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17 Lessons on Leadership: Tough Decisions in Employee Termination

By Brett Farmiloe

Posted on May 12, 2025

17 Lessons on Leadership: Tough Decisions in Employee Termination

Leadership in the home building industry often requires making difficult decisions, especially when it comes to employee termination. Drawing from expert insights, this article explores the complexities of team management and the importance of maintaining a strong company culture. Learn how effective leaders navigate tough choices to foster high-performing teams and long-term success.

Evolve or Exit: Navigating Team Growth
Prioritize Culture Over Individual Talent
Tough Choices Shape Effective Leadership
Realign or Release: When Paths Diverge
Toxic Talent: The Cost of Keeping
Clarity and Feedback Foster High Performance
Trust Trumps Talent in Home Building
Sensitivity in Difficult Transitions Matters
Leadership Measured in Tough Moments
Boundaries Show Care in Leadership
Delayed Action Signals Negotiable Excellence
Growth Alignment: Key to Long-Term Success
Consistent Check-ins Prevent Disengagement
Protect Team Culture, Set Clear Boundaries
Fair Expectations from Day One
Clear Technical Criteria Prevent Future Issues
Balancing Empathy and Accountability

Evolve or Exit: Navigating Team Growth

One of the most difficult decisions I’ve made as a business owner was letting go of an early team member who, by all accounts, had done nothing wrong. She was reliable, friendly, and had been with us through those scrappy early days when everyone wore multiple hats. But as the company matured, our challenges became more complex—and I started to see a growing disconnect between where we were headed and where she was comfortable staying.

She wasn’t failing in her role. In fact, she was performing exactly as she had when we hired her. The problem was, the role itself had evolved. We needed someone who could anticipate what was next, think strategically, and help us scale—not just maintain. She was content with the status quo, and while that might work in a static environment, it became a liability in one that was growing fast and demanding more forward-thinking at every level.

Letting her go was incredibly tough. There were no dramatic mistakes or red flags to point to—just a quiet misalignment that had become impossible to ignore. But what I took away from that experience was the critical importance of hiring with scalability in mind. You don’t just need someone who’s a fit for the role today. You need someone who can grow with it tomorrow.

Now, during hiring, I pay close attention to signs of future focus: Does the candidate talk about learning? Do they ask questions about where we’re headed? Are they energized by change, or intimidated by it? Because if they’re not thinking ahead, they’ll eventually hold us back—through no fault of their own.

It taught me that building a great team isn’t just about skills or culture fit. It’s about mindset. A team that’s wired for growth will grow with you. One that isn’t, won’t—and as a leader, it’s your responsibility to know the difference.

Linn Atiyeh, CEO, Bemana

Prioritize Culture Over Individual Talent

I faced a particularly challenging termination decision with a Digital PR Manager who produced exceptional work but consistently created a toxic environment for their team. Despite their talent, several team members had raised concerns about public criticism, taking credit for others’ ideas, and dismissive behavior toward junior staff.

After documenting these issues, I implemented a performance improvement plan focused specifically on leadership behaviors and team collaboration. We provided coaching resources and clear behavioral expectations. Despite some initial improvement, the problematic behaviors resumed within weeks, and two valuable team members were considering leaving because of the environment.

Making the final termination decision was difficult because this person’s creative work genuinely benefited our clients. However, the ongoing impact on team morale, collaboration, and retention ultimately outweighed individual contributions. After careful consideration and consultation with HR, I made the decision to let them go.

This experience taught me that leadership requires protecting the organizational culture even when it means losing talented individual contributors. I learned to establish clearer behavioral expectations during hiring and onboarding, recognizing that technical skills alone aren’t sufficient for roles affecting team dynamics. Most importantly, it reinforced that delayed action on toxic behaviors signals to your team that you value certain contributions over their wellbeing and professional growth. Since this experience, I’ve become more proactive in addressing cultural fit issues before they create lasting damage to team cohesion.

Aaron Whittaker, VP of Demand Generation & Marketing, Thrive Digital Marketing Agency

Tough Choices Shape Effective Leadership

Letting someone go is never easy. I once had an employee, a genuinely kind person, who consistently underperformed. Coaching and additional training didn’t bridge the gap. It felt like letting go of a teammate in a close game, knowing it might hurt team morale but also recognizing it was necessary for the team’s overall success. It taught me that leadership sometimes means making tough choices and balancing individual needs with the greater good. Like a conductor leading an orchestra, sometimes an instrument needs to be tuned or even replaced for the harmony of the whole.

Steve Fleurant, CEO, Clair Services

Realign or Release: When Paths Diverge

Letting an employee go is always a difficult decision for me. I’m very selective about who I bring onto the team, and most of our employees have long tenures, so when someone isn’t working out, it’s never a decision I make lightly.

The most challenging situations are when someone who was once a strong performer begins to fall short of expectations. A few years ago, I faced this with a long-term team member who had been a high achiever early on. They brought in high-value clients and mentored junior recruiters. We had even considered them for a leadership position. But over time, their performance declined significantly. Their placement rate dropped, and multiple clients shared concerns about missed follow-ups, which damaged our relationships and credibility.

Because I had seen what they were capable of, I didn’t make a snap decision. We had several coaching conversations and implemented a performance improvement plan. Unfortunately, despite our efforts, the issues persisted. It became clear that their performance was affecting team morale, client satisfaction, and ultimately, revenue.

When we finally had a candid conversation about their future with the company, they shared that their passion for recruiting had faded and that they were thinking about a career change. That insight helped bring clarity to a very tough decision.

This experience taught me that leadership isn’t just about supporting employees at their best, but is also about recognizing when someone’s goals and interests have shifted. People change, and so do companies. Sometimes, even with the best intentions, it becomes clear that continuing the relationship isn’t productive for either party. As difficult as it was, letting them go allowed both of us to move forward. It reinforced for me that good leadership requires empathy, honest dialogue, and the courage to make hard decisions when the alignment just isn’t there anymore.

David Case, President, Advastar

Toxic Talent: The Cost of Keeping

A few years ago, I had a project lead who was technically excellent but toxic in team settings. Jobs were getting done, but morale was plummeting. We lost three junior staff members in six months, and the feedback consistently centered around the same name. I issued warnings, offered coaching, and even restructured workflows. Nothing changed. The day I called him into the office, I already knew the numbers—$14,000 lost in rehiring costs, a 9% drop in team output, and a noticeable shift in vendor sentiment. It had to happen, and it had to happen quickly.

Letting him go reset the tone overnight. I learned that leadership is not about who can perform solo. It is about who raises the standard for everyone else. When someone poisons the culture, no skill set is worth it. The team took a breath, stepped up, and within six weeks, we won a $210,000 contract from a client who said our team “just clicked.” That moment made me anchor every hire, every promotion, and every restructure around one question—does this person make us stronger together?

Rick Newman, CEO and Founder, UCON Exhibitions

Clarity and Feedback Foster High Performance

Letting someone go is hard. But letting your team down by avoiding it is worse.

One of the most difficult decisions I ever coached a client through was letting go of an employee they had worked with for years—a well-meaning, likeable person who simply wasn’t performing. The team knew it. The clients knew it. And eventually, the business owner had to acknowledge it too.

We approached the situation with a tool I use with all my clients: a What Success Looks Like (WSLL) plan. It’s a one-page roadmap tailored to each team member, outlining three things for a 90-day period:

What’s non-negotiable

What “good” looks like

What would “blow the boss’s mind”

This gives clarity. It also gives fair warning.

The employee in question had clear, realistic targets and support—but three months in, the non-negotiables still weren’t being met. At that point, the decision became far less murky. The conversation wasn’t personal—it was professional, anchored in transparency and agreed expectations.

What did the business owner learn?

That leadership isn’t about being liked; it’s about being clear. That avoiding difficult decisions sends a message to the rest of the team: mediocrity is tolerated. And that when you create a culture of clarity and feedback, your high performers feel seen, and your underperformers feel the responsibility to step up or step out.

I often say to business owners: your job is not to serve the clients. Your job is to serve your team. When you do that, they serve the clients. The clients grow the business. And the business takes care of you. That’s the Cycle of Business. But it only spins when everyone on the team is rowing in the same direction.

Letting someone go isn’t the worst thing that can happen to a leader.

The worst thing? Keeping someone who shouldn’t be there… at the cost of those who should.

Christine Beard, Business and Executive Coach, Christine Beard Business Coach

Trust Trumps Talent in Home Building

Indeed, it happens. No one enjoys this aspect of the job, but sometimes it’s necessary. We had a housekeeper a while back whom clients loved—warm, great with families, the kind of person who remembered how you took your coffee. However, over time, little things added up: missed details, showing up late, and eventually, a client’s antique vase was broken because corners were cut. We tried retraining and shifting her to lighter-duty homes, but the focus just wasn’t there anymore. When we finally had to let her go, it wasn’t about blame; it was about trust. Clients hire us because they need things done right, not almost right.

On top of that, what surprised me was how much clarity it brought. Instead of dreading tough decisions, I started seeing them as a way to protect both our team’s reputation and the employees who do fit. Now, we’re more precise about setting expectations early, not just regarding skills, but also how seriously we take reliability. Interestingly enough, that housekeeper actually thanked us later. She found a job at a boutique hotel where her pace was a better match. Sometimes, the right decision isn’t just about the business; in fact, it’s about helping people land where they’ll thrive.

Brooke Barousse, CEO, Lexington Executive and Household Staffing

Sensitivity in Difficult Transitions Matters

I once had to make a decision that stayed with me for weeks. We were completing a high-specification home build in the countryside, and one of our senior site managers had been overseeing the finishing stage. From drawings to groundwork, he understood the process, but he started cutting corners with site inspections. He believed the crew could handle it alone, which, in theory, sounded efficient. In practice, we missed a drainage alignment that cost us a full week and a difficult conversation with the clients. The challenging part was, this wasn’t about skill. It was about mindset. He valued speed over thoroughness, and for our type of work, that compromise creates a ripple far deeper than a single mistake.

Dismissing him wasn’t about punishment. It stemmed from knowing the kind of culture we protect. Every house we design, every layout we approve, it all carries our name long after we’ve packed up the last tool. What that moment taught me was simple: leadership means safeguarding the invisible threads. The ones between trust and delivery, between pace and precision. When those threads fray, it’s not about who’s liked or who’s been around longest. It’s about who’s truly aligned with how we build—not just structures, but a way of working we believe in.

Dan Davidson, Design Director, Design Team

Leadership Measured in Tough Moments

A while back, I had to make the tough decision of letting go of an employee I’d maintained for years, enduring multiple performance improvement plans alongside repeated attempts at additional support. Despite being highly regarded, the business changed its direction, and the employee’s performance stagnated over several years. Multi-layered performance improvement opportunities, coupled with additional support, did not work.

It was evident that their role was out of sync with their strengths. This created an additional burden in the form of an increased workload, coupled with lowered employee morale throughout the company. Even though this decision was easy for me from a business perspective, the emotional impact hit me as I had to witness a well-respected individual enduring this personal change, all while lacking the emotional support to help navigate through the transition.

What I learned is that in attempting to act for the good of both parties, a leader is revealed, even if the action requires extra effort. I made the decision by collaborating with the employee first and establishing reasonable expectations. Then, I guided them with robust feedback, framing the post-conversation as a supportive career transition bolstered by a powerful recommendation that made role-suited positioning almost effortless. This lesson reinforced my opinion that leaders fundamentally ought to act in all constituents’ interests without avoiding difficult actions when needs are approached with sensitivity.

Mike Szczesny, Vice President, EDCO Awards & Specialties

Boundaries Show Care in Leadership

Across five startups, I’ve had to make my fair share of hard decisions, but none weigh heavier than letting someone go. One experience, in particular, has stayed with me.

We had an early hire who brought a lot of energy and heart to the team. They were there from the beginning, helped build our culture, and were incredibly well-liked. But as the company grew, the role outgrew them. The demands shifted, the complexity increased, and despite coaching and support, the gap between what the role needed and what they could deliver kept widening.

I reached a point where keeping them in the role wasn’t just hurting performance but also starting to damage the team’s trust in leadership.

Letting them go was gut-wrenching. But here’s what it taught me: that leadership isn’t about avoiding pain but rather carrying it as well. It’s about being honest early, being fair throughout, and being clear that accountability isn’t personal but structural. What made the situation bearable was that we handled it with respect, transparency, and support. We didn’t just cut ties; I helped them land somewhere where their strengths were a better fit.

And that experience reminded me that leadership is measured in the hard moments. People watch how you handle exits. They watch whether you flinch or face it. And if you do it right, even the person you let go walks away with their dignity intact, and the team walks away with more trust in your judgment.

Jeff Mains, Founder and CEO, Champion Leadership Group

Delayed Action Signals Negotiable Excellence

Letting someone go is never easy. For me, one of the hardest decisions came during our early days when I had to let go of a team member who was incredibly passionate but consistently unreliable. They were often late, missed key prep days before events, and created stress for the rest of the team—even though they had a good heart and truly believed in our mission.

I kept giving chances because I wanted to believe things would turn around. But eventually, I realized that holding on was doing more harm than good—for them, for the team, and for the experience we promised our guests. Sitting down with them and having that honest conversation was gut-wrenching. But I kept it respectful, clear, and compassionate. I also helped them find a more flexible opportunity that fit their lifestyle better.

That experience taught me that leadership isn’t about avoiding hard conversations—it’s about facing them with empathy and clarity. Sometimes caring means setting boundaries. And if you lead with integrity, people may not agree with your decision, but they’ll respect the way you handle it.

Andrea Sankaran, CEO, Lotuswood Organic Wellness Farm

Growth Alignment: Key to Long-Term Success

The most challenging decision I’ve made as a leader wasn’t about an underperformer. It was about letting go of someone who was showing up and working hard—but in the wrong role.

Several years ago, I had an employee who was exceptional at certain things: creative, kind, and a team player. However, they were in a role that demanded precision, speed, and technical skill—and despite their best efforts (and ours), it wasn’t working out.

Here’s the twist: they were also one of the most liked people on the team. This meant that every signal was telling me: “Be patient. Don’t rock the boat.”

So I did what many leaders are tempted to do—I delayed. I avoided the conversation longer than I should have because I told myself I was being compassionate. But what I was really doing was protecting myself from the discomfort of the decision.

When I finally had the difficult conversation, the employee’s response stopped me in my tracks. They said: “I knew this wasn’t working. I was just waiting for you to say it out loud.”

That moment taught me one of the deepest lessons about leadership that no handbook prepares you for: Staying silent isn’t kindness. Clarity is kindness.

What I also realized was that my delay hadn’t just impacted this one person—it had quietly stalled the team’s momentum and created confusion around expectations. When leaders hesitate to act, they unintentionally signal to the rest of the team that excellence is negotiable.

Since then, I’ve made it a principle to hold what I call “mutual reality checks” with my team—regular, open conversations about fit, energy, and alignment, not just output. This allows space for course-correcting before things fracture. It also honors the fact that sometimes, letting someone go isn’t about failure—it’s about freeing both the person and the team to move forward.

The hardest leadership moments are the ones that test your willingness to prioritize the long-term health of the business and the dignity of the individual at the same time. And if you can hold both of those with care, you walk away better—and so do they.

Gillian Bell, Chief Revenue & Growth Officer, Comfrt

Consistent Check-ins Prevent Disengagement

Years ago, I hired what I thought was my picture-perfect assistant. She was everything I had hoped for—organized, intuitive, emotionally intelligent, a true extension of me. From day one, it felt effortless. We were in sync. I genuinely felt lucky to have found her.

But over the years, things began to shift. At first, it was small, rare mistakes—easily fixable, easily forgiven. But slowly, they grew in frequency and impact. Despite multiple conversations and support, the mistakes started to affect not just operations, but my clients, my reputation, and ultimately, my ability to trust her. And after one particularly high-stakes misstep, I had to make the incredibly painful decision to let her go.

I was devastated. Not just because I lost a team member, but because I lost someone I had invested in—professionally and emotionally. I kept asking myself: What happened? Why did something that once felt so aligned fall apart?

And then it hit me. Working in a close partnership like that is a lot like driving two cars side by side down a long road. If one of those cars starts driving just a little bit faster (or slower), you don’t notice it right away. But over time, the distance grows. Slowly, then suddenly, you realize you’re no longer side by side.

The business had grown. The clientele had grown. And so had their expectations. I had grown. And despite offering support, coaching, and professional development, she just hadn’t grown with me—and the business.

That experience taught me one of the hardest truths about leadership: it’s not just about who someone was when you hired them—it’s about who they’re becoming as you grow. Loyalty matters, but alignment matters too. And sometimes, the kindest and most responsible decision—for both of you—is knowing when the road ahead requires different passengers.

Sylvie Di Giusto, Keynote Speaker & Author, Sylvie di Giusto

Protect Team Culture, Set Clear Boundaries

In my early days of overseeing a team of young staff, one part-timer, tasked with leading a series of digital activities, began to ghost shifts, sometimes not showing up at all. We all knew this otherwise committed person had a difficult personal situation, and each time it happened, one of us readily stepped in to bridge the gap.

However, the absences continued, and the gaps continued to be filled by team members whose enthusiasm soon waned. After a few weeks, I knew I had to act. I sat the employee down, explained the impact of their absence on the team, and let them go, offering advice on finding a less demanding role elsewhere.

The experience taught me that leadership isn’t just about making exceptions for someone’s struggles—it’s about being present and accountable for the entire team. I realized that ignoring red flags, even out of empathy, can erode trust and put others at risk. From then on, I’ve prioritized consistent check-ins with staff, ensuring no one feels unsupported enough to disengage.

Stanley Anto, Chief Editor, Techronicler

Fair Expectations from Day One

A few years ago, I had an employee who was incredibly creative—wildly talented with ideas—but struggled with time management and communication. I coached, redirected, and provided space for growth, but the missed deadlines and lack of follow-through began impacting clients and the rest of the team. That’s the challenging part: when one person’s chaos starts spilling into everyone else’s order.

Letting her go wasn’t about talent—it was about trust, consistency, and protecting the culture I’ve worked hard to build. It was difficult. I grappled with the decision, especially knowing her personal situation. She was a new mother, her husband had recently been fired, and her mother had been diagnosed with cancer. However, as a leader, I had to consider the business as a whole, not just one individual.

That experience taught me that leadership isn’t just about giving people chances—it’s about setting boundaries, being clear about expectations, and making tough decisions when necessary. I still root for her. But I also learned that protecting the well-being of the team is part of my responsibility, too.

Melody Stevens, Owner, Design On A Dime Interiors

Clear Technical Criteria Prevent Future Issues

I remember the time I had to let an employee go who was very nice but unfortunately just did not perform or meet expectations.

He was constantly making significant mistakes that were not only inefficient for the team but ultimately very costly to the company. Other team members picked up the slack, and that isn’t fair.

I took the initial steps, such as more training, clear guidance, and regular reminders, but I lowered the expectations in advance. After several months, specific benchmarks were established to measure improvement. However, many months later, no progress had been made.

That final conversation was one of the hardest I have ever had. I was clear in my mind about my decision, but I did not want to accept it. I felt horrific knowing beforehand how reliant they were on their earnings, but the consequences were greatly hurting the team.

I learned that being a good leader sometimes means making choices that feel bad but are right for everyone. I made sure to:

1. Be honest – but kind.

2. Clarify just why this was happening.

3. Give them time to gather their things.

4. Help them with the next steps like job references where I could.

This taught me that leadership is not just about being nice; it is about doing what is best for the whole team, even when it hurts. Good leaders sometimes have to make hard choices that keep the team strong.

The most important thing I learned is: Be clear and fair with people from the very beginning about what you expect from them.

Nathan Fowler, CEO | Founder, Quantum Jobs USA

Balancing Empathy and Accountability

During my time as Technical Lead at Ring (SQUAD), I faced a challenging situation with a senior engineer who consistently struggled to adapt to our microservices architecture transition. Despite providing additional training, pair programming sessions, and reducing their workload to focus on learning, their performance continued to impact critical deadlines for our high-load video streaming system.

After three months of documented coaching and support, I had to make the difficult decision to let them go. I first consulted with HR to ensure compliance with company policies and gathered concrete examples of performance issues. Then I held a direct but compassionate conversation, focusing on the specific technical requirements that weren’t being met rather than personal shortcomings.

This experience taught me several valuable leadership lessons. First, the importance of establishing clear technical expectations and evaluation criteria early on. Second, that documenting both support efforts and performance issues is crucial. Most importantly, I learned that prolonging an inevitable separation can damage team morale and project timelines – the rest of the team had been covering for this engineer’s gaps, creating unsustainable pressure.

Following this experience, I implemented more thorough technical assessments during our hiring process and created a more structured onboarding program for engineers joining teams working with unfamiliar technologies. This significantly reduced similar issues in future teams I’ve led.

Serhii Mariiekha, Principal Software Engineer