Jul 8, 2022

Clear is Kind. Unclear is Unkind. How to Lead Challenging Discussions

‘Looking back, is there a situation you wish you handled differently? Is there something you learnt from it?’

And there it was - one of those interview questions asked by a recruiter during an interview that you can’t (and shouldn’t) fake.

At first, I tried to dig in my memory for something that wouldn’t look too bad to my potential employer but I knew the real answer pretty much immediately. A while back, I experienced quite a difficult time during the formation of my team. There was a particularly disillusioned, but strong-willed team member who posed a challenge. Since she was a true specialist in her field, I wanted her to be on my side during those turbulent times. However, I was afraid she was on the verge of quitting, and I didn’t want that to happen. I wanted us to like each other, to get along, and I was worried that addressing her frustrations and disillusionment openly would create a conflict, speeding up the process of her departure,  and so I tiptoed around the situation and waited for the storm to pass. If you’re reading this, please accept my advice and don’t wait to speak up. And be  as clear as possible. If the situation happens, prepare yourself for it mentally with this one simple quote from Brené Brown’s book Dare to Lead: ‘Clear is kind. Unclear is unkind.’ (Brown)

“Do you know what is at the centre of the issue in situations with colleagues that are challenging? Expectations.”

Do you know what is at the centre of the issue in situations with colleagues that are challenging? Expectations. I know, I was surprised too! Originally, I thought it’s going to be some profound issue like the complexity of feedback, ego or demotivation. But no - it’s all about expectations.

I expected my colleague  to understand that I wanted us to get along, to cooperate and get back to business. But, it was unkind of me to expect results and hold the person accountable for not being the pillar of the team without actually getting clarity on what it was I wanted and why without giving her a chance to communicate  with me what she actually needs in order to get back in the saddle.

Long story short, the topic eventually came up and my immediate reaction to what I was hearing was ‘Ok, I understand and I’ll do my best to make it better’. You see, that’s the typical reaction to something that makes us uncomfortable. We acknowledge that we’ve heard what was said (because we kinda have to) and then run away from the situation- and we run fast. However, I’ll let you in on two major secrets that will make leading challenging situations much easier - stay curious and don’t be intimidated by silence.

“However, I’ll let you in on two major secrets that will make leading challenging situations much easier - stay curious and don’t be intimidated by silence.”

Instead of shutting off and fleeing the conversation, ask for understanding. Replace ‘Ok, I understand’ with ‘Tell me more. I want to understand.’ And actually listen. Don’t formulate your response while the other person is talking. Don’t nod faster and faster in order to let the speaker know they should wrap it up. Just listen and stay curious. Ask insightful questions using the right kind of language and allow for a lot of silence since it is during those silent moments that we actually reflect on what we think and feel. It also gives us a chance to form a perspective.

Secondly, always remember that you are not responsible for people’s emotions. We tend to feel responsible and guilty for the emotional reactions of others so we avoid getting into those deep, vulnerable spaces. Even though it may feel strange at first, remember that only when the behaviour is inappropriate, you set boundaries.  What I mean is that if the person is angry or sad, that’s okay. If they start to yell, roll their eyes or pass passive-aggressive comments and put-downs, that’s when you should set boundaries.

Lastly, let’s be honest - these types of conversations are rarely urgent. In the heat of the moment we think they are but it is just an illusion - a fake urgency.  If you feel like either of the parties are getting too emotional, have the courage to ask for a timeout and for an opportunity to circle back to the topic at another time. It might just do the trick for all involved.

So do you know what my answer to the recruiter was to that peculiar question? I said that I now know that I should have had an open and honest conversation with my colleague on my team straight away, allowing for curiosity and empathic listening. And that I’ve learnt the lesson of how to lead a challenging conversation sooner, rather than later. I also learnt that expressing ourselves loud and clear regarding our expectations is not only a must but that it is kind. Because clear is kind. Unclear is unkind.

Rules to follow when leading challenging discussions

  1. Express your expectations clearly
  2. Stay curious and ask questions to understand
  3. Listen with empathy
  4. Remember that silence is your ally
  5. Ask for a timeout if necessary and circle back to the conversation later


  • “Rumbling with Vulnerability.” Dare to Lead: Brave Work, Tough Conversations, Whole Hearts, by Brown Brené, Penguin Random House UK, 2018, pp. 45–69.
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