Tony Robbins often says, “The quality of your life is the quality of your questions.” My friendly edit would become, “The quality of your leadership is the quality of your questions.”

On key milestones in life, we often find ourselves asking the big questions: “Do I actually make a difference? Where are my relationships going? What do I want to accomplish? Am I leaving a legacy that matters?”

What separates good leaders from the rest of the pack is that leaders don’t wait for milestones. Leaders ask themselves these questions daily. Leaders take time to consistently evaluate their progress and make adjustments as they go.

One key to great leadership is establishing a feedback system. Determine your goals for each day, evaluate your performance, and then reflect on the overall progress from week to week. Having goals won’t yield results if you’re not frequently analyzing your progress toward them. Practicing self-reflection often helps you understand what’s working and what’s not.

Ask Active Questions

There’s a particular type reflection that’s most effective: Asking Active Questions. President John F. Kennedy best teaches us the difference, “Ask not what your country can do for you, ask what you can do for your country.” While passive questions focus on what external factors are influencing us, active questions direct attention to what we can impact.

For example, let’s say your goal is to spend more time with your friends and family. You often find yourself drowning in work and miss out on being there for your loved ones. Instead of asking “Why does my boss give me so much work to do?” or “Why does traffic have to make me so angry?” ask, “What can I do to work more efficiently?” or “What type of music or podcast can I listen to during my commute that would cheer me up before I get home?”

Asking active questions will help you take responsibility for your actions. Shifting your perspective to focus on your own abilities will empower you to take control of your life.

Establish Intervals

It’s particularly helpful to pause and reflect at pre-determined intervals. This purposeful repetition develops mindfulness, proactive focus, and continued growth.

Integrating the habit into your existing routines will make it easier to be consistent. You can find triggers at the beginning of the day, the end, weekly, monthly and annually. Sometimes, the best triggers stem from our weaknesses.

Beginning of Day

This timing of questions is particularly important for establishing priorities for the day. Taking the time to think ahead pays dividends in increased focus all through the day. And in making sure we’re purposeful, not just “busy.”

  • What matters most today?
  • What do I want to accomplish today?
  • What could interrupt me today? How do I prevent that?
  • What would I like to learn today?
  • What am I thankful for today?

Possible Triggers:

  • Brushing your teeth
  • Eating breakfast
  • Driving to work
  • Getting to your desk

End of Day

In Triggers, Marshall Goldsmith calls reflection one of his four “magic moves.” He recommends six specific questions to ask at the end of the day:

  • Did I do my best to set clear goals today?
  • Did I do my best to make progress towards my goals today?
  • Did I do my best to find meaning today?
  • Did I do my best to be happy today?
  • Did I do my best to build positive relationships today?
  • Did I do my best to be fully engaged today?

Golfer Ben Crane recommends these questions at the end of each performance.

  • What did I do well today?
  • What did I learn today?
  • What am I going to adjust based on what I learned today?

Possible Triggers:

  • Winding down at the office
  • Walking to the car
  • Eating dinner
  • Brushing your teeth
  • Getting in bed


For his weekly review, Sebastian Marshall focuses on three key questions:

  • What went right?
  • What would I do differently?
  • What environmental factors influenced me?

In Weekly Essentials, I shared the BAR method that I use:

  • Big picture – What main adjustments are needed? Are goals and projects on track?
  • Actions – What actions are needed? Who can do them?
  • Relationships – Am I making the time for the key people in my life? Is each of my teams set up for success?

Possible Triggers:

  • Finishing work on Friday
  • First thing Saturday morning
  • Sunday after Dinner


If you struggle with finding time for weekly reviews, perhaps dedicating a day each month is an alternative that could work. It’s a particularly helpful interval for assessing trends. (Or, I like doing this even when I am consistent with my weekly reviews. Back when I was a practicing CPA, I carved out time for this in the week after finishing our monthly financials.)

  • Which goals did I accomplish?
  • Which goals did I not accomplish?
  • Were there certain patterns from week to week?
  • How far have I progressed toward my annual goals?
  • How should I adjust for the next month?

Possible Triggers

  • Planning the first or last day of the month
  • Paying monthly bills
  • After a recurring monthly meeting or project
  • Stocking up on supplies at the store


Chris Guillebeau famously creates a comprehensive checklist to conduct an annual review.

  • What went well this year?
  • What did not go well this year?
  • Did I achieve the goals I set last year or not?
  • What are my new goals for health, travel, finances, relationships, etc?
  • What are the required actions I need to take to accomplish each of those goals?”
  • What is the theme for this year?

Possible Triggers

  • Your Birthday
  • New Years
  • An Anniversary

Is it worth the time?

Looking through the list, that’s a lot of questions. It’s fair to question whether this extra effort matters.

The studies prove it does. In Return on Character, Fred Kiel illustrates that character-based leadership achieves nearly 5 times the return on assets. His “virtuoso CEO’s” invested significant time in their keystone habits.

And I don’t think you’ll need a study to be convinced. Try out the morning questions for a week, or pick just one to get started. Write it on your bathroom mirror, in your car, or on your desk, and think through your priorities for each day. Pick three and write them down. I’m betting you’ll feel a difference almost immediately.


photo credit: flickr/phild41