Handling Difficult Conversations at Work

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If you work in management, you live in the land of difficult conversations. Whether you’re instigating or hearing about them, difficult conversations are central to your world. Unfortunately, that doesn’t make these conversations any easier. Difficult conversations are always difficult, hence the label. Confronting challenges, giving critical feedback, dealing with differences of opinion, and enforcing rules or policies when they’ve been violated is a fact of work life for managers and HR personnel.

Most workplaces bring together a diverse group of people with vastly different backgrounds, skills, ages, attitudes, and personalities to work toward a common cause. From time to time, they have to discuss issues they’d rather avoid. Nonetheless, there are numerous benefits to having successful difficult conversations with your team: better relationships, better problem solving, and better resilience.

In a recent article, Eileen Habelow, longtime HR professional and president of Leadership-Link, a Boston-based consulting firm, told the Society of Human Resources Management, “If your goal is to get the most out of people, then you have to be willing to give direct, difficult feedback. It’s not a bad thing. You’re doing them a service.”

With that in mind, here are a few things you can do to make those difficult conversations less onerous.

1. Use Discretion
Pick your battles. Don’t squander your energy and reputation by sweating the small stuff. There’s plenty of big stuff to go around. Consider what truly requires your attention, what kind of conversation the situation calls for, and plan accordingly.

For instance, it’s nearly impossible to be an effective employee when you’re on the outs with your boss. Significant differences of opinion that hit on divergent values, if left unresolved, can have a detrimental effect on relationships, and by extension, the work being done. Whenever possible, it’s much better to talk out larger challenges, even when it’s hard. Of course, the issue at hand could have nothing to do with your boss. Maybe a peer is sabotaging your authority by routinely and rudely cutting you off in meetings or by dismissing your ideas with palpable scorn. Either way, avoiding difficult conversations about serious issues like these can have a detrimental effect on the workplace as a whole, not to mention affect the quality of work and working relationships of those involved.

Staff issues—such as poor performance, underperformance, tardiness, incivility, and the like—warrant timely, honest, and compassionate communication. Some infractions, such as occasional lateness or unscheduled absences, may not require the most serious of sit-downs, but bullying and significant poor performance certainly will. When in doubt, be sure to consult your own manager or human resources personnel for additional guidance and support.

2. Be Prepared
Don’t try to have a difficult conversation without being prepared. A tough talk deserves prep time on the front end. Be mindful about what outcome you need and stay focused on that. Be clear about your expectations and goals. Also, think ahead about the steps you’ll take to keep your emotions in check and the dialogue on track.

3. Keep Your Eye on the Forest (not on the Trees)
When feelings control the conversation, difficult conversations can quickly go south and lose focus. Make sure you keep yours in check, even if the other person does not. Take time to separate the facts from your feelings and assumptions about the situation before you sit down. Focus on tangibles: What specific outcome are you seeking? What needs to be communicated to achieve that outcome? Make a conscious effort to keep your ego in check and say only enough to state your intended message with calm clarity, understanding that a certain level of detachment is appropriate. A difficult conversation shouldn’t be mistaken for an opportunity to make a new bestie, after all, and you’re under no obligation to reveal your deepest thoughts. Keep it honest, yes, but most importantly, keep it professional and relevant.

4. Remember to Be Human
A little self-effacing humor can go a long way toward gaining trust and goodwill. Allow yourself to be vulnerable, and you may be surprised at the result. Acknowledging the challenging nature of your discussion may set the other person at ease by revealing how nervous you get before having difficult conversations, thus affording you the opportunity to show your shared humanity. Play it by ear and be genuine.

5. Save Everyone’s Face
Nobody likes being backed into a corner, especially during a difficult conversation. No matter how “right” you are or how “wrong” the other party may be, do both of you a favor and provide a way for everyone to save face. Be a good listener, agree when you can, and make a point of assuming good intentions.

6. Have an Out
Have a plan for how to extricate yourself with calm professionalism if the conversation gets too heated to be productive. It’s okay to call a time-out and put the conversation on hold until a later date. Better that than crossing a boundary or saying something that compromises you or your company. If seeing eye to eye is impossible, there’s no shame in agreeing to disagree. Taking time to clear the air is one step in the process of learning whether a  person is an appropriate fit for your team, while also offering the chance to create healthy boundaries and workplace dynamics.

Crystal Spraggins, SPHR, SHRM-SCP is an HR professional and freelance writer born, bred, and living in Philadelphia, PA. Crystal has more than 20 years of experience as an HR leader helping small- to mid-sized for-profit and nonprofit companies develop policies, programs, and procedures that increase profits, maximize efficiency, and enhance positive employee relations.


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