Tips to move any conversation forward

As a member of the “leadership team” at the various companies I’ve worked for, a lot of my job was talking to people. Leads of other teams, engineers, “senior management,” and so forth.

Most of the time, those conversations went just fine, but occasionally we’d get stuck. There are two important ways in which a conversation can get stuck, and I call them “the logjam” and “the loop.”

It’s frustrating for anyone to feel like the conversation isn’t going anywhere, and sometimes that leads to conflict and distraction from solving the problem everyone came to solve, so here are my coaching-inspired tips for moving any conversation forward.

Recognize the challenge

As with most things, the first step to getting to where you want to go is knowing exactly where you are. Learning to become aware of “halting conditions” in conversation is how you will know what next step to take.

“The logjam”

When you’re in the logjam, you are stuck, blocked, at an impasse. You may recognize this as actual silence, language of futility (“I don’t see how that’s possible,” or “that would never work”), or even the start of an argument.

The key thing to note here is that all forms of logjam are impediments to progress. Whether what you’re discussing is actually possible or not, simply saying “that’s impossible” doesn’t solve any problems; it doesn’t reveal more information nor does it present solutions.

“The loop”

The loop is also called being in high-spin, talking in circles, etc. The primary characteristic of the loop is that the same ideas are repeated, or the same themes are revisited, again and again, with different words.

The key thing to note here is that being in high-spin can feel good. For instance, when discussing the viaiblity of an idea, it can be easy to fall into a loop of just commiserating about the chronically broken or inefficient ways in which the company works rather than facing the realities of solving the problems at hand.

Strategies to move forward

When you’re in a logjam, you can use some techniques from coaching to raise awareness about the situation and find a different path to take to get out of the bind.

You can start with a broadening intro, like “let’s take a step back from the details for a minute,” then try a classic open-ended question. An open-ended question is one that cannot be answered by “yes” or “no.” In some cases, neither you nor the person you’re talking to even knows the answer to the question.

Here are some of my favorites:

• “What would so-and-so (this could be anyone) think about this?” You might try a mutually respected colleague, or get fun with it and name a famous CEO or athlete.

• “In six months from now, assume that we have this all figured out. What did we do?” Sometimes looking from the future back to the present puts enough distance between you and the problem to see something new.

• “What would it look like to do things entirely differently?” The goal with this one is to break down assumptions.

• “Maybe we can’t see the path from here, so what would it look like from a helicopter?” Perspective-shifting questions can take many forms, so pick something that feels natural to you. Helicopter, submarine, through the eyes of a time traveler, it doesn’t matter, get creative!

The purpose of this type of question is to radically change your perspective on a problem. Usually when a problem appears to be intractable, it’s because everyone is looking through a specific lens that they’re comfortable with.

You have to get uncomfortable to find an answer.

If you observe that you’re in high-spin or talking in circles, the above open-ended questions could be one way to proceed, but more often the ground is getting re-tread because someone in the conversation has an ax to grind.

At some level, everyone has an ax to grind about something. The first step is to recognize if you’re the one doing the ax-grinding and gently redirect the conversation toward outcomes. If it’s someone else grinding their ax, we can turn to more classical negotiation tactics.

The best negotiation book in my opinion is Never Split the Difference by former FBI hostage negotiator Chris Voss.

Based on Voss’ writing, the best way out of conflict is building trust and gathering information.

• Listen closely
• Repeat/mirror words and body langauge
• Watch your tone
• Acknowledge and label emotion

Typically once you let someone “empty their bucket,” you’ll see a dramatic shift in their willingness to get out of that loop and help find the way forward.

While Never Split the Difference is still, in my opinion, the best tactical guide to navigating an adversarial negotiation, a lot of the techniques Voss talks about are also central to coaching.

Listening actively, noticing and describing what is happening, and accepting what is said without judgment are all core coaching concepts that create a productive and courageous space for solutions to be found.

If this was useful to you, or if you’ve experienced other modes of “being stuck,” I’d love to hear from you.

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