365 days as a Chief of Staff

Hi there! I’m Eva-Marie, and I just reached my one year CoS anniversary. On reaching this milestone, I wanted to reflect on some of my quick-win learnings. I hope that other Chiefs starting out on their journeys (or other non-Chief readers embarking on a new role) can pick up one nugget of info from my learnings. If so I will see this as a success.

Over the last few years, the Chief of Staff role has been trending, especially in the tech world. From my perspective part of the appeal is linked with the mystery of the role. Every time I hit enter on a Chief of Staff related search on Google it kindly responds with a number of articles related to ‘What does a Chief of Staff do?’ The world is confused, and so was I until I dove into my first 90 days. This reflection will talk about things that made my early CoS days easier and not the responsibilities themselves; for that info feel free to hit up Google.

CoS first baby steps

To help set the scene, April 1, 2020 was my first official day as CoS at Springboard, a ~250 person future of work startup focused on bridging the skills gap through affordable human first online education. This was exactly 2 weeks after the world had gone into lockdown and needless to say, being thrown into a crisis management role during an ongoing global crisis was challenging. Although COVID shaped my first 90 days in a pretty significant way, I’ll share my generalized quick-win learnings so that they are applicable in the future.

— Show up consistently:

Nothing beats being highly responsive and reliable in your first 90 days. If you’re new to working directly with your principal, building trust is the most important thing to spend your time on. Acting in a consistent and reliable way in your actions, comms, and follow-through will ramp you up quickly.

What does this look like? This can be responding ASAP to a question your principal has on Slack, sending an End of Week review email to share what you spent your time on, or simply asking before / after a meeting ‘how can I support you?’. This is not rocket science but doing it in a consistent way can have a compounding effect.

— Influence by asking questions:

I love asking questions to understand things. In the CoS role I found this was one of the best (and easiest) tools in my toolkit for building context, relationships, and understanding. Oftentimes you’re expected to figure out an ambiguous situation or interpersonal dynamic and leading with questions has never failed me. In most meetings I strive to find a balance of roughly listening 70% of the time, asking questions 20% of the time, and sharing my thoughts 10% of the time. Asking questions is not only a powerful learning tool, but also a way more useful tactic in guiding people toward the answer or decision rather than sharing my thoughts. I think this approach is especially important in a role where you’re often one of the people in the room with the least experience in the area. Through active listening, CoS influence comes from connecting the dots between stakeholders’ goals and concerns, rather than being the expert on any particular subject.

— Classify and clarify:

Looking back, I see my first 90 days as a classification exercise. Every time a task propped up for the CEO we’d determine if this was something that fell into the CoS wheelhouse or something better off owned by the CEO or Exec EA. In a role where everything could fall under your responsibility it’s important to continuously ask your principal this. Looking back I didn’t do this enough (more on that later) and ended up taking on more than I could handle — maybe my classification algorithm had a bug? ;) Regardless, the advice of classifying and clarifying your ownership still stands. I recommend doing it live and often in a 1:1 convo with a task list that can be prioritized and weighted.

— Remember, it’s not about you:

The CoS role is that of an enabler. It requires a low level of self-orientation and ego. You exist in your role to serve your principal’s needs and not your own, which is unlike most other jobs. You don’t own your priorities and constantly need to adapt to someone else’s needs. Having a way to remind yourself of your purpose was helpful for me, e.g a post-it with the tagline your job is to meet the CEO’s needs! You’ll face (many) internal dilemmas about the endless things you could do for the org or other executives and you’ll need ways to remind yourself of your core purpose to serve your principal.

Growing into the role — early adolescence

After my first 3–6 months I entered what I am calling a period of ‘ early adolescence’ which came with its own unique insights.

— No man is an island, except if you’re a CoS:

During my ‘growth’ phase I realized how lonely the role was. I sit on the Exec team, but am not an Exec; I attend meetings but oftentimes don’t contribute; I have a confusing title so people don’t know what to approach me about. The role is, at its core, isolating. What also exemplified this isolation was that I’m CoS at a company that I had been with for 2+ years prior to transitioning to the role, so I had friendships in the org but the dynamics had changed.

Given that you’re privy to sensitive information and being discrete is crucial, it’s hard to connect with other teammates in the same way once you’re appointed CoS. I often would meet with teammates and listen to their issues but not be able to validate or invalidate their concerns. This was no doubt frustrating for people I had a relationship with. After a few months of awkwardly not doing this well, I started to share with people directly that given my role I’m not able to share my frank thoughts with them but I can promise to listen intently. Setting this expectation was important and I am still working on doing this well in personal settings.

Apart from expectation setting, I also found two things helpful in alleviating the feeling of isolation:

• (1) Formally creating an Office of the CEO team (CEO + EA + COS) to have a core group outside the Exec team
• (2) Connecting with other Chiefs to build collegiality and community. I joined the CoS Network and the On Deck COS fellowship at about the 8–10 month mark in the role. These communities have given me an opportunity to confidentially share my honest thoughts without risk.

— Getting comfortable with living in the learning zone:

Considering the role can be so broad there is always learning to be done. I was initially drawn to the role as I saw it as a startup CEO bootcamp: a unique opportunity to get full visibility into all the mechanics that make a company run. I’m someone who learns best by doing so it was hard for me to transition into a new osmosis style of learning (and especially in this role it’s unlikely you’ll have a teacher or get hand-holding).

To help augment the inevitable osmosis style learning I read books, interviewed experts, took online courses, and listened to podcasts. To be tactical, some examples of how this played out are below:

• When we were fundraising I read Venture Deals by Brad Feld and Jason Mendelson to understand how the lawyer and I could best collaborate to get things across the line
• When given the task to refine our company strategy & planning cycle I interviewed 10+ operators to understand how they do it
• To build out my finance knowledge I took a Training the Street course, and am currently reading Corporate Finance for dummies :)
• To build an Exec offsite program I reached out to a few Exec coaches to hear best practices
• And when all else failed I would rely on Google to find me the answer

This is something I still struggle with, as historically having ownership of something rapidly increases my speed of learning. In the role you rarely own things but most often support / augment things so I’m always curious to hear how other Chiefs excel at mastery while also doing their day job.

— When the going gets tough, speak up:

One of my biggest lessons to-date is pretty cliche but as the supporter it’s especially important to ask for support when you need it. Nearing the 10 month mark I entered a particularly tough period where it felt like I had an endless list of things that were important and urgent and complicated. After burning myself into the ground for a few weeks, I crashed and saw the light — I wasn’t asking for help enough! The role is demanding and apparently the 1 year mark is notorious for reaching peak CoS burnout, so none of this should be a surprise but it still crept up on me.

To get myself through the piling workload, I went back to what was initially effective and that was classifying and weighting my tasks. Early on the classification exercise had been based on types of work, e.g internal comms, external rels, special projects, being the CEO proxy, etc., but I learned that this wasn’t the best way of describing the work in a way where I could understand what was giving me energy or taking it away.

To better assign my work based on energy add versus detraction we changed the framework to classify areas of work as ‘running the biz’, ‘changing the biz’, or ‘plugging gaps’. I realized ‘changing the biz’ type work gave me the most energy but I had been spending most of my time ‘running the biz’ in the months leading up to my burning out. To help reframe this the CEO and I met to methodically walk through all the things I owned and challenged if I should be the owner and what type of work this is. We re-prioritized, re-assigned and re-organized my work, and although this work is never done, having a new framework helped me reset the role and my feelings towards it.

The last year has been an incredible year of growth, learning, and intensity (let’s not forget the pandemic!). I’m so grateful to Gautam Tambay for giving me the opportunity to be his first Chief of Staff and to learn (and laugh) my way into the role. I can’t wait to see what the CoS late teenage years and early adulthood brings.

If you have questions on the CoS role or anything else, feel free to connect on LinkedIn or reach me at evamariecos[at]gmail.com