Cutting Ties with Freelance Writing Prospects

A number of years ago, I had connected briefly with a client prospect at a trade show who showed interest in working with me.

Let me rephrase that: I connected repeatedly with that client prospect, first at the trade show, then close to two dozen times over the years via email and in person.

After four years of the back-and-forth, I stopped reaching out.

It may seem counterintuitive to drop the conversation with a “warm lead” like that. And maybe I was wrong to not continue reaching out.

But I wasn’t wrong.

I really hated making that decision, too. The guy, whom I’d gotten to know quite well, is a nice guy. And he sought me out in a crowded conference hall to tell me he wanted to work with me.

Yet I could tell by the conversation that ensued that it would never happen. How could I tell? Because there was no conversation. Zero. I checked in a few weeks after that face-to-face per his request. Then I followed up a month later. Then four months later. Then at six-month intervals. When I saw him in person, he was always just “ramping up” his communications strategies for the upcoming year, or he was hamstrung by higher-ups.

If I’d known about it, I would have used Cathy Miller’s final approach, which gives them an out as much as it gives them a way to continue the conversation. Cathy asks them if it’s okay to continue reaching out, then she adds a brilliant teaser: an I don’t want to be a pest, so let me know type of tease.

It’s brilliant, really.

It’s also tough to know when to pull the plug. Really tough.

I’d like to say there’s a magic formula I use, as in I’ll contact them seven times and if they don’t buy, I’m done.

But that’s too simple. People don’t often have a need at the seventh contact. So if I stop then and they were ready to buy on contact #9 or 10, I’ll never know.

Decades ago, I was working with a real estate agent to find a house. He showed us four homes. Then he stopped returning our calls. Was it something we said?

No, it turns out. I heard from another agent years later that this guy had a hard-and-fast rule: he’d show you four properties. If you didn’t buy one of those four, you weren’t serious about buying. You were wasting his time.

Isn’t it funny that we bought property #8 from a different agent?

The problem with his theory is what is wrong with writers setting arbitrary benchmarks: the timing could be off.

In fact, with the agent, his selections could have been off because he didn’t listen to us. Or he could have pushed something on us we simply weren’t interested in buying (he did in one case). The reason we weren’t buying could well have been entirely because of what he was or was not doing. Or it could have been (and was) because the right house wasn’t there yet.

With writers, it’s more about timing and message. We might have a great message, but the timing is off. Or the timing could be spot on, but we’re not really appealing to the prospect.

So how do you know when it’s time to halt your communication with a prospect?

I used to say you never do. And in many ways, you don’t really. You see them on social media, in email, at events sometimes. You aren’t ignoring them. You’re just not actively marketing to them anymore. And there’s something to be said for that. They know you pretty well after a few years. You’ll encounter them on occasion and, hopefully, you’ll have a nice conversation with them.

But let’s see when you should be thinking to put these prospects on the occasional-encounter list:

When there are crickets.

That’s usually the first clue that a relationship is going nowhere. I still reach out, and I tend to ask questions to elicit some sort of response (hopefully). But if I’ve been holding a one-sided conversation for longer than six months, that could mean they’re not interested. (And that’s when you do what Cathy Miller does and ask outright.)

When you’re stuck in the tire-kicking stage.

If you’re heading into your fourth or fifth phone call/email conversation with this prospect, there’s something they need to move the needle toward Go. Ask them. If the answer is they’re just trying to figure out how to work with you, show them. Do what you can to get them to Yes. But if you’ve exhausted the conversation despite their wanting more conversation, try asking them what it will take for them to move forward and how you can help them get there. Particularly if they’ve never worked with a freelance writer, they could be genuinely confused. But if you can’t get a sense of their commitment to their own needs, it might be time to suggest the conversation move permanently to email. From there, you’ll be able to tell if they’re serious about hiring or if they want to play with the idea. And you can gracefully bow out of the conversation when you sense that time is up.

When there is no plan in place.

I’ve had wonderful conversations with prospects who started the phone call with asking me what projects they need to be doing. My answer is usually “What have you tried so far? How did it work for you?” or I give them a “Here’s what you might want to consider” list. But I won’t formulate their marketing plan right there on the phone without a contract. Nor will I take that on without a contract and a LOT more information. If they assume you’re going to build that for them and then maybe they’ll hire you, I’d say that’s the ideal time to consider if this relationship is worth it to you. Even if you decide to move forward, that next step would be a contract in front of them. And no work from you without a signed agreement and an upfront payment.

When every conversation starts and ends with money.

This one isn’t a deal-breaker necessarily. I have one client who started our first conversation with “How much is it for…?” Five years later, I do plenty of work for them. But when it’s the sole focus of the conversation, and it’s obvious they’re far too concerned with budget over outcome, you may want to wish them well and refer them on to another writer.

When inconsistent communication prevails.

You did the job and they stopped responding after your invoice. Or you listened intently for an hour and they still didn’t tell you what they do for a living. Or you’ve shown up for the eleventh conference call and once again, the client has forgotten their own meeting. Or they want to hire you for a book project that becomes a children’s book project that becomes a business book that becomes a tool to help the prospect gain custody of his kids…. That’s when you walk away (or in the case of that last one, run away).

When there’s an unhealthy imbalance.

I should have walked away years ago when the client prospect looked at me and said “Write this down.” I walked away when the prospect said I needed to lower my rate. I walked away when the prospect said I was getting paid “with the royalties” of his unwritten, un-outlined book idea. I walked away when the prospect said I must be available on weekends and holidays. I walked away when the prospect wouldn’t sign the contract (“I prefer to build trust”). I walked away when that same prospect said he “rounded down” the pay per article.

You’ll walk away when the terms make your intuition stand up or make your skin crawl.

Writers, how do you determine it’s time to stop reaching out to a client?
Do you continue to communicate on a less-targeted level? If so, why? Why not?