Avoiding Tough Conversations? Welcome to Being a Lawyer (6 min read)

A friend who is managing partner in BigLaw mentioned to me that although the firm has a 360-degree review program, that the program never gets implemented. Why? Because lawyers don’t want to receive real feedback or stir up controversy on a small team or group. Rather than dig in, address the issue, and possibly improve the work environment, the firm would rather avoid these conversations altogether. When working with my coaching clients, I’ve seen more of the same:

  • A firm partner facing insubordination by an associate who planned to demand behavior change “because I’m the partner,” rather than talk through a more sustainable outcome.
  • An in-house attorney wanting a promotion that avoided raising the subject and planned to continue simply “working hard” until a promotion was offered.
  • Another partner avoiding reaching out to potential clients because “they’ll think I’m begging for business.”

Although lawyers are incredible at arguing on behalf of their clients, many don’t welcome having tough personal conversations. Rather than avoid, why isn’t our instinct to lean in? Since when was avoidance ever a strategy we advised our clients? Naturally, these people are worried about all of the negative consequences of their interactions. But, what if the conversations went swimmingly, or at least better than expected? More importantly, what’s the cost of inaction? Ongoing tension and stress. Never pursuing the dream of having your own book of business. That feeling of being ‘stuck’ that only compounds over time.

When you shift your approach and instead make a habit of stepping into these difficult conversations, it can be a game changer. Clients are reporting that they don’t have to spend hours or weeks either avoiding conversations or managing the inherent underlying fear about them, and instead having a greater excitement around the possibility of a successful resolution.

Part of the problem — lawyers don’t take well to criticism, rejection, or setbacks. They typically get defensive, and often feel a need to explain and justify their behavior to others. They can be easily wounded by a critical comment or by a client’s failure to return a call. Difficult conversations are an unavoidable and recurring instance in the workplace and in business, and they don’t have to be feared or dreaded. If you take a moment to pause, and think it through, they can be handled with insight, knowledge, and the proper skills to benefit yourself and those around you.

Another problem — our legal advocacy training doesn’t always apply to one-on-one conversations. Attorneys are great at doing what it takes when representing clients. Unfortunately, winning in court or in disputes is great in a competitive framework, but this isn’t always appropriate for handling personal conflict. For example, in advocacy you may have been advised to:

  1. The goal is to win.
  2. Use your “knowledge” to build trust with the judge.
  3. Constantly think about what points to rebut and defend/persuade on each position.
  4. Brainstorm backup arguments.
  5. Be perfect in this process.

Difficult conversations don’t always need advocacy. For example, you don’t have to be “right” when handling workplace conversation, it may not even be your goal. Also, you can take the pressure off on being perfectly polished — you’re not performing in front of judge or jury, and there’s no time for parties to review advance briefings. In fact, with difficult conversations, you have to get OK with a certain level of messiness.

Legal training isn’t prepping us for personal conflict. When working with attorneys on handling difficult conversations, we could use coaching to help switch the frame. This includes:

  • Understanding the nature of difficult conversations and how to handle them.
  • Identifying stages and preferred strategies for handling difficult conversations.
  • Using enhanced listening and empathy in a way that minimizes tension and conflict and strengthens relationships.

This is where the real work is. If you have a difficult conversation that you’ve been avoiding, consider the following:

Pay Attention to How Avoidance Feels — Yes, I said feelings. Are you paying attention to how you feel when you are avoiding that conversation? What’s actually happening? Is there anguish? Are you concerned? Try to understand the consequences you’re worrying about. For example, is it being disrespected or rejected? Take a moment to understand the underlying stress. Perhaps it’s some form of fight (e.g., I need to win this!) or flight (e.g., what can I do to avoid?). Pay attention to where these feelings show up in your body — possibly a mild tightness in the chest, or maybe pangs in your stomach. Do this same investigation or inquiry of yourself, during, and after the difficult conversation — continue to pay attention to how it makes you feel. Don’t discount your own experience.

Assume Positive Intent or Mindset. It’s not always “we’re the good guys,” and “they’re the bad guys.” When having a tough conversation, instead try assuming that the person you’re planning to speak with actually means well; that they ultimately want to support you, and believe you’re doing your best. For example, if someone sends a rude email while cc’ing teammates, we may assume that they want to embarrass us. We could instead assume that they were in a hurry, stressed, and didn’t realize the negative tone. If we’re meeting with a potential client, we may assume they think we’re “begging for business.” Instead, imagine they need additional support from outside counsel because they’re underwater with deadlines. Not much comes from assuming the worst, so stay away from assumptions and give the alternative a shot.

Listen First. Rather than trying to score a win, or beat the other side, think long term about what actually listening in this conversation can do for the relationship you have with this person. For example, in a conflict, you might think listening first means conceding your argument time, letting them score points, or even acquiescing to their position. In a personal conversation, however, you don’t actually have to meticulously address every point. To start, imagine the best listener you know, and picture yourself as that person. Simply “hearing out” the other side can do a lot including reducing the tension, making the other person feel “heard,” and give you information on what might really be at issue.

Be Clear and Succinct With Your Needs. Know and express specifically what you want, focusing more on the other person’s actions, and less on their feelings. If you’re dealing with insubordination, stick with the specific behavior you observed, the impact of that behavior, and what needs to change, without judging intent. Avoid putting them on the defensive by blaming or using generalizations (“you always” or “you never”) or asking why they went down that path. If there’s push-back, go back to the deep listening mentioned above, without interrupting, disagreeing, or necessarily countering, and then briefly restate your needs.

Vision for Positive Outcomes. Rather than doubt yourself, and brainstorm what could go wrong, start to imagine all of the things that may go right by having the conversation. You might land the client. You might start to smooth out issues with your colleague. Imagine the potential benefits even if you don’t hit your ultimate goal. Focus on other potential long-term gains .For example, consider the importance of improving your connection with a colleague rather than making sure the colleague understands they did something wrong. With a client pitch, you might not get it this time, but maybe this is just the beginning of a long-term business relationship.

Shifting your approach and repeatedly stepping into these conversations, you’ll find yourself feeling more excited about the people, relationships, and scenarios that often caused you difficulty, and ultimately feeling much better about your work and life.


Rudhir is an executive coach for lawyers, focusing on workplace intensity, leadership, performance, and mindfulness. He was formerly a partner at Fish & Richardson PC and then senior counsel at Apple. Reach him at rudhir@krishtel.com, www.krishtel.com, or follow on Twitter @rudhirkrishtel.