What to Say When: A Cheat Sheet for Tricky Conversations

Art by Andrew Colin Beck

Do you ever find yourself tongue-tied or even speechless with a client or your boss?

You know those awkward moments, whether in real time, on the phone or sometimes even in an email exchange, when you have trouble coming up with the right thing to say.

Well, you’re not alone. We all get tripped up and go a bit blank in unfamiliar or high stakes situations.

The first thing to keep in mind is that, no matter the situation, there is no “right” way to respond and no “right” thing to say. In fact, there are infinite ways to respond to every situation, depending on a myriad of factors.

So don’t feel pressured to come up with the perfect response right then and there. When in doubt, ask for time to think.

Say this: “I’d like to give this some thought. Let me get back to you tomorrow, if you don’t mind.”

You don’t even have to explain why you need time! You just need to muster the courage to ask for it.

Following are five tricky scenarios for creatives, with different approaches that use curiosity, generosity, humility and humor to get your point across. Try them all and see what works best for you. 

what to say when ... cheat sheet for tricky client conversations

1. What to Say When … Your Work Goes Unacknowledged

The situation: You work behind the scenes on many projects and you do excellent work, but no one knows because you don’t like to promote yourself. Your mother taught you not to brag, so you rarely speak up to share your successes. As a result, those who could be helping in your professional development don’t have the ammunition to do so.

What you may be thinking: “Why doesn’t anyone recognize my role in these projects?”

The Solution: Try to shift the way you think about “self-promotion.” This is not about bragging, but rather conveying facts about your efforts. Find your own communication style to get the information to the right people—those who can help you grow professionally. Present the pertinent details in a matter-of-fact way, using verbs rather than adjectives and emphasizing your process as well as the effect of your actions.

What you could say:

• Curiosity: “The recent project we worked on was especially successful. How can we best spread the word about it and to whom?”

• Generosity: “Would it help you communicate our team’s success if I share details about how we approached it? Would you mind if I send you regular updates on the progress we’re making on my team and my role in it?”

• Humor: “My mother would cringe if she heard me bragging, but I’ll do my best.”

Big Takeaway: If you don’t speak up about the work you’re doing, no one will know.” And that could do damage in the long run, to you and to your team. Plus, communicating your achievements is likely to help your boss communicate the team’s achievements up the chain as well.

what to say when ... cheat sheet for tricky client conversations

2. What to Say When … You’re Getting Too Much Work

The Situation: Your department just lost another employee (or just acquired another project) and you were assigned additional tasks, despite the fact that you’re not able to complete the work already on your plate.

What you may be thinking: “This isn’t fair. I can’t take on anymore.”

The Solution: Make your boss aware of your capacity. If they already are aware but can’t reduce your workload, ask for their input on how the tasks are prioritized to ensure you’re completing the most important ones first.

What you could say:

• Curiosity: “Do you really think this can be done well enough with fewer hands?  How important is quality in getting these jobs done?”

• Humility: “I appreciate your trust in me with the additional responsibility, but I will need some help handling this extra workload. Here’s what I think I will need.”

Big Takeaway: Taking care of yourself is your number one priority. You are the one who must advocate for yourself. If you burn yourself out, you’re of no use to anyone. So be clear, first with yourself and then with your superiors, about what’s possible, and make sure you’re doing the most important tasks.

what to say when ... cheat sheet for tricky client conversations

3. What to Say When … The Client Doesn’t Like Your Work

The Situation: You submitted your deliverable for a project and the client doesn’t like it but can’t articulate why. Or, they say something that doesn’t give you any direction and isn’t helpful.

The Solution: Part of your job is to help non-designers come up with the words and the language to communicate what isn’t working.

Say to yourself: “It’s not personal, and I need more information to understand what’s going on.”

What you could say:

• Curiosity: “What isn’t working for you? Can you point at it? Can you identify which aspects are working?” (You may have to hold the client’s hand during this process or provide multiple-choice options for them to say “yes” or “no” to.)

• Generosity: “It seems like you’re having trouble articulating what’s not working. How can I help you do that?”

• Humility: “I’m sorry to hear it’s not working for you. Let’s put our heads together and figure out where the problems are.”

• Humor: “Uh-oh. Is this one of those ‘the CEO doesn’t like red’ situations?”

Big Takeaway: You have to be a detective to find out what isn’t working so you can come up with a better solution—all without taking it personally.

Recommended Resource: Discussing Design, by Adam Connor and Aaron Irizarry

what to say when ... cheat sheet for tricky client conversations

4. What to Say When … The Client Wants Something Different

The Situation: You deliver the work that was commissioned and the client says, “We like it but our CEO wants to go in another direction.”

What you may be thinking: “I hope you don’t expect me to do that for free.”

The Solution: This is actually not a problem for you—at least it shouldn’t be. In fact, things in the business world are constantly changing, so this happens often. When the client changes the direction or the scope of a project, you should still be compensated for your work. It’s up to you to make it clear that the new scope is additional.

Say this first:

“To be clear, what you’re asking for is not included in our original agreement.”

Then, continue with:

• Curiosity: “Is there anything about the existing deliverable that could be repurposed or used in another way?”

• Generosity: “Would it be helpful if I provide an estimate for this new direction? It may be less expensive since we’ve already done some of the discovery.”

Big Takeaway: This is a situation where it’s easy to get trampled if you don’t stand up for yourself. Your client may not want to “pay the price” for what is essentially their responsibility, so this is where your backbone will come in very handy, though it may take practice.

what to say when ... cheat sheet for tricky client conversations

5. What to Say When … The Client Doesn’t Want to Give Your Their Budget

The Situation: A prospect contacts you about a new website and asks for a proposal. You’d like to work on the project but you don’t want to spend time on a proposal unless you know they can afford your fees. You ask for their budget and they say, “We don’t know.”

What you may be thinking: “I don’t want to annoy them or scare them away by insisting they give me a budget. I’ll just do the proposal.”

The Solution: Before you agree to spend time working on a proposal, you must make sure you’re a good fit, money-wise. Put some hypothetical numbers on the table and see how they respond.

What to say:

• Curiosity: “Could you tell me what end of the spectrum you’re on? Are we talking $500, $5,000 or $50,000?”

• Generosity: “I understand if you don’t want to share your budget, but it would be helpful to know what range you have in mind so I can tell you what is possible within that range.”

• Humility: “I’d be happy to provide a proposal, but first I want to make sure we’re a good fit so no one’s time is wasted.”

• Humor: “I want to make sure my proposal doesn’t make you fall off your chair.”

Big Takeaway: Even the high-quality clients may not know what their budget is. But you do need some direction from them before investing your time in a proposal. Plus, you will often find that, when actual numbers are part of the conversation, amazingly, the budget reveals itself.

what to say when ... cheat sheet for tricky client conversations

Tack this article up on your bulletin board as a “cheat sheet” to eliminate, or at least reduce, the awkwardness of those moments.

Above all, know that you’re not alone. It’s very challenging, for creative people especially, to come up with the right thing to say under pressure. But with practice, it gets easier.