Handling Tough Conversations in 3 Simple Steps

“What’s the hardest part of your job?”

“Tough conversations,” he answers with a sigh.

There it is again. Over the last six years, I’ve been conducting an informal survey in Fortune 500 companies. I keep expecting managers to say their biggest challenge is something like, “Keeping control of the budget.”

But tough conversations continue to be a serious issue. No matter your industry, or your position in an organization, engaging in important or difficult conversations is an uncomfortable aspect of our jobs.

Why? Conflict makes most people nervous, so we avoid having those tough conversations, even if we know it may produce a better outcome. A study of more than 1,000 project managers across 40 companies found that if project leaders were willing to break a code of silence, they could substantially improve their ability to execute on initiatives. This included over 2,200 projects, from $10,000 IT projects to billion-dollar restructuring efforts.

Handling Tough Conversations

But what did the code of silence surround? The key problems that lead to most project failures: unrealistic deadlines, sponsors without internal influence, or unsupportive teams. These issues should have been addressed immediately. But the code of silence allowed them to balloon into major problems.

We have many reasons to avoid difficult conversations:

“If I ignore it, perhaps it will go away.”

“She’s so busy. I shouldn’t waste her time.”

But what happens then? The behavior continues. Many managers have admitted they are uncomfortable addressing even small issues: coming in late, failing to collaborate, and believe it or not, personal hygiene!

They avoided the issue until they had to involve HR. What a disservice to the employee, the organization and themselves! One small conversation, though uncomfortable, could have turned that person around—saved a career and avoided the need for costly actions by the organization.

Honest conversations build trust and appreciation. Everyone can tell a story about someone giving them straightforward advice. It stung at the time, but gave us insight into others’ perceptions. What a gift! Those tiny conversations are often the turning point in a life or career.

Coaching Isn’t Telling

Coaching techniques ease the pain of tough conversations. Coaching is different than supervision. It is not about telling someone what to do. It is about two people working together toward a positive outcome in performance, behavior or relationships.

Connect, learn, act. Follow these three simple steps every time you engage in a tough conversation. It creates an environment of trust, reminds you to listen more than tell, and creates a proactive action plan.

Step 1: Connect

Identify an opportunity to help.

What performance metric or behavior needs to be discussed? Example: John’s been coming in late.

“John, I’ve noticed that you’ve been arriving about 15 minutes late for two weeks.”

Are you both prepared?

Pay attention to the setting and mood. If it’s not right, set a different time.

“I’d like us to sit down and talk. Can we do that now, or would it be more convenient during lunchtime?”

State your positive intentions.

Let the person know that this is not punitive.

“John, I value everything you bring to our team. I want us all to work together.”

Step 2: Learn

Uncover perceptions.

Ask open-ended questions. They require long, narrative answers and are the opposite of closed-ended (“yes/no”) questions.

“John, could you please tell me about your mornings and your commute?”

Listen reflectively.

Reflections clarify your understanding.

“What I hear you saying is that your wife’s new job is farther away. You’ve had to reverse morning duties permanently. Tuesdays are tough since the kids take a special bus. Is that right?”

What strengths can be leveraged now?

“You are one of the best people on the team for time management. Could you use some office strategies for your mornings?”

Create a vision.

Get a picture of the perfect outcome that you can both agree upon.

“John, if you could describe a perfect week, with you fulfilling your family’s needs and being a reliable team member, what would it look like?”

Brainstorm ideas to make it happen.

“Your kids could stay at the neighbor’s for 10 minutes some mornings. We know Tuesdays are tough for you so we’ll make a 15-minute cover plan. We’ll ask Janice, our intern, to cover your desk on certain mornings. We could team-teach your expertise so others can answer questions, etc.”

Step 3: Act

Take action.

Reiterate why you’ll be taking action immediately.

“We’re making a plan right away for this new schedule because we can’t be left without technical expertise, and we want your family to have a comfortable routine. We also want the team remain supportive of you.”

Collaborate on next steps.

Choose one action for each of you to take.

“John, I’ll speak with Janice today about covering your desk on Tuesdays. You contact your neighbor to trade mornings.”

Discuss how to be successful.

“Please share your new schedule with the team. They need to understand so they don’t make up reasons.”

Set a SMART (Specific, Measurable, Action-based, Realistic, Time-bound) goal.

“I will speak with Janice by the end of today. She’ll cover your desk tomorrow. Please tell the team today about your challenges and your plan. By Friday, we’ll discuss your full plan. Then on the following Monday, you can present to the whole team.”

Commit to follow-up.

“Let’s set a meeting for next month. We’ll assess how it’s going for you, the team and your family.”

Enjoy the Collaboration

One important tip to remember: The step people usually want to skip over is Learn. People want to get to a solution quickly, and we all believe we know best, right? So after supervisors make a connection, they often start telling the person what to do. Instead, be a coach. There may be a far better process or solution inside the mind of the person you are coaching. This person has to come to a solution themselves. Enjoy learning just how creative and collaborative your team can be, and enjoy the outcomes of those conversations.


Karen Hough Karen Hough is the Founder and CEO of ImprovEdge, and the Author of The Improvisation Edge: Secrets to Building Trust and Radical Collaboration at Work, published by Berrett-Koehler. She speaks internationally and writes on negotiation, leadership, sales, and presenting with impact, and is the recipient of the Athena Award for outstanding woman-owned business.

13 Reactions
  1. This is a problem that permeates every circle of human relationships from dating to marriage to the workplace. We avoid conflict because it is painful, or at least we think it will be painful, for us or the other person. We’re taught to avoid pain. Until we realize that a little pain now will prevent a lot of pain later, we’ll continue avoiding and making the situation worse. Great article.

  2. You’ve hit the nail on the head here – avoidance of a small issue (through fear of conflict) creates great, big problems. And how much we all have loved to have received honest feedback a few key times in our lives? Thanks for the comment.

  3. Karen,

    I agree with Robert, this approach translates into so many other facets of our lives. With our team, if we rely on truth in our conversations, we have half of the battle fought. It’s delivering that truth in a manner in which our team will receive it the best.

    We spend too many resources on training and growing our teams to not motivate them properly to be as effective as they can be. Way to “coach” us up!

    Warm regards,

  4. Love this! It is truly important to note that this thought process begins the conversation takes place. By viewing it as a conversation not simply as a monologue from the onset helps set the tone of the conversation.

  5. Your comments remind me of a key moment early in the development of my company. An executive came up to me after a session and said, “This will really make a difference at work. I just wish I’d known it years ago for my family. Thank you.” That meant the world to me, and let me know that this sort of conversation was meaningful in so many ways.

  6. Hey Karen,

    Can I add a fourth! The three points you’re making are an excellent framework. One thing I’d add is to ‘digest’ these difficult conversations and/or exchanges and see how one can improve upon them the next time.

    I find that having a little distance gives one more perspective to reassess these scenarios.



  7. I soo Love This..
    I call this process something very similiar= Connect, Clear, Create.. I love the action part of it!!

    I teach the spirituality of Business through Partnership and there is nothing more important then an individual being able to speak their truth.. Without our greatest gifts we’d still be sitting in the dark..

    Thank you!

  8. Karen, absolutely. As a 40 yr old manager, I was challenged till I sat in on a 22 yr old communication coach’s session and saw her doing something similar. I’d only add one suggestion – it is valuable to say something like “we’ll review whether these are working well enough after 2 weeks. Let’s share if one of us comes up with a better idea in the meanwhile”. Continue to monitor and reinforce successful changes in a couple of days.

  9. Hey there, Manoj, thank you for your comment. Ongoing management and communication is critial!