A Chief of Staff Could Have Saved Away and Steph Korey From Her Own Worst Behavior

If you clicked into this post, I'm guessing you already read The Verge's exposé of Steph Korey's toxic presence as the CEO at luggage company Away and her swift removal shortly after its publication. I encourage you to read the article firsthand, especially if you work in an environment where Slack is the primary method of communication. Few have come to Korey's defense, including her own company. I'm not here to defend her either; rather, I'm here to suggest how she could have saved herself (and her team) from her own worst behavior if she had a Chief of Staff by her side.

As recently as a few months ago, Away was recruiting for a Chief of Staff to support Steph - a search that began in the Spring of 2019 - perhaps at the urging of her board of directors. According to The Verge, the board simultaneously started to recruit a replacement CEO. Investor Directors are well known for using the Chief of Staff role to get more or better out of a CEO who is struggling in a hyper-growth environment. Interestingly, they were still recruiting for a Chief when I began job hunting in NYC in the fall.

It’s unclear whether Away ever hired a Chief of Staff for Steph. As of publication, there is only one person listed on LinkedIn with a Chief of Staff-like title (Senior Manager, Strategic Initiatives):

As of December 2019, only one employee at Away has a title similar to Chief of Staff

As of December 2019, only one employee at Away has a title similar to Chief of Staff

As a two-time Chief of Staff to the CEO, I can empathize with the day-to-day reality Steph faced over the last year. In no way do I condone how she chose to respond to this reality, but I understand how the never-ending stress and never-fast-enough pace would drive a person to her breaking point. She was at the helm of the buzziest direct-to-consumer company in a product space where brand equity and customer loyalty are the only competitive advantages.

After reading The Verge's article, relief that I wasn't Steph's Chief of Staff quickly turned into fascination. I couldn't stop thinking about all the ways an experienced Chief of Staff could have helped the Away team and, perhaps, saved Steph from her demise.

Five Ways a Chief of Staff could have helped Steph Korey at Away:

  1. Steph's Chief of Staff would have given her candid feedback, even when everyone else was terrified of her.

    CEOs rarely receive unbiased feedback from individuals inside the company. Sure, Boards and executive coaches give feedback, but rarely do they have access to the unvarnished day-in-and-day-out reality inside the walled garden. Steph's Chief of Staff would have been the only insider whose job it was to make sure that she was operating at 100%. With the right CEO/Chief of Staff relationship built on deep, mutual trust, the Chief of Staff can give impactful feedback that often otherwise goes unspoken.

  2. Steph's Chief of Staff would have buffered her raw emotions.

    Most CEO's bite their tongue and temper their emotions because they understand just how seriously every word is interpreted by the whole team. But CEOs are human and they need the opportunity to vent. Steph's Chief of Staff would have provided a safe space for her to vent, learned how to help her calm down, and formulated/implemented a more professional response to problems. Instead, Steph took to Slack and let the whole company experience her rageful stream of consciousness.

  3. Steph's Chief of Staff would have been her sounding board.

    Rather than responding to an operational issue by threatening to step in and manage logistics, Steph could have approached her Chief of Staff to have a "Am I insane or..." type of conversation. Her Chief of Staff could have offered a new perspective, dug around to get more information, and helped Steph to formulate an appropriate response. A CEO's job is to create leverage through coaching and direction, not to jump into the weeds and micromanage when problems arise.

  4. Steph's Chief of Staff would have amplified her vision using compassion, empathy, and accessibility, not intimidation.

    A Chief of Staff would have extended Steph's presence by spending meaningful time with the team to make sure they understood the vision. They would have invested time with the team to ensure that frazzled individuals understood their impact on the company's performance. Take for example the slower-than-ideal customer service response times: Steph was likely thinking about this issue as an ugly metric she would have to report in her board package, or as a potential social media nightmare that would catch her investors’ attention. Or even as an opening for her competition to step in and steal market share.

    Meanwhile, her team couldn't get past thinking about how overworked and underappreciated they were. A Chief of Staff can spend time with the team to amplify the CEO's message, to patiently answer questions, and to bring key points of confusion back to the CEO for clarification. Chiefs of Staff are great at establishing these invaluable feedback loops between the C-Suite and every level of the organization. Short feedback loops are critical in a hyper-growth environment, especially when the CEO is less than approachable.

  5. Steph's Chief of Staff would have facilitated difficult conversations at the executive level.

    Steph created a culture in which her customer service leaders successfully resorted to emotional manipulation to overwork and underpay her team. Surely the rest of the executive team didn't agree that this was the best approach. But who was facilitating difficult conversations across the entire executive team about this type of issue? Who was surfacing concerns, or offering a contrarian view? The Chief of Staff orchestrates these types of conversations because of their neutral role on the executive team. Their only agenda is the success of the company, not the success of their team's metrics. Steph could have used her Chief of Staff to lead difficult conversations at the executive level that would have likely been fraught with emotion.

Steph, I'm so sorry we didn't get to work together. I think I could have helped, or at least planted a few seeds with you about how detrimental your behavior was to the long-term health of the Away company culture. I wish the Away leadership team the best of luck as they navigate the team through this period of transformation.


Alicia DiamondChief of Staff