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Playbook - Chief of Staff Role - The Role, Hiring, Onboarding

The Chief of Staff Role

Background for the role and this article

The Chief of Staff (CoS) role has emerged from mainly military/governmental organizations and has found its way into private companies. This natural evolution is supposedly caused by the interesting concept of the role and the incredibly empowering impact a CoS can have on the life of an executive and on the company or organization she is employed in.

Despite being very close to the Executive- or C-Level of an organization the CoS is operating mainly behind the scenes, which makes the role so hard to define, describe or scope when hiring a candidate for the job.

This document touches on the potential of the role, provides insight into what impact the role can have in an organization and executive’s life, how it can be hired for as well as trained and how a CoS can develop after successfully completing their tour of duty.

This document is based on publicly available sources that describe the role. Insights are also drawn from my experience as CoS and my interactions with various different Chiefs of Staff from backgrounds ranging from military organizations to established private organizations with 1000s of employees and early- & later-stage startups.

How does an organization/executive benefit from the role?

CoS = Execution & Speed

In startup-world it is all about speed. Speed of adapting, changing direction, implementation or execution.

While it is very important to follow the right strategies to win your market and make good decisions, those strategies have to be implemented and turned into actionable work packages for your team. Without implementation, execution and tracking your strategy does not matter. A CoS can be of high importance for this task due to the close bonds, high level of trust, or informal ways of communication they maintain with your team. That’s why they can get complex things done so quickly.

A CoS can mean you as founder/executive continue to have a life

When defining a CoS role in the very beginning, one of the main goals should be that “the Chief of Staff can replace the executive in internal conversations, external interactions and even decisions”.

Being a founder or executive in a startup can easily turn out to be the most demanding and stressful time of your life. Imagine you have someone by your side who understands the way you think and take decisions and can replace you. Congratulations, you just expanded your capacity by 1,5-2x (if you do a good job choosing and onboarding your CoS, of course).

A CoS can help build a successful culture

I am convinced that culture is the operating system of a successful company.

Why?

In bad times: When your company struggles culture is what makes people stick around and try to turn everything around, even if it’s not in their personal best interest and they could earn more/have an easier life elsewhere.

In good times: When your company is winning, grows quickly, hires a high number of new employees per month and raises new money every few months, culture is exactly as important as in bad times.

Sounds surprising? Well, growing quickly essentially means running a new kind of company every 1-3 months - everything will feel different, has to be managed differently, the team changes and professionalism has to increase, processes have to be adapted etc. The culture you have in your company can be the one thing that provides continuity during this time and can be what enables you to actually grow quickly without failing. If it’s strong enough it’ll help you with onboarding new employees, adapting processes and so much more because it’s the common language everyone understands and signed up for.

Your CoS can be your face towards the team, she will influence a lot of the informal communication and will help people interpret your actions. Empower her to build that culture and make sure you have an aligned understanding of what the culture should look like.

For founders: A CoS is your executive team’s best coach

If you are the founder and are considering working with a CoS this is for you:

Founders are weird. They are a special kind. You are most likely falling into that category, too.

You will sometimes think differently than the people around you do. You will have to take unpopular decisions. You will hurt people. You will freak out, you will shout, you will be unpredictable. You will be under a lot of pressure when things go badly or greatly (both scenarios come with their very own challenges, so you will struggle and be stretched thin). There are many more things I could list here. It’s the things that make you a founder and that will ultimately help you build something other people can’t.

What you will benefit from during all of this time is a translator: Someone who understands how you think, why you think that way and is on your side, someone who has your back.

They are not there to change you. They are there to help manage your team so they understand you. Because they just won’t sometimes. And you will not always understand how to fix it or have the time to do so. Then the right CoS will be your and their hero.

A CoS fills gaps and defines structures

Most startups are understaffed, either due to constraints in cash or their growth which is always ahead of their recruiting efforts.

This means that when your company is small and you need to execute new initiatives they will not always fall into someone’s area of responsibility, simply because you haven’t built that very department yet. A CoS can be very hands-on in these early phases and help you execute faster.

When you grow you will need good management. No one person can execute all the new initiatives anymore and also shouldn’t if there are people who are responsible for e.g. marketing, sales, HR or other. Now your CoS needs to fill gaps in communication, alignment and whatever else pops up when building a scaling system to manage a company of 50+ people. She has to do a good job at differentiating between just “fixing” something and implementing systems to fill certain gaps long-term. Examples for this can be goal setting mechanisms that lead to clarity, alignment and better execution with less distraction or confusion.

Again, any organization will benefit from someone who can implement and change things quickly due to the trust they have earned with your other leaders.

How to find a person that is able to do so and what to look for can be read below.

What to look for in a Chief of Staff and how to find one

Character & work style

When interacting with CoS from very different organizations, coaching other CoS or advising founders on how to hire one, I eventually broke down the required profile to the following for aspects:

  1. Ability to get shit done, even in a very ambiguous environment and with a lack of information. Prioritize the important stuff and don't freak out over every problem. Let fires burn.
  2. High Emotional Intelligence/Level of Empathy to work with the team. Someone who is not able to connect to people and build trust quickly will not be able to do the job.
  3. Low ego. You serve, you lead from behind, you glue the leadership team and organization together. It can never be about you. It’s really just like glue - without you things might fall apart, but it’s really not easy to spot you.
  4. Quickly growing companies need new structures every 6-12 weeks to function without too much chaos. For that, the candidate needs a natural tendency towards creating structures that solve ACTUAL problems without overengineering. The ideal candidate also needs to be able to communicate the value of the new solutions very clearly to make sure implementation has buy-in.

Number 5, very important: Never hire someone who you could imagine going to your other executives and say that they need to do something because YOU said so.

By simply funneling your commands, your CoS will lose their credibility. If you want that kind of help, look for an assistant. Your CoS is a second you! There is a need to be aligned with them, so they can implement decisions as if you’ve taken them together. It’ll enable them to not always stand in your shadow but to truly become a second version of yourself. Listen to her suggestions, concerns and actually take decisions together with her. It’ll enable you to use them as a sounding board, let them be more independent and build your current CoS into a really good executive at some point.

Complementary skill sets CoS<>Executive

Your CoS needs to have complimentary skills to yours. But the really tricky part is to find someone who has those complimentary skills (a.k.a. sees things differently), but is able to communicate with you in an effective way (a.k.a. can speak with taking into account your way of thinking).

Example: If you as an executive are very analytical it will likely really help you to hire a CoS that has a higher sense for emotional/cultural topics. But that CoS still needs to be able to explain their different POV in an analytical way, too. That way you can appreciate the new aspects that person brought to the situation while actually understanding it.

Hint: It can really help to do the “operating-manual”-task with a founder and his CoS to help them understand how they need to interact with each other in certain situations.

Where to find good candidates

I’ve seen very unusual things work here.

If you’re looking for a CoS to work with a founder, you definitely need a self-starter, some entrepreneurial background on a small scale does definitely help as an indicator here.

On the other side I’ve seen people from outstanding business schools fail in this role due to their inability to act in the background and building a track record through continuous outstanding work but rather thinking from a career-building perspective.

I recommend trying to detect and test for the character & work style factors outlined above and making the ability to connect to people one of the higher weighted criteria. The next step would then be to think about if there’s a match between candidate and execute they are meant to work with according to the other factors outlined above. While the CoS search process is not as hard as hard as finding a co-founder, it is in aspects still similar, as the full power of the CoS<>Executive tandem only materializes if the connection between the two is very strong.

How to make a Chief of Staff successful in the job

The feeling of ambiguity in the beginning

Whenever I was working with other CoS or talked to more experienced ones there was one thing standing out: In the beginning the role feels very ambiguous as it’s still unclear what ecosystem you’re playing in (the company, the team, the other executives, perception as CoS), what exactly is needed from you and also how far you can go. For me it even went so far, that I thought: “If we downsize, I’d be the first one to be let go”. The executive working with the CoS needs to do a very good job here by giving guidance, setting clear milestones and also nudging the candidate to act in certain ways expected from her, so she does not have to test out the borders of what is expected vs. what is accepted herself.

The feeling of not feeling appreciated

Achievements as CoS can feel very ambiguous, too. Especially when implementing systems/processes this can even come across as putting bureaucracy into a work environment that was proud about actually not having any of these “corporate” processes. When the company grows, any organization unfortunately needs these processes and the CoS is often the one seeing the need for them first and implementing them.

Celebrating those responsibilities as achievements and showing appreciation for them can be very important for the CoS’ performance in the job.

The feeling of not knowing how to navigate difficult situations

When talking to new CoS they sometimes have a hard time to understand how to navigate certain situations. One common challenge is that the CoS might now know whom they can share what information with (which they potentially have obtained through informal channels) without losing their credibility or hurting trust. Another one is getting people to do controversial things by not saying that the CoS’s executives demanded these, but by actually convincing the team that it’s in their and the company’s best interest. If the CoS uses their executives’ command as a reason to do something, they lose their credibility.

The feeling of not knowing what’s next

Almost every CoS is wondering how they can develop after their tour of duty.

Often a CoS develops into a leading role in their current company, either as a general leader or an expert for a topic they fell in love with during their CoS duty.

While the role was widely unknown in Europe before, you could really see it pick up traction in the last 12-18 months. This also opens up the possibility of moving on to other companies in either a CoS capacity again or another managerial role, as HR professionals get better and better at understanding the potential abilities of former CoS.

The graph and links below give an interesting insight into how this could go:

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Collection of especially interesting resources found online: