Ask This Question Regularly for Connection

Since retirement, I’ve had more time to talk with friends and family. Small talk can get boring, so I have been looking for a way to easily connect more deeply with others (which requires knowing yourself). One way is to ask good questions (listen more, talk less ☺). The question I love is “how are you, really?”. Adding that one word makes it clear that I want to know more about you. But sometimes people don’t even notice the additional word; but mostly they do and there’s a pause. Why is that?


I think the truth is we’re often scared, or we haven’t taken the time to ponder our feelings. If I don’t face the fear or make the time to dig deep, I can forget about my wants or try to silence my emotions. Do you feel like that sometimes?


Over my 30+ year career, I’ve asked myself “how are you”, but not always consistently and with frequent reminders from journal prompts, coaching, friends, or therapists. At work, I didn’t always feel comfortable to ask the question, “How are you feeling?”, but I would ask my employees if they had made time to ask themselves questions like: “Why are you at this job? What is your larger purpose in this company and the world? Does this job and career lead to a life that feels satisfying and worthwhile? If we’ve answered these questions, then answering “how are you, really” will come more easily. And when you do this regularly you will put your career before your job, enhance your leadership presence and be happier.


Let’s ask ourselves and those we want to connect more deeply, “How are you, really?”.

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