From Fun Friend to Responsible Colleague: The Leadership Challenge

Someone can be great fun to hang out with – but give you a real headache when working together.

I once had an employee like that.
He was creative, well-trained in communications, tall, and looked great on camera. In social life, everyone liked him – cheerful, charismatic, full of energy.

But at work, that charm came with gaps that were hard to ignore: often arriving at the office at 10 AM, joining team meetings only online, sometimes forgetting tasks, and even letting a contract sit for 3 months before asking me to backdate the signature.

At first, I tried to give subtle, gentle feedback. It didn’t work. And I realized it was time for a difficult conversation.

👉 I laid out the facts – pointing to specific incidents.
👉 I showed the impact – how those behaviors hurt team morale and effectiveness.
👉 I listened, without arguing.
👉 Finally, I set boundaries: 30 days to improve, followed by a check-in.

✨ My takeaways:

For leaders: Don’t shy away from setting boundaries and having difficult conversations. Being direct, respectful, and consistent is what helps employees grow and keeps the team on track.

For young professionals: Skills alone aren’t enough. Work attitude, accountability, and discipline are what earn you trust – and trust is the greatest capital for your career.

❓If it were you, would you stay patient… or set clear boundaries?