101 Tough Conversations to Have with Employees: A Review

Summary

101 Tough Conversations to Have with Employees is a manager’s step-by-step guide to framing and leading conversations with employees that could otherwise easily lead to a communication breakdown or hurt feelings. Scenarios include:

• Navigating Employee Underperformance

• Navigating Compensation Conflicts

• Navigating Employee Terminations

The book is designed so that readers can simply flip to the most relevant scenario as needed (vs. reading the book in its entirety).

My Thoughts

1. I read through the book, selected a few of the toughest scenarios, and then requested guidance from ChatGPT. ChatGPT provided a more considered and thorough response every time.

2.  There were multiple patterns in the book that I found questionable, including:

   1. For every disagreement within the book, the conversation assumes that both parties are always at fault, regardless of the facts. This is a quick way to alienate your employees.

   2. In every scenario where the employee has done wrong, the author implies that the very act of calling out poor behavior will always lead to the employee immediately conceding.  This is very unrealistic.

   3. The author advocates multiple times for the manager to say the words “I’m sorry,” regardless of whether they actually did something wrong. This advice is given despite the author also indicating repeatedly that managers should prioritize the legal protection of their organization. This is problematic because, depending on the territory, an apology may be used as evidence in court of an admission of legal liability.

   4. The author explicitly states that the manager’s best tool is guilt.  Philosophically, I believe this promotes a framework of the employee as an adversary to leverage and exploit.  

Final Thought and Recommendation

It’s naive to assume that all employees are good actors who are self-aware and care about doing their job well, but I believe that consistently following this book’s advice may lead to low-trust teams that suffer from long-term low morale, low retention, and ultimately low productivity. 

If you want guidance for navigating a tough conversation with an employee, I recommend:

1. ask your manager for advice, and/or 

2. use ChatGPT (and ask it to include guidance to navigate counter-arguments or other pushback)