Urgh. How to have less-horrible difficult conversations.

A client and I were discussing hiring tactics this week, in particular interview questions. Skills can be easily assessed, what's far harder is personality. After all, everyone is putting their best self forward during the interview process and you will never actually know what they're like to work with until, well, you work with them.

This conversation prompted me to think back to some of the people I've not loved working with (to put it mildly) over my career. Two in particular stand out. One was just harsh, all round and everyone accepted that. But the other was the more challenging, because on the surface they seemed fine, positive even at times. But every so often they would just "go off" at someone or at a situation, in a way that was anything but professional. It was intense, bullying and sporadic in a way that kept everyone around them on edge. You never quite knew what to expect or what would set them off. I was their manager's manager and they had issues with this particular manager (mainly as they wanted that person's role, their manager was absolutely fine and a great person to work with) so I would often have to play the middleman when things were tense. One morning, on the drive in, I called my brother, Dr. Eóin Killackey, a professor of psychology and practising psychologist (and great person to have on call anytime) and asked for help. What he said then has stayed with me in the many years since.

He reminded me that everyone has a filter, made up of their experiences, background, education and so many other parts of their life. They use this filter to perceive what's happening around and to them. You have to remember that when you're saying something it moves first through your own filter (and expectations of what you think should happen as a result of this conversation) and then through their filter (and their own expectations and defenses about what's being said). He also reminded me to cushion things. I can be a pretty direct person at times and he cautioned me to always open and close (an mail, a conversation etc.) in a positive manner that promotes trust, empathy and understanding. It was great advice and has helped me in many, many occasions (personal and professional) to stop and take a minute to consider how someone else may be taking in what's happening.


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2020 has been an incredibly difficult year for many small business owners and with the influx of challenges comes the need for difficult conversations. Many of my clients have had to reduce staff, some have had to find alternate suppliers and others have had to figure out how to make working from home + homeschooling + relationships work. For you it may be different. It may be an issue with a supplier or manufacturer, it could be asking customers or clients to have more patience, it could be having to let staff know that their position is being made redundant, it could be asking staff to change their ways of working or making super clear what a staff member isn't doing well or it might just be having to keep the peace in your own home as everyone figures out how to work and learn in new ways. None of these are "fun" conversations and few of us, regardless of experience, would enjoy having to have them.

My brother was so helpful years ago when I was faced with this very challenging person and so I spoke with him this week to ask what he — a psychologist – might say to small business owners, right now, who are having to have difficult conversations.

Here's what he told me:

"Hard conversations are hard — that’s the first thing to remember.

Some important things to think about are:

What do you want to say? Consider this in advance, maybe even write it down.

Have clear statements that explain the reasons why this outcome is happening.

Acknowledge that it is hard for the person on the receiving end.

Don’t get sidetracked by emotion from the other person — remain calm and on message.

Keep this about the reasons and not the people. Even if the other person tries to make it personal.

Do it in person if you can, or by phone or video call. Text or email is a last option when it comes to personnel. (It may be ok for suppliers depending on the history of the relationship and the potential there may be for picking up the relationship if things improve).

Finally I guess as a boss, this is the most difficult element of being a boss. But some of the people you have to have difficult conversations with, or even say goodbye to now, will be their own bosses down the track. Think about what you would want them to take and learn from this experience if they ever have to be in your shoes."

No one is immune from having to have difficult conversations. By working through the ideas above, we may just save ourselves and the person we're conversing with a whole lot of stress, anguish and resentment.


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