Picking your battles when you are hyper-rational

Don't get caught up in being technically right, at the expense of being effective

👋 Hey, it’s Wes. Welcome to my weekly newsletter on managing up, leading teams, and standing out as a high performer.

If you’re interested in how I can support you, my clients are hands-on (often hyper-rational) leaders at companies like Amazon, Product Hunt, Vercel, Microsoft, etc. About 1/3 of my clients have technical backgrounds. If you are doing great work but need to increase your executive presence, I’d love to help you get more recognition, increase your influence, and grow your impact. Learn more about coaching.

Read time: 6 minutes

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Recently, I caught myself doing something I often see my fellow hyper-rational operators do:

Getting caught up in being technically right, at the expense of being effective. Basically, winning the battle but losing the war.

When you notice a small mistake or miscommunication, your urge might be to correct your colleague—because you are technically right. But this can derail the main point and cause a distraction.

I have to remind myself: Keep the bigger picture in mind.

I want to share an example of how this can creep into your work, with email drafts I almost sent vs what I actually sent.

These examples seem tactical because other examples wouldn’t make sense after redacting. But you can see how the underlying themes apply to bigger decisions and conversations too.

Example 1: Inconsequential details

• Situation: Confusion about time zone and scheduling

• Initial reaction: Offer multiple options based on different interpretations of what they said

• Better approach: Move forward based on the most productive interpretation of what was said

• Takeaway: Shift from proving they communicated poorly to getting the call scheduled

Recently, I got a note from a recruiter who wanted to do a reference check on one of my former direct reports. The email is strong, but there was one part that was slightly confusing.

Here’s the email I received:

🚫 Here’s what I almost sent:

Hey [redacted] and [redacted],

It's great to meet you. Yes I'd be happy to speak about [candidate].

My time zone is ET. You mentioned [hiring manager] can speak this morning because he’s based in the UK, but it’s 7pm UK time at the moment. Did you mean he can speak on Saturday morning ET / evening UK time?

Ideally we can sync today instead of Saturday. If we want to sync today, I can speak at 2-3pm (now-ish), 4:30pm, or 6pm ET.

Let me know which one of these times works for [hiring manager]. If he can’t speak today, happy to sync with your recruiter too. Looking forward to it.

Wes

^ The recruiter said, "[The hiring manager] is based in the UK, so would you be available for a 15-minute call this morning? And could you confirm your time zone?"

I was confused because when I got the email, it was almost 1pm ET.

(Looking back, the recruiter was probably based in PT, and was referring to their morning—not my morning, or the hiring manager's morning.)

I found myself wanting to clarify the confusion.

Even if I'm technically correct, should I explain potential interpretations for something so inconsequential? What's the upside?

There was no upside.

✅ Here’s what I actually sent:

Hey [Name],

It's great to meet you. Yes I'd be happy to speak about [candidate].

My time zone is ET. Today, I can sync at 2-3pm (now-ish), 4:30pm, or 6pm ET.

Let me know which one of these times works for [hiring manager] or your recruiter. Looking forward to it.

Wes

^ This version is much better. It’s crisp and concise. The goal is to figure out scheduling, so let's figure that out as fast as possible.

This email took about 5 minutes end to end, including rewriting what I had earlier. Once you catch yourself, you can edit pretty quickly.

More on how to share the right amount of context.

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Example 2: Too much backstory

• Situation: Finance team mixing up which platform/forms to use

• Initial reaction: Urge to explain context and backstory

• Better approach: Confirm the right path and move on

• Takeaway: Shift from explaining what caused the confusion to confirming the solution

Here's another example of catching myself before over-explaining in a direction no one cares about:

After signing on a new client, I got connected with their finance team. A day later, I received an automated email asking me to set up my vendor billing profile.

The link was broken, so I asked for a new one. I said:

Their reply:

At first, I was a bit frustrated.

The only reason I thought I needed access was because their system sent me an email saying I should fill out my information in the portal.

Luckily, I caught myself and realized: Adding context about why I was confused doesn't help anyone.

🚫 Here’s what I almost sent:

Hi [Accounts Payable representative],

Thanks for clarifying I don't need to fill out Coupa because you have my W8-BEN-E. Yesterday I received an email from Coupa saying I should fill out the form, so I didn’t realize I didn’t need to do it until now.

Apologies if I misunderstood–I was onboarding with a few new clients this week, some of who use Bill.com, Coupa, Tipalti–so I've been getting a few requests to fill things out and might have gotten my wires crossed.

✅ Here’s what I actually sent:

"Great, thanks for clarifying that we don't need to use Coupa here."

I’m glad I spared my recipient (and myself) from all that useless context. The final note is simple and focused.

More on how to avoid backstory scope creep.

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You might feel compelled to demonstrate that you noticed and understand all the nuances of a situation…

But ask yourself if there’s any real value in doing so.

Resist the temptation to call the person out for using confusing language. If you point out how their message could have multiple interpretations… YOU could end up looking like the one who is causing confusion.

And you’ll probably spend more time figuring out how to articulate their mistake than it would take to simply move on.

Obviously, there are times when you really do need to clear up confusion. But if it’s something minor and inconsequential, I remind myself to let it go and focus on achieving my main goal.

Ask yourself:

• Is this explanation moving us toward the goal?

• Will this context help the other person, or simply prove that I'm correct about something that doesn’t matter?

• Am I serving the conversation, or my ego?

Would you describe yourself as having hyper-rational tendencies? 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

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