Questioning – James Osborn

It Depends

A classic answer to a ‘simple’ question, “It Depends” is what you’ll often get back from an experienced person whenever you throw them something formulated as “What’s better, A or B?”.

It can feel very frustrating to get this answer back. Maybe you wanted a quick confirmation or to settle an argument by getting the support of someone more senior.

“It Depends” is an answer asking for more context. It’s rare that there’s something that’s always a slam-dunk good choice, and probably more so when it’s a topic that someone needs to ask for help on.

It’s especially common in tech circles, but any complex field will be familiar with this answer. Where there are lots of ways to approach a problem, and the context of the problem tend to really matter, then you will find out that it really depends.

So, what can you do in this situation?

First up, accept it. You’ll hit the “It Depends” answer every so often, so be prepared to meet that request for extra context. A good experienced person may ask some immediate follow-up queries to get the context they’ve invited, but you can start to give it if you aren’t asked. “Okay, well, I’ve tried X & Y. My constraints are C, D & E. I need something that works well enough for this scale before the end of the month.”

Give the context, and you’ll get to a more useful answer from your available options.

The other approach is to go in with context, and rather than asking if “A or B is better”, you can ask “with this information, what could we try?”. Recognise that you get an “It Depends” answer by giving a blind choice, and step around it with some preparation. Who knows, by thinking about the context in more detail, you might just find the answer without any support!

So don’t get frustrated with “It Depends”, there really aren’t simple answers in complex spaces. Instead, recognise it as a request for more context, and build that shared pool of meaning to get to a good answer.

Watch out for Why

When we’re coaching, we should find that the majority of our questions are Open, designed to trigger more conversation and to give the coachee the balance of time to share their meaning.

That means that we will prefer to use questions starting with words like What, When or How as these will tend to be answered with more than just a simple Yes or No response.

Why is also an Open question, but it comes with a warning label. If used incorrectly, it can sound as if the coach is accusing the coachee of something, or suggesting that their answers are not ideal.

“Why did you chose that option?” can be taken as an attack on the coachee, with an implicit assumption that the coach disapproves, or feels another choice would have been better. If this happens, then it can close down the coachee, and the coaching outcomes will be less successful.

We can mitigate this impact with careful use of tone and rapport, softening our approach to show a desire to understand rather than to judge. We can also choose to rephrase our questions, flipping a Why to a less strong term “What was your process when selecting that option?”.

If we want to shock the coachee into greater awareness or to cause some deeper reflection, then we can use a strong form of a Why question to trigger this thinking, but this should be approached with care.

So, with all this said, Why is a powerful tool in the toolbox of a coach. We shouldn’t be afraid to use it, but we should be considerate of the risks it may bring to the conversation and how it can alter the flow of a relationship with a coachee.