Tough Talks: How to find success with difficult conversations and move forward productively

Journal of Financial Planning: March 2019​​



Barbara Kay, LPC, RCC, ( is a business psychology and productivity expert who coaches and speaks nationwide. She specializes in growth, productivity, teams, clients, change, women, and leadership. Joining the FPA Coaches Corner in 2019, she now offers free coaching to FPA members.


Epictetus, the greek philosopher of stoicism, shared this wisdom in the first century: “We have two ears and one mouth so that we can listen twice as much as we speak.” Irish philosopher and playwright George Bernard Shaw famously quipped: “The single biggest problem with communication is the illusion that it has taken place.” More recently, renowned leadership consultant Peter Drucker said: “The most important thing about communication is hearing what isn’t said.”

Clearly, despite 2,000 years of accumulated knowledge, we still struggle with communication. I’m frequently asked, “How do I talk to this upset client?” “How do I diplomatically correct this team member?” “How do I share my concerns with my partner without offending?” We struggle to communicate productively, especially when dealing with potential conflict or upset people.

Why is it so hard? The short answer is the layered complexity of human interaction. Everyone communicates within a context of individual interpretation, motivations, emotions, and goals, which are often hidden beneath the verbal conversation. Words are just the tip of the interaction iceberg. It’s remarkably easy to smack into obstacles that disrupt the communication and the relationship.

Fortunately, we have sound techniques to navigate the murky waters of human interaction. First, start with the powerful reconnaissance tool of listening. Second, clear any obstacles with seven steps to reach productive collaboration. Finally, use three techniques to engage cooperative problem-solving to reach final solutions.

How We Listen

How we focus a camera shifts what we capture in a photograph. Similarly, how we listen shifts what we capture in a conversation. The communication term for how we listen is our “listening style.” Our listening style changes the questions we ask, the responses we notice, the follow-up questions, and ultimately the course of the entire conversation. Each of the listening styles has a different goal and delivers a different outcome.

The five listening style goals and outcomes are:

Information—Gather facts and specific details.

Evaluation—Form opinions and judgments.

Solutions—Offer advice or deliver a solution.

Empathy—Understand feelings and connect emotionally.

Insight—Reveal hidden significance.

Financial planners and other expert professionals are trained to gather information, form professional judgments, and then offer advice. Consequently, most professionals are highly proficient at the first three listening styles—information, evaluation, and solutions—and use them automatically. Unfortunately, those styles are the least helpful in communication complicated by strong emotions, hidden motivations, or competing desires—those very difficult conversations.

Listening in Difficult Conversations

The first three listening styles focus the conversation on rational facts and analytical reasoning. Communicating on a rational level is only effective if the individuals are thinking with the rational centers of the brain. Unfortunately, when emotions, biases, drives, or instincts are triggered, the irrational part of the brain, the limbic system, is activated. The rational and irrational centers of the brain operate like a seesaw. When the irrational system is way up, reasoning is way down.

Too often we focus on rational solutions when rationality is down and the limbic system is up. This is why it’s so hard for people to move forward. Rational discussion does not resolve emotional concerns. The limbic system focuses on meeting emotional needs and drives. It seeks safety, comfort, approval, and pleasure.

Seven Steps to Productive Collaboration

In any potentially difficult conversation, start with the seven steps to productive collaboration. These steps address the needs of the limbic system and clear any emotional obstacles to rational problem-solving:

  1. ​Start with empathy and insight listening. Do not start with logical reasoning or analysis. This is especially true if an individual is clearly upset or anxious. Being very cool and rational with an emotional person tends to escalate the emotion. The limbic center is very insistent when triggered; ignoring emotion will only incite more emotional expression.
  2. Use your eyes. Look at their facial expression and notice the body language and tone of voice. These are great clues for any concerns hidden under the words.
  3. Listen for feelings. What feelings are coming out? Are they confused, frustrated, sad, worried, angry, or feeling guilty?
  4. Don’t be fooled by anger. Anger is human nature’s defense against vulnerability. Anger is an outward expression of deeper, more painful feelings of powerlessness, guilt, fear, betrayal, hurt, or despair. Listen insightfully for the painful feelings below the anger.
  5. Acknowledge. After listening and discerning feelings, it’s time to address the concerns. Acknowledge with the simple technique of reflection. In your own words, summarize both the emotional and factual content you heard from the individual. For example: “It sounds like you’re very worried that you might not have enough money for retirement.” Mirror the level of concern you picked up from listening empathically. Reflecting the emotion, the way they feel it, conveys that you hear their concerns. This is a powerful calming technique. It shows you understand and care about what matters deeply to the individual. It builds emotional comfort and connection.
  6. Normalize the feelings. Emotions can be very powerful and overwhelming. Assurance that the feelings are normal helps clear the emotion and the anxiety about the emotion. This psychological technique of normalizing greatly increases the feeling of safety and acceptance. It’s important to normalize the feelings without confirming factual exaggerations or errors. For example: “Of course you feel very anxious about your financial security in retirement, that’s completely normal. People want to feel secure about their future, and they worry if they’re not confident.” At this point, focus on the feelings.
  7. Uncover inferences and assumptions. After concerns are revealed, continue to uncover any hidden assumptions or inferences. Ask short, open-ended questions starting with “how,” “what,” or seek more revelation with a simple, “Tell me more about….” For example: How does that make you feel? What does that mean for you? Tell me more about what led you to expect that.

People’s anxieties are often escalated by hidden irrational assumptions. Eventually, we can address the erroneous beliefs, but they need to be uncovered first. For example, a reasonable discussion about retirement planning is not possible when a client is secretly convinced they will never be financially secure. The best reasoning will never satisfy an irrational fear lurking in the background.

While uncovering feelings and expectations, continue to acknowledge by mirroring and normalizing the feelings. As you notice the individual feeling more comfortable, transition to productive collaboration and reasoned solutions.

Three Techniques for Collaboration and Problem-Solving

Move ahead with agreement. The goal is to calm feelings and then engage cooperative problem-solving. This requires a careful transition. After acknowledging feelings, shift to discussing facts and solutions with a powerful bridge of agreement. Find at least one thing you can agree with sincerely. At the very minimum, agree on feelings expressed.

Only after agreeing, with​ full sincerity, move the conversation forward by adding a new point of view. You might say: “You’ve shared that you don’t know how much money is enough, and you’re afraid that you’ll never have enough. Of course you feel anxious. You don’t know if you’ll be OK! Fortunately, I’m here to develop a plan that helps you feel confident and reach your financial goals. Can I show you how that works?”

When adding your viewpoint, never use the word “but”—it erases your agreement. Also, it’s a good practice to end your transition with a question; this checks the readiness of the individual to move forward. Once the individual is ready to cooperate with you, engage the information, evaluation, and solution-focused listening styles. Move ahead with fact-based questions and collaborative problem-solving.

Repeat to stay on track. Hopefully, the conversation will proceed to a successful conclusion with mutual agreement and resolution. On occasion new or unresolved concerns will disrupt progress. In that case, stay on track by repeating with genuine empathy. For example: “Yes, I hear that you don’t understand financial planning and it makes you anxious. I’m here to help you feel better and reach your goals. Today, we need to make just a few decisions to move forward. Can we finish what we need to do today?”

This is called the broken-record technique. You respectfully repeat to bring the individual back on track toward the goal. This can work remarkably well. Notice the request to stay on track was combined with emotional acknowledgement and reassurance. Addressing the emotion helps the person stay focused on problem-solving. When people are upset, repeating the goal and continuing to reassure emotionally is frequently necessary. You may need to restate several times to gain full cooperation and reach resolution. Keep at it with genuine empathy.

Sometimes, an individual is so derailed emotionally they cannot move forward. If the individual remains stuck after numerous attempts to execute the entire process, it’s time for a time-out.

Time-out and try again. A communication time-out is called “meta-communicating.” Meta-communication is the process of verbally naming the unspoken realities of the conversation. It’s very helpful to notice both non-verbals and the overall progress of the interaction.

After meta-communicating, suggest an alternative. In the case of a very anxious client you might say: “I notice we’re not getting very far, and it seems you’ve hit your limit. Let’s look at the calendar and pick another time to meet. You’re no different than other clients. This is hard stuff. We’ve made a good start and it will feel good as we move forward.” Notice the continued normalizing and emotional reassurance. Upset people want to feel better. You paint a picture of success with a vision of happy feelings.

Success with Difficult Conversations

Ultimately, success with difficult conversations is a process of revealing and navigating the seen and the unseen, the rational and irrational. Discover and carefully clear emotional obstacles by addressing any limbic system needs first. This calms anxieties, strengthens cooperation, builds relationships, and leads to productive solutions. ​

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