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Contextual intelligence as the leadership’s winter coat

by reporter
June 3, 2025
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By Onesmus Keudaneko Joseph

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Why do nearly 70% of strategies and decisions fails? It’s rarely because the strategy is wrong. More often, it’s because leaders fail to adapt to context.

In the midst of globalization, emerging technology, global citizenship awareness and the advent of the global organization, the contextual environment in which leaders must operate is increasingly complex, even mind-boggling.

I meant success doesn’t belong to those with the loudest voices or the longest experience, it belongs to those with the clearest contextual judgment.

Like Israel, in the days of the sons of Issachar, there is a clarion call for leaders who can both diagnose the context they are in then exercise their knowledge to know what to do in the midst of changing and turbulent times.

Over the years of practicing strategy and thought leadership, I have become an advocate of a concept many often overlook, contextual intelligence. I recall that earlier in my career, much emphasis was placed on emotional intelligence and rightly so.

However, as I pen this piece, it has become clear to me that investing in contextual intelligence is no longer optional; it is an urgent priority, both at the personal and corporate level.  The world of business is a dynamic theatre shaped by environmental conditions, organizational culture, generational diversity, and complex social forces. 

These realities influence how leaders lead, how strategies are defined, how they are implemented, and how progress is monitored. “Vati ehe kulombwele keshiwoye; ye onamatwi udako.” If you have ears, listen, what you take from this reflection might benefit you as an individual, your organisation or someone in your circle.

In various strategy sessions and workshops, I have facilitated or participated in, one recurring concern continues to surface: Why has leadership become increasingly difficult in recent years?

While I don’t claim to have all the answers, I am often tempted to believe that part of the challenge lies in our failure to apply timely, modern tools that align with the complexities of the current environment. To lead effectively leaders must operate with contextual awareness, deep comprehension, and intentional care. Yet, the truth is, we rarely pause to fully unpack what that really means.  

Leadership in 21st century is no longer about simply being right; it is about being relevant.  Someday, I will write on the role of office politics on leadership but today, “andiya ndiukilile omungalirea ou”, allow me to remain with the subject of contextual intelligence

Contextual intelligence is a leadership competency that integrates concepts of diagnosing context and exercising knowledge. Contextually intelligent leaders are multi- tasking thinkers who routinely go outside of their existing context to acquire useful information about the world in which they live and integrate that information into their decision making.

This means leadership must never be one-size-fits-all. The way you lead in a boardroom should not mirror how you lead in a staff meeting. The tone, the message, the energy, and the expectations must be tailored to the context and the audience. This is the art of situational judgement, and it sits at the very heart of contextual intelligence.

As managers and leaders, we are guiding teams made up of people from different backgrounds, beliefs, and languages. What unites them is a shared organizational vision and set of values.

But people are not machines. They cannot simply “download” values. They must internalize and personalize them; only then can they truly live the organizational culture. For instance, look at a current workforce of the day. We have Baby Boomers, Millennials, and Generation Z all working under one roof.

They do not consume information the same way, they do not respond to authority in the same manner, and they do not value the same things equally. While organizational values may unite them on paper, in practice, leading these groups requires different levels of engagement. 

Some managers insist, “We are all here for the same reason.” That may be true, but human beings do not operate mechanically. When you treat people as machines, don’t be surprised when strategy fails to land.

I am sure you have lived long enough to recall one or two leaders, perhaps even within your own circle who failed simply because they could not lead with context. In practice, when an individual is given the responsibility to lead, the instinct is often to rush into strategy execution without reflecting on the essential ingredients that drive effective leadership. I am here to tell you: contextual intelligence is one of those non-negotiable ingredients. And we must summon it, embrace it, and apply it constantly.

The way we lead must evolve. The ability to read a situation, understand your audience, and adapt your tone, message, and approach is what separates mediocre managers from transformational leaders.

The same strategy, when applied in a different context, may require a different execution plan. That is not weakness, it is wisdom. Context matters. Culture matters. People matter. 

Leadership at this level is no longer about being right, it’s about being relevant. And relevance requires context. Therefore, just as you wouldn’t face winter without a coat. Don’t lead without context.

*Onesmus Keudaneko Joseph is Business Strategy Practitioner with a strong focus on strategic foresight and futures literacy. He is currently the Manager for Intellectual Property Enforcement and Frameworks at BIPA. He writes in his personal capacity.

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