Clara Ma, Founder and CEO of Ask a Chief of Staff
Clara Ma, Founder and CEO of Ask a Chief of Staff
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Tyler Sellhorn: Hello, everyone. My name is Tyler Sellhorn, and welcome to another episode of Speak Easy, the podcast where we discuss communication, productivity systems, capturing our thoughts, and how we share those thoughts with our future selves and others. We believe that managing our brains is core to 21st century work, and we're here to learn how to do it better than we did yesterday. Thanks so much for listening. Speak Easy is brought to you by Cleft, the easiest way to collect your thoughts. With our cross platform applications, you can simply capture your ideas wherever you are and paste them where they belong later. Today, we are blessed to be learning out loud with Clara Ma. Clara is the founder and CEO of Ask a Chief of Staff. Clara served as Chief of Staff at Hugging Face during their rise to unicorn status. While Clara was there, they discovered two things. How transformative the Chief of Staff role can be for both executives and their [00:01:00] organizations, and how challenging it is to create the perfect match between Chiefs of Staff and CEOs. That's why Clara founded Ask a Chief of Staff. Ask a Chief of Staff is now the leading platform connecting high profile executives with exceptional Chiefs of Staff, drawing from their elite community of over 400 members worldwide. Clara, thanks for allowing us to capture your thoughts today. We're curious to learn from you and your experience and the experience of the Ask a Chief of Staff community members. Please tell us, how do we stay in lockstep with our closest collaborators? How do Chiefs of Staff stay in contact with their principals? How can we build communication cadences like the best CEOs and Chiefs of Staff do? How do we build the communication cadences that serve us and our professional relationships well?
Clara Ma: Perfect. Well, thank you so much. I'm so glad that we're talking about this question today because I think that communication between a chief of staff and their principal is first and foremost, the most important thing that you can do to establish a great relationship. Between [00:02:00] these two partners, communication is key when it comes to talking about what priorities are about what you need to be looking forward to in the next week, month, quarter, and most importantly, it's such a crucial aspect of building trust.
Between a principal and chief of staff. So I know you touched on a couple of different questions. I want to try to answer as many of them as I can throughout this conversation. But when it comes to communication, consistency is key. And I know as a fellow content creator, you probably have heard this a million times, right?
Consistency is key. You have to do it often. You have to practice the skillset. And it's the same thing when it comes to communication between two people, you can't just. Have a conversation and say, okay, great. We're communicating with each other. Like, let's just do this for the rest of our time together.
Really. It's about having a conversation dissecting what made it a great conversation and what made it not so great conversation, and then practicing the things that make it great over and over again.[00:03:00]
Tyler Sellhorn: Okay. I want to pull apart so many different things there. Before our conversation, we talked about cadences and how those are a primary component of having a great relationship between a chief of staff and their principal or just any relationship, right?
It's like how often do we meet? And you pulled out these weekly, monthly, and quarterly timeframes. And I guess maybe what makes some topics or some conversations more important to be weekly and which ones need to be monthly and which ones need to be quarterly? How do we break apart like which things happen when and how often? Yeah, maybe
Clara Ma: Yeah, this is a great question. And honestly, it's one that will change over time. I can't say this is what it is, and this is going to be it forever. Again, we want to practice communicating and practice
Tyler Sellhorn: we
Clara Ma: out what is the right thing to talk about.
Tyler Sellhorn: that's
Clara Ma: on a kind of macro level, let's call it.
Tyler Sellhorn: or
Clara Ma: weekly basis, you should be sitting down with your principal to discuss top level [00:04:00] priorities, right?
You need to be able to set the direction of what it is that we're going to be working on at this week. And those priorities may change as you hit Wednesday or Thursday, right? And you're running out of time, or maybe some things are taking longer than you expected. But I like to say every Monday, you should be having a sit down with your principal to say, okay, here are my priorities.
Let's gut check. Are those the right priorities? And then what are your priorities as a staff member? CEO or principal of this company, and how can I make sure that you are going to stay on track to create those things and make sure that you're working on the things that are most important for the company, then I would like to do a kind of a smaller stand up.
This doesn't have to be as formal as a sit down. It doesn't have to be so agenda heavy, but having a little block of time every day. Where you're able to check in with each other. Just make sure if you have any questions, you can get them answered quickly. Or if your principal has a new priority or anything else that pops up, you're made aware of that.
I think those are really important as well. So maybe I can give a couple of examples of [00:05:00] chiefs of staff and principals that I think do this really well. One pairing I know, they actually work fully remotely. One of them is in New York, the Chief of Staff, and the CEO is actually in San Francisco. So obviously they're working with a pretty big time difference, but they make it work really well by having a standing biking meeting.
So what I mean by that is that, The chief of staff gets up a little bit earlier, right? Naturally they're on EST and they are kind of going through inboxes, making sure that they're checking off of anything that they can kind of get prepped for their principle for the day. So after they've collated all that information.
The principal who's getting up a little bit later has actually a bike commute into the office in San Francisco. And during that time, that's when they'll pick up the phone, call their chief of staff and say, okay, give me a rundown of everything that you've collected, tell me what's top of mind, and then let's do a gut check on priorities really quick.
So that helps really set the cadence for what they're going to be working on during the day. So that'll happen on a Monday. Then every weekday after that, they will have that [00:06:00] same Biking meeting check in to make sure that things are on track and things are moving forward at the pace that they are.
And again, because they're getting new information every day at the end of day at the beginning of day, that's a really great place where they can check in with each other and make sure that they're still working on the same operating cadence. So that's one example I really love.
Tyler Sellhorn: Uh, doubling up what it is that you're doing, with those walk and talks or those bike and talks as they are
I'm also thinking of okay, so I support some people that are in E. S. T. I wonder if I can get them a London or Africa or European based chief of staff to help them set their priorities.
You're just thinking about that time zone difference of letting somebody else start sooner, right? I think that's interesting.
Clara Ma: yeah, I really love that idea. And as a chief of staff, right, your day is naturally filled with a lot of meetings, a lot of checkpoints with different teams. And so I actually think there is sort of an advantage to being [00:07:00] a couple hours ahead of your principal because you have a little bit more of that downtime, if you will, in the morning to get your day in order, get focused and things like that.
So maybe a bit of a hack for anybody who is looking to start their day with an agenda. I'll even give my give myself as an example. My EA is also based in the Philippines. So she has many hours ahead of me. And I think the magic of us working together is that I wake up and there's already a bunch of stuff done.
And then when I'm logged on a little later in the day, I'm able to kind of collate, synthesize my thoughts for her. So that when I'm asleep, she's reviewing those things and then she's kind of getting the day started. So I think there's an interesting kind of time hack that you can do with the different time zones if your team is located in different places.
Tyler Sellhorn: You know, podcast, huge fan of distributed working styles. I used to host the remote show for WeWorkRemotely. And yeah, it turns out that the sun doesn't shine on every time zone at the same time. It [00:08:00] like goes around all the time. So it's really interesting to see you and teams that you're supporting really like allowing the work to follow the sun and to be able to like have those handoffs be effective for people that are closer, like that New York to SF kind of a split, or even, 12 hour splits like EST to PHT, right. You know, the Philippines is as hard as it gets in terms of times on splits. Yeah, shout out to the teams that are able to like, say, you know what? It's the results, it's the work and it mostly is inside of a screen for us. So where you are is less important than just being able to work well together, even though it's, across distance.
Clara Ma: Absolutely.
Tyler Sellhorn: Okay you talked about that weekly and daily thing. How do we get into that monthly quarterly space?
Like what? What does that look like? Which things go in a weekly or that daily stand up piece or versus something that belongs in a monthly or quarterly cadence?
Clara Ma: Yeah. So I would say that the daily stuff is the [00:09:00] most urgent, right? What are things that need to get done immediately? Then as you zoom out on your monthly or your quarterly, those are your longer term projects or your longer initiatives. So I would say on a monthly cadence, you want to be giving a pretty You want to be giving a pretty detailed update on the overall health of the company.
So this might be like an OKR check-in, right? Making sure that the KPIs that you set at the beginning of the quarter are being met, maybe doing a red, yellow, green, right? Are things on track, things not on track. And those are good checkpoints for your then quarterly cadences of strategic planning, of figuring out what comes the next quarter.
So when it comes to the chief of staff and principal dynamic when it comes to the chief of staff and principal dynamics, specifically from that monthly cadence, you really want to do an overhaul gut check of how the company is moving. Maybe this includes prepping for an all hands or maybe a town hall, right?
Or getting department wide updates from your marketing team, your sales team, making sure that everybody is on a good kind of like [00:10:00] green health, if you will. Um, and that's where those kinds of priorities will come in. On a quarterly basis. Of course, you're doing retrospectives on the previous quarter.
You're doing planning ahead for the next one. And then for this particular dynamic, I really recommend doing a career check in as well. I think a quarterly basis is really great for chiefs of staff and principals looking to figure out, okay, where is this relationship going? And is there opportunity to expand the scope or maybe even narrow the scope if there's too many things going on, um, for chiefs of staff in particular, I think that the career journey can be quite windy and maybe you don't know exactly where you want to go, but it's a great place for you to get.
feedback from your principal I actually recommend instead of trying to do an annual performance review between principal and chief of staff, you do a quarterly one because things are changing so quickly that it actually makes more sense to do it on a more frequent schedule so that you can continue to work on the things that are going to best serve your own career as well as [00:11:00] the principal that you're working with.
Tyler Sellhorn: that cadence conversation in that space for chiefs of staff, like you've been a chief of staff. You're supporting chiefs of staff How do you and how to your community members? How do they capture their thoughts as they get ready for that weekly meeting or that daily standup? How do they gather their ideas and get it written down in a way that is going to be most useful to honor one another's time, saying that we're going to have this meeting this often, right?
How do we maximize or improve or like really, optimize that time for its effectiveness together? You
Clara Ma: this is a great question as well. And I think ultimately comes down to each of your reading preferences. How do you like to absorb information? Right? So there are some principal and chief of staff pairings that I know love a pre read. And so what they're doing [00:12:00] throughout the week is they're either voice note dumping or they're uploading transcripts of video conferences or even notes into some sort of AI tool.
AI is really great for this nowadays. I know that cleft is a great tool that you like to use.
Tyler Sellhorn: magic words, voice notes, AI,
Clara Ma: Yep.
Tyler Sellhorn: right? Here we are, the Speakeasy podcast brought to you by Cleft. So yes, of course, yes, we love to hear you saying those things, of
Clara Ma: Yeah, absolutely. And there's a ton of other AI note takers out there. So feel free to use the one that your company enjoys using the most. And then using that to synthesize, right? Everything that has been talked about pulling out the key action items. I'll, plug one and you feel free to use this as you will, but I'm a big fan of using the tool ambient where they actually can track.
So let's say you're having a recurring meeting with your principal. They'll actually track those same meetings that you're having on a weekly basis, daily basis, and conglomerate them. That's not the word I'm looking for. Consolidate them into one big [00:13:00] project so that it can start to see trends and patterns over time as well.
So you can say, okay, we've been talking about, trying to break into this market for three months now. Should we actually take action on doing it as opposed to keep kicking it to the back burner, whatever that might be, so really use technology. I think that is a key thing that many of us can do now.
You know, I would say five years ago. AI technology was not where it was. There was still a lot of, I had to figure out and synthesize a lot of these notes, but use technology to summarize those things for you. And then using that. If it's a pre read that your principal likes or maybe a voice memo that they like, however you can best deliver it to them in a way that they are actually going to take the time to listen, to read and get the information that they need so that when you are meeting live, you can actually take action, make decisions and talk about strategies as opposed to recapping, whatever it is that you had already talked about before.
Tyler Sellhorn: I think that's awesome to hear you [00:14:00] referencing the kinds of tools and procedures and just like tactical Hey, try this version of things to be able to that. I'm a huge fan of a pre read and having it written down often we can just skip the meeting, right? So oftentimes when we have just taken the time to like voice our thoughts, right?
And have them written down, right? I love a voice draft and I love the opportunity to mature that into something that is You know, very readable, very, and using the AI tools to support you in that. I guess maybe the other thing that I want to ask what other kinds of productivity systems do you see yourself using in collaboration with others or, chiefs of staff that have been sharing back, Hey, I did this version and it worked really great for this. What are some of those things that you've seen be really effective with, your chiefs of staff and their principals?
Clara Ma: So I have a couple of tools that I love using. I'm a big Notion user. I think Notion is such a [00:15:00] great hub for keeping everything together. It's a great hub for wikis, for playbooks, things that you discuss often. And I know Notion also has AI features now where they can help summarize meetings and create agendas.
So
Tyler Sellhorn: mm-hmm
Clara Ma: documentation Software you like to use. I want, I would say pick one and stick with it. Make sure everybody is on it. You know, it's organizational wide, not some people using Google Docs, some people using notion, other people using coda. I think that truly is the death of productivity and efficiency is like everybody on a different tool where you have to learn different things.
So. Pick one. And I think as a chief of staff, you are that kind of change management person who can introduce a technology into your company and make sure everybody's on it. Another great tool that I like to use is honestly pen and paper. I think that there is something about having a very tactile.
Yes, you have one exactly in front of you.
Tyler Sellhorn: for the audio listeners the fleeting thoughts that I'm having as I'm listening to Clara, like I'm [00:16:00] capturing those, with pen and paper myself. So hard agree with being lofi analog as well as, digital enabled.
Clara Ma: Yep, exactly. Just having something that's tactile, right? As you write it down, there have been studies that show when you write something down, you are more likely to remember it. And also it's a very, it's a, it's one of the few times I think that we have in our work days nowadays where you can't be distracted.
When you're writing on a piece of paper, you are using your eyes, you are using touch, you are using your senses to really Understand what it is that you are writing down and you can't get a notification pop up right on that piece of paper. So I think that having something like that is so important as well.
And I had one more that I wanted to share that I'm completely blanking on. So give me a second to
Tyler Sellhorn: sure. You're good.
Clara Ma: Turn it back out. Productivity tools.
Oh, okay. Then the last piece that I [00:17:00] will share is calendar management and time blocking. I think that in today's world, like I mentioned, we get slack notifications. We get text messages. We get pop ups in our computer screen telling us when our next meeting is. And. All of that context switching can really lead to poor communication.
It's interrupting your flow of thought, it's interrupting whatever it is that you're doing, and so blocking your calendar so that you have time to, let's say, create that Agenda for your next meeting or having time to go through your email inbox, right? Making sure that you have chunks of time to spend on deep work on prepping all of that kind of stuff I think that is a huge productivity hack that has helped me throughout my life And is actually a great piece of feedback that my ceo gave me when I was a chief of staff was to Make sure that you're giving time to time right making sure you're blocking off your calendar for you know Deep thought and just giving yourself this time for your brain to process the things [00:18:00] that you have thought about or talked about process what's coming up ahead and give your brain the time to make those connections between all of the different things that you've already done.
Tyler Sellhorn: You just for myself, right? I'm reflecting. I use time blocking. And when you said the magic words of, taking the time to reflect into to, think about and process, maybe this is not a secret to the listener. But I like to talk. I'm a podcaster. Obviously, cleft naturally fits in with me and my preferred modes of thinking.
I don't think I've spent, I don't think I've blocked time yet for just thinking aloud. I've done things like taking walks with Cleft and getting my thoughts out that way, but I don't know that I've, that's always been like an ad hoc I just need to do this right now rather than putting a time block to it.
But I think I'm going to take that one away. I guess maybe that's the other thing that I'm hearing you say with, using the pen and paper thinking about the change [00:19:00] management associated with which tools and which I, which things are, we're going to be choosing as a group. I wonder if you, how you think about like location changing, right? So you're a chief of staff, you, let's use our example of that New York based person that is assisting. Somebody in Pacific time, and I guess maybe I'm wondering, how do we manage, how do we deal with moving spaces for ourselves to do different things, right?
Because I I, we're on the phone for that biking meeting, right? But then there's other times when we're at, on a video conference. There's other times when we're with our pen and paper. I guess I'm wondering are there ways that we can build routines that assist our brains in that way? What have you seen be effective in terms of setting up that calendar, doing that time blocking? What things go where in our calendar? And how do we do that also with associated with locations? You think about that in calendaring and [00:20:00] stuff too? What are you seeing be effective in those ways?
Clara Ma: Yeah, I think location is a very important part of your work day, and I know many of us work from home, maybe some of us go into a co working space, maybe some of us have an office, and I think it's really important to figure out which of those spaces is most conducive to what kinds of thinking. So one really great co working space I love is Industrious, and they have been very intentional about having meeting spaces, the lighting in meeting spaces, in their phone booths.
In common areas, because different locations and environments will help you be more creative or maybe more focused. So for me, I work mostly from home. So I think it's really important for me to have a specific desk set up that I know this is my workspace versus, I really try not to work from bed as much as I love doing it, but I know that.
If I do that, my bed brain will creep in and say, okay you're in your place of rest. So we're going to start shutting down some of the deeper thinking [00:21:00] thoughts, if you will. And that is not going to help me if I need to put together a strategy doc versus then conversely, it also messes up when I try to go to bed.
And then my bed brain is last time you were here in this location, you were trying to do deep work. So now you're going to start spiraling and thinking about that. So having setups that are helpful for whatever mode you need to be in I think is very important. I mean, there's even studies that show that if you are going to take a test, you want to go and practice in the space that you're going to take the test, because it's going to help with your recall the best.
So, You know, take that study into mind as you are setting up your spaces. If you work from home, right. And you're like, I only have this one desk space, figure out if you can try to change up some of the environment. So you mentioned taking a walk with cleft, right? So maybe during your deep thinking time, it is an outside or an outdoor activity, or, you're going to the gym and you're walking on the treadmill, whatever that might be.
And I am a big proponent of setting up meetings that are. Phone call meetings as opposed to sitting on zoom all day long, right? [00:22:00] Yes, it's important to talk to people, see them and have and see their body language, but at the same time, if you can make it a phone call meeting and you're both walking outside, can change up your thought process a little bit and your brain processes so that you can be a little bit more creative, maybe you're getting a, Change of scenery, something else can inspire you and help you not be distracted, right?
By the clutter that might be around your house or, the next load of laundry you have to do. Just get out of that space
Tyler Sellhorn: of
Clara Ma: so that you can have a different kind of focus on the conversations that you're having.
Tyler Sellhorn: That makes a lot of sense. I guess I'm wanting us to, I'm inviting you to conclude here with this kind of before, during and after kind of like comparison. I know that you are somebody that works on continuous improvement, like that's even a thing that you've done inside of organizations is You brought up OKRs and KPIs and like thinking about how to move the numbers in the direction that we want them to move. It's fun to hear you with other guests. Shout out to Sarah and her [00:23:00] OKR verbal processing that we talked about earlier on the podcast. I guess maybe I'm curious to hear you talk about what has it been like for you before when you think about communication and what is it like for you right now and then what is it you think maybe is an opportunity for you to grow in the future? Give us that kind of like before, during and after sort of breakdown.
Clara Ma: Sure thing. So before I would say I thought conversation and communication would happen naturally. I just thought, Hey, look, like we're all people. We know how to talk to each other. If I just say what's on my mind, it will turn into a great outcome. And I made it very ad hoc. I would say like my meetings were not great because they were not outcome for they were not outcome oriented.
It was very much let's hop on the call and see what happens. And when you do that. You will get a very honest depiction of maybe what that person is thinking, but you won't get a very focused depiction of what is happening. So I really realized that coming into a meeting, it doesn't have to be a heavy agenda, but it needs to be an outcome [00:24:00] oriented meeting where you have some sort of decision or something that you want to get out of this meeting.
And that's the best reason to have a meeting. If you're doing a status update as a meeting,
Tyler Sellhorn: a meeting.
Clara Ma: why are you doing the status update, right? What are you ultimately trying to accomplish? It's not just telling people
Tyler Sellhorn: would
Clara Ma: This is good. This is bad, but
Tyler Sellhorn: focus on
Clara Ma: it's to make a decision on something or drive something forward.
So I would say my before
Tyler Sellhorn: and
Clara Ma: very loosey goosey, very
Tyler Sellhorn: is
Clara Ma: kind of see what happens. And I would say, you know, learned a lot from that, um,
Tyler Sellhorn: is
Clara Ma: in my career.
Tyler Sellhorn: hop on Slack
Clara Ma: Nowadays, I really try to focus on having a little bit of buffer time in between meetings, whether that's starting every minute or starting every meeting five minutes after the hour so that I have that built in buffer time or.
Going with the 20 minute, 25 minute meeting as opposed to the 30 minute meeting, 50 minute meetings instead of one hour. And I find that gives me enough time to really kind of process what happened prior in the previous meeting and then go into the new one again, trying to really figure out what that outcome is.
And ideally I [00:25:00] have the outcome of the meeting, ahead of time before I even step into the day. So I think that's one way to really improve communication is to make it very clear why we are discussing something. One more thing I will say is that prior I would hop on Slack and ask someone, Hey, can we talk?
And that would stress everybody out, right? That's like, Oh my gosh, what do we want to talk about? Especially as I moved into a chief of staff role, you know, the, Power and authority that I had was much scarier than, you know, when we were peers working together.
Tyler Sellhorn: doing that,
Clara Ma: instead of doing that, I try to make it very clear that if I want to have a five minute phone call with somebody or call a kind of impromptu meeting, I make it very clear what it is that we're going to talk about.
Tyler Sellhorn: clear
Clara Ma: you have five minutes to discuss?
Tyler Sellhorn: talk about.
Clara Ma: This particular decision that we made so that we can move forward on this. You know, do you have five minutes to talk about why our agenda here is not aligned to whatever it is so that somebody is not feeling panicked about what it is that we're going to talk about
Tyler Sellhorn: I'm
Clara Ma: they can also prepare ahead of time so that we can make this meeting the most effective as [00:26:00] possible.
In the after state what I'm currently working on right now is leading into discomfort a little bit more. I think that as a chief of staff, you are leading a lot with soft power, right? You're influencing without authority, which means that you are constantly reading people and trying to make them feel as comfortable as possible to share their vulnerabilities, share their discomforts.
Now that I'm in a CEO position, I think that it's important to, Share those vulnerabilities of yourself and lean into the discomfort of sometimes saying,
Tyler Sellhorn: think?
Clara Ma: know, what do you think? And truly mean that, right? Not in a patronizing way, but
Tyler Sellhorn: but
Clara Ma: understanding where your limitations are and feeling okay with sitting in the discomfort of not knowing something or having a really difficult conversation.
More so now than ever, you know, I have to be able to give my teammates feedback that may not be comfortable, but I know ultimately is better for their development and for the company as a whole. But. Some of those conversations can be really uncomfortable to have. And so how can I [00:27:00] use language that is effective, but still comforting?
How can I make sure that what I'm trying to convey is not just completely sandwiched in between what I call the compliment sandwich, right? You were giving good feedback and then you're putting the negative feedback, but then you're ending it with good feedback, which in theory sounds good, but sometimes
Tyler Sellhorn: which in
Clara Ma: the kind of constructive criticism that you're trying to give.
So
Tyler Sellhorn: there.
Clara Ma: something that I'm working on. I'm hoping my communication there can be. better in the future. So that I can feel a little bit more comfortable with discomfort, which I know is kind of a bit of an ironic back and forth and a little bit of circular loop here. But I do think leaning into that is going to make me both a better leader and communicator.
Tyler Sellhorn: Well, I want to say thank you very much, Clara, for inviting us. Into the discomfort of becoming more intentional and more explicit with our requests and even just choosing to express things with a vulnerability that says this yet, and maybe you do, or we'll figure it out together. I [00:28:00] think that's so interesting to hear you reflecting and growing and continue to improve.
Just that's what we're trying to do here. We're trying to do it better than we did yesterday. And we just want to say thank you so much for speaking your mind and allowing us to. Collect your thoughts. And yeah, I'm definitely gonna be taking away some things here from this conversation.
Thanks, Clara.
Clara Ma: Absolutely. Thank you again for having me, Tyler.
