Around a year ago, I started speaking with many founders and early-stage start-up employees to get their advice on transitioning from consulting into the start-up world. Whilst I spent some time up-front thinking about what I wanted to get out of these conversations, I now realise that through mediocre questions I was not maximising the value of these discussions.
The result? Lots of differing opinions which swayed me to-and-throw between various stances on the questions I was pondering. I would convince myself of one thing and then quickly change my mind based on new input.
As an example, I have now asked many founders: “Would it be wiser to first join an early-stage startup before starting a company of my own?”. Unsurprisingly, I have heard every possible response. Largely, those who took that route vouch for it and those who didn’t do not. As I recently discussed with a friend, the universe of possible ways to build a successful organisation is so vast and serendipitous that trying to understand and replicate an individual’s path to success just doesn’t make sense.
Quality questions create a quality life.
Tony Robbins
Improving the questions I am asking.
When trying to learn from people in general, the north star should be to understand how they think and what their thought process is… it is about understanding the why. If we can tap into that, we can then refine our mental models of the world and apply relevant principles to our own situation to land on the best decision given our own unique circumstance. I’m learning that the more we lean on people’s opinions, the higher risk of adding unhelpful noise.
Here are some questions I have asked over the last few months and upon reflection what a better question would have been:
| Typical questions I have asked | A better version of the same question |
| Do you think it would be better to join a startup before beginning something of my own? | What was your thought process in deciding whether or not you were ready to start a business of your own? |
| I’m thinking of writing a blog about X. What are your thoughts on this? | Are there any blogs or podcasts that you find exceptional, and if so what do they do a really good job of? |
| I feel like I should be doing something that draws upon [AI/Blockchain etc.]. What’s your opinion on this? | How did you decide which domain or space to play in and do you think this was the right decision? |
| I am trying to find problems that are an extension of my interests and specific knowledge. Do you think that’s the right approach? | How did you know when you found the right problem to solve? |
| I’m thinking about starting a funding vehicle to help early stage founders from [Company X], what do you think? | As an angel investor, what are the biggest pain points you face in finding and investing in good companies? |
Through lack of discipline, I’d often resort to questions of the form: I’m thinking about doing X, what do you think?
The right-hand set of questions are more intellectually expensive and give a less direct route to the desired answer, but they are superior for several reasons:
- They move the focus away from you and onto the other person, which typically is a much better tool for driving engagement.
- They help reveal the underlying thought processes which may or may not be relevant to our own situation.
- They suppress ego and avoid the ‘seeking of validation’ for our ideas.
- We’re less likely to just receive someone’s opinion, which unless they are an expert, can easily be unhelpful.
- There is an undertone of validation seeking in the LHS questions which evokes a lack of conviction and insecurity.
Other pit-falls that many of us are guilty of.
In addition to moving away from ‘opinion-based’ to ‘thought process-based’ questions, there are some other bad habits that I’ve noticed myself slipping into from time to time that are worth highlighting:
- Asking the same question to many different people without having a structured way of reflecting on the findings / insights.
- Allowing your ‘need’ to speak to more people become a form of procrastination that stops you from just getting going and taking action.
- Asking questions where you probably already know what the answer is going to be.
- Asking questions where you don’t really care about the answer (for example, just because you think it’s a ‘smart sounding question’)
- Focusing so much on what you want to ask that you don’t fully listen and engage with the person’s responses.
- Listening to advice from people who haven’t actually done the thing they are advising on (see below…)
When trying to learn from others, spending time to plan the right questions is important.
The quality of your source matters.
When making decisions it can be easy to try and gather as much data as possible to inform our choices. What we can easily overlook is that one or two very high quality sources can prove significantly more beneficial than a multitude of half-baked inputs.
Invest the time up-front in figuring out who you want to source learnings from before trying to speak to anyone and everyone that has some connection to what you’re exploring.
Case in point: I am currently in the process of moving to a new country to live and work for at least the next 6 months. It’s a pretty big decision, likely a life-altering one.
For several weeks I was speaking to a number of people I knew who had some connection to the place I was considering (Lyon). Input was varied, but nonetheless I was weighting a lot of the signals pretty heavily despite some of these people only having visited Lyon for a day or two. I finally came across someone in a very similar position to myself who had lived in Lyon for several years, as well as 9 other cities in Europe. He immediately could speak at length about both pros and cons, providing intimate details that resolved much of the uncertainty in my head and made my decision clear.
In hindsight it’s obvious that I should have sought out this kind of profile, and yet I instead opted for the path of least resistance which was to lean on input from people within my immediate circles. Quality of the source matters!
Stillness & Scale 