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13 Ways to Make the Tough Talk Just a Little Bit Easier

"You should talk to him."


"Why not?"

"It's not that big of a deal."

"It is a big deal and you need to address it with him."

"I can't. We're friends. He might get mad."

Sound familiar? Maybe you've had this exact conversation with your boss. For me, this was the conversation with my boss. I had been on the same team with this guy for years, then I was promoted and he was continuing to miss important deadlines. Since I've worked with him for so long, I knew he didn't take criticism well. I was also worried about what it would mean for our relationship if I addressed the issue with him. My boss continued to press me until I finally gained the courage for the difficult conversation.

Yes, he got upset. Yes, he denied some of the things that I said. Yes, I felt awful. Then, after about a week, things got better. He was better at following timelines and our relationship had been restored. It was the right move — I was just too scared to have the courage to take the steps.

Maybe you're like me and fear the difficult conversation. Or maybe you're like my wife, who is the peacekeeper of the family — one who doesn't want to stir the pot and who avoids conflict like it was a date with the dentist. Besides, "Blessed are the peacemakers," right? I mean, if we give it time, everything will work out. We don't need to have the difficult conversation, can you agree?

Unfortunately, this line of thinking is wrong. There is a time for keeping the peace and there is a time when we have to risk a little war.

When an employee makes a big mistake or when there are ongoing chronic issues with little things after you've said something, it's time to have the tough talk. Your boss wants you to do it, the rest of your team wants you to do it, and it’s the right thing so you should muster up the courage and just do it. Delaying the talk, or never having it, is bad for three reasons.

First, the organization suffers. Yes, one rotten apple really can spoil the whole bushel. The longer we let serious violations go on, the more it impacts the team. They get upset and irritated. They talk more and more about the employee to others. They may even start to show bad behavior just to spite you or the system.

Second, you suffer. You suffer because you know you need to have the conversation and you are not taking action. This subconsciously bothers you. This starts to eat at your confidence as a leader. You lose focus and get quick with people. Plus, you suffer because your team is losing trust in you. If they can't count on you to have the difficult conversation when there is a clear violation, when can they count on you?

Third, they suffer. This is not always the first thing that we think of when a situation needs to be addressed, but it’s true. They suffer because they are continuing to perform in a way that is not consistent with their best self. Maybe they know the problem and just need help overcoming it. Maybe they don't know the problem and need someone to point it out to them.

Justin is a good friend with whom I entered into a business partnership. He was giving a speech to a rather large group of business owners. The speech was good, the content seemed to resonate, but there was something that was off. He wasn't connecting with the audience. It was like there was something stopping them from trusting him. And then I noticed it. He wasn't keeping eye contact with anyone. As I thought about this, he didn't do this with me either when we first met. It was one on one and he couldn't look at me. At first, it really bothered me and I couldn't help but question if he was lying to me. Eventually, I got over it. Now he was before this group of leaders and they were wondering the same thing: "Can I trust Justin?" This was going to have a big impact on Justin and our work together. So, I put my big pants on and had a difficult conversation with him.

Interestingly, he had no idea he wasn't keeping eye contact. He just needed someone to tell him and coach him along. Today, he speaks confidently with eye contact and people trust him quickly.

Likely, the issues that you have with your employees will be bigger than simply keeping eye contact. Yet, are they really aware of what they are doing, how it is affecting the team, and what the impact is on themselves? Probably not and that is where you come in.

I wish there were some tool that I could share that would make these difficult conversations happen easily, but there isn't. No matter how you do it, difficult conversations are difficult. I can't lie about that. However, I can help you make this process a little easier by following the 13 tips for tough talks.

#1 - Have Clear Expectations

As mentioned earlier in the book, if you don't have clear standards, how can you hold someone accountable? If I've never told my daughter Ande to do the dishes, how can I justify being upset when she hasn't done them. Peter Drucker said, "One of the critical problems in the workplace today is that there is a lack of understanding between the employer and employee as to what the employee is to do. Often employees are made to feel they are vaguely responsible for everything. It paralyzes them. Instead, we need to make clear to them what they are and are not responsible for. Then they will be able to focus their efforts on what we want, and they will succeed."

#2 - Do it ASAP

If someone sends a nasty email, don't wait till tomorrow to address it. Get up out of your seat and go and have the conversation. If you see one of your employees belittle another with their words, set up a one on one that day. The longer you wait to have the conversation, the less fresh the details will be. For the greatest amount of growth to your employee, have the tough talk sooner than later.

#3 - Don't Assume

This is critical. Too often we think that we have all the information we need to really drill into an employee. Well, you might. Or, maybe you've made a whole lot of bad assumptions. Instead of leading with firmness, give them the benefit of the doubt. Ask questions. Do an investigation. Then, when they've admitted it or you have enough proof, drill into them (with care, of course, and on purpose with controlled emotion).

#4 - Focus on Actions, Not Personality

This is not supposed to be a personal attack. They are not a bad person. They may choose bad behaviors, but they are not bad. This is simply a lack of proficiency. That can always be changed. Therefore, focus on the actions and not on the person.

Saying, "You're always so negative. It's draining for everyone to be around you!" is a personal attack and a bad example of how to have the tough talk.

A good example would be something like this: "There have been times when people have felt hurt from comments that are demeaning. For example, in this email from last week you stated that Stacy's idea was dumb and you questioned why she even works here. The way you expressed your thoughts have had a negative effect on Stacy and on others in the team."

#5 - Be Specific

Don't generalize. Reframe from using phrases like "You're not meeting expectations" and "You need to be a better team member." Tell them specifically what they are doing that does not meet expectations or that causes them to not contribute to the team. Here are a couple of examples:

Vague: "Your email was late, as usual."

Specific: "My expectation was for this to be sent to me by Thursday. Not getting this to me slowed the work we could do on the project."

Vague: “Good effort on the report but I don’t like it. I think there is room to be better.”

Specific: “Good effort but there are some things which can be improved – namely, (a) the formatting and (b) the final recommendations. The formatting is not standardized – there are some parts that use Arial font and other parts that use Calibri font. In a formal report, it is best to have one standard font. For the final recommendations, the ideas are good but they are too brief, especially ideas #1 and #3. The management would need more data to make their assessment on these two ideas.”

#6 - Suggest the Changeable

It should go without saying, but please don't tell someone to change something that they can't change. Asking a basketball player to get a little taller so that they can be a better center is nonsense. So is telling someone to get the project done when it's being held up by others. There may be situations in the person's life that prohibit him or her from changing. Make sure you understand these before telling them to do something that they feel they cannot do.

#7 - Avoid the Deadly 4

When having the tough talk, stay away from these four words:





Are they always late? No, they made it in twice in the last month on time. Do they never care about putting the tools back into their place? Perhaps most of the time but not never. But and however, negate everything you said up to that point. "I love your passion at work, but sometimes you can take it too far and put too much pressure on others." Simply remove the but or however and use two separate sentences. "I love your passion at work." "Sometimes this passion can lead you to put too much pressure on others on your team."

#8 - Don't Buy into the Sandwich Method

You've probably heard of the sandwich method before. For the six of you who have not, the sandwich method consists of three parts: say something nice, give your critical feedback, then say something nice. Stop using this nonsense advice. It doesn't work. No matter what you say before and what you say after, they will never remember it. Bring them in, sit them down, say what needs to be said, then end the meeting. Keep it short and keep it simple. If you are worried about their self-esteem, instead of telling them the good stuff during a tough talk, tell them in four separate situations how great they are for every one tough talk.

#9 - Get Personal

When having the tough talk, it's also beneficial to get personal. What I mean by this is for you to share how their action has personally affected you. What are your feelings, what do you think about it, what has been the impact on your life and/or leadership? Sure, you can also share how it impacts the business, but there might be a chance that they don't give a hoot about the business. Haim Ginott, the grandfather of effective communication, shared how to get personal by using the XYZ system. When you did X, it made me feel Y, and I'd rather you do Z.

#10 - Give a Game Plan

Please, please, please do not tell someone to get better and then leave. They will only be frustrated. I once had an administrator tell me that I needed to get better. In fact, he told me that I needed an improvement plan and then he ordered that I write the plan. His lack of clarity caused huge frustration. I had no idea how to improve, that's why I was in such a mess!

Suggest to them several ways to solve their problem or to improve. Ask them which ideas they like the most or if they have other ideas. Once they've decided on some actions to take, have them put it down in writing and then ask one of my favorite questions: "On a scale of 1 to 10, how committed are you at doing _______?" If they answer anything less than a 7, you'll need to rethink the game plan.

#11 - Affirm Them as a Person

Of course, the whole point of the tough talk is to help them grow. Don't use this to belittle them and don't do it to release your pent-up anger (that is what your boxing bag is for). The main focus of having the tough talk is to help them get better, so they can make the team better so that the business is better. Therefore, affirm them once they have a game plan. This means that you show your support and belief in them as a person that they can change and that they can improve. You need to really believe it and they need to know that you really believe it. John Maxwell calls this the balance of care and candor. He outlines it this way:

  • Care without candor creates dysfunctional relationships. "I love you but I won't be honest with you."

  • Candor without care creates distant relationships. "I don't care for you but I'm bluntly honest with you."

  • Care balanced with candor creates developing relationships. "I care for you and I know you can do it."

#12 - Follow Up

No matter how bad or how good your tough conversation goes, the most critical tip of all of these tips is to follow up. If the conversation went poorly, you'll need to follow up to reemphasize your points or to restore the relationship. If the conversation was good, you'll also need to follow up to ensure follow-through and to restate your confidence in them.

I've found it easiest to set up the follow-up at the end of the tough talk. "John, thanks for your time today. I know this was tough. I'm going to follow up with you in a week. I'm scheduling some time next Tuesday at 9 AM. You can let me know how it is going and I can give you any additional feedback." Again, don't let them leave the conversation thinking this was it. It is not it. Growth and improvement take time. You'll need to continue to follow up, once, twice, three times, or perhaps more.

#13 - Write it Down

OK, so you've finished the conversation, your inbox has grown larger, you have three people waiting to talk to you, and you've not been out to the floor yet. Great, conversation over, let's get back to work. Not quite cowboy! Before you get back to the daily tasks, take a moment and write down a short summary of your conversation.

The purpose of this is to help you remember what you talked about, what the person's plan is, and how you can support them in growing. This will also help you to remember what you'll need to follow up on. In addition to these two purposes, a third purpose for writing it down (and one which I hope you don't have to use often) is that it provides documentation in case your employee refuses to improve and you need to move to termination.

Yes, unfortunately, no matter how great of a leader you are, some people will refuse to listen, apply the game plan, and grow. In that case, and if you've done your best at applying what is in this book, it's time to move towards the even tougher talk. It's time to terminate. If this is where the employee is for you, my suggestion is to schedule a meeting with your HR manager, share with him what you've done, and work together towards an exit strategy that would be beneficial for you and for your employee.

There it is. 13 tips to help you with your tough talks.

I hope this encourages you to have that conversation. As I've worked with leaders, sometimes I'll ask an audience "Who has a tough talk they need to have?" Without fail, almost every hand goes up. My bet is you've got one waiting to happen too.

Uncommon leaders see difficult conversations as a win-win situation and therefore don't delay in having them. If we approach it with the right attitude, do it out of our care for the other individual, and focus on how we can help them grow, you'll find these difficult conversations slightly easier to have and hugely beneficial to you, to them, and to your organization.

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