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The Pilot Pen, Revisited: Why Context Matters in Leadership

The Pilot Pen, Revisited: Why Context Matters in Leadership

A while back, I shared a story about how my sister and I, as teenagers living in a small slum in Mumbai, saved for weeks to buy a Pilot Pen. That pen taught us our first lessons of leadership in goal setting, perseverance, and shared purpose.

Today, I want to tell you what happened thirty years later.

By this time, life looked very different. I was living in the US, and my sister had built a good life for herself and her family. During one of my trips to India, while shopping for gifts, I came across a pack of Pilot Pens, ten of them, neatly arranged in a box.

It instantly brought back a flood of memories from those long nights at the factory, the excitement of saving every rupee to the day we finally held that shiny pen in our hands. It felt symbolic. So, I bought the pack, thinking it would be a meaningful gift for my nephew, something that would connect him to our story and maybe inspire him the way it once inspired us.

A few years later, I was visiting India again. While working on some paperwork at my sister’s house, I asked my nephew to bring me one of those pens. He looked at me for a second and said casually, “I lost them.”

All of them.

I won’t lie, I was angry. For me, those pens carried decades of meaning. They weren’t just pens. They represented struggle, resilience, and pride. Losing all of them felt careless, almost disrespectful.

Later that evening, I talked to my sister about it. She listened quietly and then asked a few questions that completely shifted my perspective.

She said, “Did you ever tell him why you bought those pens? Did you explain what they meant to you, or what they symbolized? Did you share the story behind them? Or did you just assume he would feel what you felt? And one more thing: did you buy those pens for him or for yourself?”

Those questions hit me hard.

The truth was, I hadn’t given him any context. To me, the Pilot Pen was a symbol of hard work and aspiration. To him, it was just… a pack of pens. Something he could easily replace.

That moment reminded me of an important leadership truth – meaning is not automatically transferred; it must be communicated.

Just like my nephew couldn’t appreciate the story behind those pens without context, people on our teams can’t fully connect to a goal or a vision unless we help them understand why it matters.

Here is what I took away from that experience:

  • Context builds connection. If you want people to care, help them see the meaning behind the mission.
  • Empathy matters. Not everyone’s journey is the same. What feels sacred to you might feel ordinary to someone else.
  • Clarity beats assumption. Expectations left unspoken often lead to disappointment.
  • Purpose should serve others, not just yourself. Leadership isn’t about reliving your story through others; it’s about helping them write their own.

That day, I learned that leadership doesn’t stop at setting goals or achieving success. It’s about storytelling, giving meaning, sharing purpose, and helping others understand the why behind the what.

And just like that, the same Pilot Pen that once taught me the power of ambition, taught me again – this time, the power of context.

 
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Posted by on October 24, 2025 in 21st Century, Leadership

 

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Tips for Effective Big Room Planning and Alignment Sessions

Tips for Effective Big Room Planning and Alignment Sessions

In today’s complex business landscape, cross-functional collaboration is vital for delivering valuable programs and products, whether in start-ups, small businesses, or large organizations. Technical Program Managers (TPgMs) play a crucial role in ensuring smooth operations within these collaborations. One of the key practices they employ is conducting Big Room planning or alignment sessions to execute strategic programs. In this blog, I’ll share some valuable recommendations to make these sessions more effective.

Clear Agenda: Begin by setting a clear agenda for the meeting. Surprisingly, 67% of meetings lack a well-defined agenda. Providing context through a meeting invite with a clear agenda is crucial. This enables attendees to come prepared, leading to a more productive discussion.

Timing Considerations: With teams spanning different time zones, it’s essential to choose a time that accommodates most key stakeholders. If finding a suitable time for everyone proves challenging, consider working individually with those unable to attend and find alternatives, such as sending delegates to represent them.

Single Threaded Leaders (STLs): Prior to the session, identify domain owners and communicate their roles and responsibilities. Designating Single Threaded Leaders for each function ensures clear accountability and presence of the right leaders for decision-making.

Do Your Homework: To avoid getting derailed during the meeting, it’s crucial to be well-prepared. Invest time in envisioning the discussion and collecting necessary data beforehand. Engage with relevant leaders to obtain high-level estimates or information required for the session.

Focus on the Outcome: Keep the meeting focused on outcomes rather than outputs. As a technical program manager, steer discussions towards the broader objectives. Should conversations veer towards minutiae, encourage participants to address those matters separately.

Summarize and Send Meeting Notes: To conclude the session, summarize key points and action items before ending the call. Taking notes during the meeting is crucial for this step. Afterward, send out comprehensive meeting notes to all participants. This fosters clarity on objectives and action items, allows for upward reporting, and promotes unified understanding among team members.

Conducting effective Big Room planning and alignment sessions requires careful planning, facilitation, and attention to detail. As a technical program manager, your role is to orchestrate these meetings to maximize collaboration and drive successful outcomes.

I hope these tips prove helpful for your future sessions and enable you to achieve greater efficiency and alignment within your cross-functional teams. Feel free to share your thoughts and experiences in the comments below. Happy planning!

 

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