What’s leadership, success, and work in 15 words?

What a former CEO of a listed company asked me.

The rain clouds had scurried off, leaving whimsical white strokes in the deepening blue. On top of those sat deposited cotton puffs. And in the distance, whipped cream ridges ringed an invisible 5-kilometre-radius cake.

Cycling along the Arakawa in Tokyo

As I was heading home from an evening ride along the riverside of East Tokyo, I got a message. It was from a former boss-mentor-friend. She’s so busy she only gets in touch when she needs something. She’s also about the only person I’d likely agree to any request from even if that means clearing my week or staying up all night.

She never had to make this face — Image courtesy of Giphy

I’m not the only one. She has people to call on from all industries and walks of life. She rarely has the time to tell us what she did with what we gave her, but none of us mind. She has this way of getting us to not only deliver, but over deliver. In my career, I’ve only worked full-time for her for 4 months. The other 6 years I’ve worked with her were all on a volunteer basis.

Here she was, asking me, what type of leader I was looking for. My answer would go into her keynote industry speech on millennials at a forum, together with 3 other people she had mentored. All of us have volunteered for her on multiple occasions. It makes you wonder — what type of leadership does it take to get paid professionals to take extra time out to help you, even when you can’t pay them? What value are you giving them?

What leadership qualities are needed to get people to willingly put in time and effort for you without pay?

A way to get succinct answers

Sometimes what it feels like, Jking — Image courtesy of Giphy

Since she needed to incorporate all of our answers, she got us to fill out a one-page sheet of questions. Her solution for getting quotable lines was to limit our our responses. The first set are more to help give context to our later answers about leadership, work, and success.

1. Name
2. Age
3. Education
4. Current job/employer
5. # of jobs since leaving school
6. # of FB friends
7. Do you play Pokemon Go?
8. Your definition of leadership (in 15 words of less)
9. What qualities do you look for in a leader that you respect? (in 15 words or less)
10. Your definition of work (in 15 words of less)
11. Your definition of success (in 15 words of less)
12. ONE proudest/exciting moment/event/achievement that you would like to share (in 50 words of less)

Do you play Pokemon Go?

Sourced from Giphy

No, I don’t. But she does, as a way to understand what young people these days care about.

Your definition of leadership

For most of my answers, I used her as a model. So many instances left such a deep impression: when she saved me from bumbling through meetings I was supposed to be running, when she picked up the phone to apologise to a potential sponsor about my mistake, and when she’d brief me before a meeting and make introductions that were effortless for me to pick up.

A leader is one who goes in before, behind, and beside the people they work with.

I’ve been lucky to have strong female role models who gave me responsibilities and coached me through delivering well on them. But it’s also easy to take good leadership for granted. The flip side is I often end up judging even decent leaders harshly as a result.

What qualities do you look for in a leader that you respect?

A leader in 14 words

I thought back to those moments she gently guided the discussion to the topic at hand and set an example of how to act with integrity and dignity. I thought about how she always offered effective, but generous descriptions of people who are sometimes difficult to work with. I recalled how she easily pulled up stories about her own mistakes and gave us permission to laugh at our shared human shortcomings. She highlighted the things I did for the company in team meetings, despite my many failures that she had to sit me down privately about. I remembered her looking at me and saying she was disappointed, that she had expected more. In every instance, I naturally wanted to do better.

A leader I respect is open with praise, measured with doubts, honest in private feedback, generous in public commentary.

Your definition of work

What does work mean to you?

My first response to the question about work was that I don’t think about “work”. I was tempted to write “work is a concept”, because the hardest work I’ve ever done, year on year, was for her and with her. The work I do isn’t always paid, but my work with her felt like it paid off because I was able to contribute and grow. Work can be what we like, but it doesn’t have to be. It would be nice if we’re paid, and many people need paid work, but we often put the most effort into things we choose to do.

Work is the effort and time we put into something.

Your definition of success

Success in 15 words

I look at others around me and often wonder why I haven’t done better. Then again, I know I haven’t done too poorly either getting jobs I love and being able to have work-life balance working three days a week. It’s not enough to dismiss “common” or “accepted” notions of success without defining something for ourselves. I am happy when I see others achieve what they wanted. At the same time, I don’t relate to the word success.

Success is accomplishing my goal or getting a result of equivalent or higher value to me.

Success can be as big and small as we want it to be. We should not belittle grand ambitions, nor look down on humble dreams. Both are of equal value and meaning to the people who hold them, and to the people they bring value to as a result of their dreams. I don’t feel much about it because I just want to keep moving forward.

ONE proudest/exciting moment/event/achievement that you would like to share

My real answer to the question

I gave her two options. The one above (genuine me) and the one I thought would be more proper. She took the one above, but I’ll share my mistaken assumption here too: “I walked the Shikoku 88-temple pilgrimage alone for 40 days during typhoon season and high summer. I slept on the street half the time. Despite spraining my ankle early on, I finished without treatment. Normally, a pilgrim makes one wish throughout, but I dedicated each temple to a specific person.”

I could not relate to the word ‘proudest’, so I substituted it for ‘most meaningful’. And I give her credit for giving me an unedited voice to share with her C-level audience.

I’d like to believe that these workplace values that I hold are not unique to my generation. While millennials may be more proactive, vocal, and even judgemental, about workplace culture, leadership, and values, the desire to contribute in a supportive environment, with visionary leadership, for something meaningful is an ideal no-one would be opposed to (even if they’re uninterested).

My mentor confessed to me during that phone call that she wanted to ask her colleagues, whom are mostly senior management and executives,

“If young people today are willing to spend so much extra time working on things outside of work they that they believe in, what does it say about the nature of the workplaces that we are creating now?

I want to ask of my generation — and of all people who are working:

if we so care about a company’s values, culture, and conduct, what are we doing as individuals to demonstrate that we embody the values we hold others to?

Even as we demand to be heard, how can we listen better to others? Even as we make our suggestions, how can we empathise and appreciate the perspectives of prior generations? How do we work with them instead of asking them to work more like us?

Over to you. Would love to hear your thoughts!

Originally published at thecupandtheroad.com on September 8, 2016.
The post is now only on Medium.
Updated July 6, 2017.