What makes a good Leader?

What Makes a Good Leader?

What I’ve learned over my career in People Operations

Last month, I was fortunate enough to join Medium as its new Head of People, responsible for among other things recruiting, HR, learning, and diversity. I’d been a fan of the company for a number of years, although I’d only recently become a subscriber — and I had yet to publish an article. I believe in “dog-fooding” my company’s products and enjoy writing, so it seemed like it would be worthwhile and good fun to publish something on Medium’s platform. But for a while I was stuck scratching my head on what subject matter to tackle.

It dawned on me that I had an obvious topic that came up during my first week at Medium. Medium hosts a company All Hands every two weeks called FAM, short for Friday Afternoon Meeting. It’s a lot of fun, as Medians are a jolly and creative group. Besides presentations and an open Q&A, new hires also step up on Zoom to introduce themselves and answer questions such as, “what were you doing before Medium?” and, “tell us something about yourself that isn’t obvious”. Absent the ability to meet in person, these virtual events have become the primary way for Medians to get to know one another and stay abreast of company developments. Because I was joining as Head of People, I was given an extra question, “what makes a good leader?”, which initially made me blanch.

What makes a good leader? That’s a big question if there ever was one. After overcoming my trepidation, I reflected on what I’d observed and learned over the years and gave it my best go at FAM. Here’s a more detailed version of my answer.

People have been thinking and writing about the “leadership question” for a long time. I’ll take as a given some of the fundamentals of being a good leader. Leaders are expected to set a direction, gain followership from their team, and organize their efforts in order to get to a desired end goal. Leaders ought to have the right basic moral character, because being effective and popular while pursuing corrupt means and destructive ends does not make a leader “good”. I’ll focus today on three mindsets and behaviors that I believe distinguish the best leaders from the rest of the pack.

1. Good leaders understand the power of context and are highly attuned to it

In matters of style, swim with the current; in matters of principle, stand like a rock. — Thomas Jefferson

Context matters a lot when it comes to leadership. You could put the same leader in two different situations and the recipe for success could be radically different.

An officer leading soldiers into combat needs to maintain a rigid chain of command. In most cases they can’t afford to give their troops freedom to deviate from plan or experiment with contradictory approaches. Survival and the imperatives of field combat require a clear team hierarchy and top down decision making. A soldier who refuses an order can be court-martialed because insubordination threatens the success of the mission and the lives of their fellow soldiers. Similarly if you walk onto a commercial passenger aircraft, you’re compelled by law to follow the directions of the captain and crew for the safety of everyone on board.

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On the other hand, the leader of a team of software engineers developing a consumer or enterprise product (say, Tik Tok, Medium or Slack) would lose the trust and respect of the engineers if they expected them to follow top down orders without question. The best software teams are built to be creative, flexible and nimble. They learn, experiment, launch and iterate in quick development cycles. Major breakthroughs have originated from curious, talented engineers exploring their personal interests. As an ex-Googler, examples like Gmail, Maps and AdSense (responsible for a quarter of Google’s revenues) come to mind. It helps that most software endeavors are not matters of life and death. Mistakes and dead ends are not disasters but valuable learning opportunities, as long as you don’t repeat mistakes or annoy your users too much in the process.

Context is always a driving factor in leadership. In a consumer software company, you can afford to give employees much greater freedom to act, while the same approach would lead to disaster in a highly regulated company distributing alcohol, tobacco or pharmaceuticals. Sometimes a leader needs to push their team harder because they are falling behind and capable of more. In other times they need to recognize the team is burned out, take the foot off the accelerator and focus instead on encouraging self-care or rebuilding frayed team relationships. Someone languishing on a team with a poor manager or bad team dynamics could be a surprise star on another team — I’ve seen this happen repeatedly. Good leaders are attuned to context and act according to the situation, rather than adhere to a rigid formula.

2. Good leaders care about their people and build diverse and inclusive teams

The first responsibility of a leader is to define reality. The last is to say thank you. In between, the leader is a servant. — Max DePree

In order to build trust, loyalty and followership, it’s important for leaders to show genuine care and concern for their team. This principle is grounded in the dynamic of social reciprocity. A leader who expects their people to put forward their best efforts will naturally be expected by their team members to show concern for their individual interests. Why would they go above and beyond if their leader isn’t willing to do the same for them?

Leaders should demonstrate care by taking an interest in the professional growth and development of their people. Good leaders take the time to understand each person’s passions and goals. They listen, ask the right questions, and help their people to form a realistic plan to reach these goals. They follow up by giving opportunities for practice, feedback and coaching. This sounds straightforward, but success requires intentionality, skill and time investment.

By extension, good leaders care about the personal well being of their team members. When a team member is sick, burned out or in distress, it’s almost impossible for them to perform. This is especially true in a world riven by Covid-19, which has increased global stress and social isolation. Remote work has thrust the workplace into the homes of many workers. Personal factors have always impacted the workplace environment, but the pandemic has made their effects more pronounced. Good leaders understand this. They get to know their team members on a personal level, reading explicit and implicit cues, and act accordingly.

The best leaders are committed to building diverse and inclusive teams. The evidence is overwhelming that diverse teams are simply more effective and performant¹. Including all voices regardless of background or seniority not only increases the likelihood of success, but also promotes inclusion and psychological safety, which is a basic foundation for strong teams². It takes more time and effort for a leader to build a diverse team, and to manage occasional friction from having different frames of reference represented. Wise leaders know this investment is extremely worthwhile and hold themselves personally accountable on diversity and inclusion.

3. Good leaders balance confidence with humility

A leader is best when people barely know they exist, when their work is done, their aim fulfilled, the people will say: we did it ourselves. — Lao Tzu

Leaders need to have confidence in the direction they are setting, or at least trust in the (hopefully, sound) decision making process that got them to a solution. For a great read on high stakes decision making, see President Obama’s December 9, 2020 Medium article, “How I Approach the Toughest Decisions”. In tough, ambiguous situations, it’s important for a leader to own decisions and rally their team — even if the end goal appears unattainable at times. If a leader doesn’t have basic confidence or optimism, it’s difficult for the team to keep the faith. I’ll share a personal example with lower stakes, but that was still important to my team.

Between 2011 and 2015, I led Google’s university recruiting efforts in the Americas for tech teams. We hired BS/MSc/PhD graduates for roles such as software engineering, site reliability and product design. Google was struggling to find enough industry engineers to meet its growth, so the university team was challenged to expand hiring as much as possible while increasing diversity. This seemed like tall order since Google had a high technical bar and was already hiring close to a thousand interns and graduates a year. How were we going to “10x” a system that was already one of the biggest and most selective employers of university talent?

One advantage we had was a creative, talented and dedicated university team, as well as a budget to invest. We ran a number of ambitious initiatives, including publishing Google learning curricula and developing online courses to democratize student access. We greatly expanded the number of schools we reached out to and launched programs like Google in Residence with Historically Black Colleges and Universities (HBCU’s), and Tech Residency which provided graduates with a year’s apprenticeship before placing them in full time tech roles. We hit and tried to fix bottlenecks such as scarce interviewer availability among our engineers. We even rented out apartment blocks in the SF South Bay in anticipation of having to house more interns. We had no idea if our efforts were going to work and if we would actually fill our open positions or housing. It would be many months before we would know for sure.

Naturally there were many moments when the team and I had doubts about our probability of success. People worried about what it would mean for their performance reviews and careers if they fell short. Despite my own concerns I encouraged everyone to stay optimistic, think big, execute well and learn from our mistakes. I tried to create psychological safety by not assigning blame for experiments that didn’t work out³, and by pointing out our company culture was to set impossible goals. It was ok if we didn’t get all the way there. The important thing was to do our best and get much better. In the end, our efforts paid off. We increased hiring by over 50% a year for several years running and increased diverse representation — still lower than our “moonshot” targets, but well ahead of historical performance.

I’ve made the case that leaders need to be confident, yet a leader who sells a dream without any grounding in reality is obviously doing a disservice. The world is a complicated and nuanced place. At Google X, teams are asked to imagine failure in order to understand what risks to mitigate. It’s a great practice that I’d recommend. Yet it’s impossible for even the best leaders and teams to see around every corner, or anticipate every contingency. When I was at Juul Labs, the trajectory of the company was thrown off course, and its very existence threatened when the unintended consequences of teenage use emerged (I’ll save that for another story!). Good leaders have a humility that comes from knowing that big challenges are inherently hard. Instead of being overly arrogant or deferential, they seek a middle path of openness and constructive engagement.

I’ll leave you with a quote from our friends at Glose, a Paris-based social e-book app and store that was acquired by Medium this month. Among their company values are notions of “ambition” and “humility”, and they express this point perfectly:

Our ambition is not fueled by ego, but by urgency, and a clear conscience of the fact that most problems of tomorrow will be solved by education today.

We stay humble not in spite of our ambition but because of it. We know we are far from our goal, and we know we won’t get there alone, but by gathering great talent and generating love from our users.

Generally speaking, we believe humility is natural in the face of any ambitious endeavor and should be core to any team work. We leave our ego at the door in the morning, and bring coffee instead.

¹ Some good starting points are McKinsey’s “Delivering through Diversity” paper (January 2018), Gompers & Kovvali, “The Other Diversity Dividend” (HBR July-August 2018), Eswaran, “The Business Case For Diversity in the Workplace is now Overwhelming”(World Economic Forum April 2019).

² Check out “What Google learned from its Quest to Build the Perfect Team” (New York Times Magazine February 25, 2016)

³For example, some housing blocks filled with giddy Google interns became a neighborhood problem and public relations issue. This was something we should have foreseen.


What makes a good Leader? was originally published in Noteworthy – The Journal Blog on Medium, where people are continuing the conversation by highlighting and responding to this story.

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