Stranger in a Strange Land, Indeed …

by  John E. Smith  |  Career Development
Stranger in a Strange Land, Indeed …

I am slowly learning how to be effective in a much different environment than I have ever faced before … there is some learning here, methinks.

Over the long haul, I have served in leadership positions in the military, on college campuses, at corporations (both for-profit and non-profit), with volunteer organizations, and in social groups. My experience includes volunteer and paid positions at the individual contributor level, as a small-group leader/supervisor, business unit manager and director, up through senior staff level.

I thought I knew organizational leadership fairly well because of the scope of my experience and the varied environments in which I have worked and developed.

The focus in all cases has been on transformation of people, processes, and organizations.

However, I now find myself working in a highly-charged sales environment … responsible for my own actions and my own business. This is a whole new ball game.

I am a transformational guy in a transactional world.

Some quick observations about my learning to date:


Not just about size, but also about hierarchy and lines of communication, production, and organization. Generally, as the size of the organization grows, so does the complexity. This means more opportunities for miscommunication, lack of connection, and people working at cross-purposes or at least less effectively than they could be.

A second thought is that lack of complexity does not equal effectiveness. Ever work in a family-owned business? Small number of employees, intimate atmosphere, but the emotional complexity can be deep and dangerous.

This sales environment is medium-level complexity with a strong emphasis on legal processes and the involvement of a very large amount of money for most people. Complexity can be represented by more than just organizational boxes.

Complexity changes our behavior and communication in some ways, but the impact of complexity appears remarkably consistent and scalable.


Who you deal with is important and this varies quite a bit too. In the military, clear lines of command and subordination, along with clear and detailed guidelines for almost every situation, exist side-by-side with the critical need to act independently when one of those situations call for it.

Ultimately, managing people is always an individual project, but for those within organizations, group dynamics matter.

As you move away from clear lines of authority, you increasingly encounter others who can resist, ignore, or sabotage your leadership. This exists in all organizations to some degree, but when you factor in the competitive nature of working with a whole group of self-employed folks, the questions around who has authority and how they wield that authority become more important.

However, individual differences are always critical and we ignore the person versus the group at our peril.


Leadership is probably easier for most in large organizations, where roles and responsibilities are clearly delineated and the structures support working in teams toward commonly accepted goals. Everyone knows their place in the scheme of things. When you have the title, authority, and accountability, you can usually confidently act, knowing that you are supposed to be doing what you are doing.

However, leadership within a group of independent and self-employed individuals is proving to be different than I have experienced.   It’s not just about individuality or who has the authority, either. I have worked with volunteers at the local, regional, and national level at times, and volunteers are not the same as self-employed colleagues. I am slowly noting the differences and similarities, as a good life-long learner should do.

Most importantly, leadership in this environment has little or nothing to do with rank, title, or the other traditional outward markers of a leader. Status is conferred based more on success in the sales arena and relates only weakly, if at all, to leadership success.

Since transactions are the daily bread of our efforts, we are challenged to find a constant focused on customer service in each interaction, no matter the level of sales success each party has experienced. How does leadership manifest itself in small and big ways through the prism of these transactions?

Of course, some things about leadership, such as integrity and honor, do not change, even as we move from one environment to another. The person who is honest, candid, and willing to take risks to champion the truth is always in short supply and valued by thinking people both inside and outside the organization.

If I misrepresent a property to someone or take unfair advantage in a business transaction, I am acting out of accordance with my own ethics.

Other leadership traits, such as vision and strategic thinking, take on new meanings when everyone has their own personal goals and dreams. While individual efforts contribute to the agency’s success, we are all on our own regarding establishing our goals and deciding best how to achieve them.

I think leadership in this arena is leadership of the individual by personal example and influence. That’s a lot harder than when everyone is obligated to work toward the same goals in the same way.

SO ….

Obviously, these are incomplete and preliminary thoughts about leadership in a strange new world (at least to me). I plan to continue considering how my new world is the same and how it is different. I would welcome any questions or comments on my observations.

What has your experience been in highly competitive markets where everyone is self-employed, self-motivated, and self-directed?
Photo Credit: kmlmtz66/123rf

About The Author

Articles By john-smith
I enjoy helping people learn and grow through intentional, strategic, and social interventions. I coach, teach, train, facilitate, organize, write, speak, design, and lead at the intersection of leadership, learning, and human behavior. I am a CCE Board Certified Coach (BCC) with specializations in both Leadership/Business and Life/Personal coaching. My primary blog is The Strategic Learner on Wordpress.  »  View Profile

What People Are Saying

David Dye  |  30 Sep 2016  |  Reply


I’d enjoy any post that includes a good Heinlein reference, but on top of that you’ve shared an important and vulnerable look at real life. We’ll often find ourselves in transition and and our ability to transfer what really matters into a new context is vital – but not at all easy. Just look at all the superstar CEOs who move to a different context and do not succeed at the same level.

Thank you for the thoughtful and thought-provoking post!


John E. Smith  |  02 Oct 2016  |  Reply

Hi, David:)

I also like to remind myself of the Master from time to time as well.

I appreciate your kind words, especially coming from such an accomplished and articulate person as yourself. Thanks:)


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