Lead Artfully

How to have difficult conversations

May 13, 2021
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How to hold difficult conversations

How do you hold difficult conversations at work without creating a bigger mess or damaging staff relationships?  This article holds our top tips if you are struggling with not just how to “handle” these conversations but use them to lead more effectively.   Like most things worthwhile, the more you do it the easier it gets to achieve positive outcomes.


The ability to have difficult conversations at work that lead to positive outcomes is one of the most important elements of leadership.  How these situations are handled can lead to anything from transformational results to complete disasters.  Unfortunately, the sad truth is that tackling difficult conversations is far too often avoided.




Step 1: Identify your motive.

So, what is the core issue and what are you seeking to achieve?  Why do you need to have a difficult conversation? If you are the sole beneficiary of the conversation, then the chances are it is ego driven.  You need to stop and re-think having it at all.

However, when your intention is to resolve a behavior, work, or performance issue, then it should be easier to identify what you are trying to achieve.  Always try and find the positives!  That way you can re-frame the conversation from a “difficult” one, to a “coaching” one.




Step 2.  Plan, but do not procrastinate.

Plan out how you will have the conversation, but do not this as an excuse to delay or defer it.  In fact, prioritise to have it as soon as possible.   Problems left unattended grow.   "Difficult" becomes a lot easier if you plan it out in advance.  In planning, role play is a good way to prepare, and in your prep conside bouncing it off someone else first.  This is best done with someone not closely involved and who can keep confidences.  Change the names of those involved if necessary.   During the role play process think about excuses, reasons, or likely questions and how you are best to respond.




Step 3.  Pick the right time and location.

This might sound like a no-brainer, but privacy is key.   Having it in the middle of an open plan office space may not be the most prudent choice.  Show respect for the individual.  Use a private office, or quiet space away from prying eyes.  If they are a remote worker, ask them when they will have a moment alone for a private conversation.




Step 4. Have the conversation!

Now you have planned it out to at least some level, and have their attention in the right setting, here is some guidance to help you have an effective coaching session:

Stick to the issue and never make it personal.  Use simple language, stick to the facts, and give clear examples.

Be honest.  In many situations it is okay to show some vulnerability to break the ice.  Use phrases like "This is really difficult for me to raise with you, but I feel I owe it to you", "I feel uncomfortable raising this, but I must...", or, "Please forgive me if this comes across as harsh, as it is not my intention..."

Empathise by listening and getting their perspective.  Always treat others how you would like to be treated if the situation were reversed.

Try to disarm defensive or angry reactions.  No one likes to feel like they are being criticised so try and stay positive!  For example, phrases like “I need your help to understand...”, or “take a deep breath, and explain what you think is going on…” can be an effective way to disarm negative reactions.

Call-out passive-aggressive behavior.  Staff who are passive aggressive can be highly destructive to workplace morale and productivity. If you believe they are deliberately avoiding requests, gossiping, or not engaging with you fully then give clear examples.  Do not accept excuses but instead ask why they feel the need to act this way.

Keep confidences. Often these discussions lead to personal details that you may not have been aware of.  Disclosing these to others can instantly lose trust.

Let them know your perspective, or the perspective of others.  How they see the issue may be different to how others perceive it.  As a leader, it is your job to provide these insights.

Be open to new information.  The issue may in fact be not as it seems on the surface, so when faced with new information that changes your viewpoint do not be afraid to say so.  Also, if you need to go away assess new information, tell them.  You do not have to make decisions right away.

Ending the converation with positive next steps reframes the narrative.  Also, afterward I always sumarise the discussion in a private email to them, to capture the key issue and steps required by the staff member.  That helps set clear expectations you can both can refer back to if needed.



Further recommended reading:

Difficult Conversations: How to discuss what matters most - By D Stone, B Patton, and S Heen

101 Tough Conversations to Have with Employees - By P Falcone