Navigating the workplace often means dealing with challenging personalities. From the constant complainer to the drama enthusiast, the micromanaging boss, or the colleague who seems determined to sabotage everything. Learning to handle tricky situations (and individuals) is vital for everyone to master. But especially for managers and mentors.

Mentors and Managers have an opportunity to do more than master these skills for themselves. They can also guide others in building skills to cope with difficult situations and people. This guide will help you become calm and collected in difficult situations, but it will also help you consider how to mentor others to learn these skills.

With the right approach, you can transform even the most challenging interactions into opportunities for growth. Let's break down the types of Defining Characteristics to discover personal and professional development potential.

Step 1: Assess the Situation—Person, Problem, or Situational?

What to do when confronted with someone who is behaving badly? Before diving into problem-solving, take a step back. The real issue may not be the person but the situation or the dynamics at play. Savvy managers know identifying the root cause is key to addressing the issue.

Seek first to understand: Consider what you are observing.  

Is someone coming to you with a complaint?

Are your requests being questioned?

Do meetings seem harder or more frustrating than they used to be?

Reflect the source of the issue: What kind of problem is it?

• Is it the person?

  • Do they display challenging behavior consistently or just in certain situations?

• Is it the situation?

  • Are unclear expectations, deadlines, or stressors fueling their actions?

• Is it the dynamics?

  • Could unresolved conflicts or power struggles be creating tension?

If you need more clarification, ask simple questions to find out. You can start by stating the situation you have observed and letting them know you are trying to understand it better. Speak calmly and without judgment. Doing so can help you get honest answers.

Use information-gathering questions like:

• What do you think is the biggest obstacle here?

• How can we better align our goals?

• What support would help make this easier for you?

• Can you share what your concern is?

• What are you thinking/feeling that makes you upset about the situation?

Step 2: Meet the Magnificent Five - Difficult Personalities and How to Handle Them

The Criticizer

Defining Characteristics: Loves pointing out flaws but rarely offers solutions.

How to Handle:

• Validate their input but steer the conversation toward actionable ideas.

• Redirect their focus: *"What would you recommend as an improvement?"

Pro Tip: Criticizers often want to be heard. Show them their opinions matter, and they might soften.

What Your Mentees Should Know:

• Not all criticism is personal. Teach them to separate the message from the delivery.  

• Encourage them to respond with curiosity: “Can you clarify what you’d like to see improved?”  

The Aggressor

Defining Characteristics: Pushy is loud and loves a good argument.

How to Handle:

• Stay calm and refuse to escalate.

• Set boundaries if their behavior becomes unprofessional.

• Use neutral phrasing like: "Let's focus on how we can work together on this."

Pro Tip: Aggressors often want control. Help them channel their energy into productive collaboration.

What Your Mentees Should Know:

• Aggressors often act out of frustration or fear of losing control.  

• Equip mentees with assertive responses, like: “Let’s focus on solutions instead of blame.

The Drama Magnet

Defining Characteristics: Turns every small issue into a five-alarm fire.

How to Handle:

• Avoid feeding the drama; stick to the facts.

• Limit how much time you spend in their emotional whirlwind.

• Redirect their attention: "What steps can we take to resolve this?"

Pro Tip: Empathy with boundaries works best. Acknowledges their feelings but keeps the focus on solutions.

What Your Mentees Should Know:

• Drama Magnets may not intend harm but can derail productivity.  

• Encourage mentees to stay grounded and focus on the solution, not the drama.

The Toxic Personality

Defining Characteristics: Constant negativity that drains the team's energy.

How to Handle:  

• Reinforce positivity by highlighting small wins.

• Limit exposure to their negativity without isolating them.

• Challenge their complaints with solutions: *"What's one thing we can do to make this better?"

Pro Tip: Toxic individuals often feel powerless. Involve them in solutions to shift their focus.

What Your Mentees Should Know:

• Toxic individuals often feel powerless. Help your mentees to not counter toxic with their own toxic energy.

• Teach them to disengage from unproductive negativity while remaining professional.  

The Assassin

Defining Characteristics: Sabotages others behind the scenes to advance their agenda.

How to Handle:

• Build transparency into processes to limit their influence.

• Document everything and maintain professionalism.

• Strengthen team cohesion to counteract their divisive tactics.

Pro Tip: Assassins are often insecure. They ping them to feel valued, which can reduce their destructive tendencies.

What Your Mentees Should Know

• Assassins thrive in ambiguity. Encourage mentees to maintain professionalism but dare to call out bullies.

• Remind them that strong relationships and clear communication can counteract sabotage.  

Step 3: Beyond the Difficulty — Motivations Matter

Difficult behavior usually stems from unmet needs, frustrations, or insecurities. Instead of jumping to conclusions, it's crucial to get curious and understand their motivations:

• Ask about their goals: "What does success look like for you here?"*

• Understand their concerns: "What's holding you back from feeling confident about this?"

• Reframe their behavior: Criticism or control might be a cry for clarity or recognition.

Understanding their motivations allows you to tailor your responses and turn conflict into collaboration.

Step 4: When the Problem Is Bigger Than the Person

Sometimes, the real challenge isn't just the individual—it's the situation or dynamics around them. In that case, you will need to take action to resolve the information, expectations, processes, or solutions to resolve the underlying issue.

Unclear Expectations

• Clarify roles, goals, and deadlines.

• Use feedback loops to ensure alignment.

• Ask: *"Can you walk me through how you approach this task?"*

Overloaded Workloads

• Assess workload by having the person document what they are doing and estimating how long it takes to do each task

• Reprioritize and redistribute tasks.

• Ask: "What's taking the most time, and how can we adjust?".

Dysfunctional Communication

• Set clear norms, like regular check-ins or structured meeting agendas.

• Create space for feedback and follow up on agreed actions

• Ask: "What's one way we can improve our communication?"

Broken Processes

• Look for inefficient workflows

• Bad policies or procedures

• Poor alignment with other roles or departments

If all else fails, you may need a workshop to work out how to fix the problem as a team. Get started with my free Workshop eBook.

Step 5: Special Case—When Their Manager Is the Problem

Sometimes, you are not the direct manager. In matrix organizations, this is often the case. You may wonder: can I help? Yes, you can. Helping others manage upward is a key skill you can share with your mentees.

Understand Their Experience: Role model listening to understand the mentees point of view first.

Ask: "What's been challenging in your relationship with [manager]?"

Coach on Communication: Teach them neutral, solutions-focused language.

Ask: What do you think is [manager's] biggest concern?

Role play problem solving with empathy: Reverse the roles.

Ask: "Can we reverse roles? Can you put yourself in your mangers shoes and let’s try to resolve the issue."

Managing difficult people doesn’t have to be overwhelming. By focusing on these four key principles, you can navigate challenges with confidence and clarity. And help you mentees and teams to do the same. Read these articles next if Culture or the the Organizational Framework is part of the problem. And if you want to know more about how to mentor for success, get my ebook here.

And a Final Tip for Mentors

Teach your mentees that difficult people are part of every workplace, but how they respond defines their growth. By equipping them with empathy, assertiveness, and problem-solving skills, you’ll help them navigate challenges and emerge as stronger, more capable professionals.