We Need the Best of Each Other

Awakening

16th June 2015, Califonia Ave Caltrain Station

 

“At 14, I read A Brave New World and told myself that I wanted to be at the edge of the future, every day,” Mei Lin said, scribbling down a master framework that explained the why, how and what of her life and work. Having moved to Silicon Valley thirty something years ago after her university, the tiny Singaporean lady is known by her friends and colleagues as “a force of nature”. A long time colleague once said to her, “One day I’ll learn to say No to you. Not today”. Another joked, “Every time you turn away from Mei Lin and look back, she would have started another organization.”

We met two years ago during a Californian sunset outside of the Palo Alto train station. Our meeting came when I needed a spark amidst the wandering phase of my young adulthood. Twenty-two years old, first time living in Silicon Valley, first time having a “real” job in America, I was struggling to adapt. I didn’t quite understand what was going on with work or my team’s vibe, or feel like my skillset was well-utilized.

That evening, sitting in my tiny dorm room, I dove deep into the framework she had recommended. I experienced something no less than an awakening, a distinct burning sensation in my gut. “Oh my, there are people out there who are also trying to integrate all the fields I cared deeply about, from personal development to organizational learning and social change!” I exclaimed inside. Within the next few days, I devoured every talk I could find on YouTube and went to the bookstore to read more on what she recommended. That spark was so essential to me that it became what I most look in people I would be working with, especially the manager.

I was not alone in my experience. It is almost cliché to say that young people everywhere are yearning for work that matters to them, work that allows them to develop and even “make the world a better place.” We are bombarded with messages about what “work” should look like and mean to us. In 2000 it was “work-life balance,” 2010 “work-life integration,” and 2017 it is “work should feel like play.” That leaves young people really confused about what the world of work is. Schools don’t help either. Most universities have a career service center that help students craft the “perfect” resume, but none ventures to question what “work” means in the first place.

Previously, a bank clerk could see her 40-year labor as means to support the family. Now, within the first 10 years, a young professional can see how the meanings of her work evolve from daily bread winning to career stepping stones to a self-actualizing journey. As such, while the Gen X and Baby Boomers are worrying about machines taking away jobs, including theirs, Millennials face the much more existential question of what work is supposed to mean. For every high-achiever I know who goes to the best names in their fields, there is another who juggles multiple gigs, from waiting tables to tutoring kids to freelancing online. Different work, same confusion.

The youth is not alone. Never before has the capitalistic world witnessed such a large scale tension between the ideal of meaningful work and the reality of paying the bills. We are all together in this moment of profound disruption, with socio-economic, political and spiritual turmoil and “challenges looming ahead […] more serious and more daunting still than those posed by the social transformations of the twentieth century.” We struggle for a different way to work, to relate and to be together.

How do we then navigate in this time of change?

One way is to look for past wisdom. The other way is to work with and learn from people who are actively figuring it out. The latter was what I hoped for when I decided to work with Mei Lin the following summer. I was excited: she was someone whom I looked up to and whose vision I resonated with. What could go wrong, right?

Dreaming: a new way of seeing

May 2016, Mei Lin’s kitchen

The first two weeks were exciting and overwhelming. With a modest stipend from school, I lived in Mei Lin’s basement and worked from her beautiful kitchen, situated between a living room full of music instruments and a luxurious back garden. I was blown away by how many brilliant and dedicated people she could bring together there and I tried my best to follow along during these meetings. Afterwards I asked for all the materials I could read about this new organization, People Centered Internet. It was so new that there wasn’t much to read besides various Word documents, scattered somewhere in her computer.

Noticing my many questions, she said at first one-on-one “I have high expectation of you. Not only because of who you are, but also because this is what the work requires.”

That was perhaps the most motivating thing I’ve heard. I might not have needed an ego stroke, but I did need a clear standard on which I could judge my performance. I knew she also held herself to that standard, which inspired me to do better. As Drucker said, the executive who “sets standard that are not personal but grounded in the requirements of the task” and “demands for excellence” will too stimulate her colleagues to develop themselves.

She then asked: “K, you want to have a recommendation letter at the end of the summer, don’t you?” I timidly nodded, wondering what she was trying to get at with such a strange question.

“Then the question should be,” she continued, “how do you make it so that giving you a great recommendation is obviously the best thing for your boss to do?”

Something clicked in my mind. I must have stood in awe for a long five seconds. It was one of those golden moments that made the whole summer worthwhile.

Once I sat down and thought through Mei Lin’s question, I started appreciating the power of seeing from a different side. Consider the recommendation letter example: how could it be her best interest to write a good letter for me? Out of reciprocity, to exchange for the good job I’ve done? Or out of good will, to help a young person with potential? Or even bolder, out of her interest, to have her name associated with mine because I’m so good? Writing that last sentence made me cringe and taught me firsthand how hard it was to dream. The late inventor of the mouse Doug Engelbart whom Mei Lin was a protégé, once said, “Someone once called me ‘just a dreamer’. That offended me, the “just” part; being a real dreamer is hard work.”

Two subtle distinctions here. First, dreaming is not just wishful “positive thinking.” It is also downright practical. In my case, nobody wants to write a terrible referral, but everyone loves to talk about their favorite people. I had to trust that Mei Lin wanted the best for me, and I had to make it easy for her.

Second, it’s not only about trust. Indeed it is too easy to remain cynical and second-guess the intentions of others. Yet I have to remind myself often that this is also about taking responsibility so that others can make use of my work and I can make a meaningful contribution. In our increasingly collaborative world of work, the ability to see and think from another perspective as well as the desire and commitment to be helpful become the cornerstones. It is what Drucker said about management: “The task is to not to manage people, the task is to lead, and to make strength productive and weakness irrelevant.”

Fumbling and searching for an explanation

June 2016, Mei Lin’s Basement

As an intern, I first helped out with basic tasks like compiling conference attendee biographies and taking care of the ever growing spreadsheet of contacts. Soon the work picked up steam. Mei Lin was managing multiple projects on her own, each with several email threads that she would include me to follow-up on. She half-jokingly asked us to brace ourselves as we ventured into the frontier of the Digital Wild Wild West.

It was indeed an uncharted territory, for People-Centered Internet supported initiatives that would meaningfully connect the four billion previously unconnected. But what did that look like in day to day reality of the organization? It felt as if I was dropped into the middle of a new emerging ocean, where I had to learn to swim again before even knowing where the land was. I needed more clarity. I pushed for more context. To which Mei Lin responded, “I wish I could give you more, but right now it is not clear yet.” My hope for a sight of land was thus put on hold.

The journey of a lofty thousand miles starts with a single precarious step. On one occasion, Mei Lin wanted to review some software tools. I mistakenly thought she wanted me to think about what software the organization might need in the future, but thinking too far ahead proved to be unnecessary. The communication gap was so strange that she too was confused. “I don’t get it. Clearly you are very bright; how could you misunderstand such a simple instruction? You have to do the basic first before the extra,” she said during our quick check in at the kitchen one morning.

My tendency to overthink did not help either. I took the mantra of “putting oneself in the other person’s shoes” to the other extreme and tried too hard to understand what she wanted. All I ended up with was what I thought she wanted. I even resolved to confirm every word she said to the point of discussing who should end an email conversation. “I’d rather be awkward than stupid,” I told myself.

My heart would skip a beat whenever I sent in a piece of work — who know I would mess up again? Slowly, the ghastly fear of messing up the same way crept into my mind. Lo and behold, I did it again. This time was a bigger assignment where I overthought what is supposed to be a basic survey as a comprehensive design task.

I felt dumb. Worse, I felt as if I was a burden. She had been so generous to allow me incredible exposure to everything, give me work that mattered and even let me stay in her house. I was motivated to work hard and contribute, yet somehow I was just dragging her down. I didn’t even feel bad for myself; I felt bad for her having to deal with me…

What could explain this miscommunication? Was it just me? Awkward, inexperienced and perhaps, idiosyncratic? Or was it this generational gap?

After such frightening experiences, I was searching for another explanation. One evening as I was wandering in Mei Lin’s basement library, I stumbled across Peter Drucker again.

“The objectives set by subordinates for themselves are almost never what the superior thought they should be. […] the more capable they are, the more willing to take responsibility, the more will their perception of reality and of its objective opportunities and needs differ from the view of their superior or of the organization.”

I read these lines again, feeling a chill down my spine as it just pinpointed exactly my dilemma. That single passage helped me to stay open, to ask how others saw the situation and to explain my viewpoint. When these perceptions are shared, “any discrepancy between their conclusions and what their superior expected will stand out strongly. Who is right in such a difference is not as a rule important. For effective communication in meaningful terms has already been established.”, Drucker wrote.

Suddenly everything became clearer. The mental turmoil I experienced came from being exposed to the complexity of the situation, not just the incomprehensibility of another mind. Nobody was wrong, nobody “failed”. In fact, acknowledging that we see reality differently is the essence of effective collaboration. Without stumbling on Drucker that night, I would have left the internship with a sour taste, feeling like an absolute failure.

I felt more ready to talk to Mei Lin as the internship was about to end, not quite knowing how it would turn out.

The conversation

August 25th, afternoon, Redwood City train station

Mei Lin was driving me to the train station, sending me off after an eventful summer. I once heard that the car was better for challenging conversations. Rather than confronting each other face to face, both could look forward to where we were going together. Perhaps it was true. After several incidents of miscommunication and a subpar performance, I was afraid of this conversation. But I had to have it. One cannot learn without feedback.

I ventured by asking, “What did you learn this summer that surprised you?”

“It is really hard to work with young people,” Mei Lin replied without hesitation.

Ouch. I didn’t expect that exact answer. Tears swelled up in my eyes. I took a breath and continued, “Well, maybe not all young people. Maybe I’m just an odd case.”

“Maybe. Then you are not used to the level of precision that I’m used to,” Mei Lin said while looking ahead. That moment was tough, but somehow validating. It wasn’t just me who found working together so hard.

She continued, “One day when I was 35, my manager sat down with me and said: ‘Mei Lin, I know you worked hard. But you are not effective’. It was hard and yet very important for me to hear that truth. I wanted you to learn this when you are 23, not 35.”

In economic terms, I was a cost. I did not deliver much “value”. I was a bad hire. Indeed, Mei Lin wrote to me in a later email, “If you were not a summer intern I committed to take, I would have stopped paying you after the first one or two weeks and told you it wasn’t working out.” She knew I could take it, and I was indeed thankful for her gift of honest feedback. As Drucker said long ago, getting fired on the first job “is the least painful and the least damaging way to learn how to take a setback.”

In holistic terms, however, I’ve developed so much as an employee and as a person. I became more self-aware, competent and willing to contribute, none of which could neatly fall under “prosperity” nor be easily quantified in the Big Data bandwagon. As my story showed, until we expand our notion of prosperity, we will miss out these key intangible dimensions. As such, we risk becoming that proverbial manager who doesn’t know how to measure what she wants and settles for wanting what she can measure, as the late Russell Ackoff once quipped. I’d rather measure the right thing wrong than wrong thing right.

Epilogue

Our brain evolved through millions of years to allow us humans to perform amazing feats, from composing poetry to deriving rocket launching equations to creating a brain-scan machine to study itself. On the contrary, management is merely 150 years old. Management as an organ of society has not evolved enough as brain as an organ of the human body. It has a lot of catching up to do.

Most of the worries about robots taking away jobs focus on the wrong question. The question should be “How can the world be organized to accommodate increasing diversity and more complex interactions among its humans as well as non-humans? What social organ will need to be in place?” These are the questions all of us have to deal with in a world that is becoming increasingly small yet fragmented. Otherwise, we will risk knowing everything we can about every single part but little about how to put them together as wholes. It is not “Dreaming Big,” it is “Seeing Whole.” It is the often forgotten complement side of the analytical thinking so prevalent in the Western world since the Enlightenment. Indeed, Peter Drucker named one of his chapters “From Analysis to Perception” for this very reason and suggested rather tongue-in-cheek that “I see, therefore I am.” To see holistically is to ask “What do you wish to see in the world?” before “What do you want to do?”, a question many college student dread. In my experience, to ask the former question and genuinely listen is magic: our eyes light up and our hearts pour out the answer we have always known deep inside. Can we NOT thrive in a thriving community?

Paradoxically, as the boundaries between humans and machines are getting blurred, humans are realizing more how intertwined our lives are. One thing for near certainty: it will be a long time before we can automate the entangled nature of our relationships. Its very messiness is the fertile soil on which deeper trust can grow and bear the fruits of working together. Case in point: Mei Lin emailed me recently saying how she appreciated me more now than back then, and I knew our relationship would continue to prosper despite the bumpy start.

We are still at the very beginning of this age of possibility. As we venture into the frontier of the great Unknown, to strive together for the happy families, the flourishing communities and the inclusive societies that we yearn for, we will inevitably step on the rough edges of ourselves and of one another. As such, we need the best of each of us. We need, at our core, a more nuanced and humane management.

Its Job to Be Done is to create human synergy, and as Drucker would have said, an immense opportunity.