5 Open-Ended Questions Every Manager Needs to Know for Powerful Coaching

Are you struggling to get your team to take ownership of solving their own problems, thinking for themselves and seeing projects through until they're completed?

This is a common problem for a lot of managers right now.

And in this episode, I'm going to explain why this is such a big challenge, and I'm also going to teach you a very simple way to fix this so that you and your team can get more done without you having to micromanage them.

First, before we begin make sure you hit that subscribe button. So you don't miss out on any tools, tips, or strategies for leveling up your leadership skills.

Now, if you're in a management position, you were probably a top performing individual contributor earlier in your career. You probably excelled at working on the toughest projects that nobody else could handle. You probably took initiative to solve problems or improve processes, or, figure out how to overcome random challenges and use your resources more efficiently than other people around you or your peers. You probably followed through on things. If you said you were going to do something, you did it, you delivered on it.

If you were not going to be able to follow through on it, you were probably really good at communicating with your boss and your team about where you were running behind. If you were stuck, or if you didn't understand something, you probably were very quick to ask questions that you didn't spin your wheels too long. In short, you paid your dues, right? You were an individual contributor and you figured it out.

So now that you're in a management position and when you see people on your team not doing the same thing you did earlier in your career, like not following your directions. Or not taking ownership of figuring out how to solve problems or learn something new on their own. Or when you see them leaving before their work on a project is done and there's a deadline that day. It must be impossible for you to comprehend these things. Now right, wrong, or indifferent you can't solve these problems unless you understand the root cause of them. Let's quickly take a look at why your team is struggling to think for themselves.

Your Team is Stuck in Their Comfort Zone

Now first, it's a big part of our human DNA. They're probably stuck in their comfort zones. The reason I said this is part of our DNA is because we are hard wired to seek comfort and avoid discomfort. In other words, we're hardwired to seek pleasure and avoid pain. This is why you eat that piece of cake when you're on a diet. It's also why you still keep scrolling through your phone when you know, you should be more present with the people you're around in that moment.

Now I explain this concept in a lot more depth in my episode called How To Escape Your Comfort Zone. It's a two part episode. If you're interested in checking that out. I'll leave a link to both episodes in the description for this one, but I'm going to keep focusing on, how to get your team more productive here.

Now, like I said, we're hardwired to cling to our comfort zones. When you don't challenge your direct reports or nudge them in new directions, the people on your team are going to remain comfortable in doing things the same way over and over again. Even if it's the wrong way, even if they're not improving.

So I know you and me might look at it, like, why would you do something the wrong way over and over again? But honestly, that's what makes you unique? That's what made you successful? And that's what made you excel past your peers early in your career? The average person, doesn't think that way they cling to their comfort zone and unless they have an outside influence, they're not going to break that cycle they're on. Think about like Newton's law. An object in motion stays in motion until acted on by an equal and opposite force or an external force. It's the same here. People just keep doing the same thing, unless there's an outside influence.

Now that doesn't mean being a drill sergeant. That doesn't mean, just driving them into the ground. It means exposing them to new ideas and then getting them to think differently. You have to be careful when you do this because you don't want to push too hard.

Fear of failure and lack of risk tolerance

Because another reason why your team is having trouble with being proactive and thinking for themselves is related to another human DNA thing, which is fear of failure and, being risk averse, or, wanting to avoid that failure making mistakes.

When people work in a workplace culture that punishes mistakes and emphasizes perfection, it's going to discourage independent thinking and initiative because people are going to be playing not to lose instead of playing to win. There's a huge difference between those two things. Now, like I'm saying here, direct reports in this type of culture, they're going to be afraid to ask dumb questions because they don't want to look stupid. They're also going to be hesitant to take risks or venture outside their comfort zone, create new ideas or, come up with an alternate way that questions or challenges, the status quo. They're just going to fall in line and stop thinking independently.

That hinders their problem solving and their ownership. They're not going to take initiative on these things. If you want each person on your team to succeed, you first need to give them permission to fail. This is why it's important for you to be able to demonstrate a lot of patience with your team.

You need them to feel comfortable with making mistakes and you need them to be comfortable with going to for help. Otherwise they won't. They're going to just keep doing the same thing over and over again, because it's more comfortable for them to do that versus the discomfort they're going to feel when they make a mistake by trying something new or taking a chance or telling you that they don't understand something.

Now on the topic of being more patient. This is something a lot of managers struggle with. We're high achievers and we're used to getting things done. So if you struggle with patience, especially when it comes to your team, you want to check out my episode called 3 Powerful Techniques That Will Improve Your Patience and Focus.

Micromanagement and Over-reliance on Instructions

​The third root cause that I want to touch on here is micromanagement and the effect it has, which is basically your team becomes over-reliant on instructions.

As the manager, one of the most frustrating things for you is when you give crystal clear instructions or directions to someone, only for them to not follow it. You tell them step-by-step what to do and then they don't follow it to a tee. This is aggravating. You shouldn't have to repeat yourself. You shouldn't have to follow up with them to make sure that they're going to follow your instructions.

Now as a manager, your intentions are probably in the right place by giving all this clear instructions and over communicating, but it might be hurting you more than it's helping you. When you're constantly supervising someone and when you're giving them detailed instructions, it's actually going to stifle independent thought from them. It's going to stop them from wanting to solve problems on their own.

It's going to create what I call a problem solving dependency, where your direct reports become accustomed to waiting for your guidance and your help and your answers instead of proactively tackling challenges on their own. They're not going to take ownership of anything. They're going to wait for you to tell them what to do. This is what happens and a lot of managers make this mistake. You think you're being a good manager by giving them crystal clear instructions, but all you're doing is teaching them to not think independently.

If they're not thinking for themselves, it means you're going to have to take the wheel and drive them to think differently. You do that by asking questions that they don't ask on their own. The reason you need to do this is because if they don't have these insightful questions that challenge them to delve deeper into something, the people on your team are probably only going to grasp the surface level of your instructions or your tasks and they're not going to really understand the intention behind it. Or the meaning behind it. Or why they need to be doing what they're doing. It's that in between the lines part that a lot of them are missing out on. When they miss this, it really hinders their ability to see the bigger picture, which ultimately prevents them from taking ownership, which is what you want them to do.

So instead, you want to actively coach them. By asking insightful questions. You almost want to be a complimentary part of their brain. They're not thinking of these things on their own, but instead of you telling them what to do, you need to ask questions that kind of get them thinking about problems differently. Get them to tackle things from a different angle.

You can empower your team to take ownership, think critically and become more confident and engaged in what you're doing. They can become more engaged in contributing in team meetings. Just by asking them thought provoking questions.

5 Types of Questions for Effective Mentoring

But this doesn't mean you just ask them any random questions you're not interviewing them or anything like that. There's five specific types of questions you want to ask your team.

When I'm saying this, I'm talking about in a mentoring setting, one-on-one or you're giving them feedback, maybe it's a performance review. These are the times where they're going to be more vulnerable and open to this versus feeling challenged, like you're calling them out.

So what you want to do is build a mentoring relationship with them and you want to just start focusing on asking them questions. I like to consider this in many cases where you're asking them answers, instead of telling them the answer. So instead of telling them, Hey, I want you to do this. You want to ask them a bunch of questions that can guide them to figuring out the answer or the action that you want them to take on their own.

There's five specific type types of questions you want to ask to accomplish this.

Reflective Questions for Effective Mentoring

The first type is reflective questions. The purpose of these is to encourage your mentee to self-reflect and consider their experiences, their values, and their thought process in greater depth, instead of just staying at the surface level.

The value of these questions is that it promotes a deeper understanding of situations, challenges, and motivations, and it helps your direct report connect their thoughts and feelings to their actions. It also helps them expose bias, blind spots and potential biases that they don't realize they have.

Here's a few examples of reflective questions. You could say something like, Hey, you mentioned feeling frustrated with that particular task. Can you walk me through what's happening and how that's making you feel? By doing that, they might not realize why they're getting frustrated at that task. It might be that they don't understand it. Or it might be that no one ever taught them how to do it. Or it might be that maybe they're just not naturally good at that with whatever their skill set is. If they're not enjoying the task, they're just going to keep fighting it. So it's good to ask them questions about, why you're feeling that way. What's making you feel frustrated or what's making you feel like this isn't working.

Another example of one of these questions is, what are your main priorities for this project and why are they important to you? So asking a question like this, encourage them to think about, what's most important about this project, what matters the most. That way they can keep that in front of mind when they're making decisions on the project and they can connect the priorities of the project to something that matters to them as well, instead of just feeling like they're following orders.

Another good reflective question to ask your direct report is tell me about a time when you faced a similar challenge. What lessons did you learn from it? Now the importance of this question is, a lot of times we're busy with our teams. We have tight schedules and tight production deadlines to hit. So we're not really taking that step back to reflect and learn from our past experiences.

It's important to get them to reflect on things like this, because when you think about how learning works, there's really three aspects to learning. The first step is getting feedback. Okay hey, this didn't work. Right? Then the second component of learning is reflection. Okay why didn't this work? What did I do wrong? What could I have done differently? Then the third component is iteration. All right now that I've learned this from this mistake, now I'm going to try something differently to learn it the right way. So there's those three components of feedback, reflection, then iteration.

If you don't get them to reflect, which they're probably not going to do on their own. If you don't get them to reflect, it's not going to stimulate them to think about it deeper and get to that iteration step where they're actually learning and absorbing and trying something different.

That's why reflection questions are great and you can use these in any setting. You can use this in a mentoring session. You can use this when you're reviewing something they did on a project, maybe a mistake, or maybe it's something you want them to do differently next time. You could ask, Hey, we hit this problem on this project, what's something you could have done differently.

These are reflective questions that get them looking backwards to basically look at what they did from a different angle and figure out what could they have done differently.

Hypothetical Questions for Effective Mentoring

The second type of question you want to ask your team is hypothetical questions. You know what ifs. Again, this is to spark creativity. The purpose here is you want to introduce a new perspective. You want to challenge assumptions. You want to spark creative thinking. You want to get them thinking about the things they're not going to think of on their own. That's the purpose of all these types of questions.

The value of these hypothetical questions is that it expands the other person's thought process. It opens their mind to possibilities that they probably wouldn't have considered, which is the catalyst that fosters innovation.

Now some examples of hypothetical questions would be something like this. Let's pretend you have unlimited resources to tackle this problem. What would you do differently? Imagine you could switch roles with your manager for a day. What decisions would you make? Another question you could ask is what are other approaches you could take to achieve your desired outcome?

The beauty of these hypothetical questions is they're really easy to ask. All you're doing is just asking them to think differently. You're just asking them to either put themselves in someone else's shoes. Like asking what would you do if you were in that person's shoes? What would you do if you were that person? How would that change your way of thinking on this? Or what would you do if you didn't have availability to these resources?

You're basically just getting them out of tunnel vision thinking and getting them to think differently about the problem, which is super valuable because you'll notice when you start asking these questions you'll see that light bulb go off. Oh, I haven't thought about that. I didn't realize this.

It's really easy because we are all natural problem solvers. You just got to give someone a different way to think about the problem, and then they'll come up with a different way of thinking about it.

Justifying Questions for Effective Mentoring

The third type of question you want to ask is justifying questions. The purpose of justifying questions is you want to uncover the underlying reasons for the other person's thoughts, feelings, and actions.

You basically want understand why are they thinking this way. Maybe there is a limiting belief somewhere in there. Maybe you're going to find that they have an incorrect assumption or maybe they weren't trained on something. Maybe there's a gap somewhere that needs to be filled and maybe they didn't get trained or maybe they didn't get the knowledge or the background or experience on something.

Basically these types of questions help expose a disconnect somewhere between you and the other person. The value of these types of questions is that it encourages critical thinking as well. It clarifies their decision-making process and it helps them identify their potential blind spots.

So some examples of this, would be asking a question, like what specific evidence or experiences led you to believe this or led you to this conclusion? Ask them to explain their rationale. You could also ask questions like, can you explain the potential benefits and drawbacks of this approach? What are the pros and cons.

Another good question to ask is how might your decision affect others involved in the situation? It's always good to challenge people to empathize with other people because we tend to have a one track mind and not really think, how does this impact other people when I make a decision.

Probing Questions for Effective Mentoring

The fourth type of question you can ask in a mentoring relationship or with your direct reports are probing questions.

Now probing questions, the whole purpose here is to get to the root of what's going on inside their head. Whether it's their motivation or their emotions, or maybe they have concerns about something. You want to probe to figure out what is holding them back? What are the constraints going on? Or what are the things that they're thinking about that are, maybe creating a mental block that are preventing them from doing the thing you want them to do.

Now the value of asking these questions is that it builds trust. You're showing that you understand them and you're showing that you want to understand them. You're not judging when you ask these questions, you're just listening to get their way of thinking and understand what's holding them up. You want to create a safe space for them to feel vulnerable.

When you do this, it's going to lead to a deeper self-awareness in them, but it's also going to help you gain more understanding and awareness about them. You're gonna have a clear understanding of what is their internal way of thinking or what's their internal conflicts. This is super powerful for you as a manager, when you want to influence them and change their way of thinking on something.

Some examples of probing questions are asking a question, like what feelings arise when you think about this situation? What problems are you anticipating? What are you worried about? What do you think is going to go wrong? What challenges do you anticipate? Asking something like that, but then asking them, like, why do you think that will go wrong? Ask them to qualify what their concern is.

Another great question to ask is there anything you haven't mentioned to me that you'd like to share? If you're having a discussion with them about something on a project, or if maybe you're interviewing someone for the job, whatever it is, this is always a great question because people will always be able to think of something that they wanted to say, but didn't, and as long as you're creating that safe space for them, they're going to share that with you.

Again, this gives you way more perspective on how to influence them, because if you don't know, what they're really thinking, or what's holding them back. You're not going to be able to influence them. You're basically having a one-way conversation.

Another great question to ask is there anything you're concerned about if we take this course of action? Asking a question like this is going to draw out, what are they worried about? Why are they holding back? Why are they not doing the thing you're asking them? Or why are they not willing to take ownership of the thing you're asking them to do?

There's a bunch of different angles to do this. These are just some examples to get you thinking about how to ask these types of questions and how to use them with your team.

Checking Questions for Effective Mentoring

The fifth type of mentoring question you want to ask is checking questions. What I mean by that is these are questions that help the other person understand the conversation. You basically want to confirm that they're aligned with what you're suggesting and what your insights are for them. You're basically confirming, it's like a round trip or a feedback loop. You want to make sure there's mutual understanding so you leave on the same page.

The value in doing this before you break off from a session with someone is you're clarifying your communication. You're making sure that there's no misinterpretations. Doing this builds a shared mutual understanding, and it creates a good feedback loop for you to build on

Now I actually explain how to do this at a way deeper level in my episode called How To Make Sure Other People Listen And Understand You. I'm gonna include a link to that episode in the description to this episode. I'm going to stay high level here, but you definitely want to check that one out cause I go through a technique called the empathic listening cycle. It's a great way to draw out, if the other person didn't clearly understand what you meant.

Some high-level example questions of checking questions are, Hey, did what I just said resonate with you. Did that make sense? You could also ask questions. Is there anything I haven't addressed that you have questions about?

Again, a lot of the time people aren't comfortable with asking questions because they don't want to look dumb. They're embarrassed to ask a question that, is a stupid question. But if you basically give them that opening. Hey, is there anything I didn't cover? Is there anything you're unclear about? That's going to give them safe space to feel comfortable with asking that stuff.

Another great question to ask. What are your key takeaways from our conversation today? Now not only does that check to make sure you're on the same page where their takeaways match, what you wanted their takeaways to be. But another thing this does is. It helps them think about the thing you guys just talked about one more time before they break off, which is a memory trick for helping them make sure they remember it.

A lot of times we receive information and we're listening. But we didn't do anything with that information in our brain. So it just goes in one ear and out the other. But by asking someone to think about it one last time before you break off, it's actually a memory trick that gets them to lock that information in their brain and absorb it better.

Bonus Tips for Effective Mentoring

Now, before we break off, I want to give you a few more bonus tips on how to do this. When you're formulating these questions you want to consider the other person's stage in their development? You want to consider their personality, their current situation, are they working on something, are they new? Are they going to be sensitive about a certain topic? Are they going to be comfortable with you? Do you have a strong relationship with them? You want to think about all these things and take them into account.

You don't want to start off too strong if this is someone that you don't have a strong relationship with. But if this is someone you know, pretty well, then maybe you can probe a little bit deeper right away. So you just want to take a step back and think, what is my relationship like with this person?

The next thing you want to do is you want to be open-ended. You want to listen actively and you want to adjust your approach based on their responses. So don't go in with a scripted set of questions. Instead have just some of these formulaic questions in mind that you can go to. Why, what, how, when and where, these follow-up questions that get them to think with these five types of questions that we just went through. You don't want to go in like an investigative reporter instead you just want to ask a question, encourage them to talk, and then just actively listen and respond based on what they share with you.

Remember effective mentoring questions are not just about testing the other person's knowledge or giving them the answer. Instead, what you're trying to do is guide that other person on their own journey of self discovery and learning. Then you want to help them think about the problem from a different angle so that they absorb the information differently and they don't get so tunnel vision on it, and they can think differently about it.

But with all this in mind, you're not going to be very effective at asking great questions if you're not a great listener. If you're realizing that your listening skills could use some improvement, check out my video called Improve Your Listening Skills By The End Of This Episode.

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