⚙️ Ops Playbook #63

In a perfect world for operators, you’ll never have to deal with management problems from your team. But since we’re in a not-so perfect world, you’ll need to prepare yourself for a few tough scenarios.

Here’s what we have this week:

• Dealing With Difficult Colleagues → Making sure that everyone’s comfortable inside the office

• Stopping Ageism With Cross-Generational Project Pairing → How to bridge the gap between Boomers to Gen Z, and everyone in between.

• When To Fire Someone → Knowing when enough is enough

Ready? Let’s dive in 👇

P.S. No one wants to build solo. Let’s connect

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Operator’s Library

• Master the Art of Staying Calm Around Difficult People(Psychology Today)

• Avoid Age Clashes at Work (Join The Collective)

• Want a Thriving Team? Stop Ignoring Generational Differences (Paycor)

• Build a Dream Team That Actually Gets Results (Asana)

• Why Hiring Your Opposite Could Be Your Biggest Strength (The Times)

I. Dealing With Difficult Colleagues

Insight from Lenny

Feeling tension in your office? Maybe there’s a weird vibe lingering around the coffee machine, or someone’s "urgent" emails are becoming less like requests and more like demands. 

Whatever the case, it’s time to nip that in the bud and deal with those workplace conflicts head-on. Because if you don't, you're looking at:

• Decreased productivity (No one thrives in a toxic workplace)

• Unhappy employees (They’ll start "quiet quitting" before you know it)

• Potential legal drama (Yikes)

Of course, offices with tons of difficult colleagues are just chaotic. It’s not good for business and for everyone else.

The first step in dealing with them is… finding if there are difficult employees in the first place. Sometimes, a little misunderstanding doesn’t always mean an employee is difficult. So I’ve found it best to do a thorough assessment first.

Not all difficult employees are the same. Some are obvious, while others fly under the radar with their passive-aggressive emails and "accidentally" missed meetings. Let me break down the usual suspects:

1. Chronic Complainers

• Acknowledge their concerns to avoid sounding dismissive.

• Reframe the conversation towards solutions, not problems.

• Encourage them to suggest alternatives—they might surprise you!

2. Change-Resisters

• Explain the “Why” behind the change and its benefits.

• Provide the necessary training and support.

• Empower them to offer feedback and constructive criticism.

3. Aggressors

• Stay calm and set firm boundaries.

• Address the behavior without making it personal.

• Offer alternatives to their confrontational style.

4. Poor Communicators

• Practice active listening and model good communication.

• Offer constructive feedback and training to improve their skills.

You get the idea. These people aren’t just annoying—they’re productivity kryptonite.

Once you’ve spotted the problem, it’s time to do something about it. Here’s a simple action plan:

1. Gather Intel Like a Detective
   Sit down with everyone involved and get their perspectives. It’s like piecing together a workplace mystery—what’s the root cause? And how is it affecting the team?

2. Clarify Expectations
   Be crystal clear about what needs to change. If they nod in agreement, even begrudgingly, that’s progress! And as the saying goes, there’s no point beating a dead horse.

3. Outline Consequences (The Fun Part)
   Let them know the stakes if things don’t change. Acknowledge their perspectives, but make it clear that resolution isn’t optional.

4. Create a Plan
   Define specific steps, assign responsibilities, and set deadlines. Treat it like a GPS for getting your team back on track.

5. Monitor Progress & Adjust
   This isn’t a "set it and forget it" situation. Keep tabs and tweak the approach if needed.

Why spend your day playing firefighter when you can prevent the sparks in the first place? Start by building solid communication channels and checking in regularly. Set crystal-clear expectations and goals for the team, so no one’s guessing at what “good work” means. 

And don’t forget to dish out some recognition when they hit the mark—positive reinforcement isn’t just for dogs; it’s for keeping humans motivated, too.

Creating a positive work environment is key. Make respect and inclusivity non-negotiable. Get the team bonding with some good old-fashioned team-building activities (even if it’s just a pizza lunch or a trivia game). 

Celebrate the wins, big or small, and don’t let conflicts linger. The goal is to catch issues early, keep morale high, and foster a workplace that runs smoothly without constant drama.

II. Stopping ageism with cross-generational project pairing

Insight from Catalyst.

Picture this: five generations sharing the same break room, each bringing their quirks, ideals, and wildly different opinions on coffee temperature. 

It sounds like the setup for a sitcom, right? But nope, it’s the reality of today's workplace. And in 2025, offices are still going to be thriving with people from different generations Most are still Millennials, but you’ll still need to prepare for Gen Z’ers, X’ers, and Boomers.

Let's introduce our cast of characters:

• The Baby Boomers
  Born 1944–1960, Boomers are the original workaholics, fans of face-to-face chats, and masters of the 9-to-5 grind (avoiding TikTok confusion).

• Generation X (The Lost Generation)
  Born 1961–1980, these “latchkey kids” pioneered work-life balance, are fiercely independent, and clock out without guilt.

• Millennials
  Born 1981–2000, Millennials, the largest workforce group, are tech-driven and purpose-focused, sparking endless discussions on workplace culture.

• Generation Z
  Born 2001 onward, Gen Z is entering the workplace, primed to shake up norms even more than Millennials.

These not-so-minor differences lead to ageism that hampers team morale and growth potential. I’ve found that the best way to settle these differences is with cross-generational project pairing.

This goes beyond casual mentoring—it’s about working together, where knowledge from experience meets tech-savviness or fresh perspectives. Here’s how to set it up:

1. Select Projects with defined start and end dates. Choose a project that won’t drag on forever but still has enough complexity to foster real collaboration, like a quarterly report or a client presentation.

2. Assign cross-generational pairs. Create pairs that allow skills to complement each other, like pairing a seasoned team member who prefers old tried and tested ways with a tech-savvy younger employee who likes trying the latest AI tools..

3. Schedule midpoint check-ins: Plan one or two midpoint check-ins so you can gauge their progress and get feedback on what’s working (and what isn’t). Use this time to refine pairings if needed.

The two biggest problems for multi-generational workforces are communication barriers and trust. Cross-generational pairings are great for helping these different generations understand each other’s workflow.

No more grumbling about “kids these days” or “old-school habits.” Pairing up might lead to a few chuckles, but it’s a crash course in real-world skills sharing. Your team will be swapping wisdom and TikTok tips before you know it!"

III. When To Fire Someone

Insight from HBR

Firing someone is like trying to do surgery with a butter knife. It’s not just uncomfortable; it’s clumsy, painful, and often leaves a mess behind. You’re not just ending a job; you’re cutting through egos, ambitions, and even someone’s sense of stability. 

Believe it or not, the toughest part isn’t always “the talk.” It’s usually figuring out whether someone or not should be terminated in the first place.

So, I’m going to give you a little checklist of things to look for when thinking about terminating a problematic employee.

They’re a Chronic ‘No-Show’

You know who’s good at making excuses? Employees who think showing up is optional. If someone is regularly late or missing work without a legitimate reason, it’s not a one-time thing, it’s a pattern. 

Start tracking attendance. If they’re racking up “sick days” like it’s their job, it’s time to have a serious talk.

They’re Not Learning From Mistakes

Everyone messes up sometimes—that’s part of growing. But if an employee consistently makes the same mistakes and refuses to adapt, that’s a huge red flag.
Review past feedback. If they’ve been coached on something multiple times and you’re still seeing the same errors, it’s not a training issue, it’s a commitment issue.

Their Work Is A Hot Mess

We get it, not everyone’s a perfectionist. But if their work is consistently subpar, behind deadlines, and requires constant rework, that’s a productivity killer. 

If their work is a collection of missed deadlines and “just barely good enough” results, you need to ask yourself if they’re bringing value to the team.

They’re Draining the Team’s Energy

Toxic behavior spreads faster than a cold in an office. If an employee is constantly bringing negativity, bad attitudes, or gossip to the workplace, it affects morale

Check-in with other team members. If you notice others starting to avoid this person or showing signs of burnout, it’s a sign that the energy vampire in your team might need to go.

They’re Always Passing the Blame

Accountability is key. If someone’s always shifting blame or avoiding responsibility, they’re not going to grow or improve.

Look for patterns of behavior. If you notice them blaming others or deflecting accountability in meetings or in their work, it’s time to confront the issue head-on.

You’ve Already Given Them Multiple Chances

If you’ve had the same conversation about performance or behavior several times with no improvement, the situation is probably not going to get better without a major shake-up. 

Look back at their performance reviews and your past feedback. If you’ve documented multiple issues with no significant changes, it's time to make the tough call.

Letting someone go isn’t fun, but with a little empathy, clear expectations, and some proactive management, you can handle it without looking like a villain. Remember:

• Address problems early—don’t wait for a catastrophe.

• Don’t hide behind HR like a middle schooler passing notes in class.

• Stay human, even when delivering tough news.

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