How Do You Go Deeper in Conversations? Good Question.

Seems like everywhere I turn in my reading and conversations recently I stumble across someone who, essentially, says, “Here’s a question I ask others all the time that always gets a powerful response and always leaves me feeling I know that person on a deeper level.” While I don’t think it’s effective to incorporate planned or rehearsed statements in a conversation, I do think that it can be very effective to have a small number of meaty questions in your arsenal and to consciously slip those into conversations on a regular basis to take discussions beyond the surface level. Here are some of my favorites:

Question One: How did you do that? This from the book Change the Way You See Everything, where authors Kathryn Cramer and Hank Wasiak advise that the most important question you can ask anyone after they have accomplished a task is, “How did you do that?” The question affirms the importance of the accomplishment but more importantly, it allows a person to reflect on what personal assets were tapped in order to succeed. Whenever you recognize or praise someone in this way, it lasts. The more common question that people ask is "Why did you do that?" That question sets the stage for a defensive explanation.

Question Two: How did you acquire that skill (or characteristic)? This is similar to the previous question, but has a different objective. One of the fastest and most effective ways to develop a skill is to shamelessly imitate someone who has already embodied the kind of change you want to make. Think of a skill or characteristic that you most want to develop in yourself. Now think of somebody that you know who demonstrates mastery in that area and can serve as a role model for you. Ask them questions about how they acquired the skill you’re seeking. Tell them you admire them and intend to imitate them. They will feel highly complimented. You may even want to enlist their informal coaching and feedback support. Then practice what you observe and learn and continue to return to them for feedback and advice.

Question Three: What else? If you’ve ever watched a skilled facilitator work a flipchart in front of a group, you’ll notice a little trick of the trade…as they capture an idea on the flipchart on one line they immediately put a bullet point on the following line. This gives a visual indicator to the group that there’s always time and room for one more answer. This is essential when brainstorming because the best answers often come late in the game, long after the obvious solutions have surfaced. You can do this verbally by asking, "what else?" When a conversation seems to have lost steam or reached a natural conclusion, it forces everybody to go one step deeper. And it provides one more open invitation to air an idea that might be percolating.

Question Four: What gives you satisfaction? This is an interview question that Mark DiMassimo, CEO of DiMassimo Brand Advertising asks of every single job applicant he speaks with. He says it is the most effective question he’s found for understanding a potential team member. He hands them a piece of paper and a pencil and asks them to make a list of ten things they’ve done in their lives that they remember with satisfaction. Here are the rules of the game:

• The list shouldn’t include politically correct “interview answers.” He encourages them to be candid and authentic. “That ‘I broke up with my boyfriend’ could be an excellent answer,” he shares as an example.
  
• Five of the answers must come from before their 18th birthday, because those early successes reveal a lot.

He studies the lists, both with the prospective team member and after the interview, looking for themes, like courage, creativity, independence, adventure, rebellion, belonging and discovery. Once he has a sense of a candidate, he finds it much easier to match the satisfaction to the job and to anticipate from the beginning how things will go right and how things will go wrong with that person.

Question Five: What’s the most important thing we should be talking about today? In her book, Fierce Conversations, author Susan Scott offers advice about engaging others in meaningful conversations that move us closer to our stated business and life goals. One of her suggestions for initiating conversations that go deep and go there quickly is to set aside uninterrupted, one-one-one time and allow the other person to drive the agenda for the meeting. If you always drive the agenda, you may be missing something important. Here’s how she suggests you could set the stage:

"When we meet tomorrow, I want to explore with you whatever you feel most deserves our attention, so I will begin our conversation by asking, “What is the most important thing you and I should be talking about?” I will rely on you to tell me. If the thought of bringing up an issue makes you anxious, that’s a signal you need to bring it up. I am not going to preempt your agenda with my own."

No other style of communication is as effective in encouraging others to open up and engage with you as asking a question. A question is an invitation, by its nature, and requires a response. That's what makes asking a well-phrased, appropriately-timed question your most valuable tool for taking conversations and relationships below the surface.