The importance of reflection in Customer Success and beyond

To quote Ferris Bueller, “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.” Most of the leadership podcasts and articles I’ve looked at lately stress the need to reflect on what you’ve done and be very mindful about you are going to do. Setting aside some time and leveraging technology can provide the necessary focus you need – especially if you are in Customer Success and/or in a leadership role. There are so many different things coming at you both in your professional and personal life. Are you ready to tackle them? Are you prioritizing the right things?
To facilitate my reflection time, I’ve found a free mobile app called Grid Diary that does the trick. It asks the questions that forces me to take a step back and think about what matters most in my life: where I’m spending my time, how am I staying healthy, what is my state of mind etc… To ensure that I actually fill out my journal, I’ve set a recurring time in my calendar every day (even on weekends). Do I actually do this every day? No, but I do it enough so that it’s become a habit and is meaningful. I take a few minutes on my morning commute to work on this and now it’s become part of my daily routine. I had to experiment to determine what the best time was for me to do this. You’ll need to do the same. I found that I love coming into work with my brain primed and ready for what will come at me.

What are you going to get done today?

Out of all the questions I answer in my journal, I like this one the most: “what am I going to get done today?”. It helps me narrow down the 1-2 things that I want to accomplish – no matter what.
Below are the grid of questions that I use. Daily Grid has a bunch of canned questions you can use or you can create your own. This will provide you with some ideas on what you might want to track in your journal. This takes me 5 minutes to complete at most. I also only answer some of the questions but I have a few of them that are “must do”.
My Grid Diary
The Grid Diary I use for daily entries to reflect on the day before and focus for the day.


Here are a few sample questions:
  • What did I do with my family yesterday?
  • What could I have done differently yesterday? I think about where I can improve. It’s why I like to seek out feedback from others.
  • Who did I give thanks to yesterday? This goes beyond my job. I think about friends, family, colleagues and people who I randomly meet during my day.
  • What am I most proud of from yesterday?
  • What is my One Thing? This is from the book “The One Thing” which I highly recommend. It helps keep me focused.
At the end of the week, I do a weekly reflection in Evernote by reviewing my daily recorded items and asking additional questions:
  • What am I most proud of this week?
  • Where could I have done better?
  • If today was my first day on the job, what would I do differently? This came from Andy Grove and High Output Management.
  • Who did I learn more about this week? 
  • Who do I want to learn more about? This is especially important as you build out your network which I further discuss in this post on Customer Success leadership.
  • How did I manage up this week? How could I have done better? This should be done at all levels.
  • What am I doing to make my future life better?

“We need to celebrate the first downs and not just the touchdowns”

Why would I take the time to do this and not just listen to some music on my commute? This daily practice of writing in my journal forces me to pause and freeze time if only for a moment. I really do try and look around once in a while.


For example, when I ask myself “what am I most proud of?” it allows me to celebrate what I’ve accomplished – no matter how small a victory. This is something we don’t do enough of – especially in Customer Success. I say this a number of times to my team “we need to celebrate the first downs and not just the touchdowns.” This may mean celebrating a compliment from a customer rather than just reviewing if our retention rates have increased quarter over quarter. I’ve even started a contest to have my team record their micro success stories in a slack channel so we can all celebrate these small wins.


Success doesn’t happen overnight but if you take the time to focus on what provides the highest leverage, celebrate the small wins, thank the people around you and learn from your mistakes, you have a better shot than most to get the most out of your role and of your life. While I’m far from being great at this, I do find that it helps me with the challenges I face today and those that are on the horizon. What are you going to get done today?


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