New Zealand Law Society - The anatomy of a difficult conversation

The anatomy of a difficult conversation

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Phil, a senior partner at the fictitious law firm of Smith & Same, located in Anywhere, New Zealand, works closely with his younger partner Sue. Recently, Phil sent me an unexpected email. It was unexpected (if not startling) because he presents as a relaxed, genial and unflappable person who remains calm in the eye of the storm.

The email read:

“Emily: Am confronted with a very challenging and upsetting personnel issue – at my wits end. Please call me as soon as possible. Phil”

When I reached Phil, he said: “Sue, as you know, is the partner with whom I have worked most closely and whom I hope will ultimately take over my practice. Last week, she really let me down with a client, both technically and in terms of her professional integrity. I haven’t told her this, but I need to do something about it soon. Either we can turn this around or the implications are really concerning. What shall I do?”

I said: “Phil, you need to have a difficult conversation with Sue and give her some feedback about what happened. You have one chance to do it right the first time. Let’s talk about how to do that.”

Here’s what we discussed.

The difficult conversation 

The ability to give, receive and digest feedback is a critical capability for lawyers. 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 master how to do this, 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.

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?

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 behaviour 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 the two of you 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

This should include:

  • 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. Among 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.

Being on ‘the other side’ of a difficult conversation

If you are the recipient of feedback, 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 judgement 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 as 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.


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.

Very receptive

Phil used the above structure as “roadmap” for his difficult feedback conversation with Sue. She was not entirely surprised when he initiated the conversation (having sensed that something was “wrong”), and was very receptive to considering how she might have handled the situation differently.

They used their discussion as an opportunity to bring their client management approaches into better alignment. Although this was not an easy conversation, Sue and Phil are to be commended for having used it as an opportunity to enhance their working relationship.

Difficult though the conversation was, they have no regrets about having engaged in it.

Emily Morrow 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. She can be reached at

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