Having Difficult Conversations; The Do’s and Don’ts

I am often asked about how to have “difficult conversations” in which one person tells another that what he/she is doing is problematic and needs to change. This is feedback. If you can give, receive and digest feedback well, difficult conversations will become much easier.  Typically it is easy to give/receive/digest “positive” feedback, but “negative” feedback can feel like a difficult conversation.  Hence this article.

The ability to give, receive and process feedback is a critical capability for lawyers.  Younger lawyers are often on the receiving end, while senior lawyers often give feedback. It’s a vital component of team management, the appraisal/promotion process and survival in the practice of law.  In your dealings with clients too, giving/receiving feedback well is crucial. 

Consider the following. You are about to be served a meal. If the chef and wait staff have observed you and tailored the food and service to your needs, the dining experience is likely to be positive. Conversely, if no one pays attention to you and serves you a one-size-fits-all meal, you may get indigestion afterwards. The same is true of feedback.

In his wonderful book, Helping, Edgar Schein defines feedback as “information that helps one reach goals by showing that the current progress is either on or off target.”  So, what are the elements of optimal feedback and how do you incorporate those in your interactions with others? How can this convert a “difficult” conversation into a positive dialogue?

Giving Feedback  

The Context. When you give feedback, getting the context right really matters.  Both parties must be ready to give and receive feedback.  Think about the following:

  • Timing.  Should the conversation occur in the morning, over lunch, at the end of the day, at the beginning of the week, before a weekend and so forth?
  • Background Information.  Do you have sufficient detailed information to provide helpful feedback? Do you know enough about the other person so you can tailor both the content and style to the recipient?  If not, your feedback may not be heard.
  • Motivation Level.  Are both parties highly motivated to engage in the conversation? Are you ready to give the feedback and is the recipient ready to hear it?
  • Trust.  Is the feedback discussion occurring in the context of a high trust relationship? High trust relationships result from interaction, disclosure of important information, flexibility, good intentions and consistency in behavior over time.
  • Setting. The setting for the conversation should be private and comfortable. Be sure both of you have enough time to have the discussion in a considered and deliberate way.

Pay attention to the details and get these right the first time. Once feedback has been given, it is difficult to take back. To be effective, feedback must take into account what you know about the recipient, coupled with a certain level of empathy and insight about yourself and the other person.

The Delivery.   Before you give feedback, think about how you want to manage yourself in the conversation.

  • Choreography.  At the outset of the discussion, provide a brief outline of what you intend to discuss, stick with your agenda and bring graceful closure to the process at the end. I usually describe what feedback is, what my intentions are for the discussion, what success might look like. I encourage questions/discussion and summarise the feedback when the time is right.  This process settles me down and seems to do the same for the recipient.
  • Emotional Reactivity.  Take the time to get yourself completely comfortable with the message you plan to deliver so your anxiety level is as low as possible. Remember; anxiety is fear in search of a cause and it can be contagious. If you are anxious, you are likely to be emotionally reactive and less logical in your delivery. Pay particular attention to your feelings of anger, frustration and guilt.  Try to be as neutral as possible, while being supportive of the other individual.
  • Open-mindedness.  When you give feedback, you will likely have  objectives in mind about attitudinal and behavioural changes you would like the recipient to make. Nevertheless, try to be as open to various outcomes as possible. The recipient may achieve your objectives, but do so in ways that have not occurred to you. Be open to that possibility.
  • Self Evaluation.  Before you give feedback, consider asking the feedback recipient to reflect on what he/she thinks we might discuss. Frequently, before I give a client feedback about his/her blind spots, I will ask the client to tell me what he/she thinks the feedback might include. Usually, the recipient intuitively knows what I’ll be saying and by articulating the “hard bits” him/herself, it makes it easier to hear what I’m about to say.
  • Reciprocal Feedback.  During the course of the feedback discussion, both the giver and the receiver should engage in neutral, reciprocal feedback. For example, I will enquire how the client is doing, whether the feedback is clear, does he/she have any questions, does he/she need more/less detail etc.  This creates more equality in the discussion and enhances outcomes. Consequently, I’m better able to tailor my message.

The Content.

  • Detailed Roadmap.  When you give feedback, articulate a framework for the discussion. Tell the recipient what general topics you will be discussing and fit the details into these. If possible, incorporate both positive and negative feedback, starting with the positive. For example, if I am giving someone feedback on their blind spots, I first focus on their strengths and then I define what I mean by a blind spot (“A blind spot is something that other people know about you but you do not know about yourself”). I then break the feedback down into categories including self-presentation skills, communication capabilities, body language, work styles and so forth. Within each of these categories, I provide detail about the recipient’s behaviour. I make the feedback constructive, while also being very direct. I don’t “pull punches”, but I do ensure that every piece of information will be meaningful and tailored to the recipient.
  • Action Plan.  After giving/discussing the feedback, I move quickly into concrete next steps and provide the client with a “menu” of possible options.  I encourage the client to choose  two to three “menu items” to act on immediately.  These should be things that the recipient can do easily to experience rapid success. For example, I worked with a lawyer who had difficulty collaborating with his colleagues. Amongst other problematic behaviours, he used strong language and had an astonishingly messy office. He committed to eliminating the strong language and the next weekend he and I together cleaned up his office. The impact was immediate and powerful for him and for others. His colleagues spontaneously began giving him positive feedback. This gave him the self-confidence to address some of the other more difficult behavioural and attitudinal changes he needed to make.
  • Feedback Loop.  Once a client has identified his/her next steps, we set a date to meet again and reflect on how those changes went. In other words, there is a clear commitment to follow through and a high-level of accountability in the feedback process.  It’s not a one-time intervention; it’s part of a clearly articulated mutual process.

Following Up. After the feedback discussion, the feedback giver and recipient must gradually determine to what extent the recipient can change his/her behaviour and attitudes based on the feedback. If the feedback conversation was significant and it went well, it can be the turning point in someone’s career. Other times, the outcome is helpful but reasonably neutral. Conversely, sometimes the fit is wrong and it becomes clear that a situational change is necessary. If that occurs, follow-up discussions with the recipient are best done in the same way as the initial discussion, but with a focus on changed outcomes. For example, years ago it became obvious to me that my long time secretary was failing to adjust to the changing needs of her job. After a couple of good feedback discussions, we both realised it would be best for her to leave. When she left, she felt good about herself as well as the office, and departed with our support and best wishes.  The process had worked.

Receiving Feedback

If you are the recipient, here’s how to get the most out of that experience.

Active Listening.  Be an active listener, pay attention to what  is being said and suspend your own thinking and reactions while you listen. You will have plenty of time afterwards to reflect on the feedback. By actively listening to the feedback in the moment while it is being given, you will reduce your own anxiety level, bring a neutrality of thinking to the experience, suspend your own judgment for the time being and bring a dignity to the experience that you would likely otherwise not have had.

Participate but Don’t Debate.  Do ask for clarification if something is said that you do not fully understand. Make excellent eye contact, use body language to show engagement, and be as comfortable in the setting a possible.  In your thinking, choose to apply the “1% rule” to the experience. By this, I mean that even if it feels as though 99% of the feedback you are being given is either irrelevant or inappropriate, assume that at least 1% will be extremely valuable, appropriate and worth pursuing. Don’t be argumentative or confrontational.  You can discuss the merits of the feedback later on if appropriate, after you have reflected on what you’ve been told. Try to keep an open mind.

Appreciation.  Following the feedback discussion, always thank the person who gave you the feedback for having done so. Likely, giving you feedback was difficult for the other person and expressing your appreciation will be helpful. It also will increase the likelihood of positive future outcomes for you.

Digesting the Feedback

Digesting feedback means acting on the feedback you have been given to optimise the benefits for you and others.  You have choices about how to utilise feedback and the attitude and intentions you bring to the process. Be positive and constructive, don’t vilify the person who gave you feedback, initiate follow-up conversations with the feedback giver if appropriate, don’t gossip, be honest with yourself, own what is yours, don’t blame others, and commit to being as personally accountable as you can be. If you can do this, then the outcomes will be positive for you, regardless of what happens.


If giving, getting and digesting feedback is like a dining experience and the context, delivery, content and receipt are done professionally, than the dining experience will be optimal. Paying attention to detail, being empathetic, thoughtful and mature, investing the time and energy it deserves and valuing the experience will make all the difference. Bon appétit! EMILY MORROW, BA (Hons), JD (Hons, Juris Doctor), was a lawyer and senior partner with a large firm in Vermont, where she built a premier trusts, estates and tax practice.  Having  lived and worked in Sydney and Vermont, Emily now resides in Auckland and provides tailored consulting services for lawyers, barristers, in-house counsel, law firms and barristers’ chambers focusing on non-technical skills that correlate with professional success; business development, communication, delegation, self presentation, leadership, team building/management and the like.

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