8 essential questions to ask yourself before joining a Startup or you’ll regret for life

Startups usually operate in an “all hands on deck” kind of environment whereby every employee might hold a few different roles at the same time due to the limited number of people in the team and also not forgetting the risk factors that could be involved especially for an early-stage Startup.

Thus, accepting a Startup job offer would not be an easy decision for one. Yet on the other hand, joining a Startup can be fun and a great learning journey experience for you! Moreover, it can also act as a stepping stone towards you being an entrepreneur yourself one day!

Therefore, if you are looking to join the community of Startups, you should take some time to ask yourself the “right” questions and you’ll be one step closer in making the right decision for yourself. Here’s a little help for you in achieving that.

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1)    At what stage is the Startup that you are being offered a position?
If the Startup is still in an early stage, definitely it involves more risk. You will also need to know how the Startup is funded to determine the level of risk you could be undertaking.

2)    Will the role being offered give me a much greater learning insights than my current job?
In a Startup environment, you might be taking up a few different roles at the same time or your role might vary as the Startup progresses. How much more you can learn would depend on how much you already know about the role(s) you will be handling.

3)    Do I have the right personality to work in a Startup?
Meet and talk to the different members of the Startup you are intending to join. You could be working long hours (doesn’t necessarily applies to all Startups) and the entire company could just be lesser than 5 people in a small co-working space.

It would be good to know if your personality can work well with them. You would not want to be caught working in an environment where it is comparable to be like working in a graveyard, would you?

At the same time, you could also find out more about your future team members and learn about what other knowledge they can impart to you.

Next, ‘It’s all about Adaptability.’ Do you possess traits like a chameleon? Startups are constantly in the motion of changes with popping out of new ideas to discuss and new projects to work on. Are you ready to always be on-the-go?

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4)    What type of worker am I?

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‘Clear directions will always be given.’ If you are thinking it is so then you are wrong. There wouldn’t always be clear directions given to you if you are working in a Startup unless perhaps if you ask for advice from a fellow colleague or your superior.

Are you self-motivated and task-oriented enough to know what to do and figure out how to be useful? Remember! No one is going to tell you what/how/when to do it. You have to be constantly ahead and able to be intuitive enough to act as and when needed.

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5)    What will my role be?
Do you have an identified role or will there be a chance of additional roles being given to you along the way as the Startup climbs up the ladder? What kind of responsibilities are they prepare to give you and how prepared are you to take them on?

You must be clear on the roles and responsibilities that you will and may have to handle in order to access if you could handle the workload in time to come.

6)    Do the founders talk the talk and yet do not walk the walk?

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Startup founders need to talk the talk and walk the walk. Although, you are hired to do the work but are the founders putting in the same if not more amount of efforts than you? You would want to be assured that when a situation arises in the Startup, the founders will be there holding the grounds together with you.

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7)    Why am I doing this?

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There are various reasons why a person will join a Startup. It could be because they don’t like their job, couldn’t find a job, equity ownership, and learning curve of being an entrepreneur etc. What is yours? Is it Passion? Do you have a great interest and belief in what the Startup is doing?

Do note that Startups might take some time before you will see any fruits bearing on the tree, thus, you will need to evaluate your vision of your own future prior to making a commitment to the Startup.

8)    What are the risks?
Joining a Startup can be risky at times. Your time and effort will be significantly chained to the Startup and yet they might fail quickly too. Therefore, you would want to consider if the Startup should wind up, would you still be able to stand on your feet? Will you still be able to serve your commitments if there be any?

Will you be able to see it as a learning journey and not allow setbacks to prevent you from embracing your future, should the Startup fail?

With a good research on the Startup you are thinking if you should join, you will be able to determine the level of risk you might encounter and at the end, it will be how you feel about managing the aftereffects should it not work out.


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All in all, I feel that you should consider about what is most important to you. The learning experience that you foresee you could have or the environment you prefer to be in. Is money an important factor to you at this current moment of your life or do you have any other commitments that you have to consider about.

Working in a Startup is indeed challenging, consumes quite a chunk of your time and your responsibilities might also vary. But definitely, in the right Startup, a great learning opportunity awaits you!

So, good luck!

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This article was first published on goodyfeed.com

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Startup Jobs Asia was "brewing" yet recognizing the challenges of Talent Acquisition that Startups faced both in Singapore and within Asia. We have identified the in-between gaps and aim to drive through them to bridge the gaps narrower as we move forward. With decades of combined experience in recruitment, we understand the challenges that Startups and jobseekers face today. We aim to create a better leverage and platform for Startup Hire in Asia and help connect the right talent fit within their growing and emerging business. We want to "sexify jobs @ startups and to grow the human capital eco-system for startup." in short we want to be the voice for startup hire within asia.