Asking Deeper Questions

Go beyond the superficial to build better relationships

Vincent Vicari, MPA
2 min readSep 15, 2022


Photo by Christina @ on Unsplash

When you’re in a leadership role, getting to know your team as individuals is not always an easy task. You want to engage, but you don’t want to overstep any boundaries.

You should never be inappropriate or disrespectful. But, you want to treat your staff as humans.

So how do you go beyond the water-cooler talk? A simple strategy is to go beyond the superficial. Find out what they’re interested in that has nothing to do with work.

When you ask “how was your weekend?” See where they go with that. Did they go on a hike, to a museum, took the kids somewhere interesting, whatever it may be.

Then dive in a little deeper. Remember, we all like talking about ourselves. This is an opportunity for you to let your employee express themselves. But don’t dismiss what they say.

Remember what they talk about. Remember what interests them. Acknowledge them as a person, not simply as an employee.

Taking a deeper dive into interpersonal engagement will boost morale, develop better office relationships and build trust.

Allowing your staff to be human is a fundamental key to including them in your organization. It really is that simple.

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Vincent Vicari, MPA

Artist, illustrator, and writer on Personal Development, Leadership, and Creativity. See more at