Jenny Chiu

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On November 22, 2015, Jenny commented on Does your startup have a devil’s advocate? :

Thanks Kaushik for your post! I also believe in the power of devil’s advocate to help us identifying blind spots and providing a new perspective. However, I wonder whether it takes certain condition for devil’s advocate to be effective. For example in Curt Schilling’s case, even though his female CEO has stated multiple times how the company process should work and seemed to explain to him why it is important for her to take charge, he still can’t control himself from pulling out his checkbook when his employees need more money. To me, I think there are a few factors play in for devil’s advocate to be effective:
(1) The devil needs to be well respected – I found it if the devil is someone who is powerful in the organization, or has relevant experiences or established credibility in the past, it is much easier for him or her to be in the position to challenge the majority thinking.
(2) The listener needs to be open-minded – similar to providing feedback, it is truly a gift for someone to offer honest opinion because it takes courage to do so and it helps you to learn better. However, if someone is defensive about it, it would be really difficult for that person to actually appreciate the intention and focus on the learning.
(3) Devil’s advocate is more effective when company is not in a good position. If a company is in a good position, it is less likely for people to take in opposite view because “my plan just works perfectly!” Ironically but true, it would be easier to start the conversation by objectively analyzing the company’s position, and frame it as a threat if such opinion is not taken seriously.

On November 21, 2015, Jenny commented on The Unicorpses :

Thank you Kaitlyn for your post! Your post has reminded me of what I learned from BSSE (surprise!). We talked a lot about disruptive innovation, in which many cases are small startups. These startup enjoys high growth because they did not get the incumbent’s attention until they are too big to ignore. However, one thing I took away from that class is how these startup, once successful, have to keep innovating themselves out to defend their position from future disruptive innovation. On top of what you have mentioned, I think there are a few things that these successful startups can do to keep them in the growth trajectory:
(1) Keep asking “What do my customers want” constantly – In LivingSocial, the initial customer needs is to explore local new businesses through discounted offers. However, the customer needs probably change in times as they have explored enough of the local businesses. Sometimes your success could end up become the obstacle for your next one.
(2) Know that your team might also need to change with the needs – it was sad to let go with the people who have fought the initial battle with you. However, sometimes their skill set and expertise is no longer relevant to the changes that the startup is heading to. Founders have to make tough decisions to keep the company growing, sometimes it means replacing their loyal team members or even themselves.

On November 21, 2015, Jenny commented on #1 rule of successful failure: Fail early :

Thank you Helena for your post! While “if fail, fail early” is true, I found it quite contradictory to think about the perseverance we need when we do our startup, and wondered how can we draw the line when we decide we should persist vs. we should “fail well”. Here are my 2 cents added to this post:
(1) Know your risk profile well. For some, it is okay for them to burn extra money to push a further mile through. For some, there would be a point your intuition tells you this is too risky for you to go on. There is nothing wrong which options you take, but just be honest to yourself when red flag arise.
(2) What is your alternative. Analyze your situation as objective as possible when things go wrong, lay out the options that you have, as well as the pros and cons for each situation. Some people have a well-paid job to go back to, but it’s the only option left for some. Some has more funding sources they can tap into to get through the tough times, whereas some would be in a even more dire situation if they take on additional debt. Maybe in the end, the decision you made is from your gut, but at least by laying out the facts, your decision is a more informed one.