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Master the art of thinking big, working small: A conversation with John Cutler

Hello all!

It has been 20 years since the agile manifesto was introduced, and closer to 40 years since software development began moving away from a waterfall-type approach. While many teams have seen great success, others still struggle to reap the full benefits of agile.

To better understand how successful product teams and organizations work, we had a conversation with John Cutler to unpack the art of thinking big and working small.

Read on for key takeaways, watch the full discussion, and stay tuned for more conversations with industry experts on agile and DevOps.


Are you working too big? What have you learned about your customers lately? If you haven’t learned anything in a while, you might be working too big. This might feel “sludgy,” with long stretches of feeling like you’re not making progress.

Are you working too small? How is your work linked to a larger strategy and mission? You probably feel like you’re making progress, but if you look back, you see disjointed, reactive work.

Defining big and working small: Do you have a huge backlog that is already sized? You’ve defined a massive project but merely broken it into smaller pieces. Although you might frequently integrate and reduce risk, there is little room to respond to learning or feedback.

Thinking big, working small: Does your team have a coherent strategy linked to a compelling mission? Think big and work small helps teams recognize the benefits of both! This approach allows teams to think strategically about impact and outcomes beyond the next 3-6 months, and sequence work with the riskiest assumptions first. It also builds in time to experiment, learn, and validate.

Tips for teams:

  • Start with the “why,” not the way. Create a learning backlog, and prioritize what you have to learn.

  • Build shared language. A taxonomy of work helps you better describe different shapes or types of work in your company.

  • Think big, work small is a direction and mindset versus precise guidelines or a checklist to follow.

There were so many great takeaways as we unpacked the art of thinking big and working small; we’d love to hear what resonated with you!

Meet the experts!

John Cutler is the Head of Product Research & Education at Amplitude. As a former UX researcher at AppFolio, a product manager at Zendesk,, AdKeeper, and RichFX, a startup founder, and a product team coach, John has a perspective that spans individual roles, domains, and product. Check out more of John's work & get Amplutude’s North Star framework for free!


Kelly Drozd (me!) I am a Product Marketer at Atlassian and an agile enthusiast. I am passionate about continuous improvement and helping teams work better together. Before starting at Atlassian, I was responsible for leading agile adoption and transformation efforts across Marketing teams at the world's largest children's healthcare charity.





Enjoyed this session, @Kelly Drozd. It was helpful to hear from a seasoned pro like John and I love the think big, work small mindset. Looking forward to seeing more of this series.

Like Kelly Drozd likes this
Kelly Drozd Atlassian Team Mar 01, 2021

Hello there @Peter Preston , I am so glad that you enjoyed it! John is fantastic, such a wealth of knowledge! Thank you for the feedback. 

We are introducing Agile methodology and Trello as a tracking system to our organization.  It was really helpful for me as a new Agile method user to hear all of the information presented by John, including the pros/cons of the different methods.  I look forward to learning more through these articles.

@Tiffany Thibodeau hi! That is so great to hear. I am glad that you found the session helpful. Please feel free to share any other topics that would be of interest to you. Are you primary working with software teams or all teams across your organization (ie business teams like marketing or sales)? 

@Kelly C_ Drozd I am an engineering team member for a consulting engineering company.  We are applying agile to non-software projects, using Trello to track the projects.  This is a very new project management style for the company (less than 6 months), so I am trying to learn as much as possible to be a good team member, and possibly lead project teams in the future.

Kelly Drozd Atlassian Team Mar 04, 2021

@Tiffany Thibodeau That is awesome, thanks for sharing. If you haven’t explored the Agile Coach yet, it’s a great agile resource ( 

Thank you very much for the link @Kelly Drozd 

This was very helpful!

This was helped the person who is like to know and as a beginner start the path.  thank you @Kelly Drozd for your valuable idea to share with us.

We are presenting Agile strategy and Trello as a global positioning framework to our association. It was truly useful for me as another Agile strategy client to hear all of the data introduced by John, including the professionals/cons of the various strategies. I anticipate learning more through these articles.

Kelly Drozd Atlassian Team Oct 16, 2021

@John James that is so great to hear. Thank you for sharing!! 


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