5 Things To Do To Prepare For a Difficult Conversation

When I was twenty-four years old I had the privilege and burden of supervising staff in a department of a large HIV/AIDS organization. I was a co-director for social services where I had responsibilities for oversight of client services, individual and group counseling, food pantry program, weekly dinner for clients, and housing advocacy. In many ways this was a dream job: I was able to provide material needs with dignity to people who did not regularly receive that level of service and I had responsibility and enough autonomy to implement programming that was client-centered; and most of all the job was a learning curve on every level, every day.

The burden of the job was having to supervise people, when I had little management experience and no support as to how to do this. As a leadership coach, I work with my clients now on management, so I can look back, mostly fondly (and sometimes with cringes), at the stumbling I had to go through to get things done. In my job at the HIV/AIDS organization, I had to supervise a staff where everyone was older than me. The age range of the five people I had to supervise went from twenty-eight to forty. As you can imagine I encountered a lot of ageism that I had to pile on top of my race and gender - fun times!

Anyway, this period was full of my having to have difficult conversations at work, and I want to share some lessons I have learned from this experience and subsequent ones, to help you develop your leadership and be able to better communicate with your colleagues.


5 Things To Do To Prepare For a Difficult Conversation

  1. Address the person in a timely manner. Are you holding back on saying something to someone in your life? Do not let an offence, missed deadline, or insult sit and fester. The longer you sit with something and stew over what happened, the bigger the problem becomes in your mind. Take a moment and review what it is that happened that upset you, determine whether or not you can let this go - and if you can, do so; if you cannot, plan to address the person. Remember, the longer you put off the conversation the worse it gets. You forget the details and end up relying mostly on your feelings. Which leads to the next point.

  2. Just the facts, please. Once you decided to address the person, make sure you are describing the situation and not making judgments. Judging people can be fun when we do it with our friends, but it is never helpful when you want someone to really hear you. Saying, “I would like to discuss last Tuesday’s meeting, when you interrupted me twice,” is a better approach than “you really disrespected me the other day.” Also, vague language is never helpful. You need to paint a clear picture for someone to understand you.

  3. Prepare and Practice. Very few people want to have difficult conversations. Many of us would rather sit in our own pain than have to confront someone on how their behavior impacted us. In my job example above, one of the staff people I was supervising, a woman in her mid-thirties, interrupted me while I was presenting to a group of external colleagues from other organizations, to highlight my age and remark “how do you know that, you weren’t even born yet.” I remember I kept my composure enough to finish what I was saying but I was fuming. And of course that comment hit my sensitivities and vulnerability around whether I was indeed prepared to be in this leadership position. I had to give myself time to calm down, center myself in my worth and confidence, and then I wrote down what I wanted to say and kept saying it over and over until I could say it without crying.

  4. Give a heads up that you want to talk. Never blindside someone with a difficult conversation. Let someone know, “I would like to talk to you later today about what happened in yesterday’s meeting.” The person you are talking to also needs mental space to prepare and you will have a better chance of being heard and hearing someone else’s perspective if you do not corner and confront them out of the blue.

  5. Have a resolution. Even if it is that you want the other person to hear how you experienced what happened. Offer a solution if possible. If you do not have a solution, offer an opportunity to discover a solution together. Also, be open to hear what the other person has to say that may offer insight to your own perspective.


I hope these tips are helpful. If you are avoiding having a difficult conversation, think about what is it costing you - how difficult is it - not to have that conversation. What is it costing you not to talk about what is wrong: are you losing sleep, are you experiencing anxiety, are you unhappy, are you thinking about leaving your job? Weigh what you are willing to suffer versus the alternative of pushing yourself to reach a better understanding with your co-workers.

I would love to hear from you: Are you holding off having a difficult conversation, if so, why?; or, What has been your experience with difficult conversations with colleagues?



Patricia Jerido is a coach for Leadership Matters Consulting where she uses mindfulness practice to bring about social justice change. Find out more at www.leadershipmattersconsulting.com or follow @CulturalMusings



Patricia Jerido