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Conquering ‘The Conver$ation’

By Vanessa Doll

Talking about finances can be challenging–even in a business relationship–but it doesn’t have to be.

Recently, I was having a cup of coffee with my co-worker and she said, “You are good at having difficult conversations with clients.” It spawned one of those moments of professional self-reflection when you see yourself or certain circumstances through the eyes of another. The first thing I did was to, of course, graciously accept the compliment. The second was to wonder, “what the hell is she talking about?” 

I honestly can’t remember the last time I have had a particularly difficult conversation with a client. Sure, they have happened… in previous positions at creative agencies, and a LOT in my previous decades of working in the bar and restaurant industry. And let’s be real: Difficult conversations still happen with co-workers, my husband, family, and even my friends. But it’s been years since I’ve had a truly difficult conversation with a client.

“What she thought of as ‘difficult’ conversations are instead the inevitable talks I have with my clients regarding scope, timeline, and resources”

What I came to realize was this: what she thought of as ‘difficult’ conversations are instead the inevitable talks I have with my clients regarding scope, timeline, and resources. In creative agencies (and life), a lot of people hate talking about finances. We’d prefer money not be there, and instead focus on “the work,” but it’s there. It’s that tiny detail that permeates every aspect of the business, both on the client side and on the agency side. It’s how, together, the agency and the client determine what will be done, how it will be done, who will do it, when it will be done by. We start with a budget and a business objective, and we work our way backward. All of those pieces—scope, timeline, project management, consultation, revisions, deliverables—have to fit together within the budget. 

So why, when clients start asking for work beyond scope, or when agencies are delivering less than promised, does that become a difficult conversation? Like my mother is fond of saying about pretty much everything: It’s only difficult if you let it be. 

Often at Freshmade, we will deliver an extra concept, the added deliverable, work with the reduced timeline, and not say a word. Our mantra is “Never Settle,” and most of the time, that is our decision—we answered the ask but we also just “really want to show one more idea.” That’s not something my client asked for, and therefore, it’s not something they should have to answer for. In fact, our whole job is to help our clients be their best and we will gladly go the extra mile to get them there. 

But occasionally, we will get in too deep, be asked to overcommit a resource we never promised, or work on a timeline that will burn out my entire team. And when that happens, it’s time for a chat. 

“Authenticity” is a buzz word right now, but it’s rooted in the fact that humans really do appreciate honesty”

Here is how I see it: While money may get the project off the ground, people are the ones driving it to completion. And in my experience, people are generally fair and reasonable. “Authenticity” is a buzz word right now, but it’s rooted in the fact that humans really do appreciate honesty. And how you approach the issue makes all the difference. 

A few of my own personal methodologies for when the time comes to “have the talk” are:

1. Like a good steak, keep it rare

These calls should be infrequent at most. You do not want your clients’ reactions to your calls to be “my god, what now?” This article isn’t derived from hubris—I’m not calling clients left and right, keeping them in line, arguing against scope and timelines all day. If I had to do it all the time, my odds of these conversations turning confrontational would likely increase. And while I’m decent at confrontation and it can be part of the job too, I basically hate it. 

2. Don’t beat around the bush

The simplest way to avoid these conversations is to set clear expectations from the onset of the project, and outline it in the proposal, timeline, or whatever project management tool you are using with the client to align on the perimeters.

If we, i.e. our creative team, decides to show additional deliverables or concepts that are out of scope, I make it clear to the client that it’s our choice to do so.

In short, stylistically and personally, I don’t like to set very hard boundaries with our clients and our team enjoys being able to provide little extras here and there. However, by creating some firm boundaries in the first place, and diligently acknowledging when they are moving in one direction or the other, we are afforded the leeway without it getting out of control. That way, if it does start to get out of bounds, and it’s time to talk about it, no one (read: client) is very surprised.

3. Keep it low-key

Which leads me to my next point of keeping the “difficulty” of these conversations at bay. Don’t blindside your client. If I need to talk to my client about a “sensitive” matter, I do it one-on-one and I start fairly informally. I don’t overexaggerate the sensitivity of the issue, and I try to keep the drama WAY out of it.

For example, if you have a texting relationship with your client (for better or for worse, I am always available to my clients via text), I start by texting them, “Do you have a few minutes today? Just want to have a quick chat regarding XYZ.” I don’t create a meeting on the calendar because I don’t want to escalate the conversation to a higher level of formality than necessary. If you have done point 2 successfully, they will not be surprised by the time you reach out. You want to give them time to prepare their thoughts, but you don’t want to put them on the defense.  

4. Make no bones about it

MOST IMPORTANTLY: Now you have them listening, don’t waste their time. Be candid, honest, and straight to the point. Explain the situation from your point of view, do not skirt the issue, and tell them they have every right to be candid in return. This is not a difficult conversation, it’s just a conversation. And the best way to work something out is to have it out—not emotionally, not aggressively. Just honestly. 


I can only speak from personal experience, but I like to think that I have really good relationships with my clients. I mean, this is what I do! What I consider a “really good relationship” with a client is what makes the difference—an honest, candid and open one (to what’s realistic). We can’t control every project, and we can’t control every person’s reaction to circumstances. But we can be our true selves with them, and trust them to be human, even when it’s “just” business. With a little practice, you might not shy away from these types of conversations with your client. They may even begin to come easy.

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