In my first startup founded in 2016, I was a student entrepreneur who had to figure everything out independently. Running a company is tough, even more so when one is a student who has to juggle everything.

Along the way, I’ve received plenty of help from individuals and institutions, whose only request was for me to pay it forward to the next generation of founders (besides buying them coffee).

And paid it forward I have. Since then, the kindness I’ve received was paid forward in various capacities, such as:

  • being a NEXT50 mentor, a TRIVE pay-it-forward programme
  • speaking on student entrepreneurship, e.g., TEDxNUS, Clubhouse, etc
  • mentoring in local and international innovation challenges, e.g., hackathons, innovation sprints, etc.
  • being the CTO-in-residence for the venture builder program in the Singapore University of Social Sciences

Mentors who contribute their time and energy, despite having highly limited amounts of them, will agree with me on this: it is fulfilling to assist, guide, and discover the next generation of awesome folks who will change society.

However, the tipping point for me came when I was involved in an entrepreneurship start-a-thon in the first weekend of May this year.

Long story short, I felt that my time was completely wasted with huge opportunity costs incurred due to a lack of professionalism of the organising team. Apart from my anger with the team, I am angrier with myself for not listening to my instincts, even though the red flags were present.

As such, to help fellow founders out there who are passionate about mentorship in events, I’ve compiled a short list of red flags so that you can decide whether it’s worth your time to pay it forward.

Red flag #1: The organising team moves slowly

You can tell how organised an event will be based on how quickly a team moves. How does one tell whether a team moves quickly or otherwise?

One such sign is how the team spends the time in between first contact and subsequent engagement of the mentors.

For example, let’s say you indicate your interest a month prior to an event. Instead of contacting you immediately to either accept or reject your interest to mentor, the team only engages you five to seven days before the event.

Also read: What you should expect from your startup mentor

What was happening in the three weeks between first contact and second contact? Who knows, but it’s irresponsible to leave someone hanging until the last minute when the mentor might have to shift things around to accommodate the team’s poor organisation.

To a busy entrepreneur, one week is not a lot of time to change plans just to accommodate the timing provided by the team.

Time is a resource that you’ll never get back once you lose it. If the organisers don’t respect their own timeline, don’t expect them to respect yours either.

Red flag #2: Poor communication

Organising an event requires multiple stakeholders to be in sync and aligned, and it is impossible to do so without poor communication.

As such, a red flag to watch out for is how well the organising team communicates with you. A lack of communication/lack of coordination in communication is a precursor to things messing up, be it before or during the event.

A good team over-communicates and ensures that you know exactly what you need to do, and when you have to be there. On the other hand, a poor team does the opposite and leaves you in the dark.

Apart from communication between the team and you, watch out for signs of poor communication between team members as well. The most telling signs:

  • repeated messages to you
  • slow replies with scant details
  • lack of coordination amongst team members
  • having poor email habits

If you catch yourself asking why it’s so hard to talk to the team or find yourself confused, it’s time to reconsider your participation in the event.

Red flag #3: You ask yourself “what’s going on?”

A mentor’s job is to go into pre-arranged sessions and support the participating teams in their bid to create the next big thing. Thus, the onus is on the organising team to ensure that this happens smoothly. In fact, all of the thinking should have been done for you by the organising team.

Also read: Meet Mentor For Hope, the startup mentorship programme that will donate 50K meals for those in need

At any point in time, if you have to take the initiative to ping the team to get updates or are in constant doubt, you might have to be mentally prepared for things to go awry.

In fact, if you have to guess what’s going on at any time, it’s probably not a good idea to stick around the event.


That’s all folks, the three red flags that one should look out for.

Organisers, if you read this and you felt like the red flags applied to you, please commit to improve for future events. Organisers-to-be, I hope you share this piece amongst your team members as a cautionary tale as you organise your events. In fact, these red flags are meant for all kinds of events, not just startathons, hackathons, or any -athons.

Fellow mentors and individuals thinking about helping out in hackathons/events/challenges, I hear you that it’s important to contribute time to the ecosystem. Use this list of red flags wisely in the future as you decide how you want to contribute.

At the end, I hope this piece will lead to a change in how events involving external mentors are run. As for me, I’ll be taking a break from paying it forward unless it’s a warm referral or a request by trusted peers and just focus on hustling.

Founders, you should focus on hustling too unless the reasons to mentor are extremely compelling and the organising team respects you and your time.

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Image credit: Akson on Unsplash

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