People judge the average of your achievements, not the cumulative

With averages, mentioning too many items can actually reduce your overall perceived value.

👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer. For more, check out my intensive course on Executive Communication & Influence.

⛑️ Welcome and thanks for being here! If you’re looking to dramatically improve your communication and leadership, I typically work with tech leaders on: managing up to a CEO/SVP, strengthening your executive communication, and delegating to a team of ICs while raising the bar. If you’re interested in how I can support you, learn more about my coaching approach.

I originally published a version of this essay in May 2020. If you find it helpful, please share with friends. Enjoy.

Read time: 3 minutes

---

When we want to impress, we often feel the urge to name every single thing we’ve done.

Every skill we have.

Every client we’ve ever worked with.

Anything we’ve attempted.

We think the more we add to the list, the greater our accomplishments will seem.

But more isn’t always better. Sometimes it’s actually worse. Why?

People judge us based on the average of our accomplishments, not the cumulative.

With averages, adding items can actually reduce your overall perceived value.

Focus on highlights

People have terrible memories and short attention spans.

At a networking event, stick to one or two things that people can distinctly remember about you.

Instead of listing every client you’ve worked with, mention the most famous ones. People will assume the other clients you worked with were just as famous—you just didn’t have enough room to list them.

Talk about how you’ve been an avid skier for 23 years. Don’t mention that you are also a beginner in woodworking.

To be sure, the fact that you’ve been carving woodblocks for the past six months is an interesting conversation topic. You should absolutely mention it if you’re looking to find common ground with others.

But in situations when you want to impress with your accomplishments, leave it out. Focus on the fact that you’ve been doing Brazilian Jiu Jitsu since you were 4 years old, you’ve won championships, and toured the world.

✅ Average: 3-time world champion in Brazilian jiu Jitsu, computer science major, fluent in French

🚫 Cumulative: 3-time world champion in Brazilian jiu Jitsu, computer science major, minor in political science, beginner at watercolor painting, fluent in French, beginner at choir singing, beginner at the trombone

What if you don’t have jaw dropping achievements?

You have more to be proud of than you think. Anything that would be shocking, surprising, or piques curiosity is fair game to include.

Another example: Let’s say you want to talk about customers you work with.

✅ Average: Worked with Stripe, Meta, Notion

✅ Conclusion: Listed 3 things. All 3 were strong. So 100% strength.

🚫 Cumulative: Worked with Stripe, widgetsforcheap.com, Meta, cogsandwidgets.com, Notion, morewidgets.co, widgets4u.com

🚫 Conclusion: Listed 7 things. 3 were strong. 42% strong. Some are strong but others sound spammy. Not sure how legit you are.

The exception is if you want to humanize

Famous leaders will often mention what they’re bad at because they want to appear relatable. When a head of state or CEO says they are terrible at physics, but love watching YouTube videos about it, it doesn’t diminish their power. It just makes them seem more approachable, and therefore more likable.

So if you want to seem relatable, you can talk about what you’re not great at. But makes sure you do this intentionally and sparingly, because in general, people like being on the same team as winners. More on the problem with glorifying failure.

The next time you’re debating whether to include one of your accomplishments or hobbies, ask yourself: Would this increase my average?

Have you experienced the urge to list everything you’ve done, every project you’ve ever touched, and every skill you have? How is this making you think differently about how you talk about your accomplishments?

Hit reply because I’d love to hear from you. Thanks for being here, and I’ll see you next Wednesday at 8am ET.

Wes

---

Connect with Wes

• Are you new to the newsletter? Subscribe for free

• Follow me on LinkedIn for more insights

• Learn more about 1:1 coaching to improve your executive presence and communication

• ✨ The new July 2025 cohort is now open: Improve your ability to sell your ideas, manage up, gain buy-in, and increase your impact in an intensive 2-day workshop. Save your spot here: Executive Communication & Influence for Senior ICs and Managers