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Can your copy be strategic AND clever?

I came across a quote that sent me into a strategy-induced existential crisis (in a good way):

Luke Sullivan, Hey, Whipple, Squeeze This

Now, we've all heard the 'clear over clever' mantra in copywriting until we're blue in the face. And it's solid advice! But here's what nobody talks about: the equally dangerous pull between being clever and being strategic.

Your brilliant creative ideas should never wander off the strategic path you've carefully mapped out.

I'm wrestling with this exact tension right now while working on messaging for a B2B data integration client. There's this constant dance between making copy punchy and ensuring it carries the full strategic weight of our research.

Here's what I mean:

You have a robust research report sitting on one monitor – filled with analyses on customer interviews, competitors, and your product. On the other screen, you're crafting messaging that needs to be both memorable AND true to all those insights.

You will feel the temptation of cutting copy to make it snappier. If you’ve tried, it’s inevitable. But then you glance at your research and think: "Wait – did I just sacrifice our key differentiators for the sake of being clever?"

A real example from my current project: research shows that customers see the solution as fundamental to their operations. That's a strategic insight you can get creative with. For instance, you might play with the concept of "foundations" in your messaging - exploring how your solution supports the critical infrastructure that supports everything else.

What makes messages like this work isn't just clever wordplay - it's that the creative angle emerges directly from customer research. You could express this idea in several ways:

• Highlight the meta-level support role
• Play with the recursion of enabling the enablers
• Draw parallels to architectural foundations

But each version would still tie back to that core insight about being fundamental to operations. This keeps the creativity grounded in strategy rather than just being clever for cleverness' sake.

So how do you spin the strategy without losing hold of it? Here's my process:

1. Create a simple "strategic checkpoint" list
   • Key differentiators
   • Critical pain points
   • Must-have proof points Keep it visible while you write
   • Competitor claims and promises
2. Do the "research bounce" For every key message you write, bounce back to your strategic checkpoint. Are you still speaking to what matters?
3. Watch for warning signs you're drifting:
   • Copy that could apply to any competitor
   • Clever phrases that sacrifice clarity
   • Messages that don't tie back to specific customer pain points

In B2B SaaS, our goal isn't to win creative awards. It's to connect deeply with your audience's needs while clearly communicating your unique value.

The magic happens when you nail both – strategic truth and memorable delivery.

DISCOVERY

Time to think slow

If you read one piece this week, go with this one by Scott Galloway. Speaking of having a check in with yourself and remembering to go back to your strategy, this is a good reminder to apply system 2 thinking to our work.

Scott Galloway

Welcome to the AI agentic era

Google recently announced its launch of its Gemini 2.0 models with their project Astra. Here's a quick video:

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This marks a big jump in AI tech for a lot of companies (OpenAI is doing something similar with ChatGPT advanced voice mode, same for Anthropic with Claude computer control). I tried both Gemini and ChatGPT live video stream (sharing your camera from your phone and your screen from your laptop) and a few simple test, including a "usability" testing of a website, asking the AI voice to put itself in the shoes of my ICP and tell me what it thought about the copy on the site.

It's pretty cool. Not exceptional yet but it's a great sign for what's to come.

RESONANCE

Greg Mckeown, Essentialism

Remind yourself that, in any moment, you have the power to choose your reality. Your present reality is an accumulation of past choices, shaped by your ability to remember that you can choose differently at any time.

Have a great weekend!

Cheers,

Chris

Chris Silvestri Founder & conversion alchemist

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