Annual Check-In for Leaders Part 2 — How Are You Doing as a Leader?

When it comes to your leadership, how are things going? How are you doing?

When was the last time you paused to survey how things were going? We’ve crafted a three-part leadership-level survey to help reflect on your team, the company, yourself, and what you’d like to see more of. Give yourself a block of time to journal or work through these questions. Then, take some time to read back through your responses. Where do you notice where you might need support?

In Part 2, we’re sharing some impactful questions to help you reflect on the question: “How are things going for you as a leader?”

Leadership Challenges

What topics below are relevant for you right now? What are the challenges you’re having on the ones you’ve selected? What items would you add to this list?

  • “Impostor syndrome”
  • Time management and prioritization
  • Relinquishing control
  • One-to-many communication and being visible
  • Personal decision making
  • Founder/CEO vision and strategy
  • Maintaining motivation and energy as a leader
  • Personal health
  • Transition
  • Stress management and keeping emotionally balanced
  • Adequate training, experience, and expertise
  • Executive and management team strength, balance, temperament, and overall dynamics
  • Managing through conflict or stylistic differences
  • Other(s): ______________________________________

What’s Ahead?

Assess what you’re looking towards, as you see it now.

  • What are your major deliverables and goals for the next year?
  • In what areas and to what degree is your role scaling in the next 12 months — headcount, products, customers, operations, etc.?
  • Where do you spend your time today, and where do you want to spend your time in 12 Months (both within and beyond your organization)?
  • What will hold you back from focusing on those issues between now and then?
  • What would such successful rebalancing do for you, your organization, and others who matter to you?
  • In your last performance review (or 360), what were your main strengths? What were your areas of development?
  • As a leader, what are the top 3 things that keep you up at night?

You & Your Role

Reflect on the following:

  • How clear are you about the mission of the company?
  • How clear are you about your vision for the company?
  • What is the opportunity (and/or what is necessary) at this time for you in your life?
  • What does success look like for the company? How do you see yourself fitting into that picture (short and longer term)?
  • How involved in the day-to-day execution do you want to be?
  • Where do you want to be in 1, 2, 5, 10 years?
  • What do you love doing? (What gives you energy?)
  • What do you not enjoy doing? (What drains you?)
  • What is your work to do in the company?
  • What does the company need from you now?

In Part 3 of our annual check-in for leaders, we’re shifting the question from, “How are things going for you as a leader?” to “What gaps exist in the leadership team?” Access Part 3 here.

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