5 Essential Questions Every Boss Should Ask Their Employees, According to a Veteran Manager with Over 100 Direct Reports

Christine Cruzvergara has overseen more than 100 individuals throughout her career in both academic institutions and corporate environments, yet transitioning into a leadership role was not without challenges.

Cruzvergara, who currently holds the position of Chief Education Strategy Officer at Handshake, started managing a team for the first time in 2011 when she was appointed as an assistant director at a university. She recounts to GudangMovies21Make It how her new role involved overseeing employees “who were over 25 years older than me and had much more experience.”

A significant lesson for Cruzvergara was realizing sooner the importance of establishing rapport and credibility with her new team members. This became clear to her after facing challenges during one of their initial interactions.

Initially, Cruzvergara started overseeing an individual she calls Hannah in a recent Forbes essay , who had missed out on the managerial position. In their initial encounter, Cruzvergara remembers providing some crucial criticism and observing that Hannah’s “exuberant and sociable demeanor” immediately disappeared.

The encounter made Cruzvergara realize that merely having casual conversations with Hannah prior to being her supervisor was insufficient for establishing trust and comprehension with her new team member.

5 inquiries every manager should pose

Ever since, Cruzvergara began initiating a practice where she asks every individual under her management these five crucial questions during their initial meeting:

1. What do you desire, require, and anticipate from your manager?
2. What irritates you the most?
3. What's your preferred way of getting positive reinforcement? How would you rather receive useful criticism? And when faced with negative feedback, what’s usually your response?
4. What kind of acknowledgment would you prefer when you perform well?
5. What project are you currently tackling professionally this year, and how might I assist you with it?

Cruzvergara informs Make It that she now presents each of her new reporters with a set of questions prior to their initial official one-on-one meeting. Throughout their discussion, she has the employee share their responses to these queries, while also offering her own answers.

Cruzvergara suggests that initiating this discussion early offers several advantages. Firstly, it establishes the right atmosphere and indicates to your staff members that you care about them, open to hearing their input, and dedicated to helping them achieve success.

As a manager, you’ll receive a concise guide on communicating with your team member, covering both commendations and critiques about their performance. This approach helps streamline the feedback delivery over time, making it quicker and more efficient depending on the individual, which paves the way for deeper discussions and early enhancements.

This approach can enhance employees' self-awareness by encouraging them to engage in deep reflection regarding their workflow, collaboration with colleagues, and management of feedback.

"I can’t recall a single instance where someone has been through this process with me without saying, ‘This was truly invigorating. No boss has ever asked me such questions before,’" explains Cruzvergara.

A single discussion can rapidly advance what would typically take months of collaboration.

Understanding employees' yearly objectives—whether they involve improving daily tasks such as managing emails more effectively or aiming for larger achievements like enhancing their public speaking abilities—informs Cruzvergara about everyone’s key focuses. This allows her to assist them throughout their journey. In return, staff members recognize her dedication to fostering their growth.

Lastly, Cruzvergara suggests that initiating this discussion allows your staff to start managing upwards more effectively. By disclosing your personal management styles, such as your irritations and preferred methods for receiving input, employees can better understand how to collaborate with you without uncertainty.

Following our initial encounter, both parties gained a slightly deeper understanding of each other," states Cruzvergara. "By openly discussing several aspects, we accelerated what would typically take months into a more efficient process, setting forth on a very positive trajectory.

Regarding Cruzvergara's initial managerial encounter with Hannah, they came together once more the next week.

As it turned out, her interpretation was entirely different," Cruzvergara noted in his writing. Forbes She mentioned that she enjoyed receiving feedback and felt she handled my criticism gracefully. After I shared with Hannah what I observed, she expressed gratitude for informing her and acknowledged that she hadn’t been aware of how she appeared. It’s true; this talk wasn’t easy. Nonetheless, it paved the way for smoother and more meaningful interactions moving forward.

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