The Art and Science of Having Difficult Conversations

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In business or in life, we often can’t avoid difficult conversations. Be it with our boss, our spouse, our kids, or a supplier or employee. Maybe you need to quit a job, get a divorce, tell your kids that their actions are not acceptable, or fire someone. Most people dread it and sometimes choose not to have the conversation at all. But that is not the right way to go. Not having the conversation leave the other person confused, unsure and having to fill in the blank with speculation and doubts. We must have those difficult conversations effectively and timely. Here are a few tips.

1. Set a time and ensure you are both free and in good spirit to have the conversation

Because it’s a difficult conversation, you want to have it when both parties are prepared, have ample time, at a quiet place and avoid interruptions. So you would want to plan for it ahead of time, set aside some time, let the other person know that it’s important for you to have the conversation, and let them know the topic ahead of time. This way you avoid the situation where the other person is caught by surprise, you don’t have time to finish the entire conversation, and other distractions.

More importantly, this gives you enough time to prepare and rehearse, and know what to expect. Because this will be a difficult conversation, you will need to be mentally prepared for good reactions and not so good reactions. Be at a place where you can stay calm and state your points comfortably without other stress factors (e.g. having the conversation at a public place with other people listening or watching). If the counterparty reacts badly, be mentally prepared to “take the hit” and stay calm. Suggest them to think over the topic discussed and offer another opportunity to pick the conversation back up, to avoid any regretted arguments and unnecessary tension. When they are stressed and emotional, it’s almost always better to let them cool off a bit and pick the conversation back up when they are in a better frame of mind.

2. Rehearse

This is like playing chess. You need to anticipate various versions of their actions and prepare a response to each of them. Sometimes it’s not enough to just think about your reactions. Rehearse with a trusted friend or family member. When we are stressed, we tend not to choose the best words or articulate our points. Preparation will help a great deal. Have your friend or family member play back what you think the other person might say and respond with your words. Do it a few times. Practice. This will hugely reduce the amount of stress when it’s time for you to do It for real.

3. Lay the foundation and clarify your intention

The first step is to set a foundation for your intention for the conversation. Sometimes the counter party may get caught up with what you will tell them and forget the big picture. Before you dive into the conversation, you need to remind them what matters more. With a boss or employee, maybe it’s your respect for them, the fact you enjoy working with them and your desire to work with them again in the future when the opportunity arises. With your spouse or children, maybe it’s the fact you love them and want the best for them, and you are having this conversation because of that. Be it what it is, don’t just dive into the conflicts and arguments. State the foundation and intention upfront, this will help them to listen to what you will tell them with the right frame of mind and don’t misunderstand or blow your words out of proportion.

4. Say it clearly without ambiguity and guess work

Once the foundation is laid firmly, dive into what you will say with clear, unambiguous words. Don’t beat around the bushes and let them guess what you will say. Say it out loud and clear, and follow up with explanations and justifications. Instead of telling them, things are difficult at the company, budget is tight, your performance is less than satisfactory, open with, “I am going to have to let you go”, and follow with the explanations. Sometimes, when you are dealing with a legally sensitive topic, don't just say anything. Make sure you consult a a lawyer if there are sensitive issues at play such as wrongful termination or discrimiation at the workplace.

5. Be prepared for an emotional response and know how you will handle it

This goes back to the rehearsal piece. Once you finish talking, be prepared for the person to be upset, emotional, and maybe even vindictive. Because this is a difficult conversation, know that humans don’t like to be fired, divorced, told that they are not doing well, etc. Expect them to react emotionally and irrationally. Keep your cool. They may say harmful or irresponsible things, but you must not respond accordingly and get into a downward spiral. Be prepared to say, “you sound upset, maybe you should take some time to think about this and we can pick this back up at a later time.”. If you are physically meeting the person, be prepared to walk away and ensure you have means to do so (in case of any kind of violent physical actions).

6. Leave the conversation with clear action items

If the conversation doesn't break down, conclude with clear action items. If you are firing an employee, tell them HR will follow up with a severance package, things to do before they depart, etc. Similarly, if you are terminating a contract, lay out things that need to happen before you both shut down.

7. Reiterate the good intentions and leave some hope for the future

Assuming you are able to conclude the conversation in an amicable and civilized manner, reinstate and reinforce the foundation and good intentions in part 3. The truth is this is a very small world and there is no need to create any kind of bitterness and hatred. Reinstate the reasons why you have to do this, be it business demands, love for the other person or whatever else, and leave some hope for the future. If you are letting go of an employee or supplier, tell them that when they do improve and grow in the future, you are happy to revisit their candidacy. If you are divorcing someone, tell them you still have things that you share in common (e.g. your children) and your friendship will continue. Even if this is a person you will never want to see in the future in your life, there is no point in calling it out. Save some face, leave graciously and amicably.