Why are difficult conversations still so… well, difficult? (And what to do about it)

In the last two weeks, I’ve had more than five conversations with leaders at all levels and with varying stages of experience about how they struggle with having ‘difficult’ conversations at work. 

You know the ones. Like, how to tell one of your direct reports that the way they’re talking over everyone in meetings isn’t doing them any favours. Or how a peer’s regular habit of last-minute requests, like: “can you get this done for an important report tomorrow?” drives you insane. Or that even though you know your team member is going through a marriage breakup, the seventh time they’ve missed a deadline this month is causing the rest of the team to need to carry them. 

For most of us, constructive feedback, or engaging in so-called “difficult conversations,” remains awkward, draining, and something we do our best to avoid.  But our organisations demand it, teams need it and - soz ‘bout it, it’s part of your job description as a leader. 

So why do we struggle with it? And the question I’m sitting with as I research leadership development effectiveness, is how can we design better training to help leaders cross that bridge?

Let’s start with why feedback and hard conversations are so hard:

Here are some of the root causes, backed by research and real-world patterns:

• Emotional high stakes & stress makes it hard!
  Under pressure, cognition narrows. The higher the stakes (whether that be performance, or the relationship) the more we tend to jump into things like avoidance or blame. Just when we need things like nuance and listening, stress nudges our brain to do the opposite.  This research in ScienceDirect backs this up. What’s more, if we believe Harvard’s learning guide for navigating difficult interactions, as workplaces become more collaborative and expectations for authenticity rise, more conflict or friction is inevitable. 
• Lack of psychological safety or relational capital
  I often say that as a leader, building trust is your priority. You’ll encounter difficulties if you don’t prioritise trust before anything else. And courageous conversations? They’ll become pretty wobbly if you haven’t built trust and respect beforehand.  If teams haven’t built trust or been purposeful at building a feedback culture over time, people often hear critique as an attack instead of an opportunity for growth. See this blog on how to build trust – and do the groundwork before the talk. 
• We’re not collectively clear on what’s expected
  If you haven’t consistently reinforced what “good” looks like, or if standards shift without any changes being communicated, feedback feels arbitrary or unfair. So, before you jump into that honest conversation, ask yourself, ‘is everyone crystal clear on what we have agreed to (whether it’s about behaviour or tasks)? If not, start by defining that collectively to ensure you’re all on the same page. 
• Lack of practice 
  Too often, leaders are thrown into a live feedback moment with little rehearsal or support. The models are taught (e.g. SBI) but not contextualised or practiced under pressure. The gap between theory and real-world execution is where most training fails. Knowledge isn’t enough. We need to practice and practice, fall over, stumble, get back up, reflect and practice again.
• Complexity and pressure
  As a leader, you’re no doubt time poor, juggling many moving parts, under pressure to deliver and all manner of things.  Having to balance multiple perspectives, power dynamics, hidden emotions – it’s enough to make you want to put tricky chats in the too-hard basket. The more ambiguous the situation, the harder it is to deliver feedback with clarity and empathy. Research shows that communication is not just about content; it’s also about relational dynamics, interpretation, and narrative framing. 

So how do we train leaders, so they become confident, effective “feedback agents”?

Given these obstacles, how do we design or coach leadership development, so leaders become surefooted rather than shaky when it comes to crucial conversations?

1. Embed feedback as a daily habit, not a once-off workshop
   McKinsey & Company’s research shows that in organisations with strong performance systems, 71% of participants said their managers were trained in providing feedback and coaching and that training was ongoing, not one-off. 
   So, consider: How can you build small, micro feedback into your daily operating rhythms? How can you build in self-reflective practices? Make feedback like the tides – two ways, every day and no big deal. 
2. Simulations & just-in-time rehearsal
   Theory is all good and well (and a cornerstone to learning), but practice under “safe but real” conditions is where the magic happens. Simulation, just-in-time rehearsals, and feedback preparation coaching all are shown to increase participants’ confidence, skill and emotional resilience, according to studies. This is about using real-life or realistic scenarios to rehearse and reflect. 
3. Design training around your unique context
   Don’t teach “Feedback 101” in a vacuum. You can use basic but proven models like Situation-Behaviour-Impact (SBI), for sure. But don’t just teach the theory. Apply it to the types of scenarios your leaders will experience. Adapt it to your culture and your operating realities.  
4. Don’t forget to include emotional intelligence and self-awareness as part of your training
   Confidence comes from self-awareness. Develop your leaders’ capacity to notice their triggers, manage defensiveness, and reframe feedback as an opportunity to collectively solve problems. I’ve seen some of the biggest breakthroughs in The Leader’s Map, when people uncover their own resistance, become more self-aware of their triggers and tendencies and trade assumptions for curiosity. “What’s driving this behaviour?” is not only a great question to ask of the other person, it’s a good one to ask of ourselves! 
5. Build a feedback culture and don’t rely on one-off training.
   Leaders don’t operate in a silo. There’s no point sending them on a training course for feedback if, when they come back to the organisation, it's not modelled at the top or the culture goes against giving, receiving and seeking feedback. Your broader culture must support candidness, open dialogue and permission to course correct. Training’s ineffective without reinforcing systems. What are your norms around feedback? What is rewarded in your organisation around courageous conversations done well? As Michael Timms argues, “establishing feedback as a norm helps make hard conversations less rare and more expected.”
6. Measure impact, iterate and improve
   “We respect what we inspect, not just what we expect.”  Track metrics like quality of feedback (via 360s or surveys), manager confidence, follow-through on feedback actions, team perception of fairness, and downstream performance indicators. Use this to continually adjust training content.

Leaders tell me again and again: “I avoid giving feedback because I’m cautious about the fallout or reaction.” But what if we turned that around and taught ourselves to welcome these moments?  They can even be, dare I say it, clarifying, aligning, relationship-building opportunities. 

If we shift leadership development from “telling leaders how to give feedback” to “helping leaders become fluent in relational, high-stakes conversations”, that’s progress. 

With all of this said, what’s one thing that you can implement or try in your organisation at present? I’d love to hear what resonates and what you choose to take forward.