How to Have Difficult Conversations at Work

Queasy. Unsettled. Lump in my throat. Heart in my stomach.

Just a few of the things we often feel when we’re about to engage a co-worker, or even worse…a superior, in a difficult conversation. If we’re honest, we often avoid these conversations—masterfully eluding the inevitable conflict we are sure will lead to disaster.

We are tense because we know we’ll have to be vulnerable. Being vulnerable at work could easily lead to harsh criticism or judgment. The emotional exposure can be too much to take.

What’s the root of all of that pressure? It’s actually quite simple—there’s entirely too much at risk. And let’s face it, in a work environment…we hate risk.

The results of this conversation could affect our career, our compensation, and the ability to work together with teammates in the future.

All of those factors can affect our family and those we care about—not to mention our sense of self-worth and confidence about the future. Profoundly negative consequences can result if the conversation doesn’t go well!

The good news is that there are tools to navigating how to have difficult conversations at work with your coworkers, your boss, and even high-level executives.

When we understand the many benefits of taking risks, combined with time-tested skills for actually having the dialogues, we will emerge more confident than ever to tackle those discussions.

What’s the first step? Take as much time as possible to prepare.

Conversations at work, because of the risk, really need to be prepared for. If at all possible, don’t do “on-the-fly” difficult conversations at work.

If you are ambushed by one that you didn’t see coming, learn to evaluate quickly whether or not the timing and environment are appropriate for the dialogue.

If not, kindly request that you pause the conversation until an appropriate time, place, and frame on the conversation can be agreed upon.

That’s not always possible—but it is worth the try. Don’t, however, fall into the trap of simply avoiding the conversation altogether. This will inevitably make it worse.

Whenever you feel tempted to put off the conversation again and again—make the decision to take the time to actually prepare for it.

Avoiding conflict is the quickest route to an even greater conflict blowing up, and at a time we least expect it.

Don’t avoid risk. Learn how to manage it.

Managing risk is huge. First, let’s understand a few critical components of the conversation that will help us navigate the minefields.

  • What is this conversation about?
  • What are my goals for this conversation?
  • What is the risk in this conversation?
  • What am I worried might happen and how do I avoid that derailment?

The level of risk is tied to who you are talking to and where they are in the organization chart at work.

If we are talking about a coworker, we will likely feel a low amount of risk. A discussion with our supervisor might bring with it a medium amount of risk.

Talking to a VP? High risk. Chance opportunity with the owner of the entire company? Crazy risk!

The higher the risk—the more we must prepare.

And that means getting as clear of a frame on the conversation as possible.

The frame on the conversation is very important.

  • What am I trying to get out of this conversation?
  • I’m not interested in winning the conversation, but I want to strengthen our working relationship so that we can work more effectively in the future.
  • I’m not trying to do this conversation to them, I’m wanting to have this conversation with them. That means truly listening, engaging, watching body language, and trying to be relaxed while maintaining posture and poise.

In the conversation itself, I need to understand not only what I’m wanting to get out of it, but what would the other party seek to get out of it.

Do they want increased clarity on our perspective of a situation, or purpose in why we’ve taken certain actions?

Any chance you have to ascertain what they are trying to get out of the dialogue will go a long way towards building the bridge necessary to carry the weight of the conversation and coming out in a stronger position on the other side.

Who is this person? What are their values? What’s important to them? What is their perspective and how exactly do I agree or disagree?

I’m not trying to be best friends or intimate with everyone I work with—but I want to work more effectively with as many as I can (for their sake as well as my own).

Why would this conversation be important to them? What’s their perceived benefit of working more effectively with you?

If the discussion isn’t important to them at all, we need to find out why before we have it. A disinterested other party will lead to a very short and ineffective difficult conversation, and that will likely produce an even more difficult one down the road.

Be sure to re-frame the conversation until it is clearly important to both parties involved.

If the difficult conversation is with a team-member in the cubicle next to you, you likely will have a similar perspective. However, as you go higher up the organization chart, the issues become more complex. You must be in a posture of learning as much as you can.

How do I engage my boss in a difficult conversation?

When approaching a superior, realize their lives are extremely complicated and as a result, have to be intensely managed. Things that come to them unexpectedly, even with good reason, are often seen upfront as a complication—a further complication in the already delicate, complicated world they live in and manage.

If we can use the tools of candor, tentativeness, and listening effectively—we can help them gather the puzzle pieces of data and perspective that will help make their management role easier.

If when we approach our superiors, we can consistently demonstrate that we have the best interest of the organization in mind—and can be effective to help make things less complicated—we are positioning ourselves for success.

If we come to them with no clear frame on the conversation, no stated goal, and no direction or orientation towards what we want to accomplish—we will further alienate that superior from looking to us in the future.

That being said, we can still build a stronger and stronger relationship with that boss—even if we don’t have the exact nuggets of managerial wisdom to help them run the business better.

Simply being good at navigating difficult conversations, keeping things on track, and communicating clearly, will show them how much of an asset you are on their team.

Executives have very clearly defined goals, outcomes, and organizational structures. They are dealing with high-level strategic decisions every day. Most of those decisions affect many different people’s lives under their direction.

Therefore, they are often looking for someone who they can trust to discuss what is in the best interest of the company.

Take a moment and put yourself in their shoes. Imagine that you are that executive, and that your VP, who is in charge of inventory, just came in to tell you they’ve successfully delivered all their product. Then, you get an angry phone call from the VP of sales with a huge problem because they have no inventory!

Right at the moment you get off the phone, YOU (the employee) walk in.

The last thing that executive wants is to listen to someone whining about a narrow personal issue that doesn’t have any bearing on organizational health whatsoever. Not an effective frame on the conversation!

A better frame would be taking that seemingly personal problem and zooming out to the potential of what might be affecting the whole organization.

“Here’s where I feel pain, and I’m wondering how others might be feeling and what I could do to help …”

“Here’s what doesn’t seem right to me, but I realize I don’t have the whole picture …”

Employees that ask good questions are employees that get to ask more and more good questions.

The person that is primarily concerned with their time, their job, their salary—yet rarely looks towards the greater interest of the company—is someone that will have difficulty engaging their superiors successfully.

Again, your superiors are looking for fewer complications in their world. They are doing this in order to help the entire organization.

They do not need more complications with the goal of only helping out one individual—and that is the message you present when you make it all about yourself.

Be very mindful of how much whining you do at work. It could be the subtle water cooler complaints or the too loud conversation on the phone in a jammed-packed office that your boss and coworkers pick up on.

If you become seen as the person who consistently brings a negative vibe into conversations, don’t be surprised when the necessary difficult conversations with coworkers become even more difficult, or tersely ended.

No one wants to be the subject of your next complaint—and people will go to the lengths of avoiding you if that’s what it takes.

You want to be the person in the organization that is seen as acknowledging clear issues, yet having the resolve to press through them towards positive change.

If you consistently engage in difficult conversations at every level of the organization with a great frame on the conversation, a clearly stated goal that will help the entire organization, and genuine listening skills and tentativeness—you will posture yourself for more and more success in the inevitably difficult dialogues that come at work.

In fact, you will likely be poised for increased upward mobility and the invitation to participate in higher level strategic discussions!

Every single one of the six steps in our model of becoming more effective at difficult conversations is crucial—and even more so as your dialogue includes members higher on the organization chart.

The last step is to go for Consensus, Agreement, and Accountability. That’s how you want to close every conversation with your boss.

Once you’ve discovered what it is that they are looking for (not just what you are getting out of it), make sure to restate that point with the precise action steps you are going to take to move that agenda forward.

Ask them if there is anything they need further clarity on, or if they have any further questions for you. Without being too awkward, remind them of your commitment to the organization and its mission. Share your passion for continuing to grow in your skills to help the business succeed.

Leaving the conversation on a positive note of dedication and action will show your superior that you aren’t a complication—you are a part of the solution to growing the business they are managing.

The genuine, direct, and clear communication—as well as the consistent positive attitude you display in front of your superiors—will show them that you are going to contagiously spread that winning environment wherever you go in the company.

And that’s turning a hard conversation into a win-win dialogue!


Want to become more effective at how to have difficult conversations at work?

Sometimes our conversations don’t play out that well, run off the rails, and people leave feeling demoralized or belittled.

We know what it’s like to walk away from a conversation that we are still carrying hours, days, or even years later, which is why we’ve created this FREE resource entitled 15 Ways to Turn Hard Conversations into Win-Win Dialogue. It will help you start to navigate even the most challenging discussions. Click here to download the guide now!

Related Posts

How to Have Difficult Conversations at Work

Send this to a friend