From Microsoft to Middle School: Damon Fitzgerald’s Unlikely Pivot

In “From Microsoft to Middle School: Damon Fitzgerald’s Unlikely Pivot”, this episode of @SuccessYourOwnWay , Yifat Rogers and I sit down with Damon Fitzgerald, a former Microsoft sales executive who made a dramatic career pivot, leaving big tech behind to teach middle school social studies. Damon shares why he made the shift, what he learned from his students, and how his definition of success has evolved. From authenticity and leadership to personal fulfillment and redefining ambition, Damon’s story is honest, inspiring, and full of life lessons (with a few laughs along the way). Whether you’re considering a big life change or just want to hear what it’s like to go from selling tech to wrangling 8th graders, this one’s for you.

About the Guest

Damon’s most recent professional experience was as a middle school social studies teacher in Bloomington, MN. He retired from teaching in 2024 after spending 4 years in this profession.

Before making this pivot to become a teacher, Damon spent over 21 years at Microsoft, where he served in multiple customer-facing roles within the field sales organization. His final role there was leading a sales team covering Microsoft’s Higher Education and K12 customers in the Midwest. He also had roles leading Microsoft’s Enterprise Software business and the Core Infrastructure business, also in the Midwest. He began his career at Microsoft in 1998 as a channel sales manager and also served as a Commercial Account Executive. Throughout his tenure at Microsoft, he earned several awards for excellence.

Before joining Microsoft, Damon was a Senior Consultant at Connect Computer and served as a Senior Consultant with Accenture as a business analyst and developer.

Damon is a native Chicagoan and still has family residing in the Windy City. He lives with his wife Julie, and daughters Janna (21 yrs) and Alecia (17 yrs) in the southeast suburbs. Damon’s community involvement includes service on the Memorial Blood Center Advisory Board and the Osiris Organization board. He enjoys basketball, reading, and traveling with his family. He is a proud booster of the University of St. Thomas basketball team, where he played four years and earned a B.A. in Business.

Taking a Vacation is Important

Why Rest and Recharge Matter More Than Ever

Taking a vacation is important. Have you ever skipped taking one?  Felt like you couldn’t take one because things would fall apart at work, or that you’d be so far behind when you got back, it wasn’t worth it?  If so, you’re not alone.

I recently returned from a two-week vacation.  I think the last time I did that was for my wedding and honeymoon, which was nearly 15 years ago.  It got me thinking about how important vacations can be to reconnect with those you love (including yourself!), change up your environment, and remember who you are when you’re not in your routine (or dare I say, rut?).

For many, the concept of taking a vacation often feels like a luxury rather than a necessity. Yet, stepping away from the demands of work, routines, and everyday responsibilities is not merely indulgent—it is essential for maintaining physical health, promoting mental well-being, and enhancing overall productivity. A vacation is not just time off; it is an investment in yourself (and your family or friends) and your ability to function at your best.

Escaping the Grind: Why You Need A Break

The human body and mind are not built to operate under constant stress. Many people find themselves overwhelmed by deadlines, work pressures, and the relentless demands of daily life. This chronic stress can lead to burnout, anxiety, and a host of physical health issues, including high blood pressure, weakened immunity, and even heart disease.

Taking a vacation provides an opportunity to step back, recharge, and reset. Vacations reduce stress levels by removing you from the sources of your strain and allowing your body and mind to recover. Studies have shown that people who take regular vacations experience lower rates of depression, better cardiovascular health, and improved mental clarity.

Enhancing Productivity Through Rest

Contrary to the common belief that working endlessly boosts productivity, the truth is that breaks, including vacations, are critical for peak performance. After periods of intense focus and effort, the brain needs downtime to process information, solve problems creatively, and regain energy.

Vacations help restore this balance by giving you the chance to experience new environments, disconnect from work-related challenges, and engage in activities that inspire fresh perspectives. Upon returning to work post-vacation, employees often exhibit increased motivation, heightened creativity, and renewed vigor, leading to better results and a more optimistic outlook.

Cultivating Stronger Relationships

Vacations are not just about personal well-being; they also contribute to the health of your relationships. Time spent with family, friends, or loved ones allows you to deepen bonds, share experiences, and create lasting memories. Whether it’s a simple weekend getaway or a grand overseas adventure, the shared moments enrich your connections and bring joy to all involved.

In the absence of work-related distractions, vacations provide a platform for meaningful conversations and quality time, strengthening the fabric of relationships that might otherwise be strained by daily pressures.

Exploring the World and Yourself

Traveling to new destinations during vacation is one of the most enriching experiences one can have. It exposes you to diverse cultures, perspectives, and ideas, broadening your understanding of the world. These discoveries not only foster personal growth but spark inspiration that fuels your creativity and decision-making in professional and personal realms.

Vacations provide a rare chance to reconnect with yourself. Away from the noise of daily life, you can reflect on your goals, values, and aspirations. Whether you spend time wandering through historical landmarks or relaxing on a serene beach, the act of stepping away allows you to rediscover your purpose and priorities.

Overcoming Barriers to Taking a Vacation

Despite the clear benefits, many people, especially leaders, hesitate to take vacations due to workload pressures (including the lack of delegation or trust), fear of falling behind, and even putting your employment at risk. It is crucial to recognize that these obstacles can often be mitigated with proper planning and communication. Strong leaders understand the value of rested, satisfied employees and are more accommodating of vacation requests.  And they also model this behavior and provide the added benefit of empowerment for their team members while they are away.

Making Vacation a Priority

To truly reap the benefits of taking a vacation, it is necessary to prioritize it in your life. View it as an essential element of your health and happiness, not an optional luxury. Schedule vacations regularly and treat them as sacred time, free from work emails, calls, and distractions. Encourage those around you—family, friends, colleagues—to do the same. Advocate for a work culture that values breaks and understands their role in fostering creativity, mental health, and long-term productivity.

Time to Thrive

Taking a vacation is important and is much more than an escape; it is a key component of living well. Whether you choose to unwind at home, explore a bustling city, or retreat to a mountain hideaway, the act of giving yourself permission to pause is transformative. Vacations fuel your body, mind, and soul, allowing you to return to your life recharged, inspired, and ready to tackle challenges with renewed focus.

So, the next time you consider skipping a vacation, think again. Your well-being, relationships, and even your career might depend on it. Make the time to rest, explore, and enjoy—because thriving is always better than simply surviving. Reach out if you want to talk more about strategies that allow you to prepare to take a break without adding stress to your already busy life.

Effective Management of a Global Team

Effective management of a global team is a critical skill these days, and it’s not easy. Have you been a part of one?  Led one before?  If so you know that managing a global team (or even a remote one) presents unique challenges, but it also offers numerous advantages for businesses.

Benefits of a Global Team
Access to a Diverse Talent Pool 🌍

Hiring globally allows companies to tap into a broader range of skills and expertise. Instead of being limited to local talent, businesses can recruit the best professionals from different regions. The benefits are access to specialized skills that may not be available locally, increased innovation through diverse perspectives, and the ability to scale operations with a larger workforce.

Enhanced Creativity and Innovation 💡

A global team brings together individuals from different cultural backgrounds, experiences, and viewpoints. This diversity fosters creativity and leads to innovative solutions.  Some of those benefits are fresh ideas and unique problem-solving approaches, increased adaptability to changing market trends, and more effective brainstorming and collaboration.

Expanded Market Reach 🌎

Having employees in different regions helps businesses understand local markets, consumer behaviors, and cultural preferences. This insight allows companies to tailor their products and services more effectively.  Benefits are better customer engagement in different regions, increased brand presence and credibility worldwide, and faster expansion into new markets.

Around-the-Clock Productivity

With employees working in different time zones, businesses can operate continuously. This ensures faster project completion and improved customer service.  Those benefits are 24/7 business operations without downtime, faster response times for global customers, and increased efficiency in project management.

Cost Savings and Operational Efficiency 💰

Hiring globally can reduce costs by leveraging talent in regions with lower labor expenses. Additionally, remote work eliminates expenses related to office space and infrastructure.  The benefits here are lower operational costs compared to maintaining physical offices, the ability to hire top talent at competitive salaries, and reduced overhead expenses for office maintenance.

Greater Cultural Awareness and Inclusion 🤝

A global team fosters cultural awareness, helping businesses build stronger relationships with international clients and partners.  The benefits are improved cross-cultural communication skills, stronger relationships with global stakeholders, and enhanced company reputation for diversity and inclusion.

Increased Employee Satisfaction and Retention 😊

Offering remote work opportunities and flexible schedules can improve employee satisfaction, leading to higher retention rates. That creates work-life balance for employees in different locations, increases job satisfaction and engagement, and lowers turnover rates due to flexible work arrangements.

Overcoming Leadership Challenges
Establish Clear Communication Channels

Effective communication is the foundation of managing a global team. Without face-to-face interactions, misunderstandings can arise, leading to inefficiencies. Use collaboration tools like Slack, Microsoft Teams, or Zoom for real-time discussions, set expectations for response times, especially across different time zones, encourage video calls to build stronger connections and reduce misinterpretations, and provide written summaries of meetings to ensure clarity.

Navigate Time Zone Differences

One of the biggest challenges in global teams is coordinating across multiple time zones. Scheduling meetings that accommodate everyone can be difficult. Rotate meeting times to ensure fairness for all team members, use scheduling tools like World Time Buddy or Google Calendar to find overlapping working hours, record important meetings for those who cannot attend live, and encourage asynchronous communication to reduce dependency on real-time interactions.

Foster Cultural Awareness and Inclusion

Cultural diversity is a strength, but it requires sensitivity and understanding. Different work styles, communication norms, and holidays can impact collaboration. Educate team members on cultural differences through training or discussions, celebrate global holidays and recognize cultural traditions, encourage open dialogue about work preferences and expectations, avoid assumptions—ask questions to understand different perspectives.

Set Clear Goals and Expectations

Without shared office space, global teams need well-defined goals to stay aligned. Ambiguity can lead to confusion and inefficiency. Use SMART (Specific, Measurable, Achievable, Relevant, Time-bound) goals, clearly define roles and responsibilities for each team member, regularly review progress through virtual check-ins, and provide detailed documentation for projects to ensure clarity.

Build Trust and Team Cohesion

Remote teams can sometimes feel disconnected. Building trust and fostering relationships is essential for a strong global team. Schedule virtual team-building activities, such as online games or informal chats, encourage cross-team collaboration on projects, recognize achievements and celebrate milestones, and create an open-door policy where employees feel comfortable sharing concerns.

Adapt Leadership Style for Remote Work

Leading a global team requires flexibility and adaptability. Traditional management styles may not work in a remote setting. Focus on outcomes rather than micromanaging daily tasks, encourage autonomy and empower employees to make decisions, provide regular feedback and support to keep employees engaged, and be empathetic and understanding of personal and cultural differences.

Getting the Most From Your Global Team

Effective management of a global team requires strong communication, cultural awareness, and the right tools and technology. By fostering inclusivity, setting clear expectations, and adapting leadership styles, leaders can create a productive and engaged workforce across borders. With the right approach, global teams can thrive and drive success in today’s interconnected world. And coaches can help!  Reach out if you want to learn more about how coaches can support you in delivering effective management of a global team.

Transitioning from Peer to Manager

Transitioning from peer to a manager is one of the most difficult career transitions I have experienced. It requires a whole new mindset, refined communication skills, and a strategic approach to leadership. And in the words of Marshall Goldsmith, “What Got You Here Won’t Get You There”. There are also significant benefits to making the transition from peer to manager.

Benefits of Transitioning from Peer to Manager
  • Continuity and Familiarity – Since you were previously a peer, your team benefits from having a leader who understands their challenges, strengths, and dynamics.
  • Stronger Communication and Trust –Your existing relationships with team members can foster open communication and trust, making collaboration smoother.
  • Improved Team Morale – A manager who has firsthand experience with the team’s work can advocate for their needs, leading to better support and motivation.
  • Clearer Career Growth Paths – Your promotion sets an example for others, showing that career advancement is possible within the organization.
  • More Effective Leadership – Since you already know the team’s workflow and challenges, you can implement improvements that directly benefit productivity and efficiency.
Overcoming Challenges

For those of you going through the transition from peer to manager, you know that what makes this transition so challenging is that you go from working alongside colleagues as equals to leading them, making decisions, and holding them accountable. This can test both your leadership skills and your emotional intelligence. Here are some of the most common obstacles and how to navigate them effectively:

Embrace Your New Role with Confidence

One of the biggest hurdles in transitioning to management is overcoming self-doubt or imposter syndrome. You may feel awkward leading former peers but remember—you were chosen for this role because of your skills, experience, and leadership potential. Own your new position with confidence while remaining approachable and supportive. Acknowledge the transition openly with your team. Let them know you’re excited about the role and committed to their success.

Set Clear Expectations

As a peer, you may have shared casual conversations and informal work habits with colleagues. As a manager, you need to establish clear expectations regarding performance, accountability, and professionalism.  You must define roles and responsibilities clearly, communicate goals and objectives early on, and ensure fairness and consistency in decision-making.

Shift Your Mindset from “Friend” to “Leader”

While maintaining positive relationships is important, your primary responsibility is now to lead. This means making tough decisions, addressing conflicts, and sometimes delivering difficult feedback. Be friendly but professional—avoid favoritism, set boundaries to maintain respect and authority, and focus on mentorship rather than personal friendships.

Develop Strong Communication Skills

Effective communication is key to earning trust and respect. You must be able to articulate expectations, provide constructive feedback, and listen to concerns. Hold regular one-on-one meetings with team members, be transparent about changes and decisions, and encourage open dialogue and feedback.

Learn to Delegate

Many new managers struggle with delegation, often feeling they need to do everything themselves. However, effective leaders empower their teams by assigning tasks based on strengths and skills. Trust your team’s abilities—avoid micromanaging, assign tasks strategically to develop employees’ skills, provide guidance but allow autonomy.

Handle Conflicts Professionally

As a peer, you may have avoided workplace conflicts. As a manager, addressing issues is part of your responsibility. Whether it’s performance concerns or interpersonal disputes, approach conflicts with fairness and professionalism. Listen to all perspectives before making decisions, address issues promptly to prevent escalation, focus on solutions rather than blame.

Seek Mentorship and Continuous Learning

No one becomes a great manager overnight. Seek guidance from experienced leaders, attend management training, and continuously refine your leadership skills. Find a mentor within your organization, read leadership books, and attend workshops, ask for feedback from your team, and adjust accordingly.

Embrace the Journey

Transitioning from peer to manager is a significant career shift that can feel challenging, but with the right mindset and strategies, you can earn respect, build strong relationships, and lead effectively.  To do so requires confidence, communication, and adaptability. By setting clear expectations, maintaining professionalism, and continuously learning, you can successfully lead your team while earning their trust and respect. Accept the learning curve, seek mentorship, and continuously refine your leadership skills to succeed in your new role.  Embrace the journey and remember—great leaders are made through experience and growth.

And if you need help, ask!  Coaches can help you navigate the challenges that you face as you make this transition.  Reach out if you want to learn more about how coaches can help with transitioning from peer to manager.

Fostering Trust Among Team Members

Fostering trust among team members is one of your most important roles as a leader.  Have you ever led a team where there was little to no trust?  Did you feel helpless, yet accountable for turning things around?  I’ve been there.  As a leader, you understand the importance of trust and how easily it can be broken, yet how difficult it is to rebuild.  It is the glue that holds great teams together. It’s what allows people to speak up with ideas, admit mistakes, and rely on one another under pressure. Without trust, collaboration turns into competition and innovation stalls. So, how can leaders help build it? One drop at a time.

Start with Transparency

Trust begins with transparency. Leaders can set the tone by openly sharing decisions, goals, and challenges—even when the news isn’t great. When team members see authenticity and vulnerability from the top, they’re more likely to reciprocate. Team members, too, can build credibility by being honest about deadlines, asking for help early, and admitting when they’re uncertain. This kind of candor clears space for real connection and problem-solving.

Create Safe Spaces for Communication

It’s hard to trust people you don’t feel safe with. That’s why psychological safety—the belief that you won’t be punished for speaking up—is foundational. Encourage team norms where every voice counts, and feedback is given constructively, not critically. Consider adding regular “retrospectives” or reflection meetings where people can discuss what’s going well and what could improve, without fear of blame. This helps clear the air and strengthens mutual respect.

Follow Through and Stay Accountable

Reliability is the engine of trust. When teammates consistently do what they say they’ll do, others learn to count on them. That doesn’t mean being perfect—it means communicating proactively and holding yourself accountable. If things slip, own up and reset expectations. When everyone on a team knows they’re rowing in the same direction, trust deepens.

Celebrate Strengths, Understand Weaknesses

Trust is about more than performance—it’s about humanity. Taking time to understand each other’s work styles, strengths, and quirks helps build empathy. Tools like personality profiles or “get-to-know-you” exercises can spark this insight. Equally important: recognize that every team member contributes differently. Celebrating these differences builds appreciation and confidence in each other.

Build Social Bonds

People trust people they know—not just professionally, but personally. Investing time in casual, non-work interactions can pay big dividends. Whether it’s team lunches, virtual coffee chats, or a group playlist everyone adds to, shared experiences create familiarity and rapport. Even small acts of kindness—checking in after a tough meeting, or remembering a teammate’s birthday—go a long way toward building genuine connections.

How do you Repair Trust Once It Has Been Broken?

Repairing trust in a team isn’t just about fixing what’s broken—it’s about rebuilding stronger foundations. Here are some ways you can encourage your team members to do that:

  1. Acknowledge the breach
    The first step is recognizing that trust has been damaged. Whether it was a missed deadline, a broken promise, or a communication breakdown, naming the issue shows accountability and opens the door to healing.
  2. Apologize sincerely
    A genuine apology—without excuses—goes a long way. It signals humility and a willingness to take responsibility. This is especially powerful when it comes from leadership, but it matters at every level.
  3. Understand the impact
    Take time to listen to how the breach affected others. This builds empathy and shows that you’re not just focused on moving on, but on making things right.
  4. Outline corrective actions
    Trust isn’t rebuilt with words alone. Share what steps you’ll take to prevent the issue from recurring. This might include new communication norms, clearer expectations, or more consistent follow-through.
  5. Invite collaboration
    Rebuilding trust is a team effort. Ask others for input on how to move forward. This not only empowers the team but also reinforces that everyone has a role in creating a healthier dynamic.
  6. Be consistent over time
    Trust is earned in drops and lost in buckets. Rebuilding it takes time and consistency. Keep showing up, following through, and being transparent—even when it’s uncomfortable.
Trust as a Catalyst

Fostering trust among team members is one of your most important roles as a leader. Trust doesn’t appear overnight. It grows slowly, interaction by interaction, built on empathy, reliability, and a shared sense of purpose. But when it does take root, it becomes a powerful catalyst for creativity, resilience, and true teamwork. Reach out if you want to talk more about strategies to help your team members build, keep, or restore trust.

Coaches Help Clients Build Professional Networks

Coaches help clients build professional networks.  Do you have a strong network?  Could it be stronger?  Do you like networking?  Some leaders find networking to be exhilarating while others (usually introverted leaders) find it exhausting.  Regardless of how you feel about the process, networking is all about relationships.  And relationships are what matter most when it comes to long-term career growth and business building. This is where professional coaches play a pivotal role. A good coach helps individuals refine their relationship-building skills, set goals, and, most importantly, build connections that foster career advancement and growth.

The Role of a Coach in Networking

Professional networking is a fundamental element of career growth, and coaches provide a structured approach to making meaningful connections. They act as guides, helping individuals identify key influencers in their industry, reach out to potential mentors, and leverage opportunities that align with their professional aspirations. Through tailored coaching sessions, individuals learn how to strategically expand their networks to gain valuable insights, job opportunities, and potential clients.

One of the main ways coaches support networking is by helping professionals develop the confidence and communication skills needed to engage with industry leaders and prospective employers. Many professionals struggle with initiating conversations or maintaining relationships with key contacts. Coaches offer personalized strategies, such as how to craft a compelling elevator pitch, engage in productive conversations at networking events, and follow up with contacts effectively. These skills not only enhance networking abilities but also create lasting impressions with potential employers, investors, or collaborators.

Coaches also introduce their clients to professional networking platforms like LinkedIn, guiding them on how to optimize their profiles, participate in discussions, and connect with professionals in their field. Leveraging these platforms efficiently can open doors to new career paths, industry insights, and collaborations that might otherwise be inaccessible.

Why Networking is Crucial for Professional Growth

Professional growth is often linked to the ability to tap into new opportunities, gain knowledge from experienced individuals, and receive guidance along the way. Networking fosters these aspects by allowing individuals to build a circle of influence that can offer career advice, business opportunities, and skill development.

For job seekers, networking is often the gateway to hidden opportunities. Many positions are filled through referrals rather than job postings, which means having the right connections can make all the difference in securing employment. Coaches help their clients access these opportunities by guiding them through informational interviews, industry events, and mentorship programs so that they can be top of mind when a new role becomes available.

Beyond job searching, networking is crucial for professional development, enabling individuals to stay informed about industry trends and gain insights from seasoned professionals. Engaging with a diverse network exposes professionals to different perspectives, strategies, and innovations, ensuring they remain competitive in their field. I encourage my clients to build relationships with mentors, peers, and industry leaders who can provide guidance and support in navigating challenges.

Effective Networking Strategies

Not sure how to get started?  Here are a few effective networking strategies to help professionals build meaningful connections and advance their careers. Here are some key approaches:

  1. Identify Your Networking Goals – Before engaging in networking activities, define what you want to achieve. Whether it’s finding new clients, collaborating with industry peers, or gaining mentorship, having clear goals helps you focus your efforts.
  2. Build Genuine Relationships – Networking isn’t just about collecting business cards; it’s about forming authentic connections. Coaches emphasize the importance of sincerity and mutual value exchange when engaging with others.
  3. Leverage Social Media – Platforms like LinkedIn provide excellent opportunities to connect with industry professionals. Coaches recommend optimizing profiles, engaging in discussions, and sharing valuable content to establish credibility.
  4. Attend Industry Events – Conferences, seminars, and networking meetups are great places to meet professionals in your field. Coaches suggest attending events that align with your interests rather than just general networking gatherings.
  5. Offer Value First – Instead of focusing on what others can do for you, coaches advise adopting a “give first” mindset. Providing support, sharing insights, and helping others foster stronger relationships and increases the likelihood of reciprocation.
  6. Follow Up Effectively – After meeting new contacts, following up with a personalized message or scheduling a catch-up call helps maintain relationships. Coaches stress the importance of consistency in networking efforts.
  7. Engage in Online Communities – Participating in professional groups and forums allows individuals to connect with like-minded professionals, share knowledge, and stay updated on industry trends.
Professional Networking is Essential for Growth

Coaches help clients build professional networks that are essential for career growth. They provide the tools, confidence, and strategic guidance necessary to foster meaningful connections, open doors to opportunities, and enhance professional development. In a world where relationships often determine success, investing in a coach can be one of the most effective ways to accelerate one’s career and achieve long-term professional goals.  Reach out if you want to learn more about how coaches help clients build professional networks.