stay? go? help
Hiii,
Happy Friday, friends! And by “happy,” I mean we’re all doing our best with the emotional resources we have left.
I’ve been thinking about what holiday movies to watch while we speedrun the rest of 2025, so if you have any strong recs…I want em!
This week’s Q&A features: When is it time to leave a job you like but leadership you…don’t?
And why do some companies treat employment classification like a Choose Your Own Adventure book written by someone who’s never met the IRS?
We’re talking about staying vs. going when you’re under-supported, and whether employers can magically turn someone into a 1099 after they resign (spoiler: absolutely not).
Grab your caffeine, your boundaries, and your common sense. You’ll be needing all three.
And if you haven’t filled out this industry events survey yet, can you do me a solid and take 30 seconds to complete it pretty please?
Help me figure out where I should do meetups next year!
Oh, and also send me all the unhinged questions you have for a chance to be featured! 😇
ASK AWAY
🤔 contracts & careersCopy anchor linkCopied
✍🏾 Given the crazy HR job market right now, when do you know when its time to move on from your job or suck it up and stay?
Context: Small company <100 employees - I am the HR Manager, and have a VP of People who doesnt have an HR background and doesnt provide much support. The pay is good, I like the work, and like the people. But I dont have a strong connection to my boss or my direct report. I feel unsupported and dont see much room for me to grow here. Should I stay or should I go?
📣 Frank Richardson II, Director of HR @ SELF Incorporated:
HR Manager: From my perspective, you’ve checked all the major boxes... you’re satisfied with the salary, enjoy the work, and like the people. In a market like this, I’d suggest staying unless or until your manager begins to question your expertise or decision-making. In your next 1 on 1, I would suggest delicately sharing some of the challenges you may be facing.
📣 Amanda Jesenof, Director, HRBP @ iA:
In this market, I wouldn't leave without something lined up unless there was some truly toxic and unethical stuff going on. A well-paying job with good people is hard to come by - there's a good chance that fixing the relationship with your manager will be easier than landing a new gig. I agree with Frank that you should take advantage of your next 1:1 to discuss how you're feeling. Try to start building a personal connection and talk about how your HR background and their non-HR background could really complement each other to push the department forward. In an organization that small, you may not have a lot of room for growth long-term, but take advantage of the opportunity to learn as much as you can from a VP with a different background before you look outside.
📣 Jessica Hudson, Leadership Development Program Manager @ BAE Systems Inc:
You've got some great advice here. Talk to your manager, give them an opportunity to make it better then go do the same with your direct report. You are responsible for that relationship, go figure it out. :)
One great thing about a small company is the ability to wear multiple hats and expand your role well beyond what a normal HR role might look like otherwise. Any passion projects you've been thinking about? Any skillsets you want to build out but haven't been able to? Explore those opportunities and see if there's support for it.
If you still aren't any happier start putting some feelers out in the market. Agree with everyone else, I wouldn't quit without a job unless you have a nest egg you are comfortable giving up. It's tough out there and whow knows what 2026 will hold.
Safe Space members can join this discussion here. Not a member yet? Apply to join here.
✍🏾 Can a company change the "classification" of someone after they leave the company? For example an EMPLOYEE salesperson working on commission gives their notice and are switched to a 1099 contract person (to save the company taxes) while their owed commissions are paid out.
Context: Family owned, approx 12 employees
📣 Sharon Snell, Chief HR Officer @ State of the Heart Recovery:
A company cannot reclassify an employee as a 1099 contractor after they leave simply to reduce tax liability. Classification is governed by federal law, primarily the IRS common law rules that define whether someone is an employee or an independent contractor. Those rules are based on the nature of the working relationship, not the employer’s preference or convenience.
If the individual was an employee while performing the work that earned the commission, they must continue to be treated as an employee for the purpose of paying out that commission. Reclassifying them after the fact creates several risks. These include misclassification findings, back taxes, penalties, and potential wage violations if the commission is considered earned wages in that jurisdiction. The company does not have the discretion to retroactively redefine the employment relationship because the underlying facts have not changed.
A helpful way to frame this for leadership is to anchor the conversation in compliance rather than preference. You can say something such as:
“Classification is determined by how the work was performed, not by how we choose to pay someone after separation. Since the commission was earned as an employee, we must process it under employee status. Changing the classification now would be considered misclassification and exposes the company to federal penalties, tax issues, and wage claims. The safest and legally compliant path is to keep them classified as an employee until all earned compensation is paid.”
If the individual will perform new, future work that meets the IRS contractor criteria, they could enter into a legitimate 1099 relationship. However, that applies only to new work, not previously earned compensation.
Family owned or not, the same federal standards apply. I would strongly encourage aligning with IRS and DOL guidelines to avoid unnecessary risk.
📣 Jennifer Pokorny, Head of Operations/HR/Finance @ Rock Paper Simple:
No, not even sure of the legality of that (sounds like towing the line of tax fraud). The owed commissions (I believe) should be paid the same rate/way when they were earned, not when they are paid out, even if being paid out way later.
📣 Eduardo Caquias, HR Business Partner @ Boston Veterinary Clinic:
You cannot change an employee's classification after they are terminated. A worker's classification is clearly outlined by the IRS and you can find all the details here: www.irs.gov/newsroom/worker-classification-101-employee-or-independent-contractor.
The only time you can change the classification is if the employment relationships changes from employee to that of independent contractor by meeting the IRS criteria for an independent contractor.
Safe Space members can join this discussion here. Not a member yet? Apply to join here.
🚨 ON YOUR RADAR
🎧 Belonging sounds cute until someone shows up as their whole self and suddenly HR is getting emails about “professionalism.” In this episode, Erica Lydell and I dig into masking, identity, neurodiversity, and how belonging at work should feel. Check it out on Spotify or Apple Podcasts!
🔮 Annual reviews are finally dead, and I’ve never been happier. This month’s HR Therapy is all about what rises from the ashes: real performance enablement, actual feedback cultures, and AI that supports humans instead of replacing them. If you’re ready to stop dragging a relic from 1997 into 2025, come join us!
🔍 Can AI be used ethically in hiring? eSkill breaks down what’s smart, what’s shady, and what might actually be illegal. A quick, clear guide to using AI without bias, blowback, or accidentally letting a bot make the final call!*
❤️ From ‘I Hate it Here’ to ‘I Love it Here’: Your Culture Transformation Roadmap. HR can influence culture change in any organization, and this course teaches you how. Join the Safe Space community to access it!
*This one is brought to you by one of my amazing brand partners
📝 RESOURCE OF THE WEEK
Each week I feature a resource I love from the Safe Space library that I believe would be relatable to this week's newsletter topic.
This week, I’m sharing an HR Annual Planning Template. Check it out HERE ⬇️
FRIDAY FUN
😂 ahh yess the December PTO requests Copy anchor linkCopied
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If there is one thing I ALWAYS knew it was my PTO policy.
Here's a reminder: TAKE THAT PTO! LIVE YOUR LIFE!!!!
That's all for this week!
Reminder: Do something fun this weekend just for yourself.
