At the end of December in 2021 Helcim’s CEO Nic emailed over a Google Doc titled “Chief of Staff - Job Posting Dec 2021” with no context and the note that I was invited to edit the doc. This was a normal occurrence, I would regularly edit and review content for Nic before it was sent out. So I reviewed the doc, made some suggestions, and sent back a “Looks good” note.
Shortly after sending back the doc with edits, we jumped on a video call and Nic explained how the role had been recommended to him by his CEO circle as a solution to feeling stretched too thin and like there were too many balls in the air at any one time. Since taking on this role I’ve learned that each principal will have different competencies they want from their CoS, part of what makes this role so unique, in our case, Nic was looking for someone with a deep understanding of the company (thus looking internally not externally), strong communication skills, and the ability to connect different departments and people as the company grew. He then asked if I would be interested in the role.
It was one of those moments where you just have to put your hand up and say yes then figure out the rest later.
Below are some lessons I’ve learned in that time. What makes the Chief of Staff role so interesting in my opinion is how unique it is to both the company the role is with, the individual who is doing the role, and the principle the role is supporting. While there may be similarities and overarching themes for the position, each CoS will have their own experience. These lessons are based on my experience as a Marketing professional turned CoS at a fintech startup that grew to a Series A company supporting the CEO.
Embrace the unknown:
The position was a new role at Helcim so while there was an idea behind why it would be useful, how it would add value and some semblance of what the general purpose would be, there were also a lot of unknowns. Combined with the general nature of a Startup which is always changing, there was very little regularity in the day-to-day. After about eight months in the role some recurring themes did start to occur to balance out unknown work with known work. Now that we’re 18 months into the role there’s a balance between special projects and one-off work with regular activities including board reporting, shareholder communications, internal communications, and regularly held company meetings.
Responsible for everything, owner of nothing:
One of the coolest parts of working in a CoS role is getting to work with every department at a company. You’re not siloed into one specific function or area, if there’s a department that has a special project or needs a hand with something then there can be an opportunity for you to jump in and work with that team for a bit. This has helped with my business understanding, skill development, and ability to connect the dots across the organization. It also means that everything is your problem, there’s no delegating to someone else or saying oh “so-and-so” will fix that. You need to care about every concern, fire, and roadblock across every team all the time. The added challenge to this is that while you have a responsibility to find a solution you don’t own that function so having strong relationships with other members of senior leadership so you can work together is crucial to being effective in finding these solutions.
The role can be lonely, so create your own community:
The CoS role has some unique attributes that can make it feel lonely compared to other roles people probably experienced before moving into it. First, in many cases you’re not working as part of a direct team so you might find you miss out on some of the camaraderie and support that other IC roles are used to. In my case, I moved from a very tight knit marketing team where there were always people to brainstorm, collaborate, and bounce ideas off of to working in a more solo position.
Second, unlike a traditional IC to manager relationship, working as a CoS means you’re solving problems for your principle, not bringing problems to your principle. This is a dynamic that can take a bit of adjusting to and it helps to build relationships with CoS community groups to build up a community of people who understand your work and face similar challenges to you. Huge shout out here to the Chief of Staff Network who has been my online community while navigating this role (and kudos to their great SEO at being the first returned result when I naively searched “chief of staff network” one month into my role hoping to find some type of network)
You get to practice context switching constantly:
Referencing back to the point above about being responsible for everything and the owner of nothing there is no such thing as an “off limits” or “that’s not my area” question. From strategy, product development, marketing, expense reports, interpersonal issues, and more. The context switching I have found the most difficult is when multiple departments ask about a shared project without providing a lot of context for where their question is coming from. In these cases I have to remind myself to pause and ask clarifying questions before answering, otherwise I’ll answer from the lens I was most recently looking at the issue from which is probably not what they were hoping to learn. This extreme level of context switching is something common at C-Suite level roles and is a great way to crash course your way into what is required to operate on that level.
I’ll figure it out will become your mantra:
Part of the fun of working at a fast growing startup is that no two days are the same and you’re often tackling new challenges without any defined processes or in-house experts. This also means not knowing how to do something isn’t a good enough reason to not do it. We’re incredibly lucky to have a team of people who are always willing to dig into the unknown and figure things out. The CoS role gets to learn the unique backgrounds and pockets of knowledge housed throughout the company to call on different people to help solve the unknowns that will inevitably come up each week. This is also where the external community groups can come in handy to see how other companies have tackled a specific issue and what advice they would give now that they’re on the other side of it.
Feedback is a gift:
Creating a culture of feedback has been really important to Helcim to ensure we’re regularly hearing from all the different teams and identifying any potential blind spots or areas for improvement before they become an issue. I would say we have been quite effective at doing this and the team will regularly volunteer feedback and ideas. As CoS I have found it can be challenging at times to ensure I am digesting feedback properly so it can be redirected to the right groups for action. Usually this occurs during particularly challenging weeks where it can feel like feedback is piling on as complaints. In these cases taking a break to reframe the intention and my response is particularly important. We are a team of people with good intentions who want to make the company better - keeping this in mind helps ensure feedback is always received as a gift and not as a complaint.
You need to be able to work in sync and async:
Most CoS positions require a mix of collaboration with the principal and individual work. While we check in regularly for alignment and to adjust as needed, both myself and Nic have individual projects that we action separately along with the projects that we’re collaborating on together.
This lesson will vary based on the company but what we have found works well is having regular stand up meetings and a running doc to keep a quick operating cadence on all projects and questions. Recognizing that life (and startups) rarely go as planned, so we have put structures in place that allow us to pivot to working async without missing anything. Our living doc is the catch all for comments and thoughts and we use a color coded system to go back and forth on updates and requests.
Just keep asking questions:
Between context switching, a broad domain, and a complicated industry there’s no such thing as too many questions. As someone who can struggle to speak up it took a while to get comfortable pausing a conversation and asking questions before continuing the discussion. The more questions I ask the better clarity and alignment everyone on the team ends up having.
Holding the CEO accountable:
While healthy debate and an exchange of ideas is part of any good working relationship, it’s always slightly uncomfortable for a direct report to challenge their boss. Even more so when your boss is the CEO of the company and you’re the person responsible for giving that candid feedback in moments when they are ready to move full steam ahead with an idea or majorly shake up something at the company. Most founders are ambitious people. Full of ideas and wanting to do everything right now. Challenging them in a constructive way and holding them accountable is uncomfortable at best. This is an area of the role where the imposter syndrome and self doubt creeps in the most “who am I to question the CEO, I don’t know any better”. Building trust in the relationship goes a long way to make space to challenge the CEO when you disagree so that you’re heard and the conflict remains constructive.
What’s next?
When we initially outlined the position the plan was to make it a rotational role, a 24 month tour and then move on to another role within the company. Yet when we passed that mark, we collectively decided that the great dynamic that we have built is worth continuing to see where it evolves to.
This is another unique part of the role and why people are attracted to the position. Many CoS positions are on the job training for other C-Suite roles within the company, or give the CoS exposure and training on how to become CEOs themselves as they branch off and launch their own ventures. Then there’s the category I fall into - the people who look at the CoS position as a career role. I find the behind the scenes work supporting founders and execs in growing their companies the most fulfilling work and that's where I want to stay for now.
By - Miranda Russell
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