Defining success as a Chief of Staff with Sonja Manning at Levels Health

Welcome to the Canvas Podcast, where we bring together business and data leaders to talk about how to make data easier for everyone. Today I'm super excited to have Sonja Manning on the show. She's a Chief of Staff at Levels, and she wrote an incredible blog post about really what it means to be a Chief of Staff and how to excel at the role. And so I figured to bring her on to talk about the role and how it’s evolving with data.

Tell us about yourself!

Absolutely. Thanks for having me, Ryan. My driving purpose in life is to help people realize their potential and live healthy, happy, and full lives. And I've been working on that purpose in multiple ways so far in both my career and personal life.

First, it was enabling clients and organizations to reach their potential as a consultant at Deloitte for six years. Then coaching individuals and groups in spinning yoga classes for almost 10 years. And then at Business School at Michigan and as an advisor at a number of Health and Wellness companies.

And now as the Chief of Staff at Levels and Levels is a Series A company focused on reversing the metabolic health crisis. For those unfamiliar, 93% of Americans in a study that came out earlier this year are not metabolically healthy and have at least one biomarker of metabolic dysfunction.

So solving the metabolic health crisis is perhaps, in my mind, the most important way our society can help people realize their potential and live happy, healthy, and full lives. So working at Levels is definitely the closest I've been to living my driving purpose, both personally and professionally.

What inspired the post you wrote for the First Round Review? How'd you go about researching and writing it? What’d you learn from the process?

So three things inspired me to write the post. One of the things mentioned in the article was just to keep track of my own learnings because, in the fast-paced world of startups, learning compounds quickly and can be fleeting. So the pace of learning is so fast. I knew I wanted to pause at the six-month mark and memorialize the learnings. It was almost a commitment I made to myself when I first started that at six months, I would write an article about it. So if you earn a similar position and you want to set a goal nine months six months from now to write a Medium article or write a post, I had to hold myself accountable for it.

It's just one of the best ways to learn quickly and get exposure really quickly. I think my rate of learning in this role is the fastest rate of learning I've had in any other role in my career to date.

The second reason was I wanted to share some of the incredible learnings I had during my first month. I chatted with over 20 other Chief of Staffs and wanted to amplify and share some of their wisdom. Lastly, probably because time does not scale and content does. And so, part of scaling my time is figuring out where I needed to create content based on the questions I get the most. And I was getting a lot of questions on my main tips of being a Chief of Staff and writing an article and being able to share that with the world, not only hopefully reaching more people, but scaling my own time.

You referenced so many different tidbits from people that are other Chiefs of Staff. How did you go about finding these people? Are there communities that you're in? Did you do cold outreach?

A little bit of all of it. I think one of the best parts of the Chief of Staff role is, everybody is generally the only person in that role at their company. So you don't have an instant community. People are more open to finding community amongst other Chief of Staffs reaching out and saying, “Hey, you know, we're solving this problem. Have you done this yet?” You know, “Have you done OKRs yet?”

People are generally really open and willing to help other people out, which is amazing. And then, I leveraged all of the different networks that I'd been involved in. Levels is supported by A16Z. So our CEO, Sam, sent a note out to their CEO network and said, “Hey, we've got a Chief of Staff. Does anyone else have someone that would be willing to chat?”

I also leveraged my Michigan network and a number of incredible Chief of Staff communities out there that I tapped into, like Voray.

Since this is your first Chief of Staff role, what was your journey into discovering the role and ultimately wanting to join a startup in the role?

So my background was in management consulting and then in business school. And then I went back to management consulting for a little bit. I was always trying to figure out how to combine my personal and professional passions, and while I learned so much in consulting, a lot of the skills I learned in consulting, I'm applying every single day now, especially sort of process and systems thinking, but wasn't quite solving the problems or working on the mission that I really wanted to work on.

I wasn't specifically looking for a Chief of Staff job at the time. I was really looking for problems that I wanted to solve, and I saw the Chief of Staff job description and was just blown away by how I felt like it was the perfect role for me at this stage in my career. I think it's an incredible role for someone who knows they want to be an executive one day.

But you also need enough context and experience with previous work experiences or school to be able to put the pieces together, but really wants a training ground to be able to do a number of different things and figure out what they like the most. So I've always been a generalist. I love being a generalist, I'm a utility player. Part of me doing the Chief of Staff role was trying to come up with the answer to the question of what I want to be. Is it marketing? Is it growth? You know, is it digital? And having exposure to all of those different aspects of the business has helped me refine that a little bit further.

It actually helped me refine that I still love being a generalist. I think there's a career path where I can be a systems builder and a generalist forever. Hopefully, that pans out. I ended up making the transition not specifically for the Chief of Staff role, but what's interesting is now a number of my friends, so people who are at that midpoint in their career and are finding themselves in Chief of Staff roles for probably that exact reason. It's just one of the best ways to learn quickly and get exposure really quickly. I think my rate of learning in this role is the fastest rate of learning I've had in any other role in my career to date.

Part of the job is figuring out the job, it's writing the job description, and changing the job description. At Levels, we do something called area responsibility maps, where every three to six months, we're mapping out what are the primary buckets that we're working on and trying to allocate certain, you know, percentages of time. And every three or six months, my area of responsibility map has looked drastically different. So that is a good sign that I'm continuing to learn and try a bunch of new things.

What has been the most surprising part of the role?

So my expectation of the role going in was that I was gonna be like Leo McGarry on the West Wing as a Big West Wing fan. I was like, this is gonna be great. I am just going to be the right-hand person. And I read the book, the Gatekeepers, which is all about White House Chief of Staff, but it was next to useless for a tech role.

I didn't exactly know what to expect, but from everything I'd read about the role, a lot of it was going to be taking work off of my executive's plate or the executive team's plate and putting it onto my plate. And I quickly learned that if I did that, I would be entirely burnt out and that my job was actually to take work off their plate.

Yes, sometimes certainly put it onto my plate and then figure out how to scale it off both of our plates. So how do I really think of the role as like one plus one equals three? What's the synergy that I can create there? Working, in close partnership with whether it's one executive or the executive team, to scale both of our times and impact because I'm a human being and I only have so much time in the day, and I was originally trying to take things, put them on my plate and realize that that was not going to be the key to success in the role.

So I don't know if that was necessarily surprising, but I quickly realized that being a systems builder is one of the best skills that you can have in a Chief of Staff role in order to keep time and impact for you, for your executives, for their projects, and across the org.

From leadership’s perspective, when is the right time to think about hiring a Chief of Staff? What early indicators might signal it’s time to look for someone in the role?

I think there are two answers to this. If you’re too busy to even hire a Chief of Staff, that’s a great indicator. That's exactly how Casey and the Level's team felt when they put the job description out for my role and invested in the hiring process. It’s also an investment upfront in building trust. There are definitely at least a couple of months where the executive and I were focused on really building trust so I could be her second brain, and one plus one could equal three.

I’m biased but I also think it’s always a great time to hire a Chief of Staff. Even if the company is super early, say five to six people, a Chief of Staff can be a utility player. One of my favorite books is The High Growth Handbook by Eladi Gil. He talks about how invaluable it is to have really early employees that can grow and scale responsibilities to really channel the mindset of CEOs and founders, have trust with the executive team and peers, and have a really deep understanding of the operating procedures and culture. And all of those things are basically table stakes in the Chief of Staff role.

And so, Chief of Staffs with high trust of the CEO and with the executives can move quickly and effectively and start and scale really any function. So since I've started at Levels, I've been able to tap everything from People Ops to Digital, Editorial, and Content. Now I'm in Product, working really closely with our Product team. So in my opinion, it’s always a good time to find someone who can flex across functions.

Besides focusing on building trust, how can executives think about making a Chief of Staff most successful?

One of the things that they did incredibly at setting me up for success was really encouraging me to be that systems builder. They recognized that it was actually going to take probably a little bit more of a time investment for me to start making their life a lot easier, but giving me access to all the information, and helping me really understand the systems would allow me to then scale their time and my time, and it'd be more sustainable for us both in the long run.

The requires an immense amount of vulnerability and trust because not only are they obviously clueing me into the company context and everything that's happening around the orbit of Levels, but into them personally and what our challenges are and what our circles are, and where I can really help.

But to be someone's second brain, you have to be open to being really vulnerable. And I'm so grateful that they are so open with me because it's allowed me to do a much better job at the role than I think if I was working for a Principal that was a bit more guarded or saw the role, or more transactional versus a true partnership.

We’re a complete team. It's not like I'm just reporting to this person. And so I think having the mindset that your Chief of Staff is an extension of you and part of your core team is one of the best sorts of mindsets that a CEO or a Principal can get into to set up themselves and their Chief of Staff for success.

What were some problems that you saw, and what were some systems that you came up with to address those problems?

I'm a huge Notion fan to the extent that I now create weekend itineraries for my friend groups in Notion and send them a Loom overview of the Notion page. I'm a huge nerd on it, so a lot of the systems that we build are in Notion, and we use Loom as well. So those are two tablestakes tools I think we use for sys systems building.

We tried to find areas where there was a lack of information or context that some other type of system, whether it's displaying information, sharing information, retrieving information, or analyzing information, could be useful in, mitigating the time that is spent or sort of the context collapse that's happening.

For example, we have a board of incredible medical advisors, and there was no real system before I joined for anyone in the company to see what all those advisors are up to and really understand what researcher is someone publishing, and who was the last person on our team to reach out to so-and-so for a comment, for editorial, or for a press release.

So that was a really simple system that essentially created a master tracker and half of it's updated by our executive assistants. I do not think I'd be as effective as a systems builder if I didn't employ executive assistants. At Levels, we have. 60 full-time employees and I think 20 full-time executive assistants that are for use by anyone across the company really helps take out some of the sorts of tactical or transactional work of systems building, so as a systems builder, you can focus on more of the strategic elements. So it could be things like creating a system for information to be more visible. Then, because the system works so well, we don't have to have meetings to talk about what advisors are doing because all the information exists in Notion and it's super clear.

And then once an assistant will take the first stab at analyzing that information and putting it into short comms, I'll edit it, and then I'll send a monthly update so people can kind of be pinged about what information they might need to know.

We built our entire social media calendar and execution in-house. And to do that, we essentially have an elaborate Notion system that we use with really clear tags, and that system is used by over 15 people, from our external copywriters, to asset designers, to contractors, to editorial on our team, to multimedia, to the folks who are scheduling and getting executive assistants or figuring out how to automate parts from the end to end.

Doing that from the beginning and saying, what parts can I automate? If I'm the person who was posting on social media, which I was for a couple of months, I get the notification on my phone from our scheduling app, and all I have to do is post it because all of those checkpoints have been really dialed in and systematized through reporting and clear process documentation.

Notion and Loom have been essential tools for me to learn, especially coming from a consulting background where I lived in Docs and PowerPoint.
I still send short Loom videos at the end of each day with a few folks, especially when we're working really closely on projects with short timelines, explaining what I accomplished, sharing my outstanding questions, and showing progress. People can comment on the video and give input. It’s just a much faster way of collaborating.

One of the things that you cover in the post is how you've revamped the OKRs process at Levels. What was wrong with the previous OKR process, and how did you approach improving it?

I don't think I ever talked to someone where I talked about OKRs where the answer was like, “Oh, yes, I love it.” I think we're moving towards a direction where hopefully that is not people's kneejerk reaction when they hear about OKRs.

So at Levels, we were really looking to make OKRs simple and relevant to use. We wanted to help our teams and our leads focus without it turning into a tracking exercise, which I think is the pitfall that can often happen with OKRs. OKRs are especially challenging for startups, especially for our current company in size. We’re Series A, 60 people, and still pre-product market fit. So we're really still scrappy and doing a lot of experimentation, moving really quickly and iterating a ton on our product and our growth.

So we needed to try to balance this need for organizational structure with these like rapid iterative cycles and quick decision-making as inherent in a pre-product market fit company. So we asked every function to draft their top objectives, including key results that were as measurable or trackable as they possibly could be.

We set up Google Sheets, but instead of measuring KRs specifically, we just asked them to state if it was on track, a little off track, or at risk. And again, we included EAs and as much automation as we could into the mix. It would take people like 1-2 minutes a week to essentially gut check and respond.

If things were a little off track or at risk, we asked how the rest of the company or other team members could help. We repeated this mantra in our weekly Friday forums that every person should know how their work drives functional and company OKRs. And if it's, if you're unsure, please ask. And this aspect was also very helpful for our team because it allowed us to have this more directed, focused way of thinking about company and functional objectives.

We still have room for improvement, though. We don't quite have enough organizational stability to fully translate our OKRs into company outcomes quite yet. And that's for two reasons. One, our functional priorities are changing because we're rapidly iterating on a weekly basis.

And so the OKRs can become quickly out of date. Then you need a process for updating the OKRs and then it. It can become a sort of death by process. And then we sort of felt the OKR process, at least the tracker we had, was at risk of becoming kind of descriptive versus truly guiding decisions.
Instead, we're pivoting to establish a small number of critical objectives still, but instead of KRs, we're using steering metrics. So what are the steering metrics that can help guide and make decisions on how we are reaching those objectives? And hopefully, the steering metrics still facilitate the same focus and prioritization and alignment towards the objectives without creating details that quickly become out-of-date.

We read Aaron Digman's Brave New Work, and this book was one of the driving forces that led to us shifting from OKRs to steering metrics. I think the steering metrics so far are already a bit more helpful, just providing even more visibility into where we have a pulse on the business and using that pulse to make more informed decisions.

Do you have an example of a steering metric that is a bit less defined than a typical KR?

One of our goals is to lower CAC. So instead of having a specific target, it's more like, directionally, where are we trying to steer the ship towards? And if we're going in that direction, we're gonna say that we're doing a good job versus setting a goal that we wish our CAC was $20.

What sets apart a good strategic memo from a bad one?

At Levels, we are all about memo writing. It's definitely how strategy happens and how decisions happen. Sam, our CEO, does a deep dive into how we think about written communications and memos. I think a good memo builds a high-trust culture of decision-making.

So what makes a good memo, then? The structure that we will try to follow is of course, having some initial context, although it's easy to suffer from too much context and have context collapse, especially if there are a lot of memos being written.

So every single memo at Levels has a TL;DR section and generally a Loom or some sort of summary where if you are not on the Product team, you don't need to read every single line of the memo. You could watch the Loom instead and get high-level points enough for whatever function it is that you're working in.

A good memo also steelmans the argument generally. We're writing memos, and we're trying to decide if we are going to pursue a path or not pursue a path, and then how to pursue the path. And some of the best memos we've written have been when we say we're gonna pursue a path, and then we steelman the argument, and there are all these reasons why we should not pursue the path.

And then the end of the decision is actually, hold on, let's not do this now. Now that we've laid out all these really great arguments that just steelman our original one. So definitely include a steelman argument.

You have to include a number of examples too. A good memo should be accessible. It's not a chance to show people how smart you are. The best leaders are ones who share information and make it accessible as if you are a third grader.

And then at the end of all of our memos, obviously include references and give a place for the audience to provide written feedback. People will jot down their thoughts and share feedback, and then we can hop on a call as needed. Generally, after any big memo, we'll do an AMA, so the author of that memo will host an hour-long session, and the whole company can come and share some thoughts and feedback and kind of close out as we move forward on that decision.

It sometimes sounds like a very long way of making decisions when a company is moving so quickly, but having everything documented and really going through the thought exercises on a deep level has helped us make some good decisions that have gotten us where we are now.

So I now really also enjoy memo writing. I started off creating PowerPoints in consulting, and they’re very similar in structure. You're telling a story, it just isn't a written format, and in our case, it's a Notion doc. It’s the same skill set. I think if you know how to story tell or provide arcs, you have a clear narrative.

Where can people get in touch with you?

You can find my original blog post here. Feel free to email me at sonja@levelshealth.com. Otherwise, check out levelshealth.com and our blog if you want to learn more about metabolic health and the metabolic health crisis.