The most important person in your digital and transformation team is probably the one who has the reputation for being ‘difficult’ or ‘challenging’. You know who I’m talking about, the one who wants to slow down and ask more questions, the one who wants to understand the ‘why’ as much as the ‘what’ and ‘how’ of the problem you’re trying to solve. At their best they may have been pegged as a disrupter, a poor team player. At their worst they’ll have been worn down and become cynical, or resigned to having their questions ignored.

But this person, far from trying to derail work, is actually a key component to the right delivery. They are the person who hasn’t unlearned how to ask questions, is more interested in discovery rather than conforming to culture, who has an almost fanatical devotion to understanding what users need (whether they identify as a UX person or not). Far from being a threat to your team and your work, this person should be a valued asset.

Harvard Business Review, in talking about the art of asking questions, talks about an estimate that 70-80% of children’s dialogue is asking questions but as adults this drops to just 15-25% of what we say. Do we become less curious or do we just learn that adapting to culture, giving the right answer, leads to more rewards (or at least an easier life), and the avoidance of uncomfortable change? Either way, we as people often stop asking questions.

In the workplace doing the wrong thing but doing something is often valued more highly than thinking deeply and slowly. You may not be rewarded for a ‘meh’ outcome but you’re unlikely to be punished either. However, taking your time to try and uncover what the real problem is and as part of that quest asking questions on how things are being done at the moment – well, that can make you a performance issue, a problem. Friction caused by questioning is often judged more poorly than keeping quiet and perpetuating flaws.

If you want to deliver successful digital projects (or any other project for that matter) you need to break out of that culture and start being that annoying child: the one who asks why why why why?

That same Harvard Business Review talks breaks that down into four types of question we should take the time to ask in order to reach the right decisions: clarifying, adjoining, funnelling, and elevating.  Each type helps us grow our understanding, either by making sure we’re not making assumptions or bringing our own experience too heavily to bear, by broadening out the topic not to enable scope creep but to know which outliers and look-a-likes can inform us, and by asking more deeply about the issue at hand.

In a digital project, and certainly in the often underlying and unrecognised service design that is a good projects beating heart, these questions may well slow down the discovery phase and they will almost certainly cause some discomfort throughout the organisation. They are likely to uncover obsolescence, and inefficiencies, and even where they don’t just casting a spotlight will be enough to cause some parts of the organisation to try and close ranks and retract away from inquiring teams.

Asking questions and trying to understand can often lead to the person, the team, on the receiving end feeling they are being judged. Good questions though are objective and while there is a purpose, there should be no agenda. They are asked without an answer already being in mind. This is not the classroom where a right and wrong answer is the norm, but discovery where the value is in the asking.

Digital transformation projects fail all the time, they fall short of their aspirations no matter how skilled the team and how good their intentions. It’s time to start looking at whether this is because the solution is so often put at the front, and the speed of delivery is most often given priority, compromise is too often made in favour of a previous bad decision or to maintain a status quo. To really start to make progress we need to go back to questioning what we think we know and truly, openly, asking as long and hard as it takes to understand the problems before we commit to any solution.


I’m a freelance digital content strategist and journalist. More about me and how to get in touch about working together here. You can find me on Twitter – please come and chat!

I am editor of Louder Than War – find my words about music on the site here. We have launched as a magazine and you can find us in WHSmiths or order online here. I also write for Sounds Magazine. And I’m founder and Editor in Chief of Storge – a music and culture website for Derby and Derbyshire.

I co-own record label, artist management and live music agency Reckless Yes. Find us hereand buy our records here. I offer music PR, live promotion and digital communications at Noble and Wild – our website,on Twitter and on Facebook.