Are You Missing The Obvious?

For this article by Jo Ilfeld, Executive Leadership Coach on decision-making, the image shows an image of two arrows facing opposite directions.

Recently I had the joy of spending some time on Cape Cod with my daughter, who was about to go to camp, and one of my oldest and best friends. While my daughter was plugged into her earbuds, my friend and I had a lot of time to talk as we drove around the Cape.

During one of these conversations, we spoke about the challenges of raising Gen Z teens right now. My friend asked me if I had ever brought up these concerns to my own teens? It felt like such a stunningly obvious question, whether I had shared my worries with them. I found myself making excuses, “They didn’t want to have that conversation,” “They shut me down too quickly.” And while many of those excuses might be true, I realized underneath lay the real truth: I hadn’t deeply thought through these concerns myself before talking with my friend, so I hadn’t even thought about having these talks with my teens.

As I stood in line in the airport thinking back on this conversation, I realized that my friend offered me the gift of a thoughtful ear with probing questions, much like what happens in executive coaching sessions.

I’m often astonished by the surprised reaction from my clients when I ask them if they have shared particular stresses with their boss, their direct report, or their “fill in the blank.” It’s often clear they had never considered sharing what was top of mind for them.

As I thought about this more, I found three main reasons why we’re not talking about the obvious.

Here’s my take on why we aren’t talking– and some solutions to make sure we are – about what really matters to us.

1. We’re afraid of the other person’s reactions. The corollary to this is we don’t even know how to even start the conversation.

This is the culprit behind many important conversations that don’t happen. We’re worried we don’t have the right words. That we’ll make the other person mad, or sad, or alienate them.


First write down what is important TO YOU about this topic and what would be a great outcome from this conversation. Too often we get so deeply into the HOW of the conversation that we don’t fully consider the PURPOSE behind the conversation.

Once you have that accomplished, one of the best conversation starters is to ask the person if you two can have a conversation. This is crucial because once the person agrees, you are now having a permission-based conversation and not just foisting it on them. Then you can start the conversation with, “I wanted to talk with you about X because Y,” where Y equals what’s important to you and even what a great outcome would look like.

An example of this could be: “I wanted to talk with you about the last marketing report you sent me. I noticed there were some typos and factual errors and it’s important to maintaining our client reputation that we find new systems for proofing reports.”

2. We think we know how they’re going to respond already.

What’s worse than a know-it-all? A know-it-all that’s wrong!

Too often when we play out conversations in our head, we assume we know more about the other person’s intentions, knowledge, and motivation than we do. We assume errors are the result of not-trying vs. not knowing how to proofread effectively. We assume people are feeling healthy, working on a full night’s sleep and have the same mental bandwidth we do.


Step outside your lens and try to take on the lens of someone else. In one class I teach, I have people come up with as many reasons as they can for someone running a red light. Once people get beyond the “they are a jerk” reasons, they branch out into color-blindness and my all-time favorite, “they are being kidnapped at gunpoint.” 

See if you too can think of at least 10 other ways they might respond, beyond what you’ve envisioned so far. . . go ahead. . . I mean it – write them down! (Then potentially return to point 1)

3. We haven’t taken the time to even realize it’s important.

It’s hard to see the big picture, and thus know what is important enough to talk about, if we’re not taking time to reflect and examine what’s around us. This is one of the amazingly valuable things about having a coach (and a best friend.) When we relax into a space of reflection rather than getting things checked off our to-do list, what is important, but not yet urgent has room to surface.

One of the hardest things for all my clients is to find, what I call “step-back time” in their days and weeks, often because they are buying into one of the biggest productivity myths, that if we’re not doing something, we’re not being productive.


The answer for this is the simplest and probably the hardest to do: make sure you’re carving out at least 15 minutes daily to think about your world, what’s most important, and what you’re currently ignoring. Make sure, even if only in your own mind, that once you’ve examined these topics, you either put a first step on your to-do list, or you feel ok about relegating them to the back-burner of your consciousness once again.

My challenge to you right now is to grab a Post-it or scrap paper and write down one thing that is niggling at the borders of your consciousness. Why haven’t you dealt with it yet? Is it 1, 2 or 3? Once you have your answer, read through the above again for a good first step forward!

Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.

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