Exclusive Interview with Deb Cupp, President, Americas, Microsoft

Welcome to the second edition of the Trailblazing Women newsletter - your weekly dose of inspirational leadership insight.

As always, to meet the needs of all our readers, there will be three key aspects to today's newsletter edition:

1. The interview – a 15-20 min conversation covering the how, the why and the impact
2. A summary – a way to capture the key insights until you have time to watch the whole interview
3. Next steps – how to incorporate this advice today, this month, within the year, and throughout your career

If I've missed something, let me know and I'll do my best to include it next week.

And finally, thank you for subscribing. If you haven't yet, give it a go and I'll ping you when we launch the interview each week.

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In the corporate world, leadership is synonymous with success. More people, more execution, bigger targets, bigger pay checks. It's the next logical step, and the ultimate goal for many.

But in this week’s episode of Why-How-Impact, it became very apparent that the true essence of leadership is often misunderstood until one is actually in the role.

And, as a result, not everyone is there for the right reasons.

True leadership goes beyond mere management; it is about inspiring, influencing, and innovating. It requires a deep understanding of both the mission of the organization and the diverse needs of its people.

One person that is unequivocally there for the right reasons is Deb Cupp , President, Americas, 微软 . We need more leaders like Deb.?

Watch the Full Interview

For many, the path to leadership is a series of logical steps. You excel in your current role, you take on more responsibilities, and eventually, you find yourself in a leadership position. This progression feels natural, almost inevitable. However, this journey often lacks a fundamental understanding of what it truly means to be a leader.

When I asked Deb about her purpose and why she pursued leadership, she admitted that it was just a natural progression – a new challenge and an opportunity to grow. It wasn't until she had found her way around a few roles that she realized leadership wasn’t about being the smartest person in the room.

Be a Generalist, Create that North Star

Deb's journey in leadership evolved from a personal challenge to a mission of empowering others. This shift is a common thread among each of the Trailblazers I have had the pleasure of speaking with so far.

Initially, the focus is on proving oneself, climbing the career ladder, and demonstrating competence. But true leadership is about moving beyond what you know and harnessing the collective brilliance of the team.

"I don't need to be the best at everything. My job is to get the best out of people and help build the path and create that North Star."

This evolution is not instantaneous. It takes time, experience, and a lot of introspection.?

Deb candidly shared how freeing it was to transition from feeling the need to know everything to embracing her role as a generalist.

Imagine the possibilities if we all embraced this mindset. What if we reframed "executive presence" to mean fostering an environment where every voice is valued?

Create a Trusted Network Around the Business

One more time for the people in the back… You cannot do it all on your own.

And in the same vein, no matter how incredibly brilliant your team are, they also cannot do it all on their own. Your ability to reach business goals, as an individual or a team, is often dependent on your relationships across the business.

Deb's advice on building a trusted network is invaluable, especially when stepping into a new role. Curiosity is a superpower and proactive efforts to connect with colleagues can yield long-term benefits.

So, how do you build a trusted network?

?"Trust comes from being open, honest, and transparent. It comes from vulnerability as well. I'm very okay saying to somebody, 'I don't understand. Can you help me understand that better?'"

But it’s not just about learning from others; it’s about offering support in return. This reciprocity fosters a collaborative environment where everyone thrives. As my mother always said, ‘do unto others as you would have them do unto you’. Be curious, be generous, be vulnerable, and you shall reap the rewards.

The Ripple Effect of Joy

So, what happens when people pursue leadership for the wrong reasons? Well, you often find yourself with a team that emulates the misery of their leader – demotivated, uninspired, and disengaged.?

Conversely, when you have a leader that enjoys what they do and wants to lift up the people around them, you have an incredibly motivated, inspired and engaged team. Luckily, Deb is the latter.

“I do it because it brings me joy. I think that everything we do in life should stem from something that brings you joy… That's what I find in the work that I do in leadership. I think my purpose is really to help people achieve things they didn't think were possible.”

And that has a ripple effect. Effective leaders who foster environments of joy and respect do not only enhance workplace morale, but also inspire people to carry these values into their everyday lives. Progressive leadership is not just about guiding a company towards economic success, but about shaping a more resilient and empathetic society.

How You Can Incorporate This Advice

Today: Start by letting go of the fear of not knowing everything. Embrace your role as a generalist (if that's you) and focus on empowering your team.

This Month: Schedule time to reach out to colleagues and build new relationships. Show genuine curiosity about their roles and offer your support.

Within the Year: Reflect on the joy you bring to your workplace. Find ways to incorporate fun into your daily interactions and team activities.?

Throughout Your Career: Continuously build and nurture your network. Stay curious, be generous with your time, and always prioritize the well-being and growth of your team.

And you've made it!

Leadership is a journey of discovery. It's a path that often begins with self-interest but evolves into a mission of service and empowerment. It's about being curious, vulnerable, and committed to the growth of others.

As Deb’s has shown us, the true essence of leadership is not about knowing all the answers but about fostering a culture of learning, collaboration, and enjoyment.

Please let me know what you thought of the interview - what resonated most with you from Deb's story? How do you plan to implement these insights into your own leadership journey? Is it today, this month, within a year, or in your career?

Join us for Why-How-Impact next week with Tracy Sun , Co-Founder, Poshmark .

And don't forget to subscribe!