In the evenings, after we’ve put our son to bed, my husband and I have about an hour, give or take, to spend together. Sometimes we just fall straight asleep, other days we’re prepping lunches, and some days we cave to television. But on the good nights, we chat and discuss the day’s puzzles, processes, and discoveries. Often, while sitting and listening, I’ll find it’s easy to come up with potential solutions for whatever we’re discussing and I’ll try to give great advice.

It’s almost too easy.

It’s fun to brainstorm, to be clever, to solve things.

Have you tried this yet?

What if you do {insert solution here}?

Oh, that happened to me, and I did {this thing} to solve it.

There’s a smattering of satisfaction associated with this—at least for me—because it feels good to solve things. It feels so good, in fact, that I notice sometimes I interrupt, break in, or try to solve something before we’ve even gotten to the root of the question.

In our lives, it’s easy to jump right in and propose solutions before we even understand the scope of what’s happening.

The trouble is, how do we know that our advice is what really needs to be said?

Sometimes we don’t want advice from other people.

Now, sometimes we do: but not always. I’d wager a guess that it’s far less often than the number of times we receive an onslaught of well-intended advice.

What we want, instead, is someone to sit with us and acknowledge that the puzzle we have is real, and to be witnesses to the experience that we’re having. Sometimes—I know this is true for me—we want someone to be in the room while we puzzle it out and figure it out on our own.

We have such a dearth of listening in this world, in this culture.

Listening is extremely hard to do. Listening well is a skill, honed with practice and attention. Krista Tippett, in her recent book Becoming Wisewrites that “listening is about being present, not just about being quiet.” And Michael Gervais, in a recent podcast with Tim Ferriss, talks about working with therapists in his graduate training. One of the school’s requirements was to “sit in the other chair,” and understand the process not just of being the therapist but also the experience of being in the chair. He sat in the chair and realized how vulnerable it is: it’s heavy. It’s hard to reveal yourself. Another human being is asking you questions. Being clear and open requires a relationship with the person asking questions and a willingness to reveal yourself.

Both sides are hard. Revealing yourself can take courage and patience. And asking great questions can be a challenging task in and of itself.

More than a solution to a hard day, we want to be seen. To be understood.

Sometimes self-understanding comes through having the space to explore ideas. To put to words, out loud, ideas that are forming in your mind. Unfiltered, unedited, not justified, not walked back. Just simply put into space, held, and examined thoughtfully.

What happens when we step in and rush to offer advice is that we shut down the space to examine our own minds and mental processes.

When we offer advice, when we rush to speak instead of listen, we aren’t just interrupting: we’re shutting down the possibility for a more effective process of self-discovery.

Why advice doesn’t work

Advice can be brutal, and it can also be ineffective.

In fact, most “advice” is pretty terrible. When we offer advice to a problem we don’t fully understand or listen to, we’re just talking.

Advice, when not matched with the appropriate understanding of the problem, can be useless.

Play this out with me:

Someone comes to me and they say, “I really need to be more productive.”

Me: “That sounds like an interesting question,” I say. “What does being productive mean to you?”

Them: “Well, I’m not getting enough work done, and at the end of the day, I don’t have time to exercise.”

Me: “What does that feel like for you?”

Them: “I hate it. I really miss exercising. I wish I did more of it. When I exercise, I feel so much better.”

Perhaps you can see that even with just a few questions, in this example, we went from productivity to exercise.

The root of the problem was actually finding time to exercise, not finding time to get more done. (And even then, this discovery questioning can continue onwards for quite a while as we explore different facets of the puzzle and find out more of what’s going on.)

It’s really easy to see someone from the outside and think, “Here’s an easy way to solve the problem.” In fact, how many of us jump in with productivity advice with the very first statement or question? Were you ready to say “try GTD,” or another piece of advice for this particular example?

Advice doesn’t help when we don’t take time to fully sit with the question.

As Rilke says,

“Be patient toward all that is unsolved in your heart and try to love the questions themselves, like locked rooms and like books that are now written in a very foreign tongue. Do not now seek the answers, which cannot be given you because you would not be able to live them. And the point is, to live everything. Live the questions now.”

And more importantly, when we sit with each other, witnessing the struggle and the experience and the attempts, we are here, with each other, in the present moment. More than answers to our questions, we want most desperately to connect with one another.

To be seen, and heard, and loved.

And when we let someone know that they are perfectly imperfect, just as they are, without needing anything else fixed in their life… life becomes more real.

Advice can go so far as to be negative, in fact. When we offer advice, we should be cautious that we might also be interrupting someone’s thinking process to suggest that they aren’t thinking deeply enough, they haven’t thought of something, or they’re clearly missing something.

The best thing we can offer is a listening ear.

In the mastermind groups that I work with, there are three key concepts that I’ve tried to map, model and teach. One of them is my monthly and quarterly productivity planning tools. The second is the value of intimate community, especially around sticky challenges and intense periods of personal growth. The third, however, that’s directly related to this post, is the art of a “Deep Dive’ session, where we sit and listen to each other.

In these sessions, we aren’t allowed to give advice. The only thing we’re allowed to do is ask questions. Our job, as witnesses and listeners, is to ask questions to better understand the scope of the problem. It’s been one of the best processes of the entire experience (I’ve had people tell me they take Deep Dives back to their work and colleagues). We aim to practice, for our few months together, the lost art of deep listening and the value of asking better questions.

I ask each person to come to the program with a question that they’re puzzling over. As Clayton Christensen writes:

“Questions are places in your mind where answers fit. If you haven’t asked the question, the answer has nowhere to go. It hits your mind and bounces right off. You have to ask the question—you have to want to know—in order to open up the space for the answer to fit.”

Over the next two weeks, you can apply to the Startup Pregnant mastermind (we start at the end of June), so if you’re looking for a small, intimate community to learn and grow within, apply soon before all the spaces fill up.

And for everyone else: the next time someone asks for your advice or begins to talk about a puzzle they’re working on, I encourage you to consider offering them a thoughtful question in response.

If you don’t have a question at the ready, you can always use what Chris Voss, master FBI negotiator and author of “Never Split The Difference” recommends: repeat the last few words of what someone says, adding an upward inflection to the end of the repetition, to get them to say just a few more words about what they’re working on.


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