Most Challenging Employees
- Salina Salli
- Mar 27
- 4 min read
How leaders can survive without losing your sanity
Managing people is an art, but some employees make it feel like a never-ending circus. Every leader will encounter difficult employees who disrupt productivity and team morale. The key is knowing how to handle them effectively while recognizing when it's time to move on. Here are six common types of difficult employees and how leaders can address them.
1. The “Boss-Backed” Employee
Behaviour:
This employee enjoys special privileges because of their close ties to upper management. They use their connections as a shield, bypassing protocols, ignoring feedback, and expecting special treatment.
Key to Understanding:
They believe their relationship with higher-ups gives them immunity. They may genuinely see themselves as above normal processes and expect others to accommodate them.
Communication Strategies:
Keep conversations factual and professional—avoid emotional arguments.
Reinforce company policies and procedures in discussions.
If they name-drop, redirect the conversation to performance expectations.
Actions as a Leader:
Treat them like any other employee—set clear expectations and hold them accountable.
Focus on performance data and measurable outcomes rather than office politics.
If they try to bypass you, document their behavior and escalate only when necessary.
When It’s Time to Part Ways:
If their presence creates division, disrupts teamwork, or compromises standards, it’s time to have an honest conversation about their role in the team.
2. The Entitled Veteran
Behaviour:
This is the long-serving employee who believes tenure equals privilege. They resist change, dismiss new ideas, and often say, “We’ve always done it this way.”
Key to Understanding:
They may feel insecure about younger employees advancing faster or changing processes that they helped build.
Communication Strategies:
Acknowledge their experience before introducing new ideas.
Use “we” instead of “you” to create a sense of inclusion.
Highlight how changes benefit them, not just the company.
Actions as a Leader:
Show respect for their experience but emphasize the need for growth and adaptability.
Involve them in shaping change rather than forcing it upon them.
Provide opportunities to mentor younger employees, helping them feel valued.
When It’s Time to Part Ways:
If they continuously block progress, refuse to adapt, and create negativity within the team, a serious discussion about alignment with company goals is necessary.
3. The Passive Resister
Behaviour:
They nod in agreement during meetings but drag their feet when it’s time to execute. Their resistance is silent but effective in stalling progress.
Key to Understanding:
They fear accountability and prefer to blend into the background, hoping others will pick up the slack.
Communication Strategies:
Ask open-ended questions to uncover concerns.
Use deadlines and progress updates to ensure follow-through
Avoid vague instructions—be crystal clear
Actions as a Leader:
Set clear, time-bound deliverables with follow-ups.
Use a mix of encouragement and firm accountability to get them moving.
Make them responsible for key tasks so they can’t rely on others to carry them.
When It’s Time to Part Ways:
If their passive resistance starts affecting overall team efficiency and they show no signs of improvement despite coaching, it’s time for a change.
4. The Smart Aggressor
Behaviour:
This employee is highly capable but uses their intelligence to manipulate, intimidate, or take credit for others’ work. They may perform well individually but create a toxic team environment.
Key to Understanding:
They often value personal success over teamwork and may believe their methods are justified if results are achieved.
Communication Strategies:
Keep all communication documented to avoid manipulation.
Challenge them with logic, not emotions.
Reinforce collective success instead of individual victories.
Actions as a Leader:
Encourage collaboration by setting team-based goals.
Address manipulative behavior directly with facts, not emotions.
Reinforce company values of respect and teamwork as non-negotiables.
When It’s Time to Part Ways:
If their behavior starts creating fear, low morale, or high turnover, the cost to the organization outweighs their contributions.
5. The Forever Victim
Behaviour:
This employee always has a reason why things go wrong—blaming colleagues, policies, or bad luck. They rarely take ownership of their mistakes.
Key to Understanding:
They see themselves as helpless in every situation, which can be a coping mechanism to avoid criticism or accountability.
Communication Strategies:
Use solution-focused language: “What can we do next?”
Reinforce personal accountability with “I” statements.
Avoid engaging in pity parties—redirect to actions.
Actions as a Leader:
Shift the focus from problems to solutions by asking, “What can you do differently?”
Encourage ownership by making them responsible for specific deliverables.
Provide coaching on resilience and accountability.
When It’s Time to Part Ways:
If they continue to drain team morale and refuse to take responsibility, their presence may be holding the team back.
6. The Inconsistent Performer
Behaviour:
One day they exceed expectations; the next, they disappear into mediocrity. Their performance is unpredictable, making it difficult for leaders to plan effectively.
Key to Understanding:
Their inconsistency may stem from personal challenges, lack of motivation, or poor time management.
Communication Strategies:
Use regular check-ins to track performance patterns.
Offer clarity on expectations upfront.
Ask for self-assessment to encourage awareness.
Actions as a Leader:
Identify patterns—are they struggling with specific tasks or external issues?
Provide structured feedback and a support system to improve consistency.
Set clear KPIs and track their progress over time.
When It’s Time to Part Ways:
If they fail to stabilize their performance despite coaching and support, they may not be the right fit for the role.
Final Thoughts
Difficult employees are not just workplace challenges—they are leadership tests in disguise. The real goal isn’t to “fix” them but to create a culture where accountability, adaptability, and teamwork thrive. However, when repeated efforts fail, knowing when to let go is just as important as knowing how to manage. After all, strong teams are built on shared values, not just individual talent.
So, which of these difficult employees is secretly running your team instead of you?
With love, Salina Salli
If you’re ready to take back control and develop leadership strategies that actually work, let’s talk! Digital Dolphin Academy specializes in equipping leaders with the skills to handle workplace dynamics with confidence. Reach out at hello@digitaldolphin.one to explore how we can add value to your organization.
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