My wife and I didn’t have grand plans—no weekend getaway or fancy dinner, no activities reserved months in advance.

We walked around the lake where we first met and later got married. Had breakfast at a local cafe. Went to a coffee shop and wrote. Enjoyed a sunny, 79-degree Seattle day and each other’s company without any pressure to go anywhere or do any specific thing.

It felt luxurious to walk around without a care in the world at 9 a.m. on a Monday morning, while the rest of the world worked.

Monday, Monday

I can’t remember the last time I took my birthday or other personally important day off. Maybe never?

Even if I had, there’s little chance it would have been on a Monday.

Mondays set the tone for the week ahead. Miss a Monday when everyone else works and you start your week ridiculously behind.

In my current role, we hold our go-to-market team meeting on Mondays. Our weekly all-company stand-up covers plans for the week and on the first Monday (which this was), plans for the month. This particular Monday also included a rescheduled call with one of our board members.

I considered taking Friday off instead. But I didn’t.

A long time coming

It’s taken a long time to get to this place.

I haven’t been one to take my birthday off. And it would be completely unheard of for me to use my precious vacation time to just do nothing.

Heck, I haven’t even been good at truly stepping away from work—not checking email or finishing that last “to do”—when I’m on PTO.

But I’m older now. And wiser. 🙄

Or maybe I’m just tired of it all. Grind culture. Corporate greed that prioritizes profits over people. The “work now, enjoy life when you retire” bullshit we’ve been fed our whole lives.

Who benefits from this? Not you. Not me.

Leadership matters

Over the years I’ve talked to countless colleagues trying to navigate personal situations alongside work. My counsel has always been the same:

1. Your employer does not care about you. Now granted, your boss may, but the company as an entity does not.

2. You should always do what’s best for you, because your company will only do what’s best for them. Don’t believe me? Look at how companies are clawing back employee benefits (gated article) right now.

I know all of this. I believe all of this. And yet I’ve still struggled to prioritize myself.

This is where leadership matters most. As leaders, we can set the example for our team. Normalize life being more important than work. Remove barriers to taking time off. Encourage and celebrate team members living their lives.

That’s what my boss did for me.

He didn’t act inconvenienced that I wasn’t going to be there. He didn’t ask me to complete and share my monthly plan before Monday—in fact, he suggested we just push it to later in the week.

There were no passive-aggressive comments. No insinuations. No guilt.

You’re going to be off? NBD, his response said.

And so I took Monday off and enjoyed a beautiful Seattle day with my equally beautiful wife.

Like it was the most normal thing to do in the world. Because even though it doesn’t always feel that way, it really should be.

PS: Happy anniversary, my love. Here’s to many more to come. ❤️

If you enjoyed this post, please support my work by subscribing to Some Guy Named Rae. Weekly posts like this one will be delivered straight to your inbox every Sunday.

Subscribe now

(I know what you’re thinking—I must be really fun at parties. 🙄)

There’s general agreement that AI will change the nature of work. Accountants and lawyers, marketers and salespeople, product managers and software developers, school administrators and professors … these roles and so many more will change.

But how? Who the eff knows. There are a lot of theories—and a lot of LinkedIn posts—but no matter how confidently they tell you, no one knows for sure.

Slap some AI on that

We’re in the very early days of a new technology and like so many new technologies before it, we’re mostly just slapping AI on top of existing processes and models.

Remember the early days of the Internet? Company websites were primarily marketing brochures, sans that freshly printed smell. IYKYK.

As a CIO I saw this all the time. We added computers to classrooms but the process remained the same. PowerPoint slides replaced overhead transparencies but nothing else really changed—except the cost to equip and maintain classrooms went up exponentially.

Or my own personal favorite (and by favorite I mean nightmare): we brought in new enterprise systems with amazing capabilities and then spent millions of dollars and years of time making the shiny new system behave exactly like the old one, which had processes designed solely based on system limitations—not actual need. 🤦🏼‍♀️

It’s not new. It’s not unexpected. And it’s totally okay that this is the stage we’re in. We just have to stop pretending that we’re not.

The challenge is moving beyond this stage.

The skills we actually need

Humans are remarkably resistant to change. Organizations even more so. Knowing this, how do we:

• Build more adaptable and resilient companies?

• Create cultures oriented around continuous learning and improvement?

• Enable students and employees to be builders and innovators—creators, not consumers?

This is the upskilling we actually need.

We can’t train someone for an AI-enabled role right now. There are no real models for how those roles will work—and the technology is changing so quickly that anything we teach today could be obsolete within a month.

We need to help our teams imagine a whole new way of working.

Not the current processes and deliverables augmented with AI (this is mainly what I wrote about in Leveling Up With AI). Not a “thinking outside the box” type of exercise. We need to start from a blank slate—asking ourselves, “if this job didn’t exist, how would we design it today?”

That’s extremely hard to do. If it is even possible, it requires at least two things:

• The ability to step outside the role and work backwards from the outcomes it’s meant to drive

• Consistent time and space to experiment with new technologies—and figure out how they help achieve those outcomes

This isn’t a one-time activity. It requires continual reinvention of our work. Who’s got time for that?

I don’t know about you, but I rarely have time to get everything done on my ever-growing list of things to do, much less play with AI to reimagine my role from the ground up. And I work for an AI company.

Our challenge as leaders

As I was writing this blog, I came across a friend’s LinkedIn post talking about an AI conference they’re planning to attend. The conference agenda included this note:

Exactly. As leaders, we must rise to this challenge.

If we want to lead in the age of AI, we need to tackle the very nature of work itself. Our company cultures. How we structure time and measure productivity. The value we place on experimentation and change.

We need to set the expectation that our team members’ roles and work will continually evolve, and we need to provide the tools and space to enable it.

The problem isn’t AI. It never was. It’s getting ourselves—and our teams—comfortable with constant change.

Bonus: I’ve been talking about “thinking outside the box” for a long time, it seems. Here’s a 2013 video where I talk about throwing the box away:

If you enjoyed this post, please support my work by subscribing to Some Guy Named Rae or sharing it with a friend. Thanks!

Subscribe now

Share

At some point or another, we’ve all had that person on our team, too. They’re capital-T toxic. They may be actively undermining their colleagues. Gaslighting them—and you.

It can take a while to see it—they’re often good at making you think it’s you, not them—but once you do, you can’t unsee it.

It’s pure poison that will destroy your team if you don’t address it quickly.

One bad apple, indeed.

More insidious apples

There are other types of bad apples—ones less obvious, and in some ways more insidious—because they mean well.

Mediocrity (your underperformers) and martyrs.

They’re not bad people, which makes it all the more difficult to see how they’re silently eating away at your team, rotting it from the inside out.

Mediocrity slowly drains the life out of everything.

Your best people notice what you tolerate. Before long they disengage. Or simply leave.

They don’t want to carry the weight of someone who isn’t pulling theirs. They want teammates who will push them to be better—ones who can help them succeed.

Weaponizing the mission

And then there’s the martyr. Like mediocrity, they don’t look like a problem at first. They’re passionate. Principled. Convicted.

They position themselves as the arbiter of what’s “right” for the company. Everything is framed as protecting the mission. Over time, that becomes a weapon used to shut down ideas, challenge decisions, and undermine others.

The martyr doesn’t build alignment. They quietly create division instead. If you’re not meeting their personal litmus test, you’re not just wrong—you’re a problem.

Mediocrity lowers the bar. The martyr sets a bar only they can meet.

None of these people—not even the toxic ones—wake up with the intent to hurt your team. But intentions don’t matter. Actions do.

All of them will break your culture and your team—if you let them.

Bonus read: Niceness can be an equally insidious culture killer.

No forewarning. No purposeful break. No push to get something out regardless of what else was going on. Just … nothing.

The week prior, I woke up mid-week and found myself so fatigued that I got winded trying to get out of bed—so back to bed I went.

I cancelled most of my meetings but had too many things to do to just rest. So I grabbed my laptop and headed to the couch to quietly work away between short cat naps. Not my most productive time, but stuff got done. 🤷‍♀️

I was sick, but you know how it is—work waits for no woman. (I’ve written about this before, in Out Sick.)

And so it goes …

That’s been the story of my career. Work over pretty much everything else. I’ve always been career-oriented and ambitious. I love my work—and I derive much of my identity from it.

But the reason runs deeper than that.

I have a deeply ingrained and not altogether healthy sense of responsibility. I’ve always believed that you must do all the things you have to do before any of the things you want to do.

Now here’s the key: my “have to’s” have historically related to work, external commitments, and anything expected of me by others. Buh-bye, self-care.

In fairness, I have gotten a little better at this in recent years. But this blog is a commitment I’ve made—to myself and to you—and I take it seriously.

So why didn’t I write?

Alongside my own illness, my dog was having trouble keeping food down. On Thursday, I took him to the vet. They did blood work and gave him some medicine.

On Friday, they diagnosed him with pancreatitis. Special food, more meds. Back to the vet on Saturday morning—things were getting worse.

Saturday evening, we said goodbye to my sweet, nearly 17-year-old pup for the last time. And then I woke up early Sunday morning and flew to a conference for work.

I was a wreck.

I couldn’t write. I couldn’t bring myself to go to the two receptions that I was supposed to attend on Sunday night. All I could do was cry.

My weekend was consumed with grief. And that’s okay. More than okay, actually.

But … work?

I’ve heard for years “No one on their deathbed ever said, ‘I wish I had spent more time at work’.” I’ve even said it to others myself.

But I’ve still lost a lot of really important moments to work.

There’s so much more to life than work. There are birthdays and weddings, spring breaks and holiday concerts. Opening day at the stadium, summer concerts in the park … alongside sleepless nights, high fevers, and mental health days.

These are the real “have to’s.” Prioritize them. Prioritize your children, your significant other, and yourself. Especially yourself.

Work shouldn’t get in the way of life—not the joys, and not the sorrows.

So rest in peace, Obi (Wan Kenobi). You were my constant companion for 16 years—even at work. I will miss you.

Bonus read: I know what you’re saying—now just isn’t a good time to [insert your need here]. Spoiler alert: It’s never a good time. Do it anyway.

I’ve been hearing this a lot lately—especially from mid- to late-career folks leaving (often high-level) roles because they want to do meaningful work with people they like.

We’ve all worked with asshole colleagues or toxic managers—or both. We’ve had enough of the corporate slog, profits over people, and grind cultures. Hard pass.

After working in these types of environments, the inclination is to over-rotate toward niceness, where everyone gets along and pleasantness prevails.

But nice can be every bit as ruinous to your culture. Maybe even more so.

I know nice …

I’ve worked in “nice” cultures. Higher ed is filled with them. And put a higher ed institution in the Midwest or the South and you’ve got a niceness double whammy.

But organizational niceness isn’t all it’s cracked up to be. It prioritizes pleasantness over performance. It masks role misalignment or even incompetence.

It enables toxic behavior to persist under the guise of upholding an organization’s mission, values, or “family.” (Read more in my post Work Isn’t Family)

It’s actually not all that nice, underneath it all.

Let’s not be “nice”

I’m one of those people who left my corporate job because I want to do meaningful work with people I like. But I don’t want to be nice.

Which is good, because of all the things I’ve been called over the years, nice is not one of them. Direct? For sure. Empathetic? Sometimes. Nice? Nope.

Nice means: “pleasant; agreeable; satisfactory.”

Satisfactory?? Satisfactory is “acceptable, though not outstanding.” Inspiring, right? I’m not aiming for satisfactory—and I don’t want to work with people who are.

I want to work with people who are genuinely good-hearted and incredibly talented, high-performing, and driven to succeed.

I want to work with people who are smarter than me and who make me better simply by working with them—they raise the bar and make me want to up my game, too.

And definitely don’t settle

Working with people you like is not an either/or situation. Genius and goodness are not mutually exclusive.

We do not have to choose between working with a brilliant asshole or a kind but less than competent colleague. If I’m being honest, I’ve worked with both—and prefer neither.

But this is more than just a personal preference. As leaders, we cannot let our organizations settle for niceness.

We may tell ourselves we’re creating a kind, nurturing, and collegial workplace culture, but what we’re actually doing is avoiding hard conversations. Hard decisions.

We’re letting people persist in roles that are neither good for them nor good for our organizations. That isn’t kindness—or leadership.

We’re also sending a very clear message to our high performers. They may enjoy it for a while, but they won’t stay long. No top performer wants to be on the B team.

Hold a high bar

If we want to do what’s right by our people and our organizations, we have to set and hold a high bar for people and performance.

Being pleasant … or agreeable … or satisfactory does not meet that bar. Neither does high performance in and of itself.

Building a team filled with “people you like” might look like hiring people who are:

• Passionate and smart, but humble.

• Unselfish and collaborative, but who refuse to settle.

• Excellent at what they do but are still striving to be better, and will be brutally honest to help others be better, too.

People who want to make an outsized contribution to achieving a team’s mission—and have the capacity to do so.

We’ve all seen the chaos one bad employee can create.

Are we paying enough attention to the damage a “culture of nice” is doing to our organizations?

Bonus read: Sometimes the kindest thing we can do for an employee is help them thrive elsewhere.

“Yep,” was my only response.

If you’ve known me for more than a few seconds, you know that I proudly identify as a troublemaker—and have for pretty much my entire professional career.

OG troublemaker

Waaaaay back in 2009 (now I’m dating myself) I was part of a selective leadership institute for emerging IT and library leaders.

When we registered, we had the opportunity to select ribbons to attach to our name badges—common today, but quite new at the time.

My fellow institute members and I rifled through the ribbon options, contemplating how we wanted to identify ourselves for the two-week experience. The second I saw the TROUBLEMAKER ribbon, my choice was clear.

I haven’t thought about that experience in quite a while, nor have I given much thought to my leadership philosophy recently.

A badge of honor

And then I started listening to Make Trouble by Cecile Richards—because how could I not with a title like that?

She describes herself as a lifelong troublemaker, a a badge of honor that means:

Sometimes it’s “pretty damn awesome,” she says, and “other times it’s scary.” It’s probably a little of both most of the time.

It’s also something we don’t do enough of, because making trouble comes with risk. Political capital. Strained relationships. It could even cost you your job—or your life.

And yet, perhaps now more than ever, we have to make trouble anyway.

As I’m writing this—sitting with my wife on a Saturday morning in our favorite neighborhood coffee shop—people are organizing down the street for No Kings Day.

They, and millions of other like-minded citizens across the U.S., are making a little trouble today. Maybe you are too. Good for them (and you).

Good trouble

Making trouble isn’t only for politics. As leaders, we can and should all be troublemakers, “raising hell” when the situation calls for it.

Like when Costco refused to drop its DEI initiatives. Or when Anthropic stood up to the Pentagon. It wasn’t just the right thing to do; it was good for business. Go figure.

Your form of troublemaking may not be as public as these examples. But it doesn’t make it any less important. It might look like:

• Standing up for equitable treatment of your team members.

• Refusing to do business with companies that don’t have the same values as you.

• Ensuring products are deployed ethically and responsibly.

Because that’s what leadership requires—holding ourselves and our organizations accountable to doing what’s right for our employees, our businesses, and our communities.

So—what kind of trouble are you going to make this week?

Bonus reads: Sometimes there is only one right answer—and we have a responsibility to say so.

The quote came from Cecile Richards’ memoir, Make Trouble, which I’m currently listening to. She attributes the saying to her mother, the trailblazing Texas governor Ann Richards.

It struck me because it’s such a foundational concept, but one that we often forget.

Whether you’re leading an initiative, managing a team, or selling a service—people will act (or not) for their own reasons. Not yours.

It’s not enough to tell them all the benefits your vision, initiative, or solution provides. (And don’t get me started on a features dump. Just—don’t.) Understanding and articulating the benefit to people is necessary, but not sufficient.

You have to understand what motivates them. What compels them to act when they ask themselves, “What’s in it for me?”

As leaders, it’s especially important for us to remember this.

You are not leading if no one is following. And people will not follow just because you tell them to—or because your title demands it. They will not follow unless they have good reason to.

A reason that’s just right for them.

Those reasons will vary, but they often boil down to two things: intrinsic motivators and external incentives. How people view themselves and how they want others to perceive them.

Your job is to discover each person’s reason, understand it, and align to it.

Until then, no one’s buying what you’re selling—whether that’s a product or a vision.

Bonus read: We’re in the throes of March Madness and just weeks away from the WNBA draft—making it a great time to revisit leadership lessons from Golden State Valkyries coach Natalie Nakase.

Cover photo by Rommel Davila on Unsplash

This is not a new concept in the world, but it was new to me. The idea is that there are three stages in your career: a time to learn, a time to earn, and a time to return—to give back.

In your 20s, you have a lot of learning to do. You explore different majors in college and different roles as you set out in your career. You’re trying to find your fit, grow your experience, and build your career.

Your 30s to mid-50s are peak earning years. By now you’ve started to settle into your career and have responsibilities. You’re saving up for a house or paying a mortgage, providing for a growing family, and saving for the future—a time when you choose not to or won’t be able to work.

Then something shifts

Somewhere in your late 50s or early 60s, you enter a new phase in your career, one where giving back feels more important than ever.

It’s not that you quit earning—or even learning.

But your priorities change. You no longer wish to grind it out day in and day out doing unfulfilling work with people you can’t stand.

You become less interested in taking on career-changing projects or next-level leadership roles. You’re less concerned about being in the spotlight. You begin to think that helping others achieve those things is way more interesting.

The joy of giving back

And that’s the state I find myself in more and more these days. While I’m arguably still in my late Earn years, I find it sparks real joy to spend time talking with early- and mid-career folks—as I did this past week.

A couple of days ago I got to chat with three incredibly smart and talented college students who are just beginning to think about their careers.

They asked thoughtful questions about imposter syndrome, balancing empathy and tough decisions (read Don’t Be An A*Hole), and how to maintain authority as a leader when you make mistakes.

“It’s not your job to be right all the time,” I told them. But that’s a topic for another post. 😉

Don’t apologize

A week before that conversation, I found myself talking to a mid-career professional who was struggling. They enjoy the people they work with and the opportunities their role affords them—but they don’t make enough money to buy a home.

While there are almost always trade-offs in your career—high tech salaries may come with more pressure and less stability than roles in other industries, for example—it’s okay to prioritize income in your 30s and 40s.

There’s no need to apologize for it or feel bad about it. It’s expected. Desirable, even.

That’s the stage of career that you’re in.

So go forth …

… and Learn, if that’s where you’re at in your career. Take every opportunity to learn new skills and try new things. Travel. Job hop. Company hop. This is your chance to find what works for you—and what doesn’t.

When you’ve reached your peak Earn years, go all-in. Prioritize yourself. Build wealth now and for the future. To be clear, this doesn’t always mean picking the largest paycheck.

I know plenty of folks who maximized their retirement options by committing to a career of public service in government, education, or the military, and retired at a (relatively) young age with a liveable pension.

And as you near the end of your working years, give yourself permission to want something different.

You may find yourself wanting to step backward on the career ladder—moving from manager to individual contributor or from employee to contractor. You may decide you actually enjoy having more flexible time and are willing to earn less to have a better quality of life.

You may find you actually enjoy taking vacations. Who knows?

In these years, don’t forget to give back—to Return the mentorship and opportunities you were given and help a new generation of leaders take the helm.

Bonus read: Your career path will be messier than you’ve been told, and that’s okay.

You got the interim role—congratulations!

(Of course you did, because you’re a badass.)

But suddenly you have an “oh sh*t” moment. Now what? The rubber is about to meet the road in a big way.

It’s one thing to think about the role and another to have to execute in it. Are you even up for the task?

(Of course you are, because you’re a badass. Also, kick that imposter syndrome to the curb—let’s go!)

Now you have a whole new set of questions. You’re no longer questioning whether to take the role, but rather, how to operate in it:

• Am I there to babysit or to lead?

• Should I make changes—or keep the status quo?

• What should I be aware of or consider as I step into the role?

Own the role

The biggest mistake people make in an interim role is taking the “interim” part too seriously.

Put interim in your email signature—if you must—and then forget about it.

You are the Director or CIO or CEO or whatever other role you’re filling. You might be in the position for a week, a month, or a year (heaven help you if you’re an interim for more than a year) but you are the role—until you’re not.

So own it. Do the job to the best of your ability. Make the best decisions possible for the long-term benefit of the organization (read Stop Overthinking Decisions and Make the #&% Decision, Already).

As one friend and newly-appointed interim recently shared:

To change or not to change

Given the charge to “own the role,” you might think that you have a mandate for change.

Not necessarily.

Ownership requires understanding and alignment with the direction set by your board, president, or upstream leadership—and making the right decisions for the organization, now and for the long term.

Sometimes that means maintaining the status quo. Other times it means making modest, incremental changes. Or less modest changes (read The Secret to Change).

And occasionally, you may have a mandate to make massive, disruptive changes at the expense of the permanent position—creating a clean slate for whomever comes next (best to know this up-front since your post-interim options will be limited).

There is no one charter for interims. You’ll have to determine the right course of action for you, your role, and your organization at that moment.

What you don’t know

Even though you were a part of your organization prior to the interim role, there are likely things that you don’t know—potentially a lot of things you don’t know.

You don’t know what you don’t know. Nor will people always tell you.

Approach the role as if you were brand new. Set aside what you think you know. Ask questions. Lots and lots of questions.

Seek out contrarian perspectives. Gather input from team members, stakeholders, customers (if you have them). Listen closely and without defensiveness.

Look for what’s not working, and pay careful attention to what’s not being said.

When you look at your organization with fresh eyes, you might just be surprised by what you learn.

And one more thing …

In no particular order, here are a few additional things to consider when you step into your new role:

• Sometimes your alignment with the previous leader is a benefit; other times a liability you’ll need to distance yourself from. Figure out which one is the case in your situation and act accordingly.

• You will now be managing your former peers. The peers you were friends with, went to lunch with, and genuinely liked—and the peers you didn’t. You cannot pick favorites or be perceived to have them. You will need to set appropriate boundaries with the former and treat the latter with the same level of respect as your friends.

• Being at a new level can be lonely. Folks you used to confide in now report to you and confiding in them may be unwelcome, inappropriate, or potentially prohibited, depending on the sensitivity of the information. Find your circle of friends and advisors you can turn to for gut checks and guidance.

Stay tuned for part 3 of The Interim Question: what happens if you don’t get the permanent role?

Bonus read: Not everyone wants to be a leader—and not everyone should be one.

“What are the hard parts?” they asked.

“It’s all hard,” I replied. “But that’s why I like it.”

I’ve often said that I have a personality defect—I run toward difficult situations, not away from them. But who are we kidding? It’s 100% true.

I love a good challenge. The harder, the better.

And tell me something can’t be done? Oh no you didn’t. Hold my stainless steel, refillable water bottle.

As much as I love a good challenge, I’ve learned that some things are worth grinding it out for and others, not so much.

Pick your battles

You do not have to climb every hill or fight for every cause. Not every challenge deserves your energy.

The key is knowing the difference between good hard and bad hard—the challenges that push you to be better versus those that leave you defeated and depleted.

Sadly, “bad hard” challenges are all around us:

• Initiatives with no support

• Leadership roles with no authority

• Workplaces that encourage (reward, even?) grind culture

• Toxic bosses, toxic peers, toxic anything

These may feel like challenges you uniquely can overcome. They may get some people, but not you—you’re better than most.

Or they may feel like a personal failing. If only you can do better, work harder, prove yourself—then you’ll be able to overcome them.

Not likely. And no.

No matter how much it feels like it, it isn’t about you. And trying to fight your way through might work in the short term—if at all—but it comes at a high cost.

Rise to the challenge

But some challenges are worth fighting for.

They can be equally uncomfortable. They may rattle your confidence and trigger your imposter syndrome. They stretch you in ways you didn’t know were possible—and aren’t entirely sure you can handle.

These challenges push you to learn and ultimately, to grow.

Like my new job. It’s a ton of work—building a GTM motion from the ground up, educating an industry, and transforming early wins into scalable growth.

I’ve spent seven of the past nine weeks on an airplane. 😳

But I enjoy the folks I get to work with every day. I love being back with my higher ed community. And I believe in what we’re building and the value it can offer institutions and most importantly, students.

I wake up every day feeling like the work I’m doing matters—to my company and to the industry that I spent so many years serving.

That’s hard work worth pursuing.

Bonus read: In the midst of challenges sometimes the best thing you can do is let go of preconceived notions and “if only” to make space for what serves you now.

Cover photo by Frankie Cordoba on Unsplash

Which means they’re getting announced at colleges and universities around the country right about … <checks watch> … now.

A retirement announcement creates an opening for organizations to reshape the future and for next-level leaders to step into it.

In theory, anyway.

That ability to step up often comes with a caveat—the dreaded “interim” title. It can trigger your imposter syndrome and surface all sorts of other feels:

Is it right for you?

The real question isn’t whether you’re capable. It’s whether the role serves you.

To take the role or not, that is the question—and the answer depends on your motivation:

• Are you interested in testing your leadership at the next level, in a low-risk way?

• Do you aspire to become a [insert role here] and want to gain in-role experience?

• Would you want—or not want—the permanent position?

• Do you want to work for, or have anything to learn from, the leader above you?

There’s often very little risk in taking an interim role. You get to try it on—while still having a position to fall back on if it doesn’t work out. Whether you’d want to return to your current position after having experienced the higher-level role is an entirely different question, however (and one best left for another time).

From interim to permanent

There are no guarantees with interim positions. Some organizations prioritize internal promotions and will want to move you from interim to permanent once you’re able to prove yourself.

Other organizations view the interim title as truly short-term and separate from the search for a permanent leader. But your incumbent experience could still give you a leg up. After all, you’re already in the seat, doing the role—you’re a known entity.

Being known can also work against you. Your reputation—or your alignment with current leadership—may be too much to overcome. Some organizations will want an outsider to come in and make a change—particularly if the team is perceived as needing improvement.

In some cases, the interim is charged with making changes that are likely to be disruptive and unwelcome—clearing the way for a new leader to come in without having the taint of that change on them.

Understanding your organization’s stance on interim positions—as well as the charter for the person in the role—can help you decide if this is the role for you.

Making the call … and what happens next

In most cases, there’s far more upside than downside to saying yes. The experience can position you—for this role or the next one, in this organization or another.

Once you’ve decided to take the role 😉, you might find yourself wondering:

• Should I make changes or simply “hold the fort” until a permanent leader is appointed?

• What should I be aware of or consider as I step into the role?

• What happens if I don’t get the permanent role?

All great questions! Stay tuned for the answers in an upcoming post.

I’ll tackle these questions alongside any others you might have—send them to me directly or post them in comments below.

Bonus read: Every high-achiever I know struggles with imposter syndrome from time to time. Whether an interim or permanent role—you’ve got this!

I was a voracious reader when I was young, in part because I grew up without a television. Books were my entertainment—and my escape.

These days, I mostly read short content: articles in the NY Times or the Atlantic, Substack blogs, LinkedIn posts (more on this below). The usual stuff.

I still love books, but my eyes are often bigger than my stomach when it comes to them. (Metaphorically speaking, of course.) Case in point: I have a large and ever-growing stack of books I’ve amassed over the past year (or few … cough, cough) that I want to read.

Despite that, my wife and I will undoubtedly find ourselves in one of Seattle’s lovely independent bookstores within the next month, buying a few more.

And yet I want to know …

What have you read recently that you loved? What books should I add to my list for 2026?

My reading preferences tend toward social justice-related nonfiction and autobiographies. I’m listening to more books (64% in 2025) than I’m physically reading these days, but I’m hoping to turn that around this year.

Unlike my 2024 books-in-review post—where I hated on Atomic Habits—most of the books I read in 2025 were good in their own way. Two were real standouts, however:

• Some People Need Killing, by Patrica Evangelista. The god-awful title kept me from picking up this book for a long time, but I eventually broke down and listened to it. It. Was. Amazing. Also horrifying, but wow—Evangelista is quite a storyteller. I learned so much that I didn’t know about the Philippines and the extrajudicial killings sanctioned by President Rodrigo Duterte. There are some similarities to the U.S. today (sigh) but also some reason for hope.

• Framed: Astonishing True Stories of Wrongful Convictions, by John Grisham and Jim McCloskey. I technically finished this book in early January, but close enough. Any shred of faith I had in our criminal justice system was completely shattered by this book. Grisham and McCloskey provide detailed accounts of 10 wrongful conviction cases that will absolutely blow your mind. In each case it’s unfathomable how any one of these individuals could have been charged—much less convicted.

My 2025 reads

In total I read one more book in 2025 than in 2024, but not nearly as many as I had hoped coming into the year. Here’s a complete list of books I listened to or read, in alphabetic order:

• Automating Inequality: How High-Tech Tools Profile, Police, and Punish the Poor, Virginia Eubanks (audio)

• Creep, Myriam Gurba

• Crook Manifesto, Colson Whitehead

• Crying in H Mart, Michelle Zauner (audio)

• I Hope This Finds You Well, Natalie Sue (audio)

• Invisible Women, Caroline Criado-Perez (audio)

• Moral Ambition, Rutger Bregman

• Presumed Guilty, Scott Turow

• Reset: How To Change What’s Not Working, Dan Heath (audio)

• Revenge of the Tipping Point, Malcolm Gladwell (audio)

• Some People Need Killing, Patricia Evangelista (audio)

• The #1 Lawyer, James Patterson (audio)

• The Many Lives of Mama Love, Lara Love Hardin (audio)

• The Next Day: Transitions, Change, and Moving Forward, Melinda French Gates

What did you read in 2025, and what’s on your reading list for 2026? Inquiring minds want to know!

More on LinkedIn posts

Call it an occupational hazard, but I spend a lot of time on LinkedIn these days.

So it’s surprising that I missed this much-hyped post from Matt Shumer about the imminent disruption coming with AI. I just finished reading it this morning, alongside a thoughtful response from Ann Handley.

And I have So. Many. Thoughts. From my experiences in start-ups—both in the late 1990s and today. From my time as a CIO helping universities navigate technology change. From my experience using AI every day. And from the perspective of what this means for us—and requires from us—as leaders.

But I just read the post and don’t have time to meaningfully reflect on it and capture my thoughts for you. So expect to see more from me on this topic in the near future, hopefully as soon as next week.

It’s an important conversation we need to be having—as humans, as educators and education administrators, and as leaders—and I’m eager to engage with you in it.

If you enjoy Some Guy Named Rae, please share it with a colleague or friend! I’d love to continue to grow a community of like-minded leaders who can learn from each other.

Share Some Guy Named Rae

Totally kidding. Almost no one loves performance evaluation time—not managers, not the employees being evaluated, not even HR (can you say “huge risk?”).

And yet here we are, at the beginning of another year and another performance evaluation season (unless your fiscal year does not coincide with the calendar year, in which case these observations still apply—just not right now).

The intention of performance evaluations is generally good—it’s a time to reflect on how you showed up at work over the past year and set intentions for the year ahead.

The execution, however? YMMV. A lot.

I don’t know that I’ve seen a truly good performance evaluation process across my many years of leadership.

Some are too short to be useful, others are onerously long. Some are extremely rigid, others too free-form. Some are completely manager led—often with little to no employee input—while others lean so far toward everyone but the manager that they fail to connect the dots to the actual work.

Regardless of how imperfect the process may be, there are things you can do as a leader to help you and your employees make the most of performance eval time:

• Take your time. The very least you can do is give your employee thoughtful feedback, and that takes time. A colleague recently told me they just “jot down some quick notes” immediately prior to the review session. Since it’s an informal review it’s no big deal, right? Wrong. “Quick takes” risk recency bias—among plenty of other forms of bias. If you’re going to do the review, give your employee’s last 6-12 months of work the reflection it deserves.

• Consider others’ input. People show up differently with their managers than they do with their customers, peers, and subordinates. Even if you don’t have a formal 360°review process, there are still plenty of ways to gather this information, directly or otherwise. When asking for feedback, pay attention not just to what people say—but how they say it. And what they don’t say at all. Observe email exchanges, meeting interactions, and unprompted accolades your employee receives. You’d be surprised what you can glean when you start paying attention to the signals.

• Be effusive about strengths but selective about growth areas. We all have annoying little habits as well as an array of things—big and small—that we can improve on. Not all of them are equally important. Some gaps may be foundational while others are next-level. Work to clearly identify the one or two growth areas that will have the biggest impact on how your employee shows up over the next year and help put them on the right path to achieve their longer-term professional goals.

• Incorporate employee self-reflection. Asking your employee to share their professional goals in advance—as well as reflect on their strengths and growth areas—can be extremely useful in helping you calibrate the conversation. Some people are incredibly self-aware; others, less so. Some are blissfully unaware of their shortcomings; others focus entirely on them. If you have a great employee who is hyper-focused on their weaknesses, you don’t need to pile on—spend your time boosting their confidence, instead.

While performance evals shouldn’t be the only time we’re giving feedback, they can create deliberate space to consider what comes next.

Maybe that means doubling down on what’s working. Or maybe it’s time to course correct and try something different. Either outcome is fine. Both, even better.

Used well, performance evaluations are less about compliance and more about care. Their value isn’t in the form, the rating, or the process itself—it’s in the time spent reflecting and setting clear intentions for the year ahead.

Bonus reads: Both low- and high-performers need guidance. Here’s how to approach conversations with each:

The question came from a good place.

If we’re doing our jobs as leaders, we’re fostering an inclusive workplace where employees with a variety of backgrounds, life experiences, perspectives, and political views all feel valued and safe.

That necessarily means we, as leaders, shouldn’t bring our personal perspectives and politics into the workplace—because neutrality is how we create inclusion. Right?

Sort of. Maybe? Not so much.

So many issues we face as individuals and as a society are complicated, and the “best” way to address them depends on the perspective you bring.

Some are deeply personal, where the best answer is the one that’s right for you. Others are societal and—no matter what any one person or group claims—there are multiple viable paths forward, each carrying its own tradeoffs.

But there are also times when there are clear answers. Times of absolute right and wrong. When we’re in a battle of good versus evil.

In those moments, we must take a stand.

No matter who we voted for or our views on social safety nets, tax structures, or immigration reform, we can agree on the basic dignity of human life.

We can agree that all people should be treated equally, with respect and an inalienable right to life, liberty, and the pursuit of happiness.

We can also agree that no one should lose their life—be beaten, choked, or shot to death—simply because they’re gay, Black, or exercising their constitutionally protected right to protest.

There’s only one right answer here.

And we have a responsibility to say so—as humans, as leaders, and as businesses.

Not only is it the right thing to do, our employees expect it of us. They want to know they’re working for people and companies that reflect their own values—and who will stand up for their dignity, and for them, when it matters.

So go ahead and stay silent on which political party you vote for—but stand up against injustice in the world.

Because some issues don’t have sides.

Bonus read: A year later this still feels pretty relevant.

I intended to write yesterday as I do every Saturday morning—with my wife in our favorite coffee shop here in Seattle—and publish today, like usual.

I even started a post on performance evals. But then news and videos started circulating about the shooting and killing of Alex Pretti by ICE agents in Minneapolis.

And in an instance, everything changed.

Everyday leadership topics felt meaningless. I couldn’t finish what I wrote, nor frankly could I write or focus on anything else.

A day later, I still can’t. I have no words. I am numb.

It shouldn’t be surprising that this is who we are as a nation. Remember George Floyd and the dozens of other black men and women who came before and after him?

And now, another person—Alex Pretti—has lost their life to government-sanctioned violence. People have lost a child, a brother, a co-worker, a friend.

This is not new—but it is always traumatizing.

Remember this when you head into work tomorrow. Your team members are dealing with trauma—again. You likely are, too.

So be sure to tread lightly tomorrow. Check in with your team. Give them space to share how they’re feeling. Cancel a meeting or two. Take a sick day (or a snow day!).

We’re dealing with a lot right now—and have been for awhile. It’s okay to feel numb. To not have words. To cry.

It’s okay to not be okay with it all.

RIP Alex Pretti. You were taken from this world far too soon.

PS: Please reach out if you need someone to talk to. I’m here for you. 💜

Sugarcoating wasn’t their style. It was characteristically blunt, if not the most eloquent advice. But also true.

As a leader, you’re not going to be universally liked. And if you are, well—you’re likely not making the tough decisions that your role requires.

Like changing strategic direction. Cutting programs. Redirecting resources from a beloved initiative. Or managing people out.

Let’s be honest

No one likes being told they aren’t performing in their role. Or being laid off—not because of performance, but because the organization is restructuring.

Folks really love that. 😳

Early in my CIO career, I led an IT restructuring that resulted in five people losing their jobs. The blast radius on this one decision was significant:

• The individuals directly impacted were (quite understandably) upset.

• Their immediate teammates were shaken by the organizational changes and sudden loss of their colleagues.

• Faculty were up in arms. Several emailed the president that this decision did not reflect our institution’s values—we were “family” and family did not behave this way.

It was absolutely the right thing to do for the organization, but it wasn’t easy. It pissed a lot of people off.

That said …

Don’t be an asshole, either.

Some people interpret the “if you’re not pissing people off …” saying as license to do and say whatever they want, whenever they want. Just … don’t.

Leadership requires conviction to do the right thing, and care for how people will be impacted by it.

It requires courage to make tough decisions, coupled with discernment to know the difference between an unpopular decision and the wrong one.

It requires transparency and the fortitude to sit with the discomfort that sharing unwelcome news creates—but sharing it anyway.

The hallmark of a good leader isn’t whether someone likes you.

It’s if they understand your decision-making process. If they believe you’re an honest broker. And if they respect how you show up …

Even if they don’t like a decision you’ve made.

Bonus read: Leadership isn’t for everyone, and that’s okay.

Cover photo credit: charlesdeluvio on Unsplash

It’s something I’ve been thinking about a lot recently: What do I want to accomplish in 2026, and perhaps more importantly, how do I want to lead?

At this time of year we are thinking about—and doing—a lot of things.

We’re tying off the year we’ve just finished: finalizing outcomes, summarizing learnings, and evaluating employees.

And we’re planning for the year ahead: setting strategy, building budgets, and organizing offsites to rally our teams around the year’s goals.

What we frequently forget to do is reflect on our own leadership and how we show up every day as leaders. We just do.

Sometimes that works. And sometimes it doesn’t.

We don’t have to lead by default. We have the power to change how we lead. It simply requires inspection and intention.

The questions I’m asking myself right now are these:

Over the past several years I’ve lost some focus on leadership as its own intentional practice. I’ve continued to lead, of course, but with varying outcomes and degrees of success.

I want to feel like I’m leading by design and not by default. For me, this looks like:

• Leading with empathy and compassion. The world is wild right now, y’all.

• Ensuring I know how each person on my team wants to grow and helping them build a plan to get there. Even if that means losing them to another company or role.

• Identifying and adopting practices to build cohesive and inclusive remote teams.

• Providing clear, honest, and direct feedback—while remembering to keep it balanced. I need to praise the good more and offer guidance for improvement.

If you haven’t inspected your own leadership in a while, now’s a great time to do it. What’s working well, and where could you improve?

Set a leadership intention for 2026 and then tell me: how can I help you get there? I’d love to hear from you.

Bonus read: A lot of decisions get made this time of year—don’t overthink them.

Cover photo credit: Tim Mossholder on Unsplash

There have certainly been some bright spots for me: I got married, visited Japan, and landed in a new role I’m really excited about. And two of these things happened in the last two months—which is a lot, even for me.

And yet, it has also been a year fraught with real challenges for so many people, myself included. We’ve struggled personally, professionally, and with what’s happening to our communities.

The SGNR posts that resonated with you most this year paint a picture of the kind of year it’s been:

1. Burnout

2. Leading Through Layoffs

3. (Re)Claim Your Power

4. (tie) Love The Work, Not The Job and Work Isn’t Family

5. The Secret To Change

Coming in just outside of the top five(ish), appropriately, was Leveling Up With AI. Because how could we possibly wrap up this year without talking about AI? 🙄

So many of you have shared your stories following the Burnout post. Publishing that post was hard and a little scary, so I truly appreciate you letting me know that it resonated with you. I’m grateful for your trust.

But also … it breaks my heart that so many folks are in the same boat. I wish better for you, and for us all.

I’ll be taking the next two weeks off from writing to enjoy time with family, relax, and prepare for the year ahead. I hope you can slow down too, catch your breath, and focus on what really matters: You.

See you in 2026!

PS: As I think about the year ahead for SGNR, I would love to hear from you! What types of content do you want more of, or less of? Is there anything specific you’d like me to write about?

Cover photo credit: Boudewijn Huysmans on Unsplash

We had just transitioned from 12 decentralized IT departments into one IT division, and it was … a lot. I was brought into IT from Continuing Education, so this was my first exposure to the rhythm of the IT business.

“Don’t worry,” he said. “It’ll slow down in October.”

Fast forward six months. I whined to my boss that October had come and gone and things were still incredibly busy.

“I didn’t say which October,” he wryly responded.

Just One More Week

I’ve spent the bulk of my career since then waiting for October to arrive. Waiting for things to calm down. (Spoiler alert: they never do.)

I’d like to say that I’ve found more balance since 2007—and maybe I have in the last couple of years, finally. But it’s still precarious, like a muscle I’ve only just begun to strengthen.

And right now I find myself once again pushing hard, trying to hang on for one. more. week. Maybe you are too?

It’s one week until schools close for the holiday break. One week until colleagues set their OOO replies and say “sayonara” to the year.

One more full week of work before attention turns anywhere but work—and everything gets pushed to January.

There’s Always Something

It’s easy to rationalize the push. Also … did I mention I joined a startup recently?

It’s a new job. There’s so much to learn. It’s planning season. I want to prove myself. And yes—I genuinely love what I do.

We never lack reasons for the busyness.

We convince ourselves that things will slow down and we’ll find balance once this month is over, this project is complete, or this role no longer feels new. Once this period, whatever it is, has passed.

But there’s always something else that takes its place, and that elusive slow October never seems to come.

For the Long Haul

A colleague nudged me this week to slow down and pace myself. They reminded me that I’m needed “for the long haul.”

It was a good reminder: this is a marathon, not a sprint.

Your team needs you to slow down too. They need you healthy. And they need you to lead by example so they can find their own balance.

Burning out early—or at all—isn’t a great option. Been there, done that, would not recommend.

We can be new, passionate about what we do, and carrying a heavy workload—and still set boundaries, step away, and take care of ourselves. We can create our own balance, even if that slow October never comes.

This holiday season, I hope you find a way to do just that—and carry it with you into the New Year.

Bonus read: A gently reminder to take time off work when you need it, not when it’s convenient for others (because it never will be).

Cover photo credit: Photo by Towfiqu barbhuiya on Unsplash

And that’s how I met Kyle for the first time.

Or at least, that’s how I met him face-to-face. Kyle and I had actually been following each other for years on Twitter, long before we ever met in person.

To this day, he remains one of my closest professional friends (who graciously gave me permission to share this story).

I was reminded of this story when I attended a conference last week and another colleague came up to our table to introduce himself. We, too, have been in each other’s virtual network for years but had never met in person—until now.

Connecting IRL

The conference I attended last week was fantastic. As someone who works remotely, it was nice to see and interact with people for a couple of days.

Yep, you read that right. Even introverts like me appreciate human interaction every now and again.

Talking to the numerous faculty, staff, and administrators—and the occasional student—who came to our booth was great. Truly.

What made the conference even better was connecting with colleagues and friends who I rarely see anymore—online or in person. It was in one of those moments that I realized …

I really miss Twitter.

It’s Just Not the Same

Over a vegan burrito lunch with a CIO friend I haven’t seen in five or six years, we chatted about the demise of Twitter—and our virtual professional community alongside it.

I’m on LinkedIn, as well as here on Substack. He’s on Bluesky and Threads.

They have comparable features in some cases and similar audiences in others. But the reach, engagement, and community we were able to build—it’s just not the same.

A few years ago I used this app to see my closest connections, and was so delighted by the community it reflected. Some of my dearest friends were in there, as were folks I’ve worked with and people I deeply respect.

Today, I keep in touch with some of these same folks on LinkedIn, others in private Slack groups or over text. A few read this blog (hi!). But others I rarely hear from anymore, and certainly don’t see in real life.

Which is sad. Because I miss learning from these amazing folks and reading about what’s going on in their lives—professional and personal.

For all that we’ve gained in our rapidly evolving digital world, we've lost some things too—including a place to build authentic connections and community online.

Which makes me grateful to once again be back in a role where I’m focused on higher ed. Where I’m able to attend campus meetings and conferences, live and in person.

And where I can reconnect with my community … sometimes over a vegan burrito.

PS: I’d love to know—where do you go these days to find and build your professional community?

Bonus read: I wrote this post in 2013, about the power of tech to bring us together. My family and I still do that weekly video call, but with an ever-growing number of disparate social platforms, algorithm-drive content, and increasing polarization leading to echo chambers—I’m not sure that I still believe that it can anymore. What do you think?