Lessons from the CEO’s office

• Hi, I’m Eva-Marie, and I recently wrapped up my 2 year Chief of Staff rotation at Springboard. At the 365 day mark, I put together a post on some specific advice for year one in the CoS role (see here).
• Since finishing up my rotation, I’ve wanted to put pen to paper on some of the more general learnings over my entire time as Chief of Staff. This article (part 1) is focused on leadership specifically. I’ll write more on talent, teams, systems, etc. in follow-up articles.

Two years as a Chief of Staff and what a ride! In hindsight, the experience was both professionally and personally transformative. It gave me access to startup realities that aren’t really known or experienced unless you’re a CEO yourself. The learnings were daily, however, some stand out more than others. Below I’ve captured four leadership lessons that have continued to make me ponder since my departure a couple of months ago. These are focused on CEO empathy, growing your capacity, energy management, and the power of goals.

4 Leadership Lessons I learned as Chief of Staff to a CEO

1. Being a CEO is hard; cut them some slack

Before starting the CoS role I had a naive idea of what being a CEO entailed. I had less empathy for CEOs when bad decisions were made or a company was underperforming. How hard could it be? And then my CoS stint de-glamorized all aspects of CEO life. I saw up close the never-ending weight of responsibility a CEO holds: of the team’s livelihood, the company’s future, of constant sound decision-making, and his or her own well-being.

And while CEO bashing may be easy to do when literally anything goes wrong, my perspective has completely changed in this regard. Being a CEO of an organization is one of the most difficult jobs in existence, and it’s unlikely any CEO, no matter how qualified, would get by without making any poor decisions.

It’s important to have empathy for leaders, in addition to other teammates. Not everything is black and white, and people farther from the CEO might not have all the context or gain witness to the emotion that went into a decision that seems unfair to others. Next time it seems obvious to you that your CEO/leader has made a bad decision or is underperforming, I’d encourage you to start with empathy before criticism. Maybe you don’t have all the context? Maybe there was another priority grabbing their attention? Maybe you would have done the same in their situation?

This isn’t to say let poor leaders off the hook. It’s more to create awareness that the habit of criticizing leaders is any easy one. The habit of empathizing first is a healthier one.

2. Embrace the stress to build resilience

The CoS role can be relentless. As the right-hand person to the CEO there seem to be endless high-priority tasks to get to. Unlike in other roles, I found there to be very few, if any, true “down weeks” to get through the email backlog or tackle a P2 project I hadn’t wrapped up. The marathon nature of being a CoS (or any leader) can feel intimidating at first. In the early days as CoS I’d feel late-night anxiety about upcoming important meetings, unfinished materials, or past conversations on a more constant basis.

But after a while everything becomes normal, right?

There is always an important meeting or deadline coming up, so you build the capacity to endure more high-stress situations on a frequent basis. This increased capacity is a gift. It grows relative to what you endure, and over time I had much less stress about routine CoS/CEO type tasks than I did in the first year. In my next role, I’m confident my capacity will be much greater, and I’ll be able to more easily take a step back from things that seem stressful and approach them with a smile.

3. Manage your energy, not your time

One of the most talked about CoS skills is time management. While everyone knows ruthless prioritization is key to any leadership role, I learned that focusing on energy management instead of time management was key to my sanity.

Some colleagues at Springboard recommended doing a weekly energy audit when things felt busier than usual. This involved taking stock of what I did in a week and then classifying each item as an energy adder (+) or detractor (-). By doing this simple but powerful exercise, it quickly became apparent what “sparked joy” for me at work and what didn’t. When I was working on process maintenance I found I had less time to do unexpected or additional tasks. In retrospect this was really because I found maintenance work more draining than building new things or achieving goals (which are big +++ for me!). So in reality, energy was the problem rather than time. The key lesson is to try to find a role that enables you to spend as much time as possible on things that give versus take your energy.

4. The best leadership tool: goals

Not gonna lie, I’m a nerd for goal-setting and accountability hacks. I set daily, weekly, and monthly goals using the Monk Manual, and love the feeling of consistently clarifying what matters to me and ticking off my achievements. A lot of my personal goal-setting habits came as a result of seeing the impact in a work context.

In my time as CoS, I saw the power of goal-setting & accountability at both the team and company level. Both are explained below.

At the CEO/company level, OKRs can be a great tool for leading the larger cross-functional team to focus on what matters. I built out an updated thoughtful Executive OKR system over the last year and the biggest learning for me was simple: clear cross-functional goal setting practices and accountability improve company performance. John Doerr’s Measure What Matters convinced me of their impact prior to implementation. If you don’t have a company-wide cross-functional top-down goal system in place, get on it.

At the team-level, I relied on goal-setting and accountability as a core leadership tool to drive team progress and build rapport, culture, and influence. Good goal hygiene was especially critical when I was handed ownership of a business function or team outside of my core expertise. For example, for a period of time I oversaw a part of our marketing & PR function without core marketing experience myself. My go-to methodology for establishing these practices with a new team include the following:

• Aligning on each individual’s objectives over a specific time horizon (e.g quarterly) and their unique role in each project using a responsibility matrix (see RASCI).
• Introducing systems for driving accountability e.g. a live dashboard or g-sheet that can be updated easily and frequently, and a weekly meeting for all to voiceover what they have done and plan to do.
• Rewarding good results In 1:1s, and sometimes group settings, and seeking to understand when goals were missed

This is a simplified overview of how I approach goal-setting and OKRs at the team and company. If people are interested in hearing more about this , let me know and I can write more about that specifically.

The CoS role is so unique in the access it gives you to leadership decision-making. It provides an opportunity to accelerate one’s career and thinking. I’ll continue to write some more learnings in the coming months. 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