top of page
  • Writer's pictureYannick Oswald

Asking the right questions

Updated: Dec 19, 2021

A couple of weeks ago, I attended an improv comedy show in Paris. I am always amazed by how these comedians come up with hilarious stories on the spot. So, while I had planned to publish another more technical post like last time, I thought: 'Nah, let’s write about something more ‘out of the box’… Creativity'.

What does it mean to be creative. Should entrepreneurs have that skill?

First off, anyone can be creative. After Einstein’s death, doctors took his brain to analyze it. It was preserved and sliced up. Scientists obsessively studied every winkle, looking for some feature that could explain how he came up with all of those revolutionary ideas. But there was nothing special about the brain...

Creativity is more like a muscle and way of thinking that can be trained. It emerges when two different regions talk to each other: the default mode network (our subconscious, active when we let our minds wander...), and the executive network (our focused thinking mode, that filters everything coming from our default mode with pre-conceived frameworks). These frameworks could be more business-focused, more art-focused, etc., and are influenced by our culture, life stage, etc. The executive mode should filter rubbish ideas coming from our subconscious from the interesting ones. In the brains of highly creative people, these two networks are very connected. For most people, though, the executive mode is in control, often too much. Many great ideas just don’t get through...

The superpower of great investors is to spark out-of-the-box thinking, the creativity of founders. The legendary music producer Brian Eno, who worked with the likes of Coldplay, David Bowie, U2, etc., explains it well: The creative process is like gardening, not architecture. ‘You are planting something. You need to watch how it grows, rather than trying to completely constrain it and know every detail of it.’ He tried to disrupt structured and pre-conceived thinking patterns by randomly picking words and phrases out of a set of note cards and applying them to their creations. This forced artists to think entirely outside the box and create new thought flows.

‘Yes, and…’

Performing an improv show, as is any creative process, is such an evolving process. Shows usually start off with a simple idea, often a suggestion, either from the audience or another comedian. And, based just on that, the actors make up a scene. For most people, this is a terrifying exercise. And, even the most creative people, often just come up with dull, obvious stuff. But they just need to nail it once or twice during a show to get the ball rolling. And that's exactly the point...

Embrace whatever your product users send your way, and then build on it. The most specific, helpful clues for the improvisers often do not come from the audience but from other performers. You need to listen to what your teammates have to say. You have to constantly adapt. That makes the best characters. Improv’s mantra is ‘yes, and…’ Improvs always start with a basic scene, then you add to it. The executive network then checks in with your audience. You analyze and go with the flow. Often they don’t respond well, of course… but that’s part of the process. Even the best comedians get stuck. You just need to be ready to fail, because you mostly fail. As with building products, you just have to iterate fast until you hit it right a couple of times.

Creativity is one of the superpowers of entrepreneurs.

As an early-stage founder, you have a goal. It is based on a hypothesis and a strategy with proximate objectives to get there. Only then you can turn to budgeting and let your executive network take over. I coined this early-stage startup strategy setting 'The Startup Jiujitsu'. But the ways to reach your goal change constantly. You just don't know what might come next. You need to be creative. It is easy to get stuck when your head is down, executing at full speed.

It is a bit like writing a blog post. Once I defined a topic (diagnosis), I research some ideas (market research or guiding policy). Then I hit the 'create draft' button and start writing (product testing with coherent actions). Most ideas don't stick. I go back and test another flow. Besides the overall topic, the final outcome often has nothing, or not much at least, to do with my initial content skeleton. As in stand-up comedy, you have to let your mind wander until you find a great fit. I then check in with the audience (readers). Some posts are more popular than others. I try to figure out why and apply my learnings to the next ones.

For VCs, it is all about asking the right questions.

Famed VC Don Valentine once said, “VC is all about figuring out which questions are the right questions to ask". Having been now on the board of 10+ companies, I can confirm... Let’s take an example. Imagine you ask someone: 'Say things that are green'. The most obvious stuff that comes to mind are things like green grass, trees, or frogs. But, if you give people a cue, let’s say: 'Name all the green things in Paris at the turn of the century'; that’s going to activate other neural networks, and you may start thinking of stuff like absinthe, the chemicals in the Curie Lab, etc. It is the same principle as Eno’s notecards: An outside-the-box prompt challenges the mind to explore less visited neighborhoods, to disrupt the patterns...

Great questions raise an issue and force everyone in the room to think differently. Many people and companies do things right but don’t do the right thing. Taking the observation one step further, doing the right thing the wrong way can actually result in something meaningful, whereas doing the wrong thing the right way rarely does... So that begs the question, 'what should we work on?': Is this the right go-to-market, does this feature have the biggest possible impact, why don’t we consider these data points in more detail, etc.? Many entrepreneurs ask for help in figuring out what to work on. VCs can’t tell them what to work on. That has to come from within. But VCs should be there to help you figure it out.

Secondly, it is crucial to check in ‘with the audience’, observe their questions, and suggest answers to them if the group is stuck: ‘Why don’t you try this?’, ‘I think we should raise money now...’, ‘this could be an interesting business opportunity for us’, etc. Great VCs need to read situations, the big picture, and make sure entrepreneurs don't miss an opportunity or challenge. It is a tricky exercise. Only if they have conviction on a specific topic, should it be brought up. Things happen so fast in startup land, and timing is everything. Let's make sure we don't miss it.

The 'ask the right questions' skill is crucial, also before investing in a company and sitting on its board... In today’s 'heated' venture market (it still is, right? 🤨), it is more important than ever to determine the right questions to drive conviction into your own investment process. There are two types of due diligence processes: 'Information gathering' and 'Conviction building'. ‘Information gathering' is asking founders for every piece of possible data. But, at the early stage, data is limited and can only do so much, of course… 'Conviction building' is very different. Conviction building starts with a plan on 'why to invest'. It boils down to figuring out the key business drivers, if they are doing well, and if they can increase dramatically in the future. To detect these business drivers, you need to ask the right questions. Conviction Builders drive to the heart of what matters - they don’t ask all the questions, they ask the right ones. I suggest that entrepreneurs make sure they know what type of partner they want before closing an investment with a firm. They also need to make sure to provide the right answers to the questions asked. A wrong answer can often turn the tide in a due diligence process…

I was in Helsinki for a tech conference last week (thanks to my friend Daniel from Next 47 for hosting), and then spent some days in Vilnius and London, before going back to Paris. Here a pic from frosty (-10°C) but beautiful Finland...

Life is awesome,


Other content I have found useful

- Big news from our company 'The Bank of London' and its brilliant founder Anthony Watson. After 4 years in stealth, ‘UK clearing bank set to launch with $1bn valuation…’ Grateful to have been the first firm to back this rocketship…

- More news from our portfolio: Receeve, the digital debt recovery and collection platform, takes total funding to $16M...

- A great intro by Fabrice on crypto space 'What’s the deal with crypto?' including great analogies with the internet infrastructure in general.

- One of the best tweets I have come across in a while. Brilliant data points on the valuation of tech companies that went public between 2010 and 2019. The median valuation is $4.4B. Great to get some perspective from time to time...

- Great read on the evolution of SaaS businesses and business models, from pure subscription plays to embedding more and more financial services on top.

- A interesting overview of the tech world and its latest trends by Benedict Evans. Definitely worth a read.

- It is happening...: 'Gig economy stocks plunge amid EU regulatory crackdown fears': Speculation that the European Commission is set to propose stricter labor rules to regulate the gig economy have sent shares of companies in the sector sharply lower again on Monday building on losses from last week.


New feature! You can now leave your comments below each post. Share them with the OE community.

  • Grey Instagram Icon
  • twitter
bottom of page