
For some reason, there is a pervasive belief that people and organizations know how to engage in cross-sector collaborations. As my colleague Chris Thompson likes to remind me, in 2006, the the Council on Competitiveness aptly described cross-sector collaboration as an "unnatural act among non-consenting adults." The definition of cross-sector collaboration that I prefer is an alliance of organizations that together have a role in solving a problem and achieving a shared goal. Whichever definition you are using, hopefully we can agree that collaborating outside traditional organizational structures of authority and accountability is not how most individuals are trained or institutions are structured to work.
So, why does the myth persist that organizations and their representatives who participate in collaborations know how to effectively engage in cross-sector collaboration? And why do many funders continue to invest in collaborations, but often forego investing in the skills, capacities, structures, and processes of the collaborators?
I wish I knew. Instead, I'm going to share what I do know -- 4 questions to ask when engaging in cross-sector collaboration.
1. Does this problem require cross-sector collaboration?
In The Practice of Adaptive Leadership, Ronald Heifetz and his colleagues assert that the most common mistake practitioners make is failing to understand what type of problem they are tackling – one that’s technical or adaptive. Technical problems have known solutions, individually we may not know how to solve them, but someone does have that expertise and it can be acquired. Adaptive problems don’t have known solutions, they are complex (created by the interaction of many people, institutions, policies, practices and mindsets) and the solutions can’t be identified in advance, but only through learning. Since these problems are created by the actions of many individuals and institutions, sometimes unwittingly, they require many actors working together to change them. So, there’s no reason to form a cross-sector collaboration to tackle a technical problem, but for the adaptive challenges there is likely no other way.

Source: Restoring Sanctuary: A New Operating System for Trauma-Informed Systems of Care
2. Is this cross-sector collaboration set up “right” to achieve success?
Put another way, are the “right” institutions and representatives participating in the cross-sector collaboration to be able to solve your problem? Part of the reason I shared a specific definition of cross-sector collaboration in the introduction to this post is because the term is often used to describe an array of activities involving representatives from multiple sectors. They’ve been lumped together not because of their structures, strategies, or goals, but rather because of who is involved with them. As I wrote in the What Barriers? Insights on Solving Problems through Cross-Sector Partnerships research I worked on at Living Cities:
"this view of cross-sector partnerships is problematic because it does not recognize the variability contained within each sector. For instance, by lumping business together it assumes homogeneity between the interests of organizations that range from small, local businesses and large international corporations. This simply is not true.
We offer a different way to think about the membership of cross-sector [collaboration]s which we have named the interest-based frame. The interest-based frame highlights that virtually all sectors have multiple interests when it comes to solving complex social and economic challenges.
The interest-based approach reveals that instead of identifying one government representative to participate in a partnership, it may require multiple representatives in government who are involved with and can speak to different parts of the work-- policymaking, training and funding in the example above. In addition, this approach helps members of [collaborations] understand their roles, bring their expertise to the table, while preventing individuals from feeling like they have to represent the viewpoint of an entire sector."

Source: Living Cities
Once you have the "right" players at the table (recognizing that may evolve as the work does), the work will turn to you shaping a shared understanding of your goals and charge, how decisions get made, what structures you need to establish, as well as developing trust-building and learning behaviors as a team of collaborators. This is no small feat, and it's no wonder so many cross-sector collaborations aren't able to achieve measureable impact.
3. Does my organization have the capacity, structureS, and culture that will allow us to collaborate effectively?
In addition to considering the external positioning of an organization to engage in a cross-sector collaboration given the adaptive challenge that the collaboration is seeking to address, it’s also important to consider the institution’s internal structure, culture, and capacity to collaborate. I’m a big fan of the work that the UK’s The Partnering Initiative has done on this topic and they’ve created some handy tools to enable organizations to self-assess if they are ready to participate in a cross-sector collaboration through their Fit for Partnering Framework. The Framework identifies key elements of leadership & strategy, systems and processes, skills & support, and partnering culture that should be in place before an institution commits to partnering. This is also a useful tool for funders and technical assistance providers who are working with organizations engaged in cross-sector collaborations.

Source: The Partnering Initiative
4. Does our organizational representative have the necessary cross-sector leadership skills?
Just as organizations need to have developed the capacity to collaborate, so do the individuals who are representing them within the cross-sector collaborations. While many individuals are recruited or assigned to represent an organization in a cross-sector collaboration because of their issue expertise, there are a range of factors that influence a representative’s effectiveness including their personal leadership capacity, cross-sector leadership skills, and level of authority, power, and influence to make change in their home institution.

Source: Presidio Institute