Issue 16: Removing Blindspots & Gaining Context as a Chief of Staff
How do you parachute in and start delivering value even if you've never done it before?
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What strategies can a Chief of Staff use to quickly become well-versed in unfamiliar topics?
One of the most difficult things about being a Chief of Staff is the sheer amount of information that you have to process. As a right hand to an executive, and oftentimes a CEO, you’re dealing with deluges of information and inputs from all levels of the organization. In addition to that, you’re also often presented with projects and initiatives where you might not have direct experience in those areas, but are still expected to deliver quality solutions. While it’s impossible to become an expert in everything, there are ways that you can supplement your knowledge gaps and be an effective and successful Chief of Staff.
In today’s issue, we’ll be going over 4 methods that you can use to gain better understanding in unfamiliar contexts and situations. Even if you’re not in a Chief of Staff role yet, you can still practice these techniques in your current role and pick up a wider perspective of your team and organization as a whole.
1️⃣ Start with Self: If you’ve heard me talk about any one skill that any Chief of Staff needs to master above all, it’s self awareness - in fact, it’s the first thing I listed in the second issue of this newsletter: What skills do I need to become a Chief of Staff? When you step into a Chief of Staff role, it’s important to take stock of what you know and what you don’t know.
When I was a Chief of Staff at Hugging Face (at the time, a Series A NLP/AI startup), I had a clear understanding of what my known strengths (known knowns) and weaknesses (known unknowns) were. I knew that I was a startup operator and that anything surrounding operational processes would be in my wheelhouse. I also knew that I was not technical or an engineer and that my knowledge when it came to AI and machine learning was a huge gap. What was hardest to figure out were my blindspots (unknown unknowns). Your blindspots are things you’re neither aware of nor understand. Through listening tours and feedback from my principal, I realized that I had knowledge gaps when it came to fundraising and board presentations, cap tables and external stakeholder management, just to name a few.
By working on your self awareness, you’re able to uncover what you don’t know and take steps to combat that. For me, it was reading up on the latest news around AI. I subscribed to newsletters that covered the topics, set up alerts around our competitors, and took the opportunity to ask our engineers and scientists to link me to whatever they were reading, regardless of how dense or how much Googling I would have to do to understand the white papers. I also asked ruthlessly for feedback from my principal, establishing a weekly cadence for me to receive it.
2️⃣ Ask the right questions: Once you’re aware of what your blindspots and knowledge gaps are, you can start to fill those in. In a panel I led called “Parachuting in & Delegating out,” Chief of Staff at Wise Systems, Ellise McDonald, says that “[Because] you’re working with stakeholders in all different areas of the company, you have to peel back the layers of the onion and ask the right questions so that you’re getting the right answers.”
In this HBR article, “The Surprising Power of Questions,” authors Alison Wood Brooks and Leslie K. John posit that “Asking a lot of questions unlocks learning and improves interpersonal bonding.” Leading with curiosity will allow other members of your team to start supplying you with additional information down the line, further filling in your context gaps. Also, being specifically goal oriented in your question asking will get you a lot further in gaining the context you need.
Another great resource that I’ve referred to time and time again is The Mom Test. While the book is focused on talking to customers and validating business ideas, many of the questioning tactics can be reconfigured to help you uncover the true underlying problems and challenges of your organization.
3️⃣ Invest in using Mental Models: Mental models are shortcuts that we can use to better understand the world at large. In the context of a Chief of Staff, it means being able to apply context from other situations to the challenge at hand, even if it’s not a 1:1 to comparison.
A mental model gives you a representation of how something works, even if you don’t understand each and every nuanced process. By growing your lattice of mental models, you’re better able to connect puzzle pieces that might sometimes feel disparate. Mental models are best exemplified by David Epstein’s book, Range, a must read for any Chief of Staff who wonders how to put their wide range of experiences into practice. If you’re able to translate other experiences that you might have had into the problem in front of you, you’ll unlock a greater range of solutions you can offer.
One example of me putting this into practice was when I was running On Deck’s Chief of Staff fellowship. While I had never managed a community of Chiefs of Staff specifically, during my time as a Chief of Staff, we had a large open source community contributing to our library. Previously, I had also worked at a dance fitness company where we had hundreds of instructors in a community as well. Drawing from my experiences and pairing it with First Principles Thinking, I distilled down some key aspects that I thought made communities successful:
People look to communities for a sense of belonging
People join communities to help enhance a certain part of their lives
People find values in communities when they feel like their unique challenges or experiences are addressed
By upholding these principles (and also healthily questioning whether or not they remained true as I continued to build), I was able to translate past experience into applicable action.
For a list of common mental models, check out Farnam Street’s “Mental Models: The Best Way to Make Intelligent Decisions (~100 Models Explained).”
4️⃣ Use your network: By relying on your networks, you can tap into the knowledge and expertise of others. Chances are, you’re not the first person to ever come across a problem and there are others who have solved something similar before. Identifying the right people and leaning on those with credentials can help you learn context and information much quicker than starting a new knowledge search from scratch.
For example, a Chief of Staff might be tasked with creating and implementing a parental leave policy when they don’t have a formal background in HR or People (this was me in day 2 of my role). While I did have about 15 tabs open in my browser Googling various variations of “how to come up with a parental leave policy,” my second course of action was to reach out to friends at companies that I knew had great parental leave policies that I could seek to emulate. I also looked around my LinkedIn network to see which HR professionals I knew and reached out to the former Head of HR at a previous company to schedule time to chat with her. By gathering information and knowledge from personal connections, I knew I could go to any of them with follow up questions if I hit any roadblocks. As a result, I was able to put together a proposal for parental leave by the end of the day and have it implemented by week’s end.
I’m a huge advocate of not going at this role alone. Find spaces and communities where you can build a personal brain trust and board of advisors. Expand your network and where you have knowledge gaps, have a trusted connection or two who can help you get up speed.
As a shameless plug, the Ask a Chief of Staff community is a great space for Chiefs of Staff who are looking to build connections and learn from others who are in and have done the role before. Applications are technically closed but for Ask a Chief of Staff readers, we’re keeping the waitlist open for just one more day!
Hope you’ve enjoyed the latest issue of this newsletter and we’re looking to you for future newsletter topics! If you have any questions around being a Chief of Staff, tactical takeaways that you can apply, or other curiosities about the Chief of Staff role, submit a question below and we’ll answer it in a future newsletter issue:
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May 9th: Building and Evolving the Relationship with Your Principal
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Additional Chief of Staff Related Reads:
Ask a Chief of Staff: Parachuting in & Delegating out [Panel]
Owning your “atypical” career path
My first year as Chief of Staff
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👋🏼 Until the next issue,
Clara
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