How To Lead Effective and Difficult Conversations With Coworkers

Difficult Conversations – We Can Work It Out

We have all had to be involved in difficult conversations at work. Regardless of which end you were on, the experience was likely uncomfortable and a little painful. 

You are not alone. Difficult conversations are unpleasant and feel unnatural.  We prefer easy-going and happy relations. We want to feel good around our coworkers, and them to feel good around us. 

Conflict doesn’t appeal to anyone—especially in the workplace! And for many of us, we prefer to deal with conflict by avoiding it altogether. Any other ‘avoiders’ out there? (I have often thought “let me outta here ASAP!)

Conflict Avoidance

The problem with conflict avoidance is that the conflict escalates – more and more people get involved, and overall anxiety increases. It’s a hard lesson to learn, but most of us have discovered that avoiding a problem does not make it go away.

It’s Not All Bad News

Fortunately, there are things we can do to make difficult conversations meaningful. 

Let’s talk about some tried-and-true tips for effectively approaching difficult conversations at work and possible ways to make them a positive and productive experience for the parties involved.

By learning to effectively handle difficult conversations that produce the best possible outcome for all parties, we gradually change how we (ourselves) think about these conversations. We shift the narrative from difficult to beneficial and unpleasant to positive.

Do Your Homework Before a Leading Difficult Conversations

Being adequately prepared is critical. So, the more you prepare, the higher the likelihood that the conversation will go well. 

If you ask others to participate in a problematic discussion about something when you do not know all the facts, ignorance alone can produce a negative outcome. Emotional disruption is sure to follow and complicate the situation further.

Emotional Aspects of Confrontation

Humans are complex beings. We may think we are logical, and all our conclusions are logically calculated, but you and I know better! 

Difficult conversations can become emotional conversations. It’s hard to prepare for a successful outcome when emotions are front and center because they don’t follow a logical path. Instead, people get triggered and respond defensively. 

Laying out the facts objectively and calmly reduces the possibility of an emotionally charged discussion.  

If the situation requires you to produce facts to prove something, you should have that proof with you and be prepared to show it. Remember, one of your objectives in the conversation is to maintain a professional tone that relates to all parties as balanced and at ease. Looking at things from a fact-based standpoint helps to facilitate this.

Take care of the way you express yourself. Your manner, tone, words, and phrasings,  along with your body language are important. 

Watch Your Semantics

Try to avoid using the “I” language because brings a particular bias to the conversation. For instance, instead of “I feel” or “I believe,” opt for “it seems” or “would it be correct to state?” 

If it becomes evident during the meeting that emotional reactions are amplified – you might want to postpone further discussion until all involved have a chance to “reset.” 

Start with a Goal in Mind

Engaging in difficult conversations without a planned outcome can potentially backfire! People might feel like you wasted their time for nothing. You don’t need a script or formal outline, but stating the results you expect to accomplish together will be helpful for you as you guide the conversation, and for the participants to stay on track with the issue at hand.

The goal with difficult workplace conversations is to arrive at a solution that will hopefully work for everyone. Ideally, all parties should be involved in brainstorming ideas and contributing to the solution. 

Note this: If you can all agree on the problem, you’re halfway closer to solving it than if you do not.

Turn the Conversation Into A Dialogue

Your difficult conversation with a coworker(s) should seem more like a dialogue than a monologue. Feedback and open discussion will keep the conversation civil and, hopefully, fruitful.

Is there a possible agreement? If not, then why not? 

Helping other people hear their own WHY NOT when you ask them “why not?” – can help people identify if their own emotion, frustration, or defensiveness is clouding the issue.

So don’t interpret the first round of disagreement about the issue as a bad outcome. You are getting somewhere! People are talking with one another, hopefully listening to other points of view, and finally, letting out in the open their reasoning – faulty or not.

Successful outcomes to difficult conversations require patience and a willingness to go the distance to reach your intended outcome.

Ask Questions

You should also be genuinely curious and not apprehensive about asking questions. When we demonstrate curiosity to learn more about a particular situation, it conveys our willingness to be genuine and honest; and find the right solution for everyone.

The Rewards are Ongoing

Successfully managing and resolving a challenging work situation will improve your relationship(s) with the parties involved. By focusing on the positive (identifying the problems and finding solutions) and minimizing the negative (the effects of the issues), you help others succeed and grow – a leadership trait people count on.

Don’t Beat Around the Bush

You can appear insincere if you skirt the issues and speak in abstract terms. Likewise, if you talk as though you already know who is at fault or have made up your mind with consultation – expect difficulty in an effective resolution.

It’s best to be direct with your communication. Know what you want to say, say it carefully and keep an open mind. Speak with a calm cadence, don’t rush to make your point, and then wait (allow others to absorb and monitor themselves) in silence for a response.

Remember that it’s possible to be direct without being insensitive and that you can get to your point respectfully without hemming and hawing.

Put Yourself in Their Shoes

 I have written much about empathy and compassion, so it’s no coincidence that I feel the need to touch on it again. 

 When we show that we understand or feel what the other person is experiencing during a difficult conversation, we show that we are in it together with them. 

 Regardless of the scenario, consider (I would go as far as to say – strive to know) how your coworkers are feeling—especially during a difficult conversation. If you notice they are experiencing difficulty processing some or all of what you said, they seem emotional or stressed; allow them sufficient time to gather their thoughts.

Try to present your side of the conversation in a friendly, open-minded fashion and always focused on resolution. 

Approach the Situation Positively

A final word on positivity.

If you allow yourself to begin the conversation with your own pent-up emotion or anger, it will be challenging to keep the conversation from going south.

It all starts with your resolve to be authentic, honest, respectful, and compassionate. 

A negative approach often results in defensive and argumentative reactions from your coworkers, wastes everyone’s time, and likely deepens the conflict or unwanted behavior you are trying to resolve.

 Think about it like this: If it was you receiving the confrontation – how would you like things said to you? 

Create the Energy

One way to have positive energy in any meeting is to create it. 

Go into the meeting with confidence that it will go well. Bring the energy with you! By approaching the difficult conversation, you are about to have positively, the energy you bring will also be positive.

These difficult conversations are never easy. I am not going to sugarcoat them with rose-colored glasses. But they can be less awkward or painful and more pleasant and productive if you put in the work; before, during, and even after. You’ll be glad you did.