“The smart ones ask when they don’t know. And, sometimes, when they do.”

Malcolm Forbes, Entrepreneur and publisher of Forbes Magazine

A client, coachee or prospect would like to learn more about our services and we have an hour scheduled with a ton of ground to cover. How can I ensure we touch on the most important topics? What can I do to make the most out of our time together? I’m discovering that the quality of my questions makes a big difference.

Questions are critical to becoming the advisor our clients are expecting and that the marketplace is calling for.

Being better at query applies across all jobs and responsibilities, and at every level. Improved questions support recruiting the right candidate, selling the needed work to my desired client, expanding important client relationships, strategically influencing colleagues, and coaching my people to get the very best out of them. Improving the quality of my questions even sharpens my parenting skills, strengthening my ability to relate to my teens, uncover their motivations and influence their decisions.

There is a methodology to asking better questions, a framework and set of rules that we employ to achieve results with others faster and more effectively too, which is the subject of this post.

Adopt the right mindset for query

Mindset is defined by Merriam-Webster Dictionary as “a mental attitude or inclination”. Before we learn new skills related to asking improved questions, we have to examine how we might need to shift our thinking. Here are four attributes that are the hallmark of a successful questioner – curiosity, caring, listening and collaboration.

Great advisors are curious. We must be interested and when we think “I wonder”, we should dive in and ask questions. As we build trust and relatedness with the other party, we earn the right to dig deeper and explore possibilities together.

Some questions are inherently difficult and more confronting to ask, but a good leader or advisor asks anyway. I believe it’s the care and concern we have for the people around us and their success that allows us to wade into those more challenging places. Great query is accomplished when I truly care for my client/coachee/prospect/colleague.

Being good at questioning is part of the equation, but true success in query is, in large part about listening. The most strategic questions are in vain if I don’t listen carefully to the responses. I must commit to listening fully and being present with myr client/prospect/coachee/colleague. This means stop multi-tasking, empty my mind of answers or the next thing to say, and be fully present with the speaker.

When we have a questioning mindset, we are also more effective when we collaborate with the answer provider. For instance, I know about recruiting best practices and methodologies, while my client knows the intricacies of their hiring plan and the skills that are essential in the candidate. Together we make a great team that uncovers the perfect candidate. To accomplish that, I must be willing to incorporate the client’s ideas into my plan.

Ask open-ended questions

This is one we all know; however, put us under pressure and we forget. Open-ended questions start with the five question words – who, what, when, where, and how – or might also be phrased as a directive statement like “tell me about…”. They cause the listener to naturally share more information and “work harder” in the conversation. Asking closed-ended questions (those that start with can, will, should, could, do and more) can, in contrast, make us feel like an interrogator pumping the listener for answers.

When I ask closed-ended questions, they are shaped and informed by my ideas, my experience, and instead of learning from the listener, I’m leading them. Open-ended questions will help me get to the collaboration I aspire to with my clients and colleagues.

Our query skills are habitual and closed-ended questions are a hard habit to break. At ConvergenceCoaching, we point it out to each other to help us practice. We play a game of “stump the questioner” where we turn especially tricky closed-endeds into open-ended questions. When we pay to the quality of our questions and weave more open-endeds into our conversation, we’re amazed at the new things we uncover.

Expand your question repertoire

In a February 2018 article called The 4C Questions All Leaders Must Ask, Bruce McCourt identified four strategic categories of questions. This was eye-opening for us! These four types broaden the quality of information we elicit from others. Each type of question has a purpose. When we use only one category of questions, which is typical, we leave information on the table and might also fail to progress the conversation. Using all four drives us toward new learning, new opportunities for collaboration, and an expanded level of rapport with those around us.  The four types are:

  • Context questions which focus on “the facts” and help us gather detailed information about a situation. They start with five of the six question words, including who, what, when, where and how. We need context, which is why we often start here to get oriented in a problem, issue or relationship. Sometimes we get stuck here too, spinning in data-gathering mode.

Which client was upset? When did they call? Who spoke to the client? What was their primary upset?

What was the result of your meeting with the partner?

Tell me your brief career story, including where you worked before and what areas of you specialize in.

  • Causal questions uncover the “why” and allow us to uncover and explore feelings, thinking and motivation. They focus on root cause, revealing the true drivers of behaviors and actions. For some, causal questions are uncomfortable and might evoke feelings of prying. As good advisors, we overcome those worries and wade in regardless to make a real difference for others.

Why are you seeking a new role?  What caused you to leave your prior employer?

What do you think is causing you to fall behind on your revenue target?

Why are you seeking to change your firm’s compensation formula?

Tell me more about that.

  • Challenge questions push the thinking of others and explore opportunities, impacts and difficulties. Challenge questions, tactfully managed, are the hallmark of an effective advisor/coach/client manager/leader.

This might be a long shot, but what plans do you have if the big project you’re forecasting for your Q4 revenue is cancelled?

How will you know that your investment in this marketing campaign is successful?

What are you afraid might happen if you don’t do this?

Challenge questions allow the other party to think differently, and even see things in a new light. They are a means to raise tricky and uncomfortable subjects without offending the other party. 

For both causal and challenge questions, we can seek permission before asking a question, which feels less intrusive. The opening could be sought simply by saying, “Can I ask you something?” or “I’m wondering why you…” or “I have a thought” or “this might not fit, but what if…” These are all lead-ins that bridge a curious leader into those trickier areas of uncertainty in the conversation.

  • Calibration questions prioritize opportunities and turn the discussion towards decision and actions. Calibration questions usually come toward the end of a topic or the end of a conversation. Calibration turns us toward next steps. Asking these questions too early makes the listeners feel rushed and can cause us to plan for next steps before we have the full picture, which could lead to a failure.  For example, if we only ask Context questions to a prospect, skip digging in with Causal or Challenge questions, and move right to Calibration, we risk proposing a solution that doesn’t really get at the heart of their issue or challenge and losing the work.

Calibration questions, asked at the right time, are critical to closing a deal or project and getting to action steps. Without them, we find ourselves in meeting redux, having the same unproductive meetings over and over.

Now that you have the proposal, what do you envision as next steps?

When do you expect to make an offer to a candidate, and what criteria will you use to decide?

We’ve identified the need to for you to connect more with your team – how will you get started on that?

When approaching an opportunity where more than one of you will participate from your firm, coordinate your questions ahead of time. Do as much upfront research as you can to minimize the Context questions and confirm the basic facts you’ve gathered.  Don’t skip over causal and challenge questions. Look for ways that asking better questions will help progress your relationships and knowledge.

Now that we’ve outlined this framework for asking better questions, I’ll calibrate and ask what’s next on our journey to get better in this area? For me, it’s to practice, practice and practice some more. To support my efforts, I created a “cheat sheet” next to my office phone that looks like this:

I am a committed listener who cares, collaborates and is curious.

I use open-ended questions (who, what, where, when, how, “tell me”)

Context (just the facts), Causal (why?),

Challenge (concerns, impacts), Calibration (next steps)

The phone conversations have already started…time put this into action!