Winning startups stay curious

Early stage companies embody curiosity. They aren’t sure they have a good market, they don’t know exactly what customers want, they haven’t figured out how the technology actually applies. They ask a lot of questions. They try things. They aren’t attached to the things they try because they can’t afford to be. 

Later, or when you raise a lot of money, these things change. Perhaps because you could raise $20 million from a famous VC, you think you know more than your prospects. As soon as you become attached to being right, unwilling to let experiments fail, unwilling to ask questions and actually listen to the answers, you will start to struggle.

Here are some tips to stay curious and create a culture of curiosity:  

1. Ask questions. Try to never make a statement. Just ask questions. Simple, but hard. For example, when a prospect asks you, “What does your product cost?” Instead of stating “$1 million”, ask, “What would you say if I told you it cost $1 million?” 

2. Reward asking questions and getting answers, not being right. This applies to won deals, lost deals, all aspects of the sales and go to market phase. You personally can apply this to product development. When your team ships a feature, and shows it off internally, make sure to ask what questions or customer comments led to the creation of the feature. 

3. Avoid assumptions. Just because a prospective customer has the same use case as an existing customer does not mean they see the same value in your solution. 

4. Repeat the need to stay curious in your sales team meetings, all hands, and everywhere else. 

5. Play dumb. My sales coach used to call this “dummying up”. Ask questions you (think you) know the answer to, just avoid being patronizing. Even if you’ve talked to 5 identical customers, if you ask questions rather than make assumptions, sometimes the answers will surprise you!

6. Use the 5 whys method. Ask why five times to get at the real issue. This is a well-documented and effective discovery method–and applies beyond product development. Though–avoid using the word “why”, because it puts people on the defensive. Try “What led to that idea/process/etc?” instead.

Learning to stay curious and specifically ask questions was the biggest unlock in my performance across all aspects of my life, personal and professional. 

It started with me pitching to a very famous angel investor, one of the first investors in Google. He peppered me and my cofounder with a lot of very pointed, good questions about our vision, business, and technology.  We’re both smart people and we knew our stuff so we answered them. We had strong opinions in some areas. At the end of the meeting, he said he’d invest $500k, which at that stage was a lot of money–from a huge name. It was company-making. Our advisor who made the intro said he’d follow up with particulars. We went to the Rosewood to celebrate.

A week later, nothing had happened. No investment documents, no wire, nothing. I asked what happened. Apparently, he changed his mind, because (our advisor thought) our thinking was too rigid. If I had asked more questions about what he was thinking, perhaps he would have invested. 

It was a gut punch. I could see the hole in our balance sheet where that $500k would have been. I could see the list in the cap table where his name would have been.  I looked back at every aspect of the meeting, and couldn’t think of what I would have done differently. But I was ready to change. 

It took almost a year to change. I really, really like being right and the only thing I feel more strongly about is how much I hate being wrong. While there’s nothing inherently wrong with being right (see #4 in Amazon’s Leadership Principles–”Leaders are right–a lot”), I needed a tactic to avoid being a show-off and shift my mindset to being curious. Asking questions was the tactic that worked for me. Perhaps it will work for you as well. 

Finding our content helpful?
We go deeper into such topics on our Podcast - Seed to Sequoia where we speak with investors and successful startup founders.

Need expert advice on building your startup?
We at Silverwood Advisors are committed to supporting Founders in their journey to building successful startups.