Startup skills for non-technical people (Part 1)

Practical advice for getting a job at a startup

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Here’s some blunt feedback: Not having studied computer science in college is not a good excuse for not being able to add value to a startup. While you may think it’d be much easier to get a job if you simply “knew how to code,” there’s SO MUCH you can be doing that would make you (basically) instantly hire-able to many of the best companies.

I put together a list of skills I’d focus on becoming great at if I were trying to get hired, along with some resources I would recommend exploring to level up quickly. This list should be particularly useful for “non-technical” people who are looking to work at fast-growing startups.

If you think I’m missing anything or if you have any questions, please send me an email hi@nextplay.so. Would love this resource to be as useful as possible!

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One quick note—it’s one thing to think you have a valuable skill. It’s another thing to demonstrate you have that skill such that a third party (e.g. a company looking to hire you) can understand your levels of competence. Some of the ideas below are about building skills, and others are about demonstrating to others the power of your skills. I think, especially when looking for a job, you really need to be able to do both. That’s a limitation of the hiring process at most startups, it doesn’t do a great job of just recognizing people’s skills and instead asks them to communicate them somehow. I’m saying this just to remind you that you need to do both! Just thinking you are good at something is not enough, you’ll need to communicate it somehow (ideally by showing!).

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#1 - Writing memos

While it’s now possible to generate lots of words in just a few clicks using some AI writing tools, clear writing is still very much in high demand. That’s because being able to clearly articulate a decision (or group of decisions) is essential to any business. That applies to marketing, operations, sales, product—really anything and everything that has to do with business. And that’s especially true and important in an age where there’s more “noise” than ever before.

Startups, even really small ones, make loads of decisions every single day. Decisions around what customers to serve, what products to build, who to hire, etc.

One thing that separates a great company from a mediocre one is consistently making correct decisions.

And writing memos can be a tool that increases your correctness.

Jeff Bezos credits Amazon’s embrace of “the six-page business memo” as one of the company’s most important cultural practices. The Collisons are known for instilling a writing culture at Stripe, where most all big decisions are thoroughly documented in business memos. There are plenty of anecdotes about writing at many great companies.

Why care about this? Writing has many benefits. For the author, it can be a tool for thinking. By re-hashing your beliefs over and over you can sharpen them and make them more precise. For the rest of the company, it can be a tool for collaboration. It can be hard to manage complex decisions in your head, putting them in writing makes it easier for people to participate in the analysis of the assumptions, inputs, and outputs.

One reason I mention being able to write a great business memo as a particularly useful skill to have is that, if you can actually do this well, you can start well before you’ve been given a job offer. In other words, you can write business memos about companies you do not even work for, which will make you a very attractive candidate.

Advice for generalists who want to join startups

Here’s a quick example.

Imagine you wanted to work at a hot startup. Serval for example is building AI agents for the IT space. They just raised a big round from Sequoia. There are probably lots of people applying to work there.

Here are things you could do before actually working at the company that could showcase your hire-ability:

• Write a memo that articulates how you see the IT software landscape today and where it is headed.

• Write a memo around who you think they should hire.

• Write a memo articulating a marketing campaign they could run and why it would work.

• Write a memo discussing if and how they should update their landing page.

These memos would be really great learning tools for yourself to gain clarity in their business and opportunity.

If you wanted to get hired, you could then send them these memos. You could also publish them publicly. You could also send them to their competitors, and say hey I would love to work on these types of problems. You could also send them to their investors. You could ask them if there are any portfolio companies that could benefit from this type of analysis. If they are truly great memos, I would bet on this strategy working out well.

So how can you get really good at this? Practice. Practice. Practice. The easiest way to do that is to just start writing. Here’s some advice about writing but in general, I would suggest you do the following:

• Start by optimizing for volume. Write lots of words. About lots of topics. Do not worry too much about structure or grammar or anything like that. Just write. Beware of self-censorship early on.

• There are many ways to write but I would get good at writing clearly. Clear writing does well in the business context. Less about fancy words. More about communicating complicated ideas clearly.

• You can familiarize yourself with specific writing structures. Here, for example, is Bezos’ 6-page memo format. There’s no best format that all companies use so I would not worry about memorizing something in particular.

• Read! Follow your curiosity, but you could explore what’s considered “great” business writing. Not self-promotional books but actually great business writing. Here are some example repositories of memos to read:

  • Howard Marks from Oaktree Capital

  • Berkshire Hathaway Shareholder Letters

  • Jeff Bezos Shareholder Letters

  • Collection of Business Memos

#2 - Asking questions

“Your scientists were so preoccupied with whether or not they could, they didn’t stop to think if they should” - Jurassic Park

The biggest problem in startups is figuring out what to do. This applies at very high-levels: “what type of company are we building?” and also at very low-levels: “what should the sales development team get done this week?”

Part of being good at figuring out what to do is being able to ask good questions. Good questions are more powerful than you may imagine. I think good question asking is a very underrated skill. And yes, I think it’s a learnable skill: something you can actively improve (yet so few people do!).

When posed with a problem, a lot of people jump right into the action. They want to “hustle” and solve it as quickly as possible. This bias towards action is sometimes correct. Meaning it sometimes leads to the best outcome.

But sometimes, and I would argue more often than you may imagine, starting with questions is actually the faster path towards doing something great.

There’s an essay I really like written by Shishir Mehrotra (the former founder of Coda and PM at Youtube) that I’ll try to briefly paraphrase below but I recommend you read the whole thing if you are interested in this topic. It’s called “Eigenquestions: The Art of Framing Problems.”

Framing often starts with asking the right question. In many cases, a decision can look like it has ten related questions, and if asked in the wrong order, they can seem intractable. Often the best path through a decision is to pick the right question to start with.

Great framing starts by searching for the Eigenquestion, the most discriminating question in a set.

For a simplistic definition, the eigenquestion is the question where, if answered, it likely answers the subsequent questions as well.

As an example, let’s consider the YouTube story at the start of this doc ー what was the Eigenquestion. We initially started with the question “link out vs don’t link out.” We also had a latent set of questions that seemed unrelated: for example, should we build our own iOS app for YouTube?In our discussion, we reframed this to be focused on “consistent vs comprehensive.” In finding the “consistent vs comprehensive” eigenquestion, the YouTube team was able to turn one decision into a principle to be used in many future decisions.

The easiest way to improve your ability to find the eigenquestion is to practice.

• You run a mall. You’d like to increase the amount of foot traffic in the mall. What do you do?

• You run a company that operates in a very competitive space. You are debating between going upstream and downstream in the market. What do you do?

• You run an e-commerce website. You’d like to increase profit by running a few discounts. How do you decide what discounts to run?

For each of the prompts, write a list of your questions. Then rank them by the priority you’d think they should be answered. Which questions are the most important and consequential?

You could consider doing this for a company you are interested in working at. Or for a decision you have to make at your current company. I think you’ll be surprised by how useful it can be.

It will really stand out in interviews or in business meetings. Be the one to ask the good questions.

One version of an interview is you ask the boring questions: “What’s your day like?” Fine. But you’ll really stand out if you can ask the hard-hitting, thoughtful questions.

If I were to interview with a hot company like for example Delve, they build AI agents to eliminate compliance busywork, here are some of the questions I’d find a way to ask questions like:

• What is the bottleneck to growing faster right now? What’s stopping the company from growing 2x faster than it is today?

• When is the right time for you to expand internationally? How and when will you make that decision?

• What if AI gets too effective and can do all of this stuff in a general purpose sense without needing your expertise?

• How do you decide what to work on?

Simple questions that hover over the most important topics can go a really long way.

#3 - Sending great emails

I have written about emails many times before but I STILL find sending a great cold email to be underrated and rare. Reality is that so few people send great cold emails.

The first problem is that most people don’t send very many emails. I am not sure precisely why. Either they do not think it can be useful (in which case I disagree if you are looking to talk to customers or recruit people or find a job) or it takes them a lot of effort per email (in which case they should practice until they get faster!).

The second problem is that most people send bad or boring emails. Blatantly bad emails are pretty straightforwardly bad: they are hard to read. This could be from one of many reasons: they seem fake, they seem long, they are not clear, etc. Boring emails are also pretty straightforwardly boring: they are not compelling to the receiver of the email. I think you could be a top 1% email sender in the world by making your emails CLEAR AND NOT BORING.

You do not need magic AI. You do not need some niche engineering expertise. I am talking about hand-writing emails. And doing that quickly. And at a high-quality. If you can do that, I think lots of people will want to hire you.

This all sounds rather obvious when I put it in writing but I think you would be surprised.

You can read (even more of!) my thoughts on emailing here:

The guide to getting a job with cold email

You can also practice by sending me an email: hi@nextplay.so and also emailing companies from recent lists.

My actual suggestion is for you to practice sending emails. Literally time yourself as you send practice emails. Try to go faster. Spend 10 minutes a day for the next 30 days practicing writing emails, I think you’ll be really surprised by how much you can improve in a short period of time.

(Would more examples of emails be helpful? Let me know)

#4 - Staying organized

Were you ever assigned to do a group project in school? Flash back to that moment.

One of the things I remember when I think back to that first group meeting is the quick emergence of roles across the team. People like to take on different responsibilities. And one of those roles, really one of the more important roles really, was the “organized responsible person.” Now we didn’t give out this title explicitly but it felt like there was always someone who stepped up to be organized.

They scheduled the meetings. They booked the meeting rooms. They took the notes. They highlighted the important action items. They made sure we all understood the assignment.

They didn’t generate all the ideas. But they did keep everything organized.

Startups need this. They need good organization. Not in an extremely rigid way. That would be bad organization. But in an adaptable, fast-moving but still useful way.

You can be (or become) the type of person who is default organized. You come to every meeting prepared. You set an agenda. You do the pre-reads. You take notes during the meeting. You send the notes out afterwards. You set up the next meeting. You again set up an agenda.

You get the idea. This applies to any role. Whether you work on the leadership team or you work on the frontlines. Bring organization to the forefront and the rest of the organization will thank you.

If you want to get really good at this, my suggestion is to read books about high-performing, high-standards organizations. Like for example read about the Four Seasons. They will serve as good inspiration for you as you think about how to raise the bar.

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Was this useful? What skills am I missing? Email me hi@nextplay.so.

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