The 5 Most Difficult Employees (And How To Actually Handle Them)

What to say and do as a leader, without losing your mind

👋 Howdy! Claire here, Founder & CEO of Canopy. Welcome to my weekly newsletter on leadership, “Views from the Canopy”. If you’ve been enjoying my writing (and illustrations!) recently here, do please make sure you’re subscribed so you can receive a fresh piece each week, and consider sharing with a friend or colleague who you think might enjoy as well.

Now, onto this doozy of a piece: A guide to difficult employees…

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“What in the world is happening here?

I remember the words running through my mind, almost a decade ago. A team member sat across from me, masterfully spinning a web of excuses about missed deadlines while I wrestled with a crucial question: How do you coach someone to success when they won't even acknowledge reality?

Luckily, I kept my cool. I stayed steady and calmly explained where I thought there was a gap between expectation and performance and what they could do better. They relented, and we were able to find a way to move forward, at least in that moment.

Eventually, we parted ways, perhaps to no surprise. But since then, it got me thinking: How as leaders can we handle the inevitably challenging employees we encounter?

Is there a way to approach the situation and positively coach difficult employees? Or is it lost to the wind and irrecoverable?

In working with thousands of leaders over the past decade, I’ve discovered patterns. You can indeed help bend the arc of performance to be positive — but only if you understand the pattern’s root basis, and how to respond effectively.

Here are the five most challenging employee archetypes I've encountered, and the specific strategies that can help you lead them successfully...

Archetype #1: The Entitled Veteran

Meet the cultural cornerstone of your company – the person who remembers when the office was just one room rather than an entire building, and when original logo for the company was sketched out on a napkin. They carry invaluable institutional knowledge and deep relationships across the organization. They're often beloved, respected... and they know it.

But here's the challenge: This veteran status has morphed from an asset into a shield against change. When new initiatives roll out, you might hear them say something like: "Back when I was employee number 4, we just didn't do things that way. I don't know if that's what our company should be now..."

Their resistance isn't just personal stubbornness — it can ripple through the organization, swaying newer team members and quietly undermining important transitions. Their institutional influence makes this particularly tricky to navigate.

Here’s the key to understanding the Veteran mindset:

• Identity investment: Their long tenure isn't just about time served – it's core to their identity. When you challenge "how things are done," they feel you're challenging who they are.

• Memory as authority: They've seen initiatives come and go, leaders arrive and depart. This history becomes their source of power, leading them to view their experience as superior to current leadership directives.

• Loss aversion: Change threatens their status as the "keeper of culture." Their resistance often stems from fear of losing their unique value to the organization.

• Selective memory: They tend to romanticize the past ("when things were simpler/better"), forgetting the challenges and messiness of earlier days.

This means your task isn't just about managing their performance — it's about helping them find their place in the company's evolution without losing their sense of value and identity.

Here are the specific steps you can take as a leader:

1. Ground conversations in present reality. “I value your experience with our history, and I'd like us to focus on our current reality. What specific concerns do you have about this new direction?"

2. Create inclusive accountability. "While we've all been here for different lengths of time, these new standards apply to everyone equally – from our newest hire to our most seasoned veteran."

3. Connect past and present. Instead of dismissing their experience, help them see how their knowledge can actually support the change: "Your deep understanding of our core values could really help us implement this change in a way that stays true to who we are."

4. Be clear about role requirements. "This role now requires [specific new expectation]. This isn't optional – it's a core requirement for everyone in this position."

When do you reach the upper limit, and consider parting ways?

• Ask yourself: Is their behavior changing in a way that positively affects the team? Or it is net-neutral or even outright negative?

• Remember: Their cultural weight does NOT give them permission to override your actions and efforts as a leader. You don’t want the old corrosive culture of the past to subvert the new positive culture of the present.

Archetype #2: The Passive Resister

Picture this: You're in a meeting and your team member is nodding enthusiastically. "Yes, absolutely, I'm on board!" they say with conviction. Fast forward a week, and the work isn't done. Or worse, it's done poorly with a fresh set of excuses. This is the Passive Resister, the master of cheerful agreement followed by quiet inaction.

What makes this behavior particularly frustrating is its elusiveness. Unlike open resistance, which you can address head-on, this pattern of agree-and-avoid creates a maddening cycle of apparent commitment followed by mysterious under-delivery.

Here’s the key to understanding the Passive Resister:

• Success through avoidance: Their strategy has served them well, so far. By agreeing in the moment and failing quietly later, they've learned to dodge both confrontation and consequences.

• The accountability gap: Each missed deadline or subpar deliverable gets lost in a fog of vague explanations and renewed promises, making it hard to pin down the pattern.

• The time advantage: By the time you realize there's an issue, the moment for immediate correction has passed, creating a cycle of delayed feedback and response.

Here are actions you can take as a leader to break the cycle:

1. Create clear checkpoints."Let's break this down into specific milestones. I'd like to see a draft by Wednesday and get an update in our Monday meeting. How does that sound?"

2. Document agreements in real-time."I'm noting down what we've agreed to. I'll send a quick email after this meeting so we both have the same reference point."

3. Address patterns, not incidents."I've noticed a pattern where we agree on deadlines, but the work consistently comes in late. What obstacles are you encountering that we haven't discussed?"

4. Set explicit consequences."If we continue to miss these deadlines, it will impact your performance evaluation and our ability to assign you to key projects. What support do you need to meet these timelines?"

How do you know when it’s time to move on?

• Give them one clear chance with a specific timeline: "Over the next 30 days, I need to see these three specific improvements..."

• If after implementing clear checkpoints and consequences, you're still having the same conversations about missed deadlines and unfulfilled commitments, it's time to acknowledge that the pattern isn't changing.

• Remember: Each cycle of agree-and-avoid doesn't just impact deliverables — it erodes team trust and sets a precedent that commitments are optional.

Archetype #3: The Brilliant Aggressor

Every organization knows this person: The technical genius whose brilliance is matched only by their ability to leave emotional wreckage in their wake. They consistently deliver exceptional results while creating a wake of demoralized colleagues and fractured team dynamics. Their technical work may be elegant, but their communication is anything but.

You might hear them say something like: "Look, I don't have time to hold everyone's hand. If people can't keep up or handle direct feedback, maybe they shouldn't be here. I'm just focused on getting results."

Here’s the key to understanding the Brilliant Aggressor:

• Success as validation: Their exceptional results have created a self-reinforcing belief that their aggressive approach is not just acceptable, but necessary for excellence.

• Learned behavior: Years of implicit rewards (promotions, praise, special treatment) have taught them that interpersonal costs are acceptable collateral damage for high performance.

• Superiority complex: They genuinely believe their technical excellence gives them license to bypass social norms and professional courtesies.

• Efficiency obsession: They view interpersonal niceties as inefficient obstacles to getting work done, rather than crucial elements of sustainable team performance.

Here’s the action you can take as a leader to address this:

1. Connect behavior to business impact."When you dismiss others' ideas in meetings, it doesn't just hurt feelings — it means we're missing insights that could make your solutions even better. We're actually losing efficiency."

2. Quantify the hidden costs."Your technical solutions save us 20 hours a week, but we're spending 15 hours managing team conflicts and rebuilding confidence. Let's talk about how to maintain your high standards while lifting the team up."

3. Create clear behavioral expectations."I need you to do three things: wait 10 seconds before responding to ideas in meetings, acknowledge one positive aspect before critiquing, and raise concerns privately first. Can you commit to trying these for the next two weeks?"

4. Leverage their logic."If you could improve team performance by 30% by making a few behavioral adjustments, wouldn't that be worth it? Let's approach this like any other optimization problem."

You may also find it helpful to set boundaries as a leaders in these ways:

• Document impact. Keep specific examples of both their technical contributions and the interpersonal incidents that undermine team effectiveness.

• Create measurement systems. "We'll be evaluating success not just on technical metrics, but also on team health indicators like collaboration scores and peer feedback."

• Define clear consequences."Continued interpersonal issues will affect your growth opportunities here, regardless of technical performance. Here's specifically what needs to change..."

When is it time to part ways?

After implementing these strategies, evaluate these critical questions:

• Have they shown genuine interest in modifying their behavior, beyond surface-level compliance?

• Has the ratio of their positive impact to team damage improved meaningfully?

• Is the emotional toll on the team worth the technical output?

• Are you seeing sustained behavior change or just temporary adjustments?

Remember: Technical skills can be rehired for, but a poisoned team culture can take years to rebuild. If this person show no real commitment to change after clear feedback and support, it's better to part ways sooner rather than later.

Archetype #4: The Perpetual Victim

There's a pattern you start to notice: Every missed deadline has an elaborate backstory. Every piece of feedback triggers a cascade of explanations about why others are to blame. At first, some explanations seem legitimate – after all, we all face obstacles. But soon you realize that this person has mastered the art of dodging responsibility through an endless series of justifications and deflections.

You might hear them say: "I really tried my best, but Marketing didn't give me what I needed, and then Sarah was late with her part, and the client kept changing requirements, and honestly, I feel like I'm being singled out unfairly here..."

Here’s what to understand about the Victim mindset:

• External locus of control: They genuinely believe their success or failure lies completely outside their control, making them feel powerless and defensive.

• Pattern of self-protection: Victimhood has become their shield against criticism and their escape route from accountability.

• Confirmation bias: They actively collect evidence that supports their narrative of being unfairly treated or blocked by others.

• Fear of inadequacy: Often, beneath the excuses lies a deep fear of not being good enough, making it safer to blame others than risk taking full responsibility.

Here are the key leadership actions you can take:

1. Create objective benchmarks."Let's look specifically at what's expected in this role. Here are the measurable standards everyone on the team needs to meet..."

2. Focus on future solutions."Rather than discuss why this happened, let's focus on what you need to deliver different results next time. What specific actions can you take?"

3. Document facts, not stories."I'm noting that the project was delivered three days late. What specific actions will you take to meet our next deadline?"

4. Redirect to personal agency."I hear several external challenges. Of those factors, which ones can you influence or control?"

You may need to also set boundaries with them:

• Break the excuse cycle. Acknowledge their perspective briefly: "I understand there were challenges..." Then immediately pivot to accountability: "However, managing these challenges is part of the role."

• Create clear paper trails. This includes documenting agreements and deadlines in writing, following-up on verbal conversations with email summaries, and tracking patterns of explanations and missed commitments

• Establish consequence outcomes."If we continue to miss deadlines, regardless of the reasons, here's what will happen next..."

When is it time to go in different directions?

Monitor these key indicators:

• After establishing clear expectations, do they still default to elaborate explanations?

• Has their language shifted from "why I couldn't" to "how I will"?

• Are they beginning to take ownership of outcomes, even partially?

• Is their behavior affecting team morale or creating additional work for others?

Then, be on the lookout for these red flags that signal it’s time to move on:

• They begin creating preemptive excuses before projects even start.

• Other team members are increasingly hesitant to work with them.

• They react to support and solutions with more victimhood narratives.

• The energy spent managing their narratives exceeds the value they create.

Remember: Your role is to manage performance, not provide therapy. While you can support someone in developing a more empowered mindset, you can't force them to take responsibility if they're committed to their victim narrative.

Archetype #5: The Performance Rollercoaster

One week they're your star performer, delivering work that exceeds all expectations. The next week, they're missing basic deadlines and making elementary mistakes. Their emotional state seems to swing just as dramatically — from euphoric enthusiasm to tearful overwhelm. This unpredictability keeps both you and the team constantly off balance, never knowing which version of the person you'll encounter each day.

You might hear them say: "I know I crushed that project last week... I just... I don't know what happened this time. I'm so sorry [fighting back tears]. I promise I'll do better — I'll stay late, work weekends, whatever it takes..."

Here’s the key to understanding the Rollercoaster:

• Pattern blindness: They often can't see their own performance swings, experiencing each high and low as an isolated incident rather than part of a larger pattern.

• Emotional amplification: Their self-assessment tends to magnify both successes ("I'm incredible!") and failures ("I'm terrible at everything"), with little middle ground.

• Crisis-driven performance: They often need emotional intensity to perform at their peak, making sustainable consistency difficult.

• Validation dependency: Their self-worth is deeply tied to their most recent performance, creating an exhausting emotional pendulum.

Here are the specific steps you can take as a leader:

1. Create visibility around patterns."Let's look at your last six projects together. Notice how the quality varies? I want to understand what's different between your high and low periods."

2. Establish baseline standards."We need to define what 'good enough' looks like. Not every project needs to be exceptional, but they all need to meet these basic requirements..."

3. Build performance guardrails."Let's create a checklist for each project type. This gives you a concrete way to verify quality before submission, regardless of how you're feeling."

4. Address emotional management."Being passionate about your work is valuable, but emotional stability is also a core job requirement. How can we help you find a more sustainable balance?"

You may also want to set boundaries with this person:

• Create consistent check-ins. Schedule regular brief check-ins to catch issues early. Use these meetings to calibrate their self-assessment with reality. Focus on concrete deliverables rather than emotional states

• Define success metrics clearly."Success looks like meeting these five specific criteria consistently, not occasionally exceeding them while missing basics other times."

• Document performance patterns. Track both the highs and lows. Note any external factors that might correlate with performance swings. Include emotional impacts on team dynamics

When is time to part ways?

Evaluate these key factors:

• After implementing structure and support, has the performance variance decreased?

• Are they developing better emotional self-regulation in professional contexts?

• Is the team's productivity being significantly impacted by the unpredictability?

• Do the exceptional periods justify the resources required to manage the low periods?

These signs will tell you, in particular, that it’s time to move on:

• The emotional volatility is spreading to other team members.

• Their inconsistency is creating unsustainable backup work for others.

• Despite support and feedback, the pattern remains unchanged or worsens.

• The emotional labor required to manage them exceeds their contribution.

Remember: While everyone has better and worse days, a baseline of consistency is necessary for team function. Your role is to support growth while protecting team stability — sometimes that means making the difficult decision to part ways.

The most important question to ask

Whether you're dealing with one of these challenging archetypes or managing a blend of several, the most crucial question isn't just "Should they stay or go?" but rather:

“What’s in the best service of the team?

This question helps cut through the complexity. You don’t need to make a pro’s and con’s list. Instead, ask yourself, “What’s in the best service of the team?” and focus on three key considerations:

Impact assessment

• How much energy are you and your team spending managing this situation?

• Is this taking attention away from other team members who could be flourishing with more support?

• Are you seeing meaningful progress, or just temporary improvements followed by regression?

Resource Reality

Every leader has limited time and emotional bandwidth. Sometimes the kindest thing – for yourself, your team, and even the challenging employee – is to acknowledge that the current situation isn't working for anyone.

Growth Potential

• Has the employee shown genuine recognition of the issue?

• Are they actively participating in solution-finding, or merely reacting to feedback?

• Do they demonstrate the capacity and willingness to change?

Answering these questions will give you a truthful answer.

Give yourself permission to make the decision

If you’re like me, you resent this part of leadership. It’s excruciatingly hard. But it’s hard for all of us. Know that you’re not alone in finding these situations daunting — and every experienced leader has faced similar moments of uncertainty.

Take this writing here as a permission slip — whatever permission you need. Perhaps it's permission to make one final, structured attempt at turning things around. Or maybe it's permission to acknowledge that you've given it your best effort, and it's time to make a change.

Most importantly, know that being thoughtful about these decisions, and that feeling the weight and agony of them doesn't make you a weak leader. It makes you a conscientious one. The key is not to let that conscientiousness paralyze you from making necessary changes.

Your team is watching and waiting for your leadership. They may not know all the details, but they know when something isn't working. Taking action, whether it's a final committed attempt at improvement or a decision to part ways, shows them that you're committed to maintaining a healthy, high-performing team culture.

The path forward starts with your next step. What will it be?

-Claire

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Eager for more helpful tactics like this, from me, Claire, CEO at Canopy? Here are ways we can work directly together:

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

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