All the right questions, just not in the right order

In the first phase of strategy processes, an interesting thing happens. It turns out that in most organisations people have been sitting on questions, sometimes for many years. They have been waiting – sometimes patiently, sometimes with growing frustration – for the right time to ask these questions. And then along comes a strategy review and a surprising amount are raised.

We respond by gathering every single one of these questions together, so that everyone knows that their questions have been heard. When we step back, we see the same pattern: people have been asking all the right questions, just not in the right order.

The problem is that, if you don’t pay attention to the order in which you answer questions, conversations go round in circles - never finding a resolution. For example, we worked with an organisation which had circled many times around the issue of which languages to use in its materials. Stepping back, they recognised that answering this question depended on the question of which key audiences and stakeholders they wanted to engage. This was not a simple question: they had diverse stakeholder groups spread across the globe but by answering this first order question, the issue of language was much more easily resolved.

If you get a sense of ground-hog day, circling around but never quite answering questions, here are some things you can try.


  1. Generate

    Start by generating all the questions that you think need answering through the strategy process. Make sure that you ask open questions (when, where, what, who, why, how) rather than closed questions that can be answered with a yes or a no. For example, “Should we develop a more targeted membership offer?” will illicit a narrow response but “How do we target our offer so it better meets the needs of new members?” opens up an important conversation. And beware the temptation of turning an opinion into a question! For example, “Should we look again at the fundraising capabilities in our organisation?” is really a coded way of saying “I think we should look again at our fundraising capabilities.”

  2. Reflect

    Now that the questions are out of people’s heads and on paper, take a moment to reflect. Spot where there are multiple questions around the same issue – these are often areas that have been difficult to resolve or are causing real operational difficulty. When you look afresh at your list, think about what you have missed. Often with the first wave of questions out on paper a next round of even deeper questions will begin to emerge.

  3. Cluster

    Cluster the questions by theme. And try for no more than six themes. This should show you the big areas of concern across the organisation. If there are outliers, that’s fine as odd and left field questions are often helpful too.

  4. Find the biggest questions

    Here comes the tricky bit – now that you have all the questions generated you need to identify the biggest or first order questions. When we work with clients at this stage we often use the metaphor of nesting dolls – first order questions are the grandmother dolls, the biggest questions that unlock or give direction to a series of smaller, tactical or operational questions. For example, you can only answer the question of whether or not you should respond to a particular government consultation when you have settled on how much resource you want to invest in national policy campaigning in your organisation.

  5. Pencil in an answer to these big questions first

    Having identified three or four first order questions, your job is to pencil in an answer. We use the metaphor “pencil in” as these big questions can feel overwhelming, and any answer may feel too small or unsophisticated by comparison. But the job here is to use what you know already and work at pace. For example, setting a 15 minute time limit on your first draft is one way of avoiding the “perfect becoming the enemy of the good”.

  6. Pencil in an answer to three or four smaller questions

    Using the same working-at-pace techniques, drop down a level and pencil in an answer for three or four of the second order questions, making reference to your answers above.

  7. Review and repeat

    With these roughed out answers in hand, step back and review. What’s working? What’s missing? Repeat the process two or three times to refine and clarify. You can reorder or re-cluster questions as you create more clarity about your direction.


If you are feeling stuck with questions big or small in your organisation, having an independent set of eyes and ears can really help. Let us know where you are on your strategy journey.

BlogKatherine Rake