question-mark-285x300When coaching or training leaders to become more strategic influencers,  I focus early in the work on deepening one’s understanding of the other person. I often get two questions:

  1. Isn’t this line of questioning invasive on someone’s privacy?
  2. What are the questions that I can ask to get better understanding?

We often feel more comfortable asking about the work process than about the person. Asking questions about the person’s home-life, upbringing, etc. can be more awkward.  But, test what you do know and what would be useful to know. I often find that people haven’t even looked their influencing target up on LinkedIn or had a casual lunch to get to know the person better.

Of course, there are real boundaries about what you can or should ask people about their personal life situation. So, I’m not saying ask away about the person’s children, parenting mindset, hobbies, love-life, etc.

You have to be appropriate to the other person-ality, your current relationship, and your own style. Just don’t back down because you are uncomfortable or awkward–find a next step in the conversation of getting to know someone.

Here are some great questions for some people and some situations:

  1. (over lunch or coffee) Hey, I realize that I don’t know anything about where you went to school or grew up… tell me about your background. Even if you interviewed the person, you can always ask questions later.
  2. (when debriefing a project) Let’s put this situation aside, tell me about other similar projects you’ve handled here or at _____. What was the problem? How did you think about it? What did you do to resolve it?
  3. (in advance of an initiative) Before we launch into this initiative, I’d like to take the opportunity to understand much better your past experiences, ways of thinking and working, etc.)
  4. How are you? How are things going for you here? (you can ask this of anyone with any tenure)
  5. (if you are the boss) What am I doing that is working well for you? Not working well? Describe your best manager relationships in your past. You can listen for how the person thinks about hierarchy.

The most important caveat to all of this is that you have to be genuinely interested in the person. If you are interested, the person has a very high chance of listening to your question with that context.

You won’t be encroaching on the person’s privacy if you are earnest, link the question to the work or your relationship, and are clearly allowing the person to share or not.