Don’t advocate for the devil

We’re in a workshop. Let’s say it’s story mapping - a useful tool which can encourage conversation, build shared understanding and start a good direction of travel when developing a product. As the workshop gets started, someone has a question….

All the questions

We’ve all been there. The meeting, meet-up, the Q&A slot where someone asks questions, lots of questions. Are you that someone? Why would that be?

Is it easier to ask many questions than share your ideas? Harder for people to know you don’t have all the answers?

Are you listening or busy shaping your next question?

Do your questions provide a helpful disruption? Are you creating a pause or helpful shift in direction or simply serving to knock someone off course?  

You may feel safer to continue to question, to prevaricate than make a decision - especially when decisions can be hard and viewed as wrong. Are you thinking - if you never make a decision then you can’t make the ‘wrong’ decision?

Have you opened your question with….’as a devil’s advocate, why…’? Unless that’s a holding position the group has agreed to take, say when they want to avoid unintended consequences for new products, content or policies. Otherwise….

Why would you want to advocate for the devil?  

Sometimes it’ll be sealioning. I’ve not always been speedy to spot this and allowed my (or others) time and space to be taken up by people pretending to be inquisitive or ‘collegial’.  

Sealioning refers to the disingenuous action by a commenter of making an ostensible effort to engage in sincere and serious civil debate, usually by asking persistent questions of the other commenter.....phrased in a way that may come off as an effort to learn and engage....but are really intended to erode the goodwill of the person....to get them to appear impatient or to lash out, and therefore come off as unreasonable.

Be honest with yourself. Are you wanting to undermine, patronise or remind people of your self-absorption and importance?

Are you the one who always asks questions, asks the first question, raises your digital hand repeatedly or your comments take time to scroll through in the chat? You don’t have to be the rock star, the 10x developer, exec, manager or analyst.

By now you’re thinking - ‘that isn't me’. Great - thank you and this is a reminder to step in or support when you see this happen and seek to create a different environment. Look out for people who never ask questions and provide different options and routes for them. Have you made it clear that people asking questions, allowing and encouraging all to speak or share, doesn't mean all ideas will be taken on? Are you allowing a perceived and often misplaced need to be civil and kind to override asking the devil’s advocate to take a seat or leave the room?

I know stepping in isn’t for everyone, in every role, institution, organisation or team. Not least if your manager is the devil’s advocate and recognising this may be the start of a new journey for you.

Maybe you’re thinking, ‘this could be me’. If it feels I’m writing about you - that’s for you to decide, great that you’ve spotted this and welcome back.  

This isn’t to say never ask questions and don’t ask lots but to think of your intent and impact - especially where hierarchy, grade, roles have over-riding or systemic importance in your environment. Your behaviour and questions don’t exist in a vacuum.  You can’t always be right - no-one can.

How do you know you asking all the questions, always asking the first question isn’t stopping a different perspective being shared? That someone else’s question won’t highlight a gap in understanding. What could you do to feel brave enough to do that?

If you're normally the first person to speak. Aim to be second or third next time. Count to 10 then 20. Are you paternalistic or thinking you need to always fill a silence?  

You’ve tried WAIT (why am I talking?) so now’s the time for *WTFAIAFTD. Sorry.

What kind of organisation culture do you want to encourage? Have you shared the reasoning behind your questions? What decisions and actions do you want your teams and individuals to take when you’re not in the room?  

Despite what you may want or feel - they will make decisions. What are the guardrails or underpinning principles and how can you develop them together?  

Silence is not golden

We’ve all been here too. No-one asks questions or it’s rare. Maybe that’s you - never asking questions, maybe it’s common in your teams or meetings. Why would that be? What is the silence telling you? People may be stuck, tired, bored, broken or been told they are the wrong role or grade to raise a hand. It could be unsafe, there’s negative consequences and you’re seen as a trouble maker (is that always a bad thing for everyone?). Questions have been scoffed at, skipped over or dismissed.  

If you’re the one with the power or loudest voice - how about shutting up sometimes? If you feel you need to continually prove your position, give yourself some time and care by not being in the room. What can you do instead to ensure other voices are heard?  How can you get comfortable with that?

Why bother? Cos it’s the right thing to do and to not do so would be a lie. Well, it would be if you’re talking in a place which has made a commitment to equality, diversity and inclusion. This isn’t about ‘diversity of thought’ by the way but it’s certainly part of the culture and system you’re creating, reinforcing or choosing to change.  Nothing in isolation.

A new or even uncertain question can be a helpful flag to uncover an oversight. Wouldn’t you rather learn about a potential issue before a product release or a security incident occurs? What needs to change, be created, piloted or healed Noticing the absence of questions around you is recognising something needs to be fixed.

I’ve written about my experiences of being an unsure questioner and some of those prompts may help.  I’ll likely come back to this I’ve learnt a lot since then and I’m also bolder.  

Just enough questions

I love being here. When the questions are good. Varied and sometimes shaped as they are said. Someone wants to check their and the group’s understanding and adds nuance, a shift in perspective or hints at a gap in my understanding. I’ll ask and invite questions to do that.  I’m comfortable to share what I know and acknowledge what I don’t. That’s ‘cos it’s the right thing to do and also signals to others that it’s ok to be curious, fallible and open to constructive challenge.  

To de-centre myself, provide an opportunity for someone else to share and think out loud. I want to ‘listen generously’. (I’ve nicked that phrase from someone and found it scribbled in my journal - so this is an anonymous thanks). I’ll ask a question to flag what I know may be sometimes viewed as an edge or from the margins though a margin is only a margin if it’s not yours. Accessibility and unconsidered consequences - I’m thinking of you here.  

I’m also being selfish.  Encouraging and supporting questions provides a better opportunity for shared sensemaking. As I was writing this, I spotted a tweet which took me to an article outlining the importance of ‘frequently (digging) into the “how” to understand and navigate the nuances of our strategy together and often’. That must have included good questions and the importance of shared sensemaking, summarising with

‘alignment is the difference between progress and stagnation’.

I’m aware that my ‘right amount’ is personal and it’s important to acknowledge and agree boundaries, subject people or context. It also doesn’t mean I have to accept the answers but I have a responsibility to listen.  I can agree - unless you’re advocating for the devil then I'll likely disagree and maybe even not listen.  

And now?

Does this pause or shift your thinking and behaviour? Do you advocate for the devil and, just as importantly, what’s causing that and do you want to change?

Who in your organisation is the devil’s advocate and what can you do to understand, support or call-out?  Have you created spaces which make devil’s advocacy easier and how much (extra) energy do people have to burn through to raise a new hand or perspective?

What triggers you to ask questions or to pause when you’d rather say something? When do you feel excited and safe to share?  

We need to provide time, opportunities and routes for people to ask questions (including anonymously) and create space to answer them.  There must be some urgency behind this - not to rush to answers but a definite approach and plan to get there.  

It’s back to the story mapping workshop, creating the right products, forming good decisions - it’ll only be as valuable and successful as the interactions allow the tool to be. You can’t be successful without focusing on the tools and the interactions and leave the devil outside the room.  

* WTFAIAFTD = WTF am I advocating for the devil?  A dirty and apt trick to get you to scroll to the end and there'll be a prize available if you’ve got a better abbreviation.

As always, these are my unfinished words of warmth and wit based on commitment and compassion.  

(Images from Demon icons created by Freepik - Flaticon and a very mixed feeling playing with DALLE-2)