Holding Dilemmas Together in the Workplace: A Sneak Preview of the Future

by Miki Kashtan

Throughout human history, stories have been a source of inspiration and bonding. Especially in these difficult times, when we need inspiration about what’s possible, when so many of us are hungry for some faith that collaboration can work, I feel so happy to have some examples that nourish me in my own work. This is, simply, about what work can be like when we embrace a deep intentionality of collaboration.  (These are three real-life stories, two of which are changed in non-substantial ways to protect anonymity.) They all exhibit the path I think of as inviting people to hold a dilemma together. I have written about this path in other contexts, and I am truly delighted to share something that can offer a visceral sense of what the future could look like, however small the scale.

A Hiring Challenge

A colleague of mine, let’s call her Jennifer, was in the process of hiring an administrator. In the process of interviewing people, one candidate, named here Susan, stood out as being an absolute fit for the scope and quality of the job. The only catch was that Susan wanted significantly more money than Jennifer’s budget; more, in fact, than Jennifer herself was earning. She approached me, initially, to get a sense of what people at BayNVC were getting paid, to help her assess how to respond. After some back and forth, what stood out to me was that she was going to make the decision by herself, without involving Susan. Whatever course of action she was going to take – accepting what Susan asked for, turning down the offer, or negotiating with Susan about a lower pay – all of that was going to be inside of Jennifer. In this, our familiar and common world, she would be operating separately from Susan, and Susan from Jennifer. Each would decide for herself what works for her.

Here’s what I said in a final email: “Does she know she will be making more than you? Are the reasons for the ‘minimum’ she wants about sustainability or about dignity/value? Dialogue with her, invite her into the dilemma, make a decision with her.”

This idea – inviting people into the dilemma – is one I am more and more drawn into. It’s one of the ways that I see myself supporting people to embrace collaboration. It’s revolutionary in its simplicity, and in general doesn’t occur to people. Most often, when I find a specific enough application, people welcome and embrace it – whether parents or bosses. In this case, with Jennifer being an NVC trainer, she was very happy to experiment, and invited Susan to have a conversation.

And what was the outcome? After their conversation, Susan said this: “I was particularly impressed by being ‘invited into the dilemma.’ It’s an excellent example of the kind of open communication and collaboration that I strongly value and that draws me to the work you do!”

Jennifer told me that the invitation allowed for a heart opening and immediate sense of partnership and mutuality. It helped Susan to see and hold Jennifer’s needs alongside her own, and it moved the conversation into much more of an interdependent process.

The conversation also allowed Jennifer to understand why Susan was asking for the amount of money she wanted. Rather than thinking of it as ‘high pay,’ it allowed Jennifer to understand Susan’s need for security and sustainability and it opened the door to look at other possible solutions. They both agreed to take some time to see how far they could stretch and to make room for creative ideas to emerge.

This created a total shift – the kind of shift that is at the heart of collaborative problem solving – the shift I call “from conflict to dilemma.” Instead of “negotiation,” this kind of exchange moves into emotional, practical, and more than anything mutual “engineering” of a solution together. Everyone is working on the same issue from the same direction. Regardless of the outcome, the key is the invitation. Now both parties can work in partnership to solve the puzzle.

In this case, they didn’t find a way for Susan to take the job. As it turned out, the very day that they were having the conversation, Susan’s familial circumstances changed to such a degree that her capacity to stretch, which she would have been “willing and happy” to do, in her words, was totally compromised for external reasons. Nonetheless, she expressed a desire to continue to aim for ways to collaborate, and is now volunteering a few hours a month in support of Jennifer’s work.

In the world of the future, and I see it as a possibility in the current world, with only minimal tweaking, as in this case, I see the process of “job application” as potentially instructive and collaborative rather than transactional. Of course some people are completely not a fit. However, what if we have a few candidates that are potentially a fit? How much more satisfying could it be, even if scary, if the finalists would all get together with the hiring committee and engage in a collaborative approach to identifying the best fit?

A Performance Challenge

This one is from my own experience of managing staff. These days, I am ecstatically happy to have three people who work, part time, to support my work in the world. Aside from the great delight of having, for the first time that I can remember, adequate support, I am overjoyed to have my own little “lab” in which I can put to use all of my ideas about collaborative leadership. I have a lot to say about collaborative leadership in the context of my explorations about what power-with does or doesn’t mean, and I am planning to come back to this exploration soon. For now, suffice it to say that collaborative leadership is not the same as radical equality. The purpose of our coming together as a team is clearly stated as being in support of my work and my vision – this is what drew these people to want to work with me. In the context of that, we are in full collaboration, and more and more so by the day. I am asking the people on the team, for example, to be the ones to engage with the difficult task of deciding what makes sense for me to take on and what they would recommend I say “no” to. I ask for their input on just about everything significant, and receive wisdom I wish any leader could have access to. In my work with organizations I mourn, in fact, how often I hear this kind of wisdom behind closed doors, wisdom that never makes it to the executive leadership, to everyone’s loss.

Within this rosy-looking picture, I was having a growing sense of anxiety about the level of administrative support I was receiving from one of them (this is being written with her consent). I was feeling a lot of stress, because I couldn’t ask for a better attitude, and yet some of the work wasn’t getting done in a way that supported me.

She is committed to supporting me in ways that move me to tears at times. She is open to receiving feedback without anything I can associate with the word “defensive”. She has immense flexibility in terms of what tasks she is willing to do and when, and expresses her joy about doing this work, and her sense of inspiration about what I do and how I do it, consistently. She is also applying herself to learning the content of what I teach, and has wholeheartedly joined my immersion program. At the same time, details were not being tracked, tasks were not completed when I was expecting them, I had to look at what she did before she submitted it and would regularly discover errors, and I felt anxious about not being able to release my own responsibility, the very reason for which I hired her.

Initially, I hadn’t crossed the line into the collaborative world. While we talked openly about the issues, I still somehow saw it as my problem to solve. Then, one day, while talking to a friend about my hopelessness about the situation, I suddenly woke up. All I needed to do was to bring this to the team as a whole, and we would hold it together. Almost immediately my stress level declined. At our next staff meeting, I brought the dilemma to the group in exactly the same way I described it above.

It’s hard for me to describe the experience of what ensued. The sense of being together, of dissolving the habitual separation, of leaving behind the idea of “boss” and “employee” and embracing the radical image of complete partnership within the team to find ways of supporting her and supporting me – all of this was almost intoxicating. Not easy, because the topics were painful. Still, exciting, meaningful, and hopeful. Within about fifteen minutes we lined up a bunch of strategies – some changes I was going to make in how I explained tasks and asked for them; some changes in how we communicate with each other; some places where fear interfered with communication and where we created structures that would support this person in speaking up when she was beyond capacity, and seek support to fulfill her tasks, or give them back to me; and more availability from the other two people to support her with areas that are harder for her. This happened a few weeks ago, and the results are dramatic. There is joy, there is flow, even more of a sense of collaboration, and, alongside that, more productivity and clarity in the outcome. Work is, after all, not just or even primarily about how we feel… it is, first and foremost, about attending to the responsibilities we have agreed to as part of our job as efficiently as possible and with high integrity. All of that is happening now more than before.

A Funding Challenge

One of the people I coach is a funder, let’s call him Carl. From time to time Carl comes to me with specific dilemmas that he encounters in dealing with people – both those he funds and those who are in positions of influence surrounding the funding itself. I am learning a lot from these exchanges about how power and leadership work, and I am also delighted by Carl’s capacity to integrate the deep tools of collaboration into the work he does as a funder.

Recently, I was telling him about this approach, the invitation into a dilemma, and we discussed how this would apply in the grant-making world that he inhabits. I was thrilled to hear of an example where he intuitively applied this path.

An innovator approached Carl with a request for funding for a new project. Carl was impressed with the ideas and told them he was favorably inclined to offer them the grant and would get back to them soon to work out more specifics. In a conversation with a colleague of his, he casually mentioned this project, and was astonished to receive a strong admonition not to fund their project. His colleague, so Carl told me, said that while the ideas were great, the innovator didn’t have any plan of action, and any money given to him would be thrown away.

Carl then told me that he instantly saw how much he has grown since embracing the principles of collaboration. In the past, what he would have done in a moment like this would have been to back out of his semi-commitment to the innovator, a practice that at some points in the past ruffled many feathers around him. Now, he chose, instead, to approach the innovator with full transparency and, as in the other examples, invite him into the dilemma. He explained to him his concerns and what he had heard about their project, and invited a brainstorming to see what they could do together.

Despite his growing satisfaction with the results of collaboration, he was surprised to see the outcome. The innovator, after an initial disappointment, became much more forthcoming about the struggles he was having. Instead of a large grant for a project that was not yet formed sufficiently, they both saw an immediate next step – a much smaller grant coupled with a referral to a consultant who would help in formulating a clear plan for the project. Carl and the innovator both saw how much more benefit this would bring to everyone, including the future beneficiaries from the innovation itself.

These are three examples of what can happen when we work with people to address complex, seemingly intractable issues around which we tend to act in isolation. Our times are such that these capacities are essential. I believe the stakes are high, and constantly getting higher. The future of our species depends on this kind of active interdependence. If we don’t align our practices with the reality of how interdependent we are, the level of alienation we live in, combined with our rates of consumption, will continue to exacerbate the stress on all of our life support systems. We really are all in this together. Let’s act on that clarity.

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