The Secrets of the Chief of Staff Role
Never before has the Chief of Staff role been more en vogue in Tech. More and more CEOs are opting for hiring these right-hands (or lefts!) to help bolster their executive team’s performance during a period of hyper growth at their organizations. But with the increased attention on the role has come a LOT of noise and bluster…leaving those seeking people to fill the position with many more questions than when they entered the recruiting process.
As someone who has been fortunate enough to serve in the position in a few different kinds of organizations, I’ve had the opportunity to see it play out in a variety of ways that can help those trying to understand more about the position, how it functions in a startup’s system, and how to find the right candidate.
Thinking about hiring a CoS or making the leap yourself? Here are some important things to know:
Our biggest secret is that Every CoS role is different. The role essentially never repeats in function between companies (or even stages). This is largely because it usually exists in direct relation to the CEO's needs and a CoS must choose to either amplify that executive’s strengths when they can’t be present and/or to take care of the pieces of a todo list that may not play to those strengths. A good CoS know their manager’s skillsets inside and out and over time learns when they are supposed to embody their boss, challenge their boss, or take care of something before their boss even needs to find out. The end result is that the position is so dependent upon the work style of the CEO that the role is never the same between organizations. This makes it both incredibly exciting and novel , but also extremely hard to develop a playbook for.
Therefore a Chief of Staff must prioritize communication over everything else. A lot of job descriptions put premiums on organizational skills and the ability to juggle lots of responsibilities, but the truth is that those skills are almost always a function of the existing infrastructure surrounding a CEO. This does not mean that a CEO who lacks that infrastructure can’t hire a CoS to create it, but rather that the delicate nature of the role and its relationship between executive/CoS means that extremely clear and strong communication matters more than anything else. If you’re hiring for a CoS you must must must first and foremost evaluate for communication styles and chemistry. This ultimately means its hard for anyone besides the executive to conduct first-round interviews for the position because only they will know pretty quickly if that person is someone they can trust.
Relatedly, the next most important quality in a Chief of Staff is their integrity and follow-through. In other words, a good CoS must be someone who you can not only trust to have your (and the team’s) best interest, but also someone whose word has power because they treat that responsibility seriously. More often than not an executive hires a CoS because there is already some breakdown in the way that the executive team or the organization works and they’ve discovered that they can’t be the ones to fix it. Therefore, they need to feel confident and comfortable putting a CoS in a position of immediate authority to help suss out the problem, to identify the underlying incentives causing the problem, and to come up with a clear action plan to solve it. In high-pressure/high-stakes situations typical of a CoS job, there often is only one chance to get it right.
Therefore a good CoS must be capable of playing two key simultaneous roles in an organization: Thermometer and Thermostat. As a thermometer, a CoS acts essentially as the Ombudsperson for the company by helping identify the reality of team sentiment while also actively filtering out what feedback reaches the highest levels of the leadership. They must do this by really getting to know the next layer of managers on the team and staying close to the underlying incentives that drive those manager’s performance and benefits. However the job doesn’t just stop there. It also requires having strong enough relationship skills such that a CoS can leverage a manager to help set the tone for executing on projects. In this way, they can sometimes play a foil to the executive or even help bolster the executive’s position when it comes to execution. Thus, a CoS is both a thermometer that takes the temperature and also a thermostat by helping to set it when appropriate.
Because it is such a nuanced role, it often takes a good amount of time for a CoS to build the kinds of relationships necessary to help become the lynchpin that has a multiplier effect on an executive team. I often tell people you won’t notice the impact on the executive team for at least 3-6 months. But, for those executive who have had strong CoS on their team, they know that the effect of paying one person to not only help carry the organizational torch, but also to help them execute on a significantly higher level is unmatched by perhaps any other role in the company.
Lastly, in almost all cases the CoS role is meant to be temporary for any one single person. Reid Hoffman used to talk about the concept of a Tour of Duty; recognizing that most people will not necessarily work for the same company over their entire career. Reid is also a prolific hirer of the CoS position because he knows that the responsibilities of the role allow an individual to graduate into a very different kind of leadership position or move on to an organization with different kinds of challenges. In either case, a CoS drinks from a firehose and ends up moving on more quickly than other tech executives because of it. More often than not, a CoS is a way for an employee to receive not only a crash course education in the inner workings of the business, but a stepping stone to something else. This does not mean that an executive can’t hire multiple CoS over the course of their time as CEO, but rather to see the longevity of the position as lasting anywhere from 1-3 years, and then helping their CoS position their responsibilities in such a way that they serve not only the organization but also their long-term professional goals. Because of the temporary nature of the job, I’ve seen people excel in the role simply because they knew it was more of a sprint and less of a marathon, empowering them (and their executives) to set really clear expectations from the beginning.
The Chief of Staff role is a job unlike any other in Tech: offering accelerated professional development and exposure to the inner workings of an executive team. And, while I’m glad it appears to be having its moment right now, I hope that more folks take the time to really understand the nuances of the position and to plan in advance what it might look like if their next CoS hire is in fact successful. Having at least some clear picture of that expectation helps to ensure a not only a clear hiring process, but also ultimately the likelihood of getting a great candidate in the job.
Thinking about hiring a CoS? Or maybe you’re thinking about the role for yourself? I’m always happy to share what I know! Just reach out.
