Leading Design at a Silicon Valley Startup like Michael Scott
I’m here to provoke you to embrace unorthodox approaches when you lead the team. Aren’t common leadership styles boring?
Forget Bezos, Musk, and Zuckerberg. The real MVP of leadership might be hiding in Scranton’s Dunder Mifflin: Michael Scott from ‘The Office’. Yes, the awkward king of cringe and chaos. Now, before you throw out your leadership handbooks, consider this: What if this self-proclaimed “world’s best boss” character had some unexpectedly valuable ideas for being creative in leadership?
Well, here’s a confession: Looking back, as a design team lead, I found myself channeling Michael Scott more often than I’d care to admit. Don’t judge! :)
I may not always know what I’m doing, but I do know how to make people laugh. And sometimes, that’s all it takes to build a great team.
Leadership studies often overlook the unorthodox. Can a sitcom character written to just make you laugh every episode while doing weird stuff prove some value? This is the question I am here to challenge today. I’m not suggesting a full-time “world’s best boss” impersonation. Get ready to laugh, learn, and maybe even channel your inner Scott—because when it comes to leadership, the unexpected might just be the key to unlocking a new angle.
The article is divided into two parts: the first is my personal reflection based on my experience leading the design team at FlytBase and draws parallels with Michael Scott’s leadership style. The second is more analytical, focusing more on specific lessons learned from Michael Scott’s leadership. This article is one of the longest ones I have written so far. Short on time? Skip to the TL/DR at the end! Wait, is this too big for you?
Introduction to Unorthodox Leadership
I worked at FlytBase for about 4 years. FlytBase is a Silicon Valley startup in the drone automation industry building a software platform. Things were pretty interesting because this industry is what I like to call ‘Generation One Commercial Drone Automation Software’.
I led the team there for about three years. Leading a team behind a globally used product early in my career was an invaluable learning experience. The transition from being a junior to being a leader made me realise very soon that I was now responsible for people and their designs. This was my first time leading. So far, in my career, I have never led anything. Always been a part of a team. It took me a while to realize this, but I fell in love with the leadership part of the job.
I admire Michael and his leadership style in some ways. Michael’s tantrums were often ridiculous, but his infectious enthusiasm for Dunder Mifflin was undeniable. I channel that same passion for my own work and team, sharing experiences with the excitement of a kid on Christmas morning. It’s about creating a buzz—a shared drive that keeps everyone pulling towards the same goal. Michael’s heart, for all its misguided attempts, often landed in the right place. I, too, believe in putting people first. My door (or Slack) is always open. It’s a safe space for team members to share challenges and anxieties, knowing they’ll be met with an understanding ear and a willingness to go the extra mile. Trust thrives in such an environment. Let’s get straight to the lessons I learned and how they draw parallels with Michael.
- Humans are emotional beings
Let me begin with one of the biggest misconceptions I had about leadership. I used to believe that you can learn ‘only’ by following someone’s path or approach. Sure, you pick up tricks, but true leadership demands more. It’s about crafting your own path, where your thoughts, decisions, and emotions paint a unique leadership aura. Following in someone else’s footsteps won’t find your inner glow. As leaders, we need to embrace individuality and lead with authenticity.
For example, for me, I feel I am too empathetic and emotional. And that is what makes me feel things for my team. I prioritize feelings first, then apply logic to the situation. It makes me think differently. However, at the end of the day, it is logic that prevails at work. Partly because I believe logic is what makes people come to a conclusion. Not emotion. Emotion cannot be generalised across decisions just like logic can. Emotional aspects are too deep and difficult to generalize for everyone. Had they been similar, all humans would take emotion into the picture more at work than logic.
M:So you’ve come to the master for guidance, Jim? Is this what you’re saying, grasshopper?
J:Actually you called me in here.
M:Okay.
Showcase emotions? The man shows vulnerability. His own emotional stumbles make him approachable and relatable. He shows it’s okay to be human, encouraging open communication and fostering a safe space for his team to express themselves. From standing up for Pam’s art to forgiving Dwight’s betrayal, he also turns empathy into action by doing something about problems.
It starts with the people. Logic has its place, but Michael understood that connection is key. He greeted every new face, breaking down barriers and fostering collaboration. Michael’s quirky methods prove that sometimes a leader’s biggest strength lies in embracing their emotional side.
2. The team's heart beat outshines the pay & deadlines
I’ve made countless personal sacrifices to prioritize work, whether it’s burning the midnight oil, putting in overtime on weekends, or being on call until 3 or 4 am to support my team even when I don’t have any immediate tasks. It’s about going the extra mile for my team, allowing them to breathe easy, work effectively, connect with me, and deliver their best. As a leader, I believe this is paramount. If my team sacrifices their sleep, I stand by them through the night—no exceptions. That’s a leadership skill I hold in high regard.
The man, too, stood tall for his team. How did he show this? The genius at negotiation. Remember when he sold the Michael Scott Paper Company to Dunder Mifflin? He saw through all the numbers, identified the opponent’s real weaknesses, and played his cards masterfully. He knows what he is worth. What his employees are worth. He has crystal clarity on how to deliver that message across the table. A leader understands that the true currency of a team is it’s members. A leader drives the passion, motivates them when they need it the most, & recognizes their value.
M:Business isn’t about money to me, David. If tomorrow my company goes under, I will just start another paper company and another and another. I don’t have a shortage of company names.
D:Michael-
M:That’s one of ‘em.
3. Get ‘high’ on morale
One-on-one meetings were my window into understanding team anxieties and challenges. Instead of reactive one-on-ones, I built a proactive feedback loop. Open communication was very important. I used 5-minute or sometimes even hour-long check-ins and scheduled meetings to actively seek out anxieties and challenges being faced by a person in the team. By encouraging questions and introspection, I created a safe space for open dialogue. This allowed me to truly listen to concerns, identify issues collaboratively, and explain my reasoning while seeking their perspective. This mutual understanding often led to actionable solutions. I also embraced both direct and subtle feedback on my leadership and work style, using it to refine my approach and address any gaps.
One challenging moment I faced in my organization involved a proposed brand logo change that we, as a design team, felt wasn’t aligned with our vision. I carefully considered management’s perspective and then approached the CEO with our concerns and alternative proposals. He appreciated my initiative and trusted us to explore further. We worked through the night and presented several revised options, but couldn’t come up with something new that everyone liked. But ultimately, I convinced them to stick with the existing logo. This experience taught me the importance of both advocating for your team’s vision and navigating sensitive situations with respect and clear communication.
Low morale often stems from unaddressed problems. My solution? Get them in a room, hear them out, & solve problems together. No issue is too big or too small. Resolving it, whether within minutes or a day, was the priority. Seeking guidance from leadership further ensured we tackled challenges effectively. When we were struggling, I actively investigated what other teams were doing well. Understanding their successes and implementing relevant practices became a key way to increase the team’s motivation and ensure everyone felt on the same positive trajectory.
Imagine this: You read the news that your company is going bankrupt. Your boss tells you to calm down and focus on work. Now, will you be able to focus on work? You will probably do the opposite.
M: I. DECLARE. BANKRUPTCY.
Michael made everyone play a game of murder mystery when everyone heard that the company might actually go bankrupt. He gave them a distraction when there was no news on anything from the corporate office. I don't know if this was the right thing to do or not. But I do know this: His heart was in the right place. Sometimes all you need is a kit-kat break.
M: Games have power to distract people from stressful situations. ‘Battleship’ got me trough my parents divorce.
4. The cost of bottled-up stress and the power of open communication
Michael doesn't handle stress well. Michael’s impulsive decisions under pressure caused project delays and created a tense atmosphere. My own past tendency towards denial showed me the importance of open communication to navigate challenges. So, why not think one step ahead, like a construction worker building stairs?
When design missteps triggered a forced training session from the then-leadership team when I had just joined the office, instead of addressing the root cause, I felt disrespected and silenced. This experience ignited my passion for advocating for myself and others, ensuring everyone’s voice matters when I lead. I had paid the cost. I knew that day that if I were to lead the team, I would be vocal and put out my opinions about everything I felt. And I did.
My experience, though born from discomfort, shaped a defining principle: As a leader, I strive to foster a culture where respect is the foundation and open communication bridges individual contributions to collective growth. My voice will no longer be silent, but a force for positive change, inspiring open dialogue and a space where everyone feels empowered to keep their voice and contribute.
While voicing out your opinions is important, it is also important to curate them well. Leaders need to deliver a message that is crystal clear. Without any vagueness. You need perfect words so that the person opposite will also keep the conversation on track. As they say, you need to ask the right questions to get the right answers. The crisper the question, the crisper the answer. More meaningful conversations. Saves time & money. Avoid Michael’s “vague-ness,” as he calls it. Clear communication is key.
5. Dealing with situations and the culture of respect
A team member of my team and I never had the same views on a lot of things, but our passion for design was common. One day, our office had a town hall meeting. Towards the end of the meeting, I was asked to present an award to the best performer in the team in recent times. I instantly knew who it was, and I took his name. I think he and the team were in shock. I could feel this with the reaction they gave. Even though our views never matched, I knew that we had to recognize the best work. I knew his contributions outmatched those of anyone else on the team. Sometimes you can't make decisions just because of the emotions you feel. Doing the right thing requires logic. A leader acknowledges, appreciates excellence, and recognizes their team member's work and efforts while disregarding the differences in views and perspectives.
Here’s an honest truth: Some people go behind your back. It happened to me. Happened with Michael. I did not take it well. Looking back, I know I could have handled that situation much better. This was a big lesson for me. But I like the way Michael handled that situation. He gave Dwight enough time to explain and ended up addressing the issue. Finally, he had to be the one with the bigger heart and choose to forgive him. A leader understands the situation and always addresses it. This reduces what Gen-Z likes to call “toxicity” at the workplace. Acknowledgments fuel motivation and loyalty.
M:I’ll never trust you again Dwight. How can I trust you?
*Dwight, laying on the floor*
D:You can’t. But I promise I’ll never betray you again. What can I do?
*Michael shighs*
M: You can get up…and hug it out, b****!
It’s crucial to maintain respect for everyone in the office. Remember the Michael and Stanely incident? When Michael asked Stanley “why he didn’t respect him?” Stanley said, “I don’t respect you. I have known you long enough, and every day you do something that I would do exactly opposite if I were you.” To which Michael said, “Alright, I get it. But you can’t talk to me that way in this office. I am your boss. I can’t allow that.” Here’s the harsh truth: Not everyone will agree with your style. A leader understands that respecting boundaries and different perspectives fosters a healthy environment. Sometimes you can't be the leader; you have to be the boss. Though times require tough decisions.
Leadership lessons expressed by Michael Scott
Throughout the show, Michael Scott proves ‘human connection’ drives results by making his branch the most profitable. He does 'something'. Let’s have a look at that ‘something’. What qualities does he possess? What actions does he take?
1. It starts with the people
M: What is the most important thing for a company? Is it the cashflow? Is it the inventory? No. It’s the people.
A people’s person. Although Michael’s position as regional manager gives him authority over making decisions, he prefers to prioritize strengthening his relationship with his employees. And you can see how much he values each team member when he was the only one who ended up at Pam’s art show. Or when the company is facing issues, he is the one who takes the lead to calm down the anger in a hall full of thousands of employees. He said that he’s going to work with other leaders and come up with a 45-day plan to save the company. Why does he say this? To gain attention? Yes. But that’s not his true motive at that moment. The motive is to give hope. He values relationships with people more than he values a company he has been working for for more than 20 years. He knows hope is a thing. He knows that relationships matter. As a leader, he is optimistic, prioritizes personal connection with people, and shows genuine care.
Remember Michael’s late-night pizza runs or his awkward birthday gestures? They were misguided, sure, but they came from a genuine desire to see his team happy.
Lessons:
- Show up for your team. Build strong relationships with your team and value their well-being above everything else. Be a part of their personal milestones and celebrations. Show appreciation.
- Offer hope and optimism. Believe in positive outcomes and inspire hope in your team even during challenging times to instill confidence.
- Small gestures create a big impact. Even simple acts of kindness can demonstrate genuine care and build personal connections.
2. The Power of Unscripted Moments
Michael thinks quickly on his feet. He could be well-aligned as a good improv. Sometimes it may be a little too much. Leadership is like jazz. It’s about knowing when to stick to the script and when to embrace the improvised solo.
And I knew exactly what to do. But in a much more real sense, I had no idea what to do.
Remember Michael’s accidental genius moments? That’s the power of creative thinking, even when it comes in sideways. Sometimes, the silliest suggestion can spark the next big innovation.
I mean, I don’t see why other people think Michael is not that good of a salesman. He literally sold Mr.Buttlika a million dollars of paper just from the sound of his voice alone.
Lessons:
- Think beyond the script. Be creative, & encourage collective creativity through collaboration. Embrace improvisational thinking & explore unconventional solutions in order to adapt to unexpected situations.
- Lead with passion. Spark excitement and motivate your team with your own energy.
- Stay confident. Trust your instincts and take calculated risks, even when unsure.
3. It’s a part of your job
The TV show starts with Dunder Mifflin undergoing downsizing. He tried to avoid the situation but eventually had to let go of some team members. Sometimes you’ve got to do what you have to do. You have to let go of some people. It’s a part of your job.
M: Would I rather be a good boss and sit at my desk all day, or a great boss and be out there with them?
When corporate decides to cancel the annual Dundie awards, a Scranton tradition held dear by the employees, Michael takes matters into his own hands. He organizes a secret ceremony in the warehouse, defying corporate expectations and risking his job to ensure his employees have their special moment. While chaotic and hilarious, it shows Michael’s genuine care for their happiness and sense of belonging. As leaders, it’s important to advocate. The man is great at problem solving. Whenever there is any conflict, Michael calls and forces everyone to collaboratively talk about the situation and resolve conflicts.
Lessons:
- Take the initiative. Don’t wait for others to raise their hands. Go beyond what is expected to create special moments and traditions for your team.
- Facilitate conflict resolution. Bring people together to openly discuss and address issues.
- Show your human side. Express genuine interest and support for your team. Stand up for your team and their needs, even against higher powers.
Well, don’t
At times (well, mostly), how do I put it? Um, Michael is just plain stupid. From micromanagement by overstepping boundries in his colleagues lives to poor decision-making by declaring bankruptcy and not filling out reports. He creates the total contrast. Is that bad? Of couse! You can’t even think of doing something like he did; otherwise, your Human Resources Department will specifically call you out to hear what ‘joke’ you made.
M: My philosophy is basically this. Don’t ever, for any reason, do anything to anyone for any reason ever, no matter what, no matter where, or who, or who you are with, or where you are going, or where you’ve been… ever, for any reason whatsoever.
Sometimes, I just start a sentence, and I don't even know where it’s going. I just hope to find it along the way.
The Takeaway (TL/DR)
Take risks, innovate, and explore on your own. Michael’s style resonates specifically with ‘The Office’ TV show. Blindly follow him, and you will most definitely end up creating a Jenga tower instead of a building. Learn from his missteps and embrace his heart. Find your own leadership jam. Find the Michael Scott symphony that ignites your team. Without setting the office on fire (figuratively, of course).
Introduction to Unorthodox Leadership
- Humans are emotional beings. Embrace and show vulnerability. Connection with your team is key. Understand that sometimes a leader’s biggest strength lies in embracing their emotional side.
- The team’s heartbeat outshines the pay and deadlines. A leader understands that the true currency of a team is it’s members. A leader drives the passion, motivates them when they need it the most, & recognizes their value.
- Get ‘high’ on morale. A leader addesses all challenges, even the one’s underling. They address them by showing open communication and boosting the team’s morale when they need it the most.
- The cost of bottled-up stress and the power of open communication. Understand the importance of open communication. A leader strives to foster a culture where respect is the foundation and open communication bridges individual contributions to collective growth. A leader should strive for positive change, inspiring open dialogue and a space where everyone feels empowered to keep their voice and contribute. Clear communication is key.
- Dealing with situations and the culture of respect. A leader acknowledges, appreciates excellence, and recognizes their team member’s work and efforts while disregarding the differences in views and perspectives. Acknowledgments fuel motivation and loyalty. A leader understands that respecting boundaries and different perspectives fosters a healthy environment. Sometimes you can’t be the leader; you have to be the boss. Though times require tough decisions.
Leadership lessons expressed by Michael Scott
It starts with the people.
- Show up for your team. Build strong relationships with your team and value their well-being above everything else. Be a part of their personal milestones and celebrations. Show appreciation.
- Offer hope and optimism. Believe in positive outcomes and inspire hope in your team even during challenging times to instill confidence.
- Small gestures create a big impact. Even simple acts of kindness can demonstrate genuine care and build personal connections.
The Power of Unscripted Moments
- Think beyond the script. Be creative, & encourage collective creativity through collaboration. Embrace improvisational thinking & explore unconventional solutions in order to adapt to unexpected situations.
- Lead with passion. Spark excitement and motivate your team with your own energy.
- Stay confident. Trust your instincts and take calculated risks, even when unsure.
It’s a part of your job
- Take the initiative. Don’t wait for others to raise their hands. Go beyond what is expected to create special moments and traditions for your team.
- Facilitate conflict resolution. Bring people together to openly discuss and address issues.
- Show your human side. Express genuine interest and support for your team. Stand up for your team and their needs, even against higher powers.
I’d like to end by asking you to think about your leadership style and question it. Embracing the unorthodox is not that easy. It needs to be well planned, experimented with, and tested. But the thought of adapting to some uncommon methods in your leadership style is interesting.
Wow, stuck around for so long? Damn. Thanks.
In startups, great leadership thrives in the space between order and chaos. I’ve written an article, “The Essence of Order in a Chaotic Startup Design World”. Dive in if you’re curious!
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I would love to know your thoughts on this article. What is your leadership style? What are your learnings? Drop a comment below!
Until next time!
-S :)
References:
- Chrecter Analysis 1: https://characters.fandom.com/wiki/Michael_Scott
- Charecter Analysis 2: https://medium.com/@claynorris/michael-scott-leadership-analysis-bd36ec42f03f
- Quotes Source 1: https://www.businessnewsdaily.com/7977-the-office-michael-scott-quotes.html
- Quotes Source 2: https://www.leadershipgeeks.com/leadership-quotes-michael-scott/
- Images and GIFs: https://www.google.com/ (and edited on Photoshop)
