Leadership Reflection and Planning for 2024: A Comprehensive Guide by CultureShoc

As we stand at the crossroads of the old year and the new, it’s a great time to start a habit around calendaring time for Clarity Breaks – a dedicated time for introspection and foresight. This is not just an exercise in reflection; it’s a chance to clear the mental fog, to recalibrate our inner compasses. It’s about stepping back from the daily grind to gain a fresh perspective on where we’ve been and where we’re headed. The Clarity Break is a pivotal practice in maintaining a Learner Mindset – an acknowledgment that our journey is one of continuous growth and adaptation. It’s an invitation to remain open, curious, and eager to learn from both our triumphs and our trials.

In this process of reflection and forward planning, a key area of focus is the development of Emotional Intelligence (EI). Emotional Intelligence is the underpinning of how we navigate our relationships, both professional and personal. It’s about understanding and managing our own emotions, and equally, recognizing and influencing the emotions of others. Developing EI is essential for effective leadership, building strong teams, and fostering a culture of trust and openness. The best part is, it’s a learned skill. Consider these core components of EI: Self-Awareness, Social Awareness, Empathy, Self Regulation, and Motivation. Now pick one, just one, that you want to intentionally strengthen in the year ahead.

Hopefully you’re now sitting in a coffee shop with a pen in hand ready to do an honest self-assessment. If not, consider printing a copy of this and doing exactly that! By no means are these 20 questions all encompassing, but they’ll surely inspire thought during this healthy leadership exercise.

1. Reflecting on Our Storms

In CultureShoc’s Into The Storm Leaders program, we often talk about facing storms head-on, inspired by the way buffalo charge towards a storm, unlike other animals. This approach minimizes discomfort and leads to quicker resolution and growth. As we reflect on the past year and set goals for 2024, let’s use this mindset to guide our introspection and planning.

• Reflect on the ‘storms’ you bravely faced this year. How did these challenges shape you?
• Conversely, consider the storms you avoided. What held you back, and how can you approach them differently next time?

2. Pausing to Recognize Progress

• We’re our harshest critics, always. It’s still a healthy self-esteem boost to look back on how far you’ve come rather than only measuring forward.  In fact, that next milestone doesn’t seem so far when you consider what you’ve already accomplished. Let that fuel you forward! Check out The Gap and The Gain by Dan Sullivan.
• Where did you make the most progress this past year and what are you most proud of accomplishing?

3. Planning to Win

• If completing this same exercise a year from now, what has to have happened for you to feel 100% satisfied with your progress? Be bold. Visualize it.
• Now what are the biggest obstacles standing in the way and how can you break through them?

4. Owning Gaps and Weaknesses

• Which weakness of yours is most threatening to your goals, that, if strengthened would dramatically increase the likelihood of success?
• How can you take complete ownership of this?
• Do you want accountability from others to follow through?

5. Technical Skill Gaps

• Identify a technical skill gap that, if bridged, could significantly benefit you. How will you go about enhancing this skill?
• This doesn’t need to be a college class. Maybe its committing xx amount of time each month to a YouTube series, seeking out someone who has this skill to learn from, or any combination of things. The trick simply being…identify it and write it down, create a plan to address it, and follow through. Simple but not always easy, right? Consider asking someone else for some positive accountability on this one.

6. Nurturing Important Relationships

• Write down the names of the most important people in your life, including who they are and what value they bring. After that, write down how often you see those people or how often you tell those people what they mean to you.
• Now What? Write them a letter. Seriously. A sincere letter about why you appreciate them and the value they bring to your life, even better if you can offer some support for a pain they’re dealing with. Imagine being on the receiving end of that and you’ll immediately see the upside here.
• Through this process we often realize we’re not investing enough time in our most important relationships. Use this as an opportunity to be more intentional about who you surround yourself with in the year ahead. Check out What’s In It For Them by Joe Polish for an incredible concept around nurturing your E.L.F. (Easy, Lucrative, & Fun) relationships and moving on from more of your H.A.L.F. (Hard, Annoying, Lame, and Frustrating) relationships.

7. Learning from Failures

• I’m sure not everything went “according to plan” this year, right? What are the 2-3 mistakes you made that ended up turning into positives?
• Pausing to connect the dots between failures and the ultimate wins they offer helps put your mind in the right place the next time that failure inevitably occurs.

8. Embracing Ownership

• Were there times that you were quick to blame or defend yourself when something went wrong instead of defaulting to ownership?
• How can you be sure to take more of this approach in the year ahead?
• Watch this quick TedX on Extreme Ownership by Jocko Willink for some inspiration!

9. Transparency About Growth Intentions

• One way to navigate away from entitlement is having a clear enough path defined for yourself that you can confidently share it with others. We can’t expect others to read our minds, so promote yourself by speaking it into existence!
• Who should you be more transparent with about where you want to go and what you’re working towards?

10. Building Trust

• In the first session of the Into The Storm Leaders program we highlight how time is not necessarily the most crucial component in fostering high-trust relationships. We don’t believe you can fake trust, but do believe you can accelerate it by being more intentional, showing vulnerability, and by the depth of the questions we ask.
• Which 2-3 relationships would benefit most from some intentional focus around nurturing trust?

11. Setting Clear Expectations

• So often we assume expectations we set were clearly understood. Reality being, we communicated how we needed to say something rather than how it needed to be received and fail to confirm that understanding. It is ALWAYS the right time to set or reset expectations with someone.
• In which situations or relationships do you need to set clearer expectations and clarify those of another for yourself?

12. Healthy Conflict vs. Artificial Harmony

• Where have you been content with artificial harmony and silence rather than embracing healthy conflict in service of others?
• Which ONE situation will you deliberately frame and embrace healthy conflict in this year?

13. Compassionate Criticism

• We often hold back direct criticism from others in an effort to keep peace. On the surface this might seem selfless, but just below, this approach of Ruinous Empathy is a disservice to those we care for. If we care personally about someone it is our responsibility to challenge them directly, helping them grow, even if they like us a little less in the moment for doing so.
• In which relationships have you held back when the opposite was actually what that person needed? How can you remember to deliver candid feedback with compassion in 2024?
• Check out Radical Candor by Kim Scott for incredible insights on this topic!

14. Living Core Values

• Are Core Values more a part of onboarding and decoration on the break room wall at your company or are you actively using these as a filter for all important decisions?
• How can you better integrate these into your daily decisions?
• For executives, modeling and broadcasting this approach enables empowerment of others, freeing you to focus where it matters most. For emerging leaders, what better way to earn credibility and demonstrate readiness for more than by serving as an advocate in this way.

15. Reflecting on Time, Energy, and Attention (TEA)

• We all have a finite amount of Time, Energy, and Attention, often misplacing it where its not truly deserved and depriving the people or things that need it most.
• Where did you misallocate TEA in 2023?
• Where must you focus more of your TEA in 2024 to realize your goals?

16. Strategic Efficiency with Automation, Innovation, and Delegation (AID)

• Perhaps a path to properly allocating your TEA in 2024 is identifying efficiencies by leveraging AI, Freelance, or Automation.
• Check out this free recorded webinar on these less conventional methods of delegation.

17. Perception and Influence

• How certain are you about the perception others have of you and your influence? Mistrust often occurs when how we perceive ourselves differs from how others perceive us or our actions.
• Who can you seek out direct criticism and feedback from to gain true understanding of the mark you’re marking?

20. Emotional Intelligence Evaluation

• Emotional Intelligence is a learnable skill! Consider these 5 components: Self-Awareness, Self-Regulation, Social Awareness, Empathy, and Motivation.
• In which of these would you consider yourself strongest?
• How about your weakest? What could you do to improve in that area to level up your EQ?

This structured reflection and planning session is more than just a routine exercise. It’s an opportunity to align your inner compass with your true north. By facing the storms of the past and preparing for those ahead with a curious, open, and confident mindset, you set the stage for a year of growth, success, and fulfillment. Remember, every storm you face is a step closer to a clearer sky. Let’s charge into 2024 with courage, purpose, and the willingness to embrace every challenge as an opportunity.

Ready to address leadership and team management head-on? CultureShoc has worked with more than 300 clients across the U.S., impacting more than 35,000 leaders.  Schedule a free consultation to get started today!

Just need some extra motivation to keep these things top of mind in the year ahead? Check out the Into The Storm Leaders podcast to hear more from our team and the clients we work with.