The Personal Retrospective Guide

At the end of every year, I spend the holidays reflecting on my year, what went well, what didn’t go well, and what I can do in the next year to be a better version of myself. I take all of my coaching clients through this process as well. This year, I decided to open-source my Personal Retrospective Guide so that everyone can benefit.

These are weighty questions, and they aren’t meant to be answered in one go in between meetings. They’re meant for walks on the beach, quiet moments where you can really zoom out and see the big picture.

What’s the purpose of reflection without action? The goal for each section is to create commitments to improve and grow yourself, your team, and your business. At the end, you should walk away with a concrete strategy and goals that will lead you to success.

The Executive Summary

The first few questions are meant to scratch the surface. They’re an appetizer, if you will, before diving into the main course.

  • What accomplishment from this year are you most proud of, and what lead to that accomplishment?
  • What was one major disappointment, and what could you have done to avoid it?
  • How do you feel you’ve grown the most this year?

Take this opportunity to appreciate what you’ve accomplished, and identify the big milestones. Compare where you were at the beginning of the year to where you are now. Reflect on your biggest mistakes, but with the resolve to not let it happen again.


Our lives are constantly changing, as do the demands placed on us by our business. We should regularly reflect on the skills and activities that got us to where we are today, that won’t deliver the most value in the next phase. Let’s identify some areas where you aren’t aligning your time investment with the value it brings to your business.

  • What tactical work has been taking up much of your time that you know you should get off of your plate?
  • What are the most valuable things you know you should be doing, but aren’t spending enough time on?
  • What skills or responsibilities does your team or your business need from you that you are not delivering to the highest level?
  • What is an area where, if you executed flawlessly, would bring the most growth to your business?

Now, write a simple vision statement, describing yourself at the next level of growth. Describe how you focus your time on what the business needs, and the impact that it creates to your customers, your team, and yourself.


Leading an organization is a great responsibility, and we owe it to everyone in our organization to show up in the best way possible. Growing as a leader requires that we constantly invest in learning, working on our emotional intelligence, and developing the next generation of leaders in our team.

  • What leadership and support does your team need from you that you aren’t giving them?
  • Who on your team needs your support to grow as a leader?
  • What do your peers and leaders need from you that you aren’t giving them?
  • What is the most critical area where you need to grow as a leader, and what can you do in the next year to get to the next level?
  • What is one major organizational problem that would unlock the most potential in your team?

Now, write down your commitments to grow as a leader. Describe how you will show up better for your team, how you will invest in your own leadership skills, and how you will guide your team to unlock their next level of growth.

Personal Life

The foundation of our success is not in business, but in our personal lives. We must take care of ourselves and our loved ones, and we must find balance in our lives, or we will burn out.

  • What was your most memorable personal experience from this year?
  • What activities outside of work give you the most joy and fulfillment?
  • Who do you care about most in life? Name them.
  • What aspects of your health do you feel need to be taken more seriously?

Now, write down your commitments to yourself and your loved ones. To what or whom do you commit to investing more time and energy into that would maximize your health, joy, and fulfillment?

Next Steps

I hope by this point you’ve had many poignant and impactful conversations with yourself, and you’ve made some strong commitments to being better this year than you were last year.

Turn those commitments into concrete goals, with clear objectives and due dates. Set a monthly reminder in your calendar to review your commitments and goals. If you would like to take this survey yourself and keep a copy of your responses, you can take the survey here:

Now that you’ve laid out a strategy to be the best version of yourself, you need to follow through. That’s where I come in. As an executive coach, I can help you clearly articulate this strategy, turn it into concrete, achievable goals, and be there with you every step of the way to ensure you’re staying on course. If you’re interested in seeing what this looks like, reach out and connect with me!