Issue 23: Delegating as a Chief of Staff
When you're being passed projects and initiatives, how do you ensure that you get everything done without being overwhelmed and overworked?
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This week’s issue is guest authored by Sonja Manning. Sonja is the former Chief of Staff at Levels Health where she managed 150+ active delegations with executive assistants (EAs) and coached members of the Levels executive team on systems thinking and delegation. Sonja now consults with health-tech brands and is passionate about helping people and organizations scale their time and impact.
In this week’s issue, Sonja will be sharing delegation lessons she has learned and tactics that you can use to become a super-delegator.
Why does a Chief of Staff need to be a good delegator and systems thinker?
As a Chief of Staff, your role involves managing your principal’s priorities and projects. After a meeting with your principal, you often come away with an updated list of initiatives and follow ups that you are now responsible for seeing through. But what happens after you receive these delegations? If you simply receive delegations, but don’t automate, systematize, offload, or delegate those tasks, you’ll find your plate eternally full and often feel as though you are underwater. Raise your hand if you’ve ever felt this way before ✋🏼🙋♀️
As I wrote prior in a First Round article about scaling your time as a Chief of Staff, you are often the one creating leverage for your principal, but you, yourself, also need leverage. One of the first things I learned was that I needed to let go of and unlearn the idea that a full - or overflowing - plate meant I was adding value. In startup cultures especially, there’s a misconception that if you’re not “busy,” you’re not adding value. True value means creating space for both your executive and yourself while simultaneously scaling impact together.
In most venture-backed start-ups where money can be a more limited commodity, time becomes your greatest resource. That’s why it’s so important to be able to manage your own time well, in addition to gatekeeping and managing your principal’s time. In my own experience as a Chief of Staff for a venture backed start-up where I was often making the decision to trade money for time, time almost always won.
At Levels, the leadership team deployed a pool of executive assistants through Athena to help scale all team members' time, regardless of seniority. It became up to the individuals on the team to best utilize these EAs and take back their own time. On the Levels team, there were super-delegators as well as team members who had zero delegations. As a super-delegator myself, I launched an initiative to increase the systems thinking and delegation skills of the team.
🤷🏻♀️ What constitutes being a “good delegator”?
To be a good delegator, first you have to be a systems thinker. Systems thinking consists of understanding how events, behaviors, tasks, problems etc. relate and how they can prevail and sustain over time. The outcome of being a systems thinker is the ability to expand the possible courses of action and choices available, creating more leverage for yourself as well as long-term, sustainable processes and solutions.
Delegation is one of the biggest tools in a systems thinker’s toolbox. Being a good delegator means:
Consistently recognizing opportunities to save and scale time by outsourcing or automating tasks, and building processes
Breaking up a goal and its subsequent tasks into smaller parts and teeing those tasks up for action by others
Documenting tasks so that delegated parties can refer to and repeat those tasks in a consistent manner
Continuing to coach and supervise others who have been assigned those tasks
Recognizing when the task needs to be modified or even eliminated entirely because it no longer serves the original goal or purpose
As Levels CEO, Sam Corcos, said in his First Round article on How to Make Delegation Your Superpower, “Learning how to delegate effectively is perhaps the single most important skill that folks need to develop in order to transition into a leadership role, and yet, many are reluctant to embrace it.”
💡 Why delegation matters - especially if you are a Chief of Staff
It often takes a bit more time and effort upfront to employ a systems thinking perspective to launch delegations, but it ultimately saves time and increases impact once the solution is implemented.
Why delegating matters:
Increases individual and team leverage
This is key amongst the leadership team, which has ripple effects to their teams. As headcount and complexity increases this is especially important!
Maximizes impact and output with constrained resources
Especially important the economic market we’re in now where just about every company is being asked to do more with less
Enables deep, meaningful work - what we all want, right?
Helps fight against burnout (last, but certainly not least!)
🦾 Why it’s hard to build delegations skills
Employing systems thinking and continuous delegation is like a muscle that must continue to be flexed. Muscles must continually be worked to get stronger and avoid atrophy.
I’ve found many peers and colleagues are hesitant to start delegating. I’ve heard variations of the following statements many times:
“I feel too underwater to start delegating”
“By the time I set up the delegation, I could have done it myself”
“I am the only one who can do this task”
“It’s too early to start to outsource or hand-off part of this”
“My work is too complicated to break up into context independent tasks”
Do any of these resonate with you? If so, I’ve been there! But if you caught yourself nodding along to any of those statements, it is a sign you need to start delegating and adding more systems (and not tasks) to your work.
👀 What delegation looked like in my Chief of Staff role at Levels
Working with EAs and paying for tools to save time was part of the culture at Levels. As I said before, it’s not just about the tools, but the shared mindset and value of time and efficiency.
I quickly took advantage of the delegation culture and became one of Levels’ top delegators, working with two full-time executive assistants and then coaching other executives and their respective assistants. Over the course of a few months, people within every single function at Levels (e.g., engineering, legal, product, growth) were delegating and automating aspects of their work.
In my Chief of Staff role, I found it helpful to think about delegations in the following categories:
👆🏼 One time: Teeing up an email for my principal, consolidating everything needed for a content shoot into one list, adding hyperlinks to a long blog post, starting the first draft of a memo
📆 Daily: Inputting meeting notes into corresponding item, maintaining my time and calendar auditing
⭐️ Monthly: Updating monthly reports and trackers, maintaining my CRM and my principal’s CRM
⚙️ End-to-end systems: Getting EAs involved in the end-to-end process for all of Levels Digital media from creation, distribution, engagement and analytics
For more concrete examples, here is a Loom I did for the Levels team highlighting some of the delegations I leveraged most when it was my turn to share “Delegation of the Week” inspiration.
🎯 How to get started with delegation - whether or not you have an EA pool
If you currently don’t have access to EAs, the best place to start is building the case for why your company should invest in an EA pool that can be shared across the company. This is a simple return on investment (ROI) and return on time (ROT) business case. Take for example an employee with a salary of $200K a year, and then an executive assistant for $50K a year. Both the employee and executive assistant work full-time, and the employee is able to almost double their role output with the support of an EA. It’s a simple business case to get the most leverage out of your employees.
If you already use EAs or believe your company would be amenable to the idea of using EAs, these tips should help you get started. If not, these tips can still be applied within your current workflows!
Write down the tasks you do daily or weekly: For one week, jot down the tasks you do daily or weekly (e.g., creating a meeting notes document, weekly data pull, performance reviews for team members, tracking inventory management). Look at that list and consider which tasks drain energy. Determine if you can delegate, automate, or eliminate those tasks. Remember, the answer is not always to delegate, sometimes it’s just to eliminate outright (I love the Eisenhower Decision matrix for this).
Pro tip: You can even share this list with an EA and have them help you brainstorm how they can help.
Lean into Loom: The fastest way I found to share context or teach an EA or more junior resource how to do a task was to record a Loom of me doing the task. I’d then ask them to record a Loom back repeating the instructions and doing the task themselves, so I could share feedback before they are off to the races.
Start small: Ask the EA or team member to start with one aspect of the task and then build up to delegating the broader system. For example, when I was running the Levels Digital channels I had EAs start by designing one asset from a template, and then over time they started designing all of the assets, and also uploading and posting them.
Delegate the documentation and set-up of the tasks: For a delegation culture to stick, you must build a broader company system around it. Ask the EAs to set up a company-wide database of delegations so all delegations can be searched and indexed. This way employees can search the database for delegation inspiration, and there is a record of delegations that can be revisited and modified as the work evolves.
Build a culture around delegation: To begin to build broader visibility around systems thinking and delegation, find people who are good at delegation and ask them to share a “delegation of the week” or share examples of how they scale their time. One of the initiatives I took on was compiling the “Top 10 most common delegations” and “Top 13 most unique delegations” to both lower the barrier to entry for people to get started and encourage people to think about the art of the possible. The best part? I had one of my EAs put these lists together and I just reviewed them before sending them out!
🕳️ Avoiding common pitfalls with delegation
There are a few pitfalls I noticed when coaching others on delegation, but they are easy to avoid with a few additional systems.
Revisit delegations every 3 months: You don’t want to find yourself adhering to a delegation that doesn’t make sense based on how the work has evolved. I asked my EAs to revisit all delegations every 3 months and suggest which ones should be altered or eliminated entirely. If you feel like your delegations are creating more work to maintain, then it’s time to revisit and adjust.
Consider when the answer is NOT to delegate: Sometimes the answer to saving or scaling time is not to delegate. The answer might be to automate, time-box, or eliminate that task all together. For example, if your EA goes through your emails and copies and pastes them into a separate document for you to review, is that actually better than you just going through your inbox?
Don’t give up after 2 weeks - delegation is a long game! It can be easy to fall back into the delegation traps of feeling too underwater to delegate, or feeling like you could just do it better yourself. Just like strength training, it takes time to build muscle. Don’t give-up after a few workouts, keep at it.
📝 In Summary
Effective delegation boosts leverage, multiplies impact, enables meaningful work, and fights burnout. Chiefs of Staff need to adopt a systems thinking mindset in order to make the most of delegation. Many hesitate to begin delegating due to feeling overwhelmed, thinking tasks are too complex, or assuming they can do tasks faster themselves, but overcoming these beliefs is essential for scaling your time and impact.
Start by identifying daily and weekly tasks that can be delegated, automated, or eliminated. Consider using executive assistants (EAs) and invest in building a company-wide culture around valuing time and efficiency. It’s not just about the tools, but the mindset. Last but not least, revisit and adjust delegations regularly! You got this 💪🏼
If you are interested in supercharging your or your team’s systems thinking and delegation skills, reach out to Sonja Manning directly to learn more.
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Additional Chief of Staff Related Reads:
Should I Hire a Chief of Staff?
Why Every Startup CEO Needs a Chief of Staff
9 Things You Should Know if You Want to Be a Chief of Staff
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👋🏼 Until the next issue,
Clara
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