How to Have Difficult Conversations in a Digital World: 4 Tips to Consider

Jeff Cochran


Everyone has difficult conversations at some point in time. Whether we like it or not, the workplace is home to several difficult conversations, including conversations around pay and benefits, inappropriate behavior and under performance. Difficult conversations are often uncomfortable and unpredictable. However, they are also important and unavoidable. Having the knowledge and experience on interpersonal business skills such as difficult conversations, is an invaluable skill as a professional in any industry or place of work.

But what happens if we avoid the discussion altogether? Of course, not everything is worth your time — and avoidance is a legitimate resolution strategy in and of itself. If there is no clear path forward in which both parties may be satisfied, you may consider avoiding engaging altogether. Other times, avoidance may serve as a temporary solution until you can find another venue or engage in more effective means of conversation.

Consider these tips for having effective difficult conversations in today’s digital workplace.

1. Prepare

Preparation is the only time you have control in a difficult conversation. You can’t control the other person’s responses, emotions or feelings. Rather, work on thinking through, even writing down when possible, the most likely directions the conversation will take (i.e. objections they might make, questions they may ask, etc.) and how you will respond.

The best use of your prep time is to write a script for the conversation. This process starts with drafting out everything you want to say. After you write down your script, take a step back and read it again with a fresh but critical eye. Perhaps you should consider having someone you trust read it and play devil’s advocate. Finally, read it out loud to see how it all sounds and feels. Scripting your conversation and potential responses will make you feel more prepared, increase your confidence and improve your strategy.

Scripting and preparing is cathartic and helps keep your emotions in check. Keep in mind that you can prepare for their emotional outbursts, but you can’t control them.

2. Focus on What You Can Control

To help guide your conversation, focus on the elements you can control: setting and location. When engaging in a difficult conversation, address the situation privately. Having one-on-one discussions is what separates great managers from ineffective ones. Open communication can help you restore balance and avoid damaging your personal and workplace relationships. Being open and supportive of others helps you build trust within your team. By establishing a foundation of trust and safety, difficult conversations will be easier. Better yet, it can help you ensure continued morale and even peace in multiple areas of your life.

A challenging conversation, whether it is about an employee’s actions, growth, salary, behavior or another factor, should be done at a neutral location. Often, the initial anger or other high emotions you or others may feel at the onset of the discussion are connected with the current environment. Moving the discussion to a neutral location not only disconnects you from that emotional association but also prevents either party involved in the discussion from holding a position of power over the other. The resulting atmosphere is calmer, more comfortable for both, and much more able to lead to a constructive discussion. However, during a remote world environment, these tough conversations are most likely carried out virtually. If you can’t have the discussion in person, consider a face-to-face video conversation. Do not have a difficult conversation over the phone, email or an internal messaging system.

While most people focus their time thinking about how the other person will make a difficult interaction even more challenging, we should instead be focusing more on ourselves. Only you can control your preparation, state of mind going into the interaction and emotions during the meeting. Control yourself and your emotions, and you will be more successful in these difficult business interactions.

3. Listen and Keep Perspective

Once you present or discuss the issue at hand, be prepared to listen. Listening to the other person’s side is very important during a difficult conversation. Use active listening techniques to ensure the other individual you are not only listening but engaged with what they have to say. Give active feedback as you listen, including acknowledging what the other person has just said and affirming what you’ve heard; then, expect similar treatment as you respond.

Repeating important statements the other party has made not only reassures them that you are listening but also allows you to confirm what you’ve heard for your understanding.

Once both sides have had the opportunity to outline the issue at hand or discuss their perspective, you should reach a solution. Often, brainstorming together to reach a mutual solution can resolve the issue and benefit you both, whether this is setting goals or implementing a plan. If you can refrain from being pushy, collaboration can strengthen your relationship and enhance your opportunity to walk away from the conversation with an outcome that meets your needs. By working together on a resolution, this shows the other party you care about their position and outcome.

Finally, the most practical and actionable piece of advice when entering difficult conversations is to keep perspective: Take a step back and consider why this conversation is not that daunting after all. When you look back after years of professional and personal growth, you likely will have had tougher conversations, and possibly even will forget that this conversation took place at all. Keeping this perspective may help a difficult conversation become less daunting.

4. Don’t be Afraid to Compromise

In some cases, a solution where you both come away a winner is not possible. In these situations, brainstorming and collaborating can result in resolution without satisfying both of your needs. Instead, you must let go of one or more terms in favor of ending the tough discussion and moving forward. You can also use compromise to table the discussion until you can implement a more mutually beneficial, permanent resolution or find out more information. Often with remote work, we can’t get information as quickly as walking over to a boss or coworker’s desk. If you need to gain additional insight from another party, offer to follow up on the conversation.

As a boss or manager, determine whether the continued discussion is worth potential damage to your relationship or additional delays within the workplace and assess the associated cost of conceding some terms. If the situation is not of high importance to you, or a quick conflict resolution is more beneficial than achieving your original goal, accommodation may be an easy decision.

Learning to use these conversation strategies is just the beginning. You must also learn to deduce when each may become effective and when it is time to move on to a new tactic. It is crucial to consider all potential strategies in your efforts to maintain a peaceful and productive work environment.

By establishing a foundation of trust and safety, difficult conversations will be easier.