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The Role of Empathy and Experimentation in Collaboration

We are excited that today’s blog author will be featured as one of 8 presentations at this year’s Sharing Innovation 2019. Like what you read? Register today at www.nonprofitcenters.org/sharing

Think about the last time you created or joined a collaborative project or partnership. In my most recent experience I felt optimistic, excited, and hopeful. I also felt scared, territorial, and skeptical. My hope was about how the collective skills contributed by each partner would elevate the work, and my fear was about how my organization’s name and my hard work might get lost in the mix. I also felt a bit of distrust with some of the organizations in the room. None of these feelings were outwardly expressed as I sat around the table. What we discussed was the work of each of our organizations and gaps that we saw in our community that perhaps our collective effort could help to address.

While this was a start to identify new or enhanced potential programs, services, etc., I was reminded of the early foundation-building steps that are often missed in a new collaborative effort: empathy and experimentation. Empathy provides the foundation of deep and authentic understanding between collaborative partners and experimentation tests the behaviors you need to see in order to achieve success. What if we asked new questions of one another and what if we held each other accountable in new ways?

Empathy in Collaboration

Empathy is all about walking in the shoes of another person and truly understanding their perspective. We do not often address how each person (and by proxy, organization) might feel about the collaboration, what they fear, what excites them, and what they are wondering about. Imagine if you asked each person in the room to write down on sticky notes the answers to three questions:

  1. What excites you about this collaboration?
  2. What are you feeling fearful or wary about related to this collaboration?
  3. What is the biggest question you have about this collaboration?

These sticky notes can be placed in three bunches on the wall anonymously and then reviewed for all to hear and see. You might hear similar mixed emotions to those that I was feeling, and you might see questions like “Why was I asked to be here?”, “Didn’t we try coming together three years ago?”, or “Who are all of these other people and what do they do?” Can you imagine what kind of meeting you could have if you started with an activity to draw out authenticity and vulnerability vs. diving head first into the work of the partnership? Understanding perspectives and how each collaborative partner feels connected to the group (or not) is paramount to moving forward.

The other opportunity for empathy in collaboration is to understand what even asking someone (and an organization) to collaborate truly means. What does it mean for them to be invited? Is it seen as an honor or as something they have to agree to for political reasons? Does the timing of the collaborative effort gel or create friction with other priorities/challenges/opportunities within their organization? Does this person sent to represent their organization have the power, support or capacity to truly engage in the full partnership? It is almost as if we ask people to attend collaborative meetings and then exist in a vacuum separate from everything else going on in their organization. We lack empathy for the context of what the collaboration means when it is situated within each separate entity. Two helpful questions to ask are:

  1. Outside of this project, what are the key priority areas that your agency is focused on?
  2. What are some of the most significant challenges or opportunities that you are tackling currently as an organization?

Knowing the answers to these questions is key because if there is turmoil within leadership of an agency, or huge growth in another, this will impact how the organization show ups and participates, ultimately impacting the success of the collaboration. Powerful and effective collaboration is driven by authenticity, transparency and connection. Collaboration should not only be focused on how we best leverage assets and super powers, but ultimately how we meet people where they are and create mutual value. People will not participate fully in activities or solutions that do not create value or solve problems for them. We can’t create collaborations that benefit all partners until we understand their needs, wants, fears, perspectives, and context, and that is the power of empathy and asking new questions.

Experimentation in Collaboration

We often do not test drive potential collaborations before we put them into action. This may be due to crunch time to get quick letters of support added to a grant application on time, but more often than not, we have no mechanisms to test the say vs. do and assumptions embedded within collaboration.

Unfortunately untested assumptions can be lethal to collaboration. We have seen entire partnerships crumble (the reasons why only to be uncovered years later after much wasted time, effort, and resources) because no one tested the initial assumptions of the collaborative work itself. Everyone agreed to the vision, goals, structure, and activities but those agreements slowly and silently broke apart and the program failed.

Assumptions are all the things that must be true about your partners for the collaboration to be successful, and they are often things we assume are true without any evidence. “Of course your partners refer clients to your program, advertise your services, attend a majority of partnership meetings, share data, contribute to shared grant applications, provide staff or volunteers to support a program, provide space for programming, share financial resources, etc.”

Within every potential opportunity there are two kinds of assumptions to consider:

  • “Technical feasibility” assumptions: Do they have the infrastructure and support to contribute to the collaboration?, If a partner does not have the infrastructure or capacity to fully support an initiative, they will not be able to fully engage.
  • “Market feasibility” assumptions: Do they have enough skin in the game and value involved for them to participate? If the partnership feels like additional work, for very little financial reward and recognition, it will be very difficult to get the attention and full cooperation of an agency because this will fall below their priority list.

The good news is that there are small, early, and simple ways to test all of these assumptions.

For example, if your collaboration requires data sharing, assumptions might include:

  •  The partner has the data you need.
  • The partner is willing to share the data.
  • The partner has permission to share the data.
  • The partner knows how to access and package the data to be shared.

As an experiment, you could ask the partner to supply you with a “lower hurdle” or more simple request, such as a list of anonymous participation numbers or feedback reports from their latest program evaluation. If you receive the data, you have tested all of the above assumptions as well as learned how long it takes to get the data, how the communication flowed in the request, the clarity or completion of the data, etc. If the data never arrives, it is very important to try to establish why it did not occur. This is not a time to create more assumptions as to why the task fell through the cracks. You need to understand if it was a break down in any of the above elements, or something else. Partners will show you their level of buy-in with the actions they take, so test and trust behavior, not words, to see how you can actually create impact together.

In addition to testing assumptions of the actions required as a collaborative partner, one powerful initial experiment you can run, which also engages empathy, is to see if your collaborative partner is willing to answer the 20 questions below. These questions were born from the frustration that we have felt, seen, and heard working in organizations and they can be game changing if asked early and often. By asking these questions, you are testing the assumption that your collaborative partner is willing to engage in authentic, transparent, and collaborative conversation. If they agree, hooray! If not, you may be gaining some foresight into experiences and outcomes to follow.

Top twenty questions to ask your collaborative partner:

  1. Why are we here? What is the opportunity?
  2. What are the vision and the intended outcomes?
  3. Why was my organization asked to be here?
  4. How have our separate organizations addressed this issue in the past?
  5. What work have we done together in the past?
  6. How was I selected to represent my organization?
  7. What are you looking for each person to provide?
  8. How much time do you estimate my organization and I will have to dedicate to this project?
  9. What are the financial resources for this project? What are the total dollar amounts?
  10. How will money be distributed from this grant and how will this be divided among the partners?
  11. How will my organization be recognized for our contributions to the program?
  12. Will my organization be able to present our own individual data and experience to the funder directly?
  13. How will my agency provide feedback about the success of the collaboration and the functionality of our partnership?
  14. Outside of this project, what are the key priority areas that your agency is focused on?
  15. What are some of the most significant challenges and opportunities that you are tackling currently as an organization?
  16. What are some elements about this collaboration that make you the most nervous or of which you are the most concerned about impacting the success?
  17. What have you experienced in the past with other agencies that has generated successful collaborative work?
  18. What have you experienced in the past that did not work well for collaboration and led to disappointing results?
  19. What must be true for this to be a successful collaboration? In other words, what assumptions might we be making about our work together that could make or break our ability to reach our vision of success?
  20. What are some ground rules that are really important to your organization and us working together?

There are myriad layers of complexity when individuals, teams, and organizations work together. Empathy and experimentation are two tools that are often overlooked, but extremely powerful to creating powerful, sustainable, collaborative change.

To learn more and watch Heather’s presentation about Empathy and Experimentation in Collaboration, register to attend the Sharing Innovation conference in person or via live stream October 10th.

About Our Blogger:

Heather Hiscox, Pause for Change, Tucson, AZ

Heather Hiscox is a social entrepreneur passionate about creating communities focused on assets, abilities, and abundance. She is the Co-Founder of Pause for Change, a company that helps nonprofit, philanthropic, and local government organizations learn a new way to change the world. Heather is also the creator of Wish List Hero.org, a website that publishes the greatest wishes of nonprofits each week in the Arizona Daily Star. Heather is a Lean In Regional Leader and co-founder of the Women of Purpose Chapter. She has received numerous awards for her leadership and commitment to the community, including University of Arizona Honors College Young Alumna, TEDx Starr Pass Women Local Leader, Greater Tucson Leadership Ronald L. Kurth Award, 40 Under 40, and Inside Tucson Business Up and Comer.


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