Dr. Andrea Hollingsworth
Hollingsworth Consulting

Last year, the research group QuestionPro surveyed 3,000 workers across various industries and companies, asking them how they respond when asked “how are you?” at work. Results showed that whopping 44% of people will always, or almost always, answer “I’m fine,” rather than giving a genuine response. Only 3% will tell the other person how they’re really feeling.

If you really want to connect with your colleague (or team) in a way that gets past the surface, look for better ways of checking in and initiating dialogues.

But how do you actually do it? How do you ask better questions?

Let me give you four guidelines that will make for more genuine and effective connections with those you lead.


#1: Make Your Questions Purposeful

The key to purposeful questions is specificity. You want your question to target something you know is pressing and relevant to the person or group. Say it was it was an individual employee on your sales team who dealt with some terribly rude customers last week. Instead of, “Hey! How’s it going?” ask, “Hey, I know you had some really difficult customer interactions last week. That can weigh on a person. Anything you want to process with me?” When you make your questions purposeful, you communicate that you noticed they went through something, you’re keeping them in mind, and you care enough to follow up on it in a pointed, solution-focused way.

#2: Make Your Questions Open-Ended

An open-ended question makes people feel respected and free. Let’s say you’re starting a one-on-one with a direct report. Instead of asking whether their projects are progressing on schedule (a yes/no query that forces them into a clipped and closed response), instead, try asking, “What’s something you’re feeling confident or energized about right now?” And/or, ask, “What’s something you’re feeling unsure of, concerned about, or unmotivated to do, right now?” These questions are likely to surface the status of the person’s work projects. But they’ll do it in a way that honors autonomy, communicates respect, invites resonant connection, and initiates free-flowing dialogue.

#3: Let Curiosity Guide You

Nine times out of ten, we don’t know what people are really going through, nor what’s actually on their mind. An attitude of curiosity says, “I don’t know what’s true of you, but I’m eager to find out! Help me understand you! I’m listening!” Does this require you to set your ego aside? Become teachable? Correctable? Yes to all that! But there are few better ways to make someone you lead feel esteemed and valued than to be truly curious about them. And don’t fret that curiosity will make you seem weak or cause people to lose respect for you. To the contrary: because your curiosity helped deepen their own self-understanding and self-esteem, they will walk away feeling like your presence called forth what was best and most insightful in them.

#4: Create Space for Vulnerability

Let’s say you’re leading your weekly team huddle, and want to start with an “ice-breaker” question or exercise. Instead of asking everyone, “What’s your favorite kind of doughnut?” try something like: “Is there something you’ve dreamed of doing for a long time? Why haven’t you done it?” Or, “You’re ninety, sitting on a park bench, reflecting back on your life. What advice does your elderly self want to give you today?” Such questions welcome people into more humanizing and emotionally attuned spaces. They fast-track connection, belonging, and team synergy. Are they riskier? Do they get folks’ heart rate up? Of course. But when you invite (and model) vulnerability with those you lead, everyone feels that who they are, in all dimensions of their human being, matters.


Asking better questions of those you lead benefits everyone, including you. You’ll feel more genuinely connected to people, and we all know that real connections make the good days better and the bad days tolerable.

You’ll also feel clearer on the viewpoints, needs, and challenges of others, which will empower you to better predict and solve problems.

Most of all, you’ll experience yourself as a leader who’s actively building a more humanizing work environment. In a world where collegial bonds are often surfacy at best, and toxic or dehumanizing at worst, there’s no greater gift.

About Andrea

Dr. Andrea Hollingsworth is Founder and CEO of Hollingsworth Consulting, author of the bestselling book The Compassion Advantage (2024), and one of today’s leading global experts on compassionate leadership. Since 2008, she has been studying, speaking, and writing about the science and spirituality of human emotions and relationships. Her articles have been published more than a dozen times in peer-reviewed journals, and she has taught at prestigious institutions like Princeton, Boston University, and Loyola University Chicago. In addition, Dr. Andrea has delivered talks to audiences at some of the top-ranked universities in the world—including Cambridge University in England and Heidelberg University in Germany.

Dr. Andrea spends most of her time inspiring leaders and teams to use The Compassion Advantage to build supercharged organizations through cultures of care— especially in times of challenge and change. Andrea lives with her family in Minnesota where she cheers hard at her son’s soccer games and relishes every opportunity to visit the north shore of Lake Superior.