So, You Think You Want to be a Chief of Staff?



There has been a lot of buzz lately about the chief of staff role, which has exploded in popularity recently. This tweet from Gokul Rajaram, Product and Business Helper at DoorDash, in which he says “one of the best startup hacks I've seen is hiring a smart generalist to own the numerous random yet critical projects that need an owner. From sourcing talent to creating customer decks to sending investor updates, they can be a massive accelerant to your business,” received almost 3.5K likes and a laundry list of comments and questions from followers on the role at press time.


Tyler Parris, author of Chief of Staff, The Strategic Partner Who Will Revolutionize Your Organization and founder of chiefofstaff.expert, and I also hopped onto Clubhouse recently to explore the conversation further and share our expertise on all things chief of staff. It’s hard to find much data around the role, but one recent placement that Tyler worked on yielded 800 applicants. Word is out – the chief of staff role can be a springboard for your career. But is it for everyone? And what does it take?


We’ve talked at length about how a chief of staff is a smart generalist, a Jack/Jill-of-all-trades. We’ve even referred numerous times to the chief of staff as the “right hand” of the founder or CEO. The chief of staff role can also be extremely versatile, dependent upon the personality filling the position as well as the needs of the founder they’re working for. But it’s not enough to just present yourself as a generalist who has done different things in your career.


There are a few considerations to keep in mind when you are exploring whether the chief of staff role is right for you. One great place to start is to read our post on what executives should look for in hiring a superstar chief of staff. Next, consider your starting point. Here are some common backgrounds for chiefs of staff:

Project and program management

  • If you can demonstrate experience handling multiple priorities and understanding how to organize and delegate for the best outcomes towards organizational goals, you may be a good fit for a chief of staff position. Experience motivating teams around projects of multiple scale, ensuring quality work that meets (or exceeds) deadlines is an added bonus.

  • Program management aligns closer with the chief of staff role than project management because of the ongoing nature of the work, the scope and scale of programs tending to be bigger and more complex than projects, and because you can manage a large portfolio of projects really well and still be somewhat myopically focused within a department or function. You might not be exposed to executive leaders, the complexity or fluidity of decisions executive leaders make, or influence the bigger-picture strategy of the company.

Operations management

  • Beyond creating internal efficiencies within the company, the chief of staff also thinks about strategy and making sure the business is meeting the right needs in the marketplace by understanding geopolitics, demographics, regulatory landscape, and other factors influencing your organization’s direction.

  • The chief of staff is also responsible for facilitating the right stakeholders to set that strategy, assessing organizational capabilities and readiness today; doing some organizational design, like managing your executive’s leadership brand and platform; ensuring key messages are being communicated consistently to external as well as internal audiences.

Consulting

  • If you’re bringing experience from the consulting arena, be prepared to show the results of all the frameworks, models, and strategies you helped put in place, and how you didn’t just implement them but followed through.

Communications

  • Not everybody with a communications background is a natural fit for the chief of staff role. Executive speechwriters function well because they have experience helping executives think through problems, ask rude Q&A, and drive clarity of thinking before they wordsmith messages in various media. You’ll need to show how you add value beyond social media strategies.

People Ops

  • A lot of startups, as they grow, have needs for organizational design, recruiting efficiencies, and other tasks in the “people” bucket. But if those aren’t their main challenge, you’ll need to show how you can wrangle heated discussions about how the technology/product works or what it can do and steer that team to shared context and commitment.

Executive assistants

  • The chief of staff really is a different skill set, and some executive assistants may come with that skill set or build it over time, but you need to be operating at a very strategic level and be able to be a true thought partner to the executive, not just a "yes man.”

Note that none of these experiences are sufficient by themselves. For each of these, there are dots you’ll need to connect for a potential employer to have a higher chance of success at landing a chief of staff job.

Lastly, you’ll want to consider context. What makes you good in one environment might or might not translate to another. Here are some key variances in the chief of staff role to keep in mind when exploring whether or not the role is a good fit for you:


Different types of chiefs of staff

  • While there are a few different models out there to explore the different types of chiefs of staff, from McKinsey’s five roles and four archetypes to Dan Ciampa’s three levels in this article in the Harvard Business Review, you need to have a clear understanding of which specific role you’re applying for and how your strengths match up (or don’t).

Different needs by type of organization

  • If you’ve worked in services companies, how will you translate your experience to a product company? If you’ve worked at a software as a services company, how will you hit the ground running in a wearables tech company with hardware, supply chains, and distribution challenges? Also, if you’re coming or going to the public sector or the nonprofit realm, you’ll want to do your homework to find out what will be different.

Different resources and structure

  • If you’ve only worked at big companies up until this point in your career, you might want to figure out how to perform the chief of staff role in a company with no support structures in place. Alternatively, if you have worked in a Series A startup with less than 100 employees, how does that apply to moving a team of thousands at a company like Microsoft or Google?

Different leaders

  • If you are applying for a role where there is a relationally-orientated and charismatic leader, think about the challenges inherent in that leader’s style and their strengths and how you’ll complement or amplify those. What about a detail-oriented or technical leader? It would be really different.

  • It’s important to think about the kind of person you want to work for, which is ideally also the personality type that you best get along with and relate to, because in some cases you’ll be spending more time with the executive than their spouse does.

So is the chief of staff role right for you? While it’s certainly become a hot topic and the need for a business generalist only continues to grow as more and more startups and entrepreneurs break out into the marketplace, it’s worth taking some time to reflect on your experiences and the realities of the role to explore whether it’s a good fit for your career.


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