How to Ask Great Questions

In strategic planning, one of the most important events happens right up front – framing a set of relevant, purposeful, interesting questions that will inform your actions or critical decision-making. Many organizations approach this moment as an opportunity to ask routine questions, such as “how can we be better known?” or “how should we grow?” We don’t mean to say these are bad or wrong questions – quite the contrary – there are always questions to ask around how to do better or more. But to really take advantage of the benefit of strategic planning, you should view it as a moment to step back and and ask yourselves existential questions – literally. The rest of the strategic planning process hinges on the clarity and quality of these questions.

Guidelines for framing great questions

So a few guidelines for making sure you’re asking the best questions:

Are the right people asking the questions?

Make sure your board has weighed in on helping to frame these important questions – you can help to ensure they are thinking strategically so you can make the most of your strategic plan.


Using the rigor of this question to guide your framing of strategic questions will help ensure you focus on the questions that are most important, most pressing, and most relevant to your work.


What will you do with the answer to these questions – how will you be able to use that information to inform your approach to the work, adapt or change your approach, or make important decisions along the way.

Try asking yourselves the following questions:

Why do we exist? 

You probably have a strong sense of the answer – to address poverty, to produce new artistic works, to protect our natural resources. But stay in questioning mode a little longer – how has the need for your organization shifted or changed over the years you’ve been in existence? How will it be shifting or changing in the next 100 years? If you were starting your organization from scratch today, what would you do and why? You might find that after researching these trends, you shift the way you think about what it takes to address the need your organization was created to address.

What models from other fields could be applied to our field as a new approach?

How often do you question your entire approach to what you do? How do you know that is the best approach? We are often told to measure outcomes – and we appreciate how hard that is to do really well – but what do those outcomes tell you? Are you knocking it out of the park? If not, this question may help you reevaluate your approach.

What is the persistent problem no one has solved in our field?

Why has no one solved it (including you)? Is it too big a problem for any one organization to solve? If so, what kinds of partnerships or alliances would increase your impact on the problem? Are there leading indicators that predict this problem on which you could have an effect? How can you break down the persistent problem into manageable bites that you can measure along the way to understand their influence on the larger issue?

What are the consequences of doing nothing?

Why do we need to change? What is driving that – is it a shift in the need, is it a shift in the funding environment? This is a great question to ask when you’ve framed your strategic questions to vet how pressing or important they are.

These are not easy questions to answer. You need to spend time listening to a range of opinions and engaging key stakeholders in the process. You’d be amazed how much their input will help you answer these tough questions.

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