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Want To Join A Startup? Consider Asking These 10 Questions First

Want To Join A Startup? Consider Asking These 10 Questions First

Startups intrigue people. On one hand, there’s the uncapped potential for growth, the exciting missions that often contrast corporate alternatives and the never-a-boring-day speed. On the other, there’s the risk that the startup is not going to make it to the next funding round, the fierce competition that some of the more exciting missions attract, and the poor work-life balance and toxic cultures that may emerge.

If you’re thinking about joining a startup, make sure you do your research first. The best interviews are often balanced conversations, don’t be afraid to ask your questions. While your skills, interests, and goals will inform specific ones, here are 10 more general questions worth considering.

What is your cash runway and how are you thinking about the short to medium-term capital requirements of the business?

This is a question that many candidates omit, especially if they’ve never worked with startups before. Knowing when the company expects to run out of cash and what their options are at that point is highly valuable information that can impact your role at the company before not too long.

Venture-backed businesses tend to raise capital as part of one funding round for at least 12 months, quite commonly 18 months and increasingly so for longer. You can often find information online about the startup’s fundraising history and come up with a rough estimate. However, even if you do your desktop research, it’s still a question worth asking during the recruitment process. There can be a significant time lag between when funding rounds close and when they get profiled by tech publications. Plus, it helps to understand how the team thinks about the options they have ahead, not just the pure timeline.

If you want to dig deeper, perhaps especially relevant for more senior roles, ask them what milestones they were hoping to achieve when they last raised and how the current reality compares to those previously set expectations. You can also ask about the investors who backed them before and about their approach to follow-on investments. Q Hamirani, People Leader at Airbnb, suggests further asking if any of their previous investors have already participated in the company’s follow-on rounds. “This could show the continued optimism and support from their investors”.

How do you approach employee onboarding and training? Following that, what opportunities do you see for career development and progression?

For candidates who previously had corporate roles, it might seem inconceivable to join a company and not undergo rigorous training. The reality of startups is that the quality of the onboarding and the support provided at the beginning can vary hugely. In some cases, it can feel like being thrown into the deep waters and teaching yourself how to swim.

Some people are more comfortable with this reality than others so it’s important to understand the startup’s specific approach and its fit with your personality.

As a general mindset for when joining a startup, it helps to be proactive and ask for support as and when needed versus waiting to receive it in a structured way. It also helps to brace yourself for a steep learning curve.

On the plus side, career progression can often be accelerated in line with the growth of the startup – especially if you join early and there are no pre-defined seniority bands or job descriptions.

If the answers you are getting are too vague, you can ask some more probing questions. Vaibhav Bhatla, Chief of Staff at Monzo, suggests: “1. How do you see the balance between on-the-job and formal training? 2. Which people within the team do you think I could learn the most from and how so? 3. What has the recent trajectory of people in this kind of role been?”.

To what extent will my role involve creating new processes or improving existing ones?

The earlier you join a startup, the more you are typically responsible for creating – or at least contributing to – processes from scratch. Your role will inherently go beyond pure execution. If you’re used to more structured roles and working environments, this may come as a surprise.

While also challenging, part of the beauty of startups is the exploration and iteration that you can expect. Rather than operating with legacy processes and within the existing structure, you often can get the chance to co-create it all.

This question can also reveal how much freedom you’re going to have in deciding how to best reach the set targets.

What is the process for making decisions internally and what is my expected level of involvement or input?

This can vary significantly between startups, depending on their culture, the stage they are at, and the industries and regulatory environments they operate in. Ideally, you would want this to not be too dissimilar from your preferred approach.

“I’m someone who finds it rewarding to solve problems at a fast pace. I don’t like to go through hurdles of bureaucracy to get something done. This to me – the need for a review of every decision – is how I view inefficiencies in a small startup where the pace is everything. So on this point, it may just not be the right environment for me to feel fulfilled,” expands Sophie Theen, Startup Advisor and Coach.

A question that Q Hamirani likes to ask is: “Tell me about a time when you disagreed with your team members’ strategy and how you went about it.” In the answer, he seeks a willingness to consider diverse viewpoints and receptiveness to trying the idea, even with the understanding that it may not be perfect on the first try.

What is the expected compensation for this role, and is there room for negotiation on the components of the package?

In addition to base salary and bonuses, startups can offer equity as a way to attract and motivate employees. As startups are often resource-constrained in the early stages, they may not be able to compete with established companies on base salary. To compensate, they often establish an option pool, a reserve of equity set aside for employee options. This allows them to offer stock options, which give employees the opportunity to purchase equity in the future, often at an attractive price.

When joining a startup, you may have the opportunity to negotiate the balance of salary and equity options. Make sure you understand how options work – including vesting schedules, strike prices and call options – to make an informed decision when comparing the attractiveness of different offers. It is important to view yourself not only as an employee but also as an investor; to consider the point at which you would be joining that startup, the potential upside ahead and the risk-reward tradeoff.

Beyond salary and equity options, do consider other benefits or lack of them, as these would typically be quite different from more traditional companies.

What is the startup’s north star metric and what do you see as the biggest potential threats to its growth?

Before joining a startup, aim to understand how your role contributes to the bigger picture. How your efforts can impact the key metrics and how you can help mitigate some of the risks ahead.

Freddie Birley, Mindset and Performance Coach, suggests also asking: “What is the ultimate metric of success for this company?”. Going beyond the short to medium-term goals can give candidates an insight into what ultimately drives the team. Is it achieving unicorn status, impacting a certain number of lives, solving the problem, changing culture, reaching a financial outcome or something else altogether?

To further reveal how thoughtful and informed the founding team is, you can ask about other companies that have been trying to solve similar problems or propose comparable solutions. Why did those companies not succeed and how are they going to approach things differently?

What are the company values and could you share some examples of how you are living those values in practice?

Many candidates ask about the company culture but they are often given generic responses that don’t actually paint a picture of the day-to-day reality. That’s why it helps to ask more specific questions about how that culture is manifested in practice.

Merita Ramadani, VP of People at Payhawk, suggests asking: “When it comes to the values, what was the process taken to come up with them and have they changed over the years?”.

“The question I would ask the interviewer is how they build trust in their teams. If the answer points towards micromanagement then I know for sure this isn’t the right environment for me to be successful,” shares Theen. A follow-up question could be: How do you keep in touch or build working relationships with those who don’t work in your team? “This is a great question to help candidates get a much better understanding of the human and social elements of this company. Navigating through distributed teams is becoming more and more challenging so any effort the company puts in to keep this a top priority shows a people-centric company.”

Birley recommends asking: “What are some of the qualities and behaviors of a rockstar team member?”. This can help focus the interviewer while giving the interviewee a more specific idea of behaviors that quantify success inside the company.

To find out how people might behave under duress, Q Hamirani proposes asking: “How does the team work together to solve critical problems? Say we’re about to lose a major customer, what do we do and how do we organize ourselves? Whether we believe it or not, many toxic environments stem from the stress that is unmanageable.”

Taking it one step further, you can ask what they would do if the product they sold today was unable to get market fit as anticipated, or was no longer as needed due to changes in market conditions. This is a question that Q Hamirani suggests as a way to assess agility and humility to adapt and pivot.

Why did you start or join the business and what is still making you excited every day?

Understanding what motivates the team – a technical challenge, an overall worthy problem, impact potential, ownership, or returns – can help you better understand the company and its trajectory.

When speaking with team members, Ramadani encourages candidates to ask: Why did you join this company instead of any other company you were interviewing with? Has your experience lived up to these expectations? What were the biggest surprises?

When speaking with the founders, it’s also interesting to ask about the origin story: How did the company get started and what is the founder’s connection to the problem/opportunity? The answer can help shed a light on the initial startup DNA.

Theen likes to ask if existing employees are fulfilled doing their jobs and why that is the case. “It’s a directly emotional question to ask your interviewer to truly get an insight into the ups and downs of their job and indirectly the environment you are going to be working in. A question like this strikes a bond with the current employee in a way that you get to understand why they are still working here. The correlation between a person’s tenure plus reaction to this question will help this candidate predict what it takes to thrive in this company.”

What is this startup enabling? If it succeeds what would the world look like?

“I would encourage candidates to understand the mission and purpose of the product and company to ensure it aligns with their own principles. Working for an organization that sells products that do not align with your values or principles can result in longer-term disappointment and lack of engagement, overall motivation and happiness,” highlights Q Hamirani.

Ask yourself: If this startup fails, do I see myself working with this team again?

In the startup world, working with and for bright people is rarely wasted time. If you see yourself working again with the people you would be joining, that’s a way of essentially derisking your decision.

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