How to Navigate Difficult Conversations

A Difficult Conversation: is a discussion between two or more people where (1) conflict exists or may arise, (2) viewpoints differ, and (3) emotions are charged.

As leaders, we have an obligation to our people, our colleagues, our organization, our customers, our owners and any other stakeholders to do all that we can to assure our company’s positive and productive working environment. This means addressing problems on a timely basis – and that invariably means stepping up and having a difficult conversation(s) with those who may be the root of the problem.

When we step up to the problem and the challenges it may involve, we are sending an important message to our people, that we care about them and our organizational culture. In my opinion, if a manager isn’t willing to lead difficult conversations, they really don’t deserve their jobs (I know, it’s a tough message. I wrote it because I want you, your team and organization to grow and prosper.) 

Giving tough feedback is a difficult conversation. Confronting a top performer who "doesn't play well with others" and is prone to defensiveness is a difficult conversation. Asking a colleague whose a friend at work to refrain from interrupting you with the latest gossip is a difficult conversation. Having to fire someone is a difficult conversation. Requesting that your boss do less micromanaging and more delegating is a difficult conversation. Finding a way to tell a coworker that their breath is reminiscent of a wildebeest with questionable dietary habits is a difficult conversation.  

Regardless of the topic, difficult conversations share two traits: they’re hard and they suck. Yet, if you really want to be a leader (and it’s okay if you decide you don’t), leading difficult conversations with care and candor is not something you can neglect, even if you’re convinced you can work around them or they’re not that important given you’re long to-do list.

The skill of leading difficult conversations comes with practice (Question to self: “When was the last time I practiced having a difficult conversation before I had the conversation?" Assuming you had one. 😉). And lots of awkward attempts and outright failures. I could cite in my own life and with the people I've known and coached story after story of failures so terrible and haunting you’d never even consider stepping up to the responsibility. That’s not the point. The point is any difficult leadership skill requires a gym and muscle building analogy, so here you go. If you want biceps (And I do), there’s no shortcut—you’ve got to do the reps.

You must practice, role-play (I know, ugh!), and rehearse these conversations repeatedly. You’ll get better over time, and it won’t be so awful. But here’s the part you probably didn’t expect: there’s a strong possibility (Depending on your “relationship bank balance.”) you’ll provide someone the kind of insight nobody has offered them before. Think about that for a moment. You, as a leader can help break lifelong habits, shine a light on blind spots, and help someone change their personal brand for the better. Unlike countless other leaders who are well-intentioned but never exercise the courage to be honest while allowing the person to hold onto their dignity as a human being, you can change the entire trajectory of someone’s life. Now that’s leadership in action.

If you’re willing to allow for such a possibility, I guarantee it will change the way you think about leading difficult conversations. There’s an art to delivering feedback and facilitating insight that unequivocally makes the necessary points AND keeps a colleague’s self-esteem and self-confidence intact. Any jacked-up jerk can deliver harsh and demeaning feedback. It takes diplomacy, empathy and thoughtfulness to ensure that the difficult conversation keeps the receiver’s self-esteem strongly intact, while giving them hope and a path forward on how to improve.

What’s the “secret?” Let me suggest three things: 

1. Good intent (See balancing care and candor below);
2. Practice (With a friend or accountability partner) and learning from experts;
3. Engage a leadership coach. 

Check out these posts for more information about coaching.

COACHING WORKS: HERE's WHY

SMART COACHING WORKS: HERE's PROOF

Balancing Care and Candor

Here is how care and candor work together in leadership:

Caring Values the Person While Candor Values The Person’s Potential. To lead successfully, it is important for you to value people. That is foundational to solid relationships. Caring for others demonstrates that you value them. However, if you want to help them get better, you must be honest about where they need to improve. That shows that you value the person’s potential and requires candor.

If you’re candid with someone but with their benefit in mind, it doesn’t have to be harmful. It can be like the work of a surgeon.  It may hurt, but it shouldn’t harm. As a leader, you must be willing and able to do that. If not, you won’t be able to help your people grow and change.

Caring Establishes the Relationship While Candor Expands The Relationship. The things that usually help to establish a relationship are common ground and care. But those things usually aren’t enough to make a relationship grow. To expand a relationship, candor and open communication are required. Many leaders have a difficult conversation that they know they need to have but are avoiding. Usually they are reluctant for one of two reasons: either they don’t like confrontation, or they fear that they will hurt the person they need to talk to.

Caring Defines the Relationship While Candor Directs The Relationship. Solid relationships are defined by how people care about one another. But just because people care about one another doesn’t mean that they are going anywhere together.  Getting the team moving together to accomplish a goal is the responsibility of the leader, and that often requires candor.

Therefore, leaders give up the right to cater to an individual if it hurts the team or the organization.” If you want to lead people well, you need to be willing to direct them candidly.

Caring Should Never Suppress Candor While Candor Should Never Displace Caring. The bottom line, which has already become very clear, is that good leaders must embrace both care and candor. You can’t ignore either. So, to help you strive to keep the balance between the two, here’s a candor checklist for working with people. Before having a difficult conversation, make sure that you can answer yes to the following questions:

• Have I invested in the relationship enough to be candid with them?
• Do I truly value them as people?
• Am I sure this is their issue and not mine?
• Am I sure I’m not speaking up because I feel threatened?
• Is the issue more important than the relationship?
• Does this conversation clearly serve their interests and not just mine?
• Am I willing to invest time and energy to help them change?
• Am I willing to show them how to do something, not just say what’s wrong?
• Am I willing and able to set clear, specific expectations?

As leaders, we must have courage to come out from behind ourselves. We cannot ignore a problem by our seeing reality as we would like it to be. No, we must accept the true reality and do our best to resolve a problem. This is our responsibility. 

Want to know how good you are at this leadership essential? Here are five simple statements: see if they are true of you (if you find it difficult to step back and be objective about the answers, ask a colleague who knows you to help you out).

• I don’t avoid difficult, painful or negative issues and address them when they arise.
• I’m direct, but graceful and diplomatic when addressing such issues.
• I don’t fudge things—I’m clear and unambiguous when discussing a difficult issue.
• When discussing difficult or negative issues with people, I work hard to ensure there are no ‘hidden agendas’—on my part or others.
• I’m open and non-defensive when dealing with difficult or negative issues.

Having difficult conversations is an art, and if we are going to be an effective leader, we must practice in order to develop these skills. (Coach Knight remarked, "Everyone wants to be on a championship team but nobody wants to come to practice.")

Click here to learn how to lead a difficult conversation with an employee whose not being a team player.

Also, there are helpful books, numerous articles, TED talks and YouTube videos which will help prepare us to address rather than avoid conflict. I particularly value the book Difficult Conversations: How to Discuss What Matters Most. It's a gem!

To your greater success and fulfillment!
Peter Mclees, Leadership Coach, Trainer and Performance Consultant

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