How to ask better questions
This isn't a question.
We are told that “asking better questions” is essential to an empowering leadership style. But how do we actually go about it? It sounds so logical, encouraging people to think and come up with innovative ideas, more than a single person can come up with and into which they’ll buy in, but how can we improve our question-asking skills?
Turns out it’s less complicated than you might think, and doesn’t require deep domain knowledge.
Why Questions
Questions are powerful for a variety of psychological reasons. When we are asked a question our mind tends to automatically start formulating an answer. We are far less rational creatures than we’d like to think; in fact, as a species we are more rationalising than rational. For those familiar with Thinking, Fast and Slow, we spend far more time in System 1 thinking, even when we’d like to think we carefully consider the options.
So add the two observations together and you get: when asked a question, the mind automatically jumps to thinking about an answer, which it then justifies by rationalising. And once rationalised, people tend to stand behind their answer, because after all they just verbalised something so they must believe in it. Right?
It’s also why asking why can be dangerous — the mind may come up with an immediate rationalisation, rather than any real basis for the action. It’s often better to ask other, specific questions. For example, instead of “why did you click there?” we might ask “What did you expect to happen when clicking there?”
I hope this gives an insight into why we should use questions, but why we should use question other than why. Well, hopefully an insight rather than a headache 😉
Cognitive Biases
There are many cognitive biases we should be aware of. It’s hard to fight them and the tendency to jump into “solution mode” within ourselves, but luckily spotting the flaws in others is easy… Or, at least, with a bit of practice it becomes easier to direct people into coming up with innovative solutions that they’ll rally behind.
I won’t go into detail about cognitive biases. Many of the ones that UX researchers talk about apply here as well — confirmation bias, framing, et al. See this list or this article as great examples. Instead, I’ll focus on the context here, of leading people to increased innovation and engagement.
Socratic questioning
The Socratic method refers to asking leading questions where you want the other side to reach your pre-determined conclusion. It works for sophistry, but people usually recognise it for what it is and come to resent it. Also, the whole point is for people to come up with ideas you might not have thought of. So while the tool has it's uses helping people come to certain realizations you can already see, it’s best used sparingly.
If before Why
If I asked you why do users fall off in the 3rd step of the acquisition funnel, you might be tempted to go open the onboarding screens and start theorising why the third page is hard. But do they? Are there perhaps data anomalies that might mask what’s really happening? It’s always worth validating what is happening before trying to theorise why it might be so.
False Dichotomies
This is anything that forces an answer or either A or B. This applies to yes/no questions, but the general case is anything that limits choice. Roger Martin has written articles and books about using integrative thinking to break away from this pattern and open new possibilities. In our context, I usually aim to avoid closed questions for the same reason I avoid the Socratic method. The aim is to encourage people to think and generate options you might not be aware of, not force them into pre-determined choices.
Leading by Questioning
Knowing when to ask
Remember what the goals are for leading by questioning. One, to come up with more ideas than a single person can, gained from deeper querying of the context. Two, get people motivated because they came up with those ideas. So don’t be that guy who always finds fault with everything. Sometimes it’s OK to just say ‘sounds great, go for it,’ even if you think you may see some possible issues. An idea that’s 80% there with someone 100% behind it is better than an idea that’s 85% there but executed by a 60% demotivated person. (And that’s assuming you can predict improving the idea by a solid 5%).
So first, when someone comes to you, ask them “what do you need from me?”. They may need actual answers, unblocking something, or be a sounding board. Then, when appropriate, give your people (and yourself) space to experiment and learn.
Knowing just enough of the domain
Professional coaches and say that they can help people overcome challenges regardless of their own understanding of the challenge domain. That may be so, I am not a professional coach. Within product management (and corporate leadership in general), there is usually an expectation that the leader knows enough about the practices and markets in their domain to run their group.
Product Management is essentially a cross-functional practice, where a competent PM can speak confidently to techies and engineers, executives (both internal and customers), sales and marketing, et al. In my view, there’s more difference between B2C, small B2B, and Enterprise software. Not that the principles of product management are different, but the availability of data, accessibility of consumers/users and stakeholders, the pace tend to be very different, leading to different practices and expectations. Within those categories there is often more similarity than differences.
When learning a new domain, bringing a fresh viewpoint (a beginner’s mindset, querying everything) is usually an asset. Don’t be afraid to keep this mindset when leading. It’s often very useful to ask those “naïve” questions and for your people to explain the reasoning behind their ideas and suggestions to you. Often in discussion you’ll both spot areas that need to be thought through more deeply.
Your domain knowledge as you build it up will help you see more dark corners that need some light, and may helps in understanding when you’ve dug deep enough and need to move on. But honestly, “have you checked with Legal?” or “have you considered the ramification on tech support?” are almost always a good question to ask, across any domain.
The 5 Whys
The Five Whys is a method popularised by Toyota in manufacturing and then Eric Ries in Lean Startup to do root-cause analysis. The idea is to dig through the obvious causes to more fundamental ones, and then allocate remediation resources according to risk of recurrence at each level.
My observations are that “why” is often the wrong question, as listed above. It’s usually better to ask specific questions, like “what could have caused this” or “what were we expecting”. The other observation is that when “it’s that person’s fault” comes up it’s worth digging more into why that person did what they did. It could be something simple as lack of training in a procedure (or a wrong procedure, aka releasing to production on Friday afternoon), or something quite else that we just don’t see yet.
A similar idea applies to leading by questioning — digging deeper than surface reasons will expose more of the problem and solution spaces, and this greater context allow you to better find a fit. Or, to be more accurate, it’s not just you but the team you are posing the questions to who would benefit from answering. And five levels seems like a pretty decent amount of digging, balancing merely scratching the surface, falling into blame games, or getting analysis paralysis.
Providing feedback
You can also provide feedback via questioning. That is often more neutral: it’s less confrontational and keep your biases under control, and has the advantage of buy-in when a person says something about themselves.
What do I mean by that. First, all feedback says a lot about the person giving it, sometimes more than the receiver. It’s nearly impossible not to let your own pet peeves and biases creep in. Still, feedback is a gift and often people need to hear it — though they may not want to. By questioning the feedbackee (I’m an author, I’m allowed to make up words), you can eliminate some of your own bias-induced jumping to conclusions by letting them voice their own view of events first. Then, if you can make them realise it was suboptimal and an opportunity to improve, once people verbalise something about themselves they tend to stick with it (congruence of self-image).
Imagine you noticed one person shutting down another in a meeting. Take them asking and ask questions starting with “tell me what you think just happened”, and continuing with “how do you think the other person felt when you said it?", or “how would you react if the situation was reversed?”, leading up to “what can you do next time?”. Pretty classic counselling and coaching techniques, but very effective on iindividuals and teams to help them grow empathy and come up with better solutions. In less trivial examples, they might have surprising insight into the situation that you haven’t thought of — leading with a commanding feedback would have made the person bring it and and clash with your (possibly still valid) view. This way you get to safely explore the situation together with the person via questioning as part of feedback.
Dealing with walls
Sometimes you’ll run into things that are completely non-actionable, or simply unhelpful. The above “it’s that person’s fault” (accompanied with a truculent tone) is an example, or “because that’s how it’s done” as another. Asking “why do you think that is?” and “what could be another reason for it?” repeatedly is a non-judgemental, non-confrontational way to deescalate emotions, and encourage thinking from multiple viewpoints until you reach an actionable answer.
Note that you don’t have to know what the '“right” answer is. You just need to encourage people to think productively and shift their perspectives. Once the team comes up with something potentially productive, you can just say “let’s try that.” The value lies in them having come up with the ideas, getting themselves unstuck and thus behind the course of action.
Final thoughts
Leadership starts with self-awareness, so asking questions applies to yourself just as much as it applies to leading others. If you catch yourself in a loop, a rut, or just plain annoyed “other people” throwing spanners into the works, you can take a breath and apply many any of these techniques on yourself. What are those others seeing that you don’t? What could be the reasons behind the data? What else could you infer?
When you want people to think deeper (especially if you spot a potential for trouble and want them to explore and acknowledge other points of view in a safe way), as questions like “how would that work in practice?” or “how would you implement this? what wold be the follow-on effects across the various dimensions of the business?”
Also be conscious that when we ‘think through’ something we are subject to the same cognitive biases as everyone else, but they are harder to see. This is why a long-form written narrative is so powerful. It forces you to clarify your thinking and go beyond the immediate hand-wavy explanations. So keep questions neutral, and get people to methodically think about their ideas and proposals, not out of manipulation but simply to better explore the space and reach better outcomes.
So that’s it. Leading by questions isn’t a hard skill, just something that you need to practice. Ask open-ended questions, use techniques from 5 Y’s to Chris Voss’ Tactical Empathy to encourage people to talk and think from multiple view points, and encourage them to come up with ideas and then execute on them. It’s a mindset more than anything, catching ourselves jumping into “solution mode” or latching to the first surface explanation, and then querying methodically to explore the possibilities.
What questions have you found useful? What were your experiences of leading with questioning?