100 Questions is Sharpening the Axe


Axe, by: Michael Mongon

Give me six hours to chop down a tree and I will spend the first four sharpening the axe. - Abraham Lincoln

We’ve all heard Abraham's quote a dozen times. It’s all over the internet to the point where it almost seems made up. Whether it is or not isn’t too important. It’s a relevant quote for doing anything well today. 

It encourages you to prepare for the projects that you take on. Preparing projects takes understanding what that project is, what it entails, and most importantly what the success of the project is. To understand a project there is no better thing to do than ask questions.

Who can answer the questions?

Asking questions is part of what’s usually called a project discovery. This is when you should have a room filled with people smarter than you, if you are the egotistical type, at least bring in those who have been identified as the experts and stakeholders. It’s not always something I’ve seen replicated, but this should also be where you bring in your engineers and builders.

This can mean that the room is overfilled. If you are picking the invites make sure to either schedule ways for people to break out and solve specific problems in groups or reduce the invite list. A good rule of thumb is that past 5 individuals, not everyone is actively participating.

Finding the right person to ask questions to means identifying an individual who possesses the relevant knowledge, expertise, or experience to provide accurate and helpful answers to your inquiries. Think through what some of your questions are before you start to help you identify who these individuals are. These people should have a deep understanding of the subject matter and be able to offer insights or solutions that address your specific needs or concerns. Additionally, the right person to ask questions to should be approachable, willing to listen, and capable of effectively communicating their responses to help with your understanding.

What is a good question?

Before any good discovery, all parties need to have done some research of their own. This means you have to start finding the gaps in your knowledge. Those caps are what help you make a good question.

Let’s be honest, even a handful of bad questions can get you along the way. I like to start listing out every question, even the ones I think I can answer because this will allow me to challenge my assumptions with the stakeholders. We all bring bias to a project so even if it feels like a bad question, it may be worth asking.

However, crafting a good question takes time. These are several factors I believe add clarity to finding relevance and being effective in question crafting:

  • Be Clear and Specific: Clearlity is supreme. Do everything you can to avoid ambiguity. Provide enough context of your perspective so that the recipient understands the question and can provide a relevant answer.
  • Define Your Purpose: Sometimes to avoid ambiguity you need to state why you are asking the question. Explain your goal or objective of your question. What problem are you trying to solve?
  • Ask Open-Ended Questions: It’s sometimes worth taking the time to get past the “yes” and “no”. There is a lot more that you can learn from a story told.
  • Avoid Leading Questions: Don’t frame questions in a way that suggests a desired answer. Keep your questions neutral and unbiased to elicit honest and objective responses. This is the hardest because as humans we bring a bias and often answer in a way they think people want to hear.
  • Use Plain Language: Keep your language simple and easy to understand. Avoid jargon, technical terms, or complex language that may confuse the recipient. If this can’t be helped, take the time to explain it.
  • Be Respectful and Courteous: Phrase your question kindly, especially if you are seeking information from others. Show appreciation for their time and expertise. Focus on when they have reached the limit of answering. Everyone has a limit to how long they will answer questions.
  • Consider Timing and Relevance: Ensure that your question is timely and relevant to the context or situation. Avoid asking questions that are unrelated or out of place.
  • Listen Actively: After asking your question, actively listen to the response and be open to different perspectives or viewpoints.
  • Follow-up for clarification: My favorite part of questions is how often good information can make a curious mind find new questions. These aren’t always ones you can prepare for but help give the questioner more background and understanding.
  • Storytime

    It’s difficult to not still make the same mistakes. We’ve all done it numerous times without knowing and most notably I make this mistake with doctors during checkups. It’s usually just a simple question when asking about a bum ankle, an old injury, “So I should exercise 2-3 times a week?” The doctor will always answer, “Yes, 2-3 times a week is good.” while continuing to read the chart.

    Did you see the mistake?

    Here’s the problem. I’m asking because I want my ankle to get better. On cold mornings it doesn’t always work great, and I asked a leading question about health. The doctor was focused on something else and wasn’t paying attention to why I was asking. The doctor provided good information, you should exercise multiple times a week for a healthy lifestyle, but it’s not going to fix my ankle.

    Some people would blame the doctor for bad information. Finding that information properly though is in each of our hands.


    Asking questions can help us be more active in our learning and understanding. There are never enough questions to ask for the curious-minded. However, finding the right questions is hard. Take the time to prepare for what you want to know in the way that Abraham Lincoln sharpened his ask. When you know enough, it makes chopping the tree so much faster.