Difficult Conversations on Projects: How to get them right

If you want to consistently deliver powerful projects, difficult conversations are a fact of project life.

Making the mindset shift is the first step. But once you’ve reframed having difficult conversations, you still need to have them.

And that requires some practical skills.

Let’s look at the dos and don’ts of difficult conversations so you can successfully use a direct approach when addressing issues on your project.

What you shouldn’t do during difficult project conversations

Before we look at actions you can take to improve your chances of having more productive and less uncomfortable conversations, let’s look at things I would not recommend you do.

The thing that links all these don’ts together, is that they are tactics we use to avoid actually having the critical conversations we need to have in order to resolve a project issue.

DON’T Introduce new accountability tools without having the important conversation first

The most common thing I see when teams are trying to have conversations to resolve issues related with role disputes, is that they will introduce a RACI matrix.

On its own, a RACI matrix is a terrific tool for defining responsibility and accountability on each project.

But, if you’re using it or any other project resource template to overcome or avoid critical conversations, this will not fix or solve the underlying problem that is at play.

All it will do is cause the people you’re setting it up for to feel more anxious, because they will sense you are avoiding a conversation. Which in turn makes the situation more awkward.

So absolutely use a RACI matrix (or any other project guidance template). But only AFTER the information that should go into it has been discussed, considered, and agreed to.

It’s equally important that the process involves the entire project team, and in particular the people surrounding the problem you are trying to solve.

DON’T Make it someone else’s problem

A softer approach to directly addressing a particular person we believe to be causing the problem, is to tell their colleague about the troubles we’re having.

We do this in the hope that they will share the burden and possibly positively influence the problem person.

At times we go as far as asking others to take on more of the problem person’s responsibilities without completely discussing it with the person who is causing the issue.

This won’t help resolve your situation.

All it does is put more work on other team members, often causing bottlenecks to project delivery as well as jeopardising team relationships by ostracising team members.

DON’T Micro-manage

How When someone on the team is not playing as a team and we have chosen not to have an initial conversation with them, there is a tendency to start ‘keeping an eye on them’ to make sure things don’t get worse.

This mode of management very quickly turns into micro-managing. Micro-managing is the opposite to cultivating trust and empowerment on the team.

When there is already an underlying problem, micro-managing causes the team to become less trusting and more anxious.

DON’T Take away responsibility

Typically, when there’s a problem with a certain team member (in particular, if they have done something they shouldn’t have) it becomes a natural progression to take certain responsibilities away.

This is not necessarily a bad thing, but it is all about context.

If responsibility has been taken away from someone without expectations around the responsibility being clear to begin with, and it was done without a thorough warning or explanation then, it will reduce trust, cause disengagement and create more anxiety.

What you shouldn’t do during difficult project conversations

DO Reframe – It’s not good or bad, it just is

When you need to address a situation requiring a conversation don’t look at it as a position or negative activity.

Just like so many other activities you need to perform on a project, addressing an issue is just another activity.

Sure, it can turn out to become uncomfortable but that is not your aim. And it definitely shouldn’t be your state of mind when you are planning out the actions you will take.

DO Set expectations and intention

Ideally the team would have set the expectations of how they work at the beginning of the project.

These ground rules will guide you to the best way to address team issues when they come up.

However, if this hasn’t been done and you are now needing to address an issue, it is important to set the intention and expectations of the conversation you will (or need to) have.

Remember, this conversation should never be intended as a personal attack but instead an opportunity to discover what you, the team and external stakeholders need or want to allow so you can make continuous progress to deliver on the projects why.

Let’s look at the example of someone who needs to have their responsibilities shared but doesn’t want to let go of the reigns.

  • Why is there a need for their responsibility to be shared?

In this case it may be that stakeholder updates are being missed because the person has too much on their plate causing a reduction in stakeholder engagement and confidence.

  • What needs to be achieved by sharing their responsibility?

Lorem confidence to continue to fund the project.

  • What tangible actions are you expecting from the person or people in this conversation?

Email to stakeholders informing them of the change in responsibility and why, and who will be communicating with them, as of when.

An email invite to the new owner of stakeholder engagement to all stakeholder meetings by an agreed date.

To learn more about setting team expectations check out my article The 5 Steps to Creating Great Project Team Chemistry.

DO Provide clarity

Clarity drives cohesion! So be clear on what you need to achieve and how the problem is affecting the needs of the project.

Here are some questions you can ask for structuring your conversation to drive clarity.

  • What has caused the need for this conversation? Was there a particular incident, a complaint, a failure somewhere, etc? 

If there have been previous conversations or strategies which have been tried before to overcome this problem, review what was tried. What proof do you have that they haven’t worked?

  • Why you think this person or group of people are adding or creating the problem? Remember this is NOT a personal attack so make sure the information is delivered with tangible examples not hearsay. And if you don’t have any then perhaps re-think having a conversation.
  • What is the outcome needed from this conversation? Is it agreement, or a proposal for consideration, or a solution, etc?
  • What needs to happen in this meeting? Keep it constructive so there is no room for “he says she says”. Is it workshopping a solution, or providing an explanation or instructions on how things will work going forward, or an opportunity to address concerns of all parties involved and suggestions on constructive course of action?
  • What is expected to happen after this meeting? Make sure all outcomes are measurable. For example, a RACI workshop involving the entire team to be held to discuss and agree on the team’s responsibility and accountability on the project. Final RACI matrix to be emailed to project leadership with entire team cc’d.

DO Create boundaries with penalties

Boundaries within the conversation

This applies to both in the conversation you have as well as the agreed course of action or outcome following the conversation.

  • No personal attacks
  • Providing context for the conversation. Does the conversation relate to the entire project or just a specific area? If the conversation is a negative one about someone’s performance for example, ensure you don’t rob them of all the good things they are doing while trying to highlight an area for improvement.
  • What are non-negotiables vs things that are open for discussion and agreement?

Boundaries beyond the conversation

These will be very dependent on the topic and nature of the conversation or issue you need to solve. Here’s some ideas you can consider:

  • Set timelines for actions that need to happen
  • Set owners on all agreed actions
  • Where are actions tracked – the best place is a RAID Register
  • Define how we know when something is done without needing to be prompted
  • Where are meeting discussions and agreements documented? Who documents? Who will this be shared with and who does that?


For boundaries to work, there needs to be a penalty when the boundary has been breached. This ensures that the value of the boundary is not diluted and taken seriously.

For each boundary agree on the penalty if the boundary is breached.

Depending on the severity of the boundary, these penalties can be as light-hearted or as severe as the team agrees. Some examples include:

  • Buying the entire team a coffee
  • Acknowledging personal responsibility to stakeholders
  • A formal warning
  • Having a key responsibility taken away from a role

Just like with writing any of the team’s rules of engagement, it is important to ensure that this is done with the entire team.

Without buy-in, the team is much less likely to recognise the value and not adopt the boundary and penalty approach.

Done right, difficult conversations will empower your team

The more you try to avoid the difficult conversations that come with project teams and project delivery, the more they will impact your success.

It’s normal to feel confronted by these types of conversations and getting good at managing direct conversations takes practice.

But it also takes working together with your team, and consideration to how you’d like to be treated if you were part of a project challenge that needed to be resolved.

What step will you take today to have more productive conversations around project issues?

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