


26 Aug 2026 · 49m · 20 chapters

How to maintain identity, purpose, and culture during tech layoffs; what leaders should do (especially around empathy, trust, and communication) and what employees can do to stay psychologically resilient.
Shannon Olson is a partner at Henley Leadership (about 25 years old). She works with leaders/organizations on leadership development, executive/team development, and preparing for transformation and the “emerging future.”
Layoffs aren’t a one-time event; they disrupt trust, belonging, and dignity for a long time. Culture can’t be delegated—founders/leaders must stay present for messaging and human connection. Leaders should share “80% of the story” (including emotional truth) using frameworks like the Johari window. For individuals, the antidote is purpose outside the job plus maintaining relationships beyond the employer (“keep dating”).
A founder who didn’t “get into the business to be a boss” still had to lay off half the team; Shannon argues leaders must learn to “fire/lay off” with empathy. She also cites a client who built a diverse advisor network by asking weekly, “Who should I talk to next?”
Written by AI. May contain mistakes.
Explore the emotional and psychological impact of layoffs on individuals.
“There's going to be a level of, I'd say, stress, whether it's obvious or not.”
Learn about Henley Leadership's focus on helping leaders and organizations.
“for the conversation, and I hope that it can provide some of your listeners some sort of North Star in the midst of all of this sort of chaos and confusion we're in right now.”
Discuss the characteristics that define a startup and its evolution.
“You know, I guess eBay is technically a startup at this point, right?”
Understand the emotional challenges leaders face during transitions.
“And how do founders tend to come to grief, let's say, when they cross that line or when they have a hard time kind of accepting it?”
Examine why leaders must let go for successful transformation.
“And then, you know, and I think that startup phase, it's almost intoxicating because it's a small team and you're doing things and you see the results happening so quickly.”
Discuss the challenges founders face as startups evolve and grow.
“I was working for a founder closely and they were really extraordinary at like, you know, creating a vision and bringing people inside it.”
Explore how culture influences the handling of layoffs in organizations.
“So there's not I don't think there's a moment.”
Discover how layoffs can signify a cultural breakdown and the importance of trust, belonging, and dignity in organizations.
“that that human connection that willingness to stand in the fire that willingness to see the disruption and the upset.”
Learn how leaders can prepare for the tough conversations around layoffs and maintain empathy during the process.
“And I know there's, you know, I think there's always a craving for some sort of like checklist, like do these three things and it'll turn out.”
Explore how a resilient culture and a sense of belonging can help organizations navigate layoffs effectively.
“If you're employing people, you need to practice.”
Understand the importance of transparency and empathy in communicating the reasons for layoffs to employees.
“I keep returning back to this idea of belonging and dignity.”
Understanding the emotional aspects of layoffs and how leaders can communicate effectively.
“And in that framework, what they say is that leaders who share 80 % of the story and are open to 80 % of the feedback are highly effective.”
The importance of leaders admitting to their mistakes during layoffs and fostering trust.
“A non again, a not C-suite person like you are.”
How leaders can address emotional needs after layoffs to foster a supportive culture.
“And then there's all the factors that are outside of our control that come out of nowhere, that then lead us to have to take a different direction.”
Strategies for tech workers to maintain their psychological well-being despite layoffs.
“I want to pivot a bit and talk about, for any, but hopefully a lot of tech workers out there listening, kind of building or creating some mental and emotional armor for yourself.”
The value of engaging with diverse professions to enrich one’s understanding of work.
“established a lot of really great connections and my community is much larger than just what's in my work walls.”
Learn the importance of diverse perspectives in the workplace.
“Well, and if you look at like design thinking, that's like one of the like one of the aspects of design thinking, which is like just what are all the ways and all the diversity that's similar to this.”
Explore how building a diverse network can strengthen support systems.
“We're all in the same game called, you know, how do we have really great lives and get good work done without losing ourselves and our vitality?”
Discuss strategies to cope with uncertainty during layoffs.
“Networking is it's your network will save your life.”
Discover the importance of finding calm and stability amidst chaos.
“But I think like, what are they each day?”

Get the gist, explore an idea or ask about something said.
On Fund/Build/Scale, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00There's going to be a level of, I'd say, stress, whether it's obvious or not. There's going to be a level of wondering every day. There's going to be an energy drain. And I also honor that people need paychecks and have to go to work, right? And so I think there's a few things on the personal level that really matter, which is continuing to identify what's your purpose outside of your position. I think that's very, very important work to do. I also think if you're in that situation where perhaps you're questioning the stability or the sanity or the steadiness of the work, is are you also staying connected to the large network that's outside of that organization?
0:44I think that's just a wise move. you know, like sort of like, it's an old, you know, like, how do you tend to this relationship and kind of keep dating for the same time? You know, I mean, that's like the best way I can think of it right now is, is if they're not fully in and I'm not fully in, okay, well, we're going to, I'm going to hang in there. I'm going to bring my best work. I'm going to have a good time. And I'm going to be wise enough to keep my relationships intact outside of this.
1:11Shanon Olsen: To protect my heart. Yeah. That's right. Welcome back to Fund Build Scale. If you've worked in tech for more than a few years, chances are you've either been through a layoff, watched coworkers get laid off, or spent months wondering whether your term is coming next. But behind every workforce reduction are people making really difficult decisions and managers learning how to deliver difficult news to people and what could be the worst day of their life. And last but not least, employees are trying to figure out what happens next. My guest today is Shannon Olson. She's a partner at Henley Leadership, where she works with leaders and organizations navigating growth, change, and sometimes layoffs.
1:49Shanon Olsen: Shannon, thanks very much for joining me today. I appreciate the time. Hi, Walter. It's a joy to be here. I'm really excited for the conversation, and I hope that it can provide some of your listeners some sort of North Star in the midst of all of this sort of chaos and confusion we're in right now. Thanks. So for listeners who aren't familiar, tell us what Henley Leadership is, and what a typical week looks like for you? Oh, that's a great question. So we've been in business for about 25 years. We focus primarily on leadership development, executive development, and team development. And really who we work with are companies and organizations that are really dedicated to causing transformation in their systems.
2:30And so we help teams and leaders grow and get ready. And really, I'd say ready themselves for the emerging future. You know, how might we be ready as teams and leaders for what's three to five years out from now, instead of just what's being presented just in this moment.
2:46Shanon Olsen: How do you actually, the word startup seems like it's pretty loosely defined. You know, I guess eBay is technically a startup at this point, right? Or is it? I don't know. So in your mind, you have a framework. When does the startup stop being a startup? Yeah, I think that's a great question. I've been reflecting on this and part of it for me is almost when I think there's a moment where the managing of the relationships outgrows you. So at that startup phase, it's often just a small group of really dedicated, scrappy people wanting to make their dent in the universe. And at some point, the scope grows.
3:27And it's not about the product scope. It's not about revenue. It's not about any of that, but it's more about, for me, the relationships. And can you still sustain the level of trust and connection and alignment that you had in those early days? And I think there's like a Dunbar scale where it's like we can only manage about 150 relationships at a time. And there's something maybe in that where can we still get our arms around all of this in the same way? And I think that's a good kind of measurement, a simple measurement to be considering as you look to it. That's how I kind of see it. It could happen sooner or later than that, but I think that's one way of saying it might be time for us to look at how we might be running this business in a different way.
4:07Shanon Olsen: And how do founders tend to come to grief, let's say, when they cross that line or when they have a hard time kind of accepting it? Like that and because I feel like that's got to inform their decision making. They're still in that kind of scrappy, you know, we're all kind of, you know, ramen mode. And, you know, you've got really, you know, liabilities. And maybe you need HR at this point or other kind of real. Yeah, I think there's, I love this question. I love actually bringing grief into the conversations. It's one of those things that I don't think we give a whole lot of space to at work.
4:38But really, there's so many cycles of ending and beginning in any organization. And taking the time to pause and mark it as a moment in grief is really critical. I think that to the success. And I've seen various levels of grief. I think there's grief as far as almost longing for those simple days when it was so exciting and so innovative. And you felt like you were in the trenches around something really big. And there was a lot of ideation and creativity. And there's almost a high, I think, to that phase where like, it's fun are we gonna make it so I think there's that that where we get almost attached to that excitement and then I think for a leader or a founder there's grief as far as being bold enough and brave enough to say I might not be the one that can take this to the next phase or through the next era and really the wisest leaders are able to hold that and know that it's not a failure but it's really a sign of the success of the company and that there's something wanting to emerge that perhaps they need to call on call in you know additional resources for at the time um and so I think like tending to that grief is so important and naming it and being bold and almost saying there's now a line of demarcation we've arrived somewhere and how do we move through this messy middle this transition in a way where we honor what has been and and clearly start hiring and building towards what's next and not how it's been and that's what I can see those couple hot spots the the grief of the company that was the grief of the leader that maybe is like gosh I've held the reins so tight and now it's time for me to let it go and now what's next with a company
6:26Shanon Olsen: it's it's yeah it's hard because you know a lot of it's uh you can't not bring your attachments to work, certainly. And then, you know, and I think that startup phase, it's almost intoxicating because it's a small team and you're doing things and you see the results happening so quickly. It's very, you know, it's not like, it's not like, it's not like the job, basically jobs don't move at that pace. No. And there, and, you know, we're a small company ourselves. And I've even felt that for myself the last couple of years, like, oh, remember when it was like four of us and we just had these big, big dreams.
6:56And now we have processes and systems and bureaucracy and rules to follow and it's different. Yeah. Yeah.
7:02Shanon Olsen: So what gets lost when, when leaders try to hold onto that? Like what are, how does that manifest when someone is still, still thinking startup and they're past it, but they haven't really accepted it yet. What does that look like? Yeah. You know, I think the biggest thing I've seen is that the impact, I think when we don't consider who might we need to bring in at this phase of the business is that many of these folks who launched these beautiful businesses had an idea, had a product, had an offering, but they weren't necessarily wired to lead culture, to lead strategy, to lead people. So what I see is when they hold on too long, it's hard to attract the talent.
7:50It's hard to retain the talent. It's hard to really empower the people that need to step in and really deliver the work that is now in front of them. And full transparency, I think sometimes ego gets in the way, you know, like this is mine or some sort of ownership versus how do we care for this thing that now really has a life of its own? And how do we call in the right people to deliver this now? And so it's sort of like right person for that right era. Those were exactly the right people to launch it, to bring it to life. and the wise leaders now say, now who do we need, given what we see three to five years from now?
8:29Who are the right people to now take the next leg of this journey, like a wild relay race, so to speak. And so that's, I think, one of those tension points is who's willing to let go. There's this beautiful framework called the stages of transformation. And one of the pitfalls is that people hold on too tight for too long. So there's, you know, in order for something to really transform and grow, it has to be let go of. And this is one of the struggles that we see leaders grappling with is they just don't want to let go.
9:01Shanon Olsen: Are you building something that's hard to explain? It can be a sign you're working on something interesting, but it also raises the risk that you're missing out on fundraising, sales, hiring, and media opportunities. I help early stage founders sharpen the narrative. What matters? Why now? Who needs to care? And why they're the right team to make it happen. If you're preparing for a raise, a product launch, an important customer meeting, a panel discussion, or even a hiring push, I can help you pressure test your story before the stakes get higher. Visit the Fund Build Scale website to learn more or email fundbuildscale at gmail.com.
9:38Shanon Olsen: I remember one job I had. I was working for a founder closely and they were really extraordinary at like, you know, creating a vision and bringing people inside it. And people really, you know, changed their lives to come work at this company. And then things, you know, it was, I guess, 2000. There was a bit of a economic disruption, shall we say, called the. There was a thing. Yes, a thing happened. A thing happened. It wasn't great. It wasn't great to live through. But, you know, and the day came where, you know, we had to lay off part of the team. and and when the day came um suddenly uh the founder had a out-of-town business trip and i was saying goodbye to them in the lobby and i had to go upstairs and then lay off like you know half the team um and so what i realized like this person didn't get into the business to be a boss yeah like they founded that company because they had something they wanted to build um and i think that's is that that's pretty common i'm guessing right yes absolutely um the spark was the idea The spark was the dent in the universe.
10:38It wasn't like, you know what I would love? I'd love to manage 500 people. I don't think that's anyone's bright, bold idea in life.
10:45Shanon Olsen: But that gap, though, when is that gap between, like, you know, I'm a great builder and, you know, I'm not a great manager. Like, when does that gap start to become a liability? Well, I think that's the right question. I don't know if there's an exact moment. This is about this is about like can these founders or how can these, you know, initial group that launched these big ideas? Do they have, I'd say, their advisors, their allies, the ones who are going to be that sounding board outside of their own mind and say now might be the time? Because sometimes we don't know, you know, we're just in it and we're excited and we're driving and we're pushing.
11:18And we we've been in the water so long that we can't see that perhaps the conditions have changed. and so I think like who I see succeeds are the ones who do have a coach an advisory board somebody that's going to say now's the moment and have they done their own leadership development work have they done their own personal development work to be willing to release that to know that it's not a function of their failure it's not a function of something's wrong but it really is a signal that it's grown and it's time? And have they been proactively seeking out the right people on the way they're going to be ready to fill those shoes, you know, as they move?
12:00So there's not I don't think there's a moment. But do we have leaders and startups that are keeping their eyes wide open to is it still me? Is it still my job? Or is it now time for new, new, new energy, new people, new perspectives? Yeah, so it's not it's not so formulaic, unfortunately. But I can't say enough the importance of like having those that that those folks around you that are going to be honest um even if you don't want to hear what they're saying from your perspective is it is
12:28Shanon Olsen: it important that founders um like you know eat their vegetables and learn how to learn how to fire someone learn how to lay someone off or is it okay to delegate and you know kind of just gently like back into the bushes like homer simpson and the reason i ask is it's mainly because what i noticed with the change in that organization like the next monday was that like more yes of course morale was like in the toilet but beyond that there was the trust and the way people looked at the founder totally shifted it was like there was that that that there was the respect and admiration didn't exist anymore and so like what's what's the is there a danger for delegating like kind of these managerial things that managers have to do to somebody else because well I'm not really a manager I'm a visionary I'm a leader I'm a builder you know that kind of thing right well the one thing they can't delegate is culture Like there's no way to delegate that.
13:17So even if they're delegating, I'd say the practical, tactical, actionable items around layoffs, where they need to stay very present and very engaged are the things that you just mentioned, which is the trust, the safety, the values, the direction, even the messaging about why layoffs, why now and the impact on that. and that's all in that world of culture and really thinking about the health of the organization as a whole and so the the going into the bushes like homer simpson's like no no you do have to stay um you may not be the one sitting down need to be having the conversations but you are the one that's having to hold and share the larger message um and if that's a new terrain that that sort of that that human connection that willingness to stand in the fire that willingness to see the disruption and the upset.
14:10That's part of this sort of proactive development that I really think these founders and leaders should be stepping into because as you said, it's coming. There's cycles. So how might you better prepare yourself and be ready for all cycles of a business, the growth and the decay and the transformation and the stagnation? You know, how do you know that you can move through all those spaces? So for me, it's like, no, you don't get to delegate culture ever. That is in some ways like the one job of you. Yeah. Yeah.
14:42Shanon Olsen: Yeah. Go ahead. I was going to say the story, what I can hear is perhaps that what went missing is, you know, where's, where, where's the holding of that? You know, where's the care, the before, the during and after as far as the people. And that's all culture. I think in the prep call, you said, you described layoffs as kind of a cultural breakdown and not really an event or a milestone and the company's road. Let's unpack that a little bit. Because like, it's, you know, it could be a one-time event. It might not be a one-time event. What do you think, three things, and maybe these aren't even the top three things, but which of these three things tends to break first after layoffs?
15:18Shanon Olsen: Is it trust, like I said, or is it innovation? Like people, you know, they're bringing their best to work every day. Or is it something else like identity? Like this isn't the place I thought it was, you know, that kind of thing. Yeah, well, so yes to all three. Check, check, check. The first thing I'd like to kind of point out is, you know, for us over at Henley, we don't really see layoffs as a one-time event. Because often there's a lot of murmurings ahead of them. There is the so-called event. And then there's the impact for who knows how long after. And in some ways, it's, you know, it's an event for each person that was laid off.
16:00It's an event every time someone talks about it again. It's an event every time they remember that era. And so I think that's the first thing to disrupt is this isn't a day. This isn't like we did that on November 7th. That's not how it works. And so I think the trust is, I think, one. And in many ways, the paramount, right? And there's trust. And the other thing we're really seeing is this experience of belonging and dignity, really, which I really thought I belonged to this organization. I thought this was my team. I thought I was making an impact here and maybe not so much. And the dignity part is how did it all go down?
16:41You know, how did the layoffs happening? And one thing we're seeing is they're getting more detached and more cold and more isolating in nature. And, you know, I think there's this balance between how do you do layoffs within the legal constraints of what HR says while keeping humanity and belonging and dignity fully intact. And that's a dilemma. That's a challenge. And it's not an easy solve necessarily.
17:06Shanon Olsen: Empathy is kind of like, that's to me, like that's the top of the top of the pyramid here for talking about a layoff. It's not, it is, it's an, it's an economic and it's a psychological blow. How should leaders approach this? When, when is their time? Yes. So I think that there is, and I can't say this enough, there's like, how are you readying yourself for those hard conversations before the moment is in your face? Right? Like, and that is just, that's just future thinking leadership right there. Like, what am I seeing one, three, five years out? What are all the ways I might be confronted with really hard conversations and doing things I don't want to do?
17:44And what are my own values set against that? And how am I going to sustain culture in that moment? And so I think that I think what's happened, and this is honestly an opinion, is that we've gotten so oriented toward the legalities and the efficiencies of layoffs that we have dropped empathy and human connection and just giving ourself permission to just be in it with whoever we're having to have these conversations with. And I don't know what got us there. You know, I have my suspicions that it's, you know, lawsuits and all sorts of things that have happened along the way. But I think part of our roles in these organizations is we have to push a little bit.
18:27We have to talk to HR and say, this is my approach. How do I get that done within these constraints? It matters to me that I get to look this person in the eye. It matters to me that I get to bring empathy. It matters to me that they know that up until this very moment, they were very, very respected and cared about in this organization. How do I do that, given this is how you're saying it should go? And so there's some courage there of pushing back. What we say is sort of like, how do you challenge the culture? How do you how do you hold that as paramount? And that's brave. And as the person who's having the conversation, you're having your own ordeal.
19:05It's not a fun seat to be in, to have to let people go. And so you're holding both. You're holding your own experience, trying to get yourself sorted out, and you're holding theirs at the same time. And so I think for me, the first thing is getting yourself anchored in how do you want this to go as a leader, as a founder? And are you willing to push a little bit and say, I hear that's how it needs to go, but how might we get a little bit more creative in delivering this in a way that's much more aligned to who we are and who we have been historically? And I know there's, you know, I think there's always a craving for some sort of like checklist, like do these three things and it'll turn out.
19:39But you're dealing with human beings and you're dealing with situations that are so complex that it is more the only thing there is to do is root yourself in. This is our culture. This is my values. This is this is how I want to know that I'm OK with what I've done by the end of this conversation. And how do I make that work now?
19:55Shanon Olsen: Put yourself in the shoes of a seed stage startup founder. you've got maybe 30 people on the team and you, you didn't close that next funding round at the time you thought. And so you've got to let five people go. Yep. In a situation like that, like if someone, so maybe you're, are you not supposed to talk to those five people after you let them go? As I think HR might advise you like, okay, like they're dead to you now. And you can never contact them again. And if they reach out, like, don't, you know, is that, is that appropriate? Or would you push back against that? Personally me, I would push back.
20:28You know, And part of it is, and this is where it goes. This is like, if I think about when people launch a startup, they're so excited about the product or the idea that they sometimes perhaps might forget to start laying that strong foundation around, you know what? We want people, even if they exit this company, to know that they're like family to this and they're always welcome back. We want people like, what are the working norms that you're establishing really from day one? that maybe aren't even said out loud, but they're starting to get created. Because all of that is going to help inform that moment.
21:06So once again, deciding in the moment how you handle layoffs is way more challenging than having an exploratory conversation about how do we at company ABC deal with breakdowns, deal with disruption, deal with having to let people go. And so I think there is a pushing back. And some of that clarity might happen in those moments. Some of that clarity might happen like, OK, I'm face to face with it now. And now I realize how much this matters to me. And so if it's in the fabric of the company that folks who work with us, we maintain relationship with them post big events, then, yeah, you design it like that.
21:47And I can hear that it's pushing against a lot of norms, honestly. I mean, I think, you know, cut and run is easier in some ways. but over here we are challenging people to you know stay connected stay connected to the human being the empathy over there and in the long run it serves the business that every person that exits can look back and say I loved it I was sorry I had to go but I was I was treated with dignity I was treated with care I made a difference and I was treated really really well in a hard moment And that will help the brand, the business, the longevity of everything versus hundreds or thousands of people exiting and having just really harsh things to say about their experience.
22:30Shanon Olsen: If you're employing people, you need to practice. You don't want to, but you need to practice in your head. Like the day is going to come when you have to lay somebody off. You need to know how you're going to, because you can't, it's not jazz. You can't freestyle that. You've got to walk in with a plan. No. Yeah. And I think when you don't prepare, then you end up delegating it really to someone that really it's not their job. Exactly. And it's not, you know, it's unfair to you. It's unfair to the employee. It's unfair to the company. And, you know, our brains don't want to prepare for those moments.
23:02We like the big visions. We like the big ideas. We like the fun and the excitement and to settle our bodies and say, you know, how might we predict breakdowns and how might we be ready for that? They're not the sexy conversations, but they are the necessary ones. And we're small and, oh gosh, it is just a heartache. Anytime we've had to make that choice and we've never taken it lightly. And our focus has always been, how do we keep the culture intact? And it's hard work. It's not fast. It's not swift. It's not disconnected. It takes a bit more time, but then there's the legacy is intact, which is what we want.
23:45Yeah, that's great. Woo, big conversation. We're going deep. We're going deep.
23:50Shanon Olsen: I want to talk more about culture under stress, because that's kind of the nature of this, I guess, the kernel. Can your purpose, can your culture, not can you, how do you make sure, how do you make your culture more resilient enough? How do you make your culture resilient enough to survive layoffs? And how do you convince employees, it's real and not just the things, you know, people say when they got to lay people off. Oh, that's a great question.
24:23I keep returning back to this idea of belonging and dignity. There was a lot of talk about psychological safety for a long time. And, you know, our firm went back and forth about it because really there's nothing we can do to make people feel safe. That's really. But as leaders, we can create cultures of where people belong and there's dignity. And so I think that when a culture is under stress, if those two things are intact, you're much more likely to stay engaged, to stay in, to stay present because you know you have a place. Even if you know something's coming, you know I still belong here and you know that you're going to be treated well.
25:04and so I think that there's a there's some space in there for organizations to play where do people know that they have a purpose not just a position do people know that they are a contribution to where we're growing I mean I've heard recently of so many people that are pretty much working themselves out of a job you know like they're training AI to take over and it's a fascinating thing right now and they're doing it and they're doing it with they're in um and part of it is they're connected to the impact part of it they're connect they're clear that they're going to be taken care of at some point um and then there's some that aren't so clear and i'm watching the difference between how those two different humans engage with their company one is on for the ride and the mystery because they have a really great connection with their boss and there's a lot of open lines of communication and there's like they're willing to name the scariness of all of this and they have dialogue about it.
26:03So they're continuing to stay engaged in the organization. The others, there's fear, there's resistance. They're like, I'm not sure if I'm going to have a job. Their own survival is at stake. And it's two very, very different ways of engaging. The difference being one is they're tending to some belonging and dignity. The other is all about, I need you to produce more so that we can get this thing out of your hands. Transactional. Yes. Very different orientation. So I don't know if that really answered your question. And I'm sorry if I missed it. But you know, I think for me, this is where we have to double down, especially with the emergence of AI.
26:35I think that I think there's always a balancing happening. It's not an either or it's not tech or human, it's not AI or human. But how are we tending to the relationship and the task? How are we relational, not just transactional as a way of continuing to move it all forward? I actually think it all can coexist. This is a very new frontier we're in, but it's not an either or.
26:57Shanon Olsen: People want to reason why they're getting laid off. And actually, I think that's true, but I think it's actually emotionally not that true. The reason really isn't that important. It's just you got laid off, and that's the thing. The impact has happened. Yeah, exactly. Right, right. But so how much, I don't want to say storytelling, but when you offer a rationale for what's happening, when I see out there in the media, it's these mass layoffs of tech companies. It's horrible as far as the reasoning and rationale and the double speak. And it's just it's Orwellian. How do you counsel people to communicate the why?
27:33Well, I think, you know, there's a few things. And I love that you brought up empathy because I think that's one of the first things to exit the conversation. The other thing I hear a lot is like, well, we can't tell them anything. And I'm like, oh, there's a lot you can tell. Right. So there's an old model called the Jahari window. And the idea of the Jahari window, which is about how much information are we sharing and how open are we to feedback? And in that framework, what they say is that leaders who share 80 % of the story and are open to 80 % of the feedback are highly effective. and I would argue when I look at some of these like a layoff communications it's it's it's more like 20 percent story and a lot of wondering and our brains do need to know they're latching they want to the brain wants to latch onto something when something has happened to us and really on some level it's really as simple as like did I do something you know is it a failure of me did I miss the mark?
28:38Why me? Why now? Why did this happen? And so I personally would challenge leaders, HR departments to push themselves and say, what can we share? And some of the things that they forget to share is what is this like for us? You know, what led us here? Why this? Why now? What's our hopes for these folks? It's hard. You know, sometimes we just encourage leaders to tell the truth and talk about how hard it is and that this never has wanted to happen. And here we are. So there's I think there's the. Can you share 80 percent of the story? Can you stretch outside of just the technical aspects of a layoff and begin to speak to the emotional, the empathetic?
29:24Can you validate what it's like for all those people? Can you understand where they're at? And can you make space for some feedback before the exit happens? And that's that's the bold move is, you know, can you lay off people and then say, and we're going to be around for the next few days to clear this up. And we want to hear, you know, how you're doing. And that's that being open to the information coming back. And I think there's some risk in that. But I also think about startup folks, and it was all started on a risk. And so how do you pull that tenacity through all the way even into these conversations?
30:03Startups are risk takers, You know, so I say keep pushing on that standardized culture and see what else you can make happen in those moments.
30:10Shanon Olsen: Yeah, I always say like no one takes on people talk about how much risk founders take on. I think nobody takes on more risk than a startup worker. Sure. A non again, a not C-suite person like you are. That's right. You are rolling the dice. I mean, you are at the effect of whatever those leaders decide and you're putting your heart into it with them. I think that's such a valuable perspective. they've grown it right alongside but no like true true steak like they just get to work and uh you know are they treated with care yeah and appreciation yeah that line from the sopranos like you got the grief you should have got the gravy yes i know exactly but speaking of so i'm actually kind of curious about this also from your perspective um if mistakes were made should that be part of should that be part of the story as far as you know like for example we hired too quickly.
30:58Shanon Olsen: We tried to grow too fast or we made a bad bet with that product pipeline. Can you share that? Well, here's full transparency. Yes. I mean, we're biased toward relationship. We're biased towards transparency. We're biased toward partnership to the end. That's our bias over here at Henley. And I think that there's power in leaders claiming their breakdowns and their failures. And it's often a story, I think the more successful we get, the less likely we are to tell the truth on ourselves. And if that's surfacing your own humanity, and that's saying, like, we should have gone right, and we went left, and we did what we did, we did what we knew we could do in the moment, and it was wrong.
31:44And here's now the impact of that. And because of that impact, here's what we're sitting with. And you're like, you know, like you said, there's legal things that I'm not, I'm not an HR expert. I don't know that world. I just know human and leadership development. And, and so I think that that's in that transparency realm, that's in that 80 % sharing, we made some choices, we went too fast, we went too hard, we, we got ahead of ourselves, we missed this really important bit of information, we didn't know a pandemic was coming. Like, I mean, there are so many things, there's things that are within your control that you can admit.
32:16And then there's all the factors that are outside of our control that come out of nowhere, that then lead us to have to take a different direction. So I think that's a great approach. And once again, it comes back to, is that leader developed enough to do it in a way that is authentic and honest and real and not just smoke and mirrors because people will see right through that. And so, I think we've all seen those leaders where it just looks like lip service. You could hear kind of the BS in all of it in full transparency versus the one that's really, really owning their care of the people and the love of the business and that they made a wrong call and now they have to clean it up.
32:54Yeah. So that's my bias. And I also find like with the people that are at the effect of it, it gives their brain the answers the brain is seeking. Our brains need the answers. Even if we don't like the answers, then we can say, okay, it wasn't just me. There was choices that were outside of my control that led me here. And that's back to that dignity and belonging, You know, and that those leaders trust those people enough with that information. You know, it's a signal of trust. Like we're still in this together, even to this conversation, I think is really, really important.
33:27Shanon Olsen: I want to pivot a bit and talk about, for any, but hopefully a lot of tech workers out there listening, kind of building or creating some mental and emotional armor for yourself. Because I think, you know, as I said at the top of the show, these are not a, it's not a bug. This is how tech works. you will get laid off at some point if you work for enough tech companies. And so I guess for me, it's like having been in that situation, I think the first question I have, and I know you're working with companies and entrepreneurs, not the individual workers, but just switching your perspective for a second.
34:00Shanon Olsen: How do you remain psychologically invested enough to do good work without believing the corporation will love you back? And the reason I say this, so I live in San Francisco. Good question. I live here most of my life. And like, and when I go, like, I don't work downtown anymore. I don't go in the office. It's me and my bedroom. But when I did, I'd be on the light rail and I'd be sandwiched in between, you know, young people wearing, you know, backpacks and Patagonia hoodies and fleeces. And everything's got the logo embroidered on there. And they got the water bottle. And it's like, they carry the stuff with them every place, like totems, like talismans kind of thing.
34:35Shanon Olsen: And it's a huge part of their identity. and I do wonder about those people you know when I see them I'm like you're going to get laid off one day and you've got all this gear like mentally and physically that you drape yourself in but then a layoff comes and you realize like oh you know this is not my family so how do you say psychologically in the game to do a good job and be your best person that's such a big question for me what you just named Walter is that
35:09it's big because there's, I'd say, the large system called capitalism where we're trained to be workers. And in many ways, we've been trained that that's our purpose, that that's our use, that that's who we are. And we are to dedicate ourselves to an entity and make money and survive, right? And so when that gets removed, it strikes a deep survival. You know, it's our survival gets attacked. So for me, it's like, it's the big, big work of who are you outside of that system? You know, who are you? That's not your only worth. And it's tough. I mean, that is, I say it's a big question. It's like, I'm kind of like on the edge of my seat about this one because, yes, I'd say you can go to work and you can phone it in and you can work in a system that you're questioning is really there for you or not.
36:07And there's going to be an impact to that. As you can imagine, there's going to be a level of, I'd say stress, whether it's obvious or not, there's going to be a level of wondering every day, there's going to be an energy drain. And I also honor that people need paychecks and have to go to work, right. And so I think there's a few things on the personal level that really matter, which is continuing to identify what's your purpose outside of your position. I think that's very, very important work to do. I also think if you're in that situation where perhaps you're questioning the stability or the sanity or the steadiness of the work is, are you also staying connected to the large network that's outside of that organization.
36:55I think that's just a wise, wise move, you know, like, it's sort of like, it's an old, you know, like, how do you tend to this relationship, but kind of keep dating? I mean, that's like the best way I can think of it right now is, is if they're not fully in, and I'm not fully in, okay, well, we're gonna, I'm gonna hang in there, I'm gonna bring my best work, I'm gonna have a good time, and I'm gonna be wise enough to keep my relationships.
37:20Shanon Olsen: To protect my heart. Yeah, that's right. And I think that that's, that's healthy and vital and wise. And it's not really harming the company you're working with, because you're still bringing your best. But you're also, you know, taking good care of yourself. So I think that there's, what's my purpose outside of this position? There's also, am I tending to relationships and opportunities outside of this particular context? and that does push against a lot of the norms which is like loyalty and you should be in all here and not tending to anything else it's like well maybe but we're in an era right now where I think our community and our networks and our relationships really really matter and we have to keep those in really really good shape outside of just the ones that are in our work walls and I think you know if you have the means and if you have the privilege of saying you know what I don't think this is right, then you get to exit.
38:18You know, I personally wouldn't encourage anybody to necessarily stay in a situation that was causing them harm. And I also know that some people need paychecks. And so, you know, holding that tension for yourself. And that's why it's important to keep seeking what else is out there. And there's this, I think this change agility that we're in. There's resiliency, which matters. And then there's also like, can I just start rolling with the rapid changes that are going to be coming at us now. And this just isn't just the tech industry, but it's, I think just life is whole right now. So it's like, how do I be ready, embrace myself?
38:56And then how do I how do I stay flexible enough and soft enough that when they keep hitting, I can count on myself to get my footing underneath me. And know that I've established a lot of really great connections and my community is much larger than just what's in my work walls. Yeah.
39:13Shanon Olsen: Like if you were, if you were an employee in a large organization post layoffs, like what signals would you look for to indicate that the culture was actually recovering or whether it was actually time to, you know, fire up those, those dating apps? That's great. That's great. Well, I think like if I was as an employee, I would really focus on my relationship with my manager and even my skip level and begin to see how much I can start continuing to have transparent conversations with them. You know, is that 80 % being shared? And, and I think this is where, you know, can we pop ourselves out of the day to day grind and have those important conversations as employees too, and really say, you know, I need 30 minutes and I I'm going to take my 30 minutes and do a gut check on what I'm picking up on in the system.
40:07One of my clients has done that recently. They just have an ongoing conversation about AI replacing their job. And it's like every few weeks they check in about it. Because in many ways, their boss is learning as they're learning. But that connection is there. And that's a sign of not just a recovery, but at least they're in the flow of what might be happening. There's those touch points. And then I think, Walter, I think the notion of recovery is kind of interesting in itself because there's what we can control. And then there's what's out of our scope of control right now. And there's so many conversations that might be five, six levels away from us that we may never have access to.
40:49So in some ways, it's like, what are those immediate relationships that I trust that are going to be my ally that I can keep in constant dialogue with? And I don't I think that it would be wise just to check your own inner sensibilities about this at times and, you know, check in with people in other industries and checking with people in other industries is interesting for me because we work with a lot of utilities as well. and they cycle through all sorts of life and cycle through all sorts of things or healthcare was impacted by the pandemic. And so there's, how are these things being solved in other industries as well is I think a really wise move because it's getting more and more, in many ways, we're starting to be confronted with similar dilemmas and it's not so industry specific anymore.
41:39Shanon Olsen: I don't know if that helps. No, it does. It actually, it validates something I've thought and said for years, which is actually, most people I almost everybody I know for years in San Francisco were people I either moved here with you know for my tech job or people I met through other tech jobs and what I realized over time was like I started making friends who didn't work in tech and then and it completely enriched my life and deepened my understanding of work in general yeah so if you work in tech don't like go make friends with like a bartender or a waitress or or a salesperson like seriously or a nurse like seriously you need got to broaden your perspective because the work you're doing and And the way you're doing it is not typical in any way of like how work is supposed to be.
42:18That's right. That's right. Well, and if you look at like design thinking, that's like one of the like one of the aspects of design thinking, which is like just what are all the ways and all the diversity that's similar to this. And I think that's really great. We just held a conference, our first leadership conference a couple weeks ago, and it was great. We had like high school teachers and VPs of utilities and health care and property managers. And it was so rich for that reason. And mostly it was like, we're all in the same game. We're all in the same game called, you know, how do we have really great lives and get good work done without losing ourselves and our vitality?
42:54And so I'm with you on that one, Walter. Like, don't get convinced that there's that much difference over there and that you can learn from a bartender or a waitress or a nurse. I think that's brilliant. Really, really brilliant. Yeah. I had one client that there was concern and he started, there was concern about his role. And he started a game where every week he would just pick a random person of a conversation with. And then he asked that person, who should I talk to next? And he just followed that breadcrumbs for months. And the result of it was a really strong, diverse network. And he learned so much.
43:33And then, you know, when the challenges hit, he had 30 people to turn to that he'd had really robust conversations with. And what I loved is that he was guided by just the next person. It wasn't like him coming up with his list, but it was like, who should I talk to next? Like, oh, go talk to this person, you know. And to your point, it was all over the map. And at the moment, he couldn't make sense of it. Like, where is this going? And then it all made sense because then he had a really strong bench of trusted advisors that came from a huge variety of backgrounds. that he could turn to. And it was really, really great.
44:05So fun game. I say that's a fun game. It's just where should I go next? It's really great. Yeah.
44:12Shanon Olsen: That's good. It's a good story. Yeah. Networking is it's your network will save your life. Yeah. No exaggeration. Emotionally, intellectually. I mean, you name it. That's right. That's right. Yeah. If you're a technology worker and you're watching coworkers disappear and you're wondering whether you should stay. Um, kind of just, should I be exploring something? Um, and I think this is a lot of people that's the uncertainty is real and, but like the uncertainty of like what's beyond, you know, the parking lot, that's also, that's even more uncertain. So what, what are, if you were in that position, what would you be paying attention to most right now?
44:47Yeah. Well, I think the first is that it's not an either or, I mean, I think you can stay and explore. I think you can build new relationships and tend tightly to the ones that are sitting right next to you every day. Um, so I think that's part of it is disrupting that either or thinking is I'm either staying or I'm leaving or maybe, you know, maybe there's a million other ways forward. Um, there's also, I just think a rigor we're going to have to bring in this era of, of the unknown and, and, you know, how do we stay steady in that? Uh, Margaret Wheatley wrote a book called who do we choose to be?
45:22And it's really just sort of about this moment we're in right now, um, which is complex and difficult, whether you're looking at layoffs or AI or the environment or you name it, political landscape. And what she, one of her challenges is to start creating islands of sanity, she calls them, where in a world where nothing is certain and in a world where everything is changing so fast, how might you start gathering in these little pockets that are sane and steady and connected and you find some relief at the end of every day. And I, more and more, I see that needed. you know, do you every single day have this moment where your nervous system can calm down?
46:04Is there a group of people where you're like, I'm good, I'm safe, I'm good, these are my people, I'm going to be okay. Who are they at work? Who are they at home? Who are they in your neighborhood? And I think that's something that we've really encouraged people these last many years is we can't control the chaos. It's here, the volatility is here, the uncertainty is here, the ambiguity. But this is where it's almost like kind of back to basics again, like back to the relationship, the community, the co workers, the network, and being wise, and who you're sharing yourself with, and who you're in conversation with, and who are those that, yes, can honor that it's super messy and scary, but also are holding a future possibility at the same time.
46:51So that's like two things I think I would play with is begin to explore where you have that either or thinking like am I in or out or should I stay or leave um and that just knowing that it's not that anymore um you're being presented with a dilemma and all there is now to see like what's the opportunities in this and how do I keep exploring what possibilities I have right now and then what are your islands of sanity um yeah yeah I mean and it's a really great book it's not like a joyful book because it's just sort of a deep truth telling book. But I think like, what are they each day? It really, really matters.
47:26I mean, it could be anything like my favorite moment is like, I wake up in the morning and I walk into my garden with my cup of coffee and I look at my flowers and I'm like, okay, I'm steady. This moment all is well. And I'll do it again at the end of the day, you know, these practices or these human connections. Because it's not just in the tech world. It's a lot of disruption right now. And so I think there's just a call for that causing steadiness and causing settling in our bodies is really, really important right now.
47:55Shanon Olsen: Shannon, this has been such a great conversation. You've shared so many resources. I cannot wait to get these shown together. It's going to be really, really useful. I loved it. I loved being in conversation with you. I loved your perspective. And I just really thank you for, I think, I thank you for making space for this conversation and just naming something that in many ways feels untouchable or unmameable. So thanks for that. The Fund Build Scale theme is written by Michael Tritter and performed by Michael and Carlos Chárez. Michael also composed Ocean, the track he heard at the top. If you enjoyed the episode, please subscribe and leave a rating.
48:32Shanon Olsen: It helps more people find the show. You can get the Fund Build Scale newsletter on Beehive, follow along on Instagram, and if you have a guest suggestion or a question, reach me at fundbuildscale at gmail.com. Thanks for listening. Fund Build Scale is a production of Truth and Soul Media, LLC.
If you work in tech long enough, there’s a good chance you’ll go through a layoff. Either your own, or one that leaves you wondering whether you’re next.
Shanon Olsen, COO of Henley Leadership, works with executives and organizations navigating growth, disruption, and change. In this episode, we talk about why layoffs should be understood as a cultural breakdown rather than a one-day event, what happens when founders build companies they aren’t prepared to lead, and why CEOs can delegate just about everything — except culture.
I’ve been on both sides of this equation, so I asked Shanon about how to stay committed to your work without making your employer your identity, why it’s important to maintain relationships outside your company, how to assess whether a workplace is recovering after layoffs, and why staying in a job and exploring other possibilities don’t have to be mutually exclusive.
RUNTIME 48:52EPISODE BREAKDOWN
(2:05) When does a startup stop being a startup?
(9:37) If you're not ready to let someone go, you shouldn't be the CEO
(14:57) Why layoffs are a "cultural breakdown"
(19:56) How should the CEO behave after layoffs?
(23:50) Building a culture that's resilient enough to weather layoffs
(26:58) How to tell an employee WHY you're laying them off
(32:38) " Identify what's your purpose outside of your position."
(39:13) How to tell if your company is recovering after layoffs
(44:23) Should you stay or leave after layoffs?
📺 Watch this episode on YouTube: https://youtu.be/vbunRx4FZIQ
LINKS
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If you’re preparing for a raise, launch, important customer meeting, panel, or hiring push, I can help you pressure-test the story before the stakes get higher.
Visit the Fund/Build/Scale website to learn more, or email [email protected]
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