Get That Job Or Raise By Role-Playing Important Conversations

“Why do you want to leave your current job?” my interviewer asked.

I froze. It wasn’t a strange question, but I was 22, at my first proper interview for a job in the marketing department of a weekly magazine, and I had not prepared adequately. I bumbled my way through a terrible answer about how my current boss was difficult to get along with. That was true, but it was the wrong reason to give. As soon as the words left my mouth, I realized my error. Needless to say, I didn’t get the job.

I always think of this incident when I’m anticipating an important work conversation. It reminds me why I practice for these conversations, whether it’s an interview, a review, or even just a tricky situation with a coworker. Now I like to role-play my main points and ideas out loud, with a friend or partner. This is the best way to prepare, both to hone your messages and to anticipate your boss or coworker’s response.

Here are some of my recommendations for how to role-play a job conversation:

Give your partner a meaningful role.
Print out the job description you are applying for and give it to them. Consider pointing out the areas where you think you are strongest or weakest. The person shouldn’t be an adversary, but they should challenge you the same way a true interviewer or colleague might. If there are any specific objections you anticipate—for example, if you are requesting a promotion or raise and think your boss will resist because business was down last quarter—share that, too, and practice fielding the tough questions.


Gather your thoughts.
Take time to deeply think through what you want to express. If you are going in for a job interview, jot down some of the most common questions—then make them specific to your field or industry. If you want, you can even practice your answers out loud to yourself. Try to remember themes and general ideas—not memorize answers or responses. The last thing you want is to sound scripted or like you’re not listening to what the other person is saying.


Set aside dedicated time.
Make sure you have enough time to practice—try 30 minutes. It’s easy to want to rush through the whole exercise, but slow down. I find that the first time I answer a question I often fumble my way through. If I have a chance to try answering it a few different times, I become more comfortable and practiced with what I’m expressing.


Solicit feedback.
Either during or after the role play, give your partner permission to help you improve by asking them for specific feedback. Did you use upspeak? What was your body language like? Which answers felt incomplete or thin? What were your biggest strengths? Do you need help with how to phrase a particular request or piece of feedback?


Expect the unexpected.
Conversations have a way of going in unexpected directions, so practice yours a few different ways. As an example, about a year ago I wanted to ask my boss for both a promotion and a raise. I role-played with my friend Steph and each time I practiced what I wanted to say, I brought up the promotion first and the raise second. On the day of the conversation, I felt nervous but prepared. I started by saying that I wanted to talk about a promotion and a raise, and he immediately responded, “OK, let’s talk about the raise first.” This simple change-up unsettled me; I was so stuck on the conversation going as I’d planned it in my head that I was unprepared to press him to begin with the promotion first instead.

It’s awkward to have a mock interview or conversation, which is probably the main reason so few of us do it. Try to make yourself overcome that feeling. Practicing how you present yourself and your ideas helps to refine what you really want to say and how you want to express it. Sure, it’s uncomfortable and can be stress-inducing—but so are interviews and important conversations with bosses and colleagues! You’ll be more prepared, and probably more successful, than 90 percent of people (note: unverified statistics) if you spend even a few minutes exploring how the interaction might play out.


The Grindstone” is a new series about how we work today by long-time Billfold writers Leda Marritz and Stephanie Stern. Looking for advice? Want to see a specific issue covered in the future? You can email them here.

Leda Marritz lives in San Francisco. You can read more of her writing at

Photo: Zoetnet



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