How to Have a Hard Conversation

You know the feeling. Your heart is pounding. You feel sick to your stomach. Your eyes are heavy from lost sleep and your drive to work seemed to take twice as long. Today is the day you have to have that hard conversation.

Difficult conversations are part of any manager’s responsibilities and the ability to successfully execute them can either make or break your effectiveness as a leader. You need to have confidence in knowing that you are actually doing your team a great service by having tough conversations with them. Yes, it can be awkward and uncomfortable, but in a roundabout way, you are showing them that you care enough to take the time to help them grow. A wise man once said, “accountability is a gift” and it is so true. We as humans are often blind to our own shortcomings but most of us have the desire to grow. When improvement opportunities are tactfully and thoughtfully communicated by those closest to us, the results can be life changing.

A major risk, however, of giving constructive criticism is that it could fall on deaf ears. You must know that your team will never truly be able to receive and grow from criticism if they can’t trust you. Employees need to know that you are for them, you fight for them and you genuinely believe the best in them. I sit down every one of my employees on day one and tell them that I am on their team and that I will be fiercely loyal to them. Words are cheap, but over time I do my best to PROVE it to them. When the time comes to have a hard conversation, it’s always received much better because they know that I have their best interest at heart.

Knowing the importance of having difficult conversations and keeping the challenges in mind, here are a few tangible steps that should be considered every time you must have a hard conversation.

Step 1 -- Prepare:

Before you initiate a hard conversation with someone, you should write down exactly what you want to communicate. Opener, meat and conclusion. Write it all down. In the heat of an awkward or difficult situation, our mental capacity is often monopolized by our emotions instead of the substance of the issue. When you have notes, you won’t forget anything or regret something you communicated poorly.

Additionally, it’s therapeutic to write down how you feel about a certain topic. You may even omit or add something after seeing it on paper that you would have otherwise forgotten. Besides the benefit of not forgetting anything, the practice of writing things down will force you to give meaningful thought to an issue instead of just saying what comes to mind in the moment.

Of course, conversation will evolve outside of your planned words but plan for that as well. Anticipate three different reactions from the person you are having the conversation with. Put yourself in their shoes and begin to imagine how they might react. It will allow you to prepare for any rebuttal and it will also give you a perspective outside of your own. 

Step 2 -- Execute:

Before you begin a tough conversation, ask the other person for permission to speak to an issue. Then, if given the green light, ask for permission to be direct. Although you may not “need” permission to speak to a subordinate, it is a strategy that makes them feel involved in the process and can help bring their walls down. Also, if you receive their blessing to be direct, it allows you to not have to dance around the issue and get right to the point.

Stephen Covey famously says: “seek fist to understand then to be understood.” I’m convinced that the most successful and effective leaders in this world are the best questions askers. That theory carries over into having hard conversations. Don’t assume anything, especially the worst in a person. At all costs, try to avoid speaking to character deficiencies as that will initiate the fiercest of defense mechanisms. It’s amazing what you can learn and how much better you are received when you approach a hard conversation by asking questions first.   

Step 3 – Follow up:

There is a good chance that at the end of a hard conversation, one or both parties will feel frustrated or hurt. That is okay. If the relationship is meaningful, whether professional or personal, it was worth it. End the conversation with a pleasantry like “I really respect you and I appreciate the opportunity to work this out,” then schedule a time to follow up.

A follow up conversation will allow the two parties to take some time to gather their thoughts and bring back anything that they forgot to say or wish they would have said differently. This ultimate step may seem like overkill but it is the final healing agent to prevent a feeling from festering into a grudge. The healthiest business relationships keep “short accounts” and move forward whole after successfully executing a hard conversation.