New Zealand Law Society - Making difficult conversations less difficult

Making difficult conversations less difficult

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Difficult conversations are inevitable. If you are in a position of responsibility in your firm you must be prepared to deal with them effectively.

Yet, at the recent NZLS CLE Stepping Up course in Auckland, a number of people, some with significant lawyering experience, said that as a manager they felt woefully underprepared and, indeed, scared of dealing with these challenging one-to-one collegial conversations.

What is a difficult conversation?

These are often where we have to deal with emotional or sensitive information (or both) to:

  • address poor performance;
  • investigate professional or personal misconduct;
  • mediate employee clashes;
  • navigate employment issues like restructuring or redundancies; or
  • discuss health concerns.

Understanding when to delve deeper into these conversation to seek clarification or extract additional knowledge concerning a situation and, of equal importance, knowing when not to, is often only learned through experience.

Most problems that arise in the workplace already have clearly defined consequences. So being in control of yourself is often the key to mastering successful outcomes to these difficult one-on-one interactions.

Invariably, this means being well prepared. This helps focus these challenging conversations on the specifics of the problem and enables better retention possibilities for those all-important professional relationships no matter what the outcome.

The following are some management strategies that may help keep you in control.

Create a culture of openness

Mitigating risk is a familiar concept to lawyers, but do you practise this in relation to your business leadership?

To lessen the impact of challenging conversations when they occur, invest time in regularly visiting your employees.

Make a point of being visible. Take time to ask people how they are and listen. They will be more likely to be open with you when something goes wrong if you present yourself as available and interested in them.

Utilise a staff representative to communicate issues to you. Take action when things are brought to light. Let people know you’ve listened to their problems and questions, even if the answer is no.

Offer opportunity. When you are first aware of a situation, let the individual know and offer your immediate support. Done in a quiet informal manner, these one-on-one interactions can often negate future iterations of the problem.

When a difficult conversation is needed, communication is the key. Let the individual know what the meeting is about and that your intention is to facilitate an agreed outcome. Make a time and stick to it.

Be timely

As a busy practitioner, often the temptation is to postpone those things in the managerial “too hard basket”.

While it is essential that we invest in becoming au fait with the specifics of the issue and having “time out” to consider your thoughts is often invaluable, delay in dealing with an issue runs the very real risks of:

  • reducing the window of opportunity for improving the problem;
  • having the issue escalate or embed itself;
  • damaging your team ethos; or
  • misleading the individual to the existence or importance of the problem

And, when the issue comes to light, it will make you look unprofessional. When you finally do organise your meeting, follow it through.

Be supported

Ensure that another, preferably a senior partner, is aware of the issue and your plan to deal with it. Seek the support of a local colleague if you feel this is the best way of avoiding conflicts of interest or if you are in a very small practice. Protecting yourself is important.

Be informed

Purposely take time to collate and analyse the issues before the meeting.

Strive to link this information back to the individual’s role and the identified problem. Focusing on the behaviours and not the person also helps combat those tricky “out of office” encounters, especially important in practices belonging to small or rural communities.

Things like key performance indicators, job descriptions, manager’s diary notes, objective data, times, dates and recorded activities will help keep the emotions at bay. Often, after analysing the data, you may have identified opportunities to improve the situation. If so, you’ll no longer be giving negative feedback but be leading a constructive conversation about addressing the problem. Regardless of such, if you are possession of the facts then you can remain on topic.

These specifics are important as in many employee conversations there is a risk of going off on a tangent. These often become emotive and personal in nature and become a distraction to the pertinent issue. It can help to jot down key points beforehand, to keep the conversation focused but don’t rely on these – you need to be in a position to maintain eye contact and listen.

Sharing with the individual how the discussion will be structured and agreeing on standards of behaviour will set the tone for the conversation, give direction and help keep you calm.

Be calm

Being aware of how you feel before the conversation is essential. You are in charge and must act like it. Being calm and in control of your emotions will help facilitate a positive outcome.

Avoid meeting times that are after lunch or in the late afternoon when you may be tired or have the potential to be disturbed. Equally, invest some time thinking about if the shoe was on the other foot. How would you feel or react? Is there something else about the individual or their personal situation that you ought to be cognisant of before the meeting? You should be prepared for their emotional reactions. How will you deal with this?

Think about how you are going to conduct the discussion. Open, relaxed, body language while sitting side-on next to the person is often less threatening than from behind a desk. However, with a follow up meeting, where an issue has continued or where a serious matter needs addressing, the latter may be more appropriate.

Choose your words carefully. Take time in your responses to questions and ensure you are deliberately slow in your response. Adopting a slow, low voice is a good technique to help you and the other person stay calm. Be the consummate professional and avoid reacting to aggressive, malicious or overly cynical responses.

Asking the right type of questions can also aid in a quick resolution. Generally, it is more beneficial to use open-ended questions at the start of your conversation, following up with more closed-type questions to confirm and probe on the details of the discussion.

Difficult conversations must not be rushed. In the initial stages of the conversation, try and unpack the other person’s point of view by asking them what they think the problem is first.

Focus on causes of the problem rather than the outcomes. You fix the cause, you fix the outcome. Use this as your opportunity to then outline the practice’s view of the problem. If you aren’t sure what is causing the identified problem, acknowledge that you don’t know. Importantly, focus on providing potential solutions. You take the lead.

Above all else, demonstrate you are listening. Making eye contact, nodding and smiling, reiterating the individual’s facts and point of view, or asking clarifying questions is a good way of doing this.

Be courageous

Whatever happens, take the lead in delivering the tough news in a courageous, honest way. This part of the conversation will be based on the conversation and your collated evidence. Don’t play victim. The worst thing you can do is to ask for sympathy by saying things like “I feel terrible but” or “this is hard for me to do.”

If the meeting uncovers new information, or if things get heated, don’t be afraid to abandon the meeting. This will be beneficial for all parties involved in the long run.

When the meeting is over and if you have arranged certain steps for improvement to be taken, personally follow this up. Do not delegate this task out in the first instance. You then remain connected to the individual and your agreed next steps to improvement.

If the meeting resolved the issue, then it is resolved. You must demonstrate in action and words that this is so.

The outcomes of these conversations will not always be positive but the manner in which they are approached can be and this is your responsibility as a leader.

Planning questions

A summary of planning questions for facilitating successful conversations is:

  • Have I identified the issue?
  • Have I got my facts straight, what is my objective evidence?
  • Have I reflected on the potential/actual cause?
  • Have I considered other things about the individual that are important?
  • Do I need support?
  • Do I know my policies and procedures? Performance management, health and wellbeing, cyber-usage, conflict, discipline and grievances.
  • Do I have some solutions in mind?
  • Am I open to other solutions?
  • Have I communicated a clear plan of the meeting?
  • Is there a safe private space available?
  • I have I communicated confidentiality (if appropriate?)
  • Have I thought about my questions?
  • How will I use non-emotive language?
  • Have I set aside enough time for the meeting, and after the meeting to gather thoughts and record notes?


Ken Trass is the New Zealand Law Society’s Professional Development Manager.

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