Fundamentals of Leadership - # 4. Challenging Conversations

bev • November 2, 2026

"Don't make the conversation bigger in your head"

Leadership inevitably involves those awkward conversations.  You know the ones. The conversation you've had multiple times in your head, rehearsed in the shower, thought about on the drive to work and then put off for another day.  The more you think about it, the bigger it becomes.


But here's the thing: the conversation rarely gets easier by avoiding it.


As a leader, there will be times when you need to challenge behaviour, address performance, give difficult feedback or tackle something that isn't working, and sometimes the kindest thing you can do is have the conversation.


nugget 1. - Stay Awkward, Brave & Kind


Brené Brown's mantra is "Stay Awkward Brave and Kind" . 


She also has two phrases that are particularly relevant to leadership:


Clear is kind. Unclear is unkind.


Think about that for a moment.  When we avoid telling someone what they need to hear, we might think we're protecting their feelings. In reality, we could be making things harder for them.


If someone's behaviour is affecting the team, their performance is slipping or they are unaware of the impact they're having, how can they change if nobody tells them?  Being kind doesn't mean avoiding difficult messages. It means delivering them with respect, clarity and good intentions.


nugget 2. - Use a framework -SBI


One of the reasons challenging conversations can go off track is that we get caught up in emotions, assumptions or a long list of things that have happened.


A simple framework can help you stay focused.


The SBI model stands for:


  • S — Situation: Be specific about when and where something happened.
  • B — Behaviour: Describe what you observed, rather than making assumptions about someone's intentions.
  • I — Impact: Explore the effect of that behaviour.


Let's imagine a team member has been obstructive during a meeting.  Rather than starting with "You have a negative attitude", try:


  • Situation: "Bob, at the team meeting last week..."
  • Behaviour: "You repeatedly challenged the proposals, used language that I felt was inappropriate and did this in front of some of our more junior team members."
  • Impact: "What do you think the impact of that was?"


Notice the final question, rather than immediately telling Bob what the impact was, you're inviting him to think about it himself.  Did he notice a change in the atmosphere? How might other team members have felt? What effect did it have on the discussion?  Stay in questioning mode. Allow silence. Don't rush to fill the gaps.


The more people can recognise and articulate the impact of their own behaviour, the greater the opportunity for genuine ownership and change.  A useful reminder: describe behaviour, not personality.


nugget 3. - Hold space not fix


Adam Grant talks about the importance of holding space rather than immediately jumping in to fix things.


This is particularly important in challenging conversations.  As leaders, we can sometimes be too quick to provide the answer, explain the problem or tell someone what they should do differently.  When we do this, we can unintentionally disempower people.


Suggestions:-


  • Ask open questions
  • Give people time to think
  • Resist the urge to fill every silence
  • Let them explore their own solutions
  • Encourage them to take responsibility for what happens next


Your role isn't always to have the answer. Sometimes it's to create the space for someone else to find it.


nugget 4. Care personally & challenge directly


Kim Scott explores this beautifully in her book Radical Candour.  Her central principle is that effective feedback requires two things:


  • Care personally and challenge directly


She describes four different approaches:


Let's look at what these mean:

  1. Radical Candor: You genuinely care about the person and are prepared to be direct with them.
  2. Ruinous Empathy: You care about the person but avoid saying what needs to be said. You think you're being kind, but you're not helping them.
  3. Obnoxious Aggression: You challenge directly but without showing genuine care or consideration.
  4. Manipulative Insincerity: You neither care enough to challenge nor have the courage to be honest. This can show up as talking about someone behind their back rather than addressing the issue directly.


You can be kind and direct, and the two should go hand in hand.


nugget challenge


Think about that conversation you've been putting off, the one you've rehearsed in your head several times.


Ask yourself:

  • What is it that actually needs to be said?
  • What behaviour do I need to address?
  • What impact is it having?
  • How can I be clear, fair and kind?
  • What questions will help the other person think for themselves?


Then take a breath and have the conversation.  You don't need to make it perfect, you need to make it happen.


Challenging conversations can be uncomfortable, but they can also create some of the biggest opportunities for learning, growth and transformation.


Don't make the conversation bigger in your head. Stay awkward, brave and kind.

Fundamentals of Leadership — practical nuggets to help you think differently about how you lead.






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