Powerful questions can help you punch through to the guts of your workplace culture. (Photo by Lopez Robin on Unsplash)

Quick links: What are “powerful questions”? | Who should I ask? | The five powerful questions

It always seems to start with coffee…

I had coffee several months ago with the former founder and CEO of a local technology company that had been acquired by a larger organization from overseas. He had recently stepped back from his role as CEO but was still helping the parent company with a few things. It was a great conversation that naturally led to us talking about workplace culture.

We both had perspectives on how crazy and complex cultural issues could be in a large organization that had mostly been built from buying many smaller ones. I was happy to hear that in his case there seemed to be a genuine curiosity and desire on the part of the parent company to learn from their newest acquisition.

One area where he saw opportunity for the company was in building a more cohesive, healthy culture across the many divisions. However, he was struggling to figure out the right way to approach the organization’s executive leadership. He didn’t want to go in guns blazing and tell them what he thought they should do.

After some discussion, I suggested to him that maybe he start by asking some simple questions and see where the discussion led from there. I’ve often found that the right question can help illuminate things not just for the person asking them, but also for the person being asked. He asked me what questions I thought he should ask – I said I’d get back to him once I figured out what they actually were!

What are “powerful questions”?

After giving it some serious thought (assisted by a dram or two of scotch) I came up with this list of five powerful questions. What are “powerful questions”? Powerful questions are often used in executive and leadership coaching (check these examples out from the Co-Active Training Institute) and are typically:

  • Open-ended: the answer to a powerful question will rarely be a simple “yes” or “no”.
  • Rooted in curiosity: powerful questions are asked without judgement or anticipation of what the answer could or should be.
  • Thought-provoking: the answer to a powerful question usually requires some deeper thought and introspection.

For each of the five questions below, make sure to ask for examples. For instance, it’s easy for a leader to say, “We believe in openness and transparency.” Cool. Now tell me a time when you actually practiced that openness or witnessed that transparency.

These questions are meant to be hard.

They’re not meant to be answered in ten minutes or less. You could probably talk with seven people all in one day, or one person a day for a week over lunch. You could also start with just one of these questions and end up having a really great discussion. Regardless, if you spend the time to ask these questions I guarantee you’ll have some interesting and illuminating conversations.

These are not questions designed to tell you whether your culture is healthy or not.

Rather, they are intended to trigger a deeper discussion around your organization’s purpose, values, and behaviours. (If you don’t know already, purpose, values, and behaviours are important things that make up a workplace culture.)

Who should I ask?

Ask as many people as you can, whether it’s over coffee or lunch, or in a more formal meeting.

These questions can be asked of anyone, by anyone. 

If you’re the CEO, ask your front desk receptionist so that you can get a sense of how aligned you each are in your perception of the company’s culture. If you’re in HR, ask your VP or Chief Human Resource Officer. If you’re interviewing for a job, ask your future manager.

If you get the same or even similar answers from everyone, the odds are you’ve probably got a pretty cohesive culture. Everyone’s rowing the boat in roughly the same direction. Again, whether it’s healthy and high-performing or not is a different matter. Maybe you’re all rowing upstream toward a mob of hungry cannibals, but at least you’re all rowing together!

Whoever you are, the goal of asking these questions is to get a feel for how aligned people are on culture.

So, the first person you should ask these questions of is yourself.

With all that said, let’s get right into the first of the five questions.

Q1: What is the purpose, or “why”, of this company?

(And tell me about a time when that purpose guided an actual decision you made or action you took.)

What is this company’s role in the universe? The idea of a company having a purpose – a vision of why it exists – is nicely illustrated by author Simon Sinek in his book “Start with Why” (and in the TED Talk video below).

If the person you ask says, “our purpose is to make money”, that’s probably not what you’re looking for. Every for-profit organization wants to make money, and there’s no uniqueness or differentiation in that. Your organization’s “why” should go deeper than that.

For example, the folks at PlayCity App have (in my opinion) a great purpose: “to connect people through play”. Everything they do as a business is geared toward achieving that vision of getting human beings to interact more through sports and other physical activities. And having talked a number of times with their founder, Hafiz Mitha, I know that they often make business decisions guided by that vision.

Q2: What was the last big decision you made that was guided by the company’s values?

(And what was the last one that was not?)

I love this question because it tests a few things about the person’s understanding of:

  • The general concept of values, which are core beliefs that guide behaviours and actions;
  • The person’s understanding of their organization’s values (if they’ve been defined); and
  • How the values are being deployed in practice, in actions and decision-making.

Having a list of core values hung on the wall is completely useless if nobody knows what a value is, what they are, or how they’re supposed to use them.

Q3: How would you describe the relationship between employees, customers, and shareholders?

The relationships and interactions between the shareholders / owners, employees, and customers of an organization can be very complex. This question helps you understand that relationship a bit better. For example, if you have a culture of servant leadership, you would expect the answer to be, “if employees are cared for and put first, those same employees will be highly motivated to create loyal and satisfied customers.”

Does your organization treat employees like they’re disposable? (Photo by Ross Varrette on Unsplash)

I’ve worked for many companies that see their employees as human beings, people who have emotions and feelings and families and lives outside of work. I’ve also worked for, and know of, companies that don’t see their people this way. Or if they do, they don’t show it. These companies view their employees as commodities, resources, or assets that can be treated in the same way you’d treat a computer or desk. Oh, that fax machine isn’t performing well anymore? Just get rid of it. (Although, it is 2020, so maybe it actually is time to get rid of the fax machine.)

Q4: What does a healthy, high-performing culture look like?

(And where is the current culture in relation to that?)

This is actually the first and only question with the word “culture” in it. This question achieves several things at once, including:

  • Sparking a discussion about what culture means to someone else, and how they define it.
  • Assessing opinions and perspectives on the qualities of their ideal culture, and what “healthy” and “high-performing” mean to them.
  • Opening a great discussion around how to measure health and performance i.e. how do you KNOW that you have a healthy, high-performing culture?

As I wrote in another post, assessing workplace culture health is often a combination of emotional feelings, and quantitative measurements such as metrics or key performance indicators (KPIs). This question is a great gateway into a conversation about someone’s attitudes toward culture, and how they define it.

Q5: Tell me about the last crisis the organization encountered, and how did it go?

I’ve written previously that, in my opinion, the single most important way to assess the health of your workplace culture, is the organization’s ability to adapt to change. I also wrote in an article for People Managing People that crisis management and change management share many similar practices, and a crisis is often the catalyst for broader organizational change.

I’m not talking here about adapting to a new travel policy or benefits package. I’m talking about a major crisis or a really big change. Maybe it’s the firing of a beloved CEO or a company-crushing lawsuit filed by a larger competitor. Maybe it’s a disruptive new technology or a global pandemic (COVID-19 anyone?).

Whatever the crisis is, how your company adapts and manages it is the real key to understanding what your culture really looks like and how healthy it is.

There are no right or wrong answers…

It’s important to realize that there are no black-and-white, right or wrong answers to these questions. And often, we don’t know the answers ourselves. (Like I said at the start, the first person you should pose these questions to is yourself.)

These questions are intended to give you an idea of whether everyone in the company know where it is going, why it is going there, and how their contribution is helping.  a deeper discussion around your organization’s purpose, values, and behaviours. The answers will give you a sense of how aligned you are with those things. However, the questions are also meant to help you get a better read on the person you’re talking to when it comes to matters of workplace culture.

HOW the person answers them is almost as important, if not equally important, as WHAT their answers are.

For example, it’s a red flag if the person dismisses the question as unimportant or irrelevant. Similarly, warning bells should sound if they obviously don’t have or know the answer, but choose to just make something up. It’s always better when someone is honest and says, “I don’t know, and it’s a good question that I’ll look into”.

The reality is that these are tough questions, and the answers themselves are just one piece of the puzzle.

What do you think?

What questions have you asked that have given you good insight into your workplace culture? What questions has someone else asked you? Does your organization have a published vision and defined core values, and do you seem them integrated into your culture?

Weigh in on these questions in the comments below and subscribe to the Culture Assassins newsletter to stay up to date with all of my deep thoughts and amazing insights into workplace culture. 😉