How Tough Conversations Can Create Better Client Relationships


When you work with clients, sometimes you find yourself facing a tough conversation you’d really rather not have. You can feel your muscles tensing and sweat beads rising on your forehead and palms. This won’t be pleasant. And I’ll own up… Nothing I can tell you will ever make it pleasant.

But what I can do is give you some tips to help you do it well and feel a little more in control. And more importantly, when you face up to tough conversations and handle them well, they can lead to better client relationships.

Indeed, the advice in this article follows the principles I used when my relationship with a client had seemingly broken down completely. I decided it was worth one last shot. By confronting the central issues for each of us, and by declaring that I wanted to be as open, honest and generous as I could be (so we could fix things), I managed to trigger the conditions for rebuilding the relationship.

Your Starting Point

Always start with the end in mind, and always have a plan. Isn’t that just good project management?

What Matters?

So, before you even start the conversation, ask yourself what matters most to you. Take the 12-month view, rather than how you might feel tomorrow or next week. By the way, why not a 12-year view? Because at that level, the whole thing might seem wholly pointless!

And here’s a clue to things that won’t matter to you in 12 months. Or, at least, they really should not…

  • Scoring points off your client
  • Saving a few bucks
  • Making them feel guilty
  • Being “right”

Instead, you are likely to bring your attention to a stronger relationship, great testimonials (or, at least, a secure reputation), and maybe long-term profitability from the account.

Tough conversations are times when you often find yourself over-speaking. You say more than you intended to say and complicate things with unnecessary detail. Knowing what matters and what does not will help you keep the conversation focused. Look for the core of the conversation and decide to exclude anything else.

Have a Plan

Go into your tough conversation with a plan—but not a script. That would make it impersonal and inflexible. Think about what you need to say and how to say it.

Also think about what you should avoid saying: the recriminations and blame, the blind alleys that will distract you both from the real issues. Additionally, consider the process you’ll use. The next steps will help you.

Logistics for Tough Conversations

When and where you hold your tough conversation are important—more so than the easy everyday conversations, which can happen anywhere and anytime.

End of the Day

The end of the working day tends to be the best time for tough conversations that can upset the other person—and you. It means you don’t have to return to colleagues afterward while you’re coping with the mental and emotional processing.

However, some conversations need you and your client to be at your sharpest. They are not as emotionally challenging, but they are mentally hard. Put these into the morning while you are both still at your most alert, fresh, and resilient.

Safe Place

Think about where to hold your tough conversation. It needs to be a place where you will both feel safe while being as comfortable as possible. Meeting in private is ideal, but these days it pays to be aware of the risks and discomforts either of you may feel. Is there a public-private space?

You have three basic choices: home ground for you, home ground for them or a neutral place. All have advantages. The biggest factor is the feeling of safety, comfort, and psychological advantage.

If you are going to initiate the tough conversation, I would recommend you give up those advantages, and let your client choose the venue. Offer to go to them. This will make the tough conversation a little easier for them. That, in turn, will make it easier for you.


If your client feels at a disadvantage from the outset, they will be wary and defensive. They will be less open to your constructive suggestions.

Tough Conversations come down to Interpersonal Skills

The content of your tough conversation is important, but the wrapper is what will either form or break down the barriers to the connection between you and a now-wary client.

Listen Well

At all times, the one secret to hosting a good conversation (tough or trivial) is your ability to listen well. And your ability to listen to silence, or too incoherent struggles for understanding, will be at a premium. Commit yourself to focus on the quality of your listening.

The essence of a good conversation is asking questions and listening. If you give the gift of pure attention, two things will happen. First, your client will feel your respect for them, and for their perspective on the issues that have led to your tough conversation.

And second, in that silence of your listening, it won’t just be you who hears what your client is saying. They will hear themselves too. And sometimes, this will be for the first time.

Open Body Language

Relaxed, open, non-aggressive body language is best. This means upright, symmetric, and leaning neither too far forward nor too far back. This shows you are attentive and engaged.

Concentrate on good eye contact when you are delivering difficult messages, but be ready to break eye contact if they look uncomfortable. Note how hard eye contact can be. It is pretty easy to keep eye contact when you are listening: it’s far harder when you are speaking.

Give Them Time

People need time to process challenging messages. This is true, even if they were sort of expecting them. Allow that time, without filling it with questions, comments, or defense of what you said. This is the gift of silence.

As a bonus tip, if they ask you a question or make a point that is important to them, do not leap in and respond straight away. The message an immediate response gives is: Your question was easy; your point was trivial. No one wants to be told that. Instead, pause and think for a couple of seconds. The silence you give, before responding, says: That was a challenging question, your point was a good one, so I need to think about what you said.  How much more respectful is that response?

Give Them Space

Also, give them space to let their emotions out. It’s part of how we deal with tough conversations. Encourage it, but not in an intrusive or nosy way. Acknowledge the feeling they share, label the feelings you observe, but resist the temptation to dive in and tell your own story.

Moving Forward

As your tough conversation moves to a close, what are the tips for leaving a platform for a better future relationship?

Future Thinking

Once they have asked their questions and their emotions have cooled, turn the conversation to the future. By the way, this may need to be a second conversation, if the emotional temperature gets too high. So, don’t force it.

Future thinking generates solutions. Ask questions like: What would you like to have to happen as a result of this conversation? What do you see as the next step for us? You can also introduce your own hopes and aspirations.

Future thinking is far more valuable than present thinking or past thinking. Present thinking focuses on the rights and wrongs of the situation, along with mismatches in perceptions.; past thinking tends to focus on blame. None of this is as useful as setting the relationship on track and working together for your mutual benefit.

Cool Down

After your tough conversation, take some time to cool down. Never schedule another meeting straight after one of these. You may want to be on your own for a while. Or maybe you have a trusted colleague, who can listen to you as you share the non-confidential aspects of what happened.

At the end of the day, or the next morning, make a space to reflect on what happened. What went well, and what did not. What did you learn, and how would you modify your approach, if you had to do it again?

And, perhaps most importantly, what is the follow-up you need to make to ensure that the hard work you put into your tough conversation does not go to waste. Remember, strengthening relationships means demonstrating trustworthiness. Now would be the worst of all times to forget a promise or renege on a commitment.

Once you’re back on civil terms with your clients, the real work begins. They’re going to want to know the progress of the project and stay informed with detailed reporting. ProjectManager is a cloud-based project management software that gives you real-time data, so your reports are current and help configure them to reflect your client’s needs. Try it today with this free 30-day trial and see for yourself.

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