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Leading by Example: 20 Inspirational Leadership Stories in Startups

From implementing mental health initiatives to inspiring through dedicated leadership, 20 startup leaders, including founders and CEOs, share their personal stories of leading by example.

These narratives, spanning 20 distinct insights, reveal the profound influence such leadership has on shaping team dynamics and organizational culture. Discover how these trailblazers foster innovation and resilience within their startups, setting a powerful precedent for their teams.

  • Implementing Mental Health Initiatives
  • Embracing Vulnerability as Strength
  • Participating in Employee Training
  • Supporting Employee Autonomy
  • Promoting Work-Life Balance
  • Modeling Conflict Resolution
  • Fostering a Learning Culture
  • Encouraging Innovative Problem-Solving
  • Focusing on Human Impact
  • Empowering Employees to Lead
  • Leading Remote Communication
  • Demonstrating Over Dictating
  • Upholding Resilience in Setbacks
  • Prioritizing Team Safety and Growth
  • Practicing Financial Transparency
  • Setting High Personal Standards
  • Keeping Commitments to Build Trust
  • Handling Difficult Customers with Grace
  • Celebrating Team Achievements
  • Inspiring Through Dedicated Leadership

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Implementing Mental Health Initiatives

I believe in mental health, especially after COVID. I implemented wellness programs for my fellow teammates and employees so that we could help each other. 

One practice that makes me very happy is giving mental health days off. We all have times when we feel low, have anxiety, fatigue, or don’t feel like doing anything. Giving mental health days off, where an employee can take one day of leave per month without any questions asked, encourages everyone to talk about their health without hiding anything, including myself. 

As the founder of a yoga organization, I think it’s crucial to pay as much attention to my employees as we pay attention to our customers. I’ve observed my team supporting each other and creating a safe environment for each other. This positivity in the workspace influences everyone.

Jean Christophe Gabler, Founder, Yogi Times

Embracing Vulnerability as Strength

As a leader, I am not afraid to show my vulnerabilities. The notion that leaders can’t show their weaknesses is entirely wrong. Both strength and weakness are integral parts of the human personality. 

Without weakness, one can’t enhance strength. I want my character to feel authentic and welcoming to my employees. I want to show them that even leaders have weaknesses and that they don’t shy away from admitting their mistakes. They are willing to learn, grow, and become better professionals. 

This approach has worked as an example for my employees. Now, they don’t hide away from admitting their errors; they always take accountability for them. Moreover, they seek me, managers, or colleagues whenever they need help.

Marcus Phillips, Founder, Mortgages

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Participating in Employee Training

When there are workshops or training programs in my office, I attend with my employees. Initially, many employees were surprised by that. Some even asked me the reason. I told them a leader or an entrepreneur should never stop learning. 

If I stop learning, it will stem my growth process, harming the company’s future. And I don’t think of myself as superior compared to them. Therefore, I have no qualms about enhancing my skills alongside them. I believe that incident boosted my image in front of my employees. They began to participate eagerly in the workshops without any complaints. It also paved the way for a learning-centered workplace culture in our company.

Doug Van Soest, Co-Founder, SoCal Home Buyers

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Supporting Employee Autonomy

I prioritize helping my employees. It doesn’t mean I interfere with their work or make them follow my suggestions. I only help them when they need it or ask for it. My employees have the freedom to decide how they want to work. If they struggle, they can always come to me. If leaders force solutions, it can disrupt employees’ work and affect their self-esteem. 

Also, I believe I can provide help not only regarding work to my employees. I encourage my employees to come to me if they need advice on aspects other than work. My employees welcome this way of helping, and they do the same with their colleagues.

Brad Russell, SEO Expert and Founder, Digital Hitmen

 Promoting Work-Life Balance

A leader’s failure can often be seen in their inability to prevent employee burnout. It is essential that leaders foster a healthy and balanced work-life for their team. I promote a well-balanced work-life in my workplace and take a genuine interest in the well-being of my employees. 

Before assigning tasks, I ensure they are comfortable and have the necessary resources. I avoid putting work-related pressure on them and enforce boundaries between work and personal life, insisting that no one should be contacted for work during holidays or vacations. 

Additionally, I organize company retreats to help employees relax. This approach has positively impacted my team, making them more upbeat and engaged.

 Tom Vota, Marketing Director, Gotomyerp


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Modeling Conflict Resolution

It’s common to have occasional workplace conflicts in any company. Employees can handle them efficiently if the leaders do so. Leaders should address disputes in such a way that it sets a fine example for the employees. In this way, they will be able to handle conflicts on their own without needing a mediator. I could make this possible in my company through my leadership. 

 Whenever I face a workplace conflict, I listen to the issue with concentration. Afterward, I think of a solution to end the conflict instantly. I also ask for the views of the involved people regarding the solution. I never let a workplace conflict persist for a long time because I know it can affect workplace productivity. My employees also follow the same approach.

 Wayne Mills, Head of Operations UK and Ireland, Seven Seas Worldwide

 Fostering a Learning Culture

At our core, we value lifelong learning, recognizing that a willingness to try to learn is integral to our future success. To embody this, we’ve integrated “lessons learned” into our weekly and monthly planning, focusing on broader, introspective insights for personal and professional growth. This practice extends to our All Hands meeting, where employees, including new hires, openly share their weekly lessons. 

 This commitment to transparency builds a culture of accountability and honesty, with everyone, including leadership, owning up to mistakes and viewing them as opportunities for company-wide growth. In essence, we acknowledge that perfection is not the goal; mistakes happen, but by owning them, we prevent recurrence and foster a culture of continuous improvement.

 Lynn Morton, VP of Marketing, Novel Capital


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Encouraging Innovative Problem-Solving

A critical crossroads emerged when market dynamics shifted, and we had to change our strategy. Rather than a conventional approach, I introduced “Blank Canvas Day.” The entire team, including myself, took a day off from routine tasks to brainstorm without constraints. 

 My contribution wasn’t a directive but an unconventional idea inspired by my diverse experiences, and I participated just like everyone else. This unorthodox thinking day led to important insights.

 By embracing unconventional solutions, I demonstrated that critical thinking often requires stepping outside established norms. This approach sparked a culture where tackling challenges with a fresh perspective was not only encouraged but celebrated.

 Brandon Green, Founder, Let’s Go Brandon Green

 Focusing on Human Impact

I keep the human-impact-driven reasons our business needs to succeed at the forefront of my actions, and this helps keep our company culture focused on what matters. Of course, we all have metrics we need to be mindful of, but if we lose sight of the stories and experiences that led to the “aha” moment of the business idea, we simply won’t succeed.

 A team goal of hitting a sales target is sterile and lacks impact, whereas a focus on the impact on our customers’ daily lives keeps the team engaged and invested.

 Dan Freeman, CEO, MD Clarity

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Empowering Employees to Lead

As the figurehead of my company, the best strategy I have ever implemented with my team was to show my employees how it’s done while also letting them lead. As a startup, it is paramount that you stick to a strict set of rules, as you still can’t let it hit the fan. However, empowering your pioneer employees and letting them lead when their ideas could propel the company forward is also important.

 This display of faith has influenced my team for the better, as they know they are valued under my watch and that their voices are actually heard. Always remember that everyone has something of value that they can add to the table. It is up to us, leaders, to show them that table.

 Jason Boyd, Director, Evolve SEO Agency

 Leading Remote Communication

As a remote team leader, one of the best ways I lead by example in my startup is by sharing and communicating well.

 Communication is extremely important in a remote environment because the typical and casual work conversation that would happen over the desks suddenly has to be thought about and purposefully brought up in group chats and emails. I know that for many, this can feel like overkill at the start because how much you are saying in a group chat feels quite unnatural.

 This is why it is such an important thing for me to lead on. My team needs to see that the communication level is important to me so that they feel less awkward doing it themselves. After a while, it becomes much more natural, and the remote comms are just as strong as the in-office ones.

 Brett Downes, Founder, Haro Helpers


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Demonstrating Over Dictating

I only lead by example in this new company. Showing works infinitely better than telling. It’s how we all learn. Everyone is brilliant, but not everyone is articulate. Words fail us frequently. 

 Yesterday, I explained our packing and shipping process to a new employee. They nodded, smiled, and said they understood, but we both knew that they didn’t. I went through the process from start to finish one time with them, and they were off to the races. Showing is infinitely more valuable than telling.

 Kam Talebi, CEO of Gigli, Gigli

 Upholding Resilience in Setbacks

In the startup world, setbacks are inevitable. I handle these setbacks with resilience and a problem-solving mindset. By showing that setbacks are opportunities for growth rather than failures, I’ve encouraged our team to approach challenges with a similar mindset, fostering a resilient and solution-oriented culture.

 Tim White, Founder, milepro

 Prioritizing Team Safety and Growth

My first priority has always been the safety of my entire team. Construction sites are dangerous, even with the necessary safety precautions, so make sure nobody is slacking off. 

 One of the leading causes of injuries is misusing equipment. Hold regular training sessions and offer ways for your employees to learn. Additionally, create opportunities for them to get certifications to operate heavy machinery. Preventing accidents is important, but injuries are inevitable in this business.

 If someone gets hurt, you should try to help out with the medical bills or insurance. Be available and approachable for anything they might need. Taking care of their health and helping them build their careers through training will make you the best leader you can be.

 Michael Branover, Business Development Manager, Branover Contractors

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Practicing Financial Transparency

Our business revolves around finance, so it’s really important that our team embodies financial openness both in how we operate and how we educate others. That’s why I openly share financial information with my team about our operations, financial health, and biggest goals. Questions are welcomed with open arms because they help us all become stronger.

 That transparency doesn’t simply help to take the stigma away from talking about money. It also gives our team peace of mind that they know exactly what’s happening at any given time. When those topics aren’t addressed amid rising inflation, uncertain economies, and other industry-wide challenges, many employees tend to assume the worst or worry about their company’s stability.

 Gillian Dewar, Chief Financial Officer, Crediful

 Setting High Personal Standards

If you don’t want your squad to be average, don’t be mediocre yourself. Whatever you do will be seen and emulated, so begin by expecting greatness from yourself. Your team will notice and work hard to keep up. 

 In my view, the quickest approach to training a team is to lead by example. When you hold yourself to a high level, your team will do the same to achieve your approval. They will live up to our standards of excellence, integrity, and respect if you do the same for them. And when your team is made up of exceptional people, you can be certain of success.

 Adam Crossling, Marketing and New Business Director, Zenzero

Keeping Commitments to Build Trust

I have been more intentional about this recently. When I have something to deliver to a member of the team, I always give them a date and time by which I plan to do it. This forces me to be thoughtful about priorities and trade-offs, and also to work very hard to meet that date, thus improving trust with the employee. 

 Even with small, insignificant items, I am a person of my word. This has had some positive effects downstream, as it’s what I expect from the rest of the team when interacting with me, each other, or customers.

 Trevor Ewen, COO, QBench

 Handling Difficult Customers with Grace

I never ask my team to do anything I wouldn’t do myself. One particularly good example of this was with our customer service reps. I always stress to them that the customer is always right, and no matter how god-awful they can be, to stay positive, empathetic, and flexible. 

 One day, we had a student’s mother call in about the tutoring service her son was getting, and she was irate. She asked to speak to me personally, which I normally never do, but I agreed. I got on the line with her on speakerphone in front of my team and practiced exactly what I preached to them. This woman was an absolute witch and the kind of person I despise personally, but despite her toxic attitude, I stayed positive, kind, and respectful. 

 I think that really resonated with the team because no matter how terrible someone is, if the boss can handle it with grace like that, they should be able to as well.

 John Ross, CEO, Test Prep Insight


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Celebrating Team Achievements

Remote working is great, but one of its drawbacks is the lack of communication and positive feedback, which leads to decreased emotional connectivity in your team.

 I wanted to combat this issue by fostering a culture where our team members congratulate each other regularly for their achievements.

 I did this by creating different Slack (messaging software) channels dedicated to certain business operations, one for link-building and outreach, for example.

 I then told everyone in the channel to shout about it whenever they received a link or published an article. Then, I made sure to congratulate that person and sing their praises.

 Everybody joins in congratulating each other, and it’s created such a positive environment.

 It’s a small thing but has worked wonders to boost our team morale. Since doing this, our team is much more eager to build links, and we’ve actually increased our traffic by over 300% year-on-year!

 Will Rice, SEO and Marketing Manager, MeasureMinds Group

 Inspiring Through Dedicated Leadership

A few years ago, we were working on a particularly complex case that required long hours and late nights at the office. I could see that my team was feeling drained and exhausted, and morale was slipping. That’s when I took action.

 To inspire my team and show them we were all in this together, I made a point of being the first one in the office each morning and the last one to leave at night. I checked in with everyone individually, asking them how they were feeling and if there was anything I could do to support them.

 By leading by example and showing my team that I was just as invested in the case as they were, we were able to boost morale and approach the work with renewed energy and commitment. It wasn’t long before my team followed suit, arriving earlier and staying later, all in an effort to ensure that we achieved the best possible outcome for our client.

 Tom Wagstaff, Law Firm Founder, Law Office of Tom Wagstaff Jr

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