🐋 How to message your boss

The etiquette and expectations you might not know. Breaking News: Salesforce just released Summer '23 internships, check them out here! Plus, full-time gigs @Plaid, Credit Karma, Cribl, and more!

Tech Pod

Sep 15, 2022

Hello, Tech Pod! 💦

How and when to message your boss is one of those things that you aren’t taught – but are expected to know anyway.

We’ll make a bet you’ve had these thoughts ⬇️

“Should I ask for help or try to figure it out on my own?”
“Why didn’t they respond?”
“Am I being annoying?”

So, this week, we’re breaking down:

When to ask for help ⌚️
How to ask for a decision 💭
What ‘no response’ means + how to follow up 💬

Let’s go! ⬇️

When to ask for help

What to consider before reaching out for help:

Can I figure this out on my own?
Can I complete this task and get help afterward?
Is this a low-risk decision I can make myself?

Best practice will depend on your manager’s style — do they prefer frequent check-ins or do they appreciate independence? You don’t have to guess or learn from trial and error, just ask them directly from the start.

Understanding their work-style will not only show initiative, but also help you in the long-run.

When you do reach out:

Keep your message as succinct as possible — present the problem clearly and contextually.
Don’t waste a message cycle with “Can I ask you a question?” Just ask it.
Don’t start with “Can we hop on a call?” Try to get an answer through DM first.

But in the end, don’t be afraid to ask for help!

When you need a decision from them

Help your boss make a decision by presenting the data succinctly — offer a recommendation they can either agree with or suggest changes to, ideally in a few sentences.

This Twitter thread explains it best:

6529 @punk6529

11/ So let's go to "how to ask for a decision" 1: What is the decision? 2. What data is needed for the decision? 3. Do you have the data? (if not, go get it) 4. What decision would YOU make with that data? 5. Do you still need to ask for a decision or did you just make it?

6529 @punk6529

12/ If you have gotten to Step 5 and you still need a decision, then the correct structure for asking it is 1: This is the decision I want 2: Here is the data for making that decision 3: Here is my own recommendation, given the data in #2 4: Please let me know if you agree

Final Words 💦

Try to just get the job done. Don’t let fear of mistakes make you dependent on continual help — but again, don’t be afraid to ask for it when it’s needed.

Don’t take it personally — short or late responses are because they’re busy, not because they’re annoyed or don’t value you.

Busy bosses have waves of messages hitting them all day — if you don’t get a response in 24hrs, it was likely lost in their sea of messages. Don’t be afraid to send them a gentle follow-up. For example:

“Hi there, <boss>,
Just following up on this – hoping to get thing rolling within the next few days, and wanted to get your opinion. Let me know when you get a chance, thanks!
<name>”

+ Shout out to @6529 for the idea! Check out their Twitter here

In the News:

VCs look to new regions – investors are staking larger claims in non-western countries 🛫

Launch House takes a fall – a Vox investigation reveals the promise to foster young founders falls short with claims of toxicity (TW: mention of sexual assault)

Designer? Stay tuned – Adobe is trying to buy Figma 👀