OG Tuesday Issue #314

🎉 Today is The Assist’s 6th birthday!

Our very first edition landed in inboxes on September 29, 2020, and six years later we still get a little giddy every time you open one. Thank you for reading, replying, voting in our polls, forwarding us to your coworkers, and telling us when we got something wrong. You’ve shaped every single edition. And a huge shout out to our small but mighty team for helping us grow and pushing this newsletter to be better every week. We couldn’t do this without all of you, and we wouldn’t want to. Here’s to year seven 🥂.

🌿 309 lbs → 190 lbs in 7 months. No Ozempic or calorie counting. Meet the Canadian who did it with one app.

🌿 Glean’s AI search, via AWS Marketplace, finds anything across your company’s tools in seconds.

⚡ Get more done with less chaos using these productivity templates.

🪜 Changing careers after 45 left 72% of people feeling like a new person.

Forty percent of you told us getting past the ATS is the hardest part of job searching. The software is less of a robot bouncer than the internet makes it sound. Most of what sinks a resume happens in a few predictable places, and every one of them is fixable. Here’s what the data says, including Huntr’s analysis of 1.7 million applications.

1. Slow down on the pre-application questions

Work authorization, years of experience, certifications, salary range. These knockout questions are the real automated filter, and one answer outside the employer’s criteria can disqualify you before anyone opens your resume. Read them twice.

2. Tailor it every single time

In Huntr’s data, tailored resumes landed interviews at 5.8% compared with 3.73% for generic ones. That’s about 1 in 17 versus 1 in 27, and it’s one of the biggest levers you control. AI can speed this up, as long as the final version still sounds like you.

3. Write to the responsibilities section

Requirements are the minimum bar. Responsibilities describe what the job looks like day to day, so that’s the list your bullets should answer.

4. Match the scale of the role

If they want someone managing $50M accounts, “managed client relationships” won’t land. Show you’ve operated at that size, because recruiters are checking whether your experience matches the scale of the job.

5. Use numerals

Dollar signs, percentages, quantities. Write 4 instead of “four.” Numbers catch the eye in a first scan that averages 7.4 seconds.

6. Put your title where their eye lands first

In Ladders’ eye-tracking study, recruiters’ first pass went to job titles, then dates for progression, then education. Your current title, company, and dates need to be immediately visible and immediately relevant.

7. Use their words for the things you both do

Most systems won’t auto-reject you over one missing keyword. Some platforms do rank candidates by relevance before a recruiter sees the list, though, and the person skimming for seven seconds is matching you against the posting in front of her. If they say “stakeholder management” and you wrote “worked with cross-functional partners,” you’re making both of them work harder to see you. Borrow their language, then make the sentence sound like a person wrote it.

8. Give yourself two pages

In Huntr’s review of nearly 244,000 resumes, two-page resumes had the highest interview rate at 3.24%, with one-page resumes at 3.06%. The difference is small, which is the point. Cutting real experience to hit an arbitrary one-page rule doesn’t buy you anything, so stop shrinking your font to fit.

9. Keep the file boring

PDF or Word. Standard headings like Work Experience and Education. Contact information goes in the body, never the header or footer, since Workday’s parser can skip those. Skip the columns too. They won’t get you auto-rejected, but the eye-tracking data found multi-column, cluttered layouts make you harder for a human to scan.

10. Apply early

Once a handful of candidates are in the interview loop, many recruiters stop reviewing new applications. A great resume that arrives three weeks after the posting went live is competing for attention that’s mostly been spent.

Where AI actually helps

Nearly half of hiring managers now treat heavily AI-generated applications as a red flag, according to a 2026 survey of 1,500 of them. Only job-hopping ranked higher. So put AI on research duty. Paste the posting and your resume into ChatGPT or Claude and try this:

“Here’s a job posting and my resume. List the top five responsibilities in the posting, show me which ones my resume doesn’t clearly cover, and flag any vague bullets where I should add a number. Don’t rewrite anything.”

Then fill the gaps in your own words.

I grew up cooking in Lebanon, so the kitchen itself doesn’t scare me. What wears me down is the deciding: what we’re eating, whether I bought the thing, and why the fridge is full and there’s still nothing for dinner.

So I’m running a little experiment: over the past few weeks I cooked through a handful of meal delivery services and wrote up each one, so we could figure out which fits which kind of week. Green Chef is the one I kept coming back to. My son picked the Turkey Couscous, my daughter picked the Diavola Shrimp, and most nights we were eating about 20 minutes after I started.

👉 Read my full Green Chef review.

What’s the dinner you make on repeat? Hit reply and tell me. I’m taking notes for the next round.

Kristel (TA Marketing)

P.S. Use code ASSIST50STAUB for 50% off your first box, 15% off the next eight, and a free Staub mixing bowl set with box three.

“I just took on a new supervisory role and one of the employees I am supervising is someone I consider a ‘work friend.’ On top of new workload, I’m trying to navigate our professional relationship as well.” — Amber M.

Congrats on the promotion! Now the part nobody prepped you for: the first time you tell your friend her deadline slipped, and you watch her face decide whether that came from her manager or from you.

It’s also the part first-time managers struggle with most. In the Center for Creative Leadership’s research on first-time managers, 59.3% named “adjustment to people management and displaying authority” as their hardest challenge, specifically moving from coworker to superior while keeping the good relationships intact.

The instinct is to protect the friendship by going soft. Gentler feedback, looser deadlines, benefit of the doubt you wouldn’t hand anyone else. That’s the move that costs her. Research on workplace favoritism found that the favored employee reports higher emotional exhaustion, more interpersonal conflict, and stronger intentions to quit than her peers. Being the boss’s friend is a tax she pays in the group chat she’s no longer in, whether or not you ever actually tip the scale.

Have the conversation before you need it.

Don’t wait for the awkward moment to show up on its own. Book 20 minutes this week and open with something like:

“I want to name the obvious thing. I’m your manager now, and I don’t want us guessing at the new rules. Here’s what I think changes, here’s what doesn’t, and I want to hear what you’re worried about.”

Then let her talk. Her fear is usually one of two things: that she’s losing you, or that you’ll go cold to prove you’re fair.

Say the boundaries out loud.

Name the specific things that change. You can’t be her venting partner about leadership decisions. She doesn’t get information before the rest of the team gets it. When she wants time off, a project, or a raise, it moves through the same process as everyone else’s. Say all of that once, plainly, so she never has to guess why you went quiet in a meeting.

Use what you already know about her.

Here’s the upside you already have: you know how she takes feedback, what she’s gunning for, which projects light her up, and when “I’m fine” means she’s underwater. Most new managers spend six months collecting that. You started with it. Going cold to look impartial throws that away. Put it to work in her development plan instead.

Keep the warmth even.

Your team is watching the small stuff. Who you sit next to. Who gets the inside joke in standup. Whose Slack messages get the four-second reply. You don’t have to go robotic, and empathy and authority are both load-bearing parts of the job. The warmth just has to be spread evenly, and the friendship gets your own time.

Watch the rest of the room, too. Someone on that team probably wanted this job. You’re focused on the friendship, and they’re focused on whether the promotion changed you. Respect doesn’t transfer with the title. You earn it over the first 90 days, mostly by staying consistent when it’s inconvenient.

On the other side of this? If your friend just got promoted over you, you’re allowed to open the same conversation. Ask her what’s changing. Beats reading tea leaves for six months.

Real friendships survive a title change. They rarely survive going unspoken.

When we polled you, 42% said your company handed you an AI tool with no instructions and nobody to ask. So you figure it out between meetings, one so-so draft at a time.

HubSpot’s free guide to using ChatGPT at work fills in what the rollout skipped:

• 100+ ready-to-use prompts for email, content, customer support, and data analysis
• 21 best practices for sharper answers with less back-and-forth
• 15+ real use cases across industries, so you can see it working in a job like yours
• Fixes for the most common spots where AI output goes sideways

Keep it open next to your next draft and steal the prompt that fits.

👉 Get the free prompt guide.

📧 If your inbox needs a work bestie, Girlboss Daily delivers career intel with a side of pop culture, Monday through Friday.

✈️ That trip you book a dozen times a year? Let Navan Edge remember it and skip the rebooking scramble.

🧴 This lightweight, buildable cream tint melts into skin for a natural, all-day glow without looking heavy or cakey.

📚 The Calamity Club by Kathryn Stockett, from the author of The Help.

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 Work Wisdom of the Week:

“When we are in a leadership climate that cannot sustain excellence, realize excellence always deserves better soil.”

Phyllis R. Calloway, JD, Assistant City Manager

 Share your best work wisdom here.

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