Clarifying Communication at Work: 7 Tips to Make Difficult Conversations Easier

Over the years, I’ve been called into many companies to assist with the restoration of relationships  that have deteriorated due to one or both parties being unwilling to engage in some difficult conversations. These situations took many forms: the VP whose abrasiveness was tanking partnerships, the executive whose passive yet judgmental management style had built distrust within the leadership team, the sales leader who communicated frequently with passive-aggressive emails.

All of these situations, and many others, stem from a specific fear - the fear of initiating a difficult – or even conflicted - conversation.

Many people aren’t great at dealing with or even communicating around conflicting points of view. Much of this struggle is a learned behavior which often times stems back to our upbringing and whether we grew up in a yelling house or a quiet one; how we learned what was OK to say and what was best to keep quiet. Some of it is about not wanting to hurt someone’s feelings, or not wanting to deal with their negative emotions. Some of it is impatience or anxiety or even boredom with the topic at hand.

But what I tell my clients is this: What goes unsaid is far more damaging than a difficult conversation you enter into with respect and compassion.

A Common Example of How Challenging Conversations in the Workplace are Handled

A classic example of a challenging conversation in the workplace is the manager who avoids talking with their employee about workplace issues. Instead of discussing the employee’s poor attitude or under-performance early, which would set clear expectations for improvement and reviewing progress, the manager waits until the problem has gotten out of control to handle it. By this point, productivity is in jeopardy and the employee’s coworkers are demoralized - all because the manager avoided having a difficult conversation.

This manager isn’t a bad person, they just lack experience. In fact, their behavior is very normal!  But a short conversation at the first sign of trouble can save headaches (and productivity) along the way.

4 Tips for Leaders That Make Tough Conversations Easier

  1. Remember that it’s a conversation, not a confrontation.

    If you’re the type of person who’s worried about hurting someone’s feelings, remember that you’re not dragging them into your office to yell at them; instead, you’re showing them respect and compassion by providing feedback that will help them grow, personally and professionally.

    On the other end of the spectrum, if you’re more prone to snap at someone when you’re not happy with their performance, remember that you’ll get the best results from a two-way discussion. There may be underlying challenges that you can uncover in a conversation and will certainly stay buried if you’re busy making a show of power.
  2. Allow people to fail.

    Cultivate a team environment where mistakes are not only OK, but a necessary part of learning and growth. Leaders the world over have said this every way it can be said - no success comes without plenty of missteps first. If people in your organization are afraid to admit to mistakes, you’re setting up your team and company for perpetual under-performance, loss of competitive advantage, decline and potentially failure.

    Mistakes are learning experiences and opportunities for refinement and improvement. I always say, “I don’t care if you fail or have a negative variance from plan. I just care that we talk about it and learn from it.” Create an environment of safety and high performance – evaluate, learn, improve and grow.  
  3. Make it a habit.

    If you have only one challenging conversation this year, it’s not going to be much easier next year. But one a quarter? One a month? One a week? Now we’re making progress. Soon, it will simply be part of your (and your organization’s) DNA.

    I’m not suggesting you look for opportunities to have difficult conversations; I’m simply suggesting you stop avoiding or delaying talking about under-performance and everyday challenges, and when you’re comfortable leaning into critical dialog as part of your team’s normal continuous improvement process, you’ll find your team and your company thriving. Critical dialog, done with respect and compassion, precedes sustainable growth.
  4. Lead with inquiry.

    I’d like to say that all of your conversation partners will respond favorably to receiving feedback, but that’s not always the case. People will respond to your feedback in a variety of ways: from receptive, appreciative, collaborative to aggressive, defensive, defeated and anger. To diffuse some tension, consider leading with inquiry. Identify what it is you want to say, and then turn that into an opportunity for discovery.

    Instead of saying, “Your behavior was bad,” ask questions like:
    1. Based on your demonstrated actions, how aligned are your behaviors with our core values? 
    2. How do you think your peers would describe your behavior?
    3. If you could re-do this situation, what would you do differently to achieve a better result?
    4. If everyone in the organization were behaving like you, would this be a better or a worse place to work?
    5. What adjectives would your team use to describe your brand?

3 Tips for Receiving Critical Feedback

Everyone, at every level of an organization, should be prepared to receive critical feedback. If you’re better at dishing it than you are at taking it, try to keep these things in mind when you’re on the receiving end:

  1. Assume good intent. Go into critical dialogue with the assumption that the person delivering feedback has your best interests in mind. They want to help you grow, and they want to help your team grow. Try to receive it with an open heart and mind.

  2. Growth requires insight and input. Transformation can be painful, but remember that the discomfort is temporary, while your potential is far greater.
  3. See it as a sign of respect. Only if a person respects your intellect and ability will they invest in your growth and provide feedback. They trust your ability to handle the truth and recognize your drive to improve yourself. Make sure that trust isn’t misplaced.

As you grow in your ability to give and receive constructive feedback, you’ll be creating competitive advantage for you and for your organization. It’s these conversations that serve as the catalyst for continuous improvement. Speed is today’s currency, and the pace with which you and your team makes improvements, corrections and innovations will ultimately determine your organization’s ascent and sustainability.

Are you or your organization in need of a little leadership coaching and development? Get in touch for a free consultation.

Go deeper on the topic of difficult conversations with our related Management Insights podcast episode.

Phil Mydlach

Phil Mydlach is a high-performance executive coach who shows people and companies how to break through to their next level of ability, growth, and performance. He partners with them as they lean into their edge to confront the fears that are holding them back.

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