Christine Cruzvergara has managed over 100 people in her career across universities and corporate spaces, but becoming a boss wasn't an easy transition.

Cruzvergara, now the chief education strategy officer at Handshake, became a first-time manager in 2011 after getting hired as an assistant director at a university and "inheriting a team where some of my staff members were more than 25 years older than me and were significantly more senior than I was," she tells CNBC Make It.

One of the biggest things Cruzvergara wishes she knew earlier was how to build rapport and credibility with her new reports. She learned this the hard way from an early interaction.

At the time, Cruzvergara began supervising someone, whom she refers to as Hannah in a recent Forbes essay, who had been passed up for the manager job. During their first meeting, Cruzvergara recalls delivering some critical feedback and noticing that Hannah's "effusive and outgoing personality" vanished right away.

The experience taught Cruzvergara that simply chatting informally with Hannah before becoming her boss wasn't enough to build trust and understanding with her new report.

5 questions every boss should ask

Since then, Cruzvergara started a habit of asking each person she manages five key questions in their first meeting:

1. What do you want, need, and expect from your supervisor?
2. What are your pet peeves?
3. How do you like to receive positive feedback? How do you prefer to get constructive feedback? And when you get critical feedback, how do you typically respond?
4. How do you like to be recognized when you do good work?
5. What is one thing you're working on as a professional this year, and how can I help you?

Cruzvergara tells Make It she now gives each of her new reports this list of questions before their first formal one-on-one meeting. During their chat, she'll have the employee give their answers to each question, and Cruzvergara provides her own responses, too.

Cruzvergara says having this conversation upfront has a few benefits. One, it sets the tone and signals to your employees that you're interested in them, receptive to their feedback and committed to their success. 

As a boss, you'll get a quick rundown of how to communicate with the employee, whether it's offering praise or adjustments to their work. This saves time in the long run when you can speed up the process of delivering feedback effectively, based on the employee, and opens the door to more substantial dialogue and improvements earlier on.

The practice can help improve employee self-awareness by making them think critically about how they do their work, how they work with others and how they handle and deliver feedback.

"I don't think there's a single time I've gone through this with a direct who hasn't said, 'Wow, this was really refreshing. I've never had a supervisor ask me these things,'" Cruzvergara says.

One conversation can fast-track months of working together

Getting to know employees' year-long goals — whether it's day-to-day routines like getting better at email management, or bigger-picture things like polishing their public speaking skills — helps Cruzvergara know what each person's priorities are so she can guide them through progress. They, in turn, understand that she's committed to their development.

And finally, Cruzvergara says having this conversation can enable your employees to begin managing up sooner. By sharing your own habits as a boss, like your pet peeves and how you prefer to receive feedback, employees can take the guesswork out of learning how to work with you.

"After our first meeting, they know me a little bit better, and I know them a little bit better," Cruzvergara says. "We just fast-tracked months of working together because we explicitly talked about some of these things and set off on such a good path."

As for Cruzvergara's first-time manager experience with Hannah, the two met again the following week.

"As it turns out, she had a completely different takeaway," Cruzvergara wrote on Forbes. "She told me she loved getting feedback and believed she had reacted well to my critique. When I told Hannah what I had witnessed, she thanked me for letting her know and admitted that she didn't realize how she had come across. Admittedly, it was a difficult conversation. But it cleared a path for us to have less awkward — and more substantive — exchanges later on."

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