27–29 September 2017, Churchill College, Cambridge

From Bitter to Better: Harnessing Pessimism to Improve Projects and Lives

A 60 minute Case Study by:

Caitlin Cleveland

Big Nerd Ranch

About this Case Study

We constantly hear about the virtues of optimism, both at work and in our private lives. We believe that having a positive outlook and finding the silver lining is vital for success, while pessimism is seen as negative, or even damaging to our teams and projects. But what if pessimism isn’t all bad?

In this surprisingly sunny session, I will talk about the science behind the ways pessimism really can be useful to us in our work lives, and how I learned to apply it to achieve better project outcomes, happier teams and more satisfied clients. I walk through my journey to becoming a ‘happy pessimist’, where my pessimism is a tool that both my projects and teams benefit from.

This entertaining case study will include summaries of studies showing the benefits of practising pessimism, as well as practical examples showing how to use strategic doses of pessimism without driving your optimist teammates crazy.

Some of the topics covered in these examples include:

  • providing a counter-balance to the over-optimism that can lead to avoidable pitfalls in development
  • catching instances of over-promising in sprints and projects before they happen, without being seen as ‘the negative voice in the room’
  • saying this instead of that - phrases for saying ‘no’ and providing a voice of realism to help guide your team
  • earning more trust from your team members and clients when bad news has to be given or things go wrong

About the Speaker

Caitlin is an agile project manager working in tech who is fascinated by how things work. Her focus is working with distributed and local teams on app and web development projects across a range of industries. Variety is the spice of life and her projects have plenty. She is especially interested making the different pieces of organisations work better together by applying agile lessons to company operations. When she’s not helping teams work better together, Caitlin can be found outdoors - whether she’s hiking, kayaking, or even doing a bit of camping.


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