Becoming a Trusted Leader: Context Is Everything

In the realms of business, technology, and leadership, understanding and wielding context can become the most potent tool in your arsenal

Alex Gervais
4 min readOct 21, 2023

When I reflect on my journey at Ambassador Labs, one word that continually emerges as a guiding force behind my successes is: “Context”. It’s a term that, on the surface, might seem abstract, but in the realms of business, technology, and leadership, understanding and wielding context can become the most potent tool in your arsenal.

Photo by Jonas Gerg on Unsplash

The Essence of Context

At its core, context is about understanding the bigger picture. It’s not merely about knowing the ‘what’, but understanding the ‘why’ and the ‘how’. When you possess a clear grasp of the context, you’re no longer moving based on instincts or vague insights, but with purpose and direction. This understanding was pivotal as I navigated my journey from a Senior Software Developer to Director of Technology.

Why ‘Why’ Matters

Simon Sinek famously posited, “Start with Why”. In essence, the ‘Why’ is the bedrock of context. It answers the fundamental questions: Why are we doing what we’re doing? Why does it matter? When leaders articulate the ‘Why’ with clarity and conviction, they create a powerful narrative that aligns teams, inspires action, and fosters trust. During my time at Ambassador Labs, ensuring that every team member understood the ‘Why’ behind our initiatives was central to our collective success.

Context in Decision-Making

In the business world, information is abundant. However raw data is meaningless if not translated into actionable insights. This is where context shines. For instance, let us consider balancing a portfolio of work between product and technical work, such as addressing scale — maintenance, efficiency, performance, availability — and risk. By understanding the business context, I could prioritize tasks not just based on their technical importance, but also their business impact.

Furthermore, grasping the broader business vision or ‘North Stars’ and then transforming them into actionable outcomes and OKRs (Objectives and Key Results) became second nature. In the end, we are all judged on the outcomes of our work, not the activity of work.

Openness and Context: A Winning Combination

A critical lesson I learned is that context should not be a closely guarded secret. For a team or organization to truly excel, leaders must be open about setting the scene. Sharing the broader vision, strategies, challenges, and opportunities helps everyone align their individual efforts with the collective goals. Leading is about direction, not directives.

By fostering this openness, we empower every team member, from interns to senior leaders, to make decisions that resonate with the organization’s objectives. They can innovate, challenge, and contribute in ways that genuinely matter.

Building Trust Through Context

Trust isn’t bestowed; it’s earned. One of the fastest ways to earn it is by providing clear context. When team members understand the reasons behind decisions, the objectives of projects, and the implications of their work, they not only feel valued but also become more invested. An open dialogue about the broader context, peppered with transparency and consistency, became my recipe for fostering trust.

The Art of Storytelling

One of the most powerful tools a leader can wield is the ability to craft and convey compelling stories. Storytelling transcends mere communication. It’s about weaving the threads of context, mission, and vision into a tapestry that resonates with people’s emotions and intellect. I found that breaking down complex strategies into relatable stories made it easier for the team to internalize our goals and work towards them with passion. Moreover, a well-told story can be the catalyst for change, the spark for innovation, and the glue that binds a diverse team together.

From Context to Mastery

My accelerated progression from a Senior Software Developer to Staff-level and eventually to Director of Technology was not merely a result of my technical skills. While those played a significant role in the beginning, it was my relentless pursuit of understanding the context that made all the difference.

By internalizing the context, I could lead projects that resonated with our business goals, mentor and teach others with a clarity that only comes from deep understanding, and make decisions that were timely, impactful, and aligned with our company’s broader vision.

The Wisdom in Humility

There’s an adage that if you’re the smartest person in the room, you’re in the wrong room. While I’ve been fortunate to hold positions of leadership, a pivotal realization for me was acknowledging that I didn’t have all the answers. And that was okay. Surrounding myself with leaders from other divisions or business functions was not a sign of my inadequacy, but a testament to the power of collective intelligence. Each interaction was a learning opportunity, each discussion a chance to broaden my perspective. Embracing this approach not only fostered cross-functional collaboration but also enriched my personal growth as a leader.

Make It About You

Your journey is defined not by the steps you take, but by the understanding behind those steps. Cross the river by feeling the stones. Seek context, and you’ll find your path.

Should you find yourself grappling with your own context or in need of guidance on any subject, please don’t hesitate to reach out. I am genuinely invested in helping others navigate their professional paths, and I’d be delighted to offer ad hoc mentoring sessions. After all, the best way to learn is through shared experiences and collective wisdom. Let’s embark on this journey together, deciphering the context that shapes our individual and shared successes.

I’m available here on Medium.com, and LinkedIn as well. Drop me a brief introduction, and let’s start a conversation!

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Alex Gervais

Outdoorsy, data-driven, eternal student, not so geeky creative mind and traveler. Distributed Systems Architect & Tech Lead. ex-Ambassador Labs, ex-AppDirect