Braving the new frontier: Part two of my journey as an intrapreneur

Last year I took a bold step, in the opposite direction that many seem to be taking these days. I let go of working for myself and returned to working as part of an organization. 

In the article I wrote about this transition I described the many perils of self-employment and some of the obstacles (both internal and external) that I faced as I continued my unpredictable journey to becoming otherwise employed. 

Many readers reached out to me after I published the article to ask me how I planned to overcome additional challenges I’d encounter once I was working in an organization. I have found that my best insights come from my direct experience, so I asked them to wait until I had a few more miles under my belt and could offer some practical guidance.

I fully understand their concerns. There really isn’t an easy road these days, whether you choose to hang your own shingle or clock in nine to five. But I still think we have so much work to do and we need to do it together - and only by being true to ourselves will this work germinate and grow what we hope it will.

Why organizations are important

We already know that organizations are complex and challenging, at times even messy and incredibly uncomfortable. In my humble opinion they are also the most potent tool for real, lasting change.

Too often we take for granted that we are social beings, that we literally need each other to survive. Too often we don’t dare to question or reject the status quo. And we greatly underestimate our individual ability to influence collective patterns and progress.

Some who do dare to believe in their potential choose to build new companies, which is great if you think you want to shoulder that kind of financial (and spiritual) burden. I believe that this isn’t enough, however, to “change the world.” There are many institutions not going away that simply need some daring souls to gift them with a swift kick, a brief candle, or an exciting treasure map. 

For example, here are some gifts I’ve recognized in entrepreneurs that I think can be game changers for organizations:

  • Super responders can bring new market information and energy to organizations, which is especially important if they have been stagnant for too long and need to pivot

  • Seed planters can take organizations in new directions, which is especially important if the organization is in the midst of a major pivot or is just getting started

  • Team architects can create momentum toward new visions, which is especially important during and right after a pivot or launch

  • Goliath defeaters can sustain energy through various stages of growth, inspiring others to stretch and helping teams break ceilings

Many institutions in the social sector can become overly reliant on external contractors (people who may be able to offer the gifts listed above but who are outside the organization) for even basic operations. While you’d think this would increase the need and potential for coordination and collaboration, I fear too often this need and potential are unmet, because healthy collaboration is still frankly not the norm.

Organizational change is hard, and it is an absolutely vital part of birthing a new world. Speaking from experience, being a consultant can allow you to too easily hide behind the mask of a “hero;” you are more removed from the relationships that demand the transparency and accountability that makes mutual growth possible. Once you are inside the machine, however, you are better able to see all its parts and thus to substantially change it.

Collaboration is not just more meetings

So how can we improve organizations and make them places we still feel we can be our bold selves in? This is the question I have devoted myself to exploring.

As a consultant, I assisted many organizations in collaborating better with one another; working inside them, I have witnessed that there are quite a bit more struggles to collaborate within them. To me, this comes down to a few fundamental errors in thinking.

Some think they want to be, or even already are, collaborative, but they have yet to define what that really means to them. Collaboration, to me, isn’t merely convening more meetings. It’s about, firstly, having more, and ideally different, people at the table. Then, it’s about really listening to them. Ultimately, this means it’s about leaning into what makes us uncomfortable, and I can appreciate how difficult it is to ask others to do that.

The structure and purpose of, and the skills used at, meetings needs to fundamentally pivot to enable this, but, understandably, habits are entrenched. For example, too often meetings are still lead by one person, usually someone with authoritative power, and their agenda and goals are what the meeting is meant to focus on. Sadly, sometimes even when a “neutral” facilitator is introduced, they are still working to please the singular client more than than the group as a whole, thus the agenda remains top-down.

Facilitators, whether internal or external to the organization, generally vary in style, on a spectrum from acting as a “sage on a stage” to being more of a coach trusting an organic process. I think each of these styles can be successful given the appropriate context, but too often that context is, often unintentionally, ignored. (I think this is not helped by the fact that facilitation is a field with no singular accreditation but plenty of methods that are trademarked and sold so basically anyone can call themselves one.) If the intention is to facilitate the emergence of bottom-up wisdom, a facilitator must let go of being a “hero” and consciously embrace humility and servant leadership (another term that is also often misused IMHO).

If we want humans to be the center of organizations, rather than profits or data or status or any number of other things often value more, we need to design them accordingly. As is often the case when we are stuck, defaulting to arbitrary decisions or past behaviors is preventing us from making things better.


Exploring a middle way

Depending on our position we may or may not feel that we can influence our organization’s policies and practices. This is another error in thinking. I am willing to bet that at many if not all jobs you have had you have known someone whose mere presence has changed the culture of the workplace and how the people they work with feel about going to work, for better or worse. (After all, research shows that most people quit their boss, not their job.)

How can we embody servant leadership regardless of our perceived authority and be someone who makes our workplace better for us and our organization better for our colleagues and communities? Here are some suggestions based on my experience.

If there is one golden rule, I think it is to be willing to listen to and stay true to oneself. One thing that self employment gifted to me was deep clarity on how I bring value to groups, so I return to that knowing whenever I need. I think intrapreneurs are simply people who know how to lead themselves. I am a big believer that leadership is a skill, not a position. Working in an organization, we get even more opportunities to practice honoring our feelings and not taking things personally, as well as modeling for others what that can look like in workplaces that too often keep people small.

The trick is learning to balance “fitting in” (admittedly, something entrepreneurs may not be naturally good at) with breaking through. For me, this learning has been about allowing and even inviting others to better support me. For some, it might also be about learning how to get behind ideas that are not just your own.

Unlike many people, it is often more difficult for me to be part of a group than to be myself; in those moments, I lean on my genuine desire to solve problems real people face as well as the joy I experience when I appreciate and support others’ unique strengths. 

Far more important than a steady paycheck are the steady relationships that are containers for our growth and liberation. We need each other and we are all better off if we are also not hiding our unique gifts and contributions. 

The grass is never greener, but the frontiers can be more fertile

Over the past year many people in all sorts of organizations and situations have posed the question to or around me: “When should I stay and when should I go?” I often answer this question based on the two guideposts already mentioned: What does my gut tell me? Are these relationships a container for growth right now? It’s worth considering a couple more as well.

Firstly: Am I still sharing my gift here, or would another organization be able to benefit from it even more? As an intrapreneur I want to be sure that I am not fully participating in the organization’s problematic patterns but rather supporting a useful shift. So, secondly, I ask myself: Is this a good time to pass the torch?

Asking these questions and answering them honestly requires tremendous consciousness.

I think in our culture we are generally not good at “goodbyes.” When I worked with teams on a project basis, the “pass off” at the end was one of the most important moments in our relationship, and, too often, one of the most careless. When a project with a client ended, however, I knew that client would remain my best source for new ones, so for me it was always more of an “au revoir.”

That being said, sometimes forests need fires to spur new growth and sometimes bridges need burning to release us into new ways of relating. Prescribed burns are not to be taken lightly though. Again, the rule of thumb is listening to one’s intuition, which is not the same thing as reacting knee-jerk. It is a patient process of questioning, discovering, and responding with courage.

It is far easier, of course, to give in to the black-and-white ideology that says you are either a slave to a bad boss or a hero slogging through cycles of feast and famine. If we do listen to ourselves, and to each other, we know better, though.

We know a new world is being born, that the labor will be long, and that it will take a team of people respecting themselves and one another to usher it in. Those of us who are intrapreneurs must continue to brave the frontier.

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