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How to choose what startup to join
Making the right choice as a Product Manager or Leader
I have been talking lately with many product guys in Greece looking for the next step in their careers. Thus, I decided to describe what startup I would like to join based on my experiences and how I would go into an interview with a startup.
There is no ideal moment to join a startup as a product manager or leader; if it is a startup, you should expect to struggle against the unknown on seeking market fit while growing organizationally.
Everyone would like to join a startup run by an ex-product-driven entrepreneur, but this is not common, at least in Europe, especially Greece. Thus, you shouldn’t expect to find a ready-to-work environment, and part of your job will be to train people and build a product culture within the organization's limits.
It would be nice to recognize a “good startup” to join as a Product person. Ideally, a promising startup to join has:
A Product that you understand and preferably like. You should play with the product (have a demo if it’s B2B), talk with the team you are about to join, and understand if what they describe is what they have been building. Try to understand the unique advantage, don’t rush to raise your concerns, and try to listen.
A passionate Team that can align with your views. You should put more emphasis on the people you will work together, aka the engineering, sales/business, and operations counterparts for your role. Of course, your manager (or the CEO) is also essential, but you need to work with a team on the same level, or you will have to help build the missing counterparts.
A good Financial state means having a break-even or having secured the required funds to run for at least 2 years. Financial pressure creates anxiety, anxiety blurs judgment, and people turn to their instincts or rationalizations. Working in a startup will be a ride, but it doesn’t have to be tough. The company's age, any strange acquisitions, the number and size of investing rounds, and the number of people are indications of its financial state.
Tech understanding, tech people, and excellence should be evident in the way of thinking. Try to recognize and avoid people talking about “tech” but not “products” or about “engineers that don’t get it and are spoiled” but not about product teams; they probably consider “tech” a cost center, and you will have to explain all the team how teams should work to create additional value with products.
They have a Vision, and you like it. You and the teams need inspiration and somewhere to link the strategy and the actions; if there is traction, the vision can be a catalyst for successful growth, the north star when decisions are tough. If you don’t like where the startup is heading today, you probably won’t like it later; if someone gets a consultant to build a vision, nothing will change. The vision and actions that prove that teams are working to achieve it are empowering and will make your life more pleasant.
Business people or co-founders who talk about Customer needs and customer-oriented thinking. You should dive into how they get feedback and how they apply it. You should avoid people talking about “stupid users” to point out their intelligence.
Things that are red flags for me :
Co-founders with big ego. It is part of your job is to educate and manage up, but it will be a toxic environment even if the company gets successful. To recognize it, you should spend some time together and try to realize if you feel comfortable with how they talk and behave.
Big promises. People talking about fast growth without a straightforward offering and an apparent problem, talking about building the next Google and Apple.
Avoid business people talking about money, evaluations, rounds, and market size while stating how stupid competition is, knowing the market exceptionally well, and opening doors with customers like no other. It will be tough to collaborate with people who know everything about the market and don’t want to talk with anyone.
Being fuzzy about stock options plans and the terms. You can be optimistic you will find a way, but people get greedy as they face success. A company that grows beyond 10 people must have clear and transparent governance, and your deal is based on what’s the stock plan too.
Things that I don’t emphasize even if I consider them and try to understand more through discussion:
Selling Services instead of Products. This is tricky. If a company has raised money to build products and does custom services that don’t scale, it will soon go into tough times with the investors. If they are in the beginning or bootstrapped, it may be a wise tactic to go into a market and get validation before they build something that scales, especially in B2B.
Designs of the product. We all like products with lovely designs. Instead, you should try to understand why customers use the product even if it is not nice-looking. The value is elsewhere in the early stages. On the other hand, a big team without “aesthetics” or confusing design signals that you will have some work to do in that direction.
Website. I have worked for B2B companies that made money even with an awful website. What is annoying is that you can’t understand many things, and you have to make more questions to understand what’s all about.
Awards. No one should care about awards when joining a company.
Product Questions to ask
Below, I list an extensive but not complete list of questions you can ask while discussing joining a startup. My advice is to avoid calls if possible, you should be able to visit the offices physically and talk in person with the team, at least in the latest stages of the communication.
“Who runs the product today?” Typical answers are “we are doing it all together”, “we have promoted someone from the [x] department,” or “the [y] co-founder(s)”. Based on the answer, you can understand when you will need to focus and potentially ask to talk with these people.
“What’s the size of the engineering team?” You should know the ratio of the engineering, as it is an indication of company strategy if they grow through tech or sales.
“Who talks with the customers today?” If the teams already have access to customers, it’s great. Otherwise, you have to meet the sales/business guy and see if you can work together. Also, you should understand if they look for confirmations or if they actually look for customers’ problems.
“What do you expect from a product team within the company?” If you get an answer like “I want you to become the CPO next to me,”it is translated as “I have no idea what the product is about, but you will build what I want”. Typically you should see someone recognizing their pains, understanding that they have reached a ceiling with product management and need an expert to take over.
“How do you decide about what will be built?” Early stage, you expect the co-founder to be this guy. If the answer is similar for a larger organization, this is a bad sign you must discuss it in detail before you join.
“Who is responsible for the architecture?” If you are lucky, they will understand what a product architecture is, and possibly some of the cofounders will do it. The most prominent answer is “[x] from engineering”, confusing the product with the tech architecture, which is ok, it shows an engineering mindset. It is also possible that you get no answer; this is not a tech or product-driven company.
“Who is responsible for delivery?” This question exposes the engineering seniority and the organization's maturity. If you get an answer like “the co-founder or the PM”, you have to change things to explain that engineering must be accountable for the output.
“How do you work with engineers? Do you have any framework?” This is the question that you can make you understand if engineering is a cost center or value creation factor.
Additional questions to ask
Apart from understanding the product mindset of the team, you should learn more about the organization.
“What’s your ARR” and “Have you/When do you expect to break even?” You can understand the financial strategy.
“Why are you better than the competition?” You need clear, non-emotional answers. Ego may rise here.
“What’s your vision for the company?” You will be surprised at how many bad questions you will get. If you don’t like the answer, people within the company won’t like it too.
“What’s your strategy to grow the company?” Typically the answer you will get is not about strategy. It’s tactics, operational, or some buzzwords.
“How frequently do you sync?” and “Do you work remotely or at the office?” As remote and hybrid are parts of our life, you should know if this model fits your needs. I like face-to-face syncs where traveling may be required.
Don’t make it look like an interview
You should ask for an interview with casual face-to-face meetings, while you should meet various people from the team, not only the hiring manager or the co-founder. Don’t go through a list of questions, it will be like an investigation, and people won’t like it, as you wouldn’t like it either.
Also, this is not a quiz. “Bad answers” are not the end of the world. You should weigh the importance of each criterion for you and understand that often it is part of your job to fix the problems you identify. Still, you must understand if the organization is willing to change and improve, this is the most critical question to answer.
You need to understand if you can work together with these people and which cultural, financial, market, and organizational limitations you may face.
Part of your job is to educate the organization if needed, build a structure and drive the company into a new era. Hopefully, the company has been building a product and an engineering culture, making it easier to apply standard practices. Don’t get scared by companies that are not product thinkers or if they sell services; It’s about your expectations, your energy, and your belief that this relationship is going to work.
I am happy to learn if this article is helpful for you and how you go into discussions with startups to choose the next step in your career.