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Do you want to have a superpower?

It’s easier than you think.

What if I told you the power to master new skills, control difficult conversations, control normal conversations, get better at your job, improve your relationships at home and at work and with your peers — was something you already know how to do?

In fact, it’s something you’ve been doing your whole life. And that thing is asking questions.

But just because you can ask a question doesn’t make it a superpower. You’ve got to learn to harness the power of a super-charged question first, before you can pop a cape on and start strutting around the office solving communication crimes everywhere you go.




The power of smart questions

A good question is not just about the right words — it’s also about the right time, the right place, and the right person

Ever asked your supervisor for help with something because you were intimidated by the peer who was really supposed to help you? Have you ever gone to your “nice” boss for feedback because you knew you wouldn’t like what your other manager would say?

Yeah, me too. In fact, I used to do it all the time. I would avoid asking questions because I knew wasn’t going to like the answer, and I would find ways to ask other people so I didn’t have to confront someone I thought would think my questions were stupid or embarrassing or annoying.

What I quickly found out, though, is that this strategy is a waste of time. Of course, I kept doing it anyways because it’s easy, which is why so many of us do it for so long.

But what we always seem to forget is that asking the wrong people the wrong questions doesn’t usually keep us out of the trouble we so desperately want to avoid. Instead, it prolongs it.

Often, you end up asking the dreaded question to the dreaded person anyways, only now it’s later and now they’re annoyed. Or, avoiding the issue causes a whole string of new issues that you now have to deal with — which isn’t really preferable to dealing with the one problem you had before.

So even though asking questions can be scary, it’s really important to do well because it will improve your relationships and save you a ton of time and frustration.


How to find the perfect question

A smart question isn’t just about the words you say, it’s about the answer you get too. You have to know what you need to know before you can ask someone else to give it to you.

Specificity lies at the heart of good questions. So before you ask someone something vague like, “Can you help me with this?”, take a moment to think about what “help” actually means to you and how you can make sure the other person knows exactly what you mean.

I like to run through the five W’s before asking any real question:

  • Who do I need to ask? Who is best suited to give me this information?

  • What do I want them to do? Give me information, take an action, offer advice? What do I want?

  • When is the best time to ask? When do I need to have this done?

  • Where is the best place to ask? Can I make it convenient or more appropriate for them?

  • Why do I need to ask them this question? How can I make this compelling for them, so they are more inclined to give me what I need?

If that seems like overkill, think about how much time is wasted by asking bad questions. How many times you’ve ended up in a 5-minute conversation about something you already knew, or when you’ve had a project delivered not to specification because you didn’t ask for the right thing?

Good rules of thumb:

  • Don’t interrupt someone to ask a question. This means everything from not interrupting their sentence to not interrupting their lunch break. You want their help or opinion, and taking their time seriously shows that you deserve it.

  • If you can, let them know you’ll be asking them a question. Prime them to be ready to say yes. If you catch them off guard, they’re more likely to be frustrated or say no.

  • Ask it in their preferred mode. Do they prefer email or face-to-face? Do it their way, not yours.

  • Come prepared. Know exactly what you want to ask when you ask. Don’t still be working out your ideas when you’re at their desk.

Good questions are specific to the situation, and have a clear goal in mind for the person you’re asking. Your question needs to have a point, whether it is getting feedback, getting help, building a relationship, solving a problem, or even teaching someone else something new.

Here are some of the primary types of questions we all ask, and my very best advice for being successful when asking them.

Questions to get feedback

When you’re asking for feedback, smart questions will help you make the most of the information your manager (or project lead, etc) is giving you. Feedback is a gift — it helps you see yourself and your work through someone else’s eyes — so make the most of it by making sure you get as much clarity and insight at you can.

Remember that giving feedback is often uncomfortable for the person giving it, so they are not always expressing themselves as clearly as possible. If you’re not understanding something they are saying, it’s up to you to lead them to give you the information you need.

For example, if your manager tells you, “I’d like to see you take the lead more,” there are tons of great questions to can ask them to get really specific, solid advice for how to do that successfully.

(Bonus: asking questions shows that you are listening and taking the feedback seriously, which makes the feedback giver feel good. This, in turn, may make them more likely to be more specific and helpful in the future, because they see that you are reacting positively.)

  • Can you give me an example of some ways I could have taken the lead on XYZ project?
  • What does being a leader mean to you?
  • I have this idea for taking the lead a current project: _________. Do you think this is a good idea, or do you have suggestions for how I could improve it?
  • Are there examples of people on our team who do a really good job of taking the lead now?
  • What would successfully taking the lead on a project look like for me?
  • Can you recommend any books, blogs, or mentors that can help me get more information?


Questions to get help

These are the questions that usually seem the smallest, but when asked correctly, can have the biggest results. That’s because when you need help on something, the way you go about asking for that help will have a direct effect on what you receive in return.

Who will you ask? An expert, a friend, a boss, a peer, a celebrity, an online forum?

How will you ask? Will you ask for a specific list of items? Will you ask for advice? Will you ask for general “help” and see what you get?

Asking for help is a critical part of being good at your job. Of course, we all like to solve problems ourselves and be seen as self-sufficient, but when you’re blocked, it’s often a better use of your time to ask a question than to muddle through on your own.

Be conscious of the fact that when you ask for help, you are taking someone away from their own work. Be appreciative. Respect their time by asking at a good time for them, and keeping your questions as concise as possible while still giving them all the information they need. Don’t rattle off an account of everything you’ve tried already and how it made you feel; keep it simple and give them just what they need.

Be sure to tell them what exactly you need from them, when you need it, and how (if applicable) you need it.

  • I have been troubleshooting _______ on my own, but am not making any headway. Would you mind taking a look sometime today/this week? It is/isn’t urgent.
  • Could you tell me where to go to figure out _______?
  • I know you have _______ before. Can you give me ideas for how to start _______?
  • What is a good guide for ______?
  • I have done ______ so far, but now I am stuck. Did I make a mistake along the way, or should I keep moving forward?

Try asking for resources rather than asking them to do something for you. People generally have ideas, and it’s a good way to save both of you time. And if they really want or need to help, they will.


Questions to build relationships

“You can make more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.” — Dale Carnegie

This is a technique that I love. Asking questions is an incredible secret weapon in the world of building relationships, and yet so few people employ it regularly.

People love to talk about themselves. Asking people questions makes them like you, because you want to know about them! And you win too, because you get to build a relationship with someone who now thinks you are awesome, and you get to learn from all their experiences and stories.

This is a great way to build relationships with new people, but also a great way to get to know someone you’d like to be closer to (like a manager, peer, or potential mentor). Schedule a 1:1 meeting with someone you’d like to have a better relationship with, and ask some sincere questions about them. May eye contact, nod, repeat phrases back to them, and watch the tension melt away.

  • What has your career path been like?
  • I have been struggling with _______. Have you ever faced that? How did you handle it?
  • What are your goals for the next year? What are your goals for the next 10 years?
  • How do you see your current role fitting in with your bigger goals?
  • What is most exciting you at work/at home/in life these days?
  • When have you had the most fun at work?
  • What would you most like to see our team accomplish in the next 6 months?


Questions to solve a problem

When you’re part of a team that needs to solve a problem, asking smart questions can turn a catastrophe into an action plan. It’s all about identifying exactly what problem you need to solve, and helping the people around you understand what needs to happen to solve it.

Asking questions isn’t just about getting information you don’t already have. It’s a way to start a conversation, and get people talking about the things they think matter most.

And it’s more effective than just telling people what to do, also. Asking people how best to approach and solve a problem gives you the double benefit of hearing people’s opinions, and having people work their hardest on those opinions because they know they’ll be listened to.

  • Which one of these features/projects/goals will be fastest to achieve? Which will have the biggest financial impact?
  • If we make this change, how will it affect ______?
  • Which of these problems is the most urgent to solve? Why?
  • Have we solved a similar problem before? What were the results? Can anyone on our team who has solved this kind of problem before guide us?
  • How can we break this problem into achievable goals?
  • Who specifically are the key people who can solve this problem?


Questions to teach someone

We all know that getting to an answer ourselves is way more satisfying than just being told what’s up. If you are in a leadership role, this is one of the most important things about your job — helping your team get their work done without just doing it for them. You are there to empower people, and part of that is helping them to realize what they already know.

Even if you’re not a manager, you can use this technique to build consensus on a team or help a peer learn a new skill.

By asking questions, you force someone who needs your help to find their own answer. You’re like a guide; you know the answer, but you’re not driving directly them to it — you are nudging them in the right direction on their own.

Asking questions as a teacher means you have to believe that your student is smart and experienced enough to find the answer on their own. And almost all of the time, your employees are. You just have to trust them, and take the time to invest in their learning by spending a little time coaching and helping them to get there.

Teaching questions help people find their own answers. Some examples include:

  • If you try ______, what do you think the outcomes will be? How can you control those outcomes?
  • Can you explain to me how ______ works, and what impact it has?
  • What would you do for _______?
  • What data do we have from similar projects we have done in the past?
  • How does this information sync with our company goals/mission/values?
  • Who is our customer? How would ______ add value to them? How would ______ add value to our team?


When should we not ask?

Sometimes asking questions makes us feel dumb or powerless, because we are admitting that we need someone else to help us. This can be a hard feeling to shake, but I always find it helpful to go back to the Five W’s — *why* do you have this question? — to remind me that asking this question is important, and so it’s not dumb to ask.

It’s true: not every question is worth asking. Sometimes we have questions we know we could easily solve ourselves if we just thought about it a little longer. So do that! And once you’ve thought about it, and you know that you don’t have the answer but that someone else does, then go ask.

You are empowering yourself when you ask questions. It’s good for you; you’re making yourself smarter. Any question that gets you moving is a good question, so don’t feel stupid for needing help or advice or feedback.

Questions are power. It’s just that simple.

Tags: better leader, communication, improvement, leadership, questions, reflection,

One Response to “The super secret art of asking amazing questions”

  1. Matt

    Thanks for this article. I have issues with speaking, predominantly because I am shy and also don’t always find myself being interested in what others have to say. However, I have realised that I need to become interested to help develop myself and further my career.
    I have saved this article as I am sure I will need it again. Thanks again.