4 Tips for Having a Productive Conversation with a Challenging Employee

I cannot tell you how many times a day I hear about, or experience challenges with staff. All of us are so different, with such different experiences, stories and perceptions – it’s amazing we EVER have a productive conversation in which both people understand each other! Employees will always be one of our biggest challenges. That said, there IS a more productive way to have these conversations:

1. Get real, with the real person!

So many of us talk to others about a challenging employee, instead of talking TO the employee about themselves. It’s really not fair to expect someone to change their behaviour or results if you don’t make it very clear and straight-forward for them. Don’t bite your tongue, and walk away only to “vent” to someone else. Get real in the moment and tactfully find a way to tell that employee what you’re really feeling, such as: “I feel that you need to work on your communication; attitude; finishing what you’ve started; etc.”

2. ASK THEM what is going on for them and LISTEN!

We absolutely cannot help to solve a problem or remove a barrier for an employee if we don’t understand what is happening from their point of view. Ask them to share with you: what it wrong? what is going on? what do we need to change? How can I help? and then…. just shut your mouth and open your ears. Sometimes you have to sit in silence for a while, but eventually they will share. And when they do, LISTEN. Listen for real –  listening for real means listening with the possibility of having your mind changed.

3. Use your tools

They should have an incredibly clear set of documents, which you can reference during coaching, that will ensure employees have the very best chance of succeeding and getting on board. Job descriptions, KPIs, procedures, policies and culture statements are powerful tools to use for coaching; remember to remain kind and supportive, but FIRM. Let those tools do the heavy lifting, and make sure the employee understands what is ok (for example “feeling frustrated is acceptable) and what is NOT ok (for example “yelling or swearing is NOT acceptable).

4. There must be consequences

When you tell an employee something is unacceptable, you ask for their side of things and try to solve their problems, you use your tools, and they continue to break the rules/misbehave – if no consequences result, you will not see positive changes. In fact, you may even LOSE good employees with this type of situation, because good employees see you letting that difficult employee “get away with it”.

Solution: implement progressive discipline, and use a verbal warning for the first offence, a written warning for offence 2 and 3, and terminate the employee if the behaviour still continues. You should always remain kind, calm and supportive, but if an employee is not willing to get on board with your culture, your goals, your mission and WHO YOU ARE as a company, you must implement consequences – in the form of progressive discipline. Your progressive discipline policy should be introduced to all staff when they are hired, along with your other policies.


In most cases, you will solve your problem AND become closer with the person you choose to have a conversation with. Remember, if you don’t have the conversation, you can’t expect things to change.


If you feel you need some help increasing your profits, contact TMH Business Coaching and Consulting today for a confidential, free, no obligation consultation to propel you forward. Also, please feel free to add yourself to our weekly coaching tips email!

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Kelli-Rae Tamaki

Kelli-Rae is truly passionate about successful business, and believes it can always be better, which is why she has spent 22 years studying, running, coaching and consulting with businesses, just like yours.
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