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Why Do Difficult Conversations Grow Your Law Firm? 8 Keys to Empowering Conversations

Updated: Jun 5

According to a 2023 Gallup report, Americans are unhappier at work than in years. What are the reasons for this? There might be plenty of them, including economic issues, job insecurity, lack of career growth opportunities, poor work-life balance, inadequate compensation, etc.

In many cases, the key reason lies deeper than we think: the lack of communication.

The power of courageous conversations

You’ve been forced to communicate since before you could speak. Unfortunately, knowing you’re supposed to communicate well with others is very different than actually doing it. At times in the workplace, we fear speaking the truth; it’s often easier to remain silent to avoid difficult conversations.


However, the number one strategy for building a great team in the legal sphere is becoming comfortable with the idea of communicating with colleagues and stakeholders so everyone can prosper, grow, and change.


When you set aside your ego and lift up others, your team will trust your decisions and actions. We can best reach excellence when we create a solid, supportive environment where everyone can thrive—not simply survive.


The 8 keys to an empowering conversation

Rather than blaming, shaming, or distrusting one another, we need to restore healthy communication by empowering one another. When we do, we’ll start to notice that others will stop coming with complaints and drama. Instead, they’ll come for honest feedback. Empowering conversations form the basis of any trusting, well-communicated relationship.


When someone feels the details of the process or the assigned task aren’t clear, empowering conversation gives that person the confidence to ask for clarity because they trust the other person. Everyone knows the desired result and has permission to not know the path to get there right away. Even if you veer off the path, you’ll get back on it easily, because both parties are more than willing to take action to get results.


There are 8 keys to an empowering conversation that will create a win/win for everyone involved.


Walk the walk

This happens before you talk the talk. The ultimate rule, and subsequently the most ignored, is to set an example by following your own advice. Do you come to meetings late? Are you unprepared?


Bottom line: No one will want to hear ideas and suggestions if you don’t have your own bases covered. That is, practice what you preach.


Be honest while respectful

This one can be a tricky line to toe. It can be accomplished by speaking about dangers and opportunities rather than personal attacks and judgment. Before you say something your gut tells you might sound offensive or make someone defensive, ask, “May I have your permission to be blunt?”


This prepares the other person for information they may not want to hear and sets the tone for honest conversation. It also shows respect by asking permission to give feedback rather than assuming you have the right to provide feedback and your perspective.


Present facts without emotion

Emotions are subjective. Getting into debates with others based on emotions can be daunting, and difficult, and spread miscommunication. When we use our emotions first, we bury the facts. We need to leave excuses at the door because these are some of the root causes of miscommunication. By focusing on the facts and not letting emotions take center stage, you’ll come to a place of resolution for all parties involved.


Notice the difference:


Emotion: “I am overwhelmed and stressed, and I’m already making so many mistakes.”


Fact: “Our average new clients have increased from five to eight per month. This is an additional fifteen hours per month of work for me. I find myself rushing to get all the documents done on time and have caught three errors I’ve made. I am concerned that this increased workload and the time pressure to get it done will cause me to make mistakes.”


In the “Facts” section, the person cites concrete numbers and tactical elements of what happens on a daily basis. Though I can appreciate those feelings of being swamped and stressed out, clouding facts with emotions won’t help solve the problem.


Don’t be a “yes-er”

I’ve seen clients lose credibility with others by either trying to have the right answer or just saying “yes” when the answer is actually “I don’t have the information/time/understanding/resources right now.”


Don’t be afraid to say, “Let me think about that” or “Let me find out I confidently and competently have the capacity and/or resources to X.” It’s so much better for everyone when you allow yourself time to think about a problem or research an answer instead of rushing to a habitual “yes” or offer a solution when you don’t have the time or information at hand.


Acknowledge the other person’s strengths

Make sure to begin your crucial conversations with positive and motivating candor. When you acknowledge a person’s strengths, they’re more likely to use them. According to decades of Gallup research, people who use their strengths every day are six times more likely to be engaged on the job.


Be selective about the time and place

By picking a good time and place to have a crucial conversation, both parties can hear and respond well. For instance, Monday morning, when your boss has a full day of back-to-back appointments until 7 p.m., may not be the best time to complain about your workload. Choose a time when the other person will be open to your conversation and not distracted by other things. I recommend looking at the other person’s schedule and asking for a time that would work well for both of you.


Don’t pop the balloon

When someone has an incredibly new and exciting idea, they want to tell everyone. However, when the workplace gets hectic it’s easy to burst the balloon. Successful businesses need innovative plans. It’s important to ensure that creativity doesn’t get zapped into a negative space.


Instead of saying, “We have work to do, stop focusing on this hunk-of-a-junk idea,” try something else. This works better: “That’s a really smart, original idea. I’d love to schedule a time to chat with you about this idea once these projects in our current pipeline are completed.”


What works and what doesn't work

​​Take time to debrief your team and review what worked and what didn’t. Every member contributes to this crucial conversation about the process, production, and execution. Blaming and shaming do the exact opposite of what you want to accomplish in a crucial conversation. Too many conversations generate only ideas but no action items. Results are paramount when having a crucial conversation.


Most importantly, after having a crucial conversation, both parties must agree to list what isn’t working. Suggest action items to create positive movement. Create the next steps. Set a date to meet again to discuss and measure progress. 


Don’t say: “Our new client numbers are down. I don’t know what to do because I don’t do new client meetings, but it’s going to cause a cash flow problem.”


In the example above, a problem is insinuated, but no potential solutions have been offered.


Do say: “Our new client numbers are down. Our referrals are on target, but our conversions are down thirty percent. Something isn’t working. Can we brainstorm plans to increase conversions? I know you handle the new client meetings, so I wanted to talk to you and ask what you think can be done.” Crucial conversations present problems and potential solutions with a calm, mindful, and empowered demeanor.


Asking empowering questions

The key to making these difficult conversations impactful is asking empowering questions. Empowering questions make the other person rethink their response. Find below some examples of such questions.


From the boss to employee:


1. What hasn’t happened that you had hoped to see by this point?

2. What opportunities do you believe we built barriers in front of?

3. Why can’t we make these opportunities real?

4. From your perspective, what things are currently working?

5. From your perspective what things need to change?

5. From your perspective what things need to change?

6. If we had a magic wand, what would make you wholly satisfied ninety days from now?

7. What do you need from me right now to feel valued and supported?


From employee to boss:


1. What hasn’t happened that you had hoped to see by this point?

2. What opportunities do you believe we built barriers in front of?

3. Why can’t we make these opportunities real?

4. What is currently working from your perspective?

5. What is currently not working from your perspective?

6. If we had a magic wand, what would make you wholly satisfied ninety days from now?

7. What do you need from me right now to feel confident enough for you to fully let go of control?


More tips to encourage crucial conversations

  • Shut the door. It’s that simple. It’s hard to be empowered with interruptions and outside distractions.

  • Uninterruptible. If the conversation isn’t scheduled, ask if the person is “interruptible.” Don’t ask if they are busy. We are all busy. That question puts the other person on the defense before you start. Also, it’s a sign of respect to ask if someone is interruptible, and their willingness to stop to talk with you lets you see how much that person respects you.

  • Turn off cell phones. Nothing is more disrespectful than taking up someone’s time for a conversation and then stopping to text or answer your phone.

  • Start with a “thank you.” Again, simple. Start with, “Thank you for taking the time to talk with me.”

  • Begin with your goal, the “who,” and the “what.” Rather than starting with an explanation that the other person may not follow, begin by stating your goal. “I’d like to talk for a minute about how to get better turnaround times. I have some ideas I’d like to share.”

  • Write down your points. It’s easy to get emotional and off track during a tough conversation. Write down your key points to keep yourself on track and avoid getting flustered. Your notes will also separate emotions from facts.

  • Be clear on your intentions. The other person may not agree, but you can maintain, or even earn, their respect. Always be clear that you’re bringing up a problem to come up with a solution, not to complain or vent.


Remember that communication is a choice. We have the power to choose how we talk with those in our space as well as if we talk at all. And silence may be even more detrimental than thoughtless conversation. Silence causes us to falter on our collective company goals.


Molly McGrath is the Founder and CEO of Hiring & Empowering Solutions and the author of Amazon's top #1 Best Seller: 'Fix My Boss: The Simple Plan to Cultivate Respect, Risk Courageous Conversations, and Increase the Bottom Line.'


She is a thought leader with 27 years of experience in the CEO space. Since the late nineties, Molly has coached, consulted, and directed presidents and founders of national organizations and over 4,500 law firms in executive-level leadership, continuous improvement, and team empowerment initiatives to infiltrate new markets, leverage partner ecosystems, and produce profitability.


Molly has 27 years of specific skill set experience in legal marketing, fractional CEO roles, conversation intelligence coaching, team development & empowerment, intrapreneur talent acquisition, Kaizen leadership, root cause analysis, revenue mapping, and action-based project management. #MollyMcGrath #communication #lawfirm



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