The Right Questions



Those are the beginning of the right questions.

I’ve always subscribed to the notion that we have 2 ears and 1 mouth for a reason (thanks, Dad). Simply put, we should listen twice as much as we speak.

What if we can become better listeners by training ourselves to ask the right questions?

There are 2 types of questions: Open and Closed

Open questions invite the recipient of the question to pause and think, which typically leads to more informative, insightful and thought-provoking answers.

Closed questions ask the recipient to react quickly, typically with a “yes” or “no”.

Think about the last time your friend went on vacation. When they returned, did you ask them “Did you have fun?”, or did you ask “How was your vacation?”. While seemingly the same, they typically will provide very different levels of detail. {Important note: If you’d prefer your friend to not go on for 20 minutes about their Hawaiian vacation while you worked your 9-to-5, which was more like a 7-to-6, I suggest the closed question}.

An open question will invite the recipient to expand. Think of it from a professional standpoint. Imagine you’re speaking with a colleague about an idea. After explaining the idea, you could ask: “Do you think it’s a good idea?” or you could ask “How do you feel about the idea?”. Very subtle, but the 2nd question (How…) is an invitation for your colleague to share more than a simple yes or no. You’ll get more substance, which if you truly care whether your idea has merit, you should be interested in their expanded viewpoint. By asking a closed question, you could be missing out on important feedback that could make your idea stronger or help you avoid pitfalls.

So, how do you do it?

There are a lot of great tips out there, and a simple search would lead you in a lot of promising directions.

My advice: start with your next interaction. Write down 3 open questions you can ask and see where it leads you. Retraining yourself is not easy. We have built decades of habits asking closed questions. If you work at it, you’ll become a better question asker, which will make you a better and more active listener.

Start building the habit, one interaction at a time!

Examples of open questions:

What do you think?


How do you feel about that?

What would you change?

What would you do?

How would you approach this?

What should we do differently?

Self Improvement Books

How to Win Friends and Influence People by Dale Carnegie

Quote: “Remember that a person’s name is to that person the sweetest and most important sound in any language.”

Takeaway: We must interact with people to live a fulfilled life. The more we can understand how people tick, how they make decisions and what’s important to them, the better off we are.

Never Split the Difference by Chris Voss

Quote: “Negotiation is not an act of battle; it’s a process of discovery. The goal is to uncover as much information as possible.”

Takeaway: The best book on negotiation. Whether you’re negotiating with a customer, a landlord, a spouse, or a salesperson. There’s lots of tips, but a few key ones are to ask open-ended questions, be empathetic, and listen more than you speak.

The Slight Edge by Jeff Olsen

Quote: “The journey starts with a single step—not with thinking about taking a step”.

Takeaway: There are things that are easy to do and easy not to do. Do them. You will not see a difference in your strength or body after 10 push-ups. You will not see a difference after a week of 70 push-ups. You will see a difference after a year of 3,640 push-ups. The compounding effect is real.

Atomic Habits by James Clear

Quote: “Habits matter because they help you become the person you want to be.”

Takeaway: Hands down, this is the best book on building habits. James Clear walks through a very methodical approach to building habits. When we remember that our outcomes in life are the results of our habits – we start paying attention. We must challenge ourselves to improve our habits so we can improve our outcomes.

The Happiness Advantage by Shawn Achor

Quote: “Countless studies have found that social relationships are the best guarantee of heightened well-being and lowered stress, both an antidote for depression and a prescription for high performance.”

Takeaway: Success does not bring happiness. Happiness brings success. The most important contributor to happiness are your relationships. Maintain them. Grow them.

Range by David Epstein

Quote: “Struggling while learning is better in the long run to retain information and use it effectively.”

Takeaway: We live in a world that is dominated by a believe that success comes from becoming really good at one thing. We’ve all heard that 10,000 hours of deliberate practice makes you an expert. In fact, those people are the rarities. It turns out, those who find the most success are those who have built up a wide range of experiences and knowledge and can apply them in any setting.

Superforecasting by Philip Tetlock

Quote: “Beliefs are hypotheses to be tested, not treasures to be guarded.”

Takeaway: Those who are in the public view are typically ineffective predictors of future events. Those who can see from multiple points of view, remove emotion and constantly challenging their own thinking are the best predictors. They are superforcasters.

The Power of Now by Eckhart Tolle

Quote: “Realize deeply that the present moment is all you have. Make the NOW the primary focus of your life.”

Takeaway: Our mind’s default is to concentrate on 2 things : the past and the future. We rarely can fully be in the present. Which is strange, because the present moment is all we ever have. Eckhert implores us over and over to come to the present moment. Just be. And enjoy being!

The Almanak of Naval Ravikant by Eric Jorgenson

Quote: “No one in the world is going to beat you at being you.”

Takeaway: An all encompassing guide to wealth and happiness from Naval Ravikant. Naval has spent his life consuming the teachings of philosophers and has tremendous success in the technology & venture capitalist world. The combination of these learnings and experiences make Naval’s viewpoints extremely unique.

Change your email habits

Two habits have completely altered my effectiveness with email communication.

  1. Inbox zero
  2. Batch emailing

For years, the desire to respond as quickly as possible consumed me. Don’t get me wrong, responsiveness is a fine quality. Incessantly checking email every 7 minutes is not. It’s one of the reasons I committed to no email on the weekends.

Below are the 2 tactics I took to change my email habits.

Inbox Zero

No emails should be in your main inbox.

Step 1

Move all emails to archive.

Yes. All of them.

There’s no need for other folders. The sophisticated search functionality of email clients like Outlook and Gmail are robust. If you need to find an email, “google it” in your archive folder.

Step 2

Congrats, you’re at inbox zero!

Step 3

New emails come in. You’re no longer at inbox zero. Don’t fret!

Now is the time to make 1 of 3 decisions:

  1. Archive it. You’ve read it, you don’t need to respond to it, maybe you’ll need it later.
  2. Respond to it. You’ve read it, you need to respond to it. Can you do it in 90 seconds? Great. Send a response. Archive it.
  3. Flag it. You need to respond to it, but can’t do it in 90 seconds. You have 2 options: Schedule a meeting to complete the task or use the flagging function to flag it for later. Archive it.

Step 4

Make these decisions until there are zero emails in your inbox.

Batch Emailing

Now that you’re at inbox zero – it’s time to take control of when you email.

Think of it this way: You decide when your email pulls your attention. Your email doesn’t decide for you.

In order to do batch email, you must create your rules and your batch windows.

My rules:

  1. No email before 9AM
  2. No email after 6PM
  3. No email on the weekends
  4. No email on vacation

My batch windows (schedule dependent):

  • Morning (9am-10am)
  • Lunch (12pm-1pm)
  • Mid Afternoon (3pm-4pm)
  • Late Afternoon (5pm-6pm)

My batch window today was:

  • 9:41am-9:56am
  • 11:58am-12:07pm
  • 3:09pm-3:20pm
  • 5:31pm-5:38pm

Each batch takes ~10 minutes to go through the decisions above: Archive, Reply, Flag.

The 2 other things I will do during this time:

  1. Unsubscribe. Take 15 seconds and unsubscribe to emails you don’t need. Or use a tool like
  2. Check Flags. Filter your email by “flagged” to check on items you’re waiting on from others or things you need to attend to.

You have achieved inbox zero and created your batch windows. Now what?

Commit to it by trying it for a week. It will be hard. You’re unlearning a habit that you’ve reinforced daily for years.

Some friendly tips that helped me:

  • Don’t minimize. Exit out of the email client after your batch window.
  • On your phone: Move your email apps to your 2nd screen, ideally within a folder.
  • Tell someone you’re doing this. Have them hold you accountable.

But what if an important email comes in?

If it’s that important, they will call you.


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Clay Davis