How to be a great Chief of Staff in tech

I spent almost seven years at Google as the Chief of Staff to Jerry Dischler, the product VP of the Search Ads team (and a few other teams by the end of my tenure), so new Chiefs of Staff at Google were often directed my way to learn from my experience. As the Chief of Staff role is proliferating around the tech world, I wanted to capture my talking points so that I could easily share them with others interested in this kind of role.

So what does a chief of staff do? Most people are familiar with the chief of staff role in politics through seeing them portrayed in TV shows e.g. Leo McGarry on the West Wing. In those shows, the chief of staff is the right-hand-man of the president, serving as their sounding board, and then organizing staff to execute on the president’s agenda. The chief of staff role for tech executives functions in a similar role, but the specifics of the role may be vastly different from exec to exec.

Success for a chief of staff lies in making their executive and their team more effective. That’s why the role can vary so much – each exec and team will have a different set of support needs to make them most effective, and the chief of staff’s job is to figure out what those needs are, and make sure they are filled. This made it a great fit for me, as a self-styled Unrepentant Generalist who finds meaning in helping people be more effective. I loved the fact that my responsibilities changed from year to year as my exec grew his skills and his org.

So when people asked me what my typical day was like as a chief of staff, I never knew how to answer; in a given week, I could be putting together slides for a leadership review, analyzing what was going on with revenue, coordinating with the sales team on quarterly goals, and thinking about the long-term future of advertising in an on-demand world. That variety was what kept me in the same job for almost seven years…because the job kept changing.

As the job was codified into a “Product Operations” job ladder within Google over the last few years, they classified the job responsibilities into the buckets of Strategy, Operations, Communications and Leadership. The way I like to describe it is in terms of the annual planning cycle:

  • Strategy: In the fall, my VP and I were responsible for figuring out the plan for the team for the next year. We would come up with questions to elicit a multi-year vision for the team, and deliver framing materials such as metrics decks to drive that discussion. I drove much of this process each year, especially in framing the challenges that the team was facing in upcoming years. This would conclude with a leadership offsite to discuss and agree upon the upcoming year’s strategy.
  • Communications: Once we agreed on a strategy, we had to communicate it, starting with sharing it the broader team so that everybody reporting into my VP understood the context of our strategy (Start with Why) and how their specific work fit into it. We also had to share what we planned to do with leaders across Google in sales, finance, and other product areas. Communication would continue throughout the year as we delivered progress and updates on the strategy in forums such as leadership summits, team all-hands meetings, finance updates, etc. My role would be to come up with the talking points, and build out the slides in coordination with our internal comms person. I would also be the person to answer questions from our operational teams such as finance and sales when they had questions about priorities and why we were making certain choices.
  • Operations: Once we had a strategy and communicated it, we had to execute on the strategy. This is the nitty-gritty of setting and tracking OKRs, managing headcount and budget, monitoring key metrics and raising flags when things are going off track, and generally making sure the team is running smoothly. This is where most of my time was spent throughout the year.
  • Leadership: This can take many forms, but the way I thought about this was that my job was not to be my VP’s flunky and unthinkingly do what he said, but to be his thought partner and to challenge him and his team with my perspective. I was there to help provide direction and thought leadership across my VP’s org; my joking description was that he couldn’t always fully trust his team with questions about priorities, because his ambitious directors would each say their own product was the most important one that needed more resources. My job was to be the dispassionate observer with no skin in the game except to make the org and Google successful.

One other set of responsibilities that would fall into the Strategy or Leadership areas of the Product Operations ladder is what I call the “Somebody” jobs. These arose when my VP would be talking to his SVP or his team and say “Somebody should look into X and figure out what’s going on and how we should respond”. They’d look around, and all the directors had defined responsibilities with too much to do, and then they’d look at me, and say “Eric, can you look into X?” These were effectively management consulting engagements, where my job was to go survey the landscape, bring back some recommendations, and let them make a decision knowing that I had collected the relevant information. I always enjoyed these jobs as they often involved thinking about big topics like the future of offline advertising, or the role of advertising agencies as advertising shifts online, and they provided a nice change of pace to the on-going operations work.

As noted earlier, the time spent on each of these responsibilities will vary widely depending on the exec being supported. Some execs are great at operations, and need help with the strategy and communications parts. Others are great at articulating an inspiring vision for the future, but need help turning that vision into reality via operations. Others might have those wired, but need a lot of “Somebody” jobs to develop a strategy in the context of the broader industry and plans from across Google. Still others may need you to work with their admin to manage their calendar because they don’t know how to say no. So to make your exec more effective requires understanding their strengths and weaknesses, and how you can enhance the strengths while making sure the weak areas get done either by you or by help that you arrange.

So what makes a chief of staff successful? A few things come to mind:

  • The humility to realize it’s not about you. A chief of staff role will have great visibility, but the job is not to increase your own standing, but to make your exec and his team more effective. This can be frustrating at performance review time in that it is impossible to measure your contribution directly; I believe I made my VP more effective and successful, but perhaps he was just awesome and I wasn’t contributing anything to his success. Without the ability to run a counterfactual experiment, there’s no way to tell the difference. So to be successful in this job requires finding meaning in the work itself, as any accolades will rightly go to the exec and his team as they are the ones actually doing the work and executing.
  • Another aspect that requires humility is being willing to do whatever is necessary to make the team successful. Somebody that comes in thinking “oh, X or Y is beneath me” is going to have a hard time being successful; when I interviewed people for my team, I was looking for a history of figuring out what needed to happen, rolling up their sleeves and making it happen. How will you show value in your first 90 days on the job? What will you make easier for the team? In my case, I took over all interactions with finance – when finance reached out to a product manager, the PMs would immediately cc me to respond so that they didn’t have to go back and forth with finance.
  • A broad skillset and a willingness to learn what you don’t know. If something needs to get done, and nobody knows how to do it, it’s time to be the “somebody” that will figure it out and get it done. Every year, I was confronted with situations where I had no idea what to do, and I took my best shot, drawing on my broad skillset and my powerful network to help me navigate the complexity.
  • A strong personal relationship with your exec. Since your job as a Chief of Staff is to make them successful, you have to like your exec and want them to succeed. Another part of your job will be to serve as their proxy and know how they think, and that requires spending lots of time with them to get inside their head. If you don’t feel the sort of chemistry that makes you want to spend lots of time with your exec, it’s going to be challenging to be successful.
  • A skill of your own. One risk of being a Chief of Staff is that you will be seen as nothing more than the mouthpiece of the exec. One way to counter that risk is to have your own skillset that adds value. Engineering teams respect expertise, so having expertise in a relevant area will earn you credibility in a way that no amount of operations will. In my case, I had spent four years doing revenue forecasting and business modeling before taking the Chief of Staff job, so I came in with a skillset that was highly relevant to ads teams, and that gave me instant credibility.

To give credit where it’s due, these last two points (strong personal relationship, and having a skill of your own) were shared with me by Matt Waddell, who was the first Chief of Staff at Google, and offered me those tips when I was starting my job as Chief of Staff.

Being a Chief of Staff is a remarkable job – you have an opportunity to shape the future of the team, think about the big picture, and learn about every aspect of the business. You have incredibly high leverage in that you have the ear of your exec, and you run the operations that translate vision into execution. One personal example is from the strategy planning process in 2014, when I plotted out the growth trends over the next few years if our team didn’t make changes to the product, and suggested a few interventions the team could try. In 2018, I plotted out what actually happened vs. what I had forecast four years earlier, and there was a huge difference because the team had made significant product changes. It’s not clear how much credit I deserve for that change in trajectory – would it have happened anyway if somebody else looked at the data? Would the team have decided to make those changes on their own? But I share this example because I feel it speaks to the value of being the person who can step back and think about where the business is going, and provide that perspective to the team to perhaps change how they think about their individual projects.

So that’s the overview of everything I know about being a great Chief of Staff for a tech exec. If you have been or have worked with a Chief of Staff, what am I missing? If you are aspiring to this kind of role, what are you taking away from this post?

One thought on “How to be a great Chief of Staff in tech

  1. When I posted this to LinkedIn, I added a tl;dr summary of how to be successful as a Chief of Staff: having the humility to realize it’s not about you, and looking for ways you can be of service and add value to your exec and your org.

    Here’s a secret: the tl;dr advice applies to every job, not just to being a Chief of Staff.

Leave a Reply

Your email address will not be published.