A millennial’s notes on leadership, success, and work based on answers to a keynote industry speech on leadership. Each section is in direct response to a CEO’s question to 4 millennials that she has worked with in her 10+ years of serving and working with young people.

She sent a one-page sheet of questions to get quotes (mostly in 15 words or less). You can find my overview answers here.

I’ve been lucky to have strong female role models who gave me responsibilities and coached me through delivering well. I drew on these experiences to summarise my points, which are meant to capture the spirit — rather than the formula — for great leadership.

In this post, you’ll find the following sections:

  • Your definition of leadership.
  • What qualities do you look for in a leader you respect?
  • My context

Your definition of leadership (in 15 words of less)

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Leadership in 14 words

Good leaders “do what no-one else can do” because they choose to. Leadership is often in the trenches. Leadership is a choice, not a spotlight or a title. Leadership is manifest in those moments where one person is able to guide another in a way that comforts, motivates, and educates them. Guiding can include leading by example, providing an alternative perspective, and often charting a course that someone else is terrified to take.

With only 15 words, I wanted to encapsulate all the things I most remembered as great acts of leadership. The first memories that came to mind were with a particular boss:

  1. When I argued my heart out and was openly furious with the leadership’s decision. What allowed me to move forward 110% on something I wholeheartedly disagreed with was that my boss had my back and would take responsibility if it didn’t work. She was the first to take a risk that no-one else wanted to take the leap for because she wanted better. She didn’t just tell us we could do better or do pep talks. She took on the unenviable task of pissing us off and got us to over-deliver on our own expectations so we could be proud of ourselves.
  2. When I was lost and didn’t know how to tackle the problem. Almost always, the solutions involved 1 sheet of paper with a list, a diagram, or set of sticky notes. If it was an execution issue, she would do whatever was needed to release the bottleneck (such as calling in another team member, making a phone call, or giving a missing document). What she wouldn’t do is do my job for me: she would sit with me to check the result (which sometimes too longer than the first draft).
  3. When I’d messed up big time. The first person to firefight for me was my boss. If she needed to pick up the phone she would. In addition that, though, every mistake became a learning experience. I just learned on the spot what not to do for next time and also how to action a remedy instantly.

I didn’t rely on leadership as much when I was confident and successful (maybe a future post is needed about zealous pursuit in the wrong direction). I needed leadership when I was directionless or in trouble.

The running joke with my former boss is that people only go into her office when they have problems and disasters. It’s funny because it’s true. How many bosses are trusted to 1) listen to bad news, 2) brainstorm a solution, 3) and go all out to help you fix it?

Leadership is to be constantly where no-one wants to be. Dragging, nudging, pushing, cajoling, and taking the crazy first leap hoping your team will come after you are all on the possible activities. For the right boss, I would take that leap of faith, too. That leads to the next question: why are some people who do this more respected than others?

What qualities do you look for in a leader that you respect? (in 15 words or less)

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A leader in 14 words

We respect people for what they do, not what they say (unless it’s the act of speaking up or out). I could have rattled off a list of 15 qualities to answer this question, but values are meaningless without form.

A single action demonstrates a hundred virtues. Again, I recalled the moments where someone used their position of influence to demonstrate how to be a better person, a better team member. In leading by example, a leader inspires, encourages, and in some cases demands, their team to follow suit, which creates a great team culture and working environment.

Below are my elaborations on each phrase I used in my answer to the question.

Open with praise recalls the moments where a leader smoothly takes time to acknowledge the skills of others and to call attention to work done in the background that we may not have seen. Examples include acknowledging supportive spouses for understanding the recent overtime for a deadline, the skill required to execute a smooth production, the extra time someone spent to create the polished product. This acknowledgment is not to get on anyone’s good side. These words give credit where it is due and educate the team on appreciating the work of their colleagues, and better imagining the perspectives of others.

Measured with doubts gestures to giving people the benefit of the doubt and not undermining other people’s confidence in others. A project’s results will speak for themselves, so there is no need to create a negative self-fulfilling prophecy. If there is energy to doubt, then use it instead to find solutions from different angles. I am constantly in awe at how my mentor can work with the most challenging people (and have similar predictions as we do in terms of their delivery), but have solutions-based approach that at least keeps the delivered item within, or above, our expectations. Continue to deliver your part in a way that reflects your team’s potential for delivery.

Honest in private feedback means pointing out the talents, skills, and accomplishments that an individual may not notice for themselves as well as being constructive and nuanced in giving critical feedback. It is easy to blame someone else for being too touchy, but a great leader challenges themselves to communicate in a way where the message is well-received. Sometimes, it’s as simple as pointing out that someone has made the same promise multiple times with a neutral tone. Every mistake is an opportunity to learn, and it is up to a leader to set that tone when someone else is probably panicking. The point of feedback is to inspire an individual to improve and do better.

Generous in public commentary means not criticizing others behind their backs. The quality of people’s work and leadership will show. At the same time, one needs to point out gaps where relevant. Because a leader is an example to follow, voicing personal frustrations in a professional setting is damaging to a team’s confidence and a company image. A leader I respect is someone who shows the importance of letting go and focusing on the things that matter.

To me, all these acts as habits show integrity and build my trust in a leader.

My context

It’s easy to take good leadership for granted and judge mediocre leaders.

Every time someone demonstrates integrity and leadership, I take note. (Yes, it means I’m usually distracted in meetings because I’m usually analyzing people.) Every time an individual puts other people down, I file a note on what to not do. As someone who is fascinated with leadership, everything is an example to learn from and reminder on how to do better.

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 reassuring and visionary leadership, for something meaningful is an ideal no-one would be opposed to. Whether decades older or still in high school, I have encountered people who could not care less as well as those who strive every day to become better team members, workers, and leaders.

My closing thought on this not so much about the generation of millennials. My mentor had wanted to ask her colleagues, whom are all senior management and executives, if young people today are willing to spend so much extra time working with her on things 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 those with more experience? 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?

 

You can check out a summary post of all my answers on leadership, work, and success here.

8 comments

      1. Aside from the obvious answers (my bosses, family etc.), my favorite leaders are friends I have to lead lives filled with purpose and who do things that inspire me. I “look up” to these leaders more than the usual lot because we see eye to eye, and as they lead me in many ways I am setting my own example as well.

        Liked by 1 person

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