How To Ask Better Questions And Improve Workplace Culture

How Asking Better Questions Can Change Your Perspective and Shift Workplace Culture

Learning how to ask better questions is one of the best things we can do. It helps us to be more positive, aids in problem-solving and promotes constructive dialogue.

I’ve worked with many different organizations and see the same workplace culture challenges arise repeatedly. Almost every time, fundamental problems trace back to overwhelm and overload, accompanied by feelings of helplessness and a lack of control.

Perhaps you have been feeling this way too?

One Question to Shift Your Perspective

A simple question has the ability to start a conversation that can clarify, support, nurture, grow and heal.
Or, it can go the other way.

The catch? It needs to be the right kind of question at the right time.

While this feeling of overload is genuine (we see it in most places we work these days), you can quickly shift your perspective and workplace culture when you understand how to ask better questions.

A specific type of questioning will allow you and your team to:

  1. Identify the specific issues at hand;
  2. Shift your thinking;
  3. Take control;
  4. Change your situation.

One practice we discuss in the Conversations Bootcamp 1: Conversations Worth Having is generative questions – questions that generate ideas and information.

For example, let’s say I feel overloaded and overwhelmed at work and have convinced myself that I’m feeling helpless to do anything about it.

Here we have the choice to be mindful of where our thoughts are headed, and instead of assuming that we’re at a dead-end, we can ask ourselves: “Are you sure?”

Suppose I answer that question with, “Yes! I’m overloaded and overwhelmed, and there is nothing I can do about it!” I might go on to ask myself, “Are you absolutely sure?” and “What else might be true?”

How To Ask Better Questions And Improve Workplace Culture

Better Questions Lead to Better Answers

These questions and the subsequent internal dialogue that occurs lead me to ask myself if I am sure that I have no control over the mounting pile of work.

This might be true, or it might encourage me to ask myself additional questions and dig a little deeper.

Here are some examples:

How am I using my time?

Is everything that I perceive to be urgent actually urgent?

What if I sat down with my supervisor and went through my list of work? Could we reprioritize together?

What can I let go of?

Given the new ‘urgent’ tasks I’ve been given, are there some older ones that are less urgent now?

If my answer to this is “No,” then I might ask myself again, “Are you sure? Are you absolutely sure?”

If you’re looking to understand how to ask better questions about this topic, you might want to keep a list handy which looks something like this:

Is there something I’m doing that is enabling my workload to increase?

Am I volunteering for things I needn’t be?

Am I hanging on to old procedures that are outdated and unnecessary?

Am I working out of my inbox or just checking email periodically?

Am I scheduling chunks of time to get big projects done?

Am I scheduling in breaks so that I’m rested, most productive, and focused when I work? What else can I do to increase my focus?

Who can help me with this workload? Can others share the load?

As you intentionally learn how to ask better questions, the practice will come naturally, and you’ll likely see improvements in all areas of life.

Use Generative Questions to Build a Better Workplace Culture

The questions above are all just questions. They are questions I don’t know the answer to, which is what generative questions are.

Once you start asking them, one question leads to the next, and you may find that you arrive at some solutions where you initially thought there were none. They open up your mind to new possibilities!

You can apply the use of generative questions to many situations. In my book, A Better Place To Work: Daily Practices That Transform Culture (2018), I tell the story of Baptist Healthcare and their journey to create a culture that WOWs.

In doing so, they asked every employee these generative questions:

  • What do we want our culture to be?
  • Why do we exist?
  • What are we striving to become?
  • What guides our everyday behaviour?

Answering these questions generated their new mission, vision, and values, but more importantly, what their culture needed to be to achieve this new path.

Since workplace culture is made up of every person’s perspectives in the organization (it is the perceived ‘way things are done around here’), these questions shifted people’s mindset about the organization from what it was to what it could be.

Teach Yourself and Your Team how to Ask Better Questions

You can ask generative questions to yourself during almost any conversation to shift how you respond.

For example, suppose my colleague complains about a new system at work. Rather than commiserating and contributing to the sentiment, I can ask questions that shift toward a more positive, constructive conversation.

And that may lead me to ask my colleague what IS working about the new system or how they see the new system benefitting the team in the long run.

So, the next time you find yourself with a challenge and feeling that you don’t have a choice, remember that these simple inquiries can open up possibilities for yourself and others:

Are you sure?

Are you absolutely sure?

What else might be true?

Follow this blog for bi-weekly ideas to create a better workplace, sign up for my Conversations Worth Having Course HERE, or order my book, A Better Place To Work: Daily Practices That Transform Culture.

Enjoyed this article? Here are three more to help you:

Can You Get Good at Giving Constructive Feedback?
Improve Workplace Culture Through Better Conversations
Are Your Blinders On?

This article was originally published in 2019 but has been updated for 2021.

Deborah Connors

Deborah Connors teaches leaders to radically shift culture so that people can flourish. She is an engaging speaker, storyteller, author and coach.

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