Stacking the Bricks Podcast EP40 - Worst Boss, Best Boss with Lauren Williams
15 min

In this episode…

This week I've got a quick brick for you today, on the topic of bosses.

One of the things I don't think we talk about enough is how the bosses we've had inform the bosses we become, and that includes becoming our own bosses too.

A few weeks back I had the chance to sit down with Lauren Williams from Workplace Harmony and the host of a very fun show called "Caffeinated Convos and Horrible Bosses" where she asks her guests to share their best stories about the worst bosses they've had, and try to learn lessons that can make us better bosses today.

Lauren and I talked more about my backstory and The Tiny MBA on her show, which you can go listen to at, and dig into her archive for more horrible boss catharsis.

But in today's mini-episode, I share:

- My horrible boss story, and how it informed my approach to business
- As well as the impact one amazing boss has had on my life in ways that still impacts me, more than 15 years later.

All that and more inside this caffeinated conversation with my new friend, Lauren Williams. Here we go.

Find Lauren on Social Media
Twitter: @LaurenShazzam
Instagram: @workplaceharmonyHR
FB: Workplace Harmony


Alex Hillman Alex Hillman: What is up brick stackers! Welcome back to a brand-new episode of Stacking the Bricks. As always, I’m your host, Alex Hillman and this week I’ve got a quick brick for you on the topic of bosses. Horrible bosses, in particular. One of the things I don’t think we talk about enough is how the bosses that we’ve had in the past inform the bosses that we become, and that includes becoming our own bosses too.

A few weeks ago, I had a chance to sit down with Lauren Williams from Workplace Harmony and the host of a very fun show that she calls Caffeinated Convos & Horrible Bosses.

On her show, she asks her guests to share their best stories about the worst bosses they’ve had so we can try to learn some lessons that can make us better bosses today.

Lauren and I talked about my backstory and my book, The Tiny MBA, on her show which you can go listen to at and make sure you dig into her archive for more horrible boss catharsis.

But in today’s mini episode, I’m going to share two stories. One about my worst boss and how working for them informed my entire approach, not just to being a boss, but to all of the businesses that I run. And then a story about one of the most amazing bosses I’ve had my life, and ways that her mentorship continues to impact me today, more than 15 years later.

All that and more inside this caffeinated conversation with my new friend, Lauren Williams. Here we go!

Lauren Williams: Diving in here, I don’t know as an entrepreneur, if you’ve ever had a boss? So, I’m really interested to hear if you’ve ever had a horrible one, especially given kind of your career tenure and what you’ve been up to. I mean, if you started in web development, maybe you did, but I’d love to hear your horrible boss story.

Alex Hillman Alex Hillman: No, I have definitely had bosses and I mentioned that I left a company to go out on my own and that was in part because of my boss. I think what’s interesting about my personal horrible boss story is I had actually worked with that horrible boss previously, and we had a great relationship.

I went to Drexel University here in Philadelphia and one of the reasons I went to Drexel was the co-op program. The opportunity to learn on the job is very much my style. Probably maybe one of those early clues of entrepreneurship – learning on the job. And so, for my second co-op, I got a job at this digital agency. We were making websites that people I actually used. It was so cool, like THE definition of cool job. I had the most amazing coworkers, and that company went through sort of a rise and a fall in a fairly short period of time. They were on the rise while I was there. They grew very, very quickly. They went from like 50 to 150 employees inside of nine months – difficult.

Priorities shifted and leadership shifted and all of those things that, I mean, you work in this space. I know, you know exactly what I’m talking about. You know what broke without me having to tell you. There was an Exodus, there was a collapse and I loved this company and these coworkers so much, I hung on for dear life. When they finally ended my contract, I was like, well, what do I do I do now? I don’t really have a network in this industry other than this company. So, I started reaching back out to people who had left, which included a group of about six former employees of the same company who had spun off into a new agency.

I gave them a call. I was like, “Hey, what’s going on?” And they were like, “Not much. How are you?” And I was like, “Just left work for the last time. Can I swing by for a quick chat?” And so this wasn’t even a job application so much as I kind of rocked up to the office and I was like, “Hey, remember me, I’m suddenly available.” I actually ended up being their first full time employee, for a brief period of time.

Lauren Williams: That’s exciting!

Alex Hillman Alex Hillman: But, what I learned is that the way people interact and treat each other when they are coworkers is not the same as the way they interact and treat each other when they have a position of power.

My direct boss, who is someone who I had a good relationship with at the previous company, was now basically the sea level of technology at this now small, but very ambitious firm and he was drunk on power. I can say a lot of this post, I didn’t know why it was so stressful at the time. What I can say now is there was no North Star, it was all reactive, responsive, doing whatever the client asks for, never pushing back. That shit would roll downhill and hit me. Even as the team grew, part of it was, he felt like he could come to me because we had that relationship previously, but the dynamic had changed so much. We were no longer peers. It was positional and it didn’t work.

It was a combination of me really disagreeing with a lot of his decisions, but him not wanting to hear it from somebody who he perceived as below him.

Lauren Williams: That’s awful.

Alex Hillman Alex Hillman: Then on top of that here were a lot of conversations where I was like, “Look, it’s pretty clear that we need some team leadership as we’re growing out some of these projects, and I haven’t done that before. That’s not my expertise, so I won’t pretend, but I really want to learn.” There were lots of promises that I could, you know, on the next project I could lead the team. And then it wouldn’t happen. It became a pattern.

What sucked about it was I loved the work for the most part. I could verify that I love the work because I was doing the same kind of work as a freelancer and I could go home and build websites and stay up all night because I loved it. At work, it was like when you’re in grade school and you’d stare at the clock and it felt like it wasn’t moving.

During the day doing the same thing where somebody else was in there control and the way they were making decisions, I not only disagreed with, but that we could not find common ground and the relationship had been so broken, it was miserable. And it was the biggest thing that pushed me to say, if I’m happy in the evening with my moonlighting work and miserable during the day doing effectively the same thing, and the only thing that’s stopping me from making the same or more money in moonlighting is this pesky day job that’s driving me nuts, why wouldn’t I just peace out of here and go do my own thing. And that’s what ended up happening.

Lauren Williams: That’s amazing. I think it’s amazing for a couple of reasons though, to have the kind of foresight to say, I need to do this. I need to follow this. This brings me joy. This gives me flow in my work. This makes me extremely happy. This part of the day stuff isn’t making me extremely happy. It doesn’t feel good. I work for a jerk and then I’m left cleaning up the mess he makes or dealing with his reactive nature versus someone who’s going to cultivate me and elevate my game and help me.

So I just think that’s awesome. It’s a scary jump to make for sure, but it sounds like it was the right choice for you and it sounds like you definitely learned a lot about leadership through that.

Alex Hillman Alex Hillman: Absolutely. I can say for certainty that that experience has informed the kind of boss that I am. I’ve got a small team, but it’s so important to me that they feel like they can push back if they disagree with my decisions, I want to hear it. Ultimately, I hired them because they’re good at what they do. I should trust them to do their job.

I’ve said to them, point blank, “If I’m ever driving you crazy, you have permission to tell me and we can work together on what I need to change, because ultimately I’m here to support you. You’re here to support the business, but if I’m doing my job, it’s to help you do yours.” There’s absolutely a direct line from that experience where I did not feel that and that’s why I went out on my own to now I’m in a position where I can make experience better for somebody else. It’s important to me. I think that negative experience is a big part of why.

Lauren Williams: Yeah, I completely agree. What about flipping it on the other side, the best person you’ve ever worked for? Or really great leader you had the pleasure of knowing in your career?

Alex Hillman Alex Hillman: I’ll actually go back to that first company of the agency that went through the rise and the fall. I had a boss and I’m going to name her by name because she is amazing. Her name’s Sherri Alexander and Sherri was my co-op mentor effectively. She took me, who was eager to learn, but knew so little, and she provided a space for me to learn and grow and be challenged and to take on projects that were probably just beyond my threshold of capacity, but to treat it and frame it as a challenge and to show that she trusted me, that I could learn and that she could provide me with learning resources.

I mean, again, I think about so many things in my career that have informed other parts of my work and the culture. There are authors whose books I read on the first day of work because Sherry gave me a book and those authors are people who heavily influenced my work, not just as a web developer, but as a creative person and an entrepreneur. Now 15 years, almost 20 years later, some of those people are my friends.

I can track that back to Sherri introducing me to those people and saying, “This is your Pantheon. These are people worth looking up to”. To have a boss who never for a day treated it as I never felt like she was telling me what to do. She was telling me what needed doing. That distinction and that leadership style, I think about the things that informed the way I lead now.

I owe a lot to Sherri and actually in the last 12 months or so – maybe it was a little bit longer, but sometime last year, Sherri and I got a chance to catch up on a video chat and just hear how things are going. It was really, really nice to be able to say, thank you.

Lauren Williams: Oh, that’s great!

Alex Hillman Alex Hillman: She had said, when we caught up, that she had a lot of fond memories of the way we worked together. I don’t know how many other co-ops that she got to have that relationship with, but I was able to say to her with confidence that there’s so much good in my career that even if the through line is not obvious to you, I can connect it to the way you handled the situation or something you suggested I try.

She definitely emboldened me with a sense of experimentation on the internet too and the idea of if you don’t know how to solve a problem; the answers are there. You just kinda gotta go look for it, poke at it, try it and figure it out. But the other part that I honestly don’t remember if she told me this explicitly – but the people she told me to follow certainly did – which is to share what you know, and share what you learn along the way.

Obviously, that had supported her, it supported me and it became a big part of my business and ethos to write and blog as I’m going along. To record podcasts and things like that and to make a big part of my work, whatever I’m learning, if there’s a chance that could be useful to somebody else, I want that on the internet because I want some of my work to extend to beyond me and be in the hands of other creative people, other entrepreneurs who are a few steps behind coming up going, “Oh, I’m not the only one who ran into this problem and now I can understand the solution a little bit faster and then get back on my way.” My hope is that they feel that and pay that forward as well.

Lauren Williams: Alex, that’s such a powerful story and such a testament to Sherri as a leader, and the fact that you saw all the ways she was empowering you, but then you used that and you’re able to apply it and you were able to go back and thank her.

A lot of times we have guests on the podcast who know their favorite boss, can name them, name the years they worked with them, but haven’t had the chance to go back and say, thank you. I think that goes a long, long way. I think that’s just such a cool story. Thank you for being so open and sharing that with me and our listeners. That’s just great!

I’d love to also find out what you’re drinking. I know you’re a coffee drinker like me and we’re both kind of close to Philly. So, are you a La Colombe fan?

Alex Hillman Alex Hillman: So we actually have a custom roast of coffee for Indy Hall that I’m drinking. We have a collaboration with Herman’s Coffee in Pennsport who are amazing. Actually, Herman’s was founded by a former Indy Hall member, Mat Falco and their coffee is amazing. And so, we have a custom roast that they did just for us to call JFBI - Just F’ing Brew It, which is a little pun on my mantra – Just F’ing Do It. So, I’m drinking myself a cup of Just F’ing Brew It.

Lauren Williams: I love that so much! Oh my gosh, that’s the greatest ever!

Well, Alex, thank you so much. Thank you so much for sharing all the things today. I am so glad we were connected. I’m so glad you were able to be a guest. I can’t wait to learn more about you. I can’t wait to connect further with you and I’m excited for our guests to also check out your book.

So best of luck to you. Keep on grinding and I’ll talk to you soon!

Alex Hillman Alex Hillman: Thanks, Lauren. I’m glad to be here and hope you have a great rest of your day!

If you enjoyed that episode – and I hope you did – I’ve got a couple of quick things before you go. The first of course is making sure that you have your very own copy of The Tiny MBA. If you haven’t ordered it, I’d love it if you did, and you can grab a paperback or ebook at Tiny.MBA.

I also hope you’re subscribed to this show. We’re going to be releasing more episodes like this one with other creators and entrepreneurs, just like you and I’m going to be talking with them about their favorite lessons in The Tiny MBA, learning what’s going on in their world and sharing it all with you. You can search for that by looking for Stacking the Bricks wherever you get podcasts.

And one last thing, check out the Stacking the Bricks website, we’ve got a great newsletter with new articles coming out every week or two following on a lot of the same topics and themes that we talk about right here on the show. You can do that by going to

I hope you have a great rest of your day and don’t forget to keep on stacking those bricks!

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