Ten Questions to Keep You on Track This Year

Posted 01.23.2024

This is the time of the year when I spend a day with my C-suite clients to give them some space to get up on the balcony to consider what success will look like 12 months from now and what they and their teams need to focus on to make those outcomes more likely.

While the process varies and is customized for each executive, there are some core questions that I almost always pose. Over the years, they’ve proven to be useful in helping leaders align their time and attention against the outcomes that matter most.

Here are ten of the questions on my core list. While I recommend working with a coach or trusted advisor who will ask follow-up questions, take notes, and help you see the patterns in your answers, taking some time on your own to reflect on questions like these can make a big difference in defining what success looks like this year and keeping you on track towards reaching those goals.

Here’s the list:

  1. Looking back at last year, what are you proudest of? Challenged by? Most encouraged about? Surprised that it happened or didn’t happen?
  2. If you project yourself out to New Year’s Eve of this year and you’re feeling great about the way 2024 has gone, what are the professional and personal headlines that make you feel that way?
  3. For what and how do you want to be known for this year? What’s on the short list of words that best describes that picture? What are the intentions and what’s in the plan for articulating, exhibiting, and refining those characteristics?
  4. What are the highest and best uses of your own time and attention this year? What are the big rocks that will matter most this year? What rocks will you drop or reduce to make room for the more important rocks?
  5. What are your key communications themes for this year and the best ways to get them across? What audiences do you most need to engage?
  6. What are the personal leadership levers you want to use the most this year? (e.g. your team, wholesale and retail communications channels, key strategic initiatives and themes.)
  7. How do you want to leverage and enable your leadership team this year? What needs to be different this year given the results you’re trying to achieve?
  8. What are or should be the leadership cultural watchwords for 2024?
  9. What’s the optimal cadence and purpose of meetings with your team and other key internal and external stakeholder groups?
  10. Based on your lessons learned from 2023, what are your keep, start, and stop doing personal routines for self-management this year?

None of these questions are particularly profound. The power comes in asking them, giving yourself space to reflect on the answers, and creating a roadmap for how you want to approach your year as a senior leader.

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