The art of asking questions

Being a leader can be challenging. The skills required can range from technical knowledge to emotional intelligence.

When we have a high level of trust, we give each other the benefit of the doubt. This is true even when we say the wrong thing or come across as blunt or critical. When others trust that our intentions are always good, the words matter less. Building trust for leaders can help you explore the ways that trust can be eroded, and ways you can build it back up.

The role of manager or supervisor also requires the ability to encourage and support the success of a diverse group of employees. Employees may come from different generations, cultures, ethnicities, privileges, and levels of confidence.

The expectation is to be able to lead and respond in ways that are effective with a diverse population. We want leaders to be inclusive, psychologically safe and effective at getting the job done. It’s a lot to ask.  

What follows are techniques that can help.

Why a question?

When we make statements, especially about other people, we risk getting it wrong. We might use a term or phrase that someone misunderstands or finds offensive. Statements may sound like they’re not up for discussion, even when that’s not your intention. We might think there is a shared understanding, but later find out that we were wrong. 

A misunderstood statement or directive could cause a lack of trust, a waste of time, frustration or even humiliation for either party. When we ask “good” questions we are inviting discussion and collaboration. This helps to reduce misunderstanding and increase engagement.

Asking good questions has the potential to create a psychologically safer environment where people feel comfortable to speak up. It helps build trust and relationships. It allows employees to feel that what they contribute matters, and encourages innovation and problem solving. 

Guidelines for a “good” question

A good question is one that:

• Does not trigger resistance or defensiveness. It should imply curiosity rather than judgment. 
  • Rather than “Why would you do it this way?”, a better question might be “Could you please walk me through the steps you took to do this?”
  • Use appreciative inquiry as a strength-based approach that can help you avoid the impression that you’re assigning blame or attacking.
• Has a tone that is open and inviting. While you may feel your own pressure at work, it’s important to resist sounding impatient when speaking to others.
  • One approach is to take a brief moment to breathe and calm yourself before beginning a discussion with others. Four-stage breathing is an exercise that can help you do this without drawing attention to yourself.
  • Consider the intensity with which you’re speaking and how that might be interpreted. Communicating with clarity is an exercise that can help you with this.
• Isn’t leading or loaded. If you already know the answer or have an expectation of the answer, the question could be loaded. 
  • Rather than, “Don’t you want that promotion?” you might ask, “What strategies are you taking to set yourself up for the promotion?”.
  • Consider how your intentions and assumptions might impact your approach. Preparing for a difficult conversation provides a series of questions to ask before engaging that can help you reflect and prepare.

Choosing your own good questions

The Workplace Strategies for Mental Health site contains examples throughout, especially in the Approaches for people leaders section, of questions to deal with many situations including:

• Conflict response
• Violence response
• Performance management
• Accommodation (especially around mental health)
• Supportive task improvement
• Debrief questions
• Conversation starters for psychological health and safety
• Identifying employee issues
• Developing an employee plan for performance or accommodation
• Team agreement process
• Inclusion
• Employee workload stress

But these examples only become “good” questions when put into your context. The way you begin to develop your skills in asking good questions can include the following:

• Look up content on this website and elsewhere that are relevant to your situation. Choose those that meet the Guidelines for a “good” question above. Consider how this approach may work with your own current emotional state and communication style. Identifying employee issues can help with this.
• Build trust so that even if you do misspeak, those around you are aware of your good intentions and are willing to give you the benefit of the doubt. Building trust for leaders can help you with this.
• Thinking about the potential reaction of the person you will be talking to. If you are concerned about an emotional reaction, Communicating with an emotional employee can provide tips and strategies. 

But what if the answer is…

Even employees who are generally not reactive may occasionally surprise you when you ask them a “good” question. Their answer or reaction may be not what you expect because they’re:

• Dealing with life or health stressors you know nothing about.
• Fearful of losing their job, making them feel any communication with you is a potential threat.
• Relating the interaction to a past interaction with you, or another leader, that was not positive.
• Dealing with conflict or harassment at work and feeling vulnerable.

The first rule of responding to any answer is to listen to understand. This means allowing for pauses as they consider your question, and not interrupting until their entire thought is finished. It also means seeking clarity about their perspective, which can include: 

• Digging deeper
  • If the response is confusing but not emotionally charged, you can always prompt for more information by saying in an inviting tone, “Tell me more”.
• Taking responsibility for the reaction
  • When someone seems flustered or emotional about the question, you could say: “I’m so sorry, I’ve obviously asked that incorrectly.”
• Pivoting or restating
  • Taking another approach. “May I take another stab at that question?” or “Can I try that again?  I really just wanted to ask about…”
• Responding to a disclosure
  • You might ask what you think is an unrelated question, and the response is the disclosure of a mental or physical health concern, a family or relationship issue or a challenge at work. It may be that you made it safe for that person to speak up, or it may be a tipping point that if they felt they didn’t disclose, they would be disciplined or fired. 
  • To respond, acknowledge that the individual has just shared something with you and ask how you can help them with that situation. This doesn’t mean you’re agreeing to take on their issue. But your response to their answer might be, “Thank you for your trust in sharing that with me. What do you want me to know about this? And how can I be supportive?”

Asking good questions is as much art as it is science. It is a continual experiment of asking what you believe are good questions, experiencing the wide variety of reactions and responses, and learning to refine your approach based on your style of communication, the diverse people you interact with, and the unique circumstances. 

Additional resources

• Communicating with emotional employees. These strategies can help you have supportive conversations with employees and avoid triggering negative reactions.
• Psychologically safe communication and collaboration. Check out these actions and resources for leaders to improve communication and collaboration. Learn how to support each employee's success.
• Strengthening leader skills. A variety of activities are provided to help leaders strengthen their skills in the areas of communication, team building and emotional intelligence.
• Are you an inclusive leader. Learn how you can assess and take action to ensure diversity and inclusion.
• Discussing difficult topics effectively. It’s likely that at some point managers will need to discuss difficult topics with employees. Whether the issue is related to job performance, work ethic, appearance or behaviour, addressing topics like these may be a challenge that causes hesitation in some managers.
• Performance management. Resources for supporting performance in a psychologically safe way, even when mental health is an issue. These strategies focus on solutions that also support employee well-being.
• Courageous leadership. Tips to be a more courageous leader and develop a team where psychological safety supports openness, cohesion and success.