Asking the right questions in the social sector

Questions to accelerate life and work enjoyment
Asking better questions is my new obsession. Asking the right questions  to myself on a regular basis helps me live an examined, all around better life. Asking the best questions in a social sector work setting can accelerate our social impact and overall tranquility. 
Asking questions has always been hard for me. It member in high school and college formulating questions for a teacher or invited speaker then freezing, being unable or only with great discomfort to squeeze out my query. I doubted my thought process, I feared exposing the edges of my understanding.  I worried about opening up to counter questions. While I've confronted most of this work early fear some elements still lurk and I be found that purposeful questions can define projects and your life if wielded well. 

---

Questions are now a deliberate practice that I apply to work and life the social sectors. Here are a few of my favorite questions to apply to social sector work and life. Some are developed from my social sector life/work experience, and some are inspired from the writings of Tim Ferris and Joshua Waitzkin’s The Art of Learning:
Life and Work Questions
What would this look like if it were simple? - Asky why a scenario or problem is complex, and imagine how it would look if the answer or resolution were simple. Use your answer to to reduce complexity and number of steps involved. 
How could I achieve this mission with unlimited resources and the best talent in the world? - Varying assistance budgets and available human experts limits many projects in my field of International humanitarian assistance.  Resources are finite in the wider social sectors and we perceive scarcity in our own personal lives. Break through this assumption and ask how you would solve a problem for yourself or your social sector mission with unlimited funds and a team of top global talent. 
What lies are we telling ourselves? What have I accepted as fact that could be completely or partially wrong? - In my head there are what Ramit Sethi calls “invisible scripts” constantly playing. I’m not good enough, this will never work, I’ll get less of something than someone else. I’ve made efforts to consciously identify these scripts and build in positive scripts to replace these lies. Think about what other assumptions you are making in life and work that you could break with a new thought pattern. 

Asking why three times to surface the root - My six year old son loves to use this approach and I’ve adopted it for myself. Asking why three times on the same issue gets breaks things down to root causes. At the root is often fear. Identifying and confronting these foundational issues can help move thorough social sector work and life blockages. 
Have I really looked listened and understood? - This references Steven Covey's classic habit if first seeking to understand before being understood. This question checks your level of listening, a first step to empathy and designing a better solution for your own routine or your social sector group’s strategy. 
How could I compress this (project, mission, outcome) into half the timeline? One quarter of the timeline? - This question can be out of place in some social sector entities (like national government) where systems can be designed specifically to slow to escape rapid political change around apolitical social goods. However asking how to shorten a timeline can surface new approaches and help you think past a block. 
Applying the beginners mind
My children have it. The lack of fear and playful exploration that gives them to tools for exponential language growth and exploration of new ideas. As adults we need to cultivate the mature version of this early freedom. Asking questions can consciously break through the subconscious fear buzzing in our brains and push us back to an open state where we can experiment, learn and adapt. 
Sanctioning Questions
Many questions go unasked in my specific social sector (international humanitarian response) because we operate in a multi-agency multicultural environment where inclusivity is often valued over clear action.  
This is where diplomacy enters the equation. Finding the line between asking a specific and issue exposing question and alienating the person across the table is possible with the right level of listening and empathy is possible with practice. Being able to probe the edge of provocative and profound comes through testing. We all have to push ourselves to that edge rather than sticking to the easy territory, the well mapped discussion tracks that inevitably lead back to the beginning.
Try these questions on yourself and your social sector team.   
Happy trails!