Leading with Empathy

My reflections on culture, management, and empowerment.

Zenan Liu
StashAway Product & Design
5 min readJun 13, 2018

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Image by Joshua Ness on Unsplash

“Culture eats strategy for lunch”

I’m a big fan of the “High Resolution” design leadership interview series. Unlike most other designer interviews that only focus on tools and craft, this series draws attention to many higher-level insights surrounding product design and design thinking — which is one the reasons that make it particularly interesting to me.

One of the biggest takeaways I get from the series is how much emphasis design leaders place on culture within their organisations. As I progress in my own career, it has become apparent to me that problems with processes and tools are at best irrelevant, and at worst harmful, when the underlying people problem is not solved. An essential component of the culture of a company or an organisation is the power structure. In one episode of the interview series, Cap Watkins puts it succinctly, the modern organisation should seek to abolish the traditional power structure that is inherent from the industrial revolution period where managers dictate, and instead focus on empowering employees to make important decisions on their own, while keeping the management informed.

Cap Watkins, VP of Design at Buzzfeed

To explain this idea better, Cap quoted in one of his blog posts the two different ways to approach management structures as outlined by Etsy’s CEO, Chad Dickerson:

Traditionally, most companies approach management with a top-down mindset, where the CEO sits at the top-most of the power structure and decisions are passed down through layers of managers to the bottom of the pyramid:

However, as Cap explains in his article, as managers, your job is no longer directly responsible for the work that gets done — that’s the responsibility of the makers. Instead, your output should be determined by the success of the people you manage. Therefore, a better way to view management is through an inverted organisational pyramid:

By inverting the structure pyramid, the role of the managers are no longer defined as dictating decisions and communicating priorities — it is treated instead as a supporting structure, not a power structure. Managers’ main responsibility is, therefore, to support their direct reports to make sure they have the necessary clarity and context to perform well in their jobs.

All companies have power structures. However, how we view our power structures is central to shaping innovativeness, happiness and success of our teams in an increasingly competitive market and diverse workforce. And at the heart of that supporting structure lies “empathy” — one of the most important qualities for leadership to foster empowerment in the modern organisations.

Empathy:

the action of understanding, being aware of, being sensitive to, and vicariously experiencing the feelings, thoughts, and experience of another of either the past or present without having the feelings, thoughts, and experience fully communicated in an objectively explicit manner — Merriam Webster

The dictionary definition of “empathy” explains that it is not enough to just understand the other person’s position and logic. Empathy extends beyond that. To be able to fully empathise, one has to become aware of and sensitive to how others feel and experience as well.

How should that be, then?

Empathy means being radically candid

One of the best management books I’ve read so far is Radical Candor by Kim Scott, in which she outlined a new philosophy and framework for management and leadership. To put simply, being radically candid means caring personally and challenging directly at the same time; and through that, leaders are able to create a positive culture of feedback and help people on the team achieve their fullest potential at work. It means bringing our full selves to work, instead of just our professional side, and putting the team’s interests ahead of ourselves.

Empathy means prioritising relationships

Relationships should always be prioritised in a collaborative team environment. In fact, they are the most important part of the job when in a leadership position. Prioritising relationships means supporting each other when the pressure is high, and celebrating progress together as a team. Direct, authentic relationships cultivate empathy, and help us get to know each other as a real human with real needs and wants — all necessary for fostering open communications within the team.

Empathy means being mindful of cultural differences

There are only two things I can’t stand in this world: people who are intolerant of other people’s culture — and the Dutch.

— Michael Caine as Nigel Powers in Goldmember (2002)

Working in an international team means that people come from a diverse collection of cultural backgrounds and preferences. Being mindful of cross-cultural communications demonstrates inclusiveness of the leadership, and has a long-lasting impact on improving engagement and positivity in the workplace. For example, in certain cultures, challenging authority may be perceived as rude or insubordinate while in other cultures it is encouraged and expected. Tailor your communications style to match the receiver’s cultural norm and preferences when giving and soliciting feedback is a great way to reinforce the message of inclusiveness and diversity within an international team.

Above all, empathy means giving a damn about people

It’s easy to focus only on the daily grind and hustle in a startup where everything is constantly changing all the time, and overlook the very people that make that initial mission possible in the first place. The best organisations and teams in the world prioritises people above everything else. Through that, they create positive environments for people to build great things together. They are the places where people feel confident, included, understood, and empowered to do the best work of their lives.

And that’s where I want to be.

We are constantly on the lookout for great talents to join our team. Visit our careers page to learn more and feel free to reach out to us!

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