I read an article recently about a group of friends throwing an ‘admin party.’ They gathered together, sat at their laptops and completed all those niggling tasks that had been taking up mental space. They held each other accountable so that difficult emails were finally sent, subscriptions were updated, and appointments booked.
I loved that it’s such a public admission that we all have tasks we’re avoiding, and I know from experience that leaders are no exception.
An uncomfortable truth we see repeatedly in coaching conversations is that what leadership avoids shapes company culture. Avoidance isn’t neutral; it creates an ‘under-the-surface’ contribution to team norms, psychological safety, performance, and trust. In fact, it’s so prolific that this is the first in a three-part blog series on the most common leadership avoidances that show up repeatedly in coaching conversations.
Avoiding the awkward 10-minute conversation
Areas where many leaders struggle, are so-called ‘friction points’ or a ‘watch item’. It might not be a performance issue, but it’s an emerging or troubling pattern that shouldn’t be ignored. It might be feedback about behaviour that’s starting to grate or spread, a missed commitment that’s increasing in frequency, or tension between two team members you’re hoping will resolve itself.
In general, leaders don’t avoid conversations because they don’t care. Instead, they might be worried about how the other person is going to react, or fear causing discomfort or awkwardness. They might feel they’ll be seen as argumentative, difficult or combative. But, dig a little deeper, and there is also a huge vulnerability around leadership expectations, that they’re simply expected to know how to handle difficult conversations flawlessly purely because they hold a senior position.
However, by putting off that difficult conversation today – and probably tomorrow – the problem grows and mushrooms. The behaviour continues and often escalates, silence starts to look like acceptance, and colleagues take their cues from what isn’t being challenged. People learn far more about company culture from what is addressed or ignored by senior leadership, rather than what is written in any company manual. What the leader thought they’d avoided has now shaped the company culture.
Key coaching tips to handle the awkward conversation well
The main learning I want to stress is how rarely the feared reaction materialises. The chances of defensiveness, a fallout, or an emotional blow-up is slim, especially if the conversation is handled with clarity and care.
In coaching, we help leaders move their focus from what they can’t control (the other person’s reaction), to what they can control (their approach and tone), and ensure the conversation is constructive rather than confrontational.
That includes:
- How you prepare, such as knowing how to succinctly lay out the issue and the impact.
- The words you choose.
- The environment you create (ideally private, calm, and unrushed).
- How you show empathy and care.
- Earmarking a time when neither of you need to rush off, so the person isn’t left with unanswered questions.
The goal isn’t to eliminate all feelings of awkwardness, but to approach the situation with a view to improving things for all parties. Plus, by having these conversations regularly, leaders build skill and confidence in handling tricky situations.
By leaning into these short, brave conversations you send a powerful message that issues will be addressed with care, and that your leadership style is people-centred.
If all of this sounds familiar and you’re looking to build confidence and skill in courageous conversations, coaching can help turn these moments from something you dodge into something that strengthens trust, company culture, and makes you a stronger leader.