7 Ways to Turn Those Cringe-worthy Workplace Conversations into Constructive dialogues

Whether you are leading a team, a department, or an entire organization, you must find yourself unceremoniously chucked into the pit with employees, stakeholders, or clients to have those tough conversations.

It falls upon you as a leader to make these challenging conversations as mutually beneficial and productive as possible, which can be rather tricky if you don’t know how to approach them the right way. A survey revealed that 70% of professionals, be it managers or employees, show a aversion to tough conversations in the workplace, even though companies spend a fortune into developing their people.

Whenever you face a sensitive topic at work which is sure to touch nerves and ruffle feathers, here’s how you can make those nerve-wrecking conversations a little less intimidating and a bit more constructive.

Know Your Own Stance

Before stepping into the conversation, make sure to process your own upset, positions, beliefs, and opinions. From the offset of the conversation, share your intent and the outcome are you are expecting. Ask plenty of questions and reflect back what the other person is saying so that they feel heard. The key is to listen for accuracy and not assumptions.

Foster Dialogue

Delicate situations require empathy, preparation, and patience. If you are approaching a sensitive topic, come to the table well-informed so that you can support your comments with hard evidence and prevent heated opinions and discords. Instead of using coercion, share the facts and premises that helped you arrive at a conclusion, and calmly explain the logic you used to get there.

As a leader, you need to present your case in a “vulnerable, honest, and patient way” and stay open to being challenged. Even if you are firmly believe that you are right, be willing to listen and encourage your employees to challenge your judgment and argue the point to conclusion. Just remember to keep the conversation on track and not let other matters or previous grievances rear their heads.

Exhibit Empathy

Humans tens to view all situation through their personal lens, instead of putting themselves in anybody’s shoes. As a leader, you need to check your bias and approach the conversation with empathy and respect. When handling challenging conversation, try your best to see the problem from the other person’s perspective to better comprehend their stance. Then, begin the conversation from a place of caring. Express your concerns and let them know that you care about their well-being.

Leave Your Emotions At The Door

Tough conversation can easily become emotionally-charged, so both parties should do their utmost to keep their emotions in check. Stick to cold-hard facts, instead of adding biased emotional elements to the conversation, such as “I am disappointed”, or “this is not how I feel like about it.” If the other party finds it hard to keep a cool head, pause the meeting and ask to reschedule. These tricky situations need to be diligently navigated.

Use A Tailored Approach

All successful leaders know how to tailor their approach to the individual they are communicating with. You cannot have a one-size-fits-all response to tricky situations and delicate matters. You need to gauge the mental, emotional and physical state of the person you are conversing with. When addressing a problem, stick to the employee’s behavior and how it is impacting others, rather than focusing on the person itself.

 A successful leader is able to say the same thing very differently to their board of directors, a peer, a midlevel worker, or a line worker, using their knowledge base and their language and tone. Spend some time to know your audience, before you go in for the kill.

Stay Positive

The key to a successful dialogue is to stay positive. Your employees are more likely to get defensive and argumentative at the first hint of negativity. Instead of just ranting on about all the things they are doing wrong, Give them examples of positive things they can do to improve and offer them the tools and resources that they can use to bring about an improvement.  

Avoid language that insinuates they are in trouble, such as a “disciplinary meeting” or “verbal warning.” Start off with candid questions, such as ‘How’s everything going?’ ‘Can I have a minute to discuss some feedback we’ve received about your behavior?’ to open lines of communication. In addition to making them feel accountable, your meeting should end on a positive note.

Plan But Don’t Script


While it helps to plan what you want to say before entering the conversation, don’t go the extra mile to draft a script. These conversations hardly go according to plan and no one can predict where the conversation will lead to. Your counterpart has no lines, so chances are that you will be left at a loss for words if they go off script. Rather, aim to maintain a flexible conversation, but do keep a stock of possible responses for those tricky spots. Your language should be simple, clear, direct, and neutral.

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