A Guide to Difficult Conversations

It’s Friday morning. Everyone else in the office is finishing up projects, filling out timesheets, planning a lunch with coworkers, and looking forward to the weekend. But not you. No, you are anxious and worrisome, staring at the appointment on your calendar scheduled for 2 PM – you’ve got a tough conversation coming up.

Maybe you’re in a management role and you have plans to discipline or even fire an employee. Perhaps you had a disagreement with a coworker and need to squash it. Or maybe you’ve had a tough quarter and have a one-on-one with your boss that you know will be difficult. Tough conversations are part of the workplace and everyday life. Though they are uncomfortable, speaking your mind and communicating needs to others can be incredibly valuable.

So, in order to bust through the anxiety that accompanies these conversations, it’s a good idea to prepare accordingly. Here are some examples of common tough conversations and some great ways to keep the chat on track.


Examples of Tough Conversations 

Tough conversations can come in many forms, especially in the workplace. While conversations should be a two-way street, with both or all parties having the chance to be heard, most discussions will be fairly direct. For example, you might be discussing:


  • Poor overall job performance
  • Issues on a specific project
  • HR issues, such as attendance or workplace ethics
  • Interpersonal issues
  • Disciplinary action, like suspensions or probation
  • Employment termination


Just looking over that list is enough to give anyone a sense of mild panic. However, when you know these discussions are on the horizon, there are some excellent ways to prepare.


Tips for Tough Conversations

At work, it’s rare to be truly blindsided by tough convos. Sure, being fired abruptly does happen, or you may have offended someone in a workplace dispute without even realizing it. But generally, you’ll be able to prepare for the upcoming talk whether you scheduled it or were invited to the conversation.


  1. Identify Your Objective


What do you want to accomplish with this discussion? Are you looking for someone else to take responsibility for their words or actions? Do you want to see a specific behavior change? Do you need to let someone go? Whatever your goal, these talks are best if they’re kept short and sweet, and guided toward a single point. Otherwise, it’s likely to turn into a back-and-forth argument


  1. Plan Ahead


Scheduling a conversation is far superior to surprising someone with a tense discussion in the middle of the workday.You can speak to them about it, but their curiosity or anxiety may lead to questions, and therefore lead you to having the discussion right at that moment. Send an email invite with a brief description. Not only will this help to nail down a time, it also creates documentation in case management or HR needs it for later uses. This also ties back to the idea of identifying an objective, as some conversations like firing someone should happen later in the week, and others such as one-on-ones are better suited for Mondays so that the recipient can apply the feedback to their work immediately.


  1. Center Your Emotions


There’s no space in effective conversations for yelling, crying, or otherwise emotional expressions. You’re already going up against another party who will likely want to argue or at least express their rebuttals. Before beginning a conversation, check in on your emotions and keep them from entering the dialogue. Now, that doesn’t mean speak to them like a robot; empathy and kindness can go a long way, especially when you’re trying to convince someone of a change. However, be aware that these feelings can also make you susceptible to manipulation.


  1. Speak Clearly and Concisely


“I don’t quite know how to say this, so I think I will just drag it out…since the dawn of time…” – Michael Scott


During the conversation, it’s important that you don’t mince words. Unlike Michael Scott in the above quote, get right to the point. Though the topic might be delicate and you feel as though it deserves a wind-up, you’ve already scheduled the conversation. This means everyone involved has been agonizing over the discussion, and a straightforward manner will be much more appreciated. Additionally, when we start to ramble on or let conversations go longer than needed, it’s more likely we will backtrack or start to negotiate with ourselves. Say what you mean in as few words as needed, and then let the other person speak or be comfortable in the silence.


Make the Most of Difficult Conversations

They say the devil is in the details. While this adage might cast a negative light on difficult conversations, the truth is that preparing for these discussions is essential to making them productive. By taking time to consider your objectives and centering yourself emotionally, you ensure that chats will accomplish goals, not become a fight or argument.



A Mindset of Abundance

In this episode, Desiree and Chrissy take a deep dive into mental health and the importance of positive thoughts while chatting with brain researcher and therapist Phyllis Ginsberg. This touches on anxiety, depression, EFT tapping, and positive psychology. If you’re looking to take a step toward thinking of what’s possible, this is number one.

Phyllis Ginsberg is known and beloved by lots of happier, healthier, and less stressed working professionals as their Survival to Thrival Expert. She’s the author of two books:Brain Makeover – A Weekly Guide to a Happier, Healthier, and More Abundant Life,” andTired and Hungry No More – Not Your Ordinary Guide to Reclaiming Your Health and Happiness.” Her 30 years of experience as a marriage and family therapist, and expertise in positive psychology, brain research, and EFT tapping, give her clients an edge in making lasting, profound changes in their lives. Quickly, they shift their stressful thinking to achieve calm, clarity, and creativity. That means that the quality of their lives and work gets better – often in a moment. 

External Links:

Connect with Phyllis Ginsberg


FREE GUIDE: Cope with Stress and Overwhelm in 5 Minutes or Less

Cultivating Investor Relationships

You’ve got one shot to land an investor for your business; can you do it? Brian Folmer can and his startup FirstLook is thriving, even after launching just two days before COVID-19 shut down New York City. Brian teaches us about drafting your pitch to building a buzz to growing your business enough to be able to say ‘no’ to new customers.
Brian is a two-time founder who currently leads FirstLook, a subscription box full of emerging, high growth consumer brands for early-stage investors. Before FirstLook, he led BD & Strategic Partnerships at XRC Labs, International Operations at Victoria’s Secret, and founded a previous startup through a startup technology accelerator in Cleveland. Brian joined AKPsi while attending The Ohio State University. Today you can find him at the WeWork Consumer Labs in NYC. 

External links:  

Board of Directors 2020 Update

During the weekend of August 7th and 8th the Fraternity and Foundation Boards convened via Zoom for the first ever all virtual board meeting. The weekend-long meeting included a Voting Members session to discuss changes to the Fraternity based on the effects of the Coronavirus and the election of directors.

Alpha Kappa Psi is proud to announce the Fraternity Board of Directors for the 2020-21 year:

Eileen L. Howell, Wisconsin-Milwaukee ’78-Life

Vice Chair
Chrissy M. Vasquez, Arizona State ’98-Life

Naneen Christopher, Seton Hall ’05-Life

Micheal E. Dickson, Central Washington ’02-Life

John M. Levering, Boise State ’95-Life
Debora E. Barrett, Montclair State ’98-Life
Miriam V. Tomaselli, Marist ’97-Life
Michael G. Dickerson, CFV, Virginia Tech ‘04-Life

Donald T. Sechler, Arizona State ’96-Life


Director – Emeritus
Ken B. Hastey, Saint Louis ’76-Life                                                                                        

Thank you to Nancy Huebner, Richard Battle, and Alexander Sultan for their time on the Board.  The terms for serving on the board ended for Brothers Huebner and Battle 8/8/2020, and Brother Sultan resigned his position on August 8, 2020.  Don Sechler was officially appointed to the Board to full the vacancy left by Sultan.

Alpha Kappa Psi is proud to announce the Foundation Board of Directors for the 2020-21 year:

Eliza J. Hernandez, North Carolina – Charlotte ’09-Life

Vice Chair
Timothy W. Daniels, Indiana ’06-Life

Lisa A. Calandriello, American ’97-Life

Stephen E. Smith, Florida ’86-Life

Jeff E. Frank, Eastern Michigan ’86-Life
Rodney C. Turner, Alabama State ’93-Life
Joshua Boddiford, South Florida ’00Life                                                                                                                                                                                                                                                                                Mat D. Johnston, Boise State ’12-Life
Lea S. Goodwin, Louisiana State ’99-Life

We want to thank Manuel E. Pravia and W. Frederick Thompson for their time on the Board as their terms ended on 8/7/2020.


Additionally, the Board of Directors voted on the Area VPs for 2020-21:

Area I – Maya S. Richardson, Arizona State ‘12
Area II – Jonathon T. Pritt, Marshall ’11-Life
Area III – Andrea Nemeth, Montclair State ’91-Life
Area IV – Stephanie N. Potter, Auburn ’00-Life

We want to thank Stephanie Van Dellen for her service to the Management Team as her term as VP Area I ended 8/8/20.






Entrepreneurship: Soul Carrier

The Devil Wears Prada comes to life in this episode with Jennifer Boonlorn, creator of Soul Carrier, a line of luxury handbags and accessories. Jennifer tells us an amazing story of family heartbreak leading to business inspiration as she travels from Arizona to New York City to find her true north. A special discount code is available for our listeners at the end of the episode!

Soul Carrier was founded in 2011 by designer Jennifer Boonlorn. Raised in Phoenix, Arizona, Jennifer graduated from Arizona State University with a degree in business with the goal of becoming a lawyer. After losing both of her parents in a family car accident when she was a senior in college, she found it imperative to re-think her future path. Jennifer relocated to New York City to pursue a career in the fashion industry. 

External Links:

Connect with Jennifer Boonlorn

Soul Carrier website