Lead With Questions

Last week, I was reminded of the awesome, and underutilised power of leading with questions.

Questions Leverage.001

A colleague and I spent two days together with a group of up-and-coming leaders. They’re an energised, talented group, hungry to learn and to make an impact on their organisation. A joy to work with.

As facilitators, my colleague and I had a bunch of ideas for what we could have done with them over those two days.We had a run plan. There were certain leadership topics we thought we’d cover with them, and we had the content and activities ready to go.

And, we chose to lead things off with some questions. Questions that we thought would stimulate thinking, connection, and insight. So in the morning session of the first day, we kicked off with this slide:

Workshop Framing QuestionsNow, we thought these might take us an hour to discuss. We spent over two. The conversation was rich, unhurried and thought-provoking. You could feel the engagement in the room. The organisation had been going through a tough few months, and we soon realised that the group had a strong need to make sense of what was going on. If we’d tried to rush it and stick to the run plan, I think we’d have lost the group. Anything we’d tried to teach or tell them would have washed over them. They weren’t ready to engage with new content just yet.

We followed that first slide with this one:

Workshop Framing Questions 2


These questions caused a shift in focus from ‘out there’ (environment) to ‘in here’ (self). There was a quieter, more reflective mood in the room, with the conversation unearthing what was most important for people to work on in their leadership. Leading up to lunch, the group were grounded, oriented to the future, and ready to do work together.

After lunch, we framed the rest of our time together with this slide:

Workshop Framing Questions 4

From that point, we were away. Everything we did came back to that question. We covered lots of territory, including leadership culture, leadership networks, deep listening, uncovering assumptions, and influence. My colleague and I taught some stuff, but mostly the leaders learned from each other. By the end of our time together, this diverse group had a) real ownership for leading a range of organisational issues, and b) developed deep connection and support across the group to make it happen. The catalyst was a handful of deliberate, thought-provoking questions.

So what’s this all about?

I’ve noticed that most leaders (and trainers, for that matter) generally still live in a world of ‘tell’. The need to have the answers, be the expert, show the way. Setting the agenda and driving through the “stuff”. That’s fine in some contexts, like when the answers are obvious, or you can rely on what worked in the past to work in the future. But of course, that’s increasingly unlikely when you’re expected to lead in a world where old blueprints need to be thrown out and new approaches invented. As I’ve written about before, we need a more curious approach.

In this context, there’s huge power in letting go of the need to tell, and instead shifting to asking questions. This requires a reframing of what it means to be a leader. A move away from being ego-centric. A move to towards other-centric (whether ‘other’ be another person, group or the system you’re in).

Here are some ideas about how you can lead with questions:

  1. Determine your intent. What is it that you want to occur during the conversation, and afterwards? I find it useful to break it down into “Think, Feel, Do”. What do you want people to think about? What do you want them to feel? What would you love to see them do?” Your answers to these questions will shape everything that follows.
  2. Frame your role. Imagine two roles: Teller and Asker. Given your intent, what percentage of your time do you think you need to spend in each? Hint: allow more time for asking than you’re comfortable with.
  3. Decide on the questions. These, of course, will depend on your intent. I find powerful questions have the following in common:
  • You can’t possibly know the answer beforehand (so you have to be the “naive inquirer”)
  • They’re not easy to answer
  • They raise awareness
  • The provide a focal point
  • They generate possibility
  • They generate responsibility and ownership
  • They tend to start with ‘What’, ‘How’ or ‘Why’

Notice how the examples above have some or all of these elements.

So, here’s a challenge for you: over the next week, pay attention to how often you choose to lead with questions versus “telling”. Perhaps get yourself a ‘spotter’ to give you feedback on how you’re doing. When you ask a question where in the past you’d probably jump to giving an answer, notice what happens as a result.


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The Three Letter Word


Lurking in our language, there’s a number of naughty words that we have conveniently categorised as “Four Letter Words”. You know what I’m talking about.

Most of us typically utter these offensive tones to express our dislike of something, or someone. If you’ve ever been the unlucky “someone” on the receiving end of such an outburst, you’ll know that it tends to cause offence, and doesn’t do much for the relationship you might have with that person.

So we tend, as a rule, to avoid using Four Letter Words, at least if we’re interested in building a positive, trusting relationship with the people we deal with in day to day life.

Unfortunately, there’s a “Four Letter Word” that has been more cunning than most. Like a computer virus, it has disguised itself as a benign part of our language, embedded itself in our communication system, and is causing havoc without us even consciously knowing it. Whoever invented this word was sly indeed – they disguised it as a three letter word, while having the same offensive force as the common, garden, four-letter variety.

The word? “But”

It shows up everywhere. Once I began to notice the “But” phenomenon, it appeared incessantly. The first time I tuned into it was on the radio, when I heard a prominent politician saying something along the lines of “we have consulted with the local residents on this issue, and we fully understand where they are coming from. But our advice from the experts is that …blah blah blah…We will give both sides of the story full consideration blah blah blah and come to a final decision.”

My translation? “We are siding with the experts on this one, and we don’t value the residents’ point of view.”

Words create worlds. Our language we choose to use betrays our thinking. What the use of “but” said to me in the above example was that this person’s mind was already made up, and he was going with the experts. On the surface it may appear that he was being objective and impartial. At a deeper level, if you really listen, you can hear the real thinking and intention behind his talk. All because of one little three letter word.

In many cases, the use of “but” says “Ignore everything I have just said, this is what I really mean.”

Further examples:

“You did well in covering all the relevant points in that last report, but you need to work on cutting it down” (Translation: “Your report was too waffly and I think you need to be more concise.”)

“I love you, but your nose hairs are too long” (Translation: “I don’t find you attractive right now.”)

The upshot? We often trigger negative responses in other people, either at a conscious or subconscious level, when we unwittingly use the word “but”. Responses that could include defensiveness, frustration on outright anger. In trying to be nice, in attempting to be seen to be offering a balanced view, things can may not go as well as you’d hoped. You may not get the buy in you’ve been hoping for. In my experience, people, at some level, get a sense that you are not saying what you really want to say. Trust, at some level, breaks down.

By the way, if you really want to break down trust, forget “but”, and try “however” – and watch the relationship dissolve before your eyes…

So what do you do if you want to get your point across and maintain the relationship? Fortunately, there’s an easy solution. An antivirus, if you like. And it comes in the form of another three letter word.

That word? “And”

Try replacing “But” with “And” in any of the three examples above. Consider this: “We have consulted with the local residents on this issue, and we fully understand where they are coming from. And our advice from the experts is that …” Does that sound like a more truthful, and potentially more effective way, to building trust and credibility with the audience?

The trick is that “and” has the effective of building on what has been said previously. “But” tends to negate. The speaker is genuinely heard to be offering a more balanced point of view when they use “and” rather than “but”.

You might take a moment to reflect on how often you’ve used the three letter word today. My guess is, that if you have, it hasn’t been intentional. Most of the time, we say it without giving it a second, or even first, thought. And what effect does it have on your audience? What effect do you intend having?


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