Office Hours: I'm the Chief of Staff at a YC startup and the former Communications Director for a congressional campaign. I'm Ali Rohde.Featured

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Thanks so much for joining us @alirohde!Elphas – please ask @alirohde your questions before Friday, December 4th. @alirohde may not have time to answer every questions, so emoji upvote your favorites 🔥👍🏾➕
MollieFleury's profile thumbnail
Hi Ali! Thanks so much for listing out all your efficiency resources!! For networking, how do you maximize the benefits and impact of the communities you're in? Do you have an organizational tools for managing your network and staying in contact with everyone you meet (like a personal CRM for example)? I've joined so many communities lately and feel overwhelmed trying to keep up with them. I've always been a pen-and-paper note taker, but am looking to switch to something that is searchable and more organized. Do you have thoughts on Notion vs. Evernote vs. Roam Research?
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Hey Mollie! Thanks for the great questions.Re: networking – I put down a few notes from calls I have with people 1:1 in a Roam doc so I don’t forget about them entirely. I also try to do a few things after the call, though I’m definitely not consistent on these: 1) Add them on LinkedIn or Twitter or Facebook (if it’s a more personal rather than professional connection) to increase the likelihood we interact again – for instance, I can see if they’ve published a new blog post, or if they’ve started a new job. 2) Send a follow up email or Slack message or DM after the call, thanking someone for taking the time, and ideally mentioning something from the conversation that stuck with me. 3) Following up on any commitments I made. Often in these conversations, I’ll offer to do something – eg send someone an article, or connect them with someone else in my network. It’s easy to forget about those commitments if you then go straight into your next meeting, but people really appreciate it if you actually follow up. If I think there’s a good chance I’ll forget about a commitment, or if it’s a more complicated ask that requires something on their part, I’ll ask that person to send me an email reminding me of my promise and providing any necessary details so that there is an actual artifact from the conversation that will help make sure I actually do the thing.Re: notes – I’ve liked Notion and Roam Research. Never tried Evernote. It seems to really come down to personal preference – what is the thing that you actually enjoy using, that you’re actually going to come back to consistently? You can have the most beautiful, structured Notion in the world. But if you keep on forgetting to use it, then it’s going to be a lot less useful than a lower-tech solution (like pen and paper) that you actually use consistently.Re: communities and feeling overwhelmed – I totally feel that. Sometimes thinking about all the opportunities I’m not taking advantage of can be really stressful. I think two things could be helpful here. 1) Just like with the note taking system, I’d pay attention to your personal preferences/what you do naturally, and then build a system around that. For instance, I hate long Slack threads. I’d much rather talk live about a topic. So I don’t even try to keep up to date with the latest thread going on in a community’s Slack channel. Instead, one time I posted that I was going for a walk around Dolores Park that Saturday afternoon, and asked if anyone happened to be around and would want to join me. Turns out, people really crave IRL social interaction during COVID. I ended up getting a good little group to hang out and chat socially distanced at the park, which helped me facilitate deeper bonds than I would have if I were just commenting on others Slack posts. 2) Try to set manageable goals. If you want to meet more people, then make it a goal to DM 2 people on Slack each week to see if they’d be up for a 1:1 Zoom call to get to know each other better. Or sign up and actually stick to those Donut matching systems most community Slack groups seem to have these days. Or make it a goal to post just once per week, or attend one event, or comment on just one of someone else’s posts. It can be really tempting to set really lofty goals (contribute to every conversation! Meet everyone in the channel! Quickly respond to each of the notification s you get!). But, in my experience, those lofty ambitions set you up for failure. And then you feel bad about the failure, and are less likely to try again, and it just turns into a self-perpetuating cycle. I’m all about small goals you can actually achieve, which then make you feel good when you actually achieve them, making you ever more likely to work to achieve your goals the next day.
MollieFleury's profile thumbnail
Really appreciate the detailed response!! Thank you! 😊
JRShraybman's profile thumbnail
awesome! congrats on everything, Ali and thanks for the great share.I've gone back and forth about whether to run for public office, but always feel so overwhelmed with the reality of the situation as a whole really. I don't have any specific questions - just a general shout out of kudos to you : )
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Jessica, thank you so much! I really appreciate that. I have a few friends who work at EMILY’s List, Run for Something, and other organizations that support women running or considering running for office. I’d be happy to share some resources if that’d be helpful. Respond here or DM me on LinkedIn if so!
JRShraybman's profile thumbnail
thank you! I sent a request on LinkedIn and would love to follow up on this. You can also reach me via email - jessica@shraybmanlaw.com.looking forward to it!
Charlie's profile thumbnail
Hi @alirohdeThank you for your time. I used to be a Chief of Staff about 3 years ago, and I am about to go back into that role in the new year. Are there any tips you have for that role to make it a success. Any planners you use to keep you on track?Thanks for the book reccomendations and tools; definitly going to check them out. I've also signed up for your newsletter :-)
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Charlie, congrats on the new role!!Seems like you've already been around the Chief of Staff block before, but here are some suggestions to consider:- The groups I mentioned above could be really good resources, especially the Chief of Staff group. If you're interested, once you start the new role, feel free to DM me on Twitter or LinkedIn and I can send in a referral to fast track your application.- In terms of planners, I do 3 things. First, I use Roam Research, which has a "Daily Note" feature that I love. Every day, if you open the "Daily Note" page, it immediately creates a new journal entry for that specific day and hides the previous day's entry. Every morning, I spend at least 10 minutes writing things in a few different categories that I rotate every so often. Right now, it's thoughts, contributions, and moments of joy. I think I came up with the latter two after reading Sheryl Sandberg's Option B. Doing this allows me to get my thoughts out of my head and onto the page before I start my day. Second, I have another page in Roam called "Meetings/calls," where I jot down a few notes for each meeting, so that I have something to refer back to when I inevitably forget that the meeting ever happened. Third, I use Asana for my to do list.- In terms of things that can make you the Chief of Staff role a success, I'd say the number one thing is to build trust between you and your CEO. You really want to be the person they can let their guard down around, and you want them to trust that they can throw you at a problem and you'll figure out at least the next step. One way I've found to do this is to ask my CEO about how she's feeling, and to lead by example by opening up about my own life. Obviously this differs by company/CEO, but I think the CoS-CEO relationship can be a really special and emotionally connected one, more so than most other roles (probably most similar to the relationships between co-founders). Another way I've found to do this is by paying attention to the things my CEO really doesn't like doing, and then handling them without her even having to ask. For instance, my CEO really wants to help everyone that contacts her, but she just doesn't have the time. So I'll often draft responses to people pinging her for help, sending them resources that could be useful rather than saying yes to a 1:1 30-minute call. Then all my CEO has to do is send the message, rather than to figure out whether she can fit someone into her schedule or how to say no to someone herself. I'll often look for these types of low-hanging fruit -- small things that I can do quickly and consistently, even if I'm working on a big project, that really make my CEO feel supported. I imagine other CEOs really might not like drafting investor updates, or doing a finance review each month. Find out what really feels like a burden to them, and then see if you can take it off their shoulders.
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@alirohde Thank you for such an in-depth response. I will certainly reach out via LinkedIn once I start my new role. I've also noted all of your wonderful advice.Thank you.
hi @alirohde! Would love to hear your opinion on who/what background would make a for a successful COS, as well as how you were chosen for the position. I'm currently interested in becoming a COS but haven't had much success yet in selling myself. Any advice you could share? Thanks!
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Hey Whitney, thanks for the questions!Re: backgrounds that make for a successful chief of staff. I think one of the beauties of the role is that there are a lot of different backgrounds that can make you successful. I've seen a lot of CoS come from consulting, which was helpful in terms of teaching them how to be thrown at a new problem/company/vertical and figure it out. Or I've seen CoS be former founders, which means they know what their CEO is going through. Or I've seen people come from VC, or finance, or marketing, or engineering, and so they understand businesses or startups from at least one lens already. And I came from politics, which I've actually seen in a few other chiefs, but it is a bit more rare.That diversity of background means that there isn't one thing you need to be a solid chief. It's a bit more about having grit, being trustworthy and genuine, being really excited and committed to the company/team, and then having a good story to explain why you belong there. See more about narratives in my response to @Nora below -- come up with a narrative that feels authentic and compelling, and be confident when you share that narrative with prospective employers. There's no one "track" to becoming a chief of staff, so there's room for you to create your own narrative and convince employers that your "track" makes sense.
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Hi! What skills and tools did you learn on the political campaign that you think transfer well to your current role? Any advice on shifting career/industry? Thanks!
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Hey Nora! For shifting careers, I've found that a huge part of it is your story -- the narrative you create around how your past experience positions you well for the new industry, better than perhaps those who have been in the industry the whole time. For me, my story was that political campaigns were basically like the fastest startups in the world -- you had to go from zero to one and build something from nothing, you had to raise a ton of money, you had to operate on a shoestring budget with a young team that was figuring it out as they went along, and you had to convince people to "buy" your product by voting for, endorsing, or donating to your candidate.Therefore, my story was that, even though I hadn't worked at a startup before, I was already battle-tested. I had already worked in an intense environment with a ton of ambiguity and in which I was responsible for doing things that I was objectively completely unqualified to do. I had already proven that I could do it.The other critical piece, at least for me, is you having confidence that you are qualified to move into the new industry, and then you showing that confidence to prospective employers. This is easier said than done. For me, the political campaign was so intense and required me to learn so much so fast that it actually gave me a ton of confidence that I could thrive in a startup environment. On the other hand, I had friends who had similar backgrounds, who chose to go to business school rather than trying to break right into startups straightaway. There was no difference in our experience. It was just a difference in attitude.
Nora's profile thumbnail
Thanks so much!
emilytsitrian's profile thumbnail
Would love to know a "day in the life" for a Chief of Staff at a startup! I've never quite understood what the role entails.
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Emily, thanks for the question!That's a tough one, since the Chief of Staff role varies dramatically by company, though there are patterns. For example, I've consistently seen differences between Chiefs of Staff at early-stage startups, and Chiefs at bigger/later-stage startups. At the early-stage, you're in "implementation" mode. You're in the weeds, doing whatever needs to be done, helping the company go from 0 to 1. For instance, for me, as soon as I joined, I started owning our P&L, leading hiring, and doing our marketing/external communications. We didn't have a finance team, a people team, or a marketing/comms team, so I was filling the gaps. At the later stage, however, you typically have those functions built out, so the Chief of Staff role is more high-level, more strategic, more about going from 1 to 100, aligning teams, strategic planning, and generally making the organization be more effective.Across the board, though, I'd say the Chief of Staff is being the right hand person to the CEO (or whichever executive you're the Chief to) and helping them get more leverage on their time. It almost always involves unglamorous, administrative work, and you likely don't have a team to lead and you may be jumping around from project to project. But, in return, you get an incredible 360 degree view of the business and how it all actually works.Few more resources here, if you're interested! https://www.chiefofstaff.network/blog
emilytsitrian's profile thumbnail
Thank you!
sarrahrose's profile thumbnail
Hi Ali! Thanks for sharing, it's really inspiring hearing about other women's journeys (-: A couple questions: 1. Did you find the transition into the tech world difficult, and if so, what challenges did you face & how did you manage to overcome them? And what do you think were the biggest factors in having a "successful" transition? 2. What do you think helped you build your network so quickly? Any specific advice on cold-emailing / dming people? 3. Based on earlier answers, it seems like you were thrust into a ton of different roles & had to be super flexible with fixing whatever problems had to be solved. How did you learn / adapt as quickly as you did? Any best practices? Thank you!!
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Sarrah, thanks for the questions! Let me tackle them one at a time.Re: difficulties transitioning into tech, there were many! I think the main thing was getting to a place where I felt like I “got it.” Like I understood how startups worked. I remember, early on, I was put in charge of hiring a Customer Success Manager (CSM). And I just did not understand what someone in that role actually did, which made me feel awkward and unqualified during interviews with candidates. For me, 2 things helped here. 1) Talking to people who had more experience in startups than I did, and asking them questions (ie exactly what you’re doing right now!). I’ll often post in the Slack communities I’m in a question like, “what is the easiest way to produce a podcast if I don’t have a Mac?” Chances are someone there has some insight. 2) Perhaps more importantly, realizing (and then forgetting, and realizing again) that most people, especially in startups or VC, don’t really know what they’re doing. Most people are just figuring it out as they go along, even if their Twitter makes it sound like they know everything about every startup, ever. Like my CEO, who has an engineering background. When she started the company, she had never done anything resembling sales before, and then all of the sudden she was responsible for building a sales process and bringing all this revenue in (in addition to many other things). She was successful not because she had some secret knowledge, or because she had years of experience under her belt. She just kept working at it over time, and eventually it started making sense.Re: building networks quickly/cold emailing. As I’m sure you know, it’s all about quality over quantity. If there are a few interesting people you could get slightly warm-ish intros to (eg people who are fellow members of the Elpha community), then start there, rather than sending 20 DMs completely cold. Or, if there is a company or space you are really excited about, then focus on that, and write a really personalized note to that person that shows you care and are paying attention (eg saw your tweet on XYZ, which made me wonder blah blah blah). Also – be super concise in your communication, acknowledge that the other person is busy, and have a clear (and hopefully not too imposing) ask. A friend of mine once reached out to a famous author he had never spoken to before, and asked if the author would consider being his mentor. Understandably, he did not receive a response. Oh and I try to go for “smaller fish” rather than people who are getting a million cold emails or DMs a day. For instance, if you’re really interested in learning more about a specific company, it can be a lot easier to get a response from a company employee (who likely doesn’t get many of those emails, and may be able to route you to the most effective person to talk to), rather than the CEO. Re: learning/adapting to a new environment, other people have always been my greatest resource. Ask to buy someone coffee in exchange for them allowing you to pick their brain. Ask people about their experiences, or if they’ve found any really useful resources, or if they know someone who could be useful for you to talk to about XYZ.Hope that helps!
sarrahrose's profile thumbnail
super super helpful, thanks for taking the time to write all this down (-: