My Leadership Challenges

by Miki Kashtan

If anyone had told me some 30 years ago that at some point in the future I would be working with people much of my awake time and that I would be enjoying leading groups of people, I imagine it would have been hard for me to believe. I was working in computer programming and feeling really glad that I had machines to work with rather than people. The journey that took me from there to here has been nothing short of extraordinary and miraculous. 

Both photos: a recent workshop Miki (at right) led in Rochester, NY

I am particularly astonished that what I find most inspiring and surprising is that leadership is appealing to me, in large part, because I feel more able to be fully myself. It’s as if the position of leadership is giving me permission to be my full, powerful self. Through that experience, I also find the immense satisfaction of contributing to people’s lives, having a sense of meaning, a deep integrity about pursuing a calling, and the hope (or illusion?) that I can truly make a difference in the world on a larger scale than the individuals I work with.

Since I also work with and coach leaders, I am continually learning about leadership. Sometimes it’s through what the people I support tell me about their struggles and insights. Sometimes it’s through what other people tell me about their experiences with those same leaders. Seeing things from both ends has been so instructive in understanding why transforming the paradigm of leadership from the authority-based model to the collaborative model has been so elusive and challenging.

In addition to what I learn about leadership through working with other leaders, I also experience my own leadership as a learning lab. My ongoing research question continues to be understanding what it would take to succeed in establishing collaborative leadership practices and shifting out of the power-over paradigm. Much of the learning happens through encountering those unexpected moments in which a break occurs in the quality of trust and creative flow that I so cherish in general when I lead. This is what I want to write about today: some of those challenges which are still active and open. It’s part of my commitment to vulnerability, too: not to wait until I have it figured out and then write about it, and, instead, share the raw elemental discoveries and questions as they are when I am still grappling with them.