older teams, younger bosses
Hi ya party people,
After months of planning, the Safe Space Summit FINALLY happened yesterday, and I have soooo many thoughts!
But before I word-vomit all my feelings and gratitude onto the internet, I need at least one full night of sleep, two or three coffees, and maybe a week-long nap. 😴
So for now, let’s shift gears to our regularly scheduled Q&A time, and you can look forward to my debrief soon, k?
This week, we’re talking about two questions that may hit close to home for a lot of HR and HR-adjacent folks:
One person wants to know if it’s worth diving into HR education after years of working in culture and engagement.
Another’s managing a team older than her in a toxic environment, and HR’s not exactly showing up to help.
Let’s see how the solutions stack up!
Oh, and don’t forget to send me all the unhinged questions you have for a chance to be featured! 😇
ASK AWAY
😒 attitudes & careersCopy anchor linkCopied
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✍🏾 I have been working in a management position in the culture & engagement/DEIB/well-being/org change space for the past 6 years or so. However, I don't have an HR background nor is my role situated in HR. I've been wondering whether it would be beneficial to invest some time/resources/energy into acquiring formal HR experience and/or education. It seems like a tough time to be in HR (and most occupations and industries, for that matter), so I'd be really grateful for your advice. Probably not a simple answer here, but any thoughts you have would be helpful. Thanks very much!
Context: 30k+ employees in higher ed & health care org
📣 Erin Thomas, VP, Culture, Inclusion & Engagement @ Upwork:
I love that you're exploring growth opportunities. To better answer your question, I'm curious if you're set on a next step for your career?
Are you aiming to break into a new industry or type of organization? Are you looking to advance within higher ed/health care? Don't know yet?
📣 Karen Wood, Human Resource Department Manager @ United Consulting:
Yes, I love that you are open to growth in the HR world! I agree with Erin, answer those questions on where you want to go/do.
I actually came from production in a transportation company; within my role, I became interested in culture/engagement/well-being/org change and moved to another company in an HR role doing those tasks as well as learning all things HR (Benefits, Legal compliance, Employee Relations, performance reviews, etc.)
I am currently enrolled in an online eCornell University course on Employment Law certificate (that my company is paying for!) to close the knowledge gaps. They are a great resource to check out for online programs and degrees.
HR in smaller to medium-size companies is different than large companies, where HR does it all as opposed to having multiple departments for these areas. I am curious in your large organization of 30k+employees, if you can shadow the HR personnel and get a feel for what they do?
If you are looking to leave your role/company and move toward the HR world, then I would invest some energy into what you want to learn more of. Good luck!
📣 Caroline Balter, Senior HR Manager @ Third and Grove:
A larger breadth of on the job training and a certification might help if you want to go into a broader leadership role or HR Manager type of role. At a lot of workplaces, there is an HR team of one or two and so it might call for more knowledge in other HR areas like performance management, compliance, talent acquisition, compensation and benefits.
If you like the work you're already doing, I'm not sure it would help you make strides in the space you're already in, since you've been at this for 6 years and that's quite a bit of on the job experience in those areas you noted. I would find some sort of exercise to help you work out what you do/don't like about your job currently in order to direct where to go next, or what type of training/ exposure might help.
I think there is one on Hack Your HR. Or you could talk with your manager about it. Generally I'm a fan of any training or certifications you can get your employer to do/ pay for that sound interesting or inspiring to people.
Safe Space members can join this discussion here. Not a member yet? Apply to join here.
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✍🏾 I manage a communications team of three as a 34-year-old woman in a very toxic organization. Most of the people I manage are older than me. I deal with a lot of insubordination and while I've gotten HR involved, they do little to help with the issue long term. Is there anything I can do or could be doing wrong that is inviting this issue?
Context: I work in higher education, staff of about 20-30.
📣 Jordan Giddens, Head of People in Operations @ Rice & Kendig:
As the HR department of one in my mid-20's, I feel you. One thing that helped me was getting really clear on the facts. What do you know for sure that shows toxic behavior? Are people missing deadlines, pushing back on direction, turning in sloppy work, speaking negatively about you in meeting?
Document those specific instances—not to tattle, but to stay grounded in behavior, not emotion. Then you can calmly say, “Here’s what I observed, here’s the impact, and here’s what needs to happen next.” Beyond that, it’s worth asking: Am I checking in with people personally? Am I championing their ideas and pulling on their expertise? Am I setting clear expectations—even when it’s uncomfortable? Am I clearly communicating the direction the team needs to go and what our goals are?
Also, what do your own leaders think? If they’re not willing to support you, that tells you something too. What helped me was making time to ask about people’s lives, following up on things they’d shared, addressing their concerns, and treating them with the respect that experience deserves.
Many of them have valuable skills and wisdom—pulling them in for input not only helps the team, it builds connection and trust. Also, just asking what you could do to be a better leader or better support them, can really build trust. I know how frustrating this can be and I wish you the best in this situation!
📣 Lia Seth, Director of People @ Cylinder Health:
It's hard to know how to give advice when it's not clear the level of insubordination you're dealing with. Are your direct reports not respecting you as their manager because of your age, or are you expecting a level of deference that's not necessarily reasonable at any level? Are their actions inexcusable regardless of context, or does everything in this organization not align with your preferred working style/culture?
Regardless, it's not uncommon for a manager to be younger than their team! Is it possible you're feeling more awkward about the age difference, and trying to overcompensate by making a point of your authority on the team? Your team will take their cues from you – imagine if your own manager was younger than you. Would you prefer they were hesitant about their authority, overbearing and demanding, or if they treated ages like they didn't matter in the context of your working relationship? Try to adopt the attitude of the manager you'd like to have.
If that doesn't resonate, and you think your team is truly resisting your role due only to your age, that should be addressed the same way you would address an employee who wasn't meeting deadlines, responding to client emails, or showing any other performance issue. Start by approaching with curiosity: “I’ve noticed you seem reluctant to start on the projects I assign you. What’s going on?” Or, “I appreciate you sharing your thoughts on this, but ultimately I’d like you work on this comm the way we discussed in last week's team meeting. Can you do that?" Remember you were hired for this job because your company thought you'd be good at it!
On the other hand, if the whole environment is truly toxic, you may not be able to single-handedly change the culture into one of collaboration and mutual respect. In that case, I'd focus on documenting each instance of "insubordination" and presenting the case to HR as a long-term trend, rather than individual issues. This is more likely to get you the support you're looking for. Good luck!!
📣 Alex White, Regional Director, HR @ Washington Duke Inn & Golf Club:
Lia nailed it - especially the point about first clarifying what “insubordination” actually looks like. That distinction matters a lot. There’s a big difference between healthy pushback (which can signal engagement) and truly disrespectful or undermining behavior that erodes trust and authority.
I’d also add: this is where leadership presence really comes into play. When managing individuals older than you — particularly in a culture that’s already toxic — confidence, clarity, and consistency become your greatest tools. Your team will mirror whatever energy you bring to the room. If you’re tense, they’ll feel it. If you’re steady, they’ll steady themselves around you.
A few thoughts to build on Lia’s excellent advice:
- Lead with clarity and calm.
Make your expectations explicit and behavioral — not emotional. “I need everyone to meet deadlines and respond to feedback respectfully” lands better than “I need more respect.” Specificity removes interpretation. - Check the system, not just the symptoms.
If HR isn’t helping and the culture tolerates poor behavior, you’re managing inside a system problem. Don’t carry that burden alone. Document patterns (dates, times, impact), and use that record to frame your case around organizational risk, not personal frustration. - Confidence without apology.
When you lead older team members, confidence doesn’t mean overcompensating — it means showing quiet authority. Own your role. Make decisions, communicate them clearly, and don’t apologize for doing your job. You earned that seat. - Protect your energy and perspective.
Toxic environments can make you question yourself — don’t let them rewrite your narrative. If you’re trying to lead well in an unhealthy system, that’s not a reflection of your ability; it’s a reflection of the culture around you.
You’re not alone in this. Many strong leaders have stood exactly where you are — balancing credibility, composure, and chaos — and come out sharper for it. Keep leading from integrity, document what matters, and remember: you can set boundaries and hold compassion at the same time. Wishing you the best of luck!
Safe Space members can join this discussion here. Not a member yet? Apply to join here.
🚨 ON YOUR RADAR
🎧 I Hate It Here Podcast: I'm always dropping new episodes with your favorite People Ops leaders! Until we return with a new season of guests, enjoy some of the greatest hits! Check it out on Spotify or Apple Podcasts!
❤️ 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!
🤓 What if leave management didn’t feel like chaos? Tilt built a platform that finally makes leave clear, compliant, and actually human! No more outdated vendors or spreadsheet nightmares. AI handles the admin so HR can focus on PEOPLE, not paperwork!
📝 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.
Culture is not declared. It’s demonstrated, and Sergio Peña is making the case for why HR is not responsible for company culture. Check it out HERE ⬇️
FRIDAY FUN
😂 I guess I need to do that???Copy anchor linkCopied
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So, what do I want to accomplish????
I should probably have decided that before the quarter started?
What IS the ideal time to write the quarter's goals??
That's all for this week! I hope you enjoyed! If you have any thoughts, please let me know. I'm allll ears.
Reminder: Today is FRIDAY. 🙏
