20 Questions for Complex Problem Solving & Strategy Development

A practical guide for solving complex problems & developing strategies for complex challenges

Build a deep understanding of the situation, so you can be informed about what to do, instead of having to guess

1 Clarity on the problem and desired outcomes

What is the issue? And what is the outcome you want?

2 Context, Constraints and Requirements

What are the political and policy context and constraints? What do you want the new system to do?

3  Knowns, unknowns and a planned approach

What do you know and what do you need to find out?

4 Understanding the problem

What is the scale and nature of the issue? How has it been changing? Why is it occurring?

5 Never miss an opportunity to learn and gain insight

Really?, Why?, What’s the ‘so what’?

Re-design the system & rigorously think ideas through, to achieve the outcomes you want effectively and efficiently, and to anticipate the unintended consequences

6 Think analytically

What structural changes to the system design could change the outcomes?

7  Think creatively

If we think about the problem and solution from different angles, what new and useful ideas and insights emerge?

8 Goal Design

Have the goals, targets, KPIs and incentive structures been designed so they don’t distort the system?

9  Assumptions and Necessary Conditions

What assumptions have you implicitly and explicitly made, and are they being tested along the way? What conditions need to be in place for the strategy to work?

10 People and Behavioural insights

What factors influence what people think and do in this context? What unconscious biases might be influencing ourselves and others?

11 Consequences and Trade-offs 

How could this idea play out? What are the costs, benefits, flow-on effects and possible unintended consequences?  What are the trade-offs?


12 Integration and Implementation

How will this work in practice? What needs to be done to put it into practice?

13 Evaluation, Experimentation & Knowledge-sharing

How will you determine what works and what doesn’t?

Take an evidence-based approach, so you have a strong case for, and confidence that your ideas will work

14 Strategy Logic

How will the things you plan to do lead to the changes you want?

15 Policy rationale 

What are the reasons for thinking the strategy will work? What are the counter-arguments? Is the reasoning sound?

16 Data & Information

What information supports (and contests) the reasons for thinking the ideas will work? Is it sound?

Learn and adapt, so the strategy maintains its relevance in a dynamic, uncertain world

17  Learning & adaptive design

What’s the best idea you currently have?  How will it adapt to things that change and to what we learn along the way?

18 Agility, Resilience and Innovation

What might happen in the future that could impact this work?  How will your ideas be resilient to threats and ready for opportunities?

Engage Others, to inform, test and build support for your ideas

19 Interdisciplinary perspectives

What are the interdisciplinary views and why do people hold those views?  How can we have purposeful conversations in contested and collaborative contexts?

20 Compelling communication

Are we explaining our ideas so they are understood by, and resonate with others?

This is how the 20 Questions are intended to be used:

  • Use the 20 Questions as a checklist or guide.  The 20 Questions (and practical techniques to help answer them) can be used as a toolkit (draw on the one that’s relevant to what you are doing at a particular point in time), but, they are most useful as a package deal.  Either use them as a checklist to ensure you’ve thought about everything you should, or, better still as a guide for systematically (but iteratively) developing a thoroughly thought-through strategy.  A strategy document could even be structured into 20 sections grouped into 5 parts.
  • Prompt your thinking.  The 20 Questions don’t provide you with answers, or do the thinking for you.  Rather they prompt you for what needs to be thought about. The techniques help you do that thinking.
  • Iterative and adaptive.  Despite the 20 questions appearing in a sequential list, they are intended to be asked over and over again, iteratively, throughout a strategy design and implementation process.  This may be over the course of years.  The questions stay the same – it is the answers to the questions that evolve over time as things change and as we learn from testing our ideas.
  • Use them for any endeavour.  The 20 Questions are versatile and flexible because they can be used when planning a strategy or approach for just about anything – public sector (from small tasks to large cross-cutting taskforces), private sector, even our personal lives.  The specific details for particular contexts come through in the emphasis you decide is appropriate to give to each question, and, the answers.
  • Use them throughout the policy development cycle.  The 20 Questions are the same questions you ask on the first day right through to the last day you are considering a strategy.  What changes, is the emphasis you give to the questions, and, the answers.
  • Anyone can ask the questions.  The 20 Questions can be asked by anyone, of anyone and that’s where much of their potential lies.  Citizens in an electorate can ask them of their government representatives.  Elected public officials can ask their Ministers, Ministers can ask their public service departments, and departments can ask them of their policy staff.  In this way they encourage more accountable, deeper and deliberative policy discussion.
  • Ask them in no particular order, and concurrently where possible.  While the order given is a very general guide, in practice, the order will be much ‘messier’.  Questions should be asked concurrently – and some, for example questions 5 and 19, should be asked in conjunction with every other question.  Generally speaking, the earlier questions would get most attention early in a strategy design process and the latter ones would receive more attention later in the process, but all questions should be asked and re-visited throughout.

Click here for a downloadable and printable version of

20 Questions for complex problem solving and strategy development

Attend our seminars and workshops to learn the practical techniques to help answer them

Our seminar series and workshops build capabilities across all these essential elements of problem-solving and policy and strategy design.  Download the seminar series and workshop flyer for more information.

Higher-order thinking

Embedded in the 20 Questions are eight valuable higher-order thinking styles, including strategic thinking, systems thinking, design thinking, creative thinking, critical thinking, structured thinking, analytical and futures thinking.