5 Questions to Stop Asking Your Employees Now (and What to Ask Instead)

Leadership Coaching
12/03/20 - Jennifer Maynard

Questions are one of the most powerful (and important) tools in a managers tool box. As a coach, I work with leaders for days, weeks or months on end specifically around questions. Think back to a leader you had in the past that you thought was really great. What types of questions did they ask you? Think back to a leader you had that wasn’t great. Same question, what types of questions did they ask you, or did they ask you any at all? A leader that asks powerful questions will have a much larger impact than a leader that asks bad questions, or worse, no questions at all. Today, we’re going through what questions to stop asking, and what to start asking instead.

Deep questioning is one of the key pillars in our Elevate program that we work on with leaders as questions are a foundation to a strong relationship with your team. 

Questions to Stop Asking

  1. Yes/No questions – these don’t allow for open dialogue, only simple and short answers.
  2. Asking why? – The word “why” has a very negative connotation to it. If you say: “why did you do that”, “why did you make that choice” it often feels as if we made a mistake or the wrong choice. It carries a heavy negative burden.
  3. Leading – These can be tough as they force our employees to answer in a way we want, which may not be the reality for what is going on. 
  4. How can I help you? This is too vague and implies the employee is helpless.
  5. No question at all. By just giving solutions, assuming, or answering for others we are doing a huge disservice to our people. Choosing to not ask a question, is the biggest mistake of all. 

Turning Bad Questions into Good Ones

Yes/No questions

The problem with yes/no questions is that they only allow for short answers and don’t let us get a true understanding of what is going on. If you ask 5 yes/no questions your conversation may be over in 15 seconds. But if you ask 5 open ended questions you could talk for an hour. An open ended question will give you a better understanding for what is going on and how you can support. If you are stuck shifting your yes/no question to an opening ended question think about the answer you’re trying to get from your employee then flip that around into a question.  Instead of saying: “Are you going to that meeting today?”, ask them “What meetings are you planning to attend today?”.  Or to go deeper “Are you happy?” can be “What’s something that’s going really well for you today?”


Why is the most important word to avoid as a manager, leader or coach. The word “why” has a very negative connotation. I always tell clients, you can ask why to yourself, but don’t ask it of others. You can encourage them to ask themselves why, but this is one of those questions to stop asking. Asking “why” implies we did something wrong. Why did you do that – says you did it wrong. Why would you choose that – says you made the wrong choice. Find ways to ask why without using why. Instead of “why did you make that choice” you might try “Tell me about your decision to choose option A over option B”. 

Leading Questions

It can be useful as a manager to use a leading question when an employee is truly stuck and you need to help them arrive at the right conclusion or action. In reality this is a very small amount of the time. If you are constantly leading your employees down a path they will never have a sense of ownership and they will know that you don’t trust in any solution but your own. If you want them to feel like their decisions have value you need to let them make some on their own.

One of my favorite examples of a leading question to avoid goes like this: “Personal development is highly valued at this company. Those that work on their personal development are better employees. Would you like to discuss your personal development goals today?” In this example you’ve set the employee up with no choice but to say yes. If they say no they are going against the company, what you as a manager value and making it known they aren’t a good employee. When in reality maybe they are burnt out and don’t have time to focus on personal development?  

How Can I Help You?

HELP – the scariest word to an employee. How can I help you implies I am helpless. If you ask me how you can help me, I will be on the defensive and assume it means you don’t think I can do my job. Sadly if you are asking this question to an employee, they likely really need your help, and may not be able to see it for themselves.  But we need to be cautious and ask the question of how can I help you a different way.  It might look like, “What are some of the challenges you’re experiencing on this project?” or “Are there any roadblocks I can remove for you to allow you to be successful?” Just think of a creative and more specific way to ask the question and avoid adding in the dreaded word, HELP.

No questions

The worst thing you can do is avoid questions. Just start small and simple. Take notes before conversations and brainstorm what some possible questions might be. Or start with my favorite non-question, “tell me more”. Take a couple of minutes and watch this video on questions to avoid and see if you gain any new insights.  

We hope this list of questions to stop asking helps elevate your team and communication. Remember that asking the right questions is one of the best tools in your leadership tool box. What questions will you remove from your current process and which will you add?

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