3 Stretch questions and exploring the unknown

We end the substantive content for the week by thinking about the practice of asking questions in organisations as a way of supporting each other to explore the unknown. Asking questions may seem like an obvious, even basic, skill and yet it is surprising how infrequently enquiry is adopted within organisational settings. Meetings, for example, are usually dominated by people seeking to make a declaratory point (this means that you’re declaring something to be the case, rather than questioning it: the sky is blue; the cat is sitting on the mat, etc.).

Hence meetings can become disjointed affairs, a series of sometimes connected, sometimes disconnected declaratory statements by people. Building on a point, exploring its dimensions, allowing space for something to be explored are things that happen too rarely.

Asking good questions is an essential leadership practice. Such a statement may seem counter-cultural when so much of leadership theorising and practice is wedded to the idea that leaders should be the people who already know – our heroic saviours, if you like. This is an unhealthy way of thinking that restricts the range of ideas and solutions available in the wider organisation. If an important part of leadership is about exploring the unknown (what we don’t know we don’t know), then we will never be able to enter this territory without first asking questions of what we already know and think we don’t know.

Of course, there are helpful questions and less helpful questions. Predominantly, we can think along the lines of open and closed questions. Closed questions can be answered with a ‘yes’, ‘no’ or a ‘maybe’. Their effect, as is hinted at in their title, is to close down a conversation and allow it to cohere around a settled point. For example:

Wouldn’t you agree that given we have only three weeks until we submit this funding bid we really shouldn’t be discussing volunteering strategy at this meeting?

Closed questions can often be declaratory points disguised as questions. These are strategies to close down discussion and debate. Closed questions can sometimes also be provocative, however, and used as a way of getting others to pay attention, although these are minority cases. One response to a closed question might be to fire an open question straight back: ‘Why are you asking that? Have you thought about an alternative approach?’

Open questions are any kind of questions that you cannot answer with ‘yes’, ‘no’ or ‘maybe’. These questions usually begin with a ‘what’, ‘why’ or ‘how’. For example:

  • ‘What do you think about our volunteering strategy?’
  • ‘How do we convince more young people to sign up as volunteers?’
  • ‘Why are you so committed to that particular solution to our volunteering problems?’

Another way of thinking about open questions is that such questions should make you stretch for an answer. Fiona Kennedy, a researcher and leadership development facilitator at the New Zealand Leadership Institute, adopts the metaphor of a rugby match in order to convey this point. A good pass of the ball in rugby is a pass that a player has to run into. As a player catches the ball, new space opens up and momentum develops within the team’s movement. Good stretch questions perform the same function, Kennedy argues.

In what follows we make the case that asking stretch questions is an important leadership practice as it re-shapes conversations in important ways, opens them up to possibility, to explorations into previously unknown territory.

A brief warning, however. We advocate stretch questions here as part of a package of leadership practice. Sometimes the practice of asking questions can get out of hand and groups can get stuck in seemingly endless enquiry – circling but avoiding decisions. Of course, we understand that organisations have to make decisions, sometimes quickly and decisively. That said, overall, not enough questions are asked in organisational practice, so we think the risk of such a practice going overboard is less pronounced than the counter-risk of enquiry being shut down.

2.3 Supporting colleagues in exploring the unknown

4 Stretch questions and wicked problems