5 top tips to have difficult conversations better

Would you like to have difficult conversations better? In this post I aim to share my experience of what works and what doesn’t.


Most of us avoid difficult conversations because deep down we hope that the need to have them will go away.  Occasionally, this happens and we are proved right for putting it off.


The person chooses to leave the organisation and we never see them again. A restructure and we’re given a different project. Or perhaps we move on ourselves and that deals with the issue.


In reality though, most of the time the problem does not go away and can even get worse if we don’t find a way to tackle things that are coming up.


Over the years of working as a mediator, I’ve learned some top tips  that make it more likely that we’ll get what we want when we have difficult conversations.  Here are my five top tips.




Have the conversation sooner rather than later


Many of us wait until things are really difficult before broaching the tricky subject. This makes the conversation more daunting than it needs to be.


This is true even in low-level situations where there isn’t really an overt ‘conflict’.


Imagine the following situation.


You are new to the organisation and your manager gives you a brief on a project that she wants you to work on. After reading it, there are several acronyms and terms that you don’t understand.


If you’re totally honest, you’re really not that clear on exactly what it is that you’re being asked to do either. You feel a bit frustrated and annoyed that she didn’t explain it in more detail.


However, thinking that you need to prove yourself because you’re new to the job, you get on and give it your best shot.


You set up some meetings to get started and at one of the meetings, someone asks for more background information about the project. You have no idea, so you blag your way through but the other person questions some of your answers. You feel mortified. You promise to go away and bring back some answers.


Now you know that you really need to have that difficult conversation with you manager and you feel embarrassed because it’s been three weeks and you know that you could have had the conversation three weeks ago.




Have the conversation in person, however hard it may seem

In the example above, the temptation might be to send an e-mail to your manager with a number of questions instead of facing her to ‘fess up’ that you need more clarity.



However, in my experience as a mediator, 99% of the time having difficult conversations over e-mail only leads to greater confusion and often worse. This is an extremely common trend because it sometimes feels easier.  Take a deep breath and ask for a meeting.




Prepare yourself for the conversation


Make some time in your diary to prepare for the conversation.  As you prepare, consider the following questions. What is your intention with this conversation? What do you need to get out of it? How do you want your approach to be with the other person?

Even taking 15 minutes to reflect on these questions will more likely lead to a better outcome.


Taking our example above, you decide that your intention is to admit that you’re not sure about the project and you need a bit more support getting to grips with it.


In terms of what you need to get out of it, you need some clarity on what the various terms mean and also on your role. You also need to know who is the best person to call on for future support and questions – your manager or someone else.


Finally you need to be heard and for your manager to understand that you need a bit more direction and support as someone totally new to the company.


You decide you want to be open, honest and to make an apology for not asking sooner.



Go in there with the intention to listen first rather than waiting to be heard


If you go in there with an intention to really listen, you’ll build rapport and be much more likely to get your concerns and needs heard.



A simple tip here is to reflect back some of the key things that the other person says. This is an extremely effective communication tool that has several purposes. It builds connection. It lets the other person know that you have heard them. You act like a mirror to their words and that means that they can correct anything that you may have misunderstood.  It creates much clearer communication. It’s about reflecting back the most important points.




In our example, let’s say that your manager tells you what the terms mean and a bit more about your role. You say to her, “so can I just check I’m getting this? You’re saying that IGP means the ideas generation project and that you want me to coordinate this project by focusing on building key partnerships and coming up with ideas for how to integrate these new technologies? So it’s an ideas generating role mainly?”.




However, you’re still left unclear about who to go to for support and reporting back. Your manager seems too senior but you’re not sure who else to go to.



Be clear, open and direct with your communication



It can take time to get clear. Don’t give up! If you still don’t understand what’s been said or think that they haven’t heard your perspective, you can state your point of view clearly, respectfully and directly. In this process, aim to communicate what your main need is.



“OK I think I’m much clearer on my role. I’m still not quite clear on who I report back to once I’ve done this initial scoping work on the IGP? Where does it go from there? I really need to know who to report to and also who I can go to if I still have questions.”


What would your top tip for having difficult conversations better be?



I’d love to hear!

Portrait of successful Businesswoman by the window

How to be clear about your role – and why you need to be

Over the years I’ve noticed that many disagreements at work begin with confusion about a person’s role and the expectations of the role. Often this has been going on for years and people are left floundering, getting on with the job to the best of their ability but with a nagging sense that they’re not doing enough. It can be a source of much stress and anxiety.

If this resonates, you’re not alone.

In the worst cases, people have gone into a role with a job description that is so vague it’s unsurprising that they are totally unclear. In one case, there was no job description at all. (Yes it does happen). More often, though, it is the understanding of what the job involves and which elements should be given priority that creates problems.

Let’s be honest, many job descriptions are more like wish-lists to Santa, spelling out every possible area of responsibility and task that the person might be expected to undertake. These days everyone is over-stretched, trying to cram more and more into their working days. Managers have crazy workloads that never really end and job roles morph and change over time to the extent that often someone ends up doing a completely different job to the one that they were originally employed to do.

Given these contexts, it’s not surprising this is a grey area that is ripe for tensions.

The challenge for the individual is to decide how they actually use their time.  Conflicts can arise when colleagues or managers and staff have very different expectations about these things.

Some examples of areas of tension include:

  • Which project, programme or tasks should be prioritised.

  • Who is responsible for leading on a particular project or programme.

  • What support is given and expected in terms of supervision and mentoring.

  • How things are communicated and who is included in those communications.

  • When there is a difference of opinion or some concerns about a piece of work, how this is dealt with.

  • Whether or not home-working is permitted, and if so for how much of the time (in relevant industries).

  • How much to engage as part of a team and how much to ‘go it alone’.

So how to deal with this?

The key thing is to deal with the situation sooner rather than later. If it is avoided, it won’t go away, rather it’s more likely to grow and become a bigger problem further down the line.

In my experience as a mediator, there is no substitute for face to face, open conversation. Texts and e-mails are good for setting up these meetings but they almost never work when the discussion is ongoing and important. Although they seem to be efficient, e-mails end up taking up more time. Here are some top tips for anyone faced with this situation:

  • Bite the bullet and fix ‘that’ meeting with your line manager. It won’t be as bad as you think. If they are really busy, keep pressing for the meeting until you pin them down.

  • Prepare for the meeting by thinking in advance about what you really need and what you’d ideally want to get out of the meeting. Be specific.

  • Manage your state of mind and emotion. Use whatever grounding practices you have in your toolkit- mindfulness, meditation, prayer to also prepare your attitude to be open and receptive.

  • Go into the meeting with a humble and listening attitude.

  • Practice summarising what the other person says to check your understanding.

  • Ask questions and don’t be afraid to ask what an acronym or piece of jargon actually means.

Putting in place these tips will set the frame for some high-quality and open communication.

And hopefully, you’ll have more clarity at the end of it.

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