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  • Susan Snedaker

Quick Guide to Difficult Conversations

As a leader in any organization, you’re faced with having difficult conversations. It’s a part of the job most people dread, but there is hope. You can learn to become comfortable with difficult conversations. At some point, you might learn to enjoy them because of the positive impact they can have. Skeptical? Read on.

Road through the forest

Difficult conversations often feel like you're setting out down a dark, deserted road. With practice, however, you can learn to overcome your jitters and gain mastery over this crucial part of leadership. Difficult conversations at work typically come from one of four sources. Let’s break them down briefly.


Direct Reports

This is the most common difficult conversation you’ll have – with those who report directly to you. These conversations can be due to:

  1. The employee brings a complaint to you

  2. You have a problem with the employee’s behavior, attitude, or work product

  3. You have to deliver disappointing news (you were not selected for …)

Most managers dread these conversations because they are uncomfortable. Internally, most of us want to solve the problem quickly and move on. Some of us ignore the problem, allowing it to fester until it explodes and becomes impossible to overlook.


These conversations can be just as challenging as those with direct reports. You rely on peers in your organization to assist you with work at your level, to provide advice, input, or provide guidance from time to time. Often your work overlaps and you need to collaborate closely to get the desired outcome. Challenges in this area often are due to:

  1. Your peer has overstepped his/her bounds and impacted your work

  2. Your peer has failed to hold up his/her end of the work and impacted your result

  3. Your peer is consistently unresponsive, rude or controlling to staff (theirs or yours, same impact, different conversation)

Many people avoid having these conversations because it can be hard to get face time with peers to have these kinds of talks and because your work is so reliant on these peers that you risk having a lasting, negative impact on the relationship.

Your Manager

Talk about risky. It’s incredibly difficult to have a hard conversation with your manager, especially if you perceive your manager to be the source of the problem. These kinds of conversations often include:

  1. Discussion about your performance review, your pay or your promotion

  2. Concerns you have about your workload or the workload of peers (uneven distribution, plum assignments always given to the same person)

  3. Concerns you have about how your manager is managing you

These types of conversations are often incredibly nerve-wracking and perilous, depending on the managerial style and personality of your manager.

Your Executives

These types of conversations can be unnerving simply because of the power dynamic. Executives may be several layers higher in the organization, they may not be in your direct chain of command. Conversations like these are often:

  1. Discussions about decisions you made, results you have generated

  2. Questions about your area of responsibility (why did this happen, why didn’t you anticipate that)

  3. Questions about your thought process or methodology

These conversations often seem daunting simply because they are less common and they carry significant power dynamics with them. In some organizations, there’s also the political element to consider. Will speaking up or speaking the truth harm or benefit the organization? Your manager? You? Sometimes that calculation is complex.


There are tons of articles available on how to handle difficult conversations, but there are three steps you can take when approaching any difficult conversation that will help you gain mastery.

Remove the Emotion

The first and best advice is this: remove the emotion. Much easier said than done, but here are some tips.

Think through the situation from multiple angles.

Often a situation is viewed from just one perspective. I recall reading a story once about someone being infuriated by someone in front of them driving erratically. The car finally pulled over and it was clear there was a baby in the backseat that was having a serious problem. Suddenly the erratic driving had a root cause that sparked empathy instead of anger. Try looking at your situation from several angles to see if you can shift or reduce the emotion you feel about it.

Make up alternate stories about the situation.

This is related to the item above. Even if you don’t have any evidence to support it, make up some alternate stories to explain the situation. This does two things – it opens you up to the possibility that there may, in fact, be an alternate explanation you don’t know about and it also helps you reduce the emotions you feel by invoking other elements – curiosity, empathy, awareness, openness.

Put the situation in context.

It can be very easy to fall into the doomsday trap and assume this situation is enormous and overwhelming. And, some situations are. But many are not. Try stepping back and looking at the situation from a bigger perspective. Will this matter next week? Will this matter in a decade? Would someone else see this as a major problem? All these questions help you put the situation in context, which may reduce the emotion and anxiety related to dealing with it.

Identify Key Points

Once you’ve thought through your situation and reduced your emotions around it somewhat, identify the key points you want to make during the conversation. Usually three (or fewer) is a good number because you can remember them without copious notes. Also, the listener can attend to no more than three items, so adding more just creates noise and confusion. Work through your key points until they’re finely honed. Ensure they get to the core of the issue. Ensure they are well-worded. Ensure they convey the message you want the listener to get.


Finally, practice your discussion repeatedly. Repetition will do several things for you. It will help you hone your message and find the right words at the right time. It will help prepare you for the actual conversation, which reduces the anxiety of holding the conversation. It will also help you ensure the delivery goes as planned. Your words should not be accusatory or hostile or provocative. If you find yourself veering toward that, go back and address your emotions again. This may be an iterative process, but it can take place in the span of an hour or a day, when needed.

Having difficult conversations is a skill that can be learned and improved. As an IT leader, it is your job to ensure you become more comfortable with these kinds of conversations so you can address issues in a timely and effective manner – for the benefit of your organization, your team, and your own career.

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