Social BusinessApril 25, 2018

Seven deadly mistakes to avoid as an entrepreneur

Life as a leader can be fraught with errors of judgement; here are the most common ones to avoid — so that you don’t have to learn from your own experience.
2019-10-04 00:00:00 India Development Review Seven deadly mistakes to avoid as an entrepreneur
4 Min read Share

I am not usually a big fan of management books, but I recently read The Hard Things about Hard Things by Ben Horowitz and was hooked. What struck me was that rather than give clichéd answers to what it takes to be an entrepreneur—passion, persistence, belief in your dream and the like—it offers a brutally honest account of mistakes to be acknowledged and actions to be taken when nothing seems to be working. It inspired me to reflect on the biggest mistakes I made as an entrepreneur and what I would do differently.

1. If it’s not your strength, pay extra attention to it

I was lucky to start three organisations with a co-founder who made up for all the things I wasn’t good at. As a result, I barely paid attention to those things. However, when I took up responsibility as CEO, not only did I have gaps in my skillset but it also took me painfully long to get up to speed. I can honestly say that my biggest errors of judgement were in those areas.

It’s okay to rely on experts as long as it doesn’t turn into a blind spot for you.
Most social entrepreneurs will have things that they hate spending time on—numbers, systems, HR, impact metrics, media—and will happily delegate these to a co-founder, team member, advisor or consultant. It’s okay to rely on experts as long as it doesn’t turn into a blind spot for you. Never forget that as founder/CEO, the buck stops at you and not the expert.

Related article: Fundraising 101: Four steps you can take today

2. The devil is in the detail of a scale model

As a mentor, I often meet young entrepreneurs thrilled at any opportunity for scale. It is also very common for them not to think through the details before accepting a corporate’s funded offer of expanding to a new state or a partner’s offer of opening a chapter in their city. I was exactly the same. With the result that we grew our offering and reach in a short span of time.

While it was a joy to see our work expanding, we also spent a lot of time fire-fighting issues that we just hadn’t prepared for. If I was to do it all over again, I would (a) spend more time poring over every tiny detail, especially on aspects that are critical success factors and hence non-negotiable and (b) make sure the scale team was adequately resourced with talent, funds and systems.

3. At certain levels of innovation and scale, a good CFO and compliance team are a must

I often see social entrepreneurs getting confounded by the various interpretations of charity laws and compliance in India. There should never be any compromise for a high-quality CFO and a sound compliance person/team, especially if your business model is innovative and at a particular level of scale. I can hear you say, ‘Well, if only I can afford the good ones.’ Treat it as an investment to protect your work.

4. It’s not final until the money is in the bank

I still don’t think I have fully learnt this lesson. I still get excited by conversations where a funder shows positive interest in our work and asks for a proposal ASAP. I then get extremely puzzled when they go missing on mails or when the contract gets pushed out by quarters (not even months) or when the transfer of money never seems to be around the actual dates in those contracts. Always remember the fundraising mantra: There are no guarantees until it hits your bank account.

5. There is a fine line between being humble and being naïve

We began UnLtd India on the premise that our work should and would speak for itself. That it would attract the attention and support we needed. Hence, most of our media coverage and public appearances were a result of people finding us as opposed to any proactive efforts from us. While this built us strong goodwill in the sector, it also stopped serving us over time.

A lot of my first-time meetings would end with, “You are doing such amazing work. Why have I never heard of you guys before?” I also saw us losing opportunities to organisations that were new on the block but savvier at showcasing their work in the right circuits, in the right way. Don’t hesitate to trade in some of the humility for some of that savviness.

6. Don’t procrastinate when you know it’s time to let go of a team member

In my experience, you can identify potential issues with team members pretty much in their first two months at work. More importantly, your gut will often tell you whether those issues can be resolved or not. When it comes to letting go of a team member, I always prefer to give feedback and opportunities for them to improve their game or attitude. However, there has to be a limit to how many chances you can give. Procrastinating on a decision that is staring you in the face is never good for the organisation and for the individual.

Related article: Waking up to the talent you already have

 7. Don’t be a bottle-neck

I struggle with the phrase “Done is better than perfect.” However, I do believe when you are juggling so many things, it is important to know what needs perfection and what just needs to get done. I am not making a case for mediocre performance but there are certainly instances I can remember when delays could have been avoided if I had only let the team get on with things without needing my approval. The more approvals they seek, the less confident they feel in taking decisions, the bigger bottle-neck you become.

Life as an entrepreneur and as a leader is moulded by mistakes and errors of judgement. A bigger mistake is to not pay attention to the valuable learning at the core of each mistake. As I recently read, “You can never make the same mistake twice because the second time you make it, it’s a choice.”

We want IDR to be as much yours as it is ours. Tell us what you want to read.


We hope the conversations that take place on will be energetic, constructive, and thought-provoking. To ensure the quality of the discussion, our moderating team will review all comments and may edit them for clarity, length, and relevance. Comments that are overly promotional, mean-spirited, or off-topic may be deleted per the moderators' judgment. All posts become the property of India Development Review.
Get smart.
Sign up for our free weekly newsletter, IDR Edit.
Follow us
Get smart. Sign up for our free weekly newsletter, IDR Edit.

IDR is India’s first independent media platform for the development community.

We publish cutting edge ideas, lessons and insights, written by and for the people working on some of India’s toughest problems. Our job is to make things simple and relevant, so you can do more of what you do, better.

IDR is produced in partnership with Ashoka University’s Centre for Social Impact and Philanthropy.

Privacy Policy | Terms of Use | Contact
© 2020 India Development Review    
India Development Review is published by the Forum for Knowledge and Social Impact, a not-for-profit company registered under Section 8 of the Company Act, 2013.
CIN: U93090MH2017NPL296634