Putting off difficult conversations is like ignoring a toothache - later is definitely not better.
But, with a little practice, you can master them!
I gave a talk about difficult conversations a few years ago at the SF Tech Leadership meetup. It seemed to resonate with a lot of folks. I can only attest that the more responsibility I’ve taken on, the more important this set of skills has become.
Let’s walk through some examples of difficult conversations (with increasing challenge) and how you might approach improving on them as a leader.
Level 1: Awkward
For example when someone’s personal grooming is an issue for the team (yes, indeed I’ve had this conversation several times in my career).
Pro tip: Your discomfort is less important than sparing them embarrassment.
How to get better at it: This one is easy to practice on friends and family. Tell people when their fly is open or when they have lettuce between their teeth. This will make awkward conversations at work easier.
Level 2: Alignment (or the lack of it)
For example, two teams working together pretend to agree on the surface and think they are making progress, but there is some fundamental mis-alignment hindering them from accomplishing something together.
Pro tip: You must make it clear you can walk in their shoes. Also, it’s not personal, it’s business.
How to get better at it: Practice noting out loud when you think there is mis-alignment between yourself and another person or between your team and another team. When you note it, make sure to state in a way that shows understanding their position.
Level 3: Apology
For example, you said you would do something and failed to follow through. Now, there are negative consequences for someone else. Or, maybe your team screwed up and you need to own it on their behalf.
Pro tip: Taking ownership will help diffuse negative emotions.
How to get better at it: Build a script. The first part is to own the mistake that was made. The second part is to demonstrate that you understand the impact the mistake has had. The last part is to own whatever the remediation will be.
Bonus: If your action or inaction hurt someone personally, ask for their forgiveness.
Level 4: Assessment
More specifically, there are times when you need to deliver difficult or negative feedback.
Pro tip: Avoid the “Sh*t Sandwich”, a uniquely American invention where you confuse someone about negative feedback by sandwiching it between two compliments.
How to get better at it: Build the script similar to the Apology: State the behavior that was observed. State the impact that it had. Invite the other party to reflect back the impact and suggest a remediation.
Level 5: Agonizing
For example a team member shares something truly difficult happening in their life. I’ve heard almost every imaginable personal tragedy as a leader - broken relationships, life-threatening health problems, deaths in the family. These all weigh heavily on the ability to perform well on the job, and it’s often helpful if a leader is in the know.
Pro tip: Listen first. Empathize if you can. If not, just listen.
How to get better at it: Again, this is something that is encountered in friend circles. Get good at listening and acknowledging. For people who are problem solvers, it can be tricky to avoid “fix-it” mode. Instead, offer to be of help if they want you to. Otherwise, your job is to listen and acknowledge the pain and difficulty they are going through.