💼 Founder Feature: Clara Ma
Founder and CEO at Ask a Chief of Staff
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In This Edition
📝 Partner with Chiefs of Staff as Internal Communications
🧡 Surround yourself with community
📚 Embrace learning about topics you’re not an expert in
About Clara
is a Career Generalist who has worked in early-stage startups for the majority of her career. Starting out as a technical recruiter, Clara got her first taste of startup culture while pitching software engineers on the impact they could make at an early-stage company before deciding to join a startup herself. Since then, Clara has found her niche in helping executives turn their visions into reality and she thrives in operations and execution. In Clara's career journey, she's been a Director of Special Projects, Operations Manager, Chief of Staff, and Program Director - all roles that operate in the messy middle of "generalist"! Most recently, Clara has founded “Ask a Chief of Staff” — a business dedicated to matching Chiefs of Staff with executives while providing community and resources for existing and aspiring Chiefs of Staff.
What inspired your professional path?
I didn't really know what I wanted to be when I grew up — it felt crazy to me that I had to make a decision about my career at 21 years old. And so, I took the first job I was offered: I started out as a Technical Recruiter for a boutique recruiting agency where I pitched candidates on why it was a good idea to work at a startup.
Since then, my career has always been at early-stage companies. I felt like I was able to have a lot of impact as a generalist because I had a chance to dabble in different projects where there were still very nebulous titles and job descriptions.
When I was at AngelList, my manager was the Head of Operations, Lexi Lewtan, and she encouraged me to stay wide in my career. I didn't really think that was an option for a long time — a lot of mentors told me to pick a lane and become an expert. But Lexi gave me a lot of different projects with the opportunity to work cross-functionally and find creative solutions.
At that time, the CEO of AngelList Talent (now called Wellfound) was looking for a Chief of Staff. I hadn’t heard of the role before other than in the political sphere, but as I researched it, I realized I could take my generalist skill set to the next level, have access to leadership, be in the room for decision-making conversations and still cultivate a wide skill set.
After that experience, I applied more directly for a Chief of Staff role at a Series A startup: Hugging Face. I had the opportunity to be the Chief of Staff to incredible multi-time CEO and co-founder Clement Delangue. Since then, I’ve dedicated my time to continuing to empower Chiefs of Staff to be more successful in the role and continue to build resources so that they can feel comfortable and successful in this very wide-ranging role.
What is one project that you’re proud of accomplishing over the years?
Being a Chief of Staff can be lonely because you're likely the only one in your organization. It took me a while to realize that you don't have to go at it alone — you can find other people who've done similar work or faced the same challenges. Rather than build from scratch yourself, you can learn from others' experiences. This really became the springboard moment for me stepping in to take over the Chief of Staff Fellowship at On Deck and ultimately my own business, Ask a Chief of Staff.
My journey to my business began with my Chief of Staff experience because I was given access to the business at an unprecedented level and worked so closely with my CEO. I started my Chief of Staff role in February of 2020 when we were still in the office. After a month, we had to pivot to being a remote company because of COVID. I was still in the very nascent stages of building my relationship with my CEO so trying to figure out what exactly the right operating cadence between the two of us would be so that we could still stay in touch and replicate some of those in-office conversations was crucial.
During that time, I also found out about On Deck's Chief of Staff fellowship. It gave me a community and the chance to talk to a lot of other people who were in similar positions. I was able to learn what skillsets I could improve on and which I needed to acquire. I was grateful to find a place where I belonged and was able to take all the learnings that I had and share them with others.
That’s when I decided I would pursue the Chief of Staff industry full-time. I took over the community at On Deck as Program Director and grew it to over 400 members. I continued to learn from the fellows every day. There was a magic to it that I wasn’t quite sure I could replicate so initially when I started my own company, I focused on matching Chiefs of Staff to career opportunities. It was sort of the precursor to joining a Chief of Staff community.
I figured I could help people find a job and then figure out how to best support them in the role moving forward. But as I continued to match Chiefs of Staff with executives, my original community of Chiefs of Staff was still really excited about having a common space to share their knowledge and that spurred me to create a new community that would allow people to do so.
How do Chiefs of Staff embrace internal communications?
Like Switchboard Operators, Chiefs of Staff are the conduits for their companies — translating the leadership’s strategy into execution. That means talking to department heads, managers and individual contributors and turning vision into milestones and metrics.
The translation process is such a crucial part of being a Chief of Staff — we are the ones gathering all of the meeting notes and supporting the leaders who present at major events like Town Halls. We cultivate the communication around the company and synthesize it into a way that's digestible for everyone to understand and be on the same page.
It’s so crucial to have strong communication skills in order to read between the lines: When leadership is saying something, what are you really hearing? A Chief of Staff I admire greatly, Michael Sheets, explains this approach in perfect analogy. When you’re at a wedding, most people look at the bride when she enters the room. But, the Chief of Staff looks at the groom and they're able to tell a lot more about what that relationship actually looks like based on that interaction. It's really about seeing the unseen.
What are the skills needed to succeed in your field?
Firstly, you need to have an extremely high EQ — emotional intelligence. While you have projects and priorities, ultimately, your job is about the people who you work with, getting to know them, collaborating with them, coaching them and supporting them.
Next, it’s the ability to get smart quickly about topics that you don’t know very much about — it’s the parachute in and delegate out technique! You need to be able to make decisions when you only have ~80% of the information. You have to be great at seeking out and finding that knowledge to become the expert in the room. This ranges from business information to HR. On my second day as a Chief of Staff, I was tasked with creating a parental leave policy for our startup. I knew nothing about HR and parental leave policies, but sought out experts and resources to come up with a proposal because it needed to get done.
Finally, excellent communication is key. You need to get everyone to row in the same direction. It's so important that you have a very clear and concise way of expressing yourself that feels natural to you. Develop your internal communications framework — whether it’s a one-page memo or a different approach, find what works for you and learn to speak and communicate on behalf of the leader you support as well.
How do you continue your learning journey?
I learn a lot from others. Many times we feel like we’re alone in our careers, but when you find other people who share similar professional interests, it can turn into your community. Find them, reach out to them and talk to them. I seek out people with curiosity who are exploring new topics and want to learn from each other. I ask for their suggestions on what to read or listen to as well.
Some of my favorite newsletters to follow: Ann Friedman and The Meteor.
I’m also a big fan of peer mentorship and have been engaging with Topknot for the last few months. It’s an incredible platform for millennial women to peer coach each other through challenges and obstacles that we’re facing.
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