Whether you succeed or fail in business and in life could be a matter of how you manage difficult conversations-or if you ever have them at all. Difficult conversations at work often include discussing perceived failings of an employee or a vendor or your perceived failings in providing to the customer, to the bank or to your employees. Just working up to these conversations can be the worst part, but avoiding them will undermine your authority.

There are some key ways to make these conversations go as well as they possibly can. Here are some tips:

1. Never have a difficult conversation when emotions are running high on either side. Table them to a scheduled time…

2. Schedule a time and let the person you will be speaking with know the general reason you’d like to talk.

3. Have the conversation in private.

4. Define the intention of the conversation ahead of time. If you have struggled with a vendor or employee, is it to clarify expectations? If this is a second or third conversation around the same topic, does the conversation set establishing a final decision making moment? Decide and make sure you inform the person you will speak with of your intentions.

5. Make compassion and kindness an priority and watch for escalating emotions. If they start to do so, step away and schedule a follow-up conversation. However, intimidation or stonewalling on either side to the point that no conversations are possible means there is a much deeper issue. I recommend Crucial Conversations, Chapter 4 and 5 if this continues to happen.

6. Watch YOURSELF. Are you listening more than you talk?

7. Solicit input from the other party, especially to make sure they don’t feel attacked.

8. Decide ‘next steps’. What will you do going forward? What do you expect from them going forward?

9. Finally, at minimum, schedule a follow-up call or, preferably, in-person discussion in 30-60 days to see how things are going, if both parties are satisfied with the results or to offer feedback on the process.

Difficult conversations are a fact of life and business. Once you master this, you will find that your management skills and reputation have proved significantly. I’d love to hear your stories of your own difficult conversations and how you managed them.


by Steven Schlagel