Former Attorney General on Why Today’s Leaders Need to Be Introspective

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  • Recently, I sat down with Eric Holder, who served under President Obama as the 82nd Attorney General of the United States. In 2015, Holder returned to life in the private sector, where he provides legal counsel to companies and state legislatures. He and I discussed everything from mandatory sentencing to his relationship with President Obama, but what stood out to me most was his perspective on introspection. In our “always-on” culture, self-reflection is hard. Our attention spans are shorter, things move fast and we’re stretched thin between our responsibilities; I feel like I’m always on to the next thing. But in an age where our lives are fragmented, introspection is more important than ever. To find creative solutions to problems, we have to ask ourselves hard questions and reflect on what’s working and what isn’t. The same is true for companies.

    According to Holder, “Companies can always be introspective in the same way that we can be as individuals and ask tough questions of ourselves or as corporate entities. What are our strengths? What are our weaknesses? How can we do better?”

    Holder knows a thing or two about introspection. In his current role, companies tap him to ask difficult questions and help businesses improve everything from diversity to how they work with foreign governments. He’s valued for his ability to identify a company’s challenges and help the leadership team own up to underlying issues.

    Famously, Uber hired Holder to investigate reports of sexual harassment after engineer Susan Fowler published her blog post detailing “one very strange year” at the company. Holder’s report, which was a dozen pages long and detailed nine recommended changes at the company, serves as the basis for the cultural reboot that Uber is now executing.

    While Holder’s role is to take an unbiased look at a company’s challenges, he urges business leaders to do the same; it’s all too easy to blind oneself to glaring problems in the midst of financial success. On the other hand, leaders who are aware of their blind spots or vulnerabilities are more likely to anticipate challenges, admit mistakes (and learn from them) and course correct.

    I’m working on this too. Recently, Zillow Group's Rich Barton advised me to spend more time quietly reflecting on the business. The challenge is to manage the day-to-day but also take time to reflect. We’re all so busy, and thousands of things are thrown at us every day, so introspection takes self-discipline.

    Reflecting on aspects of our individual or company performance that need improvement can also be a little uncomfortable, but it helps us identify and solve problems faster. Plus, it’s easier to fix problems before they negatively impact company culture or morale, which is harder to shift.

    Holder’s commentary on introspection is timely in light of recent scandals. Consider Harvey Weinstein, whose behavior as the CEO of a powerful company went unchecked for decades. Today, we’ve seen an avalanche of accusations against him, but for years people looked the other way. With the democratization of information and the rise of social media, today’s leaders and companies can no longer hide behind a great PR team. All this transparency means we need to confront tough issues head on – and that requires the willingness to ask the difficult questions and be thoughtful, introspective and honest with our teams and ourselves. 

    Listen to our full conversation below, or read the transcript here.


  • Spencer Rascoff
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