Ask the questions you should be asking

I just read the following quote in a post by Jon Parrish a now successful entrepreneur about pitfalls that founders fall into:

Entrepreneurs (myself included) have this incredible ability to ignore reality when it isn’t in line with our goals. We feel threatened by the idea that the answers to the questions we should be asking may prevent us from moving forward, so we don’t ask them. Or worse, we ask the questions but don’t listen to the answers. It’s self-deception in the worst way, and it’s an entrepreneur’s Achilles’ heel. It feels better to move forward blindly than to search out whatever hurdles may be in the way.

But closing your eyes doesn’t make monsters go away. The answers exist, whether you want to face them or not.

We see this all the time, and what’s interesting is that it’s the flip-side of a very positive entrepreneur character trait – belief in a positive outcome.

On Tuesday I had lunch with a friend who had just been to Tony Robbins’ Unleash the power within four day seminar. He described how Tony inspires people by getting them to visualise success. When the mind believes that something will happen we act accordingly and that gives us a much better chance of getting there. We’ve all seen the reverse too – when someone doesn’t really believe that success is possible so they tackle a problem half-heartedly thereby making failure a near certainty.

A lot of entrepreneurs naturally find energy from an unwavering belief that they will succeed (I wrote about this previously as one of the four cognitive biases of successful people). The reason that some of them feel threatened by asking questions is a fear that the answers might undermine that belief.

It’s a tricky one, because the questions need to be asked and the self-belief needs to be maintained. If you are struggling with this, then the answer, I think, is to root the belief in yourself and your ability to overcome challenges, not in any given strategy or view of the world. Otherwise your self-confidence will always be fragile.


  • Really interesting post, Nick.
    Asking good questions is definitely a skill in itself.
    In your experience, do you sometimes see founders who begin their journey with curiosity and an open mind in order to soak up information and either validate or disprove their assumptions, but over time become less inquisitive as they become more sure of themselves (perhaps because they feel like they already have questions/assumptions figured out)? How do you combat this to ensure founders maintain a healthy skepticism?

  • Hi Andy – yes, founders often become less open to questioning their assumptions over time. We have a rule of thumb that if an assumption isn’t tested within a couple of weeks then it gets baked in to the plan and testing it becomes emotionally challenging.

    One of the skills in the investor toolkit is to be able to constructively point out when this is happening. The business model canvas is a good tool.
    It isn’t always easy.


  • Ah interesting. Easy to see how an impartial opinion from a trusted mentor/investor can be beneficial in this scenario. Thanks for answering.

  • Very good point.
    I’ve also seen cases where that fear builds self-confidence during the journey. The entrepreneur uses it to push her/his own limits. In this case, when the startup fails, it becomes very liberating because she/he will look back at the ride as an experiment gone wrong. Not easy for all of us though…

  • Chris Turner

    Great point! It has been said that the quality of our life is determined by the quality of the questions we ask ourselves on consistent basis. If we ask lousy questions, we’ll get lousy results. I love learning from Tony Robbins and I’m one of the attendees of his UPW event in London I got one of those little sticky notes that say Questions = Results 🙂

  • 🙂 Thanks Chris

  • Mike Jones

    Great post Nick. I’m not quite sure how I dug this one out from so long ago but it’s certainly a post that gets you thinking about the whole ‘the secret’ law of attraction thing. I’m a strong believer of you are what you think. I’ll be attending UPW in London this coming April and I can’t actually wait.
    Prices are going up by £300 shortly so get stuck in!~