Be carefully annoying

No one's paying more attention to you, than you

Over the summer, The New York Times started offering Connections puzzles — a grid of 16 words that you group into four sets of four, with each quartet uniquely linked (connected!) in some way. The puzzles grew in popularity. I love them.

A month ago, I started sharing my own take on Connections puzzles, which my name requires I call Conlextions. I love making these puzzles, because they make my brain work in a fun way. And because I’m making them, I’m also of course sharing them, with a new puzzle appearing each day on my site.

Photo by Sigmund on Unsplash

I share each puzzle I make on Mastodon, Threads, Bluesky, and Facebook. Sometimes I post them on LinkedIn.

It’s not for profit; it’s for fun. (Donations have raked in a whopping $26 for Conlextions to date 😂.) But I share each new puzzle in all those places because not everyone has seen them yet. People who already like my puzzles may use my posts to remember to play (and then share their scores, which I love!). Other folks — folks who haven’t yet seen any of my posts, or saw them and ignored them — might eventually discover my puzzles. And it’s fun for me that a few hundred people play my puzzles each day. I’d like that number to keep growing.

Of course, there are some people who never want to play one of my puzzles. To them, my daily posts might be a little annoying. That’s a tradeoff I’m willing to accept, because social posts that don’t interest you are easy to scroll right past.

I’m bringing all this up for a reason, and it’s not to stealth market my Conlextions puzzles to another audience via my Substack. (Though, please, feel free to check them out.)

Just yesterday, a client mentioned he’d discovered my music album after a mutual contact pointed him to it. And that same client mentioned that he only discovered that same day that I publish this very Substack.

I’ve written before about shameless self-promotion. If you don’t tell the world what you’re doing, the world won’t know. My puzzles are meant to be shared and played; if I don’t tell folks about them, they can’t possibly know they exist.

This is important in closing deals, too. I had multiple conversations with clients this week about when and how to check-in with leads who’ve gone quiet. When a prospect you’ve had real live meetings with, and that prospect showed interest, and now they’re ghosting you… It means one of two things:

1. They’re no longer interested and are too embarrassed or busy to tell you so, or

2. They’re still interested, but they’re too busy to tell you so

You can’t do anything to screw things up with the folks who fall into bucket one: They’re already not interested. The folks in bucket two remain interested, maybe are even ready to ink the deal — but you’re not the top priority.

Ideally, though, you’re your own top priority.

So you have to nudge these folks. A month and a half ago, I had someone email me “Agreed! Let’s do it.” in response to a proposal I’d sent. I sent paperwork their way that same day for signature.

Two weeks later, I nudged them. Dead silence.

A week later, I nudged again. Except I did it eight days later so they wouldn’t think I’d set a weeklong reminder. (Which is precisely what I’d done.)

Six days after that, I sent a still friendly but slightly sterner email. It was short. This was it, verbatim:

Wanted to check in once more on if you’re still looking to lock in the quarterly consulting work. Thanks for any update!

Not brusque, but not warm. I first wrote — and then edited out — an additional sentiment, that I needed an answer by end of week, so that I could know if I still had Q4 hours I could allocate. It’s true, but felt too salesy to me, so I didn’t include it. I ended up with a version of my email with a near-100% success rate.

I received the signed contract six hours later.

This now-signed client definitely wanted to work with me, and had been clear about it — but is also busy running the day-to-day at his company, swamped with work. Getting that contract inked was hugely important to me, but only moderately important to him. I know sending a third email on top of two prior unanswered ones is pushy or annoying, but I also know that if I don’t get a signed contract, I haven’t closed the deal.

So I annoyed this contact a few times, past the point of my own comfort, to make sure I stayed top of mind and got the signature. He knew I was annoying him, and he knew why — but he respected the fact that I did it as politely as possible.

Anyway… go try out my Connections puzzles? 😂