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Why these questions can help leaders assess context 

Leaders need to ask hard questions to assess context in their organizations, and here's where the 5 W's (and 1 H) can help.

5 min read


Why these questions can help leaders assess context

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This post is by Meredith Persily Lamel in partnership with Weaving Influence, a full-service digital marketing agency. Since launching 10 years ago, Weaving Influence has helped clients launch more than 150 books, carving its niche in working with authors, thought leaders, coaches, consultants, trainers, nonprofit leaders and speakers to market their services and books.

A major responsibility of leadership is the need to look ahead and plan for the organization’s future. This requires not only extra care in assessing an organization’s current situation, but also paying attention to those emerging areas that will define the organization’s future. To that end, leaders must assess context from the inside out.

While the questions leaders ask to properly assess context are infinite, we can thank sixth-grade English teachers for reminding us to incorporate the commonly referenced 5 W’s and our lonely H.

Who are my stakeholders?

Defined simply, a stakeholder is anyone who can claim access to our time. These are colleagues, customers, constituents and competitors, among others.

To begin to understand and assess context, the first step is to define your networks and where you sit within them. As you draw these network maps, assess the strength of these relationships, as well as the interconnectedness that reflects the system in which you are operating:

  • How have your stakeholders and their interests changed?
  • How might they evolve in the future?

From there, leaders can more intentionally develop and prioritize those key and emerging relationships.

What do my stakeholders want and need from me?

What do I want and need from them? Influence is a series of exchanges. What criteria are stakeholders using to evaluate leaders? Shareholders may be focused on the bottom line, while our employees look to leaders to foster a desirable culture and environment.

If you have not done a listening tour to ask your stakeholders their expectations of you and what great leadership means to them, you have a critical opportunity awaiting you to better understand where the bar sits as others assess your leadership.

When in time is my leadership needed?

In other words, where in an organization’s growth cycle are you sitting? If it is a high-growth organization, did you grow along with the company or are you still operating in start-up mode? How are you thinking about your leadership in the context of scaling?

Many organizations change CEOs when the company enters a new cycle of maturity. While not necessary, it reinforces the argument that organizations in various stages of growth require new mindsets and behaviors from their leaders.

Where are the most pressing opportunities for you to have an impact?

Leaders provide a focus for an organization among the many competing priorities. They have to identify where their leadership will matter most. Most likely, it is not about the bright, shiny object that everyone else is paying attention to.

We expect our leaders to identify those places where the leadership is most needed because either no one is noticing or the complexity is overwhelming the system. Our leaders have the opportunity to identify and step into the chaos to provide clarity and meaning for those who need it most.

Why should anyone follow me as a leader?

We want those around us to root for our success. But why should they? And, perhaps just as important, why might they not? To expect others to blindly follow our leadership is to ignore the choice people are making each day about whether to follow.

Leaders need to not only assess the why — which is different across stakeholder groups — but they have to continually communicate it. For leaders, connection to their work and mission may be second nature, and it’s easy to forget that stakeholders need this connection to be communicated and demonstrated regularly.

In addition, motivations even within similar stakeholder groups vary dramatically. Leaders must hone and customize these messages constantly to engage both the hearts and minds of those they lead.

How did you come into your leadership role?

In our book “Six Paths to Leadership: Lessons from Successful Executives, Politicians, Entrepreneurs, and More,” Mark Clark and I outline six different paths into leadership positions (elected, appointed, promoted, hired, founded and family-legacy). We offer a set of insights and actions for each distinct path that allow you to maximize your opportunities for success and manage the associated challenges.

Leadership is not a one-size-fits-all job, and by using this “six paths” framework of questions, you’ll better understand and assess context and how you fit into your specific role as a leader. Whether an emerging or experienced leader, your journey is unique. These six paths will help you navigate your destination for long-term success.

Meredith Persily Lamel is CEO of Aspire@Work and co-author of Six Paths to Leadership: Lessons from Successful Executives, Politicians, Entrepreneurs, and More.” As an executive coach, consultant, facilitator, and professor, Lamel specializes in the leadership challenges of complex, global organizations including technology, healthcare, financial services and government.

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