In one sentence: Analyse a startup business back and front, top and bottom.


  • Create clarity for the startup team regarding the business idea;
  • Voice and address any hard realities and challenges; and
  • Define best next steps.

This is the type of process I wish I had when I set up my first startup. We had a great idea, a solid team but there were a host of pitfalls and blind spots that we really weren’t willing to stare down. This process looks to split out the inevitable emotions coursing through the veins of any startup team from the facts and hard realities. Wishful thinking is an almost inevitable pitfall especially as team members are emotionally and financially invested in the business. It can be hard to be objective and address uncomfortable questions such as:

  • Is the business model solid?
  • Do we have the right team?
  • Are we implementing the model in the best way?
  • What are our blind spots?

So the invitation is to take the time to step off the treadmill and see what you might learn as you slow down and shift perspective.

Nurturing Curiosity – Daily Practice: This is part of the Nurturing Curiosity series of tools, insights and questions designed to help nurture curiosity as part of our daily practice. In point of fact, every interaction we have is an opportunity to question what we are observing and how we and others are seeing the world. Also remember that questions come in many forms throughout our day. Startups are unusual environments. In order to defy the odds, it is often necessary for the founders to defy reality and become somewhat fanatical about the business.

This makes perfect sense in those early days – they need to transmit belief because if they don’t believe in their baby, who will? And yet, this can become a real challenge when the business moves beyond the start-up stage and starts to scale. At this point a new mindset is required. In ways, founders need to continually ask themselves How might I be holding the business back? Who does the business need me to become? Am I the right person to make this journey?

About Tom O’Leary

My mission is to help others think differently – meaning more broadly and deeply – and thereby make better decisions. The key to thinking differently lies in our curiosity.

The more we question, the more possible answers we uncover, and the more we expand what we thought possible. Life has taught me that possibility lies not so much in seeking answers but in learning to ask better questions – the ones that help prioritise what is truly essential.

And yet, in a culture obsessed with efficiency and productivity, the paradox is that much energy and resources are wasted by a bias towards action over contemplation. If you are answering the wrong question, it doesn’t matter how ‘hard’ you work, you are still answering the wrong question.

That is why I am a big advocate of nurturing curiosity and innovative thinking at all ages, particularly amongst leaders because of the impact they have on us all. In my vision, leaders aren’t boxed in by traditional thinking or established playbooks. They are curious, open to fresh ideas and diverse perspectives, fostering a culture of exploration and learning.

How Might Tom Help?

  1. My first invitation is to take maximum advantage of the free content on this site, including signing up for my newsletter.
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