As lawyers, many of us tend to avoid difficult conversations. Although by nature, we are professional communicators — arguing a case in court, negotiating a business deal, and advising clients are examples of our expanded capacity for critical communication skills. Outside of offering incredible legal services, however, legal professionals tend to avoid having difficult interpersonal conversations with colleagues and clients.

We can negotiate a billion-dollar deal or make a clear case in court, yet have trouble walking down the hall to have a difficult conversation with a colleague about splitting credit or originations on a matter. How many lawyers do you know who have trouble giving or receiving real constructive feedback? Giving a client the hard news they may not want to hear? Fearing conversations about compensation or promotion? Or addressing or approaching issues related to paying the bills? This avoidance can harm workplace productivity and relationships, but also can have a huge im-pact on our well-being and stress.

Avoiding difficult conversations and the communications gap it creates is pervasive. An article from Harvard Business Review cites that over 60% of managers are “uncomfortable communicating with their employees.” (See here)

Out of this number, giving criticism and demonstrating vulnerability were top reasons they were uncomfortable.

Sometimes people will attempt to switch out on a matter, case or project; choose to work with someone else; or even leave a job to avoid the difficult conversations. The problem is this is only a temporary fix. These difficult conversations are like the monster at the end of a video game. If you don’t tackle it now, rather, try to avoid the situation, that monster will inevitably show up in the form of another colleague, partner or client in another career scenario down the road. You can only avoid it for so long.

So, the key is learning to hit the issue head on, rather than taking an avoidance tactic. Despite all the apprehension and anxiety, being able — and willing — to have challenging conversations are crucial for growth and success. The more of these you have now, the more equipped you will feel in the future.

This article addresses why difficult conversations are especially challenging in the legal environment, the value of having them, and offers a framework with a few extremely valuable tools for navigating these sticky situations to engage in these dialogues more directly and effectively. I call it a D.I.A.L. framework, which can help us “dial into the dialogue.” The following focuses on the four “D’s” in the process — Discern, Direct, Do it Soon, and Disarm. The goal isn’t to eliminate the difficulty of the conversation entirely. What’s the fun of that? The key is to reduce the energy drain. If you can somehow reduce the drain of having the conversation in the first place, it can have a huge impact on moving you towards desired outcomes.

Difficult conversations as a lawyer are uniquely challenging for several reasons. The hierarchical structures in law firms and corporate legal departments often create power dynamics that make open dialogue difficult. Junior associates may hesitate to speak candidly to partners, and in-house counsel may find it challenging to ad-dress issues with senior executives. If leadership doesn’t encourage speaking about challenges openly, additional pressure abounds in an already high-stakes environment. The stakes? Jeopardized cases, harmed client relationships, ethical violations, just to name a few. Because difficult conversations are already hard and made even harder by external pressures, it’s important that we handle both ourselves and these conversations with care.

The Potential in Difficult Conversations

Although challenging, difficult conversations have exponentially positive outcomes when handled right. Here are three main reasons you should have that hard conversation you’ve been putting off:

1. Strengthens professional relationships

Open dialogue fosters trust, which is the cornerstone of any strong professional relationship. Navigating through challenging situations with others can increase bonding, so long as mutual respect and positive regard is maintained. Initiating hard conversations can lead to increased admiration amongst peers and leadership, which can lead to them entrusting you with bigger projects and opportunities.

2. Creates a culture of openness and inclusivity  

The simple decision to engage instead of brushing over topics that may be uncomfortable (such as unconscious bias, equity in the workplace, etc) generally leads to more inclusive and equitable environments. For instance, one candid discussion within the firm about unconscious bias can lead to more equitable hiring practices from leadership. Of course, it’s best to use discernment when broaching sensitive or protect-ed topics at work, but in applicable cases, breaking down barriers is usually a win-win situation. When people feel heard and understood, they are more likely to contribute their best work.

3. Enhances performance and client satisfaction

For both clients and leadership, sharing unpleasant updates is almost always better than withholding information, as long as it’s done thoughtfully. Transparent communication ensures that everyone is on the same page and can move forward, fully equipped with the information needed to make better decisions. Candid discussions also pave the way for constructive feedback and assistance. With introspection, they also allow for personal growth, to reflect and confront where things may have gone wrong and create space for improvement.

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Discern Whether You Want To Have the Convo

First, take a moment to discern whether you want to have the conversation. It’s an empowering moment that you don’t want to miss. Let’s not forget that you have a choice here.

• Will having the conversation move you clos-er towards your goal?
• Will the person be receptive?
• Is there a power dynamic here that is too wide to overcome?
• Would having the conversation open me up to some form of harm?
• Will they get too defensive or not engage in the dialogue in a way that won’t make any difference?
• Will you regret not saying something? Does not having the conversation implicitly accept some behavior you want to address?

You have a choice here and want to make an informed decision. Take a moment to evaluate whether you want to make an investment in the first place. If you make the choice to not have the conversation, you can evaluate again in a few weeks or months whether having the dialogue is the only path and revise your decision at a later time. For now, let’s assume you plan to have this conversation. Here are some tools for your approach.

Have a Direct Dialogue

Have a direct dialogue and avoid “triangulation.” Triangulation is the tendency to seek false refuge by complaining to a “buddy” (e.g., a colleague, spouse or friend). Once we complain to our buddy, invariably they can tell us that we’re right and that the other person is wrong. This buddy process isn’t a strategy to address the i-sue, it’s a way of seeking affirmation and making us feel better amidst the tension. Once our buddy gives us the dopamine hit of “buddy acceptance,” we feel a little better and potentially lose energy to have the real conversation we need to have. Although venting is amazing, and it’s healthy to let the frustration out on someone else before we directly address an issue, be wary of the cycle of seeking false refuge, venting, and avoiding – rather than addressing. Keep in mind the risk of not directly addressing the issue and the benefit of having that difficult dialogue. What is the upswing potential? Also, remember that when you raise a difficult issue with someone else, what you are really telling them is that “I have faith that this situation can improve. I have faith that we can all do better. I have faith that change can happen.” When we avoid the conversation, we have no faith in them and, maybe even, in ourselves.

Do it Soon

Be sure to address the conversation sooner rather than later. The further we get from a situation, the harder it is for you and for them. People forget what happened, the energy moves on to another issue, and you aren’t setting anyone up for success by unnecessarily delaying. Certainly, we should count to 10, or wait 24 hours, or wait until next week when the schedule clears up. But that’s all the leeway you need. I was coaching a client who was avoiding giving feedback to a senior partner/manager of theirs. We came up with the game plan, and they said they would “raise it in their next review.” “Next review?!? Your review is in November, and it’s March!” I was not having it. No need to wait for review season, have that conversation now or sooner rather than later. And if you’re already in the delay cycle, remember that it’s never too late. You can still raise that conversation you avoided a year ago, so let’s move towards the difficulty rather than away from it.

Consider a Disarming Or Diffusing Statement

It’s certainly not a requirement but starting a difficult conversation with the intention of diffusing or disarming the other person can be a helpful approach. When someone feels attacked or defensive, it’s natural for them to put up emotional barriers, which can hinder productive communication. When people feel threatened or attacked, they are less likely to share their true thoughts and feelings.

A disarming statement can show understanding, empathy and vulnerability toward the other person, and often prompts them to reciprocate. By using disarming or diffusing techniques, you can lower the other person’s guard and make them more receptive to your message.

A few options of disarming statements that I like are listed below.

• A Direct Approach. “I want to talk to you about something difficult” or “I want to have a difficult conversation.”

• Make it Collaborative. “I wanted to get your insight on handling something that’s challenging” or “I need your advice on something that’s really difficult for me.”
• Practice Vulnerability. “I’m not sure how to say this, in fact it makes me uncomfortable to even bring it up;” I’m going to say something that might feel tense or awkward;” or “This is difficult for me to raise.”

You can try these options or craft your own. Think about the disarming statement that would work for you and write something down. Give yourself an opportunity to knock on the door and allow them to look through the door hole to get a sense of what’s ahead. The disarming statement manages their expectations and prepares their mindset. It also supports you by easing the path to being more assertive later in the conversation.

Keep in mind that in a disarming statement, there’s no need to be dismissive of yourself or self-deprecating. Avoid statements like:

• “I’m going to mess this up.”
• “I’m going to get this wrong.”
• “I’m not sure this is a good idea.” Ultimately, find a disarming statement, not a discrediting one.

Starting a difficult conversation with the goal of diffusing or disarming the other person is helpful because it creates a more conducive environment for productive and respectful communication. It can lead to better understanding, problem-solving, and ultimately, resolution of the issues at hand.

Conclusion

In the legal profession, even the most adept communicators often find themselves avoiding crucial conversations, and it’s healthy for readers to investigate when and why they do this. This reluctance impacts business relationships, workplace dynamics and overall well-being. Even though the legal landscape demands skillful communication, these uncomfortable conversations are frequently sidelined.

Difficult conversations pose unique challenges, yet the lessons and resolutions lie within the act of stepping towards the difficulty, rather than avoiding it. We can hide behind the challenging legal work, but it’s ultimately your ability to choose the challenging dialogue instead that will open more meaningful doors in these challenging situations. To navigate these conversations effectively, spend a little time preparing and developing a strategic approach. The more conversations you have, the more you will clear. It’s a path for reducing energy drain, investing in your professional growth, and a significant driver towards career success.

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