Seven Great Questions to Ask a Woman You Are Investing In

Recently, a friend and I gifted ourselves with a face-to-face chunk of uninterrupted time. As soon as we sat down and I asked her how she was doing, she said, “Not good, friend.” Then the tears welled and spilled over. This girl needed to talk. So I listened, and out came all her profoundly honest, deeply vulnerable hurts. Essentially, she was saying: ‘This is me, with all my limitations and regrets.’ It was also my opportunity to say: ‘I am here. I hear you. Be how you need to be. Be who you are.’

I wonder which woman we are more like most of the time: the one who shares or the one who listens? I’ve found these equally valid questions: Are we able to share? and, Are we able to listen? Perhaps you’ve found yourself in both situations. More often than not I hear that most of the time, we pretend that all is well, and we maintain our I’ve-got-this demeanor. But for each of us, at some time, all will not be well. When that day comes, do have someone with whom you can be as honest as my friend? When that day comes, might you struggle with what to say? When is the last time you felt really heard, as in, you could talk and weren’t interrupted? Your friend maintained eye contact, nodded frequently and exuded compassion as you shared your heart. Time slowed and you could just dwell in a safe zone where all that mattered were your words and your heart. For many women today, that sounds like fantasy. Between the demands of home, work, and family, we rarely get the luxury of being the center of attention for a moment, much less a fat hour.

Whether or not you’re in an official mentor/mentee relationship, women are investing in each other all the time and investments mean thoughtful deposits. Most of the time, all you need is a few good questions, an available space and a generous heart. Not everyone is as immediately open as my friend. Sometimes we need to nudge a little. To that end, you may need a few  questions to kick off a conversation that will enable you to learn more about and thereby help your mentee.

women sitting on a pink couch

Here are seven that are proven to make space to be real and to be heard:

  1. How have you seen yourself changing over the last few years? Or, in what ways do you
    feel stuck?
  2. What do you like best about yourself?
  3. What’s a typical daily challenge?
  4. What could someone say to you that would encourage you the most right now?
  5. Where do you feel most needed?
  6. What could alleviate your stress right now?
  7. What does someone need to understand about you?

Sprinkle these questions throughout your time together. These kinds of queries take some ruminating. She may struggle with some, but eventually you will begin to discern the inner landscape of your mentee, enabling you to really ‘see’ her and love her even better. Remember, you don’t need to be perfect, just present.

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1 Comment

  • Michele says:

    Sometimes when I am sharing, #6 really makes sense. Sometimes I (or someone else) just wants to just share, but sometimes we’re looking for suggestions.

    I like the ask the question sometimes “how can I help you right now?” because sometimes the way that WE want to help doesn’t actually match the way that person needs help.

    When my husband left our marriage for another relationship, what I needed most was knowing that people cared about me (either by just words of affirmation, letting me know that they were praying for me/my marriage/my family) or sometimes, taking my son for a little while just to hang out with their family or to pick him up/drop him off.