Difficult Conversations – why are they so hard for leaders?

Many people leaders struggle with having difficult conversations with their direct reports.  

Whether the discussion is simply a chat raising improvement related feedback or addressing a more significant conduct or performance issue, difficult conversations can often be relegated to the ‘too hard basket’.

This delay often means issues escalate, turning a manageable feedback session into a more major issue or conflict.

So why is this a common challenge facing people leaders? 

Is it a lack of training in how to have these conversations or are there more deep-rooted psychological causes that need to be addressed first? 

New Leaders – the challenge of being promoted from inside the ranks  

For new leaders the sudden requirement to be in the ‘hot seat’ of these conversations can seem like a huge mountain to climb and can cause them to question the decision to take on the role.

Navigating the change is often significant and pretty lonely for new leaders especially if they are not adequately supported.

Negative thoughts can dominate and become a big barrier to both enjoyment of the new role and leadership success. 

  • “I’m still me, but do they trust me or just see me now as management?”
  •  “Will my former teammates still like me as a person?”
  • “How do I navigate being friends outside of work with someone who was my teammate, but now I’m their boss?” 

These are all real thoughts that newly promoted leaders experience, particularly when dealing with the tough side of leadership – the difficult conversations.   

Often new leaders are promoted from within the team.  While this is admirable from a company hiring policy perspective, the sudden transition from being a teammate and friend to being the boss is tough.  

Almost always it is psychological barriers – not a lack of training or know-how– that must be addressed first.

Common psychological barriers regardless of experience level 

It’s not just new leaders who find leaning into difficult conversations confronting. 

In my experience as a coach, I’ve worked with many leaders who struggle with difficult conversations regardless of their experience and irrespective of the journey taken to get to that role.  

Not wanting to be disliked as a person, worry about mishandling a conversation and causing distress, concern that a step too far will result in a complaint or, at it’s worst, a personal grievance. 

Any paralysis at this point minimises the opportunity to have those early conversations potentially exacerbating whatever is developing. This means the avoided difficult conversation pushes the needle closer to what will seem like an impossible conversation.

So what’s the solution to overcoming these barriers? 

It will be different journey for everyone, but what is always true is that it’s not just about training.

You can only get better if you deal with any underlying fears then lean in and actually have the conversations.  

Helping leaders move past their unique psychological barriers and face into the task with courage and positive intent is my mission as a coach. If internal barriers aren’t confronted first, the lingering fear overtakes any positive intention and minimises the value of any training. 

While all leader’s ‘mind’ barriers are unique to them, there are a couple of key concepts that are helpful to many I’ve coached.   

Emotional bank accounting  

The concept of an emotional bank account was introduced by Stephen Covey in his book “7 Habits of Highly Effective People’. 

The premise is simple: trust is built through consistent ‘deposits’ (positive interactions) that provide a buffer for the ‘withdrawals’ (difficult conversations) that leadership inevitably requires.

Leaders always have opportunities to make deposits in their ‘emotional bank’ as they develop relationships with their direct reports. That positive balance in the ‘bank’ creates a stronger relationship platform when it feels like a withdrawal is being made by having that difficult conversation.

There’s more trust, more balance – and much less doom and gloom from either side of the table.

Simple actions like:

  • openly and regularly communicating
  • taking time on a Monday morning to ask about the weekend
  • noticing when things go well and giving positive feedback, or 
  • simply saying thank you for work well done

These are all deposits that build the positive side of the ledger to keep the relationship in ‘credit’. 

Reframing the conversation by focusing on positive intent 

If a difficult conversation is framed negatively in a leader’s mind such as ‘I’m delivering bad news, I’m punishing for something wrong’ etc then that’s generally how the conversation will feel and can lead to it being put in the too hard basket and delayed. 

Focusing on the positive intentions behind raising a difficult piece of feedback flips this on its head. 

Why is it important to give this feedback?  What would you truly like to see in terms of improvement, learning, behaviour change and how will this benefit your direct report?

Most leaders want to see their people succeed and reach their potential. 

Addressing areas of improvement or behaviour that is causing barriers to someone achieving their potential is helping them put their best foot forward.  

Side by side feedback: Focus on the issue not the person  

In my long career as both an HR professional and a leader of people, I have had to have plenty of difficult conversations.

One of the most powerful shifts I have taken forward with me is the shoulder-to-shoulder approach. Instead of sitting across the desk – which creates a confrontation ‘me vs you’ dynamic – imagine standing together, looking at the problem on the table.

You aren’t attacking the person; you are both addressing the issue.

In summary, if you are a leader struggling with this aspect of people management – you aren’t alone, and you’re very human.

Moving past psychological barriers to lead conversations with courage and positive intent will set you up for success.  

If you are interested in knowing more about Clearway’s leadership coaching programmes reach out to Rebecca Mowat or phone 027 807 1533.