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How Asking the Questions Others are Afraid to Ask Leads to Better Conversation

Speaking Up

All too often, we don’t speak up for fear of what others, even strangers, might think of us. This shows up in both our work and personal lives. It stifles important conversations, thwarts progress, and keeps us confused.    

Yet, how many times have you felt relieved because some brave soul asked the question, sought the clarity, or said the thing you were afraid to ask?  

Remember the fairy tale the Emperor’s New Clothes?  A vain emperor is taken in by two weavers who claim to make magnificent clothes that are invisible to people who are stupid. While there are no clothes to be seen, people fear being judged, so they say nothing.  When the emperor goes out in public wearing his spectacular outfit, it’s a little child who speaks up and says, “But he hasn’t got anything on!”  

Sometimes we need the confidence of that small child to say what needs to be said.  

Lowering the Risk of Rejection  

Amy Edmondson, an authority on Psychological Safety and author of ‘The Fearless Organization, says, “We learn early, usually in elementary school, that what others think of us matters so we learn to lower the risk of rejection and scorn and we get so good at it even if we aren’t conscious, we are doing it.”   

Don’t want to look stupid? Don’t ask questions.  

Don’t want to look incompetent? Don’t admit to mistakes. 

Don’t want to be called disruptive? Don’t make suggestions.  

It is a way of protecting ourselves. As Edmonson says, “Silence is instinctive and safe. No one was ever fired for silence.”  

To speak up, we need to feel psychologically safe.  Edmonson defines psychological safety as the belief that the work environment is safe for interpersonal risk taking. That we can speak up without fear of judgement, reprisal or humiliation. Leaders can do a lot to create that safe environment as we outline in our blog  Five ways leaders can build psychological safety. It starts with leaders setting the tone, inviting participation, and responding productively.   

What’s the cost of silence?  

What makes us hold back when we have a unique idea, a different perspective, a big question, or a valid concern? True, it might not feel safe to voice it, depending on your culture and environment, but often we are the biggest obstacle in our path. Self-criticism, self-doubt, storytelling, predicting the future, and catastrophizing can hold us back.  

“That’s a dumb idea and others will think it’s dumb too.” 

“What if my perspective is wrong?”  

 “If I challenge that idea, I’ll be seen as aggressive. I might even be kicked off the team!”  

Armed with our criticism, doubt, stories, and predictions, we choose silence and instead we jump on the bandwagon of bad ideas, hold back great ideas, allow bad behavior, and/or disengage.   

This has huge implications for organizations. Additionally, when we feel like we are the only one that holds these thoughts and feelings, it can feel isolating, and it disconnects us from others.   

As leaders, the thing we should be most concerned about is silence. It isn’t golden.  It is an opportunity to explore what is getting in the way of your team speaking up.   

Tapping into our own agency  

While we need to feel safe to protect ourselves, we also have agency to push through our fears, challenge our thoughts and assumptions and find the courage to speak up.    

In Dan Pink’s recent book The Power of Regret’, he refers to a phenomenon that social psychologists call “pluralistic ignorance”.  He writes, “We mistakenly assume that our beliefs differ vastly from everyone else’s – especially those private thoughts that seem at odds with the broader public behaviour.” 

He cites the example of when we struggle to understand a lecture, we don’t ask questions because we don’t want to look stupid. We convince ourselves that because others aren’t asking questions, they must understand it. Yet we don’t consider that others may also not understand the lecture and don’t ask questions because they don’t want to look stupid either.  

“We’re confused but we stay confused because we falsely believe nobody but us is confused,” Pink explains.     

Often our thoughts and fears can tie us up in knots, yet for the most part, they are unfounded.      

As a leader, we can take the lead and ask the question others are afraid to ask. It paves the way for others to weigh in.  

We think we are alone. But we’re not.  

The last 2+ years have been tough. Throughout it, we’ve been bringing together groups of leaders and teams to discuss all kinds of topics like uncertainty, courageous conversations, remote work, self-leadership, confidence, vulnerability-based trust, and more.  And when brave people step in and speak up about their challenges, self-doubt, imposter syndrome, burnout and when they’ve fallen short, the conversations get real and deep.   

The most common sentiment we hear when we bring leaders together is, “I thought I was the only one who…felt that way, had that challenge, or struggled with that.”   

There’s a comfort in knowing the experience is shared; that it is common. It connects us and reminds us we are not alone.  Collectively, we feel seen, heard, understood and included.   

Speaking up and saying things out loud helps us and liberates others.  

Four ways leaders can role model a path to better conversations 

Reframe the one to many: As Pink points out, we put ourselves in this false ‘I’m alone’ paradox. Instead of holding back on asking your question because you have fears, we offer this question as a reframe: How will my question help me and others who may not have the courage to ask?  Trust me, people will be glad you asked.   

Let go of predicting: If we could predict the future, we’d all be buying lottery tickets every day.  We can’t know what is going to happen before it happens. Yet we predict and tell ourselves stories that have catastrophic outcomes. How many conversations have we avoided because we predicted a negative outcome?  Even if we could predict, we cannot control how people react, think or behave; all we can do is be clear on our intentions, values and how we want to show up.   

What would it change if we accepted that we can’t know, and that people are responsible for their own actions?   

Be vulnerable first: Let’s dispense with the notion that being vulnerable is weak. Brene Brown informs us it’s the very definition of courageous because it involves uncertainty and emotional exposure. When we authentically open up to others, it paves the way for better conversations and reminds us and others we aren’t alone.   

What would it look like to be that person who bravely steps into vulnerability so others can do the same? 

Connect with others: In our remote/hybrid work environment, we’ve become more isolated and transactional and less relational.  Sometimes we forget that being human in these uncertain times is hard. Being able to speak up, say what we need to say, and hear our words is so important, especially in the company of someone who listens without judgement.  

Who can you connect with to have the conversations you need to have?  

In his book ‘Leading with Emotional Courage author Peter Bregman says, “If we are willing to feel everything, we can do anything.”  Bregman says what often holds us back from speaking up or acting is we don’t want to feel… name your emotion…ignorant, disruptive, embarrassed, awkward, hurt, shamed.   

He challenges us to feel courageously and act boldly.  Sometimes speaking up is the most courageous thing we can do because it leads to better, deeper and more meaningful conversations.   

The leader is the person who goes first. The leader is the person willing to speak up. The leader is the person who is willing to feel everything.  

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