Business Success Rules 101: Rule #1 – Dealing with Tough Conversations

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Throughout my career I have been in many tough conversations, including the removal of employees for cause, addressing employees for safety violations, removing shareholders who didn’t see eye to eye with the majority of investors, and dealing with the removal of board members for a variety of reasons. Although every one of these situations came down to a decision based on facts compiled over time, it did not take away from the need for a tough and often uncomfortable conversation in an emotionally charged situation. Compounding the discomfort was the fact that I usually had a working relationship with the individual in question, and may have even met their spouse and/or family at a Christmas party or other company event.

Common Mistakes

Not only have I had to initiate these tough conversations, but I have also had the opportunity to see how other managers, executives and board members approach them. Amazingly, there are still people out there who think it is preferable to a) deliver the message via cell phone, email or text or b) avoid the tough conversation all together and deal with the situation in covert ways.  Both of these alternatives create problems. While the use of phone, email or text typically gets the message delivered, it is a cowardly approach and can lead to a loss of respect. This can trigger more significant negative impacts down the road in terms of issues with retention, trust, teambuilding and integrity.  Even worse in my view is avoidance.  Those who are unwilling to confront a situation head-on tend to eventually resort to “weasel tactics” by trying to sabotage the individual within the organization. Examples of these tactics include holding shadow meetings and excluding the individual, talking negatively behind the individual’s back in hopes they leave, and sabotaging an individual’s progress in the hopes they quit. It’s an approach that carries only downside risk as it paints this so-called “leader” as weak and ethically challenged. This, in turn, jeopardizes their ability to build trust from the other team members they rely upon.

The right thing to do in these situations?

Summon up your courage and deal with those tough conversations head on.


It’s what good managers do and I have some tips that can help you:

1. Notify the individual that you want to meet in person to discuss an important item that has come up. Do not give in to any questions in regards to what the meeting is about. Nine times out of ten, the individual will either be aware or will subconsciously be aware of why the conversation is coming and will immediately begin trying to defend their position.

2. Prior to meeting with the individual, spend five-to-ten minutes sitting alone to relax. You might want to meditate or you might review your questions, but try not to think of how the individual may or may not react to the conversation. I can tell you that in all my years, I have never been able to predict exactly how an individual will react to this situation. Further, if possible, try not to bake into your mind the response or result you are wanting as you will not go in with an open mind. This will make it tougher to process the information provided.

3. Put together a list of five-to-ten open-ended questions (questions that cannot be answered with a simple “yes” or “no” answer) and be ready to lead with them. Remember, she or he who asks the questions holds the power in the conversation! Asking questions also enhances your ability to understand the issue at hand. And it’s a good way for you as a leader to calm yourself in a tough conversation as it takes the pressure and the spotlight off of you and puts it on the individual in question.

4. Note: If the meeting involves terminating an employee or dealing with an ethics or values breach, ensure you have a third party or your lawyer accompany you in the meeting to ensure all conversations are documented. This protects you and your company.

5. During the meeting you will be assessing the answers to the questions and you will come to one of three conclusions:

A) The individual has confirmed your initial findings;

B) The individual has given you additional new information which may or may not support your initial findings;

C) The individual has provided information which completely changes your perspective on the issue.

6. At this point, some leaders like to have time to assess what has been said and/or talk to others about what has been learned. Never be afraid to inject time into the process as a means for you to mull over the answers and assess how they relate to your impression of the situation.

7. Once you’ve reached your conclusions about the conversation, make a decision! Be direct and decisive and base the decision on the values you uphold for yourself and those around you.

There’s no question that tough conversations are one of the most difficult tasks for a business owner or manager, but remember that they also help to define you and your effectiveness.  Approach these conversations with courage, preparedness, open mindedness and a clear grasp of your values, and you won’t just deal with the situation at hand, you’ll grow as a leader.

Article by Chad Robinson.