#42 Blog. "Oh Sh*t" Moments in Management – And How to Handle Them Like a Pro

As a manager, you’ve got the title, the responsibility, and- let’s be real- a whole new level of stress. No one tells you about the moments when you’ll sit at your desk, staring at your screen, thinking, “Oh sht, what do I do now?”.

Management isn’t just about running meetings and making decisions. It’s about navigating the tough, messy, and unexpected challenges that come with leading people.

Over the years, working 1:1 with leaders and facilitating leadership workshops, I’ve seen the same “oh sh*t” moments come up again and again. Here are some of the most common ones with ways to tackle them.

“My Team is Burnt Out & Checking Out"

People on your team are disengaged, missing deadlines, and the energy in meetings is dead (and there is always one missing at least).

X What Not to Do:

• Assume they’re lazy.

• Throw a pizza party to “boost morale” without addressing the real issue.

✅ What to Do Instead:

• Diagnose the root cause – Is it overwork? Lack of clarity? No recognition?

• Have 1:1s and ASK: What’s working? What’s frustrating? What do you need from me?

• Prioritize – Cut non-essential tasks, adjust deadlines, and push back if needed.

• Reconnect to the “Why?” – Remind them why their work matters and celebrate small wins.

• Please Please Please- If you’re seeing burnout, don’t wait- do something about it right away.

  
  

"My Best Employee Just Quit… Now What?"

Your top performer walks into your office and drops the bombshell: they’re leaving. Panic sets in.

 X  What Not to Do:

• Beg them to stay.

• Guilt-trip them or make it personal.

• Ignore the impact on the rest of the team.

✅ What to Do Instead:

• Stay professional – Congratulate them, ask about their next step, and keep the conversation positive.

• Get insights – ASK: “What led to this decision?” You might uncover issues affecting others.

• Create a transition plan – Who will take over their responsibilities? What knowledge needs to be transferred?

• Communicate with your team – Acknowledge the departure, address concerns, and reinforce stability.

• Conduct an exit interview to learn from the experiences, sometimes departures highlight issues you can fix before losing more people.

  
  

“I Need to Fire Someone (But I’m freaking out thinking about it)"

A team member isn’t performing, and you’ve tried coaching, but it’s not working.

 X  What Not to Do:

• Delay it forever.

• Make it personal.

• Be vague about why they’re being let go.

✅ What to Do Instead:

• Be direct, but human – “This isn’t working out, and today will be your last day.”

• Prepare – Work with HR, ensure documentation is in order, and have next steps ready.

• Control the narrative – Let the team know without oversharing. “We’re making a change to ensure the right fit for the team.”

• Reflect – What could have been done earlier to address performance issues?

• Firing someone is tough, but keeping the wrong person hurts your whole team. Make the hard call when necessary!

  
  

“I Gave Feedback… and It Backfired"

You tried to give feedback, but the person got defensive, upset, or shut down.

 X  What Not to Do:

• Assume they’re just “bad at taking feedback.”

• Avoid giving feedback altogether.

✅ What to Do Instead:

• Check your approach – Was it clear, specific, and non-judgmental?

• Normalize feedback – Make it regular, not just when things go wrong.

• Acknowledge emotions – “I see this caught you off guard—want to talk through it?”

• Give them time – Some people need to process feedback before responding.

• Feedback should feel like a conversation, not a punishment. The better you get at it, the easier it becomes.

  
  

To Conclude:

Every manager faces “Oh sh*t” moments. The difference between struggling and succeeding isn’t avoiding them- it’s learning how to handle them well.

If you’re feeling overwhelmed, remember:

You’re not supposed to have all the answers.

You’ll make mistakes—own them and learn.

Leading is about growth—yours and your team’s.

So, the next time you face an unexpected management challenge, take a deep breath, lean into the discomfort, and handle it like the leader you are becoming.

Managing for the first time? It’s definitely a challenge—especially when it’s all new! 🙂 Feel free to connect!