A Guide To Difficult Conversations For Agencies

Client Communication


As an agency owner, this will happen to you at some point. The need for a Difficult Conversation.

It could be that “we have to talk” which you send to a team member, dealing with a difficult client or simply having to tell any client, supplier or team member something which they won’t want to hear.

Some people thrive on this kind of thing, but most of us dread having to be the one to burst someone else’s bubble.

How can you prepare yourself and what strategies can you use during the conversation? Let’s look at a few ideas.

Need a quick checklist for difficult conversations? Grab ours here.

Prepare Yourself

For many people, chances are you’re getting yourself pre-worked up worrying about the reaction of the other person and the outcome of the conversation. This can really impact how you go into it, so relax and follow these tips.

Alter Your Mindset

It’s simply not productive to go in as though a negative reaction is a foregone conclusion. Think about it as a constructive conversation to ensure that development needs, project outcomes or quality standards are met.

You should also understand that avoidance of difficult conversations can often lead to poor business decisions, negative impacts on your team or unnecessary consequences. These can happen if the behavior you want to remedy or client directive you need to change continues.

Many people find that using a breathing technique such as coherent breathing is effective in helping them to calm down and center themselves prior to a difficult conversation. If you’re in a more calm frame of mind, things are more likely to stay under control, at least from your end.

Avoidance of difficult conversations can often lead to poor business decisions


It’s never a good idea to be scripted, but writing down your key points is a great way to solidify them in your mind and ensure you don’t leave anything out. You should also know the answers to these key questions:

  • Why are you having this conversation?
  • What are you hoping to accomplish from it?
  • What does your ideal outcome look like?
  • Am I making assumptions about the other person’s intentions?

Leadership coach Julie Ringer suggests that you should monitor yourself for any “hidden” purposes which may not be so honorable. For example, if you want to punish rather than correct and support. It is always a better idea to be going in with good intentions for the purpose of the conversation.

Look At “Their Side”

There’s a good chance that something you see as a problem is not perceived as one by the other person, or they think something else is the problem altogether. Bear this in mind before you head into the conversation. Is there something you may have missed? Don’t enter the conversation believing that you have all the “right” answers.

Handling The Conversation

It’s always better to have given yourself the preparation time rather than diving into a conversation. This gives you time to calm down if necessary and to hopefully have a better handle over emotions which might impact upon the conversation.

Your preparation gives you a better chance of getting out what you need to and avoiding any reactions you might regret later. Generally, you don’t want to burn bridges with clients, nor do you want to put yourself in conflict with any employment laws when dealing with team members.


You’ve called them to a meeting and, especially for team members, this could mean that they’re already nervous.

Most people would like to end the conversation with feeling good about themselves, relating well with the other person and achieving shared goals. As Dr. Fred Kofman points out, this means you shouldn’t leap immediately to the content of the conversation, because you need to make contact (relate with the other person and have them relate to you) first.

That being said, don’t delay the conversation and don’t try to garner sympathy (for example: “I really hate having to say this, but …). Judy Ringer has some good suggestions for conversation openers in the image below.

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Explain concisely what the issue is, whether it’s the implications of a client’s approach or the impacts of something going on with a team member.

Never assume that the other person can see things from your point of view. If you have evidence or examples to back up what you’re saying, use them to ensure you are clear.

A point to keep in mind is to be compassionate, but not overly emotive. If you’re fishing for some kind of sympathy, you will probably generate resentment instead. Don’t make the other person (who is possibly battling “victim” feelings) feel like you are looking to be a victim in the whole affair.

Remain Calm

As Dr. Kofman says for LeanIn: “If you follow the rule ‘when someone pushes, push back,’ you’re always going to end up stuck.”


As his video reveals, when someone pushes with “you’re wrong”, “yield” by turning to look at their perspective (even if you think it’s crazy!). This will put them in a better frame to in turn, look at something they’ve missed from yours.

For example:

Client: “You’re wrong.”

You: “Please tell me your thoughts on it.”

No pushing back, simply stopping to listen to their perspective.


No one likes to feel as though they’re being railroaded and not heard, so ask the other person and take the time to listen. Summarize their points back to them, for example, “so from what I understand, you feel that …” This gives them the chance to add anything they may have missed and communicates that you’re trying to be fair.

While you’re listening, be processing more than just their words. What does their tone or body language tell you? Obviously if you’re conducting the conversation remotely, you’re going to rely on tone and what they actually say, unless you’re using a video link.

Ask Questions

If you don’t understand the other person’s viewpoint, acknowledge that you don’t and ask questions. This at least lets them know that you’re prepared to listen and are interested in understanding their view.

Be Solution-Focused

The results of any difficult conversation tend to revolve around your ability to remain calm and on task, and how focused you are on coming to a reasonable solution.

If possible, involving the other person in coming up with solutions is a good way to keep the relationship on track and have you both working toward a common goal. If you can, find something you like from what they’ve suggested and work to build upon it. Keeping them engaged will go a long way toward getting a positive result.

Just remember here that you may need to offer something back. For example:

  • If you’re delivering bad news to an employee (you need to let them go), offer a recommendation if possible.
  • If you’re telling a client you won’t be able to complete something as they’ve asked, offer a reasonable alternative solution so they at least feel that you are making an effort.
  • If you’re having a “poor performance” conversation with an employee, offer a solution for how you can support them to improve.

You may be willing to make some compromises, but always come back to those original thoughts about what you’re hoping to accomplish. Get something out of it that works toward that goal and do not bend on your essential values.

Confirm The Next Steps

This is often the part that gets left out with any difficult conversation. The participants are often eager for the conversation to finish and walk away in relief when they think they’ve got a solution. However, the issue hasn’t concluded until you’ve put the next steps in place, so be sure to confirm these before you part.

Need a quick checklist for difficult conversations? Grab ours here.

Final Thoughts

Difficult conversations can weigh heavily on our minds and cause stress which often turns out to be unnecessary. If you’re looking at having one of those conversations, prepare your mindset first so that you’re set on accomplishing a goal rather than any emotive actions.

Be prepared, connect with the other person, explain concisely and, most importantly, listen. Everyone wants to feel that their views have been heard.

Remain solution-focused and calm throughout. These two factors will play the biggest role in whether or not the conversation turns out well. Finally, make sure you’ve put next steps in place before concluding the conversation. These are essential for getting action on the issue.