Reflections on Asking “How am I Doing?”

May 14, 2025

Leaving the safe zone of “what am I doing?”.


“Its hard to ask a question if you’re scared of the answer.”

Henry Mallet, Spirited, season 2 episode 5.


The question.

For many of us, whether it is with our teams, our boards, a review process such as a 360, or alone with our thoughts, the hardest question with the potential for the scariest answer, is “how am I doing?.

In my first coaching program, a little over 30 years ago, asking clients for feedback wasn’t on the curriculum. Feedback came from the mentors and trainers and it was for the most part on what we did, such as using the prescribed prompts, staying in our coaching lane, and providing appropriate encouragement and resources.

All good, but not particularly directed towards, and perhaps was even a distraction from, our self-awareness or self-actualization as coaches as it wasn’t linked to the how (nod to Simon Sinek) we showed up in our practice.

Once I began asking “how am I doing?”, both from others and of myself, everything changed. I sought out coaching and facilitation teachers and mentors who focused on the importance of ethics, on creating meaningful work with clients, and on continued personal and professional insights and growth. This approach transformed my understanding of why and how I do my work and challenged and strengthened what I do.


A little bit on the “what am I doing?”.

As much as what we do is important (skilled and competent are good things!), the big critical question for leaders isn’t “what am I doing?”. Any organization worth its salt has sound accountability and transparency policies and practices that reveal if we are successfully:

  • implementing the strategic plan or not
  • building partnerships or not
  • managing the finances or not
  • meeting organizational productivity goals or not
  • setting expectations, assigning work, and managing results or not
  • hitting key strokes, pressing send, and showing up at meetings or not

More on the “how am I doing?”.

The big critical question for leaders is “how am I doing?”. I have two takes on the question.

  1. “How” as in, how I take care of my well-being.

Leadership is work. It may be joyful, satisfying, invigorating, tiring, risky, or any of the other many things that we can feel on any given day, but it is always work.

For us to do the work that we are here to do, we need to take care of our well-being. That means taking care of our whole-self needs from sleep and nutrition through to self-awareness, self-management, and finding or creating meaning in life.

So, how are you doing?

  1. “How” as in, how I do my work.

I’m in the camp of no matter what you get done in your work day, if you have an ends justifies whatever the means attitude, you are not a courageous leader.

How we ethically show up with kindness, compassion, humility, curiosity, creativity, and all the other good stuff that you and I are here for, is what makes for a better team, organization, and world. I’ve summed this up into what I call the 6 Cs of Courageous Leadership (clever eh?):

  1. a commitment to the work of the organization
  2. excellent communication skills
  3. taking care with work and with people
  4. leading a healthy and wise culture
  5. building meaningful connections with others
  6. effectively engaging with challenges

So, how are you doing?


Reflecting on how you are doing.

As always, reflect your way and with kindness and compassion. You might want to find some time to sit with the question “how am I doing?”, to let it sink in to all the nooks and crannies where, to build on the words of my favourite fictional punk ghost Henry Mallet, we hide the answers that scare us.

The answers you might be scared of are not necessarily about so-called “gaps” or “weaknesses” (by so-called I mean hooey). The answers may be about what you do well, the amazing skills and strengths you have for navigating leadership in this wild world, and the beauty and potential you may find in the nooks and crannies for taking your leadership practice to the next level. Yeah, that can be the scary stuff.

I’m here for you,

Babs


Photo by Matt Walsh on Unsplash

Why work with me as your coach?

Because life and work is a demanding journey that requires attention and care.

I’ll help you expand and hone your self awareness and awareness of others, your expertise, and your wise and ethical behaviours while celebrating your resilience and courage for what is before you.

You can find out more about my coaching and leadership development services at courageousleaders.ca.

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