I Fed the Entire Boardroom and Other Wild Client Engagement Moves

Because nothing says ‘customer trust’ like emotional honesty and lunch with corporate frenemies.

If we're being quite honest with oureslves, darlings, most customer engagement strategies are about as exciting as a group project in business casual. We’ve all been there. Whomst among us hasn't slapped a calendar invite into Outlook and hoped someone shows up, or ran a QBR that felt like a funeral, or asked a client if they’ve “had a chance to review the deck” while your soul evaporates.

But some of us? Some of us decided to get weird with it.

I’ve built trust over client therapy calls, hosted Zoom story time for the kids of my clients during early pandemic lockdown days, and once helped a stakeholder plan a solo anniversary trip to Miami for a husband who had died five years prior. Because that’s the thing. They remember how you made them feel. And sometimes, unhinged engagement creates the kind of connection no quarterly usage stat ever could.

So if you’ve ever felt like your energy might be “a little much” for client success... EXCELLENT. You’re in the right place.

Here are my most chaotic engagement ideas: the ones that made magic, and the ones that exploded in full public view.

✅ 5 Weird Engagement Ideas That Actually Worked

1. The Surprise Project They Didn’t Ask For

I went full detective mode: pulled quotes from their CEO in interviews, read through their recent funding press, and looked at their product launch roadmap. Then I built something they hadn’t even thought to request yet. It showed I understood their world before they taught me about it, which changed the energy of our relationship immediately. Suddenly, I wasn’t just a vendor. I was a partner with a POV. They didn’t ask for the project, but they asked me back.

2. Make the Scrappy One a Star

This one’s personal. I like to find the scrappy, under-resourced (maybe last on the leaderboard) team member and invest in them. I show up consistently. I troubleshoot with them. I turn them into the their team's oracle. And guess what? That person brings the whole team along. Internal adoption goes up, they look like a genius, and the org connects that success back to our work. That’s trust currency you can’t buy.

3. Monthly Client Therapy Sessions™

Sometimes the best engagement is just… human. I had a client who never wanted to look at data, but she always wanted to talk. We talked about her team, her life, her vacation plans. One time we spent half a session planning her anniversary trip, knowing full well her husband had passed away. We booked a whiskey tasting, a spa day, and ordered a few books. It was real. It mattered. And when she did need help, I wasn’t a stranger. I was her CX therapist with a dashboard and Google.

4. Boardroom Bribery, but Make It Chic

I once sent a catered lunch to an industry association board meeting full of my clients' leadership - all of whom were also competitors. Yes, you read that right. I fed the sharks. On the menu: sandwiches, sparkling water, cookies, and a little card that said, “Enjoy your lunch! XOXO” I didn’t join the meeting. I didn’t pitch a deck. I just fed them and let the food do the talking. The impact? Legendary. One called me later and said, “That was the best vendor move I’ve ever seen.” Because sometimes engagement isn’t about what you say. It's how you feed the chaos.

5. The Strategic Meme Drop

Timing is everything. I keep a stash of custom, niche memes ready to go: stakeholder drama? There’s a meme. Slow adoption? Meme. A perfect reaction image at just the right moment breaks the tension and makes you feel like a real humann, ot just someone with a license key and a usage report. One client told me, “You’re the only vendor who makes me laugh.” We did almost all of our business through memes. We renewed. Obviously. (Hi, Hannah, hunny!)

❌ 5 Ideas That ABSOLUTELY DID NOT Work

1. The “Let’s Just Get Time on the Calendar” Move

You know what clients don’t need? Another vague invite with a default Zoom link and no agenda. When I did this, I got no-shows or 10-minute awkward silences. I thought “being proactive” was enough, but without context, clients don’t know what to prepare for or care about. There’s nothing engaging about mystery meetings unless you’re planning a surprise party. Spoiler: I wasn’t.

2. Coming in HOT

Ohhh I’ve done this one more than once. Imagine rolling into a kickoff like it’s an improv show, cracking jokes, using the word “iconic” twice, and realizing… they are not amused. Sometimes your client wants chill, spreadsheet energy - not glitter cannon vibes. Learning to mirror tone, pace, and polish is part of being good at this. You can always bring the sparkle later. But if you scare them off in the first 5 minutes, there won’t be a later. Part of your magic, my radiant ravioli, is knowing when to bring the fireworks and when to bring the flashlight. It’s not about being the most unhinged in the room. Chaos with purpose, darling. That’s the vibe.

3. Over-automated Follow-ups

I once set up a drip sequence of “just checking in” messages that sounded like they came from a bot that shops at Banana Republic. Clients ignored me. One even replied, “Did you mean to send this three times?” Engagement has to sound like you. If your follow-up feels like a marketing email, you’re not following up, hunnies, you’re ghostwriting your own irrelevance.

4. Asking for Homework Too Early

“Can you fill this out before our call?” seems reasonable until you realize they don’t even remember your name yet. I made this mistake early on a few times (listen, sometimes I have to fail a LOT to learn). I sent pre-call forms to teams who had no context, no incentive, and no connection to me. Unsurprisingly, they didn’t respond. Engagement has to feel earned. You can’t ask them to do the work until you’ve proven you will.

5. Treating Every Client the Same

I once tried using the same engagement flow for every client in my book. I automated the same cadence, same check-ins, and same templates. And guess what? Half of them checked out. One size fits all is a lie. You need to flex. You need to ask, “What does this team need from me?” and build from there. You can template a process, sure, but you customize a relationship. ✨ Final Thoughts: Try Weird Sh*t

Customer engagement isn’t a formula, sweeties. It's full-on performance art. It’s you, tossing a boa over one shoulder, flinging strategy like glitter with the other, and stepping into the spotlight with a perfectly-timed pause before saying, “I made this for you.” It’s bold. It’s weird. And when it’s done right, it’s unforgettable.

Sometimes the weirdest ideas work. Sometimes they bomb so hard you need a full vibe exorcism.

But you’ll never know if you don’t try. So weird it up. Meme it out. Plan your client’s anniversary trip if that’s what earns the trust. Just don’t send another “circling back” email and call it connection. Puh-lease.

Now it’s your turn, my precious popsicles. What’s the most unhinged engagement idea you’ve tried that worked? What strategy absolutely tanked and lives rent-free in your cringe memory? Drop your best, worst, weirdest, most chaotic moments.