Asking Great Questions; Art or Skill?

What do you think?

I think the answer is probably both, however I’d still like to hear from you on it.

I am confident that both art and skill are things we all can learn.

I know that we can get better at asking really great questions when we’re at work.

Today, my Thursday article for is called WorkHack: The Attitude of Q. & D. and I talk about a managing with aloha tool I coach managers in called Question & Dialogue.

Attitude is a tool. I’ve always thought of it that way, for tools perform and/or facilitate work, and the right tools make work easier. That’s certainly what a good attitude does.

Here’s a snippet of my article:

The best answers and the right answers can be elusive things in companies. One nagging reason for this is that best answers remain hidden behind the ones we’re too quick to settle for. They arrive in conversations with the culprits of “the way we’ve always done it,” “what the boss will probably want,” and “yeah, that’ll be good enough.” As managers, our job is to dig deeper, and to reveal all the options until we arrive at the best one.

Read the rest at Leon’s place:

At Hualalai I used to write a series of weekly emails called the ‘Ohana Mālama to help my managers create meaningful, work-productive dialogue with their staff every day at pre-shift. Much like our monthly Ho‘ohana here on Talking Story, there was a theme, but this one was weekly: they received it every Friday for the following week. Many of my managers would tell me these conversation starters ended up as the best help I gave them in both stimulating new thinking individually, and creating work initiative consistency with each department of the resort (we were a fairly large, departmentally diverse company).

Over time, we found that ‘soap-boxing’ in pre-shift meetings didn’t work: very easy for employees to tune you out and humor you. In fact, the underlying silent agreement between them would be ‘Don’t anyone ask a question or this will get dragged out even longer.’ Been there, have you?

On the other hand, having the manager ask great questions worked wonders; dialogue was lively and more interesting. Pre-shift was only 15 minutes long, and the conversations which started would flow into the rest of the workday: New ideas would be generated in real-time, immediate practice.

Here’s an example from a theme we called “No Room for Mediocrity.” Just for some context, Hualalai is a residential resort community with a Four Seasons Hotel. And on the wording, remember that this email went out to all managers to read, and then re-phrase in pre-shift using their own words framed in departmental context.

Daily ‘Ohana Mālama: Focus on the Customer

This week ”“ service questions to ask ourselves.  Seek honest answers from your staff, and get them to help you with solutions. They have the answers you want!

Monday/ Tuesday ”“ What do our guests ask of us?

“Be Flexible.”  They hate it when we say no, and are unwilling to bend the rules, or say “It’s our policy.” Can we be different and be more flexible? Do we need so many rules?
Question the rules you have in your operation ”“ Are they really necessary?  If so, how can service be provided to take the perceived bite away?

Wednesday/ Thursday ”“ What do our guests ask of us?

“Make it easy.”  To do business with us needs to be hassle-free. Can we build systems to eliminate the hassles?
Look closely: is it easy to call you? Is it easy to book a reservation, make an appointment? It is easy to “go shopping” ”“ no matter what the service that you provide in your department?

Friday/ Saturday ”“ What do our guests ask of us?

“Don’t nickel and dime us.” It already costs a pretty penny to stay here, whether a resident or a hotel guest, and they assume it’s a package deal ”“ they want a package deal. Are there inconsequential charges in our operations that bug our guests unnecessarily? Can we be more creative? Should we simply be more reasonable?

Sunday, or the last day of the cycle, after all employees had been engaged in the week’s project, was for wrap-up and capture of the best ideas that had been voiced and implemented effectively.

Todd Storch does a good variation of this with everyone in his Business Thoughts blog community, with his Monday Feature called “What If?” His question is a really terrific way to start a conversation asking for new, it’s okay to get crazy and dreamy kind of thinking.

Todd has asked questions such as:

#7  What if you spent an entire day away from your office, but you still worked?
#6  What if…you were a Super Bowl commercial armchair quarterback?
#5  What if you had to re-interview for your job?
#4  What if you were held accountable by 1-minute increments?
#3  What if you had 5 minutes to write out your best accomplishments?
#2  What if your best employee quit today?
#1  What if you still saw the world through children’s eyes?

What are some really great manager’s toolbox kind of questions you’ve used, or can suggest? What would you love to have your boss ask you? 

Let’s play Jeopardy here ” “please phrase your response in the form of a question.”

Related Post: Let’s play Synergy: Ask me a question


  1. says

    You have tapped into the core of what makes a good manager. Conversations, collaboration, providing direction, and getting the right information are all core to the manager’s job. Without the ability to ask good questions, you might miss important information needed to do your job as a manager. You could make the wrong decision, hire the wrong person, move in the wrong direction all because the question you asked wasn’t “good” enough.
    As most things with becoming a manager, asking great questions isn’t something that happens from day one on the job as a new manager (at least for most of us!). It takes great practice on an ongoing basis to hone in on the right questions to get the answers you need.
    You can’t give up and need to learn from your past conversations so that the next question can be more effective. With time, you will find the right questions to ask and become a great manager in the process!
    Glad you liked my post. My blog is an extension of my life as an executive manager. I hope to ask good questions to the blogosphere in order to start conversations and to learn what answers we can all learn from!
    Over these past few months, the skill of determining what to write in my blog and get the results I am hoping for have improved. Just to see that you referred to my site two posts in a row gives me the confidence that I must be doing something right.

  2. says

    Rosa, I agree that asking good questions is both an art and a skill. There is a dual level of skill involved actually. One on the purely technical level of whatever the subject is (the content). You don’t need to be a subject matter expert but you need to have more than a familiarity with the subject to ask good questions. And then you can deal in the context of asking the skillful question.
    That much said, I believe there is an art to the questioning. Reading all of the other environmental items, body language, posture, tone of voice, readiness to answer… all of these items can be perceived and used by the artful questioner in the right manner at the right time.
    The combination of skill and art can be devestatingly effective. The questionee would provide the answers (i.e information) without really understanding what “really” was happening. It was just a conversation to them. The artful manipulation never occurred.
    The questioner walks away having been successful again!

  3. says


    Just a quick link to a great post from Rosa Say called, Asking Great Questions; Art or Skill? I am a huge fan of GREAT questions. Provocative questions. Evocative questions. Tough Questions. Off the wall questions. Shocking questions. I like

  4. says

    Having trained in Appreciative Inquiry as a powerful method for facilitating change, I am always encouraged to hear stories of the power of questions in practical, everyday, embedded in the workplace situations.
    What I really like in Rosa’s story is how she and her managers really LISTENED to the answers. I learned from a friend who is an expert at marketing that one of the most damaging things you can do in the workplace, or in any relationship for that matter, is to ask questions without caring about the answers or to ignore the answers you receive. And, conversely, you know real dialogue has begun when asking questions becomes a habit throughout the organization, when every employee becomes curious, feels free to wonder “what if”.