I had a post written about difficult conversations. It was quite reasonable. Then I read this article by Clayton Christensen on the Harvard Business Review, and specifically this quote:

"Management is the most noble of professions if it’s practiced well. No other occupation offers as many ways to help others learn and grow, take responsibility and be recognized for achievement, and contribute to the success of a team. More and more MBA students come to school thinking that a career in business means buying, selling, and investing in companies. That’s unfortunate. Doing deals doesn’t yield the deep rewards that come from building up people."

I read that and realized my post was far too tame and this topic is incredibly important. So I wrote this post instead:

Having difficult conversations is one of your fundamental responsibilities in living. Difficult conversations are the very essence of love, intimacy, and generosity. And every time you postpone or avoid one out of fear you are wasting your precious life, failing in your responsibilities to others, and acting out of cowardice.

The reason we avoid difficult conversations is simply fear. Facing fear is hard by definition. Fear exists precisely to stop us from doing dangerous things. It's appropriate and good to feel fear if you're about to do something very dangerous. But we also feel fear in a lot of situations that aren't actually dangerous. Difficult conversations are among those.

Yes, there are risks in having difficult conversations. One or both of you in the conversation might experience rejection, shame, or guilt. It might threaten your or their identity, which can be terrifying. None of those are easy things and we have a flinch reflex to avoid them. But difficult conversations are about doing the right thing and being honest when it's tough. 

The illustration is about fear. For some reason, years ago, I was thinking about fear and this image popped into my head: fear is like a molasses surrounding you, oozing in against you. You can push it away from an area by forging into that area yourself. And if you leave an area vacant, fear will slowly ooze back in. It's true of everything: if I haven't been rock climbing outside in a year, the first time I'm 50 feet up on a rope I'm terrified. But I just do it a few times and the fear recedes. It's true with difficult conversations, too. It's important to understand this metaphor because it shows you a few things. First, there is no way around being anxious and afraid of your difficult conversations at first. To push the fear back, you have to wade right in. If I'm afraid of climbing, I can't go practice tap-dancing to make the fear go away. If you're afraid of difficult conversations, only having difficult conversations will make you less afraid. And second, it gets better. Have those difficult conversations and the fear will recede. I promise.

Alright. Let's say you're managing a team. Let's say you have a team member who's struggling, who is missing some core skills she needs to really shine. And let's say it's a really bad case: let's say she actually thinks she's really good at those things, and it's a matter of personal pride, and you know a conversation where you tell her honestly you think they're real weaknesses is likely to go poorly, maybe with tears and/or yelling.

Guess what? You must have that conversation. You owe it to her to have the conversation. It's your job to have that conversation. But it's going to be awful! Is it so bad if you just don't bring it up?

I'm going to be really blunt here because this is important: if you don't have that conversation you are failing. You fail to honor your commitment to that person, and you fail to honor your responsibility as a member of the human race. Management is a serious and solemn obligation: You work diligently to help her with her work and her growth as a person. That's the agreement, that's the contract, and you're chickening out. You should transfer her to a different manager who will do their job. Either that or you should fire her - not because she's failing, but because you are. You should fire her because by keeping her around and not talking about what really matters, you are wasting her life. You can choose to throw your life away, but you cannot choose to throw someone else's life away. Her time is not your time to waste. It is very important to understand your work in this way. Wasting another human being's precious life is a serious, serious offense.

How do you know when you should have a difficult conversation? Obviously you shouldn't berate people constantly just because you believe they could be doing a tiny bit better. Let's say you have someone who's doing fine, could probably be doing more, but when you probe a bit, seems totally content. Just mention to him the options - "If you ever want to do more, we can talk about that" - and leave it at that. He doesn't have a problem. Don't project your impatience onto people. But if you have someone who's not succeeding and wants to be, or who clearly wants to do more and is being held back by limitations he doesn't understand or believe, that's a dissonance. Dissonance is a signal that you need to have a difficult conversation.

This all goes for difficult conversations outside of work, too, but I won't talk as much about that because it gets a lot murkier where the obligation is. Some friendships aren't about brutal honesty; some are. In some cases it's expected, in others it's not. There's more nuance there. In partner relationships even more so, and there's a lot more skill involved (and if you ask my ex-boyfriends they might suggest I'm not exactly qualified to speak as an expert in this area!)

Professional relationships are more cut-and-dried. Helping your reports grow is your job. It is your sworn responsibility to them, and if you aren't going to do it, let them find someone who will.

* * *

"OK", you say, "You've shamed me into doing this. Now how do I approach it?"

If you haven't read my previous post, which was about practicing with intention, now would be a good time, because I'm going to refer to that basic practice a lot on here, starting right now.

The key part of a difficult conversation is being in touch with the proper intention when you go into it. In a nutshell, that intention is this: I am telling you these observations I have made even though it is difficult for me because I care about you and believe they may help you learn and grow.

Here are a few notable things that aren't part of that intention: I expect you to take this advice. My observations are absolutely correct. I am personally attached to the outcome. I know better than you do what's appropriate for you. I'm telling you this because I want you to see me as smart. I'm telling you this because I like identifying as a "mentor" or "teacher" or "wise person."

Now, the reality is, some of those will always sneak in. None of us are saints. But the more you practice seeing your intention and connecting with a pure and loving intention, the closer you'll get. This isn't something you can think your way through. It's practice. Like I said, read the blog post and do the practice.

This intention goes even for conversations where you're telling someone, "If you don't fix these problems I'll have to fire you." Being fired isn't the end of the world, and it's not a personal judgment. It just means a professional relationship wasn't working out. Good people have relationships fail all the time. 

* * *

OK, so you've practiced a bit and you feel like your intention's pretty pure, and now you tell me, "I'm not very good with words. How do I choose my words properly? It's a sensitive conversation, so I really need to be careful."

One kind of planning for a difficult conversation is useful: you have to get your ducks in a row. Figure out the core message you need to convey so you can say it concisely and make it crystal-clear. Know your concrete examples again so you can be concise. "A good example of this is last Monday's production meeting. You seemed visibly agitated when Dan asked you to explain your technical plan, and it felt to me that it had a chilling effect on the meeting." Write a crib sheet if you need it. This planning is important because it allows you to be clear and thus respectful of the other person. 

But worrying over "word choice" is usually concern about the micro-details of the way you say something. "What if I blurt it out and it sounds accusatory? What if I accidentally offend her? How do I know the right thing to say?"

To paraphrase Alan Watts, I say to you: You are asking me that question because you don't want to say it, not really. If you have the proper intention, there's really nothing to fret over. It is, as Watts says, "precisely postponement." You're stalling.

Consider a truly difficult conversation: Let's say it's fallen to you to tell a close friend, someone you deeply love, that someone he loves has died. Be honest: You know exactly what to say. You sit the friend down and say, "I have to tell you something: this person you love has died." And that's it. And then you are there for him in his grief. If you spend any time beforehand fretting about the word choice and telling yourself that it's very delicate and you must rehearse, all you are doing is stalling. The words are simple. They spring from the intention.

It is the same way with any difficult conversation. Sit the person down and tell her, "I have to tell you something. There is a problem. Here are the things I have seen. Here is what they say to me, and here is why I am concerned." Then be there for her. Let her have her reaction. Listen to her with an open mind. And then have a discussion about what actions you both might take.

Practice connecting with your intention. Do it. I can't say this enough. Practice. Sit and see what comes up. Let the self-conscious and self-absorbed stuff drift on by and connect with this: I am telling you these observations I have made even though it is difficult for me because I care about you and believe they may help you learn and grow.

When you sit this person down and say the words you know you need to say, you should not feel proud, or large, or powerful. You should feel humble; you should want to bow your head. You should speak your words as an offering. You should feel sadness as you witness her pain, and joy as you witness her resolve. If you don't, that means: Do more intention practice next time.

I said it up at the top and I'll repeat it here: this gets easier. This is the good news. When you practice having these conversations, you chip away your fear of being real with people, being honest and direct with them, and you learn to approach that honesty from a selfless place of caring for the other person. This is an incredible skill to have and it will deeply enrich your life. I look back on how things used to be even just five years ago before I'd really spent time practicing this, and I see myself held back by fear, or I could call it selfishness. The more I've practiced, the easier it's been for me to start these conversations with people, to be honest and open with them, and the less I worry that I'll just come across as rude or alienating, because I can feel now when I'm coming at the conversation with a truly selfless intention, and when I'm not, well, sometimes at least I know to hold my tongue.

This is especially important because most people don't do it! Most people aren't fully honest with you, or when they are, it's clear they're trying to be hurtful or put you down to feel better about themselves. This ability to offer the truth to others, fearlessly and selflessly, is a rare and precious thing. It is one of the most powerful forms of love there is.

And, if you're a manager, it is one of your most sacred responsibilities.

So go practice.