A Lesson from 100 Conversations
A Blog Article Originally Written On 100Peoplein100Days.
20 Jan 2025
It all started during a lunch break at the Cambridge Judge Business School. I was attending the Senior Management Programme when one of the lecturers, Mark, shared a deceptively simple but powerful idea: if you’re at a crossroads in your career, the best thing you can do is listen. Speak to as many people as you can, and give yourself the space to reflect.
At the time, I’d recently and unexpectedly left a company I’d loved working with for over five years. It left me feeling untethered. The Senior Management Programme was invigorating—full of fresh ideas and strategies I was eager to explore—but I wasn’t clear on my next steps. That’s when Mark suggested the “100-people-in-100-days” challenge. It wasn’t complicated: meet people, ask questions, and most importantly, listen.
Setting a Goal, Then Surpassing It
While I initially committed to meeting 100 people in 100 days, I ended up far surpassing that goal. I’ve also lost count of how many conversations I’ve had since then. But the number itself isn’t what matters—it’s the process. Setting an initial measurable goal gives you a tangible challenge. It feels daunting but doable. As I worked through it, I found myself caught up in the “doing.”
Along the way, I built confidence and momentum. One of the biggest surprises was how the challenge expanded my network far beyond healthcare. I reached out to people outside my industry, people I thought would be fascinating to speak to. Many were strangers who generously gave me 30 minutes, an hour, or sometimes more of their time.
I started feeling braver, too. For example, at a prestigious event, I reached out to the MC because I admired how she presented the speakers. We ended up having coffee, and now we’re collaborating on a project together. Some of these conversations took place during dog walks, which is a wonderful way to put people at ease and enjoy the flow of an open, informal chat.
Sharing Stories and Building Connections
As I became more active in reaching out to people, I realised that every conversation held a lesson worth sharing. I started posting key takeaways from my chats on LinkedIn—always with the person’s permission, of course.
This was quite a big step for me. Like many, I felt nervous about putting myself out there on social media. But as I shared more, I grew braver. Each post was simple: one insight, from a conversation with someone I deeply respected, that I thought others might benefit from.
The response was incredible. People began reconnecting with me or reaching out for the first time. I’d get messages like: “Would you mind chatting with this person? I think you could help them” or “I saw your post about X and wondered if you had time for a coffee.”
These conversations took the challenge to another level. It wasn’t just about expanding my network anymore—it was about creating more real, meaningful connections and becoming part of a wider conversation.
Listening First, Then Finding Clarity
What started as a structured exercise quickly became transformative. A few weeks in, I realised I wasn’t just exploring my career options—I was building the foundation for my consultancy. At first, I wasn’t intentionally talking about my plans or trying to “sell” my services. But inevitably, people would ask, “So what are you up to?”
Answering that question over and over forced me to articulate my plans. I practised my elevator pitch and refined my value proposition. With each conversation, I tested different ways to position my business and observed how people reacted. Their questions and feedback were so valuable.
This process highlighted something I hadn’t fully appreciated before: I wasn’t clear enough on what my services brought to a business. For the first time—outside of job interviews—I had to promote myself, not my company. But I wanted to do it in a way that felt humble and authentic. This constant refinement helped me clarify my message and build confidence in how I presented myself and my business.
What I Learned
Here are the lessons that stayed with me:
People want to help. When you approach with genuine curiosity, others are surprisingly open and generous.
Curiosity beats over-preparation. Be ready to listen instead of trying to steer every conversation.
Insight comes from reflection. The most valuable ideas often emerge after the conversation ends.
Growth happens outside your comfort zone. Every new connection brings new perspectives—and courage.
Clarity comes from practice. Talking about your plans regularly helps you refine your pitch, find your voice, and gain confidence.
A Simple Idea with a Big Impact
This challenge wasn’t just about figuring out my next career move. It became a way to build authentic connections, refine my value proposition, and support others.
The conversations I’ve had—and continue to have—have been transformational. And I’m proud to say that one key milestone in this process was registering my company, Alma Business Consulting, this new year.
This was an important step. It gave a name to what I’d created through this journey and formalised my commitment to taking my career in hand and leading my new path. While this milestone marks the end of the 100-day (plus!) challenge, I have no intention of stopping.
Pencilling in great conversations with new people and people in my network several times a week has become a habit—and one I’ll keep.
