Debugging Difficult Conversations (Free)

Navigating Difficult Conversations

This course aims to enhance your success in your personal and professional life by improving your ability to navigate difficult conversations. The core belief underpinning the course is that our lives, filled with challenges and difficult circumstances, can greatly benefit from engaging with rather than avoiding these tough interactions.

We will explore the idea that preparing for these conversations, planning them out in advance, and entering them with a productive mindset can make them both effective and beneficial. This course will walk you through different types of difficult conversations you might encounter, both in leadership roles and as a member of a project team.

The Importance of Difficult Conversations

Delaying or avoiding difficult conversations may lead to unresolved issues which can compound over time, similar to ignoring a mechanical issue with a vehicle until it becomes irreparable. The longer we delay these conversations, the more challenging and costly they become to resolve in terms of time and trust.

Contrary to common perception, handling difficult conversations early can build trust and respect with your team. This course will provide the tools and insights needed to approach these discussions confidently, knowing that they can serve as a catalyst for better outcomes, building respect and trust, and ultimately leading to the success of your projects, team, or business.

Approaching Difficult Conversations

While difficult conversations are always challenging, the goal is not to make them comfortable, but rather to build confidence in approaching them.

There are three main ways to approach difficult conversations: ignoring them, charging headlong into them, or preparing and entering them thoughtfully. This course is about the third approach, aimed at fostering the confidence needed to reduce fear, stress, and anxiety.

We split the approach to difficult conversations into two main parts: mindset and preparation. Mindset focuses on adjusting your perspective towards these discussions, viewing them in a positive light, and understanding their significance for you, the person you’re engaging with, and the team or company. Preparation is about gathering necessary data, logistics, and operational aspects to support the conversation.

Mindset for Difficult Conversations

To foster the right mindset, we suggest you ask the following questions before entering a difficult conversation:

  • Why is it in my own best interests to have this difficult conversation?
  • Why is it in the other person’s best interests that I have this conversation with them?
  • What are the benefits to the team, the project, the company from this conversation?
  • What are the negative consequences if I don’t have this difficult conversation?

Reflecting on these questions can help shift your mindset towards the positive outcomes of the conversation, even if the discussion itself might be uncomfortable or challenging.

Preparation for Difficult Conversations

Once you’re in the right place with your mindset, you can move on to preparing for the difficult conversation. Planning for the conversation is going to mean that you will be able to handle more situations when they arise.

Preparation can take many forms:

  • Gathering data to back up any claims,
  • Gaining outside opinions to ensure you have the right viewpoint,
  • Thinking through possible objections that could be raised and how to overcome them,
  • And, having multiple plans depending on how the difficult conversation evolves.

Each of these has value in every difficult conversation, but their relative weight will depend on context.

The Difficult Conversations Worksheet

This document guides you through the understanding of difficult conversations and prepares you mentally for approaching such situations. This guide can serve as a reference point whenever you anticipate daunting discussions.

Page 1: The Difficult Conversation

This page prompts you to clearly define what the difficult conversation is about and how to approach it. It helps organise your thoughts and visualise the conversation and the people involved. It encourages you to describe the conversation neutrally to minimise emotional reactions and better manage emotions.

  • The first part helps you understand the essence of the difficult conversation. This section aids you to state clearly what the conversation is about and you can use it to carefully align your thoughts.
  • The second part, labelled “Who”, will assist you in identifying relevant participants. Avoid involving too many people, but ensure critical individuals are present.
  • A crucial point to consider is the timing; settling for an optimal time, usually not late in the day or on a Friday, can shape the outcome significantly.
  • The location of the conversation can influence the tone and defence level of the participants; hence, choosing an appropriate location is paramount.

Page 2: The Mindset

This page contains questions to help you understand the benefits of having the conversation for everyone involved. Spend time reflecting on multiple answers to these questions. Remember that choosing not to have the conversation can have its implications, which are outlined in the final question of this section.

This section helps you to understand the benefits associated with having the conversation for all parties involved. It encourages thoughtful reflection and emphasizes the consequences of not having the discussion.

Page 3: The Preparation

The final page assists you in preparing for the conversation. It guides you in gathering necessary data, understanding the situation, anticipating possible objections, and planning for different conversation paths. It serves as a tool to jog your memory and think through various outcomes.

This portion equips you with the tools to adequately prepare for the conversation. It guides you on how to collect all required data, understand the situation, foresee potential objections, and chart different conversation paths. The preparation stage provides robust support during the conversation.


This guide is a valuable tool for approaching difficult conversations. Whether you print it off or use it online, spend at least 10 minutes going through it before any challenging conversation. It will help you navigate the discussion more effectively and compassionately.

Use this guide whenever a difficult conversation arises; it serves as an aid to jog your memory and consider different conversation pathways.

Worksheet Example: Performance Conversation with Jonathan

This case presents a junior colleague named Jonathan who was observed playing with his phone during a client meeting, indicating disengagement. The client later reported this behaviour confidentially.


In a client meeting, Jonathan was noticed to be more interested in his phone than in the discussion. This behaviour led to missed vital information and gave the client an impression of disinterest and lack of commitment to the project.

Who and When?

The feedback discussion should be a one-on-one interaction between the observer and Jonathan, happening as soon as possible after the incident to maintain the recency of the event.


Given the sensitivity of the feedback, it should occur in a private setting to avoid unnecessary discomfort or embarrassment.


The reasons for this feedback session are multifaceted:

  • The observer felt uncomfortable witnessing Jonathan’s behaviour.
  • The observer has to manage client concerns.
  • The organisation could potentially lose a deal due to Jonathan’s perceived lack of seriousness.
  • Jonathan, being early in his career, needs to understand professional etiquette for his growth.
  • Jonathan needs to recognise the potential negative impression he could create with the client.
  • The team should understand that no one is exempt from feedback.
  • The potential impact on the project if the client is upset.


In this scenario, preparation involves timely execution to ensure fresh memories and minimal need for supporting evidence. Additional opinions from a coach and a peer were sought to ensure the validity of the observer’s perspective.

In conclusion, when we approach feedback from the perspective of benefiting the recipient, it becomes less of a challenging conversation and more of a means for growth and improvement.

Worksheet Example: Running late on a product

Understanding Project Delays

Everyone experiences project delays. It’s a common concern that makes us uneasy because we often worry that it reflects negatively on our individual performance. It’s essential to understand that project estimates, targets, and deadlines aren’t about individual performance. They exist for coordination, timeline assessment, and validating past decisions.

Benefits of Discussing Delays

Discussing delays with project managers and colleagues benefits everyone involved:

  • It allows you to work on more interesting problems.
  • It shows your proactiveness, helping you build trust with the project manager.
  • It allows the project manager to make informed decisions based on the correct assumptions.
  • It helps unblock other team members who might be waiting on your tasks.
  • It contributes to a trust-based, open working environment.

Dealing with Delays: Example Worksheet

This worksheet provides an example scenario of running late on a ticket and shows you how to break down the situation, who should be involved in the discussion, when and where to have the conversation, and the mindset to maintain:

  • What: I’m running late on a ticket that was estimated to take two days, but has taken four days.
  • Who: The people involved should include myself, the project manager, and the senior colleague.
  • When: The discussion should take place as soon as possible.
  • Where: While the delay can be mentioned in a stand-up, a more detailed discussion should occur in a private meeting.


Targets, deadlines, schedules, and ticket sizes are not tools for performance assessment but for coordination, estimating timelines, and revisiting past decisions. When discussing delays, remember that your intent should not be to defend your performance but to evaluate how this impacts the project and the steps you’ve taken to reduce the impact. Below are some mindset statements that can help:

  • The problem is small now, so the conversation won’t be hard.
  • Delaying the conversation will make it increasingly difficult.
  • Everyone encounters unexpected obstacles. This is not a reflection of my performance.
  • If I address it now, it’ll go a lot smoother.

From a self-centred perspective, addressing the delay allows you to tackle more interesting problems and unblocks your team members, benefiting everyone involved.

Preparation for the Conversation

Preparing for this difficult conversation involves gathering data and information. Here are some questions to ask yourself and get answers to before having this conversation:

  • What were the blockers? Why were you delayed?
  • What do you know now that you didn’t know before you started the work?
  • How long will it take to finish the work?
  • If you don’t know how long the work will take, what information can you gather to estimate it?

It’s important to be honest in these conversations. If you don’t know something, it’s better to admit it and discuss how you plan to acquire that information. Your goal is to build trust and give accurate information, so avoid making things up.

The goal is to understand the risks to the timeline and what you can do to mitigate them. Preparing for these conversations makes them smoother and makes the project manager’s job easier.