What we consider a difficult conversation depends greatly on the person. To some, talking about money is difficult; to some, it’s easy. To some, strong emotions are scary; to some, they’re okay. To some, it’s natural to disagree and bring up differing opinions; to some, it feels uncomfortable. When some upcoming conversation feels difficult to you, think about the aspects that make it so. For example:
The topic is difficult, and it makes you uncomfortable.
The topic might be difficult for others, and they probably don’t want to hear it.
The personality of the other is somehow difficult.
The situation is difficult for some or all of the participants.
The relationship doesn’t feel strong and safe enough to bring up the topic.
The relationship is strong, and it feels scary to strain it with the discussion.
The outcome is potentially scary, and you have something to lose.
This is not the first time, and you’re back having the same conversation again.
The emotions have risen, and you’re anxious, upset, frustrated, or sad.
Depending on the aspect of difficulty, it affects how we prepare ourselves for the conversation.
If it’s the topic or the situation, we pay a lot of attention to the opening and wording of the conversation.
If it is the personality, the relationship, or the emotions, or we’re back having the conversation again, we need to make sure we don’t have prejudices and that we’re striving for objectivity.
We should also assess if we should handle the situation on our own or maybe ask for help.
If we have something to lose, we can prepare by going through different scenarios.
We’ll dive into all of these in the upcoming chapters. But before that, let’s take a look at the three most typical types of difficult conversations and how to approach them.
We need to disappoint or deny
We like to say yes and make people happy. Yet, we can’t always do that. We can’t give everybody everything they want simply because of crossing interests. We will disappoint somebody because saying yes to something often means saying no to something else.
Sometimes we need to disappoint people beforehand by not promising things and by lowering expectations. Sometimes we need to disappoint people afterward when we realize we can’t keep all our promises. It’s way better to learn to disappoint people by not promising things than to disappoint them by overpromising things.
Knowing we need to disappoint or deny, we can prepare ourselves. When approaching a conversation where you need to disappoint somebody:
Consider whether it’s a no or
not yet
not all of it
no to X, but how about Y
yes, if X.
Avoid using a but; use and instead:
“I know you wanted this, but this time I cannot give it to you.”
“I know you wanted this, and this time I cannot give it to you.”
When we use a “but,” it tends to diminish what has been said before it. Therefore the opening of the sentence loses its value. Using “and” instead of “but” makes both parts of the sentence to be true at the same time. It helps create a more collaborative tone in communication and avoid the perception of opposition or contradiction.
We need to change or course-correct somebody
Probably the hardest and most uncomfortable conversation is to face a person who is somehow not behaving or performing the way they should, and we have the task of trying to change them. We might be frustrated by the situation, or the person who has put us up to the task is frustrated. We feel pressure to fix things, and at the same time, we’re reluctant to bring this topic up with the person. It’s very tough to tell a person something in their behavior needs correcting, yet we often face these situations.
These can be, for example:
A team member isn’t reaching the goals you’ve set together.
A team member smells bad at work.
A subcontractor has gone missing and hasn’t been available for weeks.
A client calls team members directly asking for things even if you’ve agreed they should only contact you.
A colleague is using inappropriate language on Slack or Teams.
Somebody is stealing office supplies.
We have to acknowledge that we can’t really change anybody. We can only try to invite them to participate in the change. We can do that by:
First, bringing up the problematic behavior by being as objective as possible and avoiding giving interpretations.
Then, listening to them intently, letting them tell their side of the story, and making sure they feel heard.
Finally, removing obstacles, giving incentives and motives to change, letting them know what happens if they don’t change, or coming up with the next steps and agreements together.
We need to bring bad news
The last type of difficult conversations revolves around bringing bad news. These could be:
A project is going to be late due to an unexpected problem.
Somebody is being fired or a contract is terminated.
We have found out someone from our team has been stealing office supplies.
We suspect somebody has a substance abuse problem and must inform them we need to take action.
The service our team has worked hard for is closed down, and the team members will be relocated to new projects inside the organization.
The team size needs to be cut back due to staff reductions.
In these situations, there might be very little room for negotiation, and it’s our task to be the bearer of the bad news. As leads, we should take responsibility for what we need to deliver. If the project is late, it’s not helpful to put the blame on the team. If we need to terminate the contract, it’s not helpful to put the blame on the upper management. If we need to talk about substance abuse, it’s not helpful to put the blame for the uncomfortable conversation on the HR department.
There are three steps in the process:
Step one is to bring the bad news as clearly and kindly as possible, but at the same time very firmly too.
Step two is to let them react and just listen to them. We can listen empathetically even if we disagree with what they’re saying or even if we can’t budge an inch.
Step three is to gently direct the conversation toward how we’re getting forward from here.