What’s the deal with the Chief of Staff role?

The Chief of Staff (CoS) role has recently become quite coveted, especially in startup land. This makes sense given startups in growth mode can be messy and unpredictable so hiring a chief of staff to augment the CEO and existing team capability can potentially achieve growth faster than hiring specific people for specific roles.

I have done two turns of the Chief of Staff role and will share what I did in the role, the key skills required for the role, some challenges and some recommended resources. Please note that the role of the CoS by its very nature differs by company, by CEO, by the skills of the CoS and by the existing capabilities of the teams in place. So, the below is my perspective only and not representative of other CoS experiences. I would love to hear from other CoSs on how your experience differs!

Overall thoughts on the role

The overall objective of a CoS role is to amplify existing efforts and help the CEO and the leadership team be sucessful.

I think the beauty of the CoS role (and why it’s now so appealing for startups) is that it is fluid, and will be moulded to what the CEO and the company needs — filling gaps that exist from what needs to be done vs the existing team’s capabilities, if alternatives aren’t suitable. By this I mean that a CoS is not an expert in everything (there will always be others that are much more qualified to complete a particular task) but a CoS has the advantage of having a deep understanding of the business and fluidity in their job description so are able to re-direct their focus when required quickly and without much fuss. For example, if an unexpected short project comes up, in the time it takes to just hire and onboard an external project manager (potentially 2–4 weeks), the CoS might have already completed the project.

What I did functionally ⚙️

My main focus was CEO success but I also had set responsibilities around strategy development and execution, and then a bunch of “other things”.

1. CEO success

The CoS’s customer is the CEO so my focus was on making sure the CEO was supported. In my roles I acted as a:

• Stunt double — take onboard a portion of the CEO’s tasks, such as attending meetings in their place, onboarding new members of the leadership team or having 1:1s with employees if the CEO is busy fighting fires
• Information synthesizer — draft CEO communications, research, write briefs and prepare CEO ahead of key meetings
• Confidante and cheerleader — give the candid and honest feedback they might not receive from direct reports or employees, be there for each other during tough days
• Air traffic controller — the CEO has so many competing priorities (a Board to appease! Customer issues blowing up! New competitor!). If you happen to be working with a very visionary CEO, they can also get very passionate about new ideas which is great — that’s why they are a CEO. But the best thing you can do for them (and therefore the team) is to keep them on track with the key priorities but make sure there is space in your operating rhythm to address amazing new ideas, a plan to address the competitor, etc.

2. Strategy development and execution

This involved partnering with the CEO and the leadership team to develop the strategy and drive the execution of the strategy. Key responsibilities included:

• Driving the regular strategy planning cycle — i.e. organising strategic offsites, collating and sharing insights that inform strategy (industry, competitor, customer, employee insights), facilitating workshops and synthesizing ideas to create strategy presentations and outputs (e.g. Board reports)
• Owner of the operating rhythm — the operating rhythm or “heartbeat” of a company is the regular cadence of events or meetings where communication and decision making happens, in order to execute, review and adjust the strategy. This could include events like daily huddles, weekly team meetings, fortnightly employee 1:1s, monthly all hands and quarterly resets. I worked with the CEO to design the cadence rhythm and the systems required to facilitate the rhythm (e.g. meeting agendas, templates)
• Program and project management — the output of our strategy was a distinct program of initiatives which required overall program oversight. My role was run a program management office to help unblock individual project leads if they ran into issues, manage dependencies between the various projects and created dashboards and Board reports. I also acted as a project lead if required.

3. Other things

This is the fluidity I was talking about up above in the overall thoughts section. It’s also the really fun part of the role and involved being a:

• Bencher — step in to do things where there is no natural owner and where it might not make sense to hire an external person to do the job or to divert someone from their existing responsibilities. E.g. I took over as a temporary product manager when our PM left until we found a full time PM
• Fight fires — issues might come up in teams where they need some additional support and manpower. E.g. Onboarding team have a huge backlog and need additional support to work through process blockages
• Operations and processes — support other teams with creating new processes, review and update ineffective processes
• Integrator and connector — one of the most valuable “value-adds” of having a CoS. Working across all business functions means that you will see the business end to end. That is a privileged position to be in so it was important to share insights back. E.g. if someone in one team is working on something someone else is working on in a different team — connect these people

What are the skills required? ‍🔧

Having a consulting background helped, but not required. I think the below skills are critical:

• Trusting relationship with CEO —having a strong and trusting partnership is crucial. It’s also good to have an understanding of where your individual strengths and interests lie so you can divide tasks based on these skills and preferences
• Personal systems — don’t become a black hole where inputs come to you and then go nowhere. When inputs come in, they should go through your personal triage system and dealt with accordingly. E.g. if the CEO raises something important, you can aim to provide an update on this issue daily until it is mediated. If the CEO raises an offhand idea, it can get filed in your “not as important” list and you might raise it again in a week’s time to find that it’s no longer important
• The ability to build trusting relationships — it will be really hard to get anything done with people who don’t report to you unless you have this skill. And in most cases you won’t have anyone reporting to you so everything has to be done through influence
• A few essential tools in the toolkit — I think it’s good to have a basic understanding of project and program management, of how to run a good meeting, issue based problem solving and the ability to communicate well and ask good questions

Some challenges I encountered 🤦

• Setting KPIs was difficult — In one role, I just copied and pasted the CEO’s KPIs. HR was not impressed. In another role, I had to change my KPIs so often because the responsibilities kept changing. Looking back, given that this is primarily a CEO success role, maybe something like a CEO feedback or NPS score might have worked better?
• Confusion about what my role was — I often got confused for the CEO’s EA and at one stage the HR team also thought they were reporting to me (because I was a Chief of “Staff”). For these reasons my role publicly was never Chief of Staff. This is now less of an issue as the CoS role is gaining more traction and understanding
• People refusing to work with me because they wanted to deal directly with the CEO — this was a tricky one to manage. The good thing is that the people who find it an issue don’t usually stick around for long. They usually know they are underperforming and feel the need to be directly visible to the CEO to compensate for this. If it happens definitely raise this with your CEO.

Recommended resources 📚

• Getting Things Done by David Allen — personal systems 101 so you don’t become a black hole
• Scaling Up by Verne Harnish — scaling a business 101 for those who don’t come from a business background