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Stuck Conversations: The “WTF Moment” and How to Deal With It

Updated: Jul 17, 2019

Stuck Conversations

What do you do when you’ve tried, you really have, but the conversation is still stuck? And not stuck in a disagreement so much as jammed in some kind of twilight zone. It’s as though you’re saying “I think the music is too loud”, and the other person is hearing “it’s dark blue, with yellow stripes”. You’re not even close.

Perhaps you’ve described a deadline multiple times, and now the person you’re talking to says they never really heard it, don’t think it’s valid and aren’t going to make it anyway. Maybe you gave clear feedback about not missing a regular meeting, and the other person agreed, and the meeting came, and they didn’t show up, again. Or you talked to your boss about not going around to you to change engineering tasks and, whoop, there they are, doing it, again.

Now you’re talking about it, again, and it’s as though you are speaking a foreign language. Nothing seems to be landing.

The WTF Moment. Baffling. Possibly frustrating, depressing.

Dealing With the WTF Moment, Step 1: Realize You’re In It

A WTF Moment = Fear

The first, most important, step is realizing you’re in a WTF Moment — becoming conscious of your state.

As humans, we get very uncomfortable when we fail to connect with the people around us. At a fundamental level, we need, and thrive on, connecting — being understood. In a WTF Moment, that connection has dropped, and our reaction is, at some level, fear. Fear that we won’t be seen.

Our reaction to not being seen and understood is emotional, visceral and deep.

In addition, in the work setting, the fear is amplified because we want something from the other person, and it looks like not only are we not going to get it, the other person doesn’t see our need, our urgency.

We have to catch our emotional reaction: fear, anxiety, possibly frustration, before things go much further. If we don’t, our emotional system will take over, causing us to get more attached to our point of view, and more determined to force the other person to understand it.

If our emotional system gets control, we will repeat what we’ve already said, but louder, probably with shorter words, probably with an edge (“what I said was…”). Pretty soon emotion becomes the content of the conversation, and the actions of both sides become more or less unconscious, and it ends in either baffled stalemate (“I give up, keep doing what you’re doing. whatever”), or confrontation (“I give up, you’re off the team”).

Going unconscious

Catching the Emotional Response

Think back to when this has happened to you. What does your body feel like in these moments of bafflement, anxiety? What words do you use? How would you describe the emotion you feel? How will you spot it next time? Dealing with these moments, like very many management challenges, requires checking your emotional state, and then picking up the right tools.

Once you feel the bafflement, the anxiety and stress, you’re in a WTF Moment. Once you recognize it, you have the opportunity to make a conscious choice and adjust to step 2.

Step 2: Be Genuinely Curious: Decide to Understand

The problem is that you don’t have enough information. Something is happening inside the other person, and you don’t know what it is. Simply repeating your point of view isn’t the way to find it. You need to decide to the genuinely curious.

Making the switch to being genuinely curious is a conscious act of will. It’s a decision that you will be genuinely interested in discovery, that you will be actively seeking new information, understood by both of you. Once you’ve made that choice, you’re engaged, you can choose the appropriate tools to work with.

Being Curious: Ask Open Questions

“Open” questions are ones that invite a conversational response. “Do you understand what I’m saying?”, isn’t an open question. It invites the response “yes”, which in the case of a WTF Moment is clearly untrue, or “no”, which you knew already.

What? and How? questions open the conversation

Questions that start with “What?”, or “How?” tend to be open questions. “What are you hearing when I ask you to change your behavior?” is open. “We have agreed, a couple of times, that you would check your code in on time, and we’ve agreed that you haven’t. How do you think we should move forward?” is open. Simply, “what is going on with you right now?”, when asked with genuine curiosity, is a great open question. It opens up what’s happening below the facts of the conversation, in the emotional mire, where the confusion almost certainly lies.

Asking open questions takes practice, but the practice provokes conversation, which is what you need to move forward.

Why? questions close the conversation down

As an aside: questions that start with “Why”, tend to have a “pinching” effect, closing down the conversation. “Why are you checking your code in late?” has the sense of a challenge rather than an invitation. “What is going on when you check your code in late?” is an invitation.

In tech industry, particularly, we love the question “why”. Often, it’s the right question, and powerful. When you’re looking to get to shared understanding in a stuck conversation, it’s not your friend.

Being Curious: Listen to Understand

Our listening is governed by our intention. You may, for example, listen with the intention that somebody be wrong. In a WTF Moment, you probably will, since you have a strong point of view and they apparently (maybe, probably) have a very different one.

When you listen with the intention that they be wrong, you are hearing the words coming back, but your mind is watching, selecting for wrongness. You will be hearing: “blah blah blah WRONG… blah blah WRONG… blah blah blah WRONG”.

Listening with the intention that the other person be wrong

Your intention sets the filter with which your mind sieves what you’re hearing. To move past a WTF Moment, you have to set your intention to deep curiosity, to being completely open, to really understand what is being said. Again, you are taking a conscious step here, working skillfully to adjust your approach.

If necessary, tell the other persons what you heard. If you need a formula, use “I just want to make sure I heard what you said. I heard…”. If that’s too canned, find your own way. Ask them an open question about what you heard (“how close am I?”). Listen again.

Being Curious: Be Patient

Being curious when it is most necessary is hard. You want to get to a conclusion, your brain is making all kind of assumptions about the other person (“they’re lazy, not listening, off in their own world, going to quit anyway”), and your emotional system is telling you that the situation is unstable and scary.

It takes time and care to ask questions and parse partial, sometimes opaque, answers — you’d rather just put your foot down. Take the time. Be patient.

Step 3: Repeat Until Some Piece of Shared Understanding Appears

At some point, the other person will say something that you understand. It probably will be something personal (“I’ve just had my 30th birthday, and it freaked me out”, “I’ve just become very uncertain in this role”), but may be something (to you) trivial (“I don’t like the noise in the office in the morning”).

You don’t know what it will be — that’s the point. But once you have it, it’s a start, a small stable place you can both stand. The conversation has become, at least a little, unstuck.

There is, of course, the possibility that your patience and time will run out, and that you will judge that this conversation has to end, and a decision be made. That happens.

But you will have done the best you can to really connect with another person and share understanding. Which is a gift, to them, and to yourself.

Postscript. This Isn’t Easy

Deliberately, consciously and carefully pushing yourself to understand another person isn’t easy. I wish I could say I had been able to get there when I was running organizations back in the day. I managed it occasionally, but mostly I didn’t. It was much easier to go with forcefulness and volume than understanding.

Forcefulness and volume are short-term solutions and, in the short to medium term, they work. But they don’t build deeper, stronger relationships, and they don’t allow us the privilege of finding the strength and hidden talents in other people. Curiosity and patience do. Not easy. Worth the cost.

(If you’re in a leadership position in tech, particularly product and engineering, and you’re interested in coaching, drop me a line)

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