Win Without Pitching®: Thinking

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The Questions to Ask When Considering a High-Risk Client Relationship

On my parents’ wedding day, family legend goes, my maternal grandfather turned to my father and menacingly said “We’ll see what kind of a son-in-law you make.” By all accounts my grandfather’s concerns were quickly assuaged and he and my father became very close.

Let’s try on the idea of you being as ruthlessly discerning with your prospective clients, if a little kinder in your language. What are the questions you would like to know in advance of working with a client to determine if this relationship is going to work? Employing the Win Without Pitching principle of Say What You’re Thinking (aka Kind Ruthlessness) let’s list the questions to which you would like answers and the direct-but-kind language you might use to get those answers.

Decision Makers

The most frustrating clients are often those with too many cooks in the kitchen. In any sale you need to identify the decision makers, but often, people other than those with a say in hiring you will have a say in the work you do—or they will feel that they have a say. You want to find out who on the client team has the ability to say no, to make or request changes, to delay the project or to just offer input; and if the number is high enough to concern you, you want to speak up.

“Once we’re working together, whose input or feedback on our work will be invited or welcome? How many people will have the ability to slow things down or degrade the quality of the work?”

If still concerned by the number, you might share that “In our experience—with creative work in particular—the organizations that limit the number of people having input tend to make braver decisions.” Groupthink, as we know, leads to lowest common denominator work.

Another danger of too many meddlers is your work being “circulated for comments.” If you’re worried about this, head it off before the engagement even begins by invoking policy. “It’s our policy that when the work we do is presented in your organization, we do the presenting. That way we can communicate all the subtlety and rationale that we don’t typically put into writing. I assume you’re okay with that?”

Alignment on Relationship Length

You might be set up to turn over clients and project work quickly, or you might be pursuing the slightly delusional idea of “clients for life.” Wherever you are on the relationship length spectrum, you want to make sure your clients are in roughly the same place. So go ahead and ask.

“What length of relationship are you looking for and why?” You might also ask “Is it the policy of your organization to review the account at defined intervals?”

I imagine my father clearing my grandfather’s first hurdle and then being told, just before their second wedding anniversary, that “As a matter of policy, I’m reviewing my daughter’s marriage every two years. I’d like you to complete this questionnaire, this financial forecast and prepare for the interview.”

“Why,” I can see my bewildered father asking?

“Well, people get complacent and we owe it to the family to make sure there’s not somebody better out there—more caring or with greater earning potential.”

If that’s your client’s policy, then they’re likely to be a shitty, price-buyer client and you’ll want to know it before you decide to work together. If you do decide to take them on at least you’ll know what you signed up for.

Another way to pose the question might be, “What do those in your organization see as the proper length of a relationship like this?”

Past Relationships

There may be questions you want answered about the client’s past. Just ask. “How long was your last relationship? Was that the right length or did you feel it ended too soon or went on too long? How did it end and why? What would you do differently if you had that relationship to do over again?”

If you’re particularly concerned—and feeling especially brave!—you might ask, “Would you mind if I had a conversation with the CEO or managing director of that firm?”


You want to know, in advance, if your client has any ideas on what your profit margin should be. The only acceptable answer is a variation of “we want you to make a lot of money by making us a lot of money.” Any client that wants to control your profit margin is not a good client.

“What are your thoughts on how profitable your account should be for us? Do others in your organization have the same view?”

You might even state, “I hope that our clients respect our right to earn extraordinary reward for ourselves by creating extraordinary value for them. What do you think about that?”


If procurement is going to be involved, you want to find out when they will appear and what their role will be. Again, direct questions are best. “What, if any, is the role of procurement in hiring a firm like ours? Do they share your view on our right to make money or are they solely focused on cost reduction?”

If you suspect procurement might be a problem, say so. “You seem to have a point of view that aligns with ours, but it hasn’t been uncommon for me to have reasonable conversations with people like you, only to be met with unsavory tactics from procurement later on.” Pause here and see if the client fills the silence. You might then ask, “If we get that far and I find myself in that situation, what’s your advice to me?”

Conversations Instead of Presentations

The Second Proclamation of The Win Without Pitching Manifesto is We Will Replace Presentations with Conversations. All of the language I have modeled above is just straightforward; questions to which you deserve straightforward answers. This is common sense but not common practice because we tend to think of the sale as a series of one-way communications: the client briefs you, you go away and do the work, then you present. The client listens then goes away and makes a decision. They then present that decision to you. There’s very little real proper dialogue in such a model and that’s what you want to change.

By learning to say what you’re thinking you create a real dialogue between professionals and an environment where everyone can speak frankly. You’ll also find that moving from presentation mode to conversation mode, in which you ask direct questions like the ones above, shifts the power balance toward you and you communicate that, like the client, you too are discerning of the fit.

I’ll ask my father how he replied to my grandfather, but I suspect he did the proper thing, said something polite and worked hard to gain his trust. I also suspect he was thinking to himself, “It’s a two-way street, old man. Let’s see how you shake out, too.” If he were looking for kinder words to speak, he might have said, “I’m sure we’ll both work hard to prove that we’re worthy of being in each other’s lives.”

Say what you’re thinking. Be kind, for sure, but be direct. Good clients will welcome a proper conversation.

Blair Enns
Blair Enns is the Win Without Pitching founder and CEO and the author of The Win Without Pitching Manifesto and Pricing Creativity: A Guide to Profit Beyond the Billable Hour.
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