Part 4: Chief of Staff — The First 90 Days

Maggie Hsu

April 7, 2020

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The first 90 days are critical to establishing the right frameworks and relationships that will set up a Corporate Chief of Staff for long-term success. I interviewed 12 Chiefs of Staff to learn how they approached their new roles. While these Chiefs all came from different backgrounds, worked at companies of vastly different sizes, and had different expectations for their CoS role, they all followed some common tactical best practices.

Much of the corporate CoS role is about indirect influence, as the main working relationships for a CoS are typically not his direct reports. For a CoS, success in the role requires not only working well with one’s executive, but also having credibility across the senior leadership team (SLT) and with other employees.

This article is structured against two key goals and associated actions for achieving those goals. These goals are:

  1. To establish trust and gain alignment with your executive
  2. To establish trust and gain alignment with employees, both on the senior leadership team and elsewhere in the company

This article does not address what the CoS will do, but rather how the CoS should work.

Goal 1: To establish trust and gain alignment with your executive

Since the CoS role requires directly acting on behalf of your executive, there must be a high level of trust and alignment in both directions.

JohnMark Ludwick, a facilitator of the McChrystal Group’s 2019 Chief of Staff Summit, noted that a CoS must establish authenticated trust with one’s executive — essentially, layers of trust necessary for an executive to feel comfortable opening up when it matters most.

Action: Invest significant time with your executive upfront
All the CoS’s agreed that you need to spend a disproportionate amount of time with your executive at the beginning of your tenure. This includes not just sitting in on as many meetings as possible, but also participating where appropriate, whether in the meeting or by taking next actions from the meeting. This is a prime opportunity to learn what your executive’s time is spent on, their communication style, and the dynamics of their key relationships.

The way in which this is executed will look very different based on a number of factors — such as whether you are in a new or established CoS role, whether you are an internal or external hire, the company size and stage, the company’s geographic scope, what industry the company is in, and how the company is organized. When Nika Shclover joined Token as CoS, she spent the first few weeks shadowing all meetings, both internal and external, just learning the business. The CoS role was specifically created for her, so this was an opportunity to identify areas where she might be able to contribute. On the other hand, Ben Winokur, CoS to the CEO at Passport, was at Passport for over 2 years in other roles before transitioning to the CoS role. While the CoS role was new, Ben had already established trust with the executive team, so they were comfortable working with Ben as a thought partner and strategic advisor right off the bat.

Action: Explicitly discuss your goals
Since the CoS role is not a standard role, it helps to have an early, explicit conversation about your professional development goals. You should also understand what your executive is looking to accomplish by having a CoS.

Richard McLean, CoS to the CTO at Elsevier, wrote a “user manual” for himself that he shared with his executive. The idea was not to explain what he does at work, but how he works. One of Richard’s values was to deliver outcomes and be judged on results, not activities. This value resonated with his executive, who himself wanted to be held accountable and who asked for open, candid feedback from Richard in turn. These user manuals are valuable not just to share with your executive but also with other colleagues. Richard has compiled several of these manuals here.

Carmen Collyns, CoS at Brex, joined as the 70th person at the company, helping them scale to 400 people across 4 offices just one year later. She supports Brex’s Co-Founders in a generalist capacity. When Carmen started, she made sure to ask them a series of questions upfront, including: “Where do you want to take this company?” and “What skills are you actively trying to improve?” This kept her focused and allowed her to clearly map her activities against these answers. [The full list of Carmen’s questions is at the end of this article]

Action: Learn each other’s working styles
This is absolutely critical to having a successful working relationship. At McKinsey, we held a “team learning” at the beginning of every project to understand each team member’s working styles. Rather than assume others would know our communication preferences and quirks, we would simply tell everyone else what they were. They could be anything from “I prefer e-mail over voicemail” or “please cc me on all correspondence related to this workstream” to “on Tuesday evenings I am offline due to a family commitment”.

With your executive, this should also include a two-way conversation on how you both prefer to give and receive feedback. Should feedback be given real-time or weekly? Is it given in front of others or one-on-one? Many of the CoS’s had to routinely ask their executives for feedback; it wasn’t something that was regularly offered.

Leland Chamlin, CoS at Bowery Farming, shared that one of his interviews with CEO Irving Fain involved them getting into a 45-minute debate about something not related to Bowery Farming at all — the topic of what drives long term success in the music industry. One of the reasons Irving hired Leland was because Leland wasn’t afraid to provide feedback and push back.

If you do write a user manual, this can all be included there for discussion, and can also evolve as needed. Molly McCarthy, CoS at Insight Partners, suggested regularly monitoring your working style alignment.

Action: Set a communication cadence
For the first two weeks, you should ideally sync with your executive twice a day — once at the beginning of the day and once at the end of the day. This may seem excessive but is critical to quickly aligning your priorities.

After that, you should establish a cadence of three types of meetings: daily check-ins, project review, and strategic brainstorming.

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Holding regular alignment meetings with your executive are necessary in order to succeed in the CoS role

Your executive should be prioritizing these meetings, as they ultimately save time. If your daily check-ins are regularly cancelled then you should have a candid conversation to address the issue.

Tom Oliphant, CoS to Karen Peacock, COO at Intercom, has two 1:1’s with Karen each week. One is shorter to discuss more tactical items, and the second is longer to discuss broader strategic and long-term items. Carmen Collyns, CoS at Brex, found a slightly different rhythm with her Co-Founder. They also have two 1:1’s each week, but both utilize the same format where she can bundle and synthesize many updates, suggest next steps, and get approval. For higher priority items, they find the time wherever possible to communicate on these.

When I was CoS to Tony Hsieh, we learned that he was constantly getting one-off inbound requests from a variety of places. It cost him time to qualify each request — that is, understand what exactly someone was requesting, what resources they already had, etc. Tony realized he wanted to have the requests qualified and bundled so he could respond by type. Once we figured that out, I was able to aggregate and standardize the requests for him to review. He could then quickly go through each request and provide feedback.

Goal 2: To establish trust and gain alignment with employees, both on the senior leadership team (SLT) and elsewhere in the company

Since so much of the CoS’s role relies on informal influence, you need to have relationships with the SLT as well as with colleagues across the company.

Action: Explicitly communicate and demonstrate the purpose of the role
Since the role is still relatively new and can have many different iterations, you and your executive need to clearly communicate and demonstrate the purpose of the role to the SLT. Here are a few archetypes:

Enabler: Alice Lan, CoS at Opencare, came into the role when Opencare had grown rapidly from 25 to 50 employees within 6 months. Opencare hadn’t previously had a CoS Role, so her executive, Co-Founder Nik Bratkovski, had to set a clear understanding of the role for the broader organization. The leadership team initially saw Alice as a gatekeeper. She realized she needed to build personal relationships with them and demonstrate that instead, she functioned as an enabler. For example, Alice could help get high priority decisions in front of Nik, accelerating decision-making time from a week to a day. In order to do this, she created an “assertions document”, which walked through the key decision points for leaders and helped structure their thoughts. [Alice’s full assertion table is at the end of this article]

Counselor: Tom Oliphant, CoS to Karen Peacock at Intercom, was set up for success by Karen. Karen picked key influencers within the company to interview Tom for the role, so it was pre-socialized even before he began. After joining, he counseled business unit leaders behind-the-scenes to help them reach the best decisions.

Insulator: George Boyar, CoS at Mentor Collective, was able to insulate other functional heads from being disrupted. As new projects came up, he could take them on, leaving the functional leads able to focus on existing operations. If George ended up working on a project for more than a month, it was a signal that the work might merit an additional full time hire.

Connector: Given the CoS’s cross-functional view of the organization, it’s natural for the CoS to be able to look across teams and identify tactical ways in which people can be working together. Molly McCarthy, CoS at Insight Partners, was able to connect the right people at the right time, calling her job one of “mixing and matching”.

Problem Solver: Many CoS’s described being a catch-all for the leadership team. They were the first stop for new initiatives where it wasn’t clear where the responsibility would eventually sit. Ranika Kejriwal was the CoS to the Chief Product Officer at Tinder. She summarized her job as “problem solving — finding the root cause of an issue and figuring out a solution”.

Aligner: Charlie Joyce, CoS at OnDeck, shared an example of aligning meetings so subject matter experts could contribute their expertise in new ways. Often the expert was so entrenched in their area of focus that they didn’t realize their perspective might help another team.

Action: Rotate through multiple teams
It’s important to get early exposure to all parts of the business. Rachel Lau was previously CoS at Via. She joined the company in December 2016 and immediately did a series of one-week rotations through their teams, including operations, data science, and customer service. In addition to giving Rachel a cross-functional understanding of the company, it also helped her build authentic connections. When new projects came up requiring cross-functional collaboration, such as real estate expansion, Rachel was able to effectively lead them due to her existing relationships across the company.

Finally, as a CoS, you must also establish trust and gain alignment with external parties, board members, and other stakeholders. Many of the tactical action items discussed in this article also apply to those stakeholders.

Thank you to the following Chiefs from the Chief of Staff Tech Network for taking the time to provide their insight for this article:

Alice Lan (Engagement Manager at Opencare)
Ben Winokur (CoS to the CEO at Passport)
Billie Solomon (CoS at Spin)
Carmen Collyns (VP People Strategy at Brex)
Charlie Joyce (Manager Strategic Initiatives at OnDeck)
George Boyar (CoS at Mentor Collective)
Leland Chamlin (CoS at Bowery Farming)
Molly McCarthy (VP and CoS at Insight Partners)
Nika Shclover (Co-Founder at Knight Bus, former CoS at Token)
Rachel Lau (Treasury Go To Market Strategy at Paypal, former CoS at Via)
Ranika Kejriwal (former CoS to the Head of Product at Tinder)
Richard McLean (Director of Strategy & Performance at Elsevier)
Tom Oliphant (CoS at Intercom)

Additional Resources

Questions from Carmen Collyns, CoS at Brex

  • Where do you want to take this company?
  • What are your values (personal and company)?
  • Do you want to work on all things together, or delegate certain things for me to run with? Will I be a complement to you, or an extension of you?
  • What are you bad at? What skills are you actively trying to improve
  • What does a great day for you look like, and how could I help you achieve that?
  • Do you have an Executive Assistant? (Answer must be yes as the CoS is not serving an EA role)

Assertion Table from Alice Lan, CoS at Opencare

Priority level: High/Medium/Low (remove all low priority from CEO scope)
Leader: Person who needs CEO input
Time, Budget, Effort: Bullet points on time, budget and resources (remove anything under $X from CEO scope)
Pros: 1–3 bullet points on why this recommendation
Risks: 1–3 bullet points on any risks with this recommendation
Mitigations: 1–3 bullet points on mitigation plan for risks
Relevant Links: Pre-read/financial model if relevant
Action Needed: Input/Feedback/Brainstorm/Sign-off/Follow-up meeting

Join two robust Chief of Staff communities: the Chief of Staff Tech Network and the Corporate Chiefs of Staff Network

Read The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter (recommended by multiple Chiefs)

Read Paul Cohen’s 4-part series on the Chief of Staff role, including what to do in the first 6 months (recommended by Billie Solomon, CoS at Spin)

Next: Part 5: Chief of Staff Best Practices

Read All 5 Parts:
Part 1: The Role of a Corporate Chief of Staff
Part 2: How to Become a Chief of Staff
Part 3: How to Find and Hire a Chief of Staff
Part 4: Chief of Staff — The First 90 Days
[this article]
Part 5: Chief of Staff Best Practices