Can We Talk? Approaching Difficult Conversations with Confidence

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You might have a coworker who seems unaware that he/she frequently interrupts you in meetings. Or perhaps there's an employee who isn't living up to your expectations. Or maybe your supervisor hasn't been supporting your professional development goals as much as you expected.

These are all stressful interpersonal situations to deal with. More importantly, none of them are likely to improve unless you initiate a difficult conversation.

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We decided to write this piece after recently facilitating the EDUCAUSE New IT Managers Institute, a two-day intensive program for managers who are in the first two years of their management careers. Topics covered in the sessions included communication styles, performance management, and managing up. As we discussed various scenarios with a room full of bright, engaged participants, it became clear to us that many of their biggest challenges stemmed from their uncertainty about how to initiate candid conversations on difficult topics.

Each of us has our own level of comfort with situations that involve potential conflict. Some are inherently upsetting—they leave us feeling sad, angry, or vulnerable. There are times, of course, when it may be more appropriate to overlook a minor annoyance than to confront a colleague. But when negative experiences become a pattern, avoiding the topic comes with a cost. When a problem doesn't get addressed, it persists. Our troubled interactions not only may become toxic to us personally but also can drag the performance and morale of an organization down. In addition, by the time a pattern has emerged, it can be harder to broach the topic, especially if we feel guilty or complicit for allowing the problem to fester.

What ultimately stops us from taking action? The underlying reason is usually fear in the face of an uncertain outcome, especially fear of a loss in social standing. The irony is that being a person who confronts difficult situations deftly is an opportunity to improve your social standing as well as your work environment. Especially when we are entrusted with a leadership role, it is precisely this sort of challenge that we must meet.

Another thing to realize, though, is that sometimes the resistance we fear is constructed in our own imaginations. As Ursinus College CIO Gene Spencer notes: "Less than half the situations that I assume will be difficult turn out that way. We need to ask ourselves why we think a conversation will be difficult. Why am I making that assumption?" Spencer suggests that we start by identifying a specific reason that we anticipate a conversation is going to be difficult. The answer may reveal more about our own anxieties than about the other person's character.

General Advice

Prepare (but Don't Overprepare).

When stakes are high, the likelihood of a positive outcome is improved with preparation. Albright College's Senior Director of IT Services Jason Hoerr reflects: "When I have been underprepared, conversations didn't accomplish what they needed to. That led to more difficulty." To keep the conversation on track, he likes to have a note with his top one or two specific point(s) written down and close at hand. This serves as a reminder to be specific and focused, but stops short of scripting his remarks.

Hoerr also suggests talking about the problem with a person who is completely removed from the current situation. "A mentor's experience, particularly outside your organization, is incredibly valuable," he notes. "I think too much verbatim rehearsal inhibits authentic communication, but hearing myself describe the issues also helps me to clarify what I need to say."

If you don't have access to a trusted mentor, you may be able to benefit from support inside your organization. Some matters are appropriately supported by your HR department, especially when confidentiality is required, such as a sensitive personnel issue. Some institutions even provide access to an ombudsperson or employee assistance program that can help you work through a complicated problem.

Ask for the Conversation.

Whenever possible, it is best to request the conversation ahead of time. This advice goes hand-in-hand with the importance of being prepared. It's critical that you avoid blindsiding a colleague. After all, the other person is more likely to participate meaningfully in the discussion if they know it's coming. Making the request also demonstrates your respect, which goes a long way toward setting a productive tone for the conversation.

Know Your Desired Outcome . . . and the Unacceptable Ones.

The point of having a difficult conversation is to bring about an important change. You don't want the conversation to stall at rehashing the past. Since you're the one who is initiating the talk, you should not only describe the problem but also explain your desired outcome. This will reorient the conversation around how things can be better in the future.

Even when our counterparts respond in good faith, they may disagree with our perspective or be unable to deliver the outcome we seek. Hopefully, you will be able to find some points of agreement or discuss a compromise solution. Understand that this is not a failure. Compromise and negotiation are signs of engagement. A more discouraging response would be apathy.

If an acceptable outcome can't be achieved right away, remember that your relationship with your colleague is likely to continue. We discourage resorting to an ultimatum, which limits conversation and may box you into a corner. Instead, be clear that you're not satisfied with the outcome and suggest a time to resume the conversation, after allowing both of you some additional time to think.

Make Sure That You're Emotionally Centered.

You don't have to close off your emotions. In fact, it's a good thing to put a name to the emotions you're feeling. But inability to control negative emotions runs the risk of overshadowing the important subject at hand. If your emotions in-the-moment interfere with achieving the outcome you're seeking, they become counterproductive.

Take the Communication Style of the Other Person into Account.

As we discuss in the New IT Managers Institute, everyone's style is different.  For example, some people prefer direct language and concrete examples, whereas others might respond more favorably to a conversation that contextualizes an issue within the larger picture for a project or unit. Although it's important to be aware of differences in communication styles, you should be careful not to be paralyzed by the need to be flexible. These conversations are just that: conversations. Be ready to listen to your colleague during this discussion, to respond to him/her as it unfolds, and possibly to adapt your approach as you go.

Be Fair.

The most lasting changes in any potential disagreement arise when we are honest and are authentically ourselves, and when we then allow our conversational partner the space to be open and honest as well. Ask open-ended questions such as, "How did things look from your perspective?" Be respectful. Listen to the answer and don't interrupt. This isn't just a matter of being a decent person. Your colleague may know something that is in one of your blindspots. You might even be wrong.

Some people will not immediately reciprocate your candor. In that case, note your observation without making it an issue of their character. You can signal your concern with a statement such as: "I still feel like I don't have the whole picture. I really want to understand. Can you help me?"

Remember that if the person feels manipulated into complying with your wishes, you haven't really brought about the change you're seeking. You desire collaboration, not compliance.

Know When You Need Help.

There is a difference between a difficult conversation and a genuinely risky one. If the situation involves bullying, harassment, or other serious misconduct, you should seek assistance without delay. First, write down, with specific details, the facts that you have observed. Next, seek out assistance from your HR department or other appropriate point of contact in your organization. You may still have difficult conversations in your future, but you should not face them alone.

Advice for New Managers

When you need to have a difficult conversation with somebody who reports to you, it's important to keep the power differential in mind. A detail such as where the meeting takes place may not matter much to you, but it can subtly shape how the other person feels. Is it in your office or theirs? If it's in a neutral space, is it a formal conference room or in an informal walk across campus? There is no single right setting for difficult conversations, but it behooves you to do what you can to choose a setting that improves your supervisee's sense of safety.

For new managers, conversations about missed expectations and job performance can feel particularly awkward.  Moving into a role of providing performance-oriented feedback marks a significant step in one's career.

Remember that as a manager, you have the responsibility to keep the team and its work on track and in alignment with your unit's mission. If your institution has standard HR steps and documents for the performance review process, use them. Relying on such documents to shape potentially challenging conversations might seem unnatural at first. However, they can provide a sound framework for objective discussions about performance. In addition, standard documents such as job descriptions and work plans are essential in performance-related conversations.  These documents can help you keep the conversation focused on objective, measurable outcomes related to expected performance.

The impact of behavior issues on performance can be more difficult to quantify and therefore more difficult to address. In these conversations, it can be useful to describe the behavior you observed and to explain how you interpreted it and the effect you observed it to have on you or others. This approach depersonalizes the conversation and, hopefully, helps to mitigate emotional responses. It may also provide your staff member the opportunity to share additional insight about the situation—insight that could provide you with a fuller picture of the context. As with all challenging conversations, understanding your goal is essential. Do you want the person to change his/her behavior? Or will it suffice that the person is aware of the effect of the behavior?

Your long-term goal should be to create an environment of trust. Remember, you don't simply want people to receive your feedback more openly. You also want to be a manager whom others trust enough that they will be completely honest with you. Gene Spencer remarks: "I've heard lots of people say 'I have an open door,' but that doesn't always resonate with everyone. I think it is important how accessible you make yourself to the people around you." He adds, "You send subtle messages about how open you are."

For Further Exploration

There are many resources about difficult conversations, most notably Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler's multimillion-copy seller Crucial Conversations: Tools for Talking When Stakes Are High. The Harvard Business Review also produces articles on the topic of difficult conversations.

The EDUCAUSE Institute offers a variety of programs for new and established managers to enhance their management skills. The following two programs meet in a compressed format but yield high returns in terms of knowledge-building and peer-networking experiences:

  • If you are a new manager or have been managing for up to two years, register for New IT Managers Program at Connect in Portland (March 13–14, 2017) or Chicago (April 10–11, 2017).
  • If you have been managing for more than two years and up to five years, register for the EDUCAUSE Management Boot Camp also at Connect.
  • If you have three to five years of managerial experience and would prefer a more immersive, week-long experience, consider registering for the EDUCAUSE Management Institute. For 2016, this Institute will take place June 27–July 1 in Austin.


We would like to thank Gene Spencer and Jason Hoerr for agreeing to be interviewed for this article. The videoconference interview took place on May 10, 2016.

Eric Behrens ([email protected]) is associate chief information technology officer at Swarthmore College.

Heather McCullough ([email protected]) is associate director at the Center for Teaching and Learning, University of North Carolina at Charlotte.

© 2016 Eric Behrens and Heather McCullough. The text of this article is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.