Due to some personal changes, I'm currently planning the next step in my career. The last time I was in this position, I mostly went with the flow, exploring options, and finding along the way what I cared about. I thought it was an excellent time to synthesize my learnings to help me think about my next step and help others on the same journey while sharing some examples of my journey.
Spoiler alert: compensation is not part of the criteria, as I recently explained in this post
A tri-factor approach: Product, Culture and Role
My approach to evaluating a tech opportunity involves looking into 3 areas: Product, Culture, and Role. A golden opportunity would have the following characteristics:
a product that you are passionate about and are bullish in its long term prospects
a company culture that you relate with and with people that you admire and want to work with
a role that will make your next few years of learning exponential (rather than linear)
Assessing the Product
The product is a critical part of evaluating a tech opportunity. You want to do some initial filtering based on the things that you (which industries you want, which product stage you want), but then you should try to immerse yourself in the product in the following ways:
Try the product - if you are not a user already, sign up and play with the product. You will learn a lot by doing that. For example, while interviewing at Doordash, I signed up to be a driver and went to do some deliveries. With that experience, I learned that the TAM for food delivery is much higher than I thought (when I made a delivery to a security guard on a shift) and that food delivery has enough differences versus rideshare that Uber did not have a material advantage (when spending 10 mins waiting at Burger King waiting for an order)
Talk with the product customers - interview current product customers and assess how they use the product and how essential is it for their lives. For example, I'm currently evaluating a potential role in a SaaS company, so I reached out to some clients to understand their use cases and assess how replaceable is the product for them.
Understand the product vision - Read about the company if there is material or news articles. And then ask in the interview the most senior person where they see the product 5 years from now. I recently was in conversations with a consumer product that I thought would be mostly an exciting niche product. The answer to that question made me realize how much more significant potential the product had to achieve mainstream adoption.
In the end, ask yourself the following questions:
Am I bullish about the long prospects of this product?
Am I passionate to work on this mission for the next 5 years?
Assessing Company Culture
The company culture is typically overlooked, but it is an essential component of your decision. It will play a critical part in your development in the new gig by determining how you will feel and how challenged you will be. Here are some ways to understand the company culture:
Get to know the founder - the founder's personality and ideas can tell you a lot about the company culture, so you spend some time studying them. When I was applying to DoorDash, I listened to multiple Tony Xu interviews. What impressed me about him was his consistency across the years (on Doordash's merchant first strategy) and his personal story of being clearly passionate about helping small businesses.
Ask culture questions - when you are in interviews/coffee chats, make sure you ask culture questions, especially on things you care about. Getting the positives is easy, but it is also essential to ask questions that help you picture the negatives, like something they don't like or would like changed.
Get external perspectives - the current employees will always be biased into the company's positives, so try to find in your network either past employees or friends' friends that are employees who can tell you an honest picture. For example, by talking with a current colleague who was an ex-employee in one of the startups that I was interviewing, I discovered that the founder was quite temperamental, having fired the entire salespeople once. Not the kind of culture I was looking for, thank you.
After digesting what you learn about the culture, ask yourself the questions:
Do I admire the company culture and values?
Would I work for the people that I talked with?
Assessing the Role
The role only matters if you have positive signs of the other two. No position is worth it doing if you don't believe the product or despise the culture. That said, it is still a critical part of your evaluation, and here are some ways to do it:
Define what you want to learn from your next role - you should spend time defining what you want to get out of your next position. In my case, I wanted to increase my scope and had the opportunity of starting a new product, so when given the option to pick between different teams at DoorDash, I ended up choosing the DoorDash Drive team, which was in an earlier stage than some of the other groups.
Assess your manager - your manager will probably be the person you will have the most opportunities to learn from. You want to find a manager that inspires you and that you think you learn from. Spend as much time getting to know them before making the decision. If your hiring manager does not have time to spend with you answering your questions, it is already a bad sign that they will not invest in you as much later on.
Opportunities to grow - understand what could be the future for this role. Will, the team, continue expanding, and will you be able to increase scope? Will you be able to transition to a different role later on? Try to match those things with what you want long term from your role.
After digesting what you learn about the role, ask yourself the questions:
Will I love to do this role?
Will this role accelerate my learning?
How to get to a combined assessment
Now that you did all your detective work, how do you get to a decision? There is no magic way here; the expectation is that you probably have a strong preference. By now, after collecting so much information.
As a rule of thumb, if you are early in your career, you should focus mostly on Product and Culture, as it will be more important to learn from a strong culture and product than having the "right role."
As you become more senior, the role you take becomes more essential to develop specific skills, and the more senior the position, the more control you will have to improve Product and Culture.