Take Your Questions From Good To Great: 15 Examples

Ask Better Questions

What questions do you use most often in your work?

You may be focused on squeezing out incremental gains – how can we process 2% more transactions per day through this system? In some cases, that type of question is just right. If you’re working on a banking system that manages two million daily transactions, then incremental gains are valuable. What if your project objective is to create a brand new product? In that case, you need different questions to become more productive. Where do you get started? You need to identify your ineffective questions.

Do You Use These Bad Questions?

Here are some of the bad questions that I see come up in the working world.

1. Who’s your boss?

This is usually a sign that somebody is angry at you and wants to go over your head to lodge a complaint.

2. But how would we pay for that?

This question can be helpful but it is often used as a way to shut down discussions.

3. Couldn’t you just try harder to fix this problem?

Hard work has a role to play. However, if you systematically rely on heroic efforts to get everything done, your organization is dysfunctional.

Fundamentally, those questions don’t prompt meaningful engagement or bring new insight to the table. Now that we have those points out of the way, let’s turn to better questions.

5 Questions To Ask When You Start A Project

Starting a project on the right note is critical. How else will you be able to motivate the team to engage on the project?

1. Why are we doing this project now?

Timing matters! Asking questions like this are one way to boost your business acumen.

2. What is the history related to this project?

Learning from history is a powerful skill. Historical points to explore – are there any other past projects like this? What is the project experience of the person sponsoring the project?

3. Who is the project’s champion and why?

In most large organizations, there is ultimately a single champion, executive or manager who is accountable for the project. If piss off the VP, you’re going to be in trouble even if the project is on schedule.

4. What can I get excited about on this project?

The project team looks to you – the project manager – for leadership. What can you get excited about on the project?

5. How can I better understand the sponsor’s needs and expectations?

Start by finding out how they want to hear from you. Do they want detailed spreadsheets by email or high touch phone calls? At the start of the project, ask how they want to hear from you.

Five Questions To Ask Advice

In project work, you’re constantly doing new activities… And that means you’re probably having to figure out new applications, systems and processes. You can get better support from your peers and mentors if you ask them a few focused questions.

1. What are the most common mistakes you see beginners make?

This question is adapted from Tim Ferriss’s excellent book Tools of Titans. You can apply it to project work in all kinds of ways. For instance: “what mistakes do novices make when it comes to presenting to the management committee?”

2. What resource was most helpful to you in learning this skill?

Even if you have a great mentor, they have limited time and energy to help you. If you’re seeking advice on how to learn a complex skill (e.g. “how do I improve my public speaking skills?), seeking a resource recommendation is the way to go.

3. How can I practice this skill in a low risk fashion?

Low risk practice is essential to developing a skill. As Eduardo Briceño explains in his TED talk How to get better at the things you care about – top performers look for ways to practice and improve. For instance, highly successful comedians are known for trying out new material on small audiences. That way, they will have quality material to present to large audiences.

4. Who can I observe in action to learn how to do this?

For some skills and capabilities, it’s valuable to watch a master at work. I’ve picked up tips and tricks to use Microsoft Excel better by watching others manipulate complex spreadsheets. I’ve also learned some blog writing techniques by studying the work of other highly successful bloggers.

5. Can you give me feedback on this small task or deliverable?

Let’s say you have a presentation to the CEO tomorrow. With the right approach, this presentation has the potential to supercharge your career. For high stakes opportunities like this, ask a mentor if you can practice with them. Remember to ask them to provide feedback and suggestions. Use the Starter Feedback Model as a resource to guide the person in providing useful feedback to you.

Five Questions To Ask For Problem Solving

When you’re leading a project, there is a steady stream of problems. Use these questions to better define the problems and develop solutions.

1. Do we have the facts about this problem?

You may have a vague sense that something is wrong. That’s not enough to take action. You need to gather examples and facts before you make a move.

2. What other ways could we state the problem?

The wording you use to define or describe a problem matters. Let’s say you’re concerned with profits. One way to state the problem is “How can we cut expenses?” A better question might be to ask, “how can we earn more orders from our past customers?”

3. What other causes are at play for this problem?

When a problem occurs, it’s easy to fixate on easy to understand aspects of it. As Taylor Pearson recently wrote, we have a bias toward easy to understand problems and situations. If a problem is easy to measure with an accounting system, it’s easy to focus on financial aspects to a problem. However, fixating too soon on a single cause may lead you down the wrong path.

Resource: Read Pearson’s excellent essay The Illegible Margin: Profiting From The Gap Between The Map And The Territory for more insight on this issue.

4. How could we solve this problem if we have no money available?

Many project problems are easy to solve when you simply spend more money on them. On the other hand, that approach sometimes encourages lazy thinking. Use this question to search for other solutions. For example, rather than hiring an external consultant, could you call 20 people at your company and ask if anyone knows a developer who can help you?

5. What other mental models can we use to solve this problem?

Mental models describe the assumptions, ideas and related concepts we use to look at the world. As James Clear explains, having a variety of mental models available is a key way to boost your problem solving ability.

Resource: To dive further into mental models, read Creating a Latticework of Mental Models: An Introduction from the excellent Farnam Street blog.

Where Can I Learn To Ask Better Questions?

“Questions are your pickaxes. Good questions are what open people up, open new doors, and create opportunities.”

– “Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers,” by Tim Ferriss

I love long form podcast interviews because they represent a special opportunity to explore a topic in depth. Here are some podcasts, articles and other resources to help you sharpen your question abilities.

Testing The “Impossible”: 17 Questions That Changed My Life. A powerful article from Tim Ferriss (one of my favorite authors). My favorite question: “What if I did the opposite for 48 hours?”

The 21 Questions I’m Asking Myself This Week. Business writer and consultant Ed Gandia uses a list of questions to reflect on his business and plan next steps.

EconTalk. This long running podcast features in-depth interviews with authors and economists. It’s a great example of how questions and conversation lead to greater insight.

How to Ask Better Questions by Judith Ross. This HBR article focuses on questions from the perspective of managing people.

The Quest to Ask Better Questions. The article puts it simply and well – “Questions are sometimes better than answers”


Get The Friday 5 Email Newsletter

Productivity Tips, Resources & Hacks Delivered Every Friday!

Powered by ConvertKit

Please note: I reserve the right to delete comments that are offensive or off-topic.

Leave a Reply

Your email address will not be published. Required fields are marked *

4 thoughts on “Take Your Questions From Good To Great: 15 Examples

  1. I love this post. The power of great questions is underappreciated. Most likely even the act of questioning itself is underappreciated, but this takes the skill to another level. Wonderful post!