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January 12, 2016 - No Comments!

How to Conduct a Difficult Conversation

It’s a fact: addressing situations that result in disagreement or tension can be stressful. No one wants to handle them, but sometimes we’re put in positions where we just have to. The thing is, these conversations do not have to be difficult if you prepare yourself for a positive outcome.

Prepare yourself.

It’s important to know what you are getting into when you address “difficult” conversations. While you don’t want to script your conversation and get your mind set on one outcome, you do want to have an idea on how you will handle the conversation and its possible outcomes—both positive and negative.

Read The Anatomy of a Difficult Conversation to gather tips for preparing yourself for the best, and remember, it’s your job to keep a healthy, positive attitude while trying to address the issue. It’s easy to get worked up and upset, but at the end of the day, that will only stress you out more and show the other parties involved that you’re not equipped to stay cool.

Impromptu Conversation or Scheduled Meeting?

As soon as you’ve done your prep, you will be champing at the bit to just get the conversation over with. Maybe that’s because you’re eager to resolve it, maybe it’s because the stress of the situation is eating away at you, or maybe it’s because the situation is getting worse. No matter the case, you won’t want to spend too much time planning. Get to it and resolve the issue.

Impromptu Conversation

There’s something nice about approaching someone briefly and just saying, “Do you have a few minutes to chat?” In general, it feels very non-confrontational and in some way, it minimizes the tension of the situation. So, use your judgment, but if you’re trying to resolve an issue quickly and you think you’ll be able to “grab” someone for a quick chat, do it.

Before you do, make sure that the other person is the type to be okay with being approached like this. Remember, a lot of people live and die by their calendars. An impromptu meeting could throw them off and upset them.

Scheduled Meeting

There is no doubt that scheduling a meeting will send a message. Many organizations require an agenda for any meeting scheduled—and many people would want to know what the meeting is for anyway.

Be sure to think this through: will the person or people you’re going to meet with react negatively if they know you’re addressing the situation? Depending on the person or the situation, extra time to mull over the issue could make it even worse.

No matter what, the best path is to be 100% honest about the intent of the meeting. Keep a positive tone and express that the intent of the meeting is to discuss an issue and resolve it—together. The language you use and how you position the meeting will most definitely impact the mental states or attitudes people will go into the meeting with.

Not sure how to handle it? Here are some traits or questions to consider when deciding on your approach:

  • What is the level of intensity of the situation? If it’s one that could cause someone to be fired or to quit, you will most likely want to call an immediate, impromptu meeting.
  • How well do you know the person or people? Personalities play a large role in how you handle these interpersonal situations. If you know the person and feel a more relaxed approach will work, call an impromptu meeting.
  • What’s your workplace culture? If you call an impromptu meeting, can you run out together for a coffee or lunch? Or will you have to stay in the office? Where the meeting takes place can certainly impact how people feel about it. Keep in mind, while a formal atmosphere may feel necessary for more serious situations, a relaxed atmosphere—like a coffee shop—may be more conducive to conversation and working out an issue in a relaxed, friendly way.

You will need to pick an approach, time, and format that you feel will work best for the situation and the people involved. Sometimes you’ll get it right, sometimes not. No matter how you handle it, admit mistakes and stick to your decisions and work hard to resolve the issue.

Meeting Means Talking and Listening

As soon as you’ve pulled everyone together—whether it’s a one-on-one or group meeting—establish the purpose of the meeting. You are together to resolve the issue. In order to get there, express the desire to have everyone be happy and heard, not just to avoid interpersonal issues or conflict, but for the health of your work.

These meetings can bring on a level of stress that makes people uncomfortable, so they often do not realize that their personal opinions and emotions can get in the way of a productive outcome. When they do get in the way, work and working relationships fail. So express a goal that everyone can agree on: to speak freely and be heard.

Start with a general description of the issue. Keep it high level and don’t add color commentary to the story. State the facts and follow them up with ground rules for your meeting:

1. The purpose of the meeting is to resolve the issue at hand.

Issue management can be confusing. People have opinions to be heard, and they’ll vary. Facts will be hard to check or verify, and you’ll sometimes feel like you’re caught in a web of disaster. Nevertheless, you can stand in the middle and ensure that everyone is heard and that each story, point, or argument leads to a resolution.

First, end the issue right then and there. Turn the focus from finger pointing to resolving. You want the team to know that the issue has ended and that you’re in this meeting to end it together. Additional finger pointing or arguing will only make the issue worse and drag out the outcome you want and need.

2. Speak now or forever hold your peace.

The environment of this meeting is one of discussion. In order to keep a positive attitude about a resolution, everyone will have a chance to be heard.

Do your best to moderate the meeting and make sure that all parties have a chance to speak up. This may mean that you go around the room and have everyone state how they feel about the issue. Or maybe you will bring in an outside moderator to ensure that all parties are being vocal (they could do the job of calling on people and asking them how they feel).

However you handle it, be sure to consider all parties and where they sit in the situation. Some people will be heated and will speak up. Others will be quiet and just listen. Try to maintain a balance and allow everyone to weigh in, but don’t cut anyone off. When you close the meeting, be sure that everyone has said their piece. If they haven’t, you’ll open the door for additional issues or resentment to creep in.

3. Listen up.

Establish a modicum of respect. Everyone will not only have a chance to speak, but everyone is expected to listen. This means no cutting people off, no side conversations, and no questions unanswered.

Again, you might want someone to moderate this conversation if you’ve got a larger group. If that’s not possible, do your best to keep the flow of conversation headed in the direction of an outcome. Don’t let one person dominate the conversation and don’t let an issue go unaddressed.

Conversations can wind ten different ways with one comment. If you feel as though things are getting off track, keep notes or track issues mentioned on a whiteboard that everyone can see. This will ensure that everyone is not only given a chance to speak, but that their issues, large or small, are being heard.

4. The meeting will not end without a resolution or a plan for one in place.

If you truly want to address the issue, you must come up with a resolution for it. This is the point of your meeting, of course. Moreover, you want to come to an agreement as a team. As you circle the issues through conversation, ask “How can we resolve it?” of the attendees or suggest solutions as you see fit.

Letting attendees know that this meeting is not just a venue to complain, but one to resolve the issue at hand—together—will greatly impact the way your conversation happens. This is especially true if your meeting is taking place with limited time. So, maybe think of a rough agenda for the discussion. It could look something like this:

1. Identify the issue.

2. Discuss the outcomes.

3. Team decides on solution action plan.

4. Discuss the next steps.

Keeping focus on the outcome will help you to stay on track. If you give the group a goal, they will focus on the solution more than the problem.

Use Thoughtful Language

The way you express your emotions, describe facts, and even interact with others in this meeting will impact the course of the conversation.

Disagreements are tricky, because they might be about a hard and cold fact, but emotions always come in to play. As humans, we express our feelings in different ways. One person might show outright anger through harsh language, while another might be calm and collected but express the same ire. Either way, be mindful of your language and how it could be perceived.

Inclusive language shows the team that you are invested in resolving the issue with them, not for them. It also shows that you are dedicated to rebuilding the trust of the team and strengthen the bond of the working relationship. No matter how it ends, you want to share a common feeling of respect and dignity, and that can be done with using words that are:

  • Inclusive of everyone: we, us, our, team
  • Polite: please, thank you, excuse me
  • Solution oriented: next steps, solution/resolution, plan

Finding the Right Solution

Discussing (or complaining about) issues is easy. Finding solutions that work for everyone can be difficult. Guide the conversation in a way that it points all parties to possible solutions. Here are some scenarios and quick solutions that could help you:

Personal conflict

It happens: two people have a professional disagreement and it escalates. Maybe you’re one of those people. If you are, address the issue head on. Approach the person and talk to them about a way to fix it together.

If you’re managing people who are in conflict, it might be best to have them sort it out on their own. The best thing to do is ask them to speak to one another before involving you. Facilitating a solution can be far more successful than prescribing one.

Group conflict

If an issue is impacting a larger group, you’ll have to conduct a meeting. After everyone has had a chance to speak, transition the meeting to solutions. You might not hear solutions, so it could be up to you to identify them for the group.

Of course, there will be times when no one likes any of the solutions raised. That’s fun! If it does happen, ask for alternatives and discuss why the solutions proposed will not work. If you run out of time, start a collaborative document and follow-up within 24 hours to see what you have come up with.

There’s a definite chance that you’ll end up frustrated in group situations, because it’s hard to gain consensus. At some point, you will need to be the authority figure and decide on an outcome. This can be unnerving, because the decision sits only with you and you become acutely aware of how the success or failure of the solution will be seen as yours and yours alone. If you’re working with a team, you don’t want to operate that way.

Do your best to share the burden on the decision and involve individuals in the execution of the plan. This will spread that feeling of accountability.


Whether your issue is big or small, with one people or several, you need to follow-up on your solution to ensure that it’s actually working. This can be done with one-on-one meetings to help you understand and monitor progress and feelings.Make sure your plans are clear and that your communications about them support it 100%.

This can also be done with in person meetings, or even simple team status updates via email or in a shared communication tool.Do whatever feels right for your team and do everything you can to pay attention to the details and rebuild (or help to rebuild) trust and relationships.

Say Hello to Agreement and Goodbye to Disagreement

When you’ve made it through the prep, the meeting, and end up with a workable solution, you’ll feel gratified in knowing that you played a key role in fixing the issue. But there is one thing to be said: conducting a difficult conversation never gets totally easy.

We all know that disagreements pop up now and again, so you’ll be tasked with sorting out a new issue at some point. Using the tactics presented in this article, you’ll be able to assess a situation, put your emotions aside, and plan for a positive outcome.

This article originally appeared on the Intense Schools website.

December 1, 2015 - No Comments!

The Anatomy of a Difficult Conversation

We’ve all been there: Someone did or said something you or someone on your team does not agree with, and you’re the person who has to handle it. You actually don’t even want to handle it. Others know you don’t want to handle it. But it’s part of your job description to keep peace on your team—so you do what you can to make this conversation less awkward, edgy, tense, or even humiliating. But before you jump in, you’d better prepare, because these situations are never easy.

So how do you assess a conversation to be sure you can handle it properly, especially when every individual perceives these exchanges differently? There is a lot that goes into any conversation—difficult or otherwise—but keep in mind that if you initiate the conversation, you’ll want to think through every possible argument, statement, or outcome before you even speak a word about it. Your assessment won’t always be correct, but dissecting the factors that will play into your conversation will help you to understand the situation and the other person (or people) better—and conduct it like a PM professional.

The Situation – Think It Through Before You Act

Every difficult conversation stems from an encounter, situation, or scenario. So think through it: What actually happened and why? Chances are, you will hear multiple stores about a situation, but you will never know what truly happened without fully hearing all parties involved. Hearing a couple of accounts of the story might help you to gain perspective, but it can also confuse or upset you. This means that in many cases, you might have to stay neutral in order to get to an outcome that will work for everyone involved. The best way to stay neutral—because you must—is to listen and not provide any opinions or additional accounts of the story. Gather information, formulate your own opinions privately, and do what you can to simply understand what has happened.

If you are a part of the situation, but you want to resolve it with a conversation, it might mean that you have to remove your personal or emotional attachment to the issue and try to resolve it peacefully. This will certainly be difficult and it will test your professionalism and workplace decorum, but you can do it. No matter what you do, keep in mind that we all have our own points of view and we want to be heard. Give time and space for everyone to share their feelings about the situation, and the conversation will be less difficult.
If it’s helpful, jot down the issues you’re seeing within the situation and break them down. For example, if the issue is that someone has missed a deadline, you might write these points down and use them as talking points later on:

The Issue: You missed a deadline by three days
The Impacts: Someone else on the team had to scramble to get their work done more quickly to make the final deadline. That person stayed late and came in early to get the work done. Upper management noticed it and is now questioning me [the project manager] about your reliability and accountability.
How I Feel: Disappointed, worried. I also feel bad for the person who made up for your issue. You should thank them.
Resolutions: You apologize to the person who made up time. We set up an internal schedule to review your work at least one day ahead of your deadlines.

Sometimes taking 5-10 minutes to think through your emotions and writing them down can help you to organize your thoughts—and possibly even find a resolution. Your personal example may be far more complicated than the above, but if you think through the issue, impacts, feelings, and resolutions, you will prepare yourself for a productive outcome.

The Other Person

There’s always a culprit, and you’ll have to handle that person, or people, with great care. Knowing the ins and outs of the situation before you approach this person about it is important, because you’ll want some sense of how this person will approach the actual conversation. We all handle these conversations differently, so you really won’t know how they react.

Before going into any conversation, think about your history with the person and try to understand, or even anticipate, how they may react to the conversation. Of course, you will offer them the opportunity to explain their point of view of the situation, but thinking through how it may go will help you to prepare for the conversation.

Also keep in mind that no one likes to be on the receiving end of a difficult conversation. You’ll have to think about how to lighten the blow and to truly understand the situation to make it feel less difficult. For instance: Why did he or she do it? What’s motivating her or him? And, Are you worried about your relationship? Will this conversation affect the way you interact from here on out? It could if you don’t handle the situation with care.
The bottom line is that you must approach this conversation with a level of empathy if you want to truly resolve it and uphold the relationship.

You (and Your Emotional State)

So, you’re probably scared. Or nervous. It’s totally normal. No one likes to call someone out. In fact, you might even be frustrated or annoyed that you even have to address the situation. Wouldn’t it just be easier to let it slide?

Absolutely not. Letting one difficult conversation slide will not only set a precedent for accepting poor behavior, it will prove you to be a coward. It’s not going to be easy to sit in front of someone and call them out for wrongdoing—but maybe you won’t handle it that way. You’ll address the issue head on and share your own concerns or feelings about it (without making it about you, of course).

So what is stopping you? Fear of hurting someone else, fear of destroying a relationship, fear of perpetuating a misunderstanding? That’s a whole lot of fear, and it’s completely normal to feel that way. You’re a human being, and if you care at all about others or how they perceive you, you will be scared to address an issue head on. But you have to set that fear aside by preparing yourself for the conversation, stepping up, and facing your fear (and the other person…and the issue).

The Outcomes

Before stepping into the conversation, you should think about what you’re hoping to get out of the conversation. Are you looking for an apology? A physical action to resolve the issue? Another meeting? Understanding exactly what you want from the situation will definitely help you to formulate an approach for the conversation—and hopefully ease your fear.

Also remember to think about how you will follow up on the outcomes. There is nothing worse than talking through an issue, coming to a mutual agreement, and dropping it. Very often, an issue won’t be fully resolved with just one conversation. If you truly own the issue—and its healthy resolution—you will commit yourself to following up on it regardless of how uncomfortable that may be. So, think through your ultimate outcome and a useful plan for how it can be rolled out. Maybe it will truly be one conversation. Maybe it will be a series of check-ins to discuss progress and feelings. Whatever you do, make it comfortable for everyone involved.

The Conversation

After you’ve taken some time to think about the situation, you’ll be ready to approach the conversation. Put your fears aside and don’t worry about being wrong. Remember, keep the other person’s feeling in mind, and handle it in a way that feels positive and productive.

The best way to conduct a difficult conversation is in an open, honest way. You’ll want to create a meeting atmosphere that promotes positive energy. Do whatever you can to avoid holding the meeting in your office or in a conference room. Go out for lunch or coffee—stay in a setting that feels neutral, and less daunting. The pressures of work can seep into situations like this and you want everyone’s full attention, so go offsite and speak freely.

Don’t Sweat It

Remember that you are at the heart of the anatomy of your difficult conversation. You can control the tone of the conversation if you approach the situation with the level of care it deserves. You’ll obviously never be able to control what the other person contributes to the conversation, but you can be calm, understanding, and resolute through a little bit of preparation.

Are you feeling prepared to conduct a difficult conversation? The next article in this series will touch on ways to handle the actual conversation with a level of comfort you never knew you could bring to the table.


This article originally appeared on the Intense School website.

September 24, 2015 - 2 comments

It’s Time to Start Slacking

I’ve said it tons of times: we LOVE to talk about tools, but rarely do the tools universally work for teams. Well, folks, I think I may have to eat my words. As a consultant, I get to peek in on other people’s toolset, and I’m finding more and more that people are adopting Slack, a multi-channel team communication tool.

For years, teams have relied on tools like email, Skype, instant messenger, Basecamp, and many others to communicate project updates, changes, and general information. We’re used to an onslaught of messages coming from several directions, but often feel burdened and disorganized due to the volume, type, and urgency of the messages. We create rules about how to use the tools in order to assemble some sort of consistency, but those rules are difficult to remember (or are flat-out ignored). In return, information is lost and people become frustrated…and projects go off course leaving project managers wondering how to centralize communications. Maybe Slack doesn’t fully solve that issue, but it sure is getting close.

Slack has resolved many of these communication issues for organizations and teams alike. The tool allows project communications, collaboration, and camaraderie to happen all in one place, and it’s a beautiful thing. It’s not just any old instant messenger program, it’s a robust tool that facilitates better communication practices. And I have to say, I’m on board.Here are just a few reasons why I’m on board. (In case you are wondering...NO, I am not being paid to write this. I would never do that here. This is my honest assessment.)

“Channels” promote transparency

Slack provides simple one-to-one conversation functionality, but you can also segment conversations, topics, or projects by creating “Channels” within the tool. You can assign your users to as many (or as few) channels as you need in order to keep topics visible to the team members you want to see any individual topic. This ensures a level of transparency and collaboration that is often lost with email chains or one-off conversations. This may sound overhwhelming to some, but with notification settings and opt-in functionality, each user can find the right level of communication to be a part of—or ignore to be more efficient.

Slack integrations

There’s no getting around it: every team uses a number of tools on each project. This means a number of notifications from various applications. What’s nice about Slack is that it integrates with other tools like Dropbox, Google Drive, GitHub, and more, so things happening outside of Slack are pulled in via notifications. They’re not automatic, you have to set them up and you can control the noise. So while some teams may want to know each time code is committed to a GitHub repository, others want to check it manually. There are ways to set up or hack the notification to make them work for you and your team. 

Simple search

Slack is great for quick conversations or file sharing to make a quick decision about work. Therein lies a small problem: decisions are made, and lost in a long chat history. So, as a team, you’ll want to set up your own practices for using to the tool to make sure important conversations are documented somewhere you can find them. But, it’s nice to know you can go back through history to find information discussed in Slack.

File sharing

Every once in a while, someone will be working on a document and they need some immediate feedback. Slack makes file sharing easy, so it’s easy to have that conversation without using email or jumping on Skype. Drag and drop a file in to Slack, and let the collaboration begin. It’s amazing to see how quickly a question can be answered, or a document changed based on sharing a work in progress—It’s changing the way many people work.

At the same time, Slack allows developers to share code snippets. This means they can share and discuss code while the non-tech folks can follow along and learn…or ignore if they’re just too busy. If you’ve got a team of developers working on a project, you’ll want to ensure consistency. Sharing snippets can help with consistency and can eliminate hours of code review meetings by simply staying in touch about questions, practices, and ideas.

Take Slack with you

Running for a coffee and need to check in with someone? No problem—you can take Slack with you on your mobile device. It’s not only convenient, it’s easy to use and the functionality is mirrored in both experiences. The design of the app is slick, easy to use, and customizable. (The down side? You might never catch a break.)

Team Building

There aren’t many apps that actually encourage team building. With the integration of Giphy and custom emoji, communications have a personality that your team can build together. Some teams create channels for lunch plans, topical news, jokes, and more. Others interject animated gifs and emoji in conversations to break silence, or to help make a point. The “fun” is what you make it in Slack, and there is a lot to be had—and there should be when you’re communicating with your team.

Multiple accounts

Slack makes it easy to be a part of several accounts. So, if you’re a freelancer working for several companies, you can seamlessly switch between accounts within the app and keep up to date on communications across teams and projects. 

Plus, many small groups and communities have started Slack accounts of their own. It’s an easy way to share ideas, chat with long-distance colleagues or friends, and be a part of conversations that matter to you. Think of old-school AOL chat rooms, but more personalized and invite-only. It's pretty awesome. I'm personally using Slack in this way to keep in touch with industry friends and peers, and it sure beats email!

Make the tool work for you

Implementing team communication tools can be difficult, because you need full buy-in. The scary truth is that tools like Slack won’t work unless everyone agrees to use them. So if you decide to adopt Slack—or any other communication tool—remember that your decision isn’t just about the tool itself, its about how you’ll use it and how it will help you as a team. Slack can help you streamline your communications and optimize your workflows, whether your team is remote or under the same roof. If you’re feeling like it could be a good fit, try it for free on a project to see if it’s something your team would enjoy using.

*Thanks to benjamin on dribbble for the Slack plaid pattern