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How to have a difficult conversation with a team member or customer

It’s one of the most challenging aspects of leadership: How do you effectively have a difficult conversation with a team member or customer?

The answer: With sensitivity and respect.

Difficult conversations should never be taken lightly, especially in the current climate of heightened emotions.

Executives, managers, and entrepreneurs all know they need to have tough talks with their employees from time to time — but that doesn’t mean it gets any easier. In fact, it might be harder now because of a heightened tension between different ideologies that have spilled over into workplaces everywhere — combined with the fact that there are more generations in the workforce now than at any time in history.

“One thing we can’t escape is that this (time) has been very divisive for many Americans,” said Bill Hybels, senior pastor at Willow Creek Community Church near Chicago. His church draws more than 25,000 attendees each weekend from across the country and around the world. Difficult conversations consumed two days of training during Willow Creek’s annual Global Leadership Summit earlier this month.

“I’ve seen the level of anger escalate at an alarming rate,” Hybels said, “and I’ve seen the level of outrage rise exponentially.”

This is not just a problem for business leaders.

School teachers, college professors, church pastors, non-profit directors — anyone in any position of leadership or authority — could find themselves having these difficult discussions with employees or customers who may be upset over changes that affect their families.

Difficult conversations arise frequently and at all levels, and they should be handled with respect and for the good of everyone involved — even those who may disagree.

  • Difficult conversations happen whenever we hold accountability sessions, give performance reviews, address challenges with an employee’s attitude or behaviors, challenge a viewpoint that someone holds dear to them, or when we deliver difficult feedback.
  • Difficult moments often come up when people feel stressed by their circumstances and about making hard choices about where scarce resources will be distributed.
  • Difficult conversations also arise during routine day-to-day interactions such as meeting deadlines and resolving workplace disputes.

While these conversations aren’t easy (that’s why they’re called “difficult,” isn’t it?), here are three basic steps to handling these uncomfortable situations:

1. Prepare yourself

  • Remember why you’re having the conversation
    • When difficult conversations come up, it’s easy to lose sight of what you want to achieve in that conversation. Your goal is not necessarily to change your team member’s mind or get them to agree with you, but just ensure they understand where you’re coming from and why this matters so much to you. You may even be able to find some common ground on which both parties can meet.
  • Acknowledge their feelings
    • The #1 reason many people resist giving constructive feedback is because they don’t know how the other person will feel about it. When we fear upsetting someone — especially someone whom we care deeply about — our natural response is often to avoid it. Difficult conversations are never easy, but the more you can do to put people at ease, the better your chances of having a productive conversation.
  • Be respectful of their time and priorities
    • Everyone has responsibilities that take some precedence over work–with kids or parents who need help, problems at home that need solving, commitments to attend religious services, not to mention taking a lunch break! Difficult conversations might cut into time they needed for family commitments. Therefore, be respectful of their time and priorities by keeping difficult conversations as brief as possible – no longer than 15-20 minutes – with a clear understanding of how much time they have.

2. Lean In to the Difficult Conversations

  • Identify what you’re trying to accomplish
    • Before you say one word, be clear in your own mind what exactly it is that you want to accomplish or communicate.
  • State specifically what you think the person did
    • People don’t usually have a problem hearing that they’ve done something wrong–it’s having to acknowledge responsibility for their actions that gets them defensive. Difficult conversations are especially dicey when emotions escalate; people get more hurt and angry, which makes it more difficult for them to hear what you’re saying. Be sure your intentions are right by starting with “I” statements instead of “you” statements–which will deflect any defensiveness on the part of that other person. If possible, cite specific examples or even evidence of behaviors (not feelings) to support your perspective.
  • Describe the impact of their behavior
    • What results did you see as a result of them doing what they do? What has it cost (time, productivity, affecting others’ morale)? Difficult conversations are tough because people often hear “feedback” as being criticized–and then simply shut down. Diffuse this by focusing less on them and more on impact to your organization. Be sure to describe how their personal attitudes or behaviors have affected you, other team members, or customers–or even perhaps themselves by using phrases like “You’ve made me feel…”

3. Check Progress & Agree on Next Steps

  • Remain open-minded throughout difficult conversations
    • Sometimes people don’t hear us or understand our perspective until we’ve given them all the information and they’ve had a chance to process it. Difficult conversations often elicit strong reactions, so give this person some time to think about what you discussed and come back with any questions before moving forward.
  • Stay flexible throughout difficult conversations
    • The best way to avoid conflict is through open dialogue–and both parties really listening to each other. Difficult conversations involve humanity, warmth, empathy and respect–which means that if your first attempt doesn’t work, try not to take it personally and just keep iterating until you find a way through. Difficult conversations might require several iterations before either party feels satisfied with the results; this is normal!
  • Difficult conversations require both parties to stay flexible and open-minded throughout.

Difficult conversations really test your ability to listen, understand, empathize and collaborate with others — and can therefore open new levels of trust and respect. Difficult conversions might be challenging at times, but remain respectful, honest, and empathetic throughout the entire conversation — even if it means agreeing not to agree on certain topics!

Difficult conversations can bring about new insight or awareness from someone else’s perspective.

Difficult conversations are essential for building great relationships and professional environments.

Difficult conversations can also bring about new insight or awareness from someone else’s perspective.

Difficult conversations might require several iterations before either party feels satisfied with the results, this is normal!

Difficult conversations might even lead to a healthier work environment where everyone thrives and delivers the best results under the pressure of being held accountable for their actions.

Difficult conversions are essential in building great relationships and professional environments.

Difficult conversations bring closure to both parties involved (the one who is having difficult conversation as well as those receiving feedback) ensuring that they mutually understand each other better.

Difficult conversions are essential in building great relationships and professional environments. After all, you’d rather have tough conversations now than have them erupt later down the road or catch you by surprise! Difficult conversations might be challenging at times, but remain respectful, honest and empathetic throughout the entire conversation–even if it means agreeing not to agree on certain topics!

ICONIC inner circle with Scott McKain
Path to Distinction