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Leading with Values, Instinct, and Intuition

Round Editorial

"Data will often tell the truth that we want to hear." Stacy Brown-Philpot, former CEO TaskRabbit, shares when to look at the data, when to listen to your instincts, and how to lead with your values. Data is essential to drive business decisions. Hard numbers are an important input for leaders when making decisions with far-reaching implications across revenue, growth, and teams. But there are other important, sometimes overlooked, components of leadership: values, instinct, and intuition.

Former CEO of TaskRabbit, Stacy Brown-Philpot, emphasizes the value of caring about a company’s people as much as shareholder interest. Brown-Philpot spoke with Round’s Chief Impact Officer, Rachel Williams, about how to lead with humanity and why following your instincts builds stronger companies. Here are five takeaways from the conversation:

1. Caring for your people has ripple effects

Caring about the people in your organization is not only a compassionate thing to do – it has a direct impact on building a brand and driving profits. Care deeply is the number one core value of TaskRabbit, a people-powered business. As CEO, Stacy Brown-Philpot lived this value by prioritizing customers, Taskers, and employees. “If you are hiring somebody to come into your home who you’ve never met before, you're certainly going to want somebody to come in who's going to care deeply about what it is that they're doing for you and you're going to want to build that sense of trust.” Business leaders who create environments in which people are supported create a foundation of trust, and that leads to a highly valued brand. When companies prioritize people they are more likely to drive organic growth through word-of-mouth praise. Creating a culture where people have a positive experience and want to share that experience can lead to a competitive advantage - reducing marketing costs and improves lifetime value.

2. Instincts are as important as data for decision-making.

It often seems that the best path to a decision is trusting data; however, relying on your instincts can lead you in a different, often better, direction. Deciding when to use one over the other isn’t easy, but gets better with practice. There is a tendency to believe the data tells the whole story; when in reality, it often reinforces the story we want to hear. As a result, many business leaders are trained to think with their heads instead of their hearts. In reality, instincts are as important in decision making. We all have instincts that may not align with the data. Exploring this gut sense, and actively probing your intuition, can often reveal an alternative path. Stacy went with her gut instinct and helped the organization make the right choice during the pandemic. Staying open enabled the TaskRabbit team to adapt, helping not only the Taskers, but also the community they served.

3. Adaptive leadership is the foundation of authentic leadership

Although it can be easier to stick to what you've tried before when leading a company, ingrained habits and approaches aren’t always best. Instead, it’s important to be willing to adapt to different circumstances and situations to lead effectively and authentically. Adaptation can manifest in different ways. One example is tuning into the nuances of an unfamiliar culture to understand why a group of people makes particular decisions or prioritizes certain values. A significant part of adapting is building relationships. Getting to know people can guide how to adjust one’s default leadership style to be more effective and authentic. When Stacy started leading Google India, she learned that her “Silicon Valley approach” didn’t work. Adapting as a leader allowed Stacy to learn that leadership evolves. Her advice to others? “Get centered in your core […] the how you do it will be reflected in you showing up in what matters to you.”

4. Show up as your authentic self

It can be difficult to be authentic as a leader, when leaders are often expected to act and behave a certain way. But it’s important to push through fear of judgment for both oneself and their team. For Stacy, wearing her natural hair at Google felt unnerving – she spoke with her husband, and eventually decided to take the leap. If you're facing a situation like this as a leader, it's nearly guaranteed that your team is facing similar situations. Living out your values and being your authentic self gives other people permission, and encouragement, to do the same.5. Look beneath the surface to understand what's driving decision-making. People have their own set of circumstances and experiences that inform their decision-making. Seeking to understand what someone is going through personally can help reveal why they’re making certain decisions – and often help navigate conflict. For example, if a team member hasn’t shown up for a critical meeting. Their absence can be frustrating, may feel personal, and results in tension. Instead of deciding why your colleague made the decision not to show up, make the effort to ask. What’s going on in their life that affected their behavior or drove them in a certain direction? Did something happen recently that made them feel excluded? Are they overworked? There’s always something underneath someone’s decision – and helping find a resolution to the conflict will fix the fractured relationship.

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