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6 Ways to Master the Art of Difficult Conversations

ByMelissa Zehner, Last Modified
Jul 05, 2019
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> Career

Difficult conversations are part and parcel of leadership. When these talks go well, they can improve rapport, engagement and output. When they go poorly, though, they can derail relationships, projects and even entire teams.

You can improve the outcomes of your difficult conversations by:

  • Reinforcing trust and transparency
  • Offering your undivided attention and a listening ear
  • Helping your counterpart feel heard and respected
  • Apologizing or taking a break when called for

Here are six ways to artfully navigate even the toughest discussions. 

1. Make meetings a safe place

Long before it's time to have a difficult conversation, you should cultivate a culture of respect, inclusivity and transparency. Create an environment in which each team member feels valued, encouraged to participate and rewarded for candor. 

To start building this foundation, offer opportunities for collaboration and idea sharing. Invite team members to share ideas and seek feedback. Be sure to ask open-ended questions, which prompt deeper participation than yes-or-no questions. It's also a good idea to schedule group lunches or other non-work activities that give everyone an opportunity to socialize and find common interests outside their job descriptions. 

Fostering these dynamics builds trust and camaraderie, which lay the groundwork for a more constructive outcome, no matter how difficult the conversation. Feedback is received better when we believe it's being offered out of concern rather than judgment. 

It’s also helpful for both parties to remember that you're ultimately on the same team. Executive coach and management professor Monique Valcour recommends sitting next to, rather than across from, your counterpart. This placement reinforces the idea that you're allies rather than opponents, setting the stage for a more cooperative conversation. 

2. Put your phone away

Better yet, don't bring your phone to the meeting. Leave it elsewhere. Having your smartphone nearby impairs cognitive capacity, including short-term working memory. 

A small Virginia Tech study also found that the mere presence of a cell phone was enough to undermine participants' perceptions of their conversations. Even when the phone was placed on a table and left untouched, participants rated interactions as less fulfilling and reported less "empathetic concern." This outcome applied whether the discussion topic was considered frivolous or meaningful. 

Researchers from both studies recommend setting up your conversation for success by leaving your phone in another room or a desk drawer or, better yet, your car. 

Don't use your phone to have a difficult conversation either. Even the most eloquent email or text message is no match for a thoughtful in-person conversation. Emojis will never replace the nuanced messages we get from eye contact and body language. Plus, if you're conversing over your phone, there's a strong chance that you're multitasking while doing it, which means you're not giving the conversation the undivided attention it merits. 

3. Listen more than you talk

You're probably familiar with the adage popularized by Stephen Covey, "Seek first to understand, then to be understood." 

Rather than rushing to get your point across before giving your counterpart a chance to speak, Covey's method advises the opposite. If you start by asking questions and listening sincerely, you have the opportunity to learn more about the person you're speaking with and the issue you're addressing. By the time it's your turn to talk, you're able to do so with more empathy and understanding. This approach also helps your counterpart to feel heard. 

You can put this tip into action by simply starting the difficult conversation with questions rather than statements. For example, rather than kicking off with a statement like "I'm disappointed you missed another deadline," try asking, "How do you feel about your project timelines? Are you facing any challenges?" 

Resist the urge to interject as your counterpart talks or fill the silence if there's a long pause. The more you listen attentively, the more your counterpart is likely to say. This can give you more insight into how to deal with the challenge at hand.

4. Be clear

While you don't want to be tactless, avoid the temptation to sugarcoat your feedback. You'll be doing yourself and your counterpart a disservice by downplaying the problem at hand. It's also unreasonable to expect a marked improvement if you’re not frank about the negative impact of your counterpart's behaviors. 

To make your feedback as constructive as possible, it should include: 

  • Tangible examples of the behavior you’d like to change and what you'd like to see instead 
  • Specific actions that can be taken to improve performance
  • A timeframe for when you'd like to see improvement
  • Confirmation from your counterpart that he or she understands what’s expected

And don't forget to follow up after the initial conversation to talk about the progress that's been made. If you see improvements, take a moment to thank your counterpart or offer congratulations on a job well done. Positive reinforcement is crucial for transforming new behaviors into sustainable habits.

5. Apologize 

The adage that the boss is never wrong is, in fact, just plain wrong. We all make plenty of mistakes. Being a leader doesn't change that. And when the stakes are higher, our errors are often magnified. 

If you've messed up, acknowledge your misstep and apologize. Remember, you're not just making amends, you're also modeling the behavior you'd like your team to emulate: admitting mistakes, taking ownership, setting aside ego and committing to do better.

Your apology doesn't need to be fancy, but it does need to be genuine. Apologize humbly and thoughtfully, then make a sincere effort to avoid repeating the mistake. 

Don't let that unaired apology linger too long, though. Waiting can breed uncertainty, anger, or resentment, which can make an already difficult conversation that much more arduous.

6. Hit the pause button

Never, ever broach a difficult conversation when you're feeling emotional or angry. If you need time to cool off, take it. Wait until you are able to approach the talk rationally and calmly so your behavior is constructive rather than combative. Addressing problems in the heat of the moment typically just makes them worse, not better. 

If you need to, apply this same advice to a conversation that's already commenced. We often feel pressed to finish a conversation once it's started, but pushing through isn't always the best course of action. If you or your counterpart are becoming overwhelmed or emotional, take a break. Pausing gives you both time to regain composure, organize your thoughts, and get a handle on your emotions so you can approach the conversation more constructively.

Try saying, "We've both learned a lot so far today. Let's take a little time to digest everything we've talked about and revisit this conversation tomorrow." Then be sure to follow up and schedule another meeting so you both know when the conversation will take place.

You can also prepare for the meeting by taking a few practice runs and practicing what you're going to say. Rehearsing helps you get more comfortable with the idea of talking about challenging topics and gain confidence in your ability to reach resolutions.

It's normal to feel apprehensive about a difficult conversation, but having the talk is always better than avoiding it. You won't resolve a problem unless you address it with clarity and thoughtfulness. 

Remember, a difficult conversation is ultimately about making improvements and building relationships. Don't let the discomfort distract you from your goal: leading a successful team and running a successful business. 

Melissa Zehner
Melissa Zehner
See Melissa Zehner's Profile
Melissa Zehner is a Small Business Finance Editor at Lendio, the nation’s largest business lending marketplace. In addition to reporting on business finance trends, she studies the intersection of culture and business to find compelling stories about everything from grassroots movements to game-changing tech to government policy.
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