In other words, don’t bring up a PIP out of the blue. Instead, hold at least three substantive, in-person discussions spanning several months. Make each session a two-way dialogue: explain the problems clearly (ideally in writing first) and ask the employee to repeat back their understanding. Only if they really disagree with your assessment after this should you consider parting ways.

• Specific, documented feedback: Have you provided concrete examples of the problems? A common mistake in bad performance reviews is “zero specifics”. For each issue (missed deliverable, problematic incident, etc.), document exactly what happened, why it mattered, and what needed to change. This isn’t about catching someone in a mistake – it’s about giving them actionable data. When you present feedback, do it in a neutral, coaching tone, not a punitive one.

• Support and remediation efforts: Have you offered training, mentoring or re-alignment? If the root cause is skill-related, the manager should have given opportunities to improve. For example, if the tech stack changed or the role shifted, did you re-train the employee? Rands notes that deep changes in performance require months and repeated coaching. Likewise, Gergely Orosz advises that if the person is willing to train up, “in most cases it will pay to invest in them”. Ensure you’ve genuinely given this support before concluding they can’t improve.

• Realistic expectations: Were the goals fair? Sometimes we unintentionally oversell roles. If the employee was hired with over-ambitious promises or if the role has outgrown their skill set, consider whether adjusting the scope or deadline could help. If the bar truly is too high, no one can fairly meet it – but if the expectations were reasonable and unchanged, then lack of progress falls on the employee.

• Team impact: Have other teammates complained or rallied to help? If you sense that other engineers are now doing extra work or are frustrated that someone else isn’t pulling their weight, that’s a significant signal. High performers won’t stick around forever if they feel they’re carrying slackers. On the other side, if you find that only one outlier is struggling while the rest thrive, investigate why that person is so different – that insight helps you decide if they belong on this team.

• Time and closure: Have you really waited long enough? As Rands emphasizes, coaching performance often takes multiple months and iterations. If you’ve already spent a quarter or more trying to fix the issues, and nothing has changed despite the above efforts, it’s reasonable to start moving toward closure.

Use this checklist as a reality-check. If any of the above boxes haven’t been ticked, pause and address the gap. Only after honest, documented attempts should “let it go” enter the conversation.

Growth Potential vs. Misfit

Not every struggling engineer should be immediately offboarded. The key question is “Can this person improve with support?” or are they fundamentally not a fit?

Begin with empathy and curiosity. Assume good intent: as Matthew Spence puts it, “the overwhelming majority of people want to be good at their jobs”. Often underperformance has external causes: mismatched tasks, personal stress or problems e.g. their relationship, burnout, or unclear goals. Ask diagnostic questions: Are they getting the support they need? Is their work aligned with their core skills? Do they understand the company vision and see how their work matters? Have they simply run a bad cycle or are on the verge of burnout? Pinpointing the real cause is critical – Spence notes “identifying the true underlying cause is usually the hardest part”.

If the problem seems like a skill gap or role mismatch (they haven’t learned a new tech, or the team’s needs shifted), check their willingness to adapt. If they are eager to train up, it’s often worth investing more time. You might even try moving them to a different project or mentor, as suggested in Spence’s “Before you fire them” advice. Sometimes a fresh context or leader can rekindle motivation.

In contrast, if the core issue is cultural or values misalignment – for example, they clash with the team’s work ethic or violate trust repeatedly – then there’s a lower ceiling for improvement. Orosz explains that a company’s culture “can be flexible up to a point”, but if an individual consistently can’t meet the team’s standards, “they aren’t a good fit”. In those cases, no amount of skill training will fix the problem. Similarly, if after coaching they show no accountability (deny any gap, blame others, refuse to take feedback), it’s a sign their willingness to grow is lacking.

Quick growth-vs-misfit check:

• Does the engineer acknowledge the feedback and actively work on it? (Good sign.)

• Have they made any progress on smaller goals?

• Do they volunteer for new challenges or only default to complaints?

• Is the performance gap only in advanced skills, or does it touch on attitude and ethics?

If answers lean toward “yes, they own it” and “we can fix this”, continue coaching. If answers look like “it’s everyone else’s fault” or “I won’t change”, that points to a misfit.

Fair, Empathetic Offboarding

If you’ve run the checklist and still see no way forward, it’s time for a respectful offboarding process. Handle it with clarity and compassion:

• Prepare and involve HR: Before the meeting, ensure all documentation (goals, feedback logs, conversations) is in order. Follow your company’s policies for performance offboarding, and get HR or legal advice on severance and any obligations.

• Be clear but kind in the conversation: Schedule a private, face-to-face (or video) meeting. Explain the decision factually: point to the documented gaps and the attempts made to help. Avoid surprises – the employee should already have been aware via your ongoing discussions. Speak in a coaching tone, not a punitive one. Act like a coach even in this hard talk: give them information and closure, not a lecture. Use compassionate language (“I’m sorry this wasn’t the right fit” rather than “you failed to perform”).

• Maintain dignity and empathy: Listen to their questions and answer honestly but respectfully. It’s normal for people to react with shock or sadness – they may feel blindsided even if you think the signs were clear. Keep the tone factual and calm. Don’t say anything personal or blameful. Acknowledge any positives (“You did well on X and Y; we really tried to find a path forward”) to avoid making it entirely negative.

• Handle team communication carefully: After the departure, you’ll need to say something to the rest of the team, but keep details minimal. As Koerth advises, keep the reasons confidential and express general continuity. For example, “Alex has decided to move on; we’re working through the transition.” Speculating or giving too much detail will breed rumors or resentment. Employees respect honesty, but they trust management only if they feel it was done fairly. If your team trusts your process, they won’t jump to conclusions that you were unfair. Never badmouth the departed person to anyone – that erodes trust in you.

• Close with support: Whenever possible, help the person leave on as positive a note as circumstances allow. Offer a reasonable severance package, outplacement support, or references if warranted. Gergely Orosz and others have emphasized treating people humanely during layoffs and cuts – it protects morale and your company’s reputation. Even after letting them go, you want to be able to say “We wish them well”.

In every step, fairness and consistency are key. If you hold this person to a standard different from everyone else, you’ll lose the trust of your remaining team. By contrast, when you communicate and act clearly, empathetically, and professionally, the rest of the group knows that everyone’s being treated by the same rules. That clarity and respect go a long way toward ending a difficult chapter and letting the team move forward stronger.

Conclusion

No manager or founder enjoys letting someone go, but sometimes it’s necessary to keep the team healthy. Watch for persistent shortfalls in delivery, toxic or uncoachable behavior, and misalignment with your values. Before cutting ties, run through a frank checklist: have clear expectations, documented feedback over months, and real support in place. Distinguish fixable skill gaps or temporary slumps (where training or a new role might help) from fundamental mismatches in attitude or mission. If you decide offboarding is the only fair outcome, do it cleanly: honest yet compassionate communication, consistent treatment, and a coach-like demeanor throughout.

In sum, the goal is to be thorough and humane: make sure you’ve truly tried to help, and then carry out the process in a way that respects everyone. By doing so, you keep standards high, preserve team morale, and uphold the values your organization depends on. It’s never easy, but when handled well it’s the responsible thing for the health of the product, the team, and the person in question.