How to Prepare for Difficult Client Conversations External communications can be tricky, but you can make these conversations easier.

By Hila Levy-Loya

Opinions expressed by Entrepreneur contributors are their own.

External communications can be tricky. There are a lot of moving parts, and you're not always clued into everything going on with your client. Sometimes, this means you'll need to have a tough conversation or two to get you and your client back on the same page.

Before you cue the anxiety, remember that external communication is a skill you can learn and master with practice and an understanding of you and your client's goals. In a client-focused role, we can all hone our skills to make these difficult conversations a little less stressful. While these types of conversations may never be fun, they can be necessary. If done well, they can provide both parties with opportunities to grow.

Here's how you can make difficult conversations a little bit easier and more fruitful moving forward.

Build trust early on, and maintain it

People in higher-trust workplaces are shown to have 74% less stress than low-trust workplaces. Building trust is just as important externally as it is internally to reduce your stress and the stress of your clients.

Trust with new clients doesn't come overnight. But if you make it clear from the beginning that you're working toward the same goals, your clients will be able to start building that trust early on — setting the stage for more productive conversations moving forward.

To do this, you need to be extremely transparent with your client about your work. Don't stop at telling new clients what you're doing, but also take the time to explain why you're doing it and how it contributes to their goals.

Another way to build this trust from the start is honesty. You aren't always going to have the right answer, but if you're upfront about not knowing or needing time to process a question, your client will see that you're being thoughtful about your work together.

Once you've set the foundation of trust, you need to continually build on it, demonstrating to your client that they're a priority and that you're continuing to work toward a common goal.

Related: The Top 5 Reasons Why Entrepreneurship is Difficult (and How to Overcome Them)

Create a culture of open communication

Difficult conversations are much easier when open communication is the standard from the start. There will always be a need for uncomfortable conversations at work, especially when working with clients who don't fully understand what you're doing and why you're doing it. But, keeping an open line of communication makes clients feel more comfortable expressing their opinions, and makes the partnership more productive as a whole.

Creating regular check-ins with clients to reevaluate goals and discuss what's working (and what's not) is necessary for partnerships to grow. This is only more necessary as the way we work has shifted in the last few years, with fewer in-person meetings and more conversations from behind the computer screens.

Technical barriers can make these situations feel even more difficult, so regular conversations and goal-setting will help make sure you're aligned. That way, when an uncomfortable conversation is necessary, you have an established relationship and way of communicating to make it as productive as possible.

Related: 7 Ways to Learn From Difficult Conversations

Mistakes happen (but you need to learn from them)

When you're new to client communications, there can be a constant fear of messing up. While it gets easier for more seasoned employees, this fear may never fully go away. That's why you have to realize from the start that it's okay to make a mistake. Sometimes you may over-promise a client or make a call that, in hindsight, wasn't the best option.

It happens to all of us, even the best client communicators. But, if you've established a strong foundation with your client and created an environment of trust and transparency, it's all going to work out. The key is to admit when you didn't get something quite right as soon as you realize it, and come up with a solution to course correct to get your client back on the right track to their goals.

Once your client is back on track and the issues have been resolved, it's time for personal reflection. On your own time, take a moment to review what happened and learn from your mistakes. Speak with managers and team members about what went wrong and how you could have handled the situation better. This way, when you're faced with a challenge like this again (and you likely will be), you'll be better suited to make the right call.

There are a lot of unknowns when it comes to client communications, but building positive relationships and creating open communication is the best way to ensure that when these difficult conversations need to be had, you're prepared to move forward confidently.

Related: How to Handle Difficult People (and Still Achieve Your Business Goals)

Wavy Line
Hila Levy-Loya

Entrepreneur Leadership Network Contributor

VP of Customer Success & Experience at

Hila Levy-Loya is the VP of customer success and experience at with over 20 years of experience in tech. She oversees everything customers experience, from speedy responses to their inquiries to education on the product and continually supporting teams of all sizes using

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