LIVE, LEARN, LEAD

After getting asked countless times about my leadership style in interviews, I decided to stop freestyling my answer and develop a personal framework that captures my POV on the most important qualities for leading people, either across large orgs or within small teams.

Leading comes pretty naturally to me, but I’ve gotten better at it thanks to a handful of really kickass people I’ve been lucky to work for and with. And yes, Virginia, there have been some bad apples, but thanks to them I also know what not to do :)

The result? The C.H.E.C.K.S. and Balance framework:

Specifically, Radical Candor. My friend and former colleague Kim Scott has helped transform how to give feedback with her best-selling book and framework that emphasizes being direct while caring personally as the key ingredients to delivering effective feedback. Fun fact: the “John Doe” obnoxious aggressive example of what not to do in chapter 2 was provided by yours truly :)

Humor, when used effectively, can cut tension and make you more accessible as a leader. My friend and mentor Dick Costolo is the GOAT when it comes to this, and my friends Jennifer Aaker and Naomi Bagdonas wrote an excellent book on why humor is so important. Fun(ny) fact: I helped them develop a course on this at Stanford.

Enabling people to break out of their comfort zones and take on bigger and bolder tasks (when they’re ready, of course) is the best way to prepare them for the next level. And if they fail, I don’t punish or let them beat themselves up. After all, mistakes are really just life lessons in disguise.

Companies are complex and go through myriad ups and downs over time. I’ve learned that providing context as quickly as you can about the current situation helps people better understand the “why” that led to the “what”. I also pull in examples from my past life to further frame what’s happening and confirm that sky isn’t actually falling.

I want to know that my contributions matter, so I find casual and creative ways to let individuals – and their colleagues – know when it’s a job well done. It’s important to do this throughout the year and not just in a performance review (also true for hard feedback). Peer-to-peer kudos programs are also really effective; they are a lot of fun and allow more visibility into who on the team is going above and beyond.

Life outside of work can significantly impact life at work, so I do my best to be a sounding board and offer support where I can. Remote work can make it harder to pick up on cues, hence it’s important to have regular check-ins and really try to create in-person moments. Also, the team mustn’t fear talking to me about their career ambitions, including news of an outside job offer they received. This is a positive thing, so I make the conversation all about how I can help them in making a decision.

AND… BALANCE

When I’m confident I’ve “checked the C.H.E.C.K.S.” I can feel a better sense of balance within the team. But the key is ensuring I’m consistently delivering candor, humor, empowerment, context, and support. If I’m balanced in my leadership, then it will inevitably trickle down.

This framework was influenced by my years coaching volleyball. Wins could create a false sense of invincibility, while losses could be perceived as the worst possible outcomes. The same is true in business – I’ve experienced the thrill of the rocketship and the agony of debilitating headwinds. But it’s important to keep the team balanced by focusing on the process and long-term goals – and leveraging both wins and losses as mechanisms for improvement.

Coaching also taught me a lot about stars and role players. To be successful, you need go-to players in critical moments, no doubt. But a team can’t solely rely on stars – everyone has a role in the team's success. If just one person carries too much weight, you’re imbalanced. Not to mention, if they exit the business (or simply take a vacation!) things can go sideways quickly. Balance is earned when there is a distribution of responsibilities, but more importantly when each individual understands them in the context of the broader team and company goals. In other words, all of the trees need to understand the forest they are building.