Difficult Manager-Staff Conversations
By Russell Jay Hendel
The Stepping Stone, September 2025
Introduction
This article reviews, discusses, and critiques several approaches for difficult conversations between managers and staff. Several strategies and a diverse set of case studies are presented.
However, before beginning, we review guidelines for ordinary conversations which will enable us to more sharply focus on those guidelines unique to difficult conversations. Table 1 presents five guidelines and is based on a similar table in endnote[1] which draws from a commonality of themes in guidelines for email etiquette[2]and the Laws governing Speech in Jewish law.[3]
Table 1: Guidelines for Ordinary Conversations
| Name of Guideline | Brief Description |
|---|---|
| Real world | Whenever possible, focus should be on real-world—and hence objective—facts, rather than on people. |
| Fix it | It is better to state what has to be done and how the problem should be fixed, than to focus on criticism of, and blame on, past behaviors. |
| Holistic | Besides identifying what has to be fixed, a conversation should be holistic, acknowledging things already done properly. |
| Operational | Requests for outcomes should be accompanied by concrete operational suggestions on how to achieve these outcomes. |
| Tentative Tone | Tone should be one of possibility rather than conclusory, for example, by using the interrogative vs. the indicative. |
The STATE Strategy
We begin the review of effective strategies for difficult conversations with the STATE method, compactly but comprehensively summarized in Table 2, and advocated by several authors.[4,5]
Table 2: Summary of STATE Guidelines
| Name of Guideline | Brief Description and Rationale |
|---|---|
| Share facts | Facts, relevant to the discussion, are a good way to begin a conversation since facts are the least controversial, least likely to offend, and the most compelling to accept. Facts refer to statements about the world, not statements about people, which are actually interpretations of the facts. |
| Tell your story | Building on the facts, state your interpretation of them, what is bothering you. |
| Ask for other’s point of view | By building on a foundation of facts, you lay a commonality to which you add “here is my perspective” and then allow the person to whom you are speaking to give their perspective. |
| Tentative in assertions | By using tentative vs. conclusory statements, you show your sincerity in wanting to hear other ways of interpreting the facts. |
| Encourage Testing | With both perspectives on the facts exposed (your interpretation leading to criticism and their interpretation) you can begin to show flexibility in next steps. |
Critiques and Other Guideline Sets
The STATE guidelines for stating facts and using a tentative vs. conclusory tone are included in the guidelines for ordinary conversations reviewed in the introductory section. What is new in STATE are the ideas of active dialogue, active listening, sharing of interpretations and perspectives, and being flexible.
Our critique is that this is not operational:
- What should a person do to engage?
- How is behavior different for active listening?
- What specific techniques can be employed to accomplish this?
The answers to these questions are the main contribution of this article. We will obtain the answers through five case studies and then summarize in the conclusion.
Before proceeding we acknowledge other guideline sets which also lack operationality. Some of these guideline sets emphasize relationship as the key to success. Others emphasize self-control. But again, relationship while having definite meaning, lacks specificity. Dealing with flaring emotions will be encountered several times in the case studies.
We specifically mention five other sets of guidelines:
- The Office of Personal Management (OPM) of the U.S. government, advocates the OCEAN guidelines: Opening with necessary background including the reason for the meeting, Creating expectations by describing gaps, Engaging in active dialogue and listening to establish further expectations, Agreeing on the issue and collaborating on finding possible solutions, and Establishing next steps including a plan of action and commitments;[6]
- The Army Resilience Directorate advocates the three C’s guidelines: Communicate clearly, Communicate confidently, Control your emotions;[7]
- Harvard Business Review advocates the following guidelines: Have a positive mindset, Breathe, Plan but don't script, Acknowledge other's perspectives, Be compassionate and understanding of the person you are speaking to, Slow down and listen, Give something back, and Reflect and learn;[8]
- American Express advocates a 12-step set of guidelines: Be clear about the issue, Define your objective, Be open-minded, Manage emotions, Embrace the silence, Preserve the relationship, Be consistent, Develop conflict resolution skills, Keep moving forward, Choose the right place for the conversation, Know how to start, Be mindful of mind and body language;[9] and
- Endnote[10] advocates a relationship-based approach: Check into feelings, Actively listen, Use reflective questions (e.g., What was the difficulty? or How can we improve things?), Focus on solutions, and Give follow-up steps.
Case Study #1: Shared Self Evaluation[8]
All case studies are presented as triples: situations, dialogues, and lessons learned. Throughout the studies, M and S stand for manager and staff (this is true even when the terms don’t strictly apply such as a class visitation (M) of a teacher (S)). Dialogues are presented as conversations between M and S with parenthetical inserts indicating either summaries or attributes of the dialogue.
Situation:
M had to fire S because his position was being eliminated, and it was less relevant to the company. M chose to deliver this difficult conversation through multiple sessions.
Dialogue:
Session 1:
M: S, how are things going for you at work?
S: (Replies)
M: I don’t see it that way. Here are some concerns I have.
S: (Becomes very defensive)
M: Let's continue this conversation later
Session 2:
M: Have you thought about our previous conversation?
S: Yes, I am beginning to see what you are saying. My work is fine, but my position is now less relevant to the company.
Final Session:
S: I have thought over our conversations. I have applied and been accepted for a position elsewhere.
M: (They parted as good friends and hugged each other).
Lessons learned:
S achieved her goals through (i) skillful use of breaks into several sessions (when initial emotions started to flare) and (ii) soliciting shared self-evaluations accomplished through S asking M to self-evaluate. Notice that this shared self-evaluation simultaneously achieves the goals of openness to different perspectives and active listening. It is also operationally specific; ask the other party to perform the same evaluation you have done. Also notice how the difficult conversation ended with harmony, friendship, and agreement (not always present in firings).
Case Study #2, Rent Delinquency
Situation:
The following situation was experienced by the author (S) who rented property from M but had since moved from the college he was working at. I didn’t give up the property since I travelled there frequently, as I had several friends in the town. One day I received a subpoena, based on rent delinquency, to appear before a court, now, several hundred miles away. I initially thought the accusation ridiculous. So, I checked cancelled checks and was embarrassed to find that indeed I had stopped paying rent
Dialogue:
S: (Self dialogue) How do I get out of this? I have to figure out what is bothering M. Clearly M wants his money back. But M presumably doesn’t trust me anymore, making our future relationship difficult.
I devised a strategy based on this self-evaluation.
S: (I spoke to the attorney for M) Hi. I checked my records and embarrassingly found that the subpoena was correct. I would like to correct the situation. In addition to paying all owed rent, I voluntarily agree to pay a year’s rent in advance on January 1st assuring that this doesn’t happen again.
M: (Money goes a long way in this business. M’s attorney then did legal work for me at no charge; he went through the process of removing the subpoena and drawing up the appropriate papers. Years later, due to hurricanes, M had to file for bankruptcy. I had a dialogue with M; we reminisced about the entire incident and parted as good friends with my wishing him luck.)
Lessons learned:
Notice how there was no dialogue from M to S (only a court subpoena). However, the shared self-evaluation functioned as a dialogue and active listening enabling a happy ending for the story.
Case Study #3, King David’s Adultery[11]
Situation:
David (S), the monarch of ancient Israel, had an affair with the wife of one of the soldiers in his army who in fact got pregnant. When the husband (out of respect and empathy for those fighting) did not accept an invitation by David to take leave and visit his wife, David ordered him to the thicket of battle where he was killed. David then married the person with whom he had an affair. Nathan (M), the personal prophet of David, had the difficult task of explaining to David how evil this was and that he would be severely punished.[11]
Dialogue:
M: I have a case that perhaps you can help me with. A poor person, a neighbor of a rich person, had one valuable asset, a sheep which provided yields from which the poor person’s family lived. The sheep was also like a pet to the family, partaking with them at meals and other personal occasions. But one day, when a guest came to the rich neighbor, the rich person prepared a meal for the guest by slaughtering the sheep of the poor person.
S: Outrageous! The rich person deserves death. (The strict letter of the law requires that) he must compensate the poor person with four times its worth.
M: You are the rich person! When you had a need for an additional wife, and could pick from the entire nation, you instead chose to take the wife of your loyal soldier.
S: I have sinned to God.
Lessons Learned:
We again see here how shared self-evaluation is a concrete, specific, easily applied technique, which can substitute for, or supplement relationships, dialogues, and sharing of perspectives.
Case Study #4: The Korax Rebellion[12]
Situation:
Moses (M), with the assistance of Divine Providence, had enabled the Jewish people, with slave status in Egypt, to leave Egypt and become an independent nation. But Korax (S) rebelled against him.
Dialogue:
S: M, you assert you are leader because you are a prophet with liaison to God. But the entire nation had prophetic encounters with God at the Revelation of the Decalogue. So why do you persist as leader?
M: Let’s talk about this in the morning (translated to mean, perhaps you are drunk; why don’t you sleep it off and we can talk in the morning[12]).
Lessons learned:
In Case Study #1, we encountered the use of breaks (aka silence) when emotions begin to flair. These breaks facilitate a more logic-based approach. Similarly, The Harvard Business Review advocates the embracing the silence guideline. While there is much in the literature about emotions and their control, this paper is more modest: Use breaks if and when emotions flair; otherwise use the various logic-based approaches available including those presented in this paper.
Case Study #5, Open-ended Questions, Empathy[10]
Situation:
During a class visitation by an observer (M), a teacher of young children (S) rolled her eyes at a student, X. During the visitation she was visibly annoyed with X, and appeared overwhelmed.
Dialogue:
M: S, how are you feeling today? Do you want to talk about anything?
S: I have been having a rough day.
M: I know how frustrating it is to have rough days.
S: Yes, it was an off day. X was annoying me. The stress of the visitation added to my frustration.
M: I know visitations can be stressful. Can I do anything to support or help you?
S: (There ensued a discussion about Student X).
M: I did notice X’s annoying behavior. Can I do anything to support you in future interactions with X?
Lessons learned:
The emphasis in this case study is on building relationships. Notice how the dialogue does not begin with a discussion of the problem but rather with a sharing of feelings. As the dialogue continues, notice how M several times is empathic, shares feelings with, and offers support to, S. Importantly, note how the rapport of the conversation naturally led to a discussion about X, which was first brought up by S, not M.
We can summarize this technique as follows: Offer support, not blame, and continuously be empathic and acknowledge statements of feeling. Additionally, open-ended questions may help ease the conversation into the discussion of difficulties. Importantly, this guidance is consistent with the five guidelines for ordinary conversations presented in Table 1.
Interestingly the Bible in several places records the approach of open-ended questions which however failed (possibly because of the gravity of the situation):
- When Adam and Eve violated God’s command not to eat fruit from the Tree of Knowledge, God opened the conversation with “Where are you?” (perhaps better translated as “How are you?”) hoping to lead Adam to confess and seek help, but this instead resulted in evasiveness (“The wife you gave me, gave me the fruit and I ate.”);[13]
- When Kayin killed his brother Abel, God opened the conversation with “Where (how is) your brother?” hoping to lead Kayin to confess and seek help, but this instead resulted in evasiveness (“Am I my brother’s keeper?”).[14]
- Similar evasiveness is shown by Balak, Hezkiah and Ezekiel.[15]
This leads to the observation that all techniques mentioned in this article are possibilities, not guarantees, to facilitate and ease difficult conversations. They frequently do work, but sometimes don’t.
Conclusion
This article has reviewed a variety of both strategies and case studies related to difficult conversations. Besides techniques useful for any conversation reviewed in the introductory section, we introduced the ideas of shared-self-evaluation, skillful use of breaks when emotions flair, and use of open-ended lead-on questions coupled with continuous empathy and offers of collaborative support. We hope readers find these ideas useful in their own conversations.
This article is provided for informational and educational purposes only. Neither the Society of Actuaries nor the respective authors’ employers make any endorsement, representation or guarantee with regard to any content, and disclaim any liability in connection with the use or misuse of any information provided herein. This article should not be construed as professional or financial advice. Statements of fact and opinions expressed herein are those of the individual authors and are not necessarily those of the Society of Actuaries or the respective authors’ employers.
Russell Jay Hendel, Ph.D., ASA, is the vice-chair of the Leadership and Development Section Council. He is adjunct faculty III at Towson University, where he assists with the Actuarial Science and Research Methods program. He can be reached at RHendel@Towson.edu.
ENDNOTES
[1] Russell Jay Hendel, “Negative Leadership,” The Stepping Stone, June 2025, https://www.soa.org/sections/leadership-development/leadership-development-newsletter/2025/june/ss-2025-06-hendel/.
[2] Melanie Dunn, "Email Strategies," Actuary of the Future, January 2020, https://www.soa.org/490e4d/globalassets/assets/library/newsletters/actuary-of-the-future/2020/january/aof-2020-iss-01-31.pdf.
[3] Yisroel Meir Kagen, Sefer Chofetz Chaim (English Translation) (Boston: Israel Book Shop, 2015).
[4] John Berardi, PhD, "Reputation" in Change Maker (Dallas: BenBella Books, 2019).
[5] Kerry Patterson, Joseph Grenny, Ron McMilla), and Al Switzler, Crucial Conversations (New York: McGraw Hill, 2021).
[6] Office of Personal Management (OPM), Best Practice Module of the Difficult Conversations for Supervisors Course (OPM), https://www.opm.gov/policy-data-oversight/training-and-development/reference-materials/online-courses/difficult-conversations/difficultconversations.pdf.
[7] https://www.armyresilience.army.mil/ard/R2/pdf/Navigating-RIF-graphic.pdf.
[8] Rebecca Knight, “How to Handle Difficult Conversations at Work,” Harvard Business Review, Jan. 9, 2015, https://hbr.org/2015/01/how-to-handle-difficult-conversations-at-work.
[9] Bruna Martinuzzi, “12 Tips for Handling Difficult Conversations,” American Express.com, Oct. 4, 2022, https://www.americanexpress.com/en-us/business/trends-and-insights/articles/top-ten-tips-for-handling-the-difficult-conversation/.
[10] Hayley Jackson, Rachel E. Schachter, Holly Hatton-Bowers, Lisa L. Knoche, “Coaching in Difficult Conversations: A Relationship-Based Approach,” Young Children 78, no.3 (Fall 2023): 80–87.
[11] Bible, Samuel 2, Chapters 11 and 12.
[12] Bible Numbers, Chapter 16. See especially the commentary of Rashi on verse 5 available online at https://www.chabad.org/library/bible_cdo/aid/9944/showrashi/true.
[15] Bible, Num. 22:9–21, Kings II, 20:12–19, Ezek. 37:1–14.