LED: Can you describe your journey and how you’ve ended up as Chief of Staff?

 

Luke: My path is definitely not typical - I kind of wandered into this. I wanted to work at a place where Tech was applied to make the products better. Over the years, I ended up working in Big Tech in various roles - I’ve worked as a Developer, as a UX Manager, and as a Program Manager.

 

At some point in my career though, I felt that I wanted to be exposed to the big picture, and not just work on a small portion of a bigger thing. I wanted to have visibility into how the whole system works, end to end. This is typically not that easy in functional roles such as program management. For eg: I worked on a team responsible for adding templates to Google Docs - this is obviously an important feature, but it’s still a feature of a bigger thing. It didn’t help me see the full picture of what makes Google Docs successful.

 

Now, you could get this at a startup, where the product and team are much smaller, and you can get that visibility more easily. But my preference was to work in a big company. I’m not gonna be CEO of Google of course :) But I think as Chief of Staff, you can be paired with a VP or a senior Exec, and really see how the whole company works to contribute to its larger mission. Google’s speech technology is cutting edge and used by millions of people every single day, and I get visibility into the whole thing end to end. Speech tech at Google provides automatic captions for YouTube, speaks driving directions to keep drivers safe, powers the Google Assistant, and provides speech to countless 3rd party apps using our Cloud APIs. That is exciting stuff for me. I wake up early thanks to caffeine and this exciting, rewarding job.

 

For me, being a Chief of Staff was a choice to depart from solving a specific feature to working on the entire team and system. .

 

LED: What does a Chief of Staff do?

 

Luke: This role can have various flavors. I’m in a big tech Chief of Staff role. There are government ones, healthcare ones etc which are potentially different. I’m familiar with a typical Chief of Staff role in big tech companies.

 

A Chief of Staff is a seat at the table at the Executive level. You are the left hand to the right hand of your executive. It’s almost like a blood type match. You can’t just become Chief of Staff to any and every VP. If say a VP is very technically oriented and deep in his area (as an example), then that’s a great place for me - because I can complement them with my communication skills, organizational excellence skills, and ability to monitor and improve team health.

 

This is similar to my current role. I manage the cadence of all hands, staff meetings, exec reviews. I manage the budget. I have to answer questions such as how and where do you allocate headcount? What strategic areas get resources? Budget and Resources are fairly typical responsibilities for a CoS. Coming to team health - managing employee surveys, thinking through any reorgs for the team with leads, conducting roundtables to bubble up ideas from across the org. And for many of these, I sit in and make decisions - and this is because I’m complementing my VP here, I do this.

 

There are other VPs who are really into this organizational details etc, and therefore might need a Chief of Staff who will lean into tech details too. At Google, most VPs are technical though so what I’m doing is a typical Chief of Staff role.

 

LED: Can you share an example of a project you’ve worked on as Chief of Staff?

 

Luke: One thing that happened some time back, is that my team grew really fast. Team size is a common thing that the Chief of Staff has to manage. When the team grows really fast, it’s important to make sure there’s a vision, a strategy and that everyone is on the same page about it. It also helps to make sure we don’t have overlapping efforts. When you have hundreds of ppl, you don’t know what everyone is working on. Eg: A small team of 3-4 people might be doing something that another team might be working on elsewhere. To avoid this, I set up an engineering review process to discuss highlights of work happening across the team, inviting everyone, and making sure there was efficient communication across the board. And this helps keep the entire team running very efficiently plus stay in the know about what’s happening. My VP is most effective when he has this extra perspective across our team, and I love that it’s my job to make that happen!

 

LED: How would you suggest someone evaluate whether they’d enjoy this role or not?

 

Luke: Do you like being very independent in your ability to execute? You’re given tasks in single sentences - they can take an hour or a quarter. You can choose where to invest your time. I have a lot of autonomy viz where to focus my time. And personally I really like this. Typically, this happens when you pair really well with your exec.

 

LED: What’s the typical background needed for this role?

 

Luke: I don’t fit the typical background, but a lot of folks have MBAs from an Ivy League school, who then immediately step into a Chief of Staff role. And I’ve seen long time company people (eg: 20 yrs), become Chiefs of Staff and help new VPs be successful. I think I’m somewhere in the middle - I fit more of the company person profile since I’ve worked at Google for a while. When I got my first Chief of Staff role, I’d been there for a little over 4 years and I had a skillset that a VP could use.

 

LED: What do you think are the major skills needed for this job?

 

Luke: Here are the skills that I would call out:

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• Program management and Organization skills - these are pretty much baseline

• You need a solid understand of the relevant technology and the business

• You need good relationship skills. If you already have relationships in the organization, even better.

• Ability to do servant leadership and some management - my current team that directly reports to me is small, but I have to as such lead a much larger organization without direct authority

• Attention to detail is key. A C-level leader has attention to their focus area. You have to pay attention to the rest - make sure you’re filling in these gaps.

 

LED: When evaluating Chief of Staff roles - are there characteristics that differentiate a “great” Chief of Staff role, vs just an “average” Chief of Staff role?

 

Luke: A great role is really about how well your skills pair with your exec’s skills. The pairing part is a huge part of this role. How well do you complement and match?

 

Another thing to understand is that if you want to learn from someone - this role is not from you. You need to see any gaps for yourself, and figure out where to add value yourself. Your VP will not know these by design. The way to illustrate is - When you’re joining a line function such as marketing or finance - your manager needs to be responsible for success.

 

Most importantly, once your manager is a VP - they are not responsible for your success. You have to be successful in spite of them. If they have a shortcoming, your job is to manage around that and address them in your own way. And that’s the value that you’re bringing as their Chief of Staff. It’s almost like magic. Your VP needs to think - “Wow, I’m so magically good at all these things now!” It is not a helpful strategy to convince your VP to become better at something. They’re already successful. If they are unorganized, or not interested in logistics - you don’t complain. Instead, you think - “How can I make this interesting for my VP?” Your job is to close the gap on their shortcomings.

 

If you feel you’ll be able to do the above in a role, you should jump on that opportunity.

 

LED: What questions should a candidate ask when evaluating a Chief of Staff role?

 

Luke: I have a few recommendations:

 

• Ask your Exec about where do they currently spend their time. Just a simple, high level, percentage wise on various tasks. And follow up with what part of that do they enjoy and right after that, how well do they think the org is doing in each of those areas. For eg: Say they spend 20% on operations but they hate it. Then you know that that’s an area you’ll likely want to spend time on as Chief of Staff.

• See if the old chief of staff is still there. This can be a blessing and a curse. If they have a previous chief of staff, talking to them is great and can be helpful, but you need to assess whether they are looking for a replacement of that chief of staff, or they’re looking for someone new who may have a different way of approaching the job. If you’re similar to that person, then it works out great for you. But otherwise, it can be challenging. It can be best to look for execs ready for a step change in their team since it gives me the freedom to do the job with your own unique take on it.

 

• Another helpful question is how long do they plan on keeping the new Chief of Staff? Some people consider it a short-term, rotational role. They have a new person every 1-2 years. So you sprint for 2 years, it can be quite exhausting, and then you spring off into another business area. Other execs might have someone for many years and don’t want to keep changing.There is no right or wrong here, just a matter of what suits you.

 

• I also find it helpful to ask if they’ll commit to having a weekly 1:1 with me. Even if they’re doing bi-weeklys with others on the team, I think this is incredibly important. If they don’t want to do that, you won’t be in lockstep with your VP. I’ve declined jobs because of that.

 

The thing to understand is that to be an effective complement to your exec, you need to be aligned. You need to feel comfortable making decisions on their behalf. You shouldn’t have to worry about being wrong. If you have to keep saying “I’ll get back to you” for important decisions - your impact and effectiveness is diminished. You want to know what they think and be able to decide on the spot. You don’t want to have a constant sense of imposter syndrome.

 

LED: Any resources that you’d recommend for people interested in this role?

 

Luke: This is a really good article by Harvard Business Review on Chief of Staff - they talk about the different levels of Chief of Staff, which is helpful for people to understand. Other than that, remember that having that blood type match is helpful. Think about your role as being the Chief of Staff for the whole organization. Think about how you can make each minute well utilized for the organization. You’re the connective tissue who ensures the right people and right tools are present, for people to make the right decisions at all times.