👋 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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Today, we’re going to cover how to give the right amount of context:

1. Remind them where you left off.

2. Be specific about what you need.

3. Mention if it’s an FYI.

4. Avoid being too detailed in the wrong ways, not detailed enough in the right ways.

5. Consider these variables to give more or fewer details.

6. Mention your criteria and assumptions.

7. Aim for the minimum viable backstory.

8. Main point at the top, context below.

9. Give a concise answer, then offer to elaborate.

10. Ask yourself what your manager will likely ask you.

I originally published a version of this essay in October 2019. Since then, I’ve expanded the post. If you find it helpful, please share with friends. Enjoy.

Read time: 8 minutes

Giving the right amount of context helps teams move faster.

Too much context? Your manager can’t tell what’s important. They’ll need to wade through details, trying to sort information into a pile of what’s important vs what to ignore.

Too little context? Your manager has to follow up and pull information out of you that you should have mentioned proactively. There is such a thing as being too concise.

When you share the wrong level of context, you waste time on:

• Needless back-and-forth

• Avoidable follow up questions

• Misunderstandings and confusion (“Where are you going with this?”)

High-performing operators are exceptional at communicating and managing up. This is even more important in remote environments.

This begs the question: How do you give the right amount of context?

1. Remind them where you left off.

Task switching takes a tremendous amount of energy. Your manager is probably reading your note in between meetings (or during one!). Assume they’re reading with partial attention. Remind them where you left off so they can task switch faster.

🚫 “Here’s the updated link.”

✅ “Here’s the updated pitch for X customer. I incorporated your feedback and included a change summary below. Let me know if you have any questions. I’ll plan on shipping tomorrow morning.”

You can top it off by saying, “Let me know if you have any other feedback. I’ll proceed unless I hear otherwise.”

This makes it super easy for your manager to quickly say, “Looks great, thanks.”

2. Be specific about what you need.

Years ago, I had a paid ad agency vendor say this in Slack:

“The new ad is updated in our Google Doc. It’s published in Facebook as well, but not running.”

What’s wrong with this statement?

When I read this, I don’t know if:

• Is the FB ad not running because something is broken, we got flagged, or something else terrible? Should we be worried? And if yes, what are you going to do about it?

• You updated the Google Doc. Now what? Is this an FYI or are you waiting on something from me?

Don’t assume your manager knows what you need from them. Be specific about what you need and what the next step is. Otherwise, they’ll assume you’re making progress–and will be surprised to find out you’ve been stalled for weeks.

🚫 “The new ad is updated in the Google Doc. It’s published in FB, but not running.”

✅ “Please approve the new ad copy (screenshot below). Once you approve, I’ll publish and go live on FB.”

3. Mention if it’s an FYI.

Folks think they’re being helpful by forwarding a random email. But without context or next steps, these messages are useless. Don’t make people guess if they need to take action. If your recipient has to follow up to ask why you sent this, you’ve already slowed everyone down.

🚫 [No context]

✅ “FYI. Sharing because you mentioned wanting to see examples of X.”

4. Avoid being too detailed in the wrong ways, but not detailed enough in the right ways.

Details aren’t the problem. The problem is too many of the wrong details. This is mostly about the content of your argument, not the structure, so it’s hard to discuss without real examples that would be meaningless after redacting.

Let’s say a customer asked why they got fewer students from the second cohort of their course. You could say this:

🚫 “Consider extending the enrollment period. For cohort 1, your course was announced on May 13, providing 6 weeks to accept students, up until the August 1 start date. For cohort 2, you announced the course on October 7 and only accepted for the following 10 days.” ← This is confusing.

✅ “Consider extending your enrollment period. For your first cohort, you had 6 weeks to fill the cohort. But for your second cohort, you only had a bit more than 1 week. So next time, I recommend giving students more time to sign up.”

Notice how too many of the wrong details distract from the main point:

• Too many numbers: cohort 1, May 13, 6 weeks, August 1, cohort 2, October 7, 10 days. Numbers attract the eye, but too many of them add cognitive load—it’s hard to tell what numbers to pay attention to.

• This is not just about shortening for the sake of shortening. This is about clarity. The main point of this paragraph is to say: You had 5x as much time to fill your first cohort.

• Providing is one word, but clarity overrides conciseness. Saying “you had x days” reads more easily than providing x days.

How do you tell what details to include? In this example, your recipient doesn’t need to know the exact dates of when the course was announced and when applications ended—they need to know the rough amount of time they were accepting students.

Consider what the person needs to know vs what’s secondary. Every detail adds cognitive load for your audience because they need to discern what’s important.

Now that you have this vocabulary about “too detailed in the wrong ways, not detailed enough in the right ways,” watch out for it in your own writing and help point it out in your peers’ writing.

5. Consider these variables to give more or fewer details.

Giving the right amount of context is hard because what matters to you isn’t necessarily what matters to your audience. So when in doubt, put yourself in your recipient’s shoes.

If the decision involves spending money or is customer-facing, err on the side of giving a bit more context. Customer or public-facing material affects your brand, and could lead to much bigger snafus, so it’s a higher stakes decision.

What’s the magnitude and longevity of the impact if things go wrong? Do we lose a few hundred dollars—or are we signing a 5-year legally-binding contract?

You can share LESS context when…

• You’ve made this type of decision many times and you have task-relevant maturity

• The decision is relatively cheap and reversible

• This is top of mind for your manager—not one of 25 projects they’re managing

Aim for MORE context when the decision is…

• Irreversible and expensive

• Customer-facing or public

• You’re making this type of decision for the first time

6. Mention your criteria and assumptions.

Most managers want to know that you did your due diligence and that you’re thinking ahead.

Let’s say you need to recommend a new platform or tool. It’s not that helpful to simply send your manager a list of software tools. If you do that, they have to do the hard part of comparing the options, analyzing, and deciding what to do.

When you show your thought process, your manager can point out gaps in your logic–or share information you’d find relevant.

🚫 “I recommend this platform.”

✅ “I recommend this platform because of XYZ criteria. The potential trade-off is A, but seems manageable because B. I vetted options, including [insert options] but thy didn’t seem ideal because [briefly mention why they weren’t ideal]. I chose [my recommendation] because it better fits our needs.”

The above format is extensible, meaning you can use this structure to explain your idea in 3 minutes or 30 minutes.

7. Aim for the minimum viable backstory.

Tell me if you’ve told a story like this:

🚫 “So I was meeting up with my former coworker on Thursday—no wait, was it Thursday? It must have been Wednesday because I went to Costco that morning, and that was the only morning I could stop in before work. Oh as I was walking to check out, I saw they had those keto bars and I normally would have gotten them, but I’m trying to avoid processed food. Anyway, I met up with them and…”

We’ve all been guilty of speaking like this with friends, but at work, this can make you look scatterbrained.

Backstory scope creep is real. You start with the intent of sharing only the basics, but before you know it, you’ve gone down multiple tangents—and you’re embarrassed to admit you forgot the original question!

It’s hard to be concise when you’re trying to process information, decide what to share, and speak the words—all in real time. By the time you realize you’ve shared too much context, you’re already in rambling territory.

The solution: Don’t try to do multiple cognitive steps at the same time. Take a few beat to gather your thoughts, and when possible, prepare a few high level notes for yourself.

More here: Start right before you get eaten by the bear.

8. Main point at the top, context below.

This is one of my favorite ways to structure messages because it gives your reader agency. You let your recipient read as much or as little of the context as they need.

The key is to visually put the context separately. This creates an obvious demarcation between the main point vs the supporting context.

Personally, I love this structure because your final recommendation and supporting rationale are often equally important. Sharing your logic gives you more ammo to convince your reader.

🚫 [Actions, backstory, and context all jumbled together]

✅ [Main point at the top, context below]

9. Give a concise answer, then offer to elaborate.

Offering to elaborate lets your manager chime in and tell you what kind of context they want. The key is to provide a brief list of options:

• This makes you look strategic and shows you were thoughtful about the decision.

• This makes your manager’s life easier because you give them something to build on or push back on.

You are the expert here, so you should try to drive the conversation, including what questions you think they should be asking.

🚫 “I can elaborate on anything.” ← This is not helpful.

✅ “I can elaborate more on a few areas: For example, the other options I looked at, including (a) if we optimized for speed and could get this done in a week, (b) cheaper/more expensive options that I thought weren’t worth it, and (c) looking ahead a few steps, the risks I foresee and how I’m planning to derisk.”

10. Ask yourself what your manager will ask you.

What questions does your manager usually ask? Answer those questions yourself. If you take anything away from this article, make it this.

Every manager has their own idiosyncrasies, worldview, values, etc.

That’s why the best thing to do is to pattern match. Consider what they’ve asked you in the past, when talking to you or others. Try to give context through that lens. Ask yourself:

• What questions does my manager usually ask?

• How much detail—and what type of detail—does my manager usually want?

It's your job to do the heavy lifting. By providing the right amount of context, you’ll take the mental load off your manager and you’ll shine as a high performer. Win-win.

Which of the items in this list do you already do? Which do you want to do more of?

One of my favorite parts of writing this newsletter is hearing from you. If you’ve applied what I write about and would like to share a story/example, hit reply or share in the comments. I’d love to hear about it.

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

Wes

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