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Having difficult conversations

Practical, concrete methods to help you learn how to talk about the tough stuff

Topic: Career Development
Jeffrey Fredrick
Douglas Squirrel

What could be more dreadful than a difficult conversation? And yet we face potential difficult conversations all the time. Telling the boss that your project is late, proposing a budget increase to a sceptical finance team, or informing your subordinate that her work isn’t meeting expectations—all can be both threatening and consequential. Putting off these conversations is tempting but solves nothing and leaves others in the dark, unable to act to correct problems. On the other hand, diving in without the right preparation can be just as dangerous, leading to misunderstandings, anger, and an even worse mess than you started with.

Google’s recent research on effective teams found that having the “psychological safety” to have difficult conversations is the core attribute of high-performing teams. Although we are often blinded to how we contribute to the problem of difficult conversations, whether through cognitive biases or unhelpful cultural training, the good news is that we have more influence over them than we realize. In return for accepting partial responsibility for when conversations go badly, we open up new opportunities for better outcomes.

In this hands-on course, experts Douglas Squirrel and Jeffrey Fredrick draw on tools and theories from action science to teach you specific, easy-to-apply techniques, such as looking for “triggers” and “tells” in a conversation, that will help you understand how your conversations go wrong and prepare you for more successful results. It really is possible to approach a difficult conversation with calmness and curiosity; join Douglas and Jeffrey to find out how.

APAC friendly time.

What you'll learn-and how you can apply it

  • The common types of difficult conversations and how to recognize them
  • Why mutual learning from a difficult conversation usually benefits all participants and the organization as a whole

And you’ll be able to:

  • Prepare for a difficult conversation to increase the chances that there will be mutual learning and internal commitment to the outcome
  • Define personal “triggers” and “tells” that help you recognize and sidestep common errors in difficult conversations

This training course is for you because...

  • You're a manager who has to give negative feedback to a person you manage.
  • You're a team member at any level who needs to share bad news, for example that you or your team have not completed a project on time.
  • You're a senior manager responsible for firing a subordinate or telling a manager who works for you to do so.


  • Experience in a role that requires difficult conversations (i.e., almost any role besides hermit)
  • Have had at least one recent difficult conversation (useful but not required)

Materials or downloads needed in advance: - Complete the left-hand/right-hand exercise prior to the training

Recommended preparation:

About your instructors

  • Jeffrey Fredrick is internationally recognized for his expertise in software development and has 25 years’ experience as a manager and leader. An early adopter and advocate of agile techniques, he has been a regular speaker, coach, and independent consultant on topics including agile software development, corporate strategy, product management and interaction design. His roles have included VP of Product at software-testing startup Agitar, founder at SaaS startup OpenAvenue, and CTO & Head of Product at recently-acquired fintech startup TIM Group. He co-organizes the CITCON international series of software conferences with hundreds of attendees on five continents.

  • Douglas Squirrel has been coding for forty years and has led software teams for twenty. He uses the power of conversations to create dramatic productivity gains in technology organisations of all sizes. Squirrel’s experience includes growing software teams as a CTO in startups from fintech to e-commerce; consulting on product improvement at over 70 organisations in the UK, US, and Europe; and coaching a wide variety of leaders in improving their conversations, aligning to business goals, and creating productive conflict. He lives in Frogholt, England, in a timber-framed cottage built in the year 1450.


The timeframes are only estimates and may vary according to how the class is progressing

What is a difficult conversation, and why it is a high-leverage activity worth studying? (10 minutes) - Lecture: Delivering bad news; providing negative feedback; firing; requesting help; reframing these conversations as opportunities

Coherence busting (30 minutes)

  • Lecture: Coherence busting
  • Hands-on exercise: Use coherence busting in a few realistic scenarios, generating a collective list of alternative explanations for observed behavior
  • Q&A

Break (10 minutes)

Left-hand/right-hand analysis (30 minutes)

  • Lecture: Left-hand/right-hand analysis introduction; how to identify "triggers" in your own thinking and speech that you can use to remind yourself to inquire and learn rather than act defensively; how to identify "tells” from the other party that are indicate there are opportunities for further learning
  • Hands-on exercise: In groups of four, roleplay an example conversation and attempt to use triggers and tells to guide the conversation toward learning rather than defensiveness

Wrap-up and Q&A (10 minutes)