Are You Ready for the Hard Conversations?

A 2-minute quiz for tech managers

Are You Ready for the Hard Conversations?
Working Conversations 2-Minute Quiz

When someone on your team misses a deadline, your first instinct is to:

A Send a message asking what happened
B Wait to see if they bring it up
C Address it in your next 1:1
D Follow up with the whole team about expectations

There's someone on your team who is talented but hard to work with. You:

A Document the behavior before saying anything
B Hope the team dynamics work themselves out
C Schedule a direct conversation with them this week
D Address it in a team meeting so everyone's aligned

Your manager asks how things are going. You say:

A "Good overall, I'm keeping an eye on a few things."
B "Great." (You don't mention the problem.)
C "There's one situation I'm working through — here's my plan."
D "I've got an issue I need advice on."

When a difficult conversation doesn't go well, you tend to:

A Replay it and analyze what went wrong
B Move on and hope it doesn't come up again
C Follow up with the person the next day
D Wish you'd been more direct

How comfortable are you telling someone their work isn't meeting the bar?

A Very uncomfortable. I avoid it when I can
B Uncomfortable, but I do it when I have to
C Somewhat comfortable if I've thought it through
D Fairly comfortable. I'd rather address it than let it fester

Someone on your team pushes back on your decision in front of others. You:

A Explain your reasoning and hold the decision
B Get defensive and escalate
C Revisit the decision to keep the peace
D Table it and follow up privately

When you think about the hard conversations you need to have at work, which of these sounds most like you?

A I have good instincts but I'm not always sure how to execute
B I know these conversations need to happen; I just keep putting them off
C I tend to go hard when I'm frustrated and sometimes regret it
D I keep things calm, but problems tend to resurface later

If you could learn ONE thing right now, it would be:

A How to give feedback that actually changes behavior
B How to stay calm when conversations get tense
C How to have the hard conversation without damaging the relationship
D How to know when to speak up vs. when to let it go

Your Results Are In

You're one of four types. Which one are you?

Your answers point to a specific pattern. Here are the four types. Your full breakdown, including which one you are and what to do about it, is headed to your inbox right now.

The Improviser

Gets through hard conversations on instinct. Sometimes it works, sometimes it doesn't. The reason isn't always clear.

The Avoider

Knows the conversations need to happen. Keeps finding reasons to wait. The problem compounds while the clock runs.

The Escalator

Willing to address problems directly, but goes too hard under pressure. The aftermath costs more than the original issue.

The Deflector

Keeps the peace on the surface. But nothing fully resolves. Calm and closed are not the same thing.

Your result is on its way to

Check your inbox. If you don't see it in a few minutes, check your spam folder.