Hold On, Let Me Overthink This

Jessica MacGregor • March 27, 2026

In business as in life, complexity is not doing you any favors.

A couple of weeks ago, I caved - big time. I started playing a couple of daily LinkedIn games.


I played one; it took 12 seconds. I came in second place against some of my connections who are much more accomplished than me in real life. And that was on the first try! (Take the wins where you can, right?)


I discovered my favorite was the Mini Crossclimb. If you aren't familiar, it's kind of like a cross between a crossword and Mastermind. (I'll spare you the details, because they're beside the point.) The real point is that I slayed at that game for all of about two days.


But then something funny happened - I got worse.


Instead of focusing on the clues in front of me, I found myself looking at the other words I'd already guessed, trying to get one step ahead. I started thinking about words I'd used in the past. My mind started wandering to what the final two-word answer might be.


I went from running on instinct to overthinking. And it happened fast.


In Business, As In Life...


Something similar happens when you're building (or joining) a company - especially in high tech. Out of the gate, you immediately see/categorize/distill the business value. You win your first customers.


But then you start going deeper. Really understanding the tech. Pushing its limits to see what it can do. Exploring other ways it might help customers - perhaps even pushed there by customers themselves. I believe the technical term is "drinking the kool-aid."


Suddenly, something you started into clear-eyed gets more complex and nuanced. And actually, that nuance is beautiful and exciting. It's where innovation happens, and it's what makes innovators stick with a company over time.


The problem is that this nuance begins seeping into your communications. Your one or two line value prop turns into an overly-technical web as all of your "benefits" fight for attention. When you try to streamline that value prop again, you end up watering it down with values that any company can claim - like "save time and cost" or "simplifies XYZ".


The Messaging Crossroads


At this inflection point, companies typically go one of two ways:


  1. Supersize Tech Support - Call up the smartest people in the room: the top execs and team building your product. These are the people that understand your product better than anyone else. The problem? They understand your product better than anyone else. They aren't seeing through the fresh eyes of someone new to your brand.
  2. Abstract To Oblivion - Overly focus on the high-level benefits of using your product (see the "save time and cost" example above). Benefits aren't the value you provide. They may be the end result, but they are not what makes your product valuable. Prospects may look at your boilerplate and still have no idea what you offer.


Needless to say, neither extreme makes for great messaging. Often they even do more harm than good. In the best case, you confuse time-strapped executives so they put you on a back-burner (which they'll never have time to revisit). In the worst case, they write you off completely - which is a larger hurdle to overcome.


What In The *Comms* Should We Do?


Yes indeed, this is where trusted communications counsel should come in with a wide-angle lens. The deep tech is important, and so is the high-level benefit. Somewhere in the middle is your value statement. Comms people spend their careers training themselves to see that forrest through the trees - without just calling it all green.


As you may have gleaned from my Mini Crossclimb analogy, overthinking is one of the biggest pitfalls I see with tech companies. They know too much, and so their messaging starts from there. It leaves the real-world buyer behind. There's a reason they call it a buyer "journey" - you just can't expect them to see what you're seeing right away.


Messaging is one example of where this plays out, but it has implications across the board. It might look like:


  • Random Acts Of PR - Putting out press releases expecting them to make news where there is none. Expecting journalists or prospects to care about something just because that the spotlight is flattering at that angle.
  • Blogging For Blogs' Sake - Blog posts are overly technical, serving customers more than prospects. They're navel-gazey, serving ego rather than audience.
  • The Website Reno - Overhauling your website (yet again) in the hopes that a restructure will shift your brand perception. Adding more, or conversely, taking away too much.


These all come from a legitimate need for clarity and understanding. To make your brand and its value known. But when you know too much, it's easy slip into overthinking. That's where real comms strategy makes a valuable difference. Helping guide others to see the thing you're building through your eyes.


I have another analogy like this about parent-teacher conferences, but I'll save that for another day.



If you stuck with me until now, thank you for reading to the end! For more insight into the mind of a comms person, you can subscribe my Substack newsletter, Cultivated.


P.S. Thanks to my mom for the t-shirt. She is a true icon.