Five Difficult Workplace Conversations for Leaders & HR

Difficult conversations with employees

Kids have it easy. If something doesn’t look right, smell right or seem right, kids don’t hesitate to state the obvious.  They don’t worry about hurting someone’s feelings.  They just say it.  I’ll never forget the time I was playing with my six-month-old daughter when a boy asked me when I my other baby was going to be born.  Ouch, that stung.  That kid didn’t worry about my feelings.  He didn’t know he needed to and just spoke as he saw things in the world.

Five Difficult Workplace Conversations for Leaders & HR

Sometimes I wish the world of Human Resources and managing your employees were as easy as it is from the mouths of babes.  Difficult conversations with employees rank up there in the list of things no one wants to do and are not far after public speaking or death.  As managers and HR leaders we deal with wacky stuff like sex at work, random poop smearers in the men’s bathroom, and phone interviews where the candidates is taking all bath.  I’m not kidding.  Things like these are common place when you are the boss lady or man.  As managers though, we have some common yet candid difficult conversations we just have to have.  Some make for great stories and others break your heart.

Top 5 Candid Conversations Manager & HR Professionals Don’t Want to Have with You

· POOR HYGEINE:  You have a Mo.  Mustaches aren’t a big deal in most work environments.  Even the deli-counter guy can sport a crumb catcher or a full, mountain-man beard with a facial-hair net.  But… what if you’re a woman?  Dealing with female facial hair in the office ranks up there with B.O. (aka Body Oder) or even bad breath.  Hygiene issues rank as one of the most difficult type of conversations to have and there are legal aspects to consider.  My least favorite was having the bra conversation with an employee at work.  Sometimes an underlying medical condition could be the culprit and as an workplace leader it is your job to address the employee.   When dealing with a hairy or stinky situation, remember to be candid, sensitive, supportive, considerate and understanding.

· FIRST TERMINATION: You’ll never forget your first time.  Mine was especially close to home.  This is especially true when it comes to termination.  HR or otherwise, there comes a time in almost every manager’s career when you have to give the ax.  A termination should never really be a surprise to the employee.  Constant feedback and a clear understanding of consequences should provide them insight to their performance… and that the end road at this company has a high probability.  According to, managers should talk with HR before initiating the termination process.  As the HR professional, it’s your job to ensure the ducks are in a row and to guide the process, but in most cases it’s not my job as HR to be the one to terminate the employee.  Role playing how the meeting will go and what points should be made are helpful as you navigate your first termination.  During the meeting, it is important is to empathize with their situation and be professional.

· LAYOFF ANNOUNCEMENT:  This one might also bring the Public Relations team into play depending on the media backlash.  It’s important not to sit on this announcement because no matter how tight-lipped you think this is, it isn’t. The reality is, that even in a sound proof room, the information in some form or other has gotten out and the rumor mill is churning before you open the door.  Be direct.  Be honest.  And don’t sugar coat.  It’s best to take ownership of the announcement.  Don’t say it is someone else decision.  As a representative of the company, it’s your job to accept the role as the messenger, and it is best to deliver such a message in person versus over the phone.  Email is a last resort of communication.  Follow up all conversations with a formal memo or letter to ensure the communication was clear and understood.

· LIFE & DEATH:  Sharing news can be a perk of the job for an HR Manager.  Except when it’s hard to deliver news.  I recall hearing a story from a printing plant whereas gentlemen called the customer service line and asked for a specific floor supervisor.  It was an unusual request, but he told the employee it was urgent.  The customer service rep knew the supervisor and ran out and retrieved her.  Little did either of them know the urgent news was that the floor supervisor’s husband had suffered a sudden heart attack and died.  It was a difficult situation for everyone involved.  Dealing with difficult news in the workplace is one of the most challenging parts of being a manager.  If the death is an employee, then it might be the HR manager’s role to communicate the death to all staff.  Sometimes, bringing in experts can help HR provide the extra counseling and support needed to get through such a crisis, especially if HR is among those deeply impacted by a loss.

· WORKPLACE INVESTIGATIONS:  As if doing your job wasn’t difficult enough, now there is an investigation into an employee’s behavior – excuse me – alleged behavior.  Depending on the nature of the complaint, this one could quickly escalate to bringing in a legal team or your friends in public relations again.  Dealing with investigations, whether it is fraud or embezzlement claims or allegations of improper relations, it is important to document all conversations and request legal counsel for your protection and your company’s.  A conversation about a workplace conversation can halt everything you are working on and turn your HR World upside down.

Work is Tough.  Being a Manager is a Rewarding & Hard Job

Having difficult conversations is a part of the Manager and HR’s job.  Dealing with the unexpected is especially tough.  But, anxiety can weigh heavy when rehearsing for planned conversations such as with body odor or a termination.  Reviewing best practices before situations arise can help the HR Manager navigate these challenges and emerge a stronger leader.

This post was originally published on’s blog where I’m a regular contributor.  Check it out by clicking here.  

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Jessica Miller-Merrell

Jessica Miller-Merrell is the founder of Workology, a digital resource that reaches more than a half million HR and workplace leaders each month and host of the Workology Podcast. Jessica lives in Austin, TX, with her husband, daughter, and an assortment of furry family members.


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