communication challenges

The 4 Toughest Communication Challenges Leaders Face

As a leader, your communication determines your success. That’s how you accomplish your goals and plans every single day. But just because you do it every day doesn’t mean your communication can go on “auto-pilot.” At the point communication becomes routine, it’s no longer about leadership. It’s typically lacking.


Communication Challenges Leaders Face—the Big Ones!


Listening to Your Team

Contrary to what some may think, it’s not all about output. Over the years, the most significant challenges typically involve the incoming. Here’s why….

Many leaders feel compelled to be the person with the answers. So they often get stuck in output mode. That doesn’t mean they refuse to go through the motion of listening. In fact, before making big changes or launching big initiatives, they often make a big to-do about “listening.” They may survey customers, gather polling data, put together focus groups, or hire consultants to advise them.

But when all the hullabaloo blows over, a lot more is said and done than heard. Nothing that was said and done changes what the leader intended to do from the start. All the “data-collection” activity camouflages the actual lack of listening.


Getting Honest Feedback

You as a leader may be fortunate enough to have a very close working relationship with your team and your own boss. In fact, you may work together as peers rather than supervisor-employee. But many don’t.

Hearing the voice of their boss or seeing a text or email message pop up strikes fear in the heart of many a staffer. Or at best, these messages make the team member ill at ease At worst, they’re thinking, “What did I do wrong now?” At best, they’re thinking, “What do I need to do to impress the boss?”

A common question senior leaders ask: “How can I get my staffers to relax enough to tell me honestly what’s going on? To tell me how I can support them and help them do a better job?”

Leaders often forget that others lack the same self-confidence that comes naturally for them. They have to stay ever mindful of the tension team members feel when simply addressed, and work to reduce that feeling.

To build camaraderie that encourages open communication, show vulnerability yourself. Be willing to share stories about times you’ve made mistakes, times you were unsure of your decisions, occasions where your judgment was not the best. Own up to situations where you did not meet your goals.

Such transparency builds a solid bridge of trust and encourages team members so that you get honest feedback to learn what’s really happening with them.


Reframing Complex Problems 

Book editors famously tell would-be writers: “Show, don’t tell.” By that, they mean, “Create a scene and let the reader see how your characters behave.” Of course, writers find it much tougher to create a plot that reveals an arsonist at work than just to tell us the next door neighbor is an arsonist.

Likewise, leaders find that it’s far more challenging to lead people than simply to tell them what to do and how to do it. Yet asking the right questions to lead an employee to reframe a situation and evaluate his or her performance can be one of the most helpful conversations leaders initiate.

“How do you think this project turned out?” “What would you do differently next time?” “What outcomes should we measure next time to get a better handle on measuring long-term success?” These are provocative questions leaders ask of their team members as they coach for better performance.


Delivering Bad News

Bad-news conversations and presentations are particularly challenging because leaders understand their primary role is to motivate and inspire. Bad news and the resulting disappointment jar that vision and make them uncomfortable—something to be overcome.

That’s why you’ll frequently see them hand off bad news to the HR team or an outside consultant to deliver. Or if they communicate the message themselves, it’s often done impersonally by mass announcement or email so they get no incoming response.

Leaders often tackle bad news like the golf course: Hit the ball OVER the sand trap or the water hazard to get the hole in one. It’s not until leaders adopt the mindset that working through the bad news may be the path they have to travel to land “on the green.”

But if you as leader duck tough coaching and conversations often enough, you’ll eventually be seen as only a cheerleader. To keep the relationship in balance:

  • State your criteria or reasoning for a negative decision and then be direct with the bad news.
  • Stay as positive as possible in your phrasing, but without sugar-coating.
  • Show empathy
  • Focus on the future

If people respond in a less-than-positive way, listen. Acknowledge any feedback for whatever value it may have to you. Maintain your empathy and your positive focus on the future. Repeat as necessary.


Master these four toughest communication challenges, and you stand out as a leader of leaders.


Learn more ways to overcome leadership communication challenges in Communicate Like a Leader: Connecting Strategically to Coach, Inspire, and Get Things Done.

Get more tips delivered to your inbox, click here to subscribe to Dianna’s ezine.