“I’ve already brought it up three times. Am I supposed to bring it up again?”
My client was starting to think the issue was him.
Maybe he wasn’t seeing clearly. Maybe his boss thought he was focused on the wrong target. Or worse, maybe he was becoming an annoying, squeaky wheel, the kind people roll their eyes at, just not to your face.
The silence, intentional or not, had become a verdict.
They’re not ignoring you, they’re not here.
Senior leaders live six months to a year ahead. It’s the job. Setting direction requires it.
It can be hard to see into the future and still relate to what is happening in the present. Sarah Connor in Terminator 2 was put into a mental institution because of it.
Leaders don’t get locked up for it, but they often struggle with the same issue. Sometimes without even knowing it.
Even as executives work through scenarios, review trends, and hypothesize outcomes, they don’t get a pass on the day-to-day. That’s also part of the job. The problem is when they confuse the future and the present.
Too many executives overestimate their context-switching abilities and underestimate the negative impacts of the cost. They think they are simply juggling multiple realities, but really they can only hold one at a time. They miss the present while contemplating the future. And they color the future with their present concerns.
Your boss isn’t withholding a decision. They’re in a different year, and the version of them in the room is only partially listening.
The truth, from inside the other chair.
When I went into future-planning mode, I would become completely immersed. Strategic planning can be all-consuming, especially if you want to be thorough and collaborate as an executive team.
I would all but ignore my current operations, relying upon my deputies to lead. Unless it was an emergency, I didn’t have time.
Things I would have normally caught and properly addressed festered or ballooned. Underperforming employees didn’t get the feedback they needed. A large client who needed nurturing almost churned.
The one that stung the most? Deferring a deep assessment of our revenue engine. I knew it was important, but we were hitting targets. Had I dug deeper, sooner, I would have realized we had one star, but the rest of the team was floundering. We didn’t have a repeatable sale. Our business relied on one person to keep showing up.
I only realized the issue well into the next year, the one where we were supposed to grow exponentially. Instead, we had to rebuild from the ground up.
The worst part wasn’t the miss. It was the team members who had raised flags, more than once. But I pushed them aside while I lived in a hypothetical, rosy future.
I thought I was being the futurist leader when I was actually distracted and disconnected.
I wasn’t deftly juggling two realities. I could hold only one at a time, and by dropping one, I dropped the other. My team didn’t just suffer the delay alongside me; they saw a leader who they were no longer sure they could trust.
Why the gap costs more than delay.
The cost of the disconnect starts with perspective, but it can quickly grow into confusion and ultimately distrust. It’s the kind of team stress with no release valve: the team can see the gap growing, but their leader doesn’t even know it exists.
If you’re working with a leader like this, you know what it feels like. You bring up topics that should register with weight, and you get a cursory nod. You push for a controversial change with emotion, and you are told things are OK, now’s not the time.
The reaction is real, but it’s not correlated to what you said. It’s connected to another time and place, one that you have no context for, and no idea how it’s changing the conversation.
It means decisions are delayed, poorly executed, or just outright ignored. Some never needed prioritizing, but if you’re a senior, trusted leader bringing up the same topics more than once, it’s demoralizing to feel unheard.
A path forward with more clarity and coherence.
I’m always a fan of simply saying the thing. Every leader I know who has done this has built a stronger relationship, not a weaker one.
When my client raised his concerns for the fourth time, he did it with a question. “Am I not seeing something clearly? Why does it feel like this issue is a high priority for me, but not the leadership team?” It had taken five months, but his boss finally ran it up the chain and got it resolved.
The result wasn’t just closure, but confidence. He had proven something to his boss that acquiescence would have never conveyed.
Here are four actions that can help your boss move past indecision or a non-answer.
Ask what time zone they’re in. Plainly. “Are you in planning mode right now? When do you come out?” Most people never ask, and most leaders will answer.
Timestamp your asks. Lead with the horizon before the content — “this is a this-quarter decision” or “this is a next-year question.” Route yourself into the reality they’re standing in.
Raise the pattern, not the issue. “I’ve brought this up before. I want to understand whether it’s not landing or it’s not a priority.” Never assume. Name your fear not because you want sympathy, but because you seek understanding. Sharing that it feels like insubordination, or like admitting you’ve been keeping score gives your boss permission to tell you what is actually true.
Bring both horizons before you’re asked. Map the short-term and long-term implications yourself. You stop being the person raising a present-tense problem and become the person thinking in their time frame.
The gap was never about you, but you can help close it.
This is your reminder that your boss’s actions aren’t always about you or what you did or said, especially when they are in future mode.
They won’t always remember to share their context. And you don’t have to wait to ask.
The gap wasn’t caused by you. But you can help your boss see it and close it together.
May you lead without limits,
Kathy
P.S. If you know of a leader who needs this reminder, please consider sending it to them. And if you enjoyed this post, consider giving it a ❤️. It’ll help me reach more leaders — thank you!