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status update, therapy sess, blocker removal, which is it?!
I Hate It Here
Hebba Youssef
Jul 27th, 2026
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Hiii y’all,

I cannot believe how fast summer has flown by! I don’t feel like I’ve gotten enough time outdoors so I will need to remedy that ASAP.

Next week I’m OOO but don’t worry I’ve prewritten my newsletters so you’ll still get your burst of joy in your inbox while I am getting my dose of required sun. <333

Here are some things guaranteed to bring you joy RIGHT NOW:

🎧 This week episode is FIRE. On the mic is someone I’ve loooong admired, Aubrey Blanche!! She’s a badass who is getting a Master’s in AI ethics & society at Cambridge so naturally we get into the ethnical impacts of AI and you do not want to miss this discussion. We laugh, we cry (jk), and I def walked away learning a thing or two!

📺 TOMORROW ON HR Therapy… how will (or will not) your workplace transform with AI? I get into this and more with a brilliant panel of transformation experts who are working with some of the biggest names in the biz to figure out how to reshape workplaces due to AI.

Now, onto today! This quarter we’re in builder mode so every week we’re either improving things or tearing them down. And on today’s list is manager 1:1.

Fun fact: the first book I told one of my old direct reports that I wanted to write was about managers. This past week she read me for filth and stated, loudly, IN 2019 you said you would do this, so where’s my book to read?? I used that inspo to write this week’s newsletter… ILY!!


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Download it for free, and let today be the day you stop winging it!


Builder Mode

Doing too much?

Last week I told you engagement surveys are a rebuild and to scrap the annual check-in for lightweight, continuous listening instead.

And in there, I specifically called out 1:1s as part of the fix!! Managers doing regular check-ins, asking better questions, actually flagging things upward instead of waiting for a random review or survey to surface the issues.

I stand by that. But I've been noodling on something since I hit send…

As a managee (is that even a word? spellcheck says no, I say too bad, we're using it), a lot of my 1:1s have been... fairly useless.

Here’s why: we’re trying to do too much in 1 convo! We've asked one 30-minute meeting to do the job of FOUR different meetings.

Think about everything a 1:1 is supposedly supposed to cover:

  • A status update: what's happening, what's blocked

  • Problem-solving: help me think through this thing

  • Connection: how are you actually doing, as a human

  • Career building: where am I going, what's next for me

Cool cool cool, all of that, in 30 minutes…

Yeah right.

🛠️ So, in this week’s edition of Fixer Upper: Work Edition the elusive and magical manager 1:1.

We’re gonna improve them and here’s how!

Improving your 1:1s

Genuinely… steal this section and send it straight to your managers!!!!

This might be the advice they need? And frankly, you’ve probably already given it.

1. Stop cramming it all into one meeting. There is not one kind of 1:1.

✔️ There are at least four: status, problem-solving, connection, and career. Trying to hit all four every week is how you end up with a meeting that technically covers everything and actually accomplishes nothing.

Pick which job this particular 1:1 is doing before you walk into a meeting AND make sure the managee (I’m making it real word) knows what type of meeting it is before they walk in too.

A suggested cadence, if you want somewhere to start:

  • Status: weekly. This is the one that actually benefits from routine.

  • Problem-solving: in the moment, as it comes up. Don't save a blocker for Thursday's meeting if it's blocking someone today.

  • Connection: also in the moment. This isn't a scheduled agenda item, it's a "how are you, actually" that should show up naturally, not just once a week!

  • Career/growth: monthly, at minimum. This is the one that gets skipped first when time's tight, which is exactly why it needs a floor.

👀 Protip: Rotate the focus instead of trying to cover everything every time. This is the actual fix for "too much crammed into one meeting": don't try to!! Rotate which job the 1:1 is doing, status-focused most weeks, a connection-focused one monthly, a career-focused one quarterly. Not every 1:1 has to be everything everywhere all at once!!!! It just has to consistently be something real, on a schedule people can count on.

2. Give your managers actual structure, not just a calendar invite. "Have good 1:1s" is not a strategy! Managers need a simple template for each type, a few prompts for the status ones, a few for the career ones, a few for the "how are you really doing" ones so they're not improvising cold every single week. This is probably the least glamorous but most necessary tip on this list!

👀 Reference the questions from last week for help with templates.

The HR of it all:

Okay, so what's our part in this, other than handing managers a template and walking away???

Here's the part that actually matters: what surfaces in these 1:1s, and how it makes its way to HR.

Now, I am, in no way, saying HR needs to know everything that happens in every 1:1. Honestly? Ew!!

Nobody wants that, least of all HR, who does not have the bandwidth to be a fly on the wall in every single check-in across the company. It also feels more like spying than actually helping!

There’s range between "HR hears everything" and "HR hears nothing until it's a resignation email" Somewhere between those two extremes is where we can actually be helpful.

By giving managers a real, low-friction way to flag the things that matter like the employee who mentioned they're not being challenged and are looking for new opportunities, the team that's quietly falling apart, the burnout that's moving towards a resignation without turning every 1:1 into a weird form of a surveillance report.

That's the piece worth building. Not a system where HR is copied on every conversation. A system where the right things actually make it upstream, instead of getting stuck in a meeting that was never built to carry them in the first place.

Here’s a lightweight way to do this:

Give managers three flags, not a form. Not a survey, not a spreadsheet, not a "please document your 1:1 notes here" ask nobody will keep up with.

Just three simple categories a manager can mentally sort what they heard into:

🟢 FYI: nothing needed, just context in case it matters later ex: "mentioned they're planning a wedding, might need flexibility in the spring.”

🟡 Keep an eye: not urgent, but worth knowing exists ex: "said they're feeling stretched thin," "hinted they're bored."

🔴 Need support now: actually urgent, this is the resignation-in-progress or employee is about to break situation.

Only the yellow and red flags actually go anywhere!! Green stays with the manager, yellow and red get a two-minute note to HR, not a meeting, not a form, just a Slack message or email with:

  • Who

  • What flag

  • One line of context.

Our job is to pattern match. One yellow flag about feeling stretched thin isn't a crisis per se. Five yellow flags from the same team in a month is info nobody would've caught from an annual survey!!

TBH: You don’t need new software, new meetings, or even a new dashboard.

Just a shared, dead-simple language for "does HR need to know this or not" so the right things travel upward, and everything else stays exactly where it should: between a manager and their report in their 1:1.

Okayyyy. That's the verdict… 1:1s are an improve!

Agree? Disagree? Have a topic you want me to cover?

Reply to this email on a topic of your choice that you want my take on improve, rebuild or tear down.

This could get fun…


(HUMAN) RESOURCES


WORK-LIFE BALANCE

  • 📚What I’m reading: Dungeon Crawler Carl by Matt Dinniman. This has been popping up everywhere recently so I decided it was time for me to read as well.

  • 📺 What I’m watching: Maximum Pleasure Guaranteed on AppleTV. This had me hooooked from episode 1 and I'm in so deep. I watched the whole show in ONE DAY. If you watched, let me know!!!

  • 👋🏽 What I’m obsessing over: Safe Space Summit speaker announcements. I've got the most epic lineup and I'm pumped to share more soon!!!


Sponsored by eSkill

Did you know a bad hire costs ~30% of the employee's first-year salary? 😮

Talk about ugly math!!!

There's even more of an impact that doesn't show up on an invoice, like burned-out team members covering the gaps, and managers babysitting instead of leading.

eSkill has a new article that breaks down the FULL cost of a bad hire, so you can catch the warning signs before they cost you a strong performer's patience!


SONG OF THE WEEK

🎧 Stupid Song, Olivia Rodrigo

I CANNOT GET THIS SONG OUT OF MY HEAD!!!!

The line → I feel right, I feel wrong, I feel totally insane

^^ me every time I've been in love.

Or during any minor inconveniences

IM A PISCES OKAY.

ALSO her breathe control is wild!!!! Are you loving this new album or just me?


I hope you enjoyed this, please let me know what you think and what other topics you'd love for me to cover. I'm allll ears.

Reminder: Take care of yourself and know that I support you.

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