Difficult Conversations at Work: Strategies for Success

Difficult conversations at work are unavoidable. Whether you’re addressing performance issues, providing feedback, or managing client conflicts, these conversations are important to maintaining healthy relationships and fostering growth. However, approaching these conversations can be uncomfortable and intimidating. In this blog, I would like to share my insights and personal experiences on handling challenging conversations at work professionally and tactfully.

1. Prepare and Plan:

Before having a difficult conversation, preparing and planning your approach is important. 

Following points will help prepare for the conversation:

1. Take time to clarify the purpose of the conversation.

2. Outline key points you want to address.

3. Anticipate how the conversation will go and prepare responses for it.

4. Prepare documented proof, if any, required for the conversation. 

5. Choose a timing and setting for the conversation to make sure you have privacy and minimum distractions.

By preparing thoroughly, you'll feel more confident and better equipped to navigate the conversation effectively. In my experience, preparation is the key to successful difficult conversations. I always take the time to gather information, rehearse my key points, and consider the other person's perspective. This helps me stay focused and composed during the conversation.

Pro-tip for Managers:

If your difficult conversation involves layoff or poor appraisals then please show empathy.

Times have changed. Employers no longer have too much power over their employees.

A good employee will get hired elsewhere.

So make sure your strategy is less power play and more empathy to identify a middle ground.

Additionally, an employee's loyalty is first towards their own family then your company.

Do not take offence when they make a choice of moving away from your organisation. The smoother you make the transition the better chances you have of inviting the employee back to join your organisation in the future.

2. Focus on Facts and Behaviour:

When you engage in difficult conversations, it's important to focus on observable facts and behaviours rather than making assumptions or judgments. Be specific about the issue at hand and give concrete examples to support your points. Avoid criticising or blaming and approach the conversation as an opportunity to grow and improve. I believe that approaching difficult conversations with a focus on facts and behaviour helps keep the discussion objective and productive. By sticking to observable evidence, I can address the issue directly without making the other person feel defensive or attacked.

An anecdote from my experience:

Only twice have I been assigned candidates who I had to escalate. But before escalation I followed the following steps in both cases:

1. The first time they made a mistake, I guided them on how to go about solving the issue. Also encouraged them to take help from peers or reach out to me in case of doubts.
   

2. The second time they repeated the mistake, I took them on a separate call and asked whether there were any personal or professional reasons that were causing them distress and affecting their work? Now here you either catch them in a lie or identify if they are being genuine. A lie requires you to call them out on it and be confrontational. A genuine issue might need you to be empathetic and provide them more time to get required results. Individual managers should make this decision for themselves.
   

3. The third time they repeated the mistake, I escalated them and tried to identify if this is a repetitive behaviour since joining the organisation or is this specific to me. 

In both my cases, the people I escalated had shown negligence in the past and were never able to give me a good enough reason not to escalate. In fact they were a bad influence on the rest of the team. Escalating them and eventually moving them to a different team set a standard for the rest of my team to keep doing good work rather than pick up on bad behaviour.

As I made it a point to reprimand them as and when they were wrong there was less ambiguity about what they did. I had enough evidence to back me up. Other team members saw that I was fair and that I gave multiple chances. Acceptable group dynamics prevailed.

So do not be afraid to take action. How you conduct the conversation is important.

You will notice that I have approached the difficult conversation with empathy before confrontation

3. Active Listening:

I’ve spoken about active listening in a previous blog. Listening is a fundamental aspect of communication, especially during difficult conversations. One can practise active listening by paying full attention, maintaining eye contact, and trying to understand the other person's perspective empathetically without interrupting or jumping to conclusions. In challenging conversations, I prioritise active listening to make sure that the other person feels heard and valued. By listening attentively, I can build rapport and trust, which is essential for resolving conflicts positively.

We all have tough days. We have messy relationships or lose people or have financial troubles or fall sick, and through it all we have to show up at work and do our jobs. Sometimes just listening to someone’s challenges gives you an insight into how to deal with that person. Most people want to do good work. They want that promotion. They want better pay. But most of all they want peace of mind while going through life. Some flexibility that we can provide might be what they need on a given day. Be that person who makes that call and covers up for a colleague or team member in their time of need.

4. Show Respect:

Remaining calm and professional during difficult conversations is important. Stay focused on the issue at hand and avoid giving into personal attacks or escalating conflicts. Be respectful no matter who you are speaking with a manager or a junior. Maintain a professional demeanour, speak respectfully, and do not use anger-driven language or gestures. Follow the above and be instrumental in maintaining positive relationships and finding constructive resolutions. I always remind myself to remain composed and focus on finding solutions rather than dwelling on personal emotions.

That also doesn’t mean you let someone else walk all over you.

Pro-tip:

Maintain an excel and write down all the tasks you do on a daily basis.

This comes in handy during appraisals. If you do not agree with the feedback you can politely direct your manager to certain points on the excel where you have showcased that skill. But do follow it up with, “Do you think I could have handled it better?” or “Is there a way I could have addressed it better?” This opens up the conversation for discussion while showcasing you did the best you could with what knowledge you had at that moment.

Keep all your conversations on email.

Send out emails to clarify the action items.

Send out an email to delegate tasks.

Send out an email to make sure your managers know what your workload is so that they can help you prioritise tasks better.

And I mean email. Not slack. Not on teams. No other texting app your organisation uses.

It has to be on email.

This isn’t to show lack of trust. This will in fact show transparency, accountability, and ownership on your part. You are avoiding any miscommunication so that everyone involved is on the same page.

5. Collaborate on Solutions:

Approach difficult conversations as an opportunity to find solutions and move forward positively. Encourage open dialogue, brainstorm together, and definitely be willing to compromise if need be. Focus on the common goals and mutual interests you have to reach a resolution that satisfies all parties involved. I personally prefer approaching difficult conversations with a collaborative mindset because it fosters a sense of ownership and accountability among all stakeholders. By working together to find solutions, we can overcome challenges more effectively and strengthen our working relationships.

Pro-tip:

If the conversation gets heated, suggest scheduling a call for the later that day or the following day. In the mean time, all participants can cool off and come back to the table with some ideas on possible compromises.

This will reduce the possibility of having bad blood among the participants.

It will also show how mature you are to know when it is time to call it a day.

Conclusion:

Difficult conversations at work are inevitable, but they don't have to be scary or destructive. By approaching these conversations with preparation, focus, active listening, respect, and collaboration, we can navigate them successfully and turn them into opportunities for growth and positive change. Remember, difficult conversations are an essential aspect of professional development and relationship building, so embrace them with confidence and resilience.