answering your most frequent career-related questions
we compiled insights from 30+ experts who used to work at places like Airbnb, Figma, Notion, and more
We get questions every week from people in the next play community looking for help as they tackle important career-related questions. To get you the best possible answers, we brought in the most accomplished and insightful operators we know—people like Lenny Rachitsky, Claire Butler, Amir Shevat, Becky Sosnov, Ryan Hoover, Cristina Cordova, and 30+ others—for their answers to your most common questions.
This 10,000+ word essay is the compilation of their answers to questions like:
“How should I choose where to work?”
“I got an offer, what questions should I ask?”
“How can I get startups to notice my profile when I want to work there?”
“What advice do you have as I make the leap from startup operator to venture capitalist?”
“What tips do you have for identifying a great manager to work for?”
“How should I prepare for interviews?”
We hope that you find it useful. If you have any questions, please send us an email: hi@nextplay.so.
tactics to choose where to work
Choosing where to work is a multi-variable decision. You surely have several inputs: compensation, interest, impact, learning, balance, and others personal to you. Surely some of those inputs come into tension at times (i.e. you could join a company that promises more cash pay today but it’s in an industry you are not particularly interested in). And surely you’ll be forced to make choices with limited information.
The one thing you know for certain—and this is perhaps the only thing you can count on with complete confidence—is that every decision comes with tradeoffs. Choosing where to work is no exception. And so, when making these types of decisions, perhaps the single best thing you can do is ensure you’re thinking clearly and not being allured by misleading or even straight up false information (which happens a lot more than you may think!).
So in choosing where to work, the place perhaps to start…before looking elsewhere…is with yourself.
What do you want? What is important to you? And why is it important to you?
These sound obvious and simple but most people do not have solid answers to these questions.
Sitting with those questions, and perhaps all the adjacent ones, for more than one sitting (i.e. perhaps write down some answers, sleep on them, and then revisit them a few days later) can help you build a strong foundation.
Figure out what’s actually most important to you and really pressure test your responses. Be careful about being too religiously attached to any of your answers without clear logic behind them.
For instance, some people try to tell themselves they care a lot about a particular industry. They want to work, for example, in health tech or ed tech or ai. That may be true, but they also may care about other factors (like if the company is going to be successful or how much the role pays). Weighing those factors, seeing and making those tradeoffs — that’s where a lot of the work to be done is in terms of choosing where to work.
Another common example is company size. Some people get very attached to the idea of being on the founding team of a company. And so they race out of college to join a startup…and that startup…well it goes nowhere.
People say they want the "startup experience" and 100 is too large; trust me, a 100-person company (even a 500-person company) growing rapidly is still breaking at the seams and it feels like a startup. For people early in their career, I also recommend joining a company later than you think you should. Joining a generational company can set your career on a totally different trajectory. Joining as Employee 100 at Ramp or Notion or Airbnb will set you up much, much better than joining as "Head of ___" at a 20-person startup that doesn't go anywhere. - Rex Woodbury (Daybreak Ventures)
To put another way - it’s very good to have opinions and also very good to be open-minded, especially when it comes to something like your career where you directly get to experience the consequences of your decisions. “Strong beliefs, gently held.”
Once you have this core set of beliefs and hypotheses, then you can go out and collect external frameworks and best practices, and see how they mesh with your internal set of beliefs.
The opposite approach—simply doing what you read online ;)—may leave you floating in the wind. You may end up compromising what’s actually important to you and optimizing for things that do not really matter.
For example, a lot of people, especially younger people, tend to really care about signing a job that gives them an important-sounding title. They want to be a Director. Or a Head of. And so they choose companies based on the ones that will give them the most important-sounding titles.
Why? Well that’s perhaps a deeper question. Is it because they want a lot of responsibility and perhaps a title indicates that. Maybe. Or is it perhaps because they want to “set themselves up” for future roles and having a fancy-sounding title today will help them do that? Or perhaps, and calling out now that it may be some combination of the three, it’s because they want to “look good” in front of their friends and family.
Whatever the reason is, it’s doubtful to be a very great reason when compared to the cost of missing out on a great opportunity (simply because that great opportunity did not offer you a fancy sounding title in your offer letter).
Always optimize for the quality of the company vs. the title or the role. Once you get in the company, you can prove yourself and move to different functions. One of my friends joined Figma in a non-sexy, internal-facing role--she quickly proved herself and was moved to a quite important, company-critical role. Find any way you can to work at a generational company. — Rex Woodbury (Daybreak Ventures)
A lot of people tend to romanticize tech startups. They perhaps watch the Social Network and Shark Tank and think to themselves: “that should be me.” The cynic amongst us could roll their eyes at these mission-driven hustlers optimizing for impact and then pivoting their startup into some HR b2b SaaS solution. We are not cynics, though. We are pro-ambition, pro-experimentation, and pro-trying out new things. You never really know where things will go.
A piece of you, especially amongst the type A crowd, may want to try and turn the “company selection process” into a rigid formula. It may sound nice in theory, to have a fancy spreadsheet scoring different aspects, but this approach likely underestimates the role of chaos and the unpredictable nature of company-building. It’s so hard to predict precisely what will happen with your career. This is especially true in startup land. You’ll never know who you’re going to meet and where those opportunities will lead.
The second startup I joined, I wanted to deal with open source and work with the community on open source code. While the company was not a great success, that experience led me to a great job at Google. Now magically, I was able to move from Google to a rapidly growing startup called Slack very early, and when Slack went public, enjoyed that success. — Amir Shevat (Darkmode Ventures)
So if we’re saying it’s near-impossible or at least very very difficult to forecast precisely what’s going to happen to a company and to your career, what should you do?
Well, sometimes it’s just about taking the first step. Sometimes you just need some momentum.
If you have zero experience in tech sometimes you just need a place to start. When I was first looking for a job in tech I knew nothing about the industry. I had previously worked for retailer The Gap, where I realized I was not very good at or interested in fashion. I got an offer at a startup but I had no idea if it was going to succeed or not, but it had some reputable investors and the hiring manager seemed smart. I wanted to get my foot in the door so I just went for it. — Claire Butler (Senior Director Marketing, Figma)
Going for it can take many shapes. It often involves a combination of sending cold emails, doing new things, and making decisions under some degree of uncertainty. Going for it, whatever it ends up meaning to you, can be a way of minimizing your overall regret.
Another piece of minimizing regret is around collecting information, especially low-hanging information, so you can make an informed decision. Yes, it’s hard to predict the future. But also yes, there’s some information or signal you can collect today to help inform your decision making process. Inform is the key word here — no one piece of information will likely make your decision for you; you will always need to revisit your core personal priorities and weigh the tradeoffs. But bits of information can help you paint a clear picture.
One category of people who are in the business of gathering information are venture capitalists. VCs are “professional” startup investors—their job, not so dissimilar from your own when choosing where to work, is to underwrite startups (i.e. see if they are a good fit and likely to be successful). And they do this by collecting lots of information across often a wide portfolio of examples.
It always helps to build relationships with a few investors to learn their perspective on companies you're considering for a full time role - they will be able to give you a pulse on if they perceive the company to be doing well, and how they compare it to other startups in the market. — Lauryn Isford (Head of Product Growth, Notion)
Getting in front of investors, similar to getting in front of companies, is again some combination of sending emails and bringing energy and ideas to a conversation.
When I went looking to switch industries, the first thing I did was read TechCrunch every day. I followed who was raising, who their investors were. I figured out the “top” VCs. From there, I would go to those VC’s websites and look at their portfolio companies, and then check the career pages of those companies. I found stuff that wasn’t on Linkedin. — Claire Butler (Senior Director Marketing, Figma)
And so when you go and talk to professional startup investors—people who underwrite startups for a living—and you ask them about their decision making process, you very rarely see lots of math. You’ll be able to learn some important attributes like revenue benchmarks, runway figures, and other fundraising criteria. But you’ll also be able to pick up on general investor sentiment - how do investors (and this investor in particular) feel about the company? The founder? Etc. (Of course, beware of bias…if an investor has funded a particular company, they may give you a particular type of answer. Also note that investors are wrong all of the time—their opinion is not gospel).
Yes you should look at the math and forecasts and what not. But recognize that, similar to your career (and you can soon see how this is all related), nothing is a sure thing. Therefore paying attention to the more qualitative/vibe side of things, while it feels fluffy, is a big part of the job to be done. This is especially true for early stage companies. And so, while there’s perhaps some math and certainly more for later stage companies, a lot of the “decision making process” comes down to pattern matching: trying to see if the progress made by this particular company and these particular founders resembles other companies. This is where investors can be most helpful because they often have data across a wide array of companies. They are professional pattern matchers (but note that some of the best companies are outliers and therefore can be incompatible with some pattern matching algorithms).
While a bit circular of logic, one high signal indicator that a company is potentially onto something is if they have managed to recruit amazing people. You have probably only ever worked for a few companies in your life. You have met hundreds probably thousands of people. Even if you have not yet put it into written words (which you should totally do some day!), you probably have a pretty intuitive feel for the types of people you admire and the types of people you’d like to work with. Looking at future coworkers and really trying to understand them as people and if you see yourself learning from and working well with them can be a really valuable exercise.
Follow the talent. Always optimize for surrounding yourself with excellent people. Even if the company doesn't work out, those people will go on to great things and pull you along with them. - Rex Woodbury (Daybreak Ventures)
Of all the people who work at the company, perhaps the most influential (if you were to join) will be the founder and CEO.
I prefer founder-led companies, so I need to understand what drives the leader. My approach is very specifically tied to founder chemistry given the nature of my role being in Communications, and I vet most companies based on my first few minutes with the founder. If you can't meet them in person, watch one of their talks online to see how they handle themselves. — Becky Sosnov (Global Head of Comms, Notion)
We covered some rather simple ideas in this response, but there were quite a few of them and you still may be wondering “how the heck do I make this decision?”
Our recommendation is to take the above, take all the other inputs you have, and try to make a very straightforward list: the three things that matter most to you. Write them on a sticky note. And put that sticky note somewhere in your room, where you can revisit it every so often (and update it if needed).
Where are the smartest people I know working?
Are they growing quickly, and is user/customer retention high?
Do I truly care about the mission of the company?
These are the three things I would look at. — Lenny Rachitsky (Lenny’s Newsletter)
Eventually, if you want to fulfill what’s on that sticky note, you will need to take the leap. Not every aspect of the startup will be perfect.
The product can be in various stages (pre-launch), so I try not to judge harshly on this. For example, Stripe's first website (before hiring a designer) looked terrible, but that would be expected, given it wasn't in the DNA of the founders and they needed to hire for it. - Cristina Cordova (Linear)
You’ll just need to figure out what matters most.
questions to ask before joining a startup
“What are the questions or types of questions I should ask a startup before I join? How do I spot red flags?”
So much startup-focused career advice focuses on picking a winner: finding the startup that’ll exit for $1B+ and leave you with a life-changing pile of cash.
Only issue is, you probably can’t.
Picking a winner is difficult. Most startups fail. And even the best venture capital firms, powered by experienced partners and teams of analysts, only pick successful startups <20% of the time. To compensate, VCs diversify into dozens of investments.
You, the job-seeker, cannot mirror this approach. You can only work at one company at a time. And your odds of correctly identifying a winner are, as we have established, very low.
So how should you choose? How can you be sure you are making the right decision?
Instead of just trying to pick a winner—something even the best VCs cannot do most of the time—start by weeding out the losers.
Spotting a fake business is surprisingly straightforward. You can try to pay attention to these red flags.
Misaligned product-market fit:
One way to check if a company has product-market fit is to talk to customers. How do customers discuss their experience? Are they telling their friends about it in a positive way?
Problems sometimes arise when startups act like scaled companies (e.g. huge payroll budget, large offices, etc.) well before they have achieved PMF. This is because “pre-PMF,” all that really should matter for the company is identifying what PMF would look like. Smaller teams are often better for this process as it is easier to steer a smaller ship.
Startups can be hard to analyze because success generally follows the power law, where a very small percentage of companies create most of the value. These outliers tend to have unusual qualities—that is what makes them outliers. Beware of sheep in wolves’ clothing—the companies that talk a big game and have nothing to show for it.
Operators are just undiversified investors. So you need the ask the same types of questions an investor would and keep your bar high. In my view, quality of company matters more than title or initial scope or comp -- the latter 3 you have more agency on and can change more quickly. Understand the TAM, unit economics, and track record/strength of the team. — Sri Batchu, CMO @ The Realreal
Low velocity: Velocity is speed multiplied by direction. Is the startup increasing their velocity? Do they have clarity of direction?
All startups have problems—the question to ask yourself is whether or not the startup is making progress against the correct problems.
Are people on the team being productive? You can figure out who at the company is productive by asking them how they spend their time and what they get done. People tend to talk about what they are most proud of, and their answers can be revealing of their definitions of progress.
As a measure for velocity, you could also ask yourself: what has the company done in the past month? If I waited another month before joining, how much more would they get done?
Do people at the company—especially the CEO—know what progress looks like? Do people work backwards from a vision, or are things retroactively cobbled together?
If, in your interviews, you notice people shy away from sharing details, we suggest you get curious and ask lots of questions so you can see if people really have clarity or not. Do people really know what they are talking about? Do the details make sense? Are they being reactive or proactive with their answers?
It is very common for companies to get caught up in distractions. Ask people who work there how they spend their time. How closely do those activities tie to what you think is important? Things like press and fancy offices can be useful, but if that is all the company talks about, as opposed to their product and customers, something may be wrong with the priorities.
Beware of being distracted by shiny objects like high private market valuations that are often not indicative of true enterprise value being built.
Good people are leaving: Change is very common for growing startups. But is there a systemic issue with good people leaving the company?
Ask yourself: why are the good people leaving? Conversely, is the business not growing as quickly as it should be? Are people there afraid to make changes? Are the co-founders arguing often? Are there certain teams doing a lot of complaining? (Note that bad people leaving may actually be a sign of positive change).
You will likely find that the quality of the team to have an outsized impact on your experience working at a company.
If you are focused on the early stage, there's basically three things that matter (in order): a) people b) market c) product. Most people look at this in the inverse order. I'd spend a lot of time assessing if these are the right people you want to work with - are they the right people for this market - and are they building something truly important? — Nikunj Kothari, Investor at Khosla Ventures
Easy interviews: If you are going through the interview process and find yourself thinking: “this is weirdly easy,” this may be a red flag.
You can pay close attention to the interview process. Does it feel like they are asking reasonable questions? Are you having to try hard? Are you having to think hard? Or is it the sort of interview you could breeze through. The more thoughtful the assessment process, the more likely the company cares about the quality of the team they are building.
This is not to say that complicated google style programming interviews are necessarily thoughtful or effective. Look for indicators that just tell you these people are good at assessing people and care about the same things you care about. You could even ask them for their reasoning for asking particular types of questions and see how that traces back to the values you think are important.
You could also ask people on the team how they found the company (or perhaps the company found them). How has the interview process evolved? Is the founder/CEO in the loop on it or who makes the decisions? Why?
Investor sentiment: When talking to investors in the company, find out why they invested. Ask to read their investment memo.
How much do you believe in their reasoning? Or are investors seemingly just investing in the hype and not actually reasoning from first principles?
Investors sometimes come across as these all knowing stakeholders that are able to predict the future. But that’s not really true. In fact, as we mentioned earlier, they are wrong quite often. And when they are right, luck factors aside, it may be pretty straightforward. Sometimes investors say things like: “well the founder is amazing and that’s why we invested.” That’s a reasonable answer, but you should do your diligence and ask a simple follow up question: “well what makes them amazing.” Do not take lazy explanation as holy: “well this person previously worked at Stripe and Google.” Again, go a level deeper: “well what did they do at those companies?” Oftentimes, people invest (their money but also their time) based on status and signals. That’s okay, but it rarely communicates the actual competence of a person. One thing that does tend to be a better indicator is “proof of work” - understanding what people actually did and what they were actually responsible for, and then validating those things with as unbiased as possible of third parties to verify the work.
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Once you have audited the startup for these red flags, you can evaluate all the other criteria you have (e.g. compensation, culture, interests, etc.). You’ll probably want to be strategic about batching your questions so you’re not asking them quite so randomly. As you go through a process, consider collecting an overall summary of the questions you’d like to ask:
Top ones that come to mind.. Note that some might be googleable depending on the company. IF THEY ARE GOOGLEABLE DO NOT ASK THEM. The hiring manager will find that annoying. Do your research first.
Who are your investors, when did you last raise, when do you think you will raise next?
What is your product and what is the value proposition?
What is your runway?
Do you think you have product market fit? Why?
Who are some of your customers? Can I talk to one?
— Claire Butler, Senior Director of Marketing at Figma
There are so many, but the top ones for me would probably be the ones below:
To understand the trajectory of the business: Can you please tell me a bit about the company's revenue growth rate last year, how it compares to what the initial target was, and what the project is for next year?
To understand the risks of the business: If 12 months from now the business is not doing well, what do you think could be the cause?
To understand expectations from the role: If 6 months from now you think I've been wildly successful in this role, what exactly would that look like? Which KPIs would I have moved the needle on?
To understand the business need from the role: By hiring someone for this role, what problem are you looking to solve for the business, or what opportunity are you looking to take advantage of?
— David Apple, former Head of Customer Success at Notion
While it can be scary at times, you should not feel bad about asking questions. Companies do not win by fooling you to come work there (because then you will be unhappy and unproductive).
How to get startups to notice you
“I am trying to get in touch with a particular startup that seems really interesting (and I think I could be a good fit for the role). What tips do you have for getting in touch with them? Should I just apply on the general application or how else can I stand out?”
Most people apply to jobs by sending in their resume and potentially a cover letter. If you really want a particular job, then you probably want to try harder than the average person. Trying harder can manifest in many ways (some of which we’ll cover below) — but it most certainly involves more effort and creativity than the standard approach.
If you think about applying for a job as you would think about doing sales for a product (in the case of applying for a job - just imagine you are the product), you may end up with very different conclusions about what tactics you should be using to conduct your search. Strategies very common in sales, like analyzing a funnel and thinking about call to actions, are actually not that complicated; they just require some upfront intentionality that, when applied to job-seeking, can be very effective.
You should not just apply and wait. You should run a very targeted, very thorough sales process. I outline that whole sales process here. That video is 10 minutes of all the advice I would give to everyone looking for a great career in tech. — Tyler Hogge, investor at Pelion Ventures Partners
The bottleneck for a lot of people, especially when starting out, tends to be near the top of the funnel. For a bunch of reasons - they do not get a lot of opportunities sent their way and thus the only roles they apply for tend to be hyper-competitive filled with lots of candidates.
And so, if you are looking for ways to get in front of your dream roles, here’s a few things to consider. The actual specifics around how you implement any of these approaches do depend on your situation - your background, the context of the role and the company, etc. But you should be able to pull out at least a few insights from the below and apply them to your search.
Most people’s general advice for increasing a company’s awareness of you as a potential candidate is to get a warm introduction.
Warm intros are always best. Do you know anyone who knows the company? Try to get an introduction. — Lauryn Isford, Head of Product Growth, Notion
Note that not all warm introductions are created equal. Maybe it’s more of a spectrum we should be defining the warmth. Some may come in HOT - meaning your contact would have really amazing things to say about you. Some…less hot…maybe even cold (and you don’t even realize it). A good approach is to, before the introduction is made, actually try and ask the person what specifically they would say about you to the rest of the company.
When you ping the contact you know at the company, you can do more than simply asking them to put in a good word. Again it depends quite a bit on the nuances of your relationship with them so definitely do not try and jeopardize that - but you can really try to set up the introduction for success. Impress the person. Add value to them. Do something that reinforces your unique-ness and why you could be a good fit. Give them a blurb that summarizes it so it is really easy for them to pitch you to the rest of the company.
If you do not know anyone at the company, which is also very common, you can try to build relationships with current employees or investors.
I would try to connect with every relevant employee via Linkedin. Via Linkedin I would also see who I'm connected to who is also connected to the Founder and/our leaders on the team, and ask for an intro. I would also figure out who their investors are (blog post from the last raise, crunchbase, Linkedin, etc.) and see if I - or anyone in my network - is connected to their investors, and I'd ask for an intro. If all else fails, I would write a highly tailored cover letter and submit to the general application - and then I would message the relevant employees via Linkedin to let them know that I applied. — David Apple, former head of CS at Notion and Typeform
You can use tools like nymeria.io to find people’s email addresses (note that depending on the stage of the company it is often just worth trying to email: “first name of the target person @ the company’s domain” — that tends to work pretty well, especially for early stage companies.
Lots of people respond to cold emails and Linkedin messages, especially if you put craft and thoughtfulness into the message.
If you can, find a warm intro from someone who works at the company or an investor. Many more jobs come through LinkedIn messages than you'd expect—even cold messages. If you can't find a good warm introduction, send a thoughtful cold inbound. Put in the work. Send ideas or free work, something that demonstrates you have the skills and the hustle to do the job. This will already put you in the top 5% of applicants. I've found that sending thoughtful Looms can also be a good differentiator for getting someone's attention. — Rex Woodbury, investor at Daybreak
You can get creative in your outreach.
If you can't get a warm intro, I'd put some thoughts together on the company and how it can grow (or build something that can complement the product and share it with them!) and send it over to the team. Cold outreach is usually most effective on LinkedIn, but you'll need to bring that value upfront (vs just asking for someone's time). — Lauryn Isford, Head of Product Growth, Notion
Someone last week took out a Linkedin ad targeted only to me. I thought “ha that’s funny” but didn’t act on it. — Claire Butler, Senior Director Marketing, Figma
With cold outreach, a bit like running a sales process, you will probably have to try and experiment with lots of tactics to get the results you want. You can experiment with how you send emails, when you send them, etc. and refine your craft as you ramp up volume.
Going from operator to investor
