How to Have a Difficult Conversation

How to Have a Difficult Conversation

Having a difficult conversation with someone is hard to do and extremely hard to do productively.

difficult conversation

What is a difficult conversation?

It’s the conversation you need to have when the topic is uncomfortable: asking for a raise, discussing a mistake, saying “no” to someone who wants you to say “yes,” disagreeing with someone. Tough conversations come in many varieties.

Why are they so difficult?

We all have fears and vulnerabilities. Feelings get evoked that affect self-esteem, or touch off anger, or touch off a sense of being mistreated or disrespected. Blame rears its ugly head. There could be negative consequences at work if the conversation does not go well. People fear a loss of status, even job loss. Given the potential negative consequences, many people try to avoid difficult conversations altogether. But often that means important problems in the workplace do not get resolved, and the same mistakes are made again and again because they were not adequately addressed. It would be far better if people could use a few helpful rules that make tough conversations productive instead of destructive.

First: Understand the components of a difficult conversation

Most difficult conversations include these components:

  1. There was a misunderstanding or problem in communication.
  2. There is blame or assignment of fault.
  3. There is emotional tension.
  4. There is an impact on each person’s identity or self-view.

Second: Understand how meaning is conveyed in a conversation

About 55% of communication is body language and 38% is vocal. Gestures, facial expressions, body language, posture, tone of voice, volume, and pitch are all a large part of the messaging. The words we speak convey only 7% of the meaning. We need to be aware of the way we convey information.

Third: Understand the “Three Stories” approach

Every difficult conversation has three stories or vantage points that can be thought of as perspectives: my view, your view, and the description as if viewed by a neutral third party. The first two perspectives are biased because they represent one person’s self-serving story. Most of us tilt reality in our favor. We tend to forgive ourselves or ascribe blame to someone else. But when it comes to having a difficult conversation, if you start out with your biased viewpoint, the conversation will not go well. Start the conversation using the perspective of a neutral third party, as if you are a reporter describing what is evident.

Here’s an illustration:

You failed to send an important document on time to the client for his signature, the client missed a crucial deadline and had to pay a penalty fee as a result. The angry client calls your boss to complain. Your boss calls you into her office and reams you out. However, you discover that the reason the document was not sent on time was that the new document system you relied on was set up improperly. Your colleague was the one who set it up. Other documents are going to be late as well because the system is flawed. You are very upset. You need to have a difficult conversation.

Start from the perspective of a neutral third party.

“Our new filing system has a glitch and because of that our client did not get a document on time and had to pay a penalty. We need to fix this so it doesn’t happen again. Help me understand what we need to do.”


“I am really upset about the way you programmed the new document system. Because of your incompetence I got blamed and the client paid a penalty fee. What do you have to say for yourself?”

With a difficult conversation, emotional content bubbles up that is not expressed outwardly. This unspoken internal dialogue impacts the conversation but no one talks about it. Embarrassment, shame, righteous indignation and other intense feelings get activated. We engage in the psychology of self-defense: sarcasm, anger, and blame. Remember the Saturday Night Live skit where the irate pundit trades insults with the female talking head? “Jane, you ignorant slut!” Once our internal emotions are stirred up and slosh over into our conversation, it’s no longer productive.

Fourth: Follow these guidelines for having a difficult conversation

It may not be possible to have a productive difficult conversation with everyone. Some people are not mature enough. Shaky self-esteem, narcissism, and other emotional problems can make it hard to have a tough conversation with some people. But if you have a reasonably mature colleague, here are five guidelines to use.

1. Be Curious
A simple shift in mind-set can change the tone of the conversation. Say: “Help me understand,” “I’d like to know,” “I’d like to learn.” All of these openers give permission to the other person to explain and learning can take place.

2. Abandon Blame
Do not argue about who is right. Blame sabotages the conversation by getting people into self-defense mode. Focus on contribution. What can you own up to that contributed, even if it was a small part of the problem? Take ownership of any part you played, so that others will “fess up” too. The result is greater transparency which will help improve the process.

3. Do Not Assume You Know the Other Person’s Motives
Be skeptical about your own good intentions and actions. Give the other guy the benefit of the doubt. Do not start with pre-conceived ideas.

4. Be Empathic
Monitor your own feelings (e.g., “I feel embarrassed about missing something others think is obvious. I am failing at my job.”), or anger (e.g., “I am not appreciated!”), or other emotions. Understand the probable feelings in the other person, including shame, guilt, anger, and more.

5. Acknowledge Other’s Feelings
If people have their feelings acknowledged it helps diffuse their anger. “You must be upset. I am sorry you have to deal with this after all you did to make the system work.”

These five guidelines arm you with the right attitudes to have a good talk about tough things. If both people have these attitudes, the conversation will go well. Even if you are the only one with this mind-set, the conversation should go well if the other person is reasonably mature.

Even if you are tempted, never have a difficult conversation by e-mail or on the run. It will not create a lasting positive result.

Have difficult conversations in a productive way to build a better workplace.

Marketing for Lawyers, Part III: The Marketing Plan (Promises You Make to Yourself)

This is the third of three blog posts on marketing strategies for lawyers; the first was Marketing for Lawyers, Part I: Setting the Stage and the second was Marketing for Lawyers, Part II: De-Mystifying Business Development Activities.

A marketing plan is really nothing more than promises you make to yourself. You are going to give yourself some assignments and deadlines, and it will be your job to follow through.

Marketing Plan

Why Bother to do a Marketing Plan?

The marketing plan is a roadmap. If you were about to set out on a journey, you would want to have a roadmap or GPS to guide you. Without it, you run the risk of wandering around aimlessly in the woods on your quest for business. The time you spend lost in the woods is time you are wasting. Since you are a really busy person and you do not want to spend an inordinate amount of your precious time on marketing, the roadmap is a time saver.

The marketing plan does even more for you:

  1. It helps you to eliminate excuses.
  2. It helps you to focus by setting up tasks that you can do based on the time you have available to devote to the task.
  3. It helps your firm to feel confident about the seriousness of your purpose.
  4. It’s empowering for you. You know just what needs to be done, which eliminates the sense of ambiguity or amorphousness that can otherwise deter motivation.
  5. It can keep you from being sidetracked by other requests for assistance or demands on your time because you will analyze the requests based on whether they further your goals.

When you map out a marketing plan, you should consider some or all of the following:

  1. Your abilities, interests, and strengths as a lawyer and as a person.
  2. What you will need to do in the four key realms of networking, leadership, meetings, and client contact.
  3. Whether you will need to obtain specific assistance from your firm, and if so, what.
  4. How you can engage your secretary or other staff to achieve your goals.
  5. Whether to meet with key people by yourself or with others from your firm.

A Sample Marketing Plan

Here is a sample marketing plan that was developed after in-depth discussions about business development goals; you can use it as a model. Click on the image to download the PDF.

marketing planIn developing the plan, we considered organizations, community activities, writing, publishing, speaking, key people at work, people known from past experiences, hobbies and more to identify potential areas for growth relationships that could lead to business. We talked about the mindset that works best when going to events or to one-on-one meetings. We addressed how to message effectively, and the need to persevere despite the difficulty of seeing immediate progress and much more.

Instead of thinking of this as a marketing plan, think of it as “promises you are making to yourself.” Use the goal / action / deadline / status as a progress report, and think about any impediments to implementation, including emotional impediments such as nervousness about seeming to be needy, or anxiety about going to a group meeting. Removing emotional impediments is by far the most important component of a successful campaign to market services. This is something that is often not considered when people talk about marketing. What I have learned is that many marketing plans are pretty easy to put together and they look lovely and have great promise, but the biggest problem to getting the work done is emotional discomfort about implementation. Working through personal issues is essential. If you do not do that, even the best marketing plan will sit on your desk and never evolve into business.

What can you do to prepare?

Review Personal Issues

Identify how you best relate to people:

  • Do you love parties?
  • Do you prefer one-on-one meetings?
  • Do you enjoy speaking to large groups?
  • How about small groups?
  • Do you teach in any capacity?
  • What social skills do you want to build?
  • Have you written for any journals or trade magazines?
  • What constraints do you anticipate in setting up your marketing plan?

Future Business

Describe your ideas about where your cases could come from in the future.

If you can spend some time at least thinking through these questions, it will help to clarify your actions.


The path to greater business generation is almost like a quest on which you embark. Think of it as a medieval quest. In the beginning, it is not always perfectly clear which path to take, but if you know the castle or castles you are determined to reach, the path will get clearer as you go along. Your job is to get out there and find your way into and through the woods. You have to help people to trust you and like you. As your quest evolves, your job becomes more specific and clear and you will have sell meetings with potential clients, but they will be more like counseling or coaching because you already have the client’s trust.

In its most elemental form, marketing is a way to create trust relationships in the castle or castles where you derive business or want to derive business.

And one more key thing: what really works best is changing from thinking there is something you need to do, to thinking of the activity as enjoyable and fun. Finding the fun in interpersonal interaction is very important for long term motivation. How can this happen? By thinking about what you actually get a kick out of when you meet new people, instead of focusing on the dread. When I work with clients who are anxious about marketing and relationship building, we talk about how deeply rewarding it feels to develop a new friendship and tap into that instead of focusing on some imperative like “you have to do this or that to be successful” or “these are tasks you have to complete by such and such time.” When the focus is on enjoyment and personal reward, people are much more able to follow through.