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Everybody wants a chief of staff, even when they don't know why

Tech Twitter has been abuzz over a Medium piece that questions whether the role actually works for Silicon Valley.

Leo McGarry

The West Wing's Leo McGarry (right) is the paradigm for so many chiefs of staff in tech. But that can be a problem.

Photo: Getty Images/Ron Jaffe/NBCU Photo Bank

Early in Amy Cheetham's career, she took a job as chief of staff to Zuora's head of North America and Asia Pacific sales. She spearheaded special projects, triaged priorities and became the executive's main sounding board. "It was really formative to my career," said Cheetham, who is now a VP at Costanoa Ventures, an early-stage VC firm. "I was truly on the same level as a fairly senior executive. It was so empowering."

But over the last day, Tech twitter has been abuzz over a Medium piece that questions whether the role actually works for Silicon Valley. Adam Kovacevich, the lead for Lime's North America & Asia Pacific government relations and public affairs team, argued in the piece that just because chiefs of staff work well in politics, that doesn't mean they can do the same for tech. He says that C-suite executives use them as crutches in weaker areas, make them glorified executive assistants and train the spotlight on the leader, not the company.

"As corporate chiefs of staff proliferate, they've become almost a status symbol for the ambitious executive — as potent a symbol of power as a corner office or an executive assistant," Kovacevich wrote.

The role first made waves a few years ago, when executives including Elon Musk, Peter Thiel and Mark Zuckerberg hired chiefs of staff, but it's now a fairly common practice at small startups, too. Kovacevich told me that he decided to write the piece because he was frustrated with the growing fad of tech executives, blinded by ambition, hiring a chief of staff without thinking through the role.

Many former chiefs of staff agreed with him. The role can be useful, they said, but not when the executives are looking for their own personal Leo McGarry or Leon Panetta.

"There are a lot of tech executives who are of the age and generation (I include myself in that) who grew up watching 'The West Wing.' Leo McGarry is still the archetype of what you think of as the chief of staff," said Dex Hunter-Torricke, former chief of staff to Brunswick Group's chairman and founder, Sir Alan Parker, and now the communications leader for the Facebook Oversight Board.

Mack McKelvey, a former chief of staff at Verisign and a big proponent of the job, believes the critics misunderstand the purpose of the role. The high-level player gets to quickly understand every aspect of a company and help fill important gaps, which she said helped launch her executive-level career. She cited Sheryl Sandberg, who served as chief of staff to then Secretary of the Treasury Lawrence Summers early in her career, as a key example of the power of the role.

But while it worked for McKelvey, there's often a big problem with the McGarry-style vision. "It's not a super-detailed blueprint on how to actually make that role work. So a lot of people think, 'Oh, I would love to have my own Leo,' but actually designing a role which gives space to somebody to actually deliver at that level, that's a totally different ballgame," Hunter-Torricke said.

Often, he added, the executives aren't willing to spend the time and hand over the power to create the chief of staff they think they envision. So, "they don't become an extra brain, they just become an extra pair of arms and legs, and that's when you end up with the most overpriced executive assistant ever. You have people who actually could be there to make leadership decisions, and instead they're picking up sandwiches."

In many companies, the chief of staff becomes a glorified appointment assistant, said Ana Milicevic, principal and co-founder of the management consulting company Sparrow Advisers. She worries that corporate chiefs of staff — especially women — will face questions down the line about whether their experiences were substantive enough.

Cheetham agreed this can be a problem for men and women alike. When she counsels other people considering the chief of staff role, she cautions against working for an executive who doesn't already have an executive assistant or similar administrative help. When she took the role at Zuora, she made it very clear that she would not do administrative work — and the job delivered, setting her on equal footing with the leader who hired her.

If leaders can give up on the political template for their chiefs of staff, there are ways to get around the fuzziness of the role. McKelvey has faith that startups could use the chief of staff role as a way to cultivate raw talent; many women, people of color and others from historically underrepresented groups in tech could use the role as a way to get onto the C-suite track.

In general, "I think it works. I think it's good that it exists. I think there's an asterisk after that," Cheetham said.

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