Riddle me this

A few years ago, my brother Tom used the phrase “riddle me this” repeatedly. It was his form of asking me questions, and it was driving me nuts!  Because it often preceded what I felt was a meaningless (or sometimes annoying) question. What I appreciated about it was that after I told him how it was driving me bonkers, he made a joke about it in the form of my birthday card.

“Riddle me this is,” in fact, a valid form of asking a question.

In the past few months, I have been coaching a great many people on asking better questions. Questions that dig a little deeper, questions that, rather than solving the surface problem, reach further into the heart of the matter. Questions, like any other statement we make, are often habitual responses or a form of pleasantry. Think of how many times a day you ask someone how they are, which, if you truly consider the question, you are asking for a reply on their emotional state. (Most of us reply but not with sharing our emotional state, but with an adjective like fine, well, alright, great…or a response about our physical state, like tired.) So riddle me this, what’s a better question we could be asking people when passing in the hallway?

My initial thought on this might not be what you are expecting.

What if–you didn’t ask people how they were doing.What if instead of a rote, semi-empty question you said, “Good Morning” or if the person looks like something is going on, “Would you like to grab a coffee later?” (That question can be qualified with any form of meeting that suits your style and relationship best.) The point is, asking someone to spend time together is a radically different question. A question that forms a relationship. It’s a question that also inherently implies “I see you” “I am willing to connect with you” and “I care.”

Here is another scenario. If someone of senior authority asks you to take on a task (and implies the job is optional) instead of immediately saying “yes” out of habit, loyalty, or duty, what would it be like to take a pause, inhale and ask a question? A question such as, “If you were in my shoes, would you take the task on?” The idea, again, is to build a dialogue. To create a connection.

The last scenario I’d like to pose is, if you are in problem-solving mode with a client, teammate, or colleague, rather than asking questions like, “have you tried this?” Try asking a question that actually shifts the perspective altogether. For example, if the people you are working with are not the actual decision-makers in the process, try asking them the question: “If you were in charge, how would you tackle this?” Or, “What’s the worst-case scenario here?” or if you a glass half full type of person, “What’s the best possible outcome we can hope for here?” Another tactic is to ask a question from an emotional bent: “What’s the most frustrating (or perhaps exciting–feel free to fill in the appropriate emotion here) part of this process? ” Or, better yet, ask, “What matters to you most right now?”  Which may help uncover underlying values they have that are driving their decisions and actions.

As a communication coach, I see two things happening here. First, many of our conversations are driven by habit. “How are you?” is all too often just something we say, but don’t truly mean. So it begs the question, why ask it all? Second, the way to unlearn an old habit is to become aware of the pattern first. Then inhibit it the next time, by taking a breath–an actual moment of silence (which could potentially feel like a long time.) After that pause, exhale and consciously try something new like just smiling, or…asking a better, more potent question. Pose questions where you really want to know the answer. Inquire from a completely different angle. Ask about something that connects you, honestly, and more deeply to the person or people before you. 

In doing so, you may unlock the riddle of a few old habits, and unleash your potential for a new way of being present and connecting to others.