4 min read

On asking the uncomfortable questions

On asking the uncomfortable questions

Today I was listening to Masters of Scale podcast, episode 93, where Reid Hoffman was interviewing Michale Siebel on asking the uncomfortable questions. You know, the ones that all of us have been avoiding every now and then, but which are of crucial importance for progress.

Why is this essential right now?

Of the many things you could do at this moment, why is it important to do that very specific thing? As an early-stage founder, you'll likely have a long to-execute list, for more than 24hrs of work per day. Thus, the essential is to pick and prioritise the right things, the ones that you'd have to do right now.

A related question for this is also

Can you do it also later?

For example, you don't need 100+ features right away in your app. Or support numerous formats. Many great products were actually very basic and simple in the beginning. I recall the story heard at (Transfer)Wise hackathon, how in the early days first transactions happened with just using emails and one Excel sheet.  Michael suggested that you should

Do the thing you can't never do again.

For him for example it was the moment when his friend invited him to join the startup. It's something that doesn't happen every day. I feel that it's also a bit linked to the Regret Minimization Framework of Jeff Bezos. Basically looking into the future and looking at your decision from that perspective.

I recall quite a number of moments in my life, where opportunities came across, which would happen once in a lifetime. In my travels, for example, fare mistakes classify here as well. But also on the business side, for example. When I was invited to create the first-ever Estonian Climate Change Adaptation Strategy, I knew that it just happens once. Or joining Antler in Singapore for their very first cohort programme. These things happen only once.

Are you solving a personal problem?

I still remember the session with Tyler Norwood during the Antler programme, where he presented "A framework for creating and testing new business". He suggested picking a problem to solve, which is either your personal problem and which you know well or if you pick a problem, which is not your personal one, then you should know it so well that you'd be able to publish 5 books about it.

For example, at Nursebeam, we're doing travel health chatbots. I've been travelling to over 90 countries and every now and then got ill in some of them. And it was always a hassle. A very unpleasant one. Seeing that insurers were not really improving my experience, I decided to do something about it and found other people who had experienced similar issues.

Once you're picked the appropriate problem and working on a solution for solving it, then Michael suggested to ask:

Not only if it is working now, but will this continue to work and will scale down the road?

Some solutions are like one-off customised solutions. But can your solution help also others, besides you? One-off consultation with a doctor helps one patient. Taking the know-how of the doctor and coding it into a chatbot could help thousands or millions. That's why also software has the edge in the innovations these days, enabling you to help more people, at scale.

Reid and Michael also both admitted that

It's very easy to overlook the most important question.

So, how should you avoid those overlooks? Building the right network around you is the key. They'd help to identify the risks you might have, from perspectives that you do not. And Michale suggested that it is better to talk to users instead of investors. He sees investors and customers like 2 different, unrelated species. Of course, both are needed for your ecosystem, but you really need to nail it with the wants of the users/customers.

Asking the right questions is an art

You need the right questions, at the right time. And if you don't have those questions at bay, then that network around you should ask from you. Michael sees himself as a kind of therapist by asking those questions from the founders at YC cohorts, to break the stuck chains in thinking, to get wheels running again. And so far it seems that the art of asking questions remains in the human domain. As Picasso said, "Computers are useless, they give you only answers." Thus, develop your skill to ask questions and that your network around you would ask questions as well, from you.

But what if you get problems and are unable to solve them? Michael said that there are 3 frequent false understandings he sees often:

Frequent Founders' False understandings at YCombinator:
1. Money will solve your problems
2. Employees will solve your problems
3. Smart investors will solve your problems

It still boils down to asking the right questions, often the uncomfortable ones. Michael also mentioned that #1 company killer is the company building.
Scaling too early is almost always fatal. Scaling late is not. And when scaling, hire the people who ask questions. And help you to find the customers.

And should you really fail, then Michael suggested framing it as  

If  I fail, can I fail in an interesting way that we could all learn from it?

And while this might sound complicated, you might ask

Should I be a founder?

Yes, if you have some type of irrational motivation. What is our deep source of motivation that keeps you even in the darkest times? That's something you can think of now. Also if you're interested in listening to the whole episode yourself you can do that at:

Photo of the post by Emily Morter on Unsplash