Delivering Difficult Messages

Tools to tackle dreaded conversations





No one relishes an uncomfortable conversation. When the best interests of a company, firm, individual or the public are threatened, it’s important to “be a leader” and take on the task.

A three-stage process can be relied on to broach any uncomfortable conversation: (1) gaining clarity about the message, (2) overruling avoidance with courage, and (3) executing the message.

The biggest obstacle between you and delivery of the message is avoidance, which often reveals itself in the form of “over-caring” for the person. To combat avoidance, ask yourself: (1) Is initiating this discussion serving the best interests of the person in question; (2) would delivering this message be consistent with my (or the firm or company’s) desired reputation; and (3) are the justifications for not delivering this message driven by emotional factors?

Executing delivery of a difficult message requires directness and sensitivity, which is most effective when communicated within the first 30 seconds of a difficult conversation. Saying “I” rather than “you” regulates blame, disarms defensiveness and claims responsibility for the message.

John J. Engels is president of Leadership Coaching Inc. in Rochester, N.Y. His e-mail is

Darla faced a dilemma. As the partner in charge of auditing for a mid-size firm, she had to respond to a new, not-for-profit client that had overspent its assets and was using restricted gifts to fund its operations. The client did not want to take responsibility for its actions, instead blaming the predecessor auditor. At such an early point in her firm’s relationship with the client, Darla felt uneasy challenging her client’s irresponsibility, especially in front of the board of directors. But Darla realized that she had an ethical obligation to take the appropriate course of action. Darla’s decision to overrule her fear of losing the client by holding the executive director and board accountable produced a few tense minutes but ultimately won the client’s respect.

No one relishes an uncomfortable conversation. Internally, it’s easy to avoid potentially volatile topics such as a cut in pay, a colleague’s terrible body odor, unacceptable project performance or the sudden departure of a valued client. Externally, as in Darla’s case, it’s emotionally—and at times, financially—costly to speak the unvarnished, unpopular truth to a client. But sidestepping tough discussions can leave important issues unaddressed, creating even bigger problems in relationships. That’s why it’s important to learn how to deliver difficult messages.

When the best interests of the public, a company’s stakeholders or of other individuals are threatened, it’s important for leaders to “take on” the difficult message—even if that message triggers emotional discomfort in the sender and is likely to do so in the receiver. Executing important but unsettling conversations can be surprisingly effective when the sender follows clear guidelines.

A time-tested, three-stage process can be relied on to broach any uncomfortable conversation. These three stages include:

  1. Gaining clarity about the message.
  2. Overruling avoidance with courage.
  3. Executing the message.

Clarity refers to the quality of a message that enables it to be understood and considered. Nothing is less helpful than communicating an unclear or accusing message. The chances of clear communication increase when the sender thinks carefully beforehand about what to say.

Is the problem that Sarah, a junior auditor on your team, missed an important deadline today, or that she has done so three times in the last month? When an outside auditor discovers a material weakness in internal control, does the auditor report it immediately to the responsible CFO (which is permitted by GAAS), or wait to report it using the mandatory written report to the audit committee and management? When messengers ask themselves, “What’s really going on here?” their clarity is sharpened.

Judy, a CPA in a small firm, routinely received project directives for the same day from two partners. For weeks, she worked long hours to tackle an overload, and she became more and more resentful along the way. When she finally approached the partners, Judy’s angry message was, “I’m sick and tired of working 70 hours a week while you guys are playing golf every other day.” But Judy’s message missed the real issue, namely, that the partners’ lack of communication with each other resulted in her chronic state of task overload. “I am requesting that you two prioritize projects with each other before sending them to me,” would have been a more effective message from Judy.

Clarifying the message you want to deliver requires calmness and careful thinking. When you are angry or anxious is not the best time to formulate your message. It’s better to step back, calm down, put the issue in perspective and think through the most sensible approach. High anxiety is a barrier to clear thinking.

  Courageous Communication…

Confronts repeatedly unacceptable behavior.

Holds others accountable in the face of resistance.

Respectfully challenges a high-profile client.

Delegates responsibilities instead of protecting weakness.

Discusses a “taboo” hygiene or dress issue.

Acknowledges a mistake before being “caught.”

Thoughtfully says “no” instead of automatically saying “yes.”


After establishing the message you want to deliver, the biggest obstacle between you and the delivery of the message is avoidance. Avoidance is all about fear. Fear-based excuses come in deceptive packages. Some masquerade as “caring about” the recipient, “I wouldn’t want to hurt Mary’s feelings….” Others are cloaked in procrastination, “This isn’t the right time to sit down and discuss it.”

David, the president of a prominent software engineering firm, found himself avoiding a conversation with his chief financial officer about the CFO’s excessive drinking at a community fundraising event. “Some of his language and jokes were inappropriate, but he wasn’t stumbling drunk,” David rationalized. “I wasn’t sure I wanted to make an issue out of it. I knew I was procrastinating, but I didn’t want him to think I see myself as ‘holier-than-thou.’ We all make mistakes.”

To combat over-caring and other forms of avoidance, ask yourself three questions:

  1. Is initiating this discussion serving the best interests of the person in question?
  2. Would delivering this message be consistent with my (or the firm’s or company’s) desired reputation?
  3. Are the justifications for not delivering this message driven by emotional factors such as my fear of hurting the other’s feelings, my fear of rejection or my lack of confidence in myself to skillfully execute the message?

If the answer to all three questions is “yes,” then turn your attention to timing. Does it make more sense to wait or act now? If you do not have a clear rationale for waiting, it’s time to act.

Confusion and avoidance are common roadblocks to addressing uncomfortable issues. Clarifying the message and mustering the courage to overcome avoidance brings you to the doorstep of execution. Now, let’s think about how to actually deliver the message.

  Signs of “The Avoidance Virus”

Procrastinating without a clear rationale.

Ignoring important conversations.

Sidestepping tough decisions.

Allowing short-term reactions to overrule long-term thinking.

Choosing comfort over progress.

Putting harmony before integrity.

Superficial, risk-averse “beating around the bush.”

Blaming others (avoiding looking at self).

Talking about symptoms instead of understanding the wider problem.


Execution requires two critical elements: directness and sensitivity. A message that is direct and insensitive uses too much force and will not be heard. A message that is sensitive and indirect will get heard, but without understanding. The middle ground of “tough compassion” combines directness and sensitivity, enabling a message to be both heard and understood.

Communicating directness and sensitivity within the first 30 seconds of a difficult message increases the chances of a positive outcome. Returning to Darla’s dilemma, the following examples illustrate important differences in opening a difficult conversation:

Example 1: Direct and Insensitive (ineffective)

“You’re passing the buck, and you have to change.”

Example 2: Indirect and Sensitive (ineffective)

“Is there any chance there’s something here you’re not seeing?”

Example 3: Direct and Sensitive (effective)

“It’s part of my job to point out problems in order to protect the public interest and save you grief down the road. Those problems include using restricted gifts to fund operations and overspending assets. These issues are the organization’s responsibility to monitor and address. I want to help you figure out how to do that more effectively.”

  When Delivering Difficult Messages, Avoid…

O rdering, Directing: “You have to...”

Warning, Threatening: “You’d better not...”

Preaching, Moralizing: “You ought to...”

Advising, Giving Solutions: “Why don’t you...”

Evaluating, Blaming: “You’re wrong...”

Interpreting, Diagnosing: “You need to...”


Many people believe that engaging in several minutes of small talk and “beating around the bush” cushions the harshness or surprise of a difficult message for the recipient. In truth, superficial preambles more likely serve the emotional interests of the sender, hearkening the presence of “the avoidance virus.” If someone had something difficult to say to you, would you rather have the person dance around the subject for several minutes or get right to the point?

The use of the pronoun “I” is a final consideration in communicating unsavory messages. The use of “I” language serves the three fold purpose of regulating blame, disarming defensiveness and claiming responsibility for the message. Unlike “I” messages, “you” messages provoke defensiveness and invite rebuttal. Consider the following difficult message delivered by a vice president of finance to a hospital’s chief of medicine:

Example 1: “You” language (ineffective)

“You are constantly asking for exceptions when it comes to proper documentation.”

Example 2: “I” language (effective)

“I see the documentation procedures being sidestepped, and I want to explore with you how to make it better. I would like to begin meeting with you once a week to look at specific tension spots and brainstorm solutions…”

“I” messages are powerful because they reduce argumentation. It is difficult to attack someone who is exposing genuine thoughts and feelings. In fact, “I” messages increase the clarity and effectiveness of all verbal communication, not just emotionally tense messages.

Becoming accomplished at “tough compassion”—combining directness and sensitivity in the same message—is a lifelong challenge. Reading this article is best viewed as a launching pad with a long flight ahead.

The good news is that opportunities abound for practicing this vital life skill at home, work and in all private and commercial interactions. Delivering difficult messages is part of day-to-day life in all social groups, whether the organization is a family, a nation or a business. Learning how to do it well—with clarity, courage and skill—reduces the anxiety of initiating uncomfortable conversations and benefits the recipient as well as your organization.


Where to find January’s flipbook issue

Starting this month, all Association magazines — the Journal of Accountancy, The Tax Adviser, and FM magazine (coming in February) — are completely digital. Read more about the change and get tips on how to access the new flipbook digital issues.


Get your clients ready for tax season

Upon its enactment in March, the American Rescue Plan Act (ARPA) introduced many new tax changes, some of which retroactively affected 2020 returns. Making the right moves now can help you mitigate any surprises heading into 2022.