👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, career growth, and standing out as a high-performing leader.

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Read time: 2 minutes

A few years ago, I was assessing take-home projects for senior marketing candidates. My coworker was the hiring manager, and sent me a few candidates he was excited about.

One candidate shared a slide deck. When I clicked on it, my first thought was, “Ooh.” But upon reading, I quickly realized the ideas were basic, generic, and didn’t show strategic thinking.

Another candidate submitted a Notion doc that included a fancy table. Upon reading the doc, I realized the candidate spent 80% of the project discussing operational details, like a milestone calendar for a mock launch.

That wasn’t what the prompt asked for. The prompt asked for strategic insights, assumptions, and what they would do—not how they would plan the logistics. At the level we were hiring for, I assumed they knew how to project manage and didn’t need to test for this skill.

I consider myself a skeptical person, so I was surprised at how much benefit of the doubt I gave the projects at first glance simply because they displayed the right aesthetic.

A shiny doc that offers little substance is still useless.

When my direct reports sent me a well-organized Notion doc, my immediate reaction was often, Ooh this looks great.

Upon reading, the mileage varied. Sometimes the content was excellent; other times, the docs lacked insight. But in all cases, my initial response was more optimistic because the doc was visually appealing.

Most of us know that poor formatting can make a good idea seem less attractive. But we don’t often talk about the opposite: Good design can be just as dangerous because there’s a halo effect: It looks good, so the ideas within must be good.

In the past, Google Docs or Microsoft Word was less forgiving because you only had cold, hard text. If you wrote in prose, you had to create a compelling narrative supported by evidence, and create connective tissue between ideas. There were fewer places to hide.

Now, with tools like Notion, the default is content is easier and more pleasant to read—with well-designed headers, call-outs, toggles, emojis, bullets, etc—but this doesn’t replace high-quality insight and logic.

This is the same reason why I dislike when people are overly-reliant on templates. Just filling out a template for a strategy doc doesn’t mean anything. It might look decent from far away, but up close, the seams and messiness show. I’ve often advised my team to put away your templates for a minute—step away from trying to fill in each section, and first, think and develop conviction.

To be clear, good design and good content isn’t mutually exclusive. Use the appropriate level of skepticism when you evaluate well-designed documents. The goal is to accurately assess what you want to assess, and this means being aware of potential cognitive biases and not being distracted by noise.

Personally, if given the choice between the two, I’d rather see a simple text-only strategy doc that's dense with insight, rather than something well-designed with mediocre content.

New podcast episode

Recently I was a guest on Justin Norris’ RevOps FM podcast and loved how thoughtful his questions were.

We talk about:

• Why I’m fascinated by topics that are deceivingly basic, and why nuances matter

• Rigorous thinking as a force multiplier, how to cultivate a culture of rigorous thinking, and reasons people struggle with it

• Managing up and using “bottom line up front” (BLUF) in communication

• How to get the right level of feedback from your manager

• Being vulnerable vs perception management 

• Managing others: setting expectations and inspiring autonomy/ownership

Check it out. I’d love to hear what you think.

One of my favorite parts of this newsletter is hearing from you. If this post is resonating and you’d like to share a story/example from your own work, hit reply or share in the comments.

Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

PS If you found this valuable, here are more ways I can help:

1. Follow me on Twitter or LinkedIn for insights during the week (free).

2. Book me as a keynote speaker to level up your team.

3. Work with me directly for 1:1 executive coaching. I find it extremely rewarding to get into the specifics and give personalized guidance to ambitious leaders on unique aspects of their situation.