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

The amazing thing about a simple question is that it has the ability to start a dialogue, and bring people together to have a conversation that can clarify, support, nurture, grow and heal. The catch? It needs to be the right question!

I’ve been working with a few different organizations over the past couple of weeks, and the same workplace challenges keep arising in our discussions. These issues are voiced in different words, different situations and different workplaces, but in every case, trace back to overwhelm and overload, accompanied by the unfortunate feelings of helplessness and a lack of control.

Perhaps you have been feeling this way too?

While this feeling of overload is very real (in fact, we see it in most places we work these days), there are ways to shift your perspective and the workplace dynamic by asking yourself some questions. This form of questioning can allow you to not only identify the specific issues you are dealing with, but also help you to shift your perspective about it, and perhaps enable you to increase control over the situation and take steps to actually change it.

Are You Sure? Are You Absolutely Sure?

One practice we discuss in the Conversations Bootcamp 1: Conversations Worth Having is the use of generative questions – questions that generate ideas and information. For example, let’s say I’m in the situation above where I am feeling overloaded and overwhelmed at work. I’m feeling helpless to do anything about it. A generative question I might ask myself is “Are you sure?”

If 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?”

These questions and the subsequent internal dialogue that occurs leads me to ask myself if I am certain that I have no control over the mounting pile of work that I have. This might be true, or it might encourage me to ask myself additional questions, and dig a little deeper, such as, “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?”

I might ask myself if there is 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? More importantly, am I scheduling in breaks so that when I work, I’m rested, most productive and focused? What else can I do to increase my focus? Who can help me with this workload? Can others share the load?

You see how this goes. These 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!

Maybe the workload is completely too much and unsustainable and if so, what are my choices now? Do I need to be looking for a new job? Am I able to work flex-time to have more days off? Or, how might I educate my boss about work sustainability? Or, how might I set more boundaries? Or, have more balance?

When to use Generative Questions

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 in order to achieve this new path. Since culture is made up of the perspectives of every person 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.

You can ask generative questions to yourself in the midst of almost any conversation to shift how you respond. For example, if my colleague is complaining about a new system at work that they don’t like, rather than commiserating and contributing to the complaining-fest, I might ask myself “What question can I ask right now to shift to 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, ask yourself, “Are you sure?”

“Are you absolutely sure?”

“What else might be true?”

Deborah Connors is changing the workplace conversation by teaching leaders to radically shift culture so that people can flourish. Follow this blog for frequent ideas on creating your “better place to work.”

The practice of ‘Generative Questions’ comes from the course “Conversations Worth Having at Work” that Deborah will be teaching again online starting November 21/19. To delve deeper into these practices, join us for this course by registering here . Team pricing is available.


Book Deborah to speak at your event or in your workplace here .

Her book: “A Better Place To Work: Daily Practices That Transform Culture” makes a great Christmas present for the book-lovers on your list.

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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