Leadership in tech is an exhilarating roller-coaster where shifting priorities, soaring AI capabilities, and an ever-evolving landscape keep us on the edge of our seats.
You don’t need us to tell you these past few years have been one wild ride. Tech giants like Google, Microsoft, Meta, and Amazon – yeah, the big shots – have all been making headlines with seismic layoffs that have shaken the industry to its core.
Who can forget Elon Musk’s acquisition of Twitter in 2022? According to Business Today, the $44 billion takeover came with multiple rounds of layoffs and a jaw-dropping 80% reduction in Twitter’s workforce!
Amidst this chaos emerges a burning question:
Can leaders in tech ever regain the trust of their employees?
And are there valuable lessons to be learned for CEOs and executives across all industries?
Today, we’re delving deep into these pressing issues through a candid interview with special guest Harry Glaser. Harry’s own $130 million sale of his co-founded company, Periscope Data, means he’s no stranger to the challenges, triumphs, and lessons of leadership in tech.
Now, Harry’s on a new mission, co-founding Modelbit – a trailblazing tech company empowering data scientists to unleash the lightning-fast potential of machine learning models.
Together with Mindmaven founder Patrick Ewers, they dive headfirst into the future of leadership in tech. Covering everything from Harry’s difficult lessons learned as CEO to his courageous outlook on deviating from the industry playbook.
Brace yourself to unlock a new paradigm of Human First Leadership, where empathy, compassion, and genuine connections pave the way to unprecedented success.
Let’s do this …
Navigating the Turbulence: Harry Glaser’s Insight Into the Chaos of the Tech Industry
Harry: “In some ways, I feel insulated from the chaos in the tech industry in the last year or so,” he shares candidly.
After the arduous process of selling his company in 2019 and subsequently working at the acquiring company for two years, Harry found himself amidst the Covid lockdowns and political drama of 2020.
However, he reveals that taking a break and starting a new company with his co-founder allowed them to be somewhat less directly impacted by the events unfolding around them.
Circling back to Patrick’s passionate curiosity about Harry’s deployment of Human First Leadership principles, even in the most turbulent times, he added:
“Leading with empathy is mostly a matter of wanting to lead with empathy and then having some well of experience, some reservoir to draw on.”
Harry acknowledges that the challenges he faced in the past provided him with valuable lessons and insights. The memories of previous crises, the mistakes made, and the sleep lost all played a role in shaping his approach to navigating difficult situations.
“I don’t know that there’s a philosophy or a silver bullet so much as wanting to do it and trying hard to do a good job.”
What Is the Meaning of Human First Leadership?
Seeking to explore the depths of Harry’s caring and empathetic nature, Patrick asks Harry about what Human First Leadership means to him in the context of being a leader in tech.
When asked to define it, Harry shares his perspective:
Harry: “I don’t know if I have a definition. I think that maybe one way to frame it is, there’s a context in which you are interacting with these people.
So for me, it’s a company, right? We have a company. I’m the leader of the company. We’re trying to achieve a business outcome. We’re trying to build something, build some software, sell some software, those kinds of things.
But I think there’s a recognition and a humility about the fact that the humans themselves and their journey through life and your relationship with them is bigger and more important than that.
The humans in their journey through life are more important than your business outcomes. And so just bringing that humility to every interaction.
So, when you get up in front of the company to announce some news – good news about a quarter, bad news about a layoff – they’re gonna take that back and integrate it into a life context.
They might be raising a family. They might be supporting their parents in another country. They might be trying to get a visa for somebody.
And this news is getting integrated into a context for them. It’s not about you and your company and getting to the end of the quarter.
It’s about: How does this help or hurt them in what they’re doing with their family – what they’re doing with their life?
That’s the real story.”
While acknowledging the importance of perseverance, competitiveness, and drive in achieving business milestones, Harry admits there is a wider context to be seen.
“To the person who is receiving the message from you, it is less important than ‘I came here on an H-1B, and I’m trying to bring over my family. Or I’m trying to send money back for my family. Or I’m trying to afford a house that’s big enough to raise my kids in.'”
Harry accepts, “Your business is not the be all, end all. I try to remember that when I’m having these interactions.”
Patrick: “Yeah, I find that actually exceptionally powerful because I would argue it’s relatively unusual.
Most people would say, ‘Well, look like, you know, we’re on a mission, and we need to achieve that mission. And in the context of our company, that is the biggest thing that matters.'”
Which Leadership Style Is the Most Effective?
Recently named one of San Francisco’s top-ranked CEOs by Comparably, Harry is a testament to the power of prioritizing relationships and leading with empathy.
But how do you make being a good leader part of your day-to-day life? Harry offers his insights on the matter.
Harry: “You just have it in mind every time you’re interacting with somebody. You know, we have a mission. We need to achieve that mission – and in the context of this company, it’s the most important thing that’s true.
But this is not the only context. It’s not the only frame.
While the mission may seem all important to you, it’s because your company and you started it, and you run it.
That’s not true for anybody else at the company. This is one step on their journey. They have another more broad context, and the journey is about achieving something for them that exists beyond your company.”
Excited by Harry’s mindful perspective, Patrick delves further into what it takes to become an effective leader. Including the transformative power of embracing the human element in every interaction.
Can Leadership Be Developed?
Are leaders born or made? This question has sparked countless debates, but for leadership in tech, there’s no denying the potential for growth and development.
Patrick: “You have trained yourself – or maybe from who you are, it’s natural to you.
But I think a lot of people that listen to us right now say, ‘I want to be that, but it’s harder for me because it doesn’t come naturally.'”
Harry: “Well, yes, that’s true. And it’s not right…
Leadership is not a born skill. It’s a thing you learn.“
Reflecting on his own journey, Harry acknowledges that, although he has been fortunate in life, he has also faced difficult moments. In these instances, there were times when he didn’t want to learn from those experiences or made them worse.
However, he emphasizes that there are pivotal moments that truly matter and leave a lasting impact on leadership growth.
Harry: “I’ve done a few layoffs in my time. One that was particularly painful because it wasn’t market driven.
It was my fault.
Having to go through those moments, and everybody remembers that. So you really want to bring that context to those moments.
But then also there’s key moments in the relationship with each individual … the recruiting process, any kind of termination process, whether they initiate it or whether you initiate it. Touchpoints at critical moments, milestones, promotions, those kinds of things.
Again, I would say take a moment and really put yourself in their shoes.
I’ve been on the other side of this, where my partner comes home from a tough day at work and relays some story. I’m all angry on her behalf. I’m angrier than she is at what went down in her workplace, in a context I don’t even understand and a decision I don’t even understand.”
Drawing from personal experiences, Harry highlights the importance of recognizing that behind every employee is a spouse or family member who is connected to their goals and home life.
By taking a moment to pause, reflect, and consider the other person’s perspective, leaders can approach conversations with greater empathy and understanding.
“Before you go into the room, take a breath and think about where they are coming from and what they want and, and what’s important to them.”
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Aligning Processes With Values: Building a Culture of Transformational Leadership in Tech and Beyond
Patrick: “So, let me throw in some sort of pragmatics that I would distill from what I’ve heard you say. The things that people can do.
Number one is to create a list of heavier processes that your organization has to run – like the termination of a person or any type of process that takes place regularly. Some of them we like, some of them we don’t.
One thing you can do very pragmatically is add the question:
‘How is this process going to impact that person?‘”
Harry: “I think that’s right. And maybe another thing you can add to those processes is:
‘How do we run this process in a way that’s in line with our values?’
‘And is running this process in a way that’s in line with our values more important than running some kind of tactical business outcome?'”
Harry shares a powerful example from his experience at Periscope, where the company decided not to provide severance to employees who engaged in severe misconduct.
Harry: “When you’ve had truly bad behavior, and we can all imagine what that might mean. Especially coming from, say, a manager at the company who, in those bad behavior actions, was unfortunately and wrongly representing the company. We just said, ‘I’m not paying severance.’
We don’t reward that, and I don’t care if that means that we add legal risk to the company. The company is willing to accept additional legal risk in order to act in a way that is in concert with our values.
This is not always in your control, but as the CEO of the company, you get to say which things are more important than your values and which things are not more important than your values.
And I promise your customers and your employees are watching.
It’s totally okay to just go with the industry playbook. But just recognize you have the ability to not go with the industry playbook and to prioritize your values instead if that’s what you so choose.”
Patrick: “Yes. To me, that feels like it’s a statement of courage, and often courage does get rewarded.
And again, this was a big example, and I really loved it because it’s encouraging everybody who’s listening like, ‘Hey, maybe I can do that as well.'”
What Are the Qualities of a Good Leader? Creating Habitual Practices That Align With Your Values
Delving into the practical aspects of leadership, Patrick and Harry emphasize the importance of habitually aligning actions with values.
Patrick: “Whenever you are deploying a new process before you feel like this is ready to be deployed, have a standard approach of saying:
‘Does everything in here feel like it’s aligning with our values?’
A lot of the examples you gave were heavy examples of where you keep the context of another person’s life, and there, it’s really warranted. It’s almost sad when you don’t do it there, but I think a power move is to do it almost on a day-to-day basis.
So, before you step into the meeting—let’s say it’s not just a regular daily standup or just a weekly one-on-one, but there’s maybe something that has a bit more weight to it coming up …
Just before the meeting—have a mini ritual of saying the things I’m talking about, what’s the context of the other person?
If you make that a habit, I think by nature you will become much more of an empathetic leader like you already are.”
Harry: “I think that’s right, and I think it does become easier. It becomes second nature.
You get hit in the head enough times with, ‘Wow, I tried to do that meeting on autopilot, and they got really upset. I didn’t even think beforehand why this might be upsetting news for them.’
It’s easy to assume that announcing that your company will be acquired is gonna be good news for everybody – because it’s good news for you. And it represents some step towards the achievement of the company’s mission, which to you is the all-encompassing goal.
But everybody’s going to be wondering, ‘What does this mean for my compensation?’
‘Do I still have a job?’ Because everybody knows, sometimes people are laid off in acquisitions.
‘Are we moving?’
‘Am I gonna get a new boss?’
‘Is that new boss gonna be good?’
And so mostly the way that people are gonna be feeling is not congratulatory, but anxious.
What does it mean?
And if you don’t have all the answers, you need to talk about when and how they’re gonna get all the answers.
Maybe there are shortcuts, but for me, I mostly just fucked it up over and over again until I finally learned through paranoia to think about these things so much that it became second nature.
So, I think it’s just practice, and I think it does become second nature.”
Patrick: “Yes, I absolutely agree. And the best way to get anything to be second nature is by developing it habitually.
Make it a habit, and you can’t help it because you do it so often that you don’t even need to think about it.
Very few people deploy relationship-based things in a habitual way. But, for example, what you do is exactly that, and I think that’s very powerful.”
How To Lay Off Employees With Empathy
Unfortunately, layoffs have become a recurring theme in the tech industry in recent years.
Drawing from his own personal experiences, Harry offers valuable insights on how to best deliver the message while successfully maintaining employee confidence during such difficult times.
Patrick: “You showed an amazing amount of vulnerability just earlier in our conversation here about saying that you had to do a round of layoffs, and the reason is because you fucked up.
So in that situation, how can you go about this in a way where you feel like you are aligning with the principles of empathy and of Human First Leadership in some form or other?”
Harry: “Yeah, it’s a tough thing. The particular layoffs that were hardest for me were the ones that were actually in a really good market, and we had just not hit our number. We had not executed as a business as well as we needed to.
As a result, we couldn’t afford all of the people that we had working for us. So we had to make a plan to reduce, I think, the number was something like 20% of headcount off a base of something like 120 or 150 people.
A lot has been written, some of it very good, about the tactics of that – and the tactics do really matter. The order of operations, what you do when – I would encourage you to really focus on that stuff and really get it right.
But I think the message is probably the thing where empathy becomes the message and the delivery of the message.
It begins with an acknowledgment that it’s your fault.
I.e. ‘It’s my fault. It was my fault because as the leader of the business, as the CEO, it was my failure that led to other people losing their jobs.’
Which is a relatively damning thing. I did such a bad job at my job that these other people are gonna lose their jobs … So this has to start with an acknowledgment and acceptance of responsibility with that.
But there is also a flip side, which is that the people who remain at the company are gonna have their confidence shaken in that moment. You’re not gonna fully restore all their confidence in one sort of all-hands communication. But you can’t leave them with this feeling of like:
A: Harry screwed up.
B: Harry really seems to be down in the dumps about it and really seems to be taking it hard.
Because then they’re gonna lose their confidence, and that’s gonna lead to a spiraling effect that’s bad for everybody.
So you need to, in one moment, acknowledge and take responsibility for the screw-up and how it happened and explain what happened. And also, announce a way forward for the people who are staying with the company in such a way that is confidence-inspiring for them.
I’ve seen a lot of leaders screw up in both directions. I think it comes from that same point of empathy, which is:
What do the people who are staying need to hear and feel in that moment in order to have as much confidence in you and in the business as possible?“
Patrick: “Yes. So, what do you do in that moment? What is that fine line that you have to walk?”
Harry: “First, you design a process that has as much empathy as possible. That means notifying the people who are impacted first in as empathetic a way as possible. I like to do it one-on-one in person or over Zoom.
I don’t generally believe in these sort of mass emails. Recently, as layoffs have become almost more normalized, I think there has been some leadership bad behavior where leaders don’t feel personally responsible and therefore do stupid processes where they just send mass emails or something like that. I don’t think that’s necessary.
So I like to do one-on-one with the person’s manager or someone senior in person. Have some respect for the fact that means that there’s gonna be a period of time where impacted people are learning, which means the news will get out. You wanna minimize that time, but you accept it.
Then you want to bring everyone to an all-hands, and then you want to tell them what happened.”
How To Communicate Change to Employees With Empathy and Confidence
Effective communication during times of change is crucial for maintaining employee morale and confidence. Looking to shed light on how leaders can best approach these situations, Patrick asks:
Patrick: “What do you do with those that now have shaken confidence in you and your leadership?”
Harry: “I think two things. I think number one, you tell them what happened. As an example:
‘As you may know, we failed to hit our sales goal. That does, unfortunately, mean that we had to make some cuts because we can no longer afford all of the people, all of the salaries that work here.
I took the decision to make these changes so that we would be in a financially healthy situation.’
Then I would go into why we missed the sales goal and what happened. Then, and probably most importantly, I would go into what is the plan for the coming year such that that is corrected.
And then – and this is maybe stylistic – but I would end it on a personal note of why I personally am optimistic for the future. I would bring that back to the long-term mission of the company, the values of the company, and why people joined the company.
Give them an emotional reason to re-buy into the company at that point in time.“
How To Regain Employee Trust After a Crisis
Patrick: “Yeah. Okay. How do you specifically address the situation of people in the audience you are addressing or wondering why you still are the CEO?”
Harry: “I think they will make a personal decision about whether they still believe in you – and that is a personal decision for them to make.”
Patrick: “But you also want to convince them. What have you done in that particular situation? Because you must have addressed that in some form or another.”
Harry: “Certainly. It’s pretty typical in those situations. As a stylistic thing, and I recommend this: I will always take questions from everyone in these forums.
And someone, feeling a little spicy, feeling a little burned on that day, will raise their hand and ask why you’re still the CEO.
I think you give a short answer, specifically why.
So you’ll say, ‘Well, I came up short. I went to our board of directors, and I told them we came up short, and I told them what my plan was. The board of directors made the decision that they believed in the new plan and that they continue to believe in me as the leader of the company, and so that is the reason.’
But then I would also go on from that into a more emotional discussion of the mission of the company and why I am glad they did that: ‘I started this company because I believe in whatever the mission is. I believe in the values that we built together, and it remains my life’s work to bring this to a wider audience.’
People need to feel validated by the question. So you need to give this sort of tactical answer to the question, which is why: We have a board, the board makes the choice.
But people really make these decisions and make decisions about where they work and who they spend time with based on how they feel.
So you want to end with making them feel, or attempting to make them feel inspired. Then they’ll make their own decision about whether they continue to feel inspired by the work.
After all that’s gone down, you will lose some people all after a process like this, and that’s okay too. That’s healthy.”
How Do Leaders Deal With Imposter Syndrome?
In times when business decisions haven’t paid off, it’s natural for feelings of imposter syndrome to flare up. You may question whether you are really the right leader for your organization, and if you have what it takes to deal with the situation at hand.
If you’ve experienced this in your career, or find yourself grappling with them currently, Patrick and Harry offer their insights to help you navigate through:
Patrick: “You need to remember that you have probably the most passion for the business than anybody else on the planet.
And that passion is one of those things that we see time and time again is actually what’s driving a company not only to survive but to actually end up becoming big.”
Harry: “Yeah, the imposter syndrome is real. I lost an enormous amount of sleep before the first time I had to do this. But what I would say to anyone is:
A: That’s normal. Everyone does.
B: Be your authentic self up there. Don’t watch videos of Steve Jobs and then walk in and try to act like Steve Jobs would, or whoever your favorite business leader is.
The people in the audience, they’re in the audience because they bought in already. They bought into you, and they know you, and they don’t expect Steve Jobs. They expect you.
What’s really confidence-shaking is when you get up there and act too brash or out of character. People can tell you’re putting on a show, and then you look like there’s some reason why you might want to put on a show, and that’s scary.
Just get up there and be yourself.”
Patrick: “Yes. Give yourself permission to be yourself even in the most dramatic situations like this one. Because if you don’t, people will sense it.
Some people will actually cognitively recognize it. Most will actually just feel it on a subconscious level. But that feeling is icky, uncomfortable, and bitter.
You will actually end up losing the one thing you have going for. And that is basically, they genuinely believe in you and trust you – and that’s the thing you need most.”
Harry: “Yeah, you do have quirks and weaknesses, but the people in the audience have already bought into those quirks and weaknesses.
They’re not expecting that, on this day, you’re all of a sudden gonna find a solution to that issue.
They’re hoping to hear genuinely from you what the hell is going on, what’s the plan, and why should we still be excited about this?”
Patrick: “And most people are probably looking for a reason to stay, not a reason to leave”
Harry: “Yes, I would agree with that.”
How Will Leadership Change in the Future?
Wrapping up this insightful chat between Patrick and Harry, it’s pretty clear: The leadership of tomorrow is knocking on our door today!
Just imagine the extraordinary impact you can have by embracing Human First Leadership principles. It’s about more than just talking the talk; it’s about actively practicing empathy, cultivating stronger relationships, and empowering your team to soar beyond expectations.
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