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Asking Hard Questions, Softly—but Persistently: a Key Skill in Collaboration

The views expressed are those of the author and do not necessarily reflect the views of ASPA as an organization.

By Larisa Owen
January 16, 2020

Collaborative efforts demand trust that partners will share resources in working toward shared goals. Many collaboratives meet often, but without getting their disagreements about values on the table. That gap can undermine the trust needed for collaboration that is more than just operating a joint project with someone else’s money.

Bringing up issues about values can build trust if done skillfully, using a guideline of, “Hard questions, asked softly and persistently.” Those values disagreements can include:

  • Who are our clients: children, parents, single individuals, the very young, adolescents, single parents? A case can be made for each of these, but choices are often avoided by organizing a program so it is more accepting of some clients than others.
  • What is the agency’s responsibility and what is the clients’ responsibility? If clients must make reasonable efforts to enter and comply with treatment guidelines, or to parent their children better—what is the agency’s responsibility to make reasonable efforts to help clients with cognitive disabilities, trauma history or other barriers to seeking and remaining in treatment?
  • Whose resources should be used? An agency with less funding may resist partnerships in which collaboration sounds like, “Let’s you and I collaborate with your money.”

The role of leaders in collaboratives, aided by external providers of technical assistance and training, is to ask questions that surface these disagreements. A key skill is listening for what collaborative partnerships don’t discuss when these kinds of issues are kept off the agenda or shifted off to a subcommittee that rarely meets. Sensing what is not being discussed is also a key skill. Like all humans, project staff acquire skills in avoidance, denial and deliberate misdirection. Detecting that isn’t technical—it’s intuitive and forensic; seeing what is and isn’t happening and what results from that gap.

Some of those questions are:

  • Who is entering our program and who is not, or is dropping out? Which clients are having trouble accessing our program or engaging with our staff—and why?
  • If our program works better than current practices, why is it just a project? If it’s better, why isn’t it bigger?
  • If we’ve added new components to our programs to make them work better—what are the true costs of the program now? Without new or redirected funding, does that mean we will serve fewer clients?

The persistence part of asking hard question is to recognize that leaders and outsiders both may encounter resistance when they first raise a difficult issue. They need to understand when to set the issue aside in order to bring it up at a riper moment or with more support within the partnership. Keeping an item on the agenda, even if it gets deferred to a future meeting, is a visible reminder that the problem isn’t going away. If the issue is who isn’t getting services or why outcomes are restricted to a small group, a visible dashboard or regular review of services data may be able to frame issues graphically in ways that will keep them in front of a group of partners.

So how can you be truly helpful? Listening is crucial and a careful blending of patience and persistence is essential. Learning to ask good questions is a key skill, but understanding that you have to earn the right to ask those questions is a precursor to useful intervention. And the distance between asking a useful question and becoming a pest can be hard to gauge.

How to Frame the Hard Questions

Sometimes that question can be framed graphically for more visual learners, as seen in the power of a graphic. Sometimes a data presentation can be deepened by asking what is the most important data we don’t yet have. Hard questions also clarify that as leaders or advisor/outsiders, we are not acting as if we have the answers, easily imported from other projects and sites. Instead, we are helping to frame questions that may not yet have come into view. Some of these are really, “Iceberg issues,” where what matters most is what’s beneath the surface—the missing pieces, the invisible clients who get screened out or drop out, the equity and stigma issues that are always in the background and often missing from the data on intake or the dropout numbers. Focusing on the number of clients that enrolled rather than asking if the clients improved as a result of agencies service can create that uncomfortable friction within collaboratives.

Sometimes asking front-line staff who are face-to-face with, “The customers,” helps make the issue concrete. Bringing front-line staff into a policy or leadership meeting can give hard, previously unasked questions a human face with the credibility of direct experience in daily contacts with those we are trying to help.

Asking hard questions in the right tone, at the right time, can be a leadership contribution that moves an interagency group from just meetings to genuine impact.Allowing those issues to drift away or be continuously postponed may keep a collaborative from achieving the impact it was originally formed to make happen.


Larisa Owen, Ph.D., M.B.A. [email protected]

Dr. Owen is a Program Director with Children and Family Futures.  Dr. Owen works on several project including leading the Veterans and Military Families (VMF) projects within the organization, including planning and implementation of veterans treatment courts (VTC) evaluation and technical assistance involving families in the VTC.  Dr. Owen has extensive experience evaluating the effectiveness of program implementation, program enhancement, and evaluation methods for state and national programs including training and evaluation of collaborative programs. Dr. Owen received her Bachelor of Science in Criminology and Legal Studies, holds a Master’s degree in Business Administration, and has a Ph.D. in Public Policy and Law.

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