November 17, 2021 12:04 AM EST

At the Charter Workplace Summit last week, we brought together researchers, executives—including the CEOs of Slack, LinkedIn, GoFundMe, and The New York Times—and others who are writing the playbook for how to lead in the new era of business. The question on the table: “What kind of leader do I need to be now?”

Below are some of our biggest takeaways from the summit about how to approach that central question. A leader for this moment is someone who can:

Know the line between enough certainty and too much.

  • One running theme: A leader shares what they’re sure of, and also doesn’t try to be sure of everything. As Slack CEO Stewart Butterfield put it: “Even if you don’t have all the answers, I think that the big obligation of leaders in this time is to give what certainty you can.” What are your organization’s priorities right now? What are the new norms and expectations?
  • GoFundMe CEO Tim Cadogan summed it up: “People want very clear purpose on what they’re working on, and then they want flexibility in how they go about that work.” An overreach on certainty can look a lot like dogmatism, but acknowledging its limits looks a lot like humility—and allows teams to stay nimble in the face of constant change.
  • Sarah Stein Greenberg, executive director of the Stanford d.school, argued that there’s value in sitting in ambiguity rather than rushing with confidence toward a solution. “When you stay in a problem for longer, you start to notice and understand things that are not obvious,” she said. Leaders who allow themselves to linger in that in-between space can find that they emerge with more creative, thoughtful ideas about how to move forward, as well as a new awareness of other problems that may otherwise have gone unnoticed.

Account for bias in designing new systems.

  • As Stanford economics professor Nicholas Bloom explained, there’s a danger in allowing too much freedom when it comes to workers designing their own hybrid schedules. Factors such as race, gender, family obligations, and disability status all play a role in who is willing or able to show up in person—and in Bloom’s research on presenteeism bias, employees who worked from home four days a week were half as likely to be promoted as those who were in the office full-time. “You basically, by accident, discriminate against certain subgroups,” Bloom said. “Some groups are coming five days a week, get promoted, move up, while others will be left behind.” If there’s such a thing as an ideal hybrid setup, it’s one that standardizes remote and in-office days across team members, so that no one loses out if they aren’t doing their work in the boss’s line of sight.
  • Trier Bryant and Kim Scott, the co-founders of Just Work, outlined a system for combating bias at the moment it takes place—and for creating a culture where calling out those moments isn’t only accepted, but welcomed. The first step: As a team, set a verbal signal for flagging out loud when someone displays an unconscious bias—at Just Work, they use “purple flag,” a less threatening but no less visible cousin of the red flag. The second step is to agree on a norm for what the person who’s been called out should do next, such as acknowledging or asking for more information. (Scott’s advice: “Say thank you, regardless of if you understand it or not, because it takes courage to call someone in on that bias.”) And the final step is making sure, as a group, to have at least one of these moments in every meeting. “If no bias gets flagged,” Bryant said, “usually what it means is that either people didn’t notice it and they need to learn to notice it, or people didn’t feel comfortable flagging the bias.”

Be transparent about their organization’s “why”…

  • Meredith Kopit Levien and Jacqueline M. Welch, CEO and CHRO of The New York Times, noted that the most straightforward way to ensure a company lives its values is to give employees a roadmap for doing so. To that end, the Times defined a set of behaviors for each of its six core values and how those behaviors apply to individual contributors, managers, and executives. “We define, for example, what does it mean to be curious? What does it mean to demonstrate respect?” Welch said. “Those definitions are now what will fuel every aspect of our employee life cycle,” from initial hiring interviews to promotions.
  • In a discussion about changing definitions of leadership, Asana COO Anne Raimondi and PayPal CHRO Kausik Rajgopal both stressed the importance of creating clarity around decision-making—communicating not only an organization’s path forward, but the reasoning that led it there. “The leader’s role is to define reality,” Raimondi said. “Give people context. Be transparent.” Or, as Rajgopal put it: “When a leader can be more transparent about the scaffolding of their logic for why they’re doing certain things or not doing certain things, it builds a deeper bond.” Especially in periods of change or instability, an understanding of how choices are being made can feel like an anchor.

…and help workers understand their own “why.”

  • LinkedIn CEO Ryan Roslansky shared a framework to help managers be true partners in helping employees achieve their goals. To start, ask each person to choose the two things that matter most to them in their career. Those two elements then get plotted onto a two-by-two chart, where the top right quadrant is the presence of both and the bottom left is the absence of both. The process of choosing just two is a clarifying exercise in itself, but beyond that, a shared visual provides a tactical approach to what might otherwise be an abstract conversation: “I walk into one-on-ones with my team, and I say, where are you on this two by two? And if you’re not in the top right quadrant, we at least have a framework to move it,” Roslansky explained. “So as a manager, you can help that person achieve what they’re trying to do in their career.”

Understand that the mental well-being of their employees and the success of their organization are inextricably linked.

  • As Just Works’ Bryant and Scott noted, there’s a continued mental cost to employees on the receiving end of bias and microaggressions. “Every second, every minute, that that person who was harmed is thinking about that, processing that, having to heal from that, is every minute and second they’re not doing their job,” Bryant said—an “invisible tax” that holds back marginalized workers, and therefore the entire team.
  • Just as cars need tune-ups and bodies need check-ups, companies, too, need regular maintenance. Dr. Angel Acosta, a healing educator and principal consultant at Acosta Consulting, described that maintenance as “slow work”—a deliberate process of shifting attention from daily and weekly demands to “the relational fabric of the company.” These pauses are both a preventive measure against and an antidote to employee burnout, an investment in individual and collective health that pays dividends in performance over the long term.

You can watch recordings from the Workplace Summit here. Additional videos will be available in the coming days.

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