Tips for having difficult (client) conversations

Not having difficult (client) talks is costly for individuals, teams, clients and the business

Having difficult conversations with clients (or with people in general) is… well, difficult! And that applies to both those leading the conversations and the other participants. But the cost of not having these discussions tends to be much higher than just getting on with them. So I’m sharing my tips to empower you to have those difficult client conversations sooner rather than later.

The cost of avoiding difficult conversations 

Not having difficult client talks is costly for individuals, teams, clients and the business. Most people don’t like having challenging conversations because they feel uncomfortable and, as humans, we tend to avoid discomfort wherever possible.  

If a challenging situation has reached a point where you are considering getting out of your comfort zone and having a difficult conversation, ignoring the need for it, or delaying it, is unlikely to make the situation better. Chances are that the client is not aware (or not fully aware) of the situation, and/or the impact it’s having. So avoiding having that difficult conversation will at best mean things don’t change which is not great. Or perhaps mean the situation gets worse before you have to speak with the client anyway!

This is what makes skipping difficult conversations costly. The costs can be both quantifiable and trickier to measure. Think delayed or inefficiently delivered projects, frustrated and unproductive teams, financial losses, reputational damage, staff attrition and more. 

Tips for making difficult conversations easier 

So, here are my tips for having timely and effective client conversations. 

Preparing for difficult conversations  

The more prepared you are for having a difficult talk, the more likely it will go well. Or as well as it can go. But, don’t use preparation as an excuse for procrastination. 

Start by deciding who to speak with and keep the number of people to the minimum necessary. Next, consider the best setting for having the conversation (online or in person), and when to do it for the message to land with the most impact. Don’t squeeze it in 15 minutes before an important meeting. Give the attendees a heads up in advance about what you’d like to talk about, this can be better done in person than writing, to prevent misunderstandings.  

Collect feedback from others wherever possible as they might be able to add different perspectives, or help you frame the points you want to make better than you would have on your own. This can be through 1-2-1 private chats, a team retrospective, or anonymously.

While it’s usually better to come up with solutions together with the client, be prepared and have some ideas ready to suggest for dealing with the situation, just in case you’re asked. 

Having difficult conversations  

Once you’ve prepared for having a difficult conversation, it’s time to do it. Arrive on time, don’t jump straight in, and start by thanking the client for speaking with you. Give them some contextual information about why you wanted to talk with them, and ask if they have any questions before you dive in. 

I suggest you stick to a maximum of 3 main points. If there’s more, group or summarise them into the most important high-level themes. Sharing more is likely to be challenging to process all in one go and might dilute the message. It’s best to save things for another time if there’s more to raise. 

Focus on what you or the team have observed, the data that supports it and the impact it’s having instead of presenting the points as ‘universal truth’. Acknowledge there may be details you are not privy to, but this is how you experience the situation and its effect. Refrain from blaming or pointing fingers – try to not make feedback personal and encourage the client not take it personally. 

Avoid talking at people for long periods of time  – pause regularly and check in to see if others have questions after each point. Listen carefully and actively to what is being said and ask about the client’s view of the situation. 

Be honest, stick to the facts, and always try to remain calm and respectful, regardless of how others respond. While difficult conversations can be triggering and feel uncomfortable, they should never make you feel unsafe. If that happens, suggest following up at another time and bring the discussion to a quick close. 

Remember to remind the client that having this conversation is about helping to make the situation better for everyone. Focus on agreeing the next steps and how/when you will next check in with one another. Ask the client if you can help to address the situation and remind them that you’re there if they need you. Offer examples of how you could help. 

Lastly, don’t forget the human side – you’re not a machine. If you or the client are finding the conversation challenging, acknowledge that. 

Following up after a difficult conversation  

It’s important that you don’t just have a chat and leave it at that. Send a follow up message to thank the client for their time, briefly recap the points you’ve covered, and outline the next steps you both agreed. 

Give the client the necessary time to address the situation before checking in with them and suggesting a follow up conversation. You can prepare for this by using the tips shared earlier. The key takeaway here is – follow up!

To sum up  

Hardly anyone enjoys having difficult talks, but most of us have to do it at some point – you are not alone. We learn how to do this by practising and iterating. The important thing is not to avoid these conversations, prepare for them, be honest but empathetic, and follow up.

Good luck!