“I don’t understand. The deal was moving forward. My team’s reports said we were on track. I had lunch with their CEO last month, and everything felt solid.”
Andy was talking about a client who had just walked away from a major deal his team had been reporting as “progressing well” for months. He believed the relationship was strong based on all the status meetings, as well as a lunch he’d hosted where the client had been cordial and talked about the future.
As Andy’s executive coach, I helped him reflect on what had unfolded, and he realized that the warning signs had been there all along. He’d simply not seen them. The client’s procurement team had raised concerns about the implementation timeline, but these were downplayed in internal updates. When Andy conducted a review, his own sales engineering team acknowledged that they’d sensed the client’s hesitation, but didn’t think it important enough to flag it, assuming others senior to them would have a better view and make that call.
With the benefit of hindsight, Andy recognized that the client’s CEO had hinted at competing priorities during their lunch conversation. But Andy didn’t connect the dots at the time. He’d heard what he wanted to hear, that the deal was moving ahead, and had overlooked the warning signs.
The clues were there, like breadcrumbs, only Andy hadn’t followed the trail. One more question or moment of genuine curiosity, and Andy may have seen the fuller picture and been able to turn things around.
Andy wasn’t negligent. He is smart, experienced, and genuinely invested in the client relationship. Like many leaders, he relied on his experience. He hadn’t realized that the team around him, internal and external, had become a filter, not a lens, to the information he needed most.
The leadership highlights reel
The reality is that as leaders advance through their careers, information passes through more and more organizational layers before reaching them. Each layer creates its own filter. Marshall Goldsmith calls this “adding too much value” in his book What Got You Here, Won’t Get You There. In proving their own value, each person inadvertently alters the original message without realizing the impact.
If you ever played the telephone game as a child, you know how quickly a message changes when it passes through just a few people. Now imagine that game being played daily across your organization, except nobody’s laughing at the end.
It starts below your direct reports. The team beneath your team condenses, interprets, and adds their perspective to the data before it reaches the people who report to you. By the time the report is ready for your attention, you’re reading a version of reality that’s been through a professional game of telephone, except this version makes sense. The final report is well structured and tells a plausible story, and so you stop asking deeper questions.
Even when you do ask, your team has learned which questions you’ll raise. They’ve either included the answer in the report so you don’t have to ask, or rehearsed their answers in case you do. As a result, when you do ask a question and receive a confident reply, you move on.
Your team has learned what grabs your attention. Which ideas land. Which suggestions cause that little wrinkle between your eyebrows. Their goal is to iron out those wrinkles. Gradually, what reaches you becomes a curated version of reality, as everyone optimizes for your preferences without realizing it. The curiosity cycle gets shortened and we’re lulled into an increasing sense of certainty with which to make our decisions.
Cornelia Choe, who with Goldsmith cowrote The Panoramic Leader, calls this “perspective blindness”—seeing your part of the map and believing that’s the whole map. “The information, knowledge, and perspectives of the landscape that we need aren’t all in one place,” Choe told me during her appearance on my podcast People First! “They’re distributed in the minds of many different people.
“It’s important to understand these perspectives and bring them together so that we can fill in our blind spots,” she said. “In order to really understand different people, we need to create a relationship with them. Trust isn’t a given. We have to earn access to other people’s perspectives.”
Your relationships are a leadership intelligence system
What many leaders will assume, much like Andy did, is that the answer is to consume more information, more meetings, additional reports, or increasingly complex dashboards. But the problem was never the volume of information. It was the through which that information travels.
In my book, Cultivate: The Power of Winning Relationships, I present four relationship dynamics: Ally, Supporter, Rival, and Adversary:
- Allies are your “best friend at work.” They don’t just bring you news; they’re also willing to tell you the toughest messages that others may not. They’ll flag the potential issues before they derail the deal.
- Supporters may possess valuable insights but may not feel comfortable challenging your perspective—especially if your seniority means that your perspective is the HIPPO (Highest Paid Person’s Opinion) in the room.
- Rivals can often identify the weaknesses in your approach that other colleagues might overlook, and enjoy the devil’s advocate role.
- Even Adversaries offer perspectives that, while you may not agree with them, can provide information that strengthens your decision-making—if you choose to listen.
If you aren’t paying attention to the relationship dynamics around you, you can find yourself making decisions inside a bubble that feels like clarity, but isn’t.
That was where I met Andy. He didn’t lose the deal due to a lack of data. He lost it because he lacked an Ally, internally or externally, who could’ve said: “I think you’re hearing what you want to hear. Let me tell you what I’m actually seeing.”
Most leaders have built their careers on having answers, with a heady dose of self-confidence that grows from being right, and feeling like the smartest person in the room. It’s often what got them promoted. They recognize patterns quickly, connect dots in ways others miss, and move decisively. These are real strengths. But in a world that’s changing faster than any individual can track, yesterday’s pattern recognition can become today’s blind spot.
More connections aren’t the answer
This isn’t an argument for adding another dozen coffee meetings—more caffeine, more networking—to an already impossible calendar.
Instead, it’s about cultivating the relationships you already have in your network. It’s about understanding who you depend on for your success; which relationships provide the edge and challenge you need; and which have become comfortable or predictable, and as a result may be limiting versus broadening your perspective.
An easy first step is to pause and ask yourself: Whose opinion do you routinely seek out? Who challenges your thinking? Who might know something you don’t? And who have you stopped listening to because you’ve labeled them as difficult, or because they don’t see the world the way you do?
Each of these questions provides one additional moment to open up the information landscape that you are navigating.
Right isn’t the same as seeing
You can absolutely be right about what you see and still be missing half the picture. If I were to hold my hand up to you, you’d describe my (hopefully) long lifeline, the palm of my hand; and yet from my perspective I’d see my knuckles, the ring I wear. Both perspectives are right, but it’s only when we bring them together that we see the whole hand.
In an information-rich environment, the leadership advantage we all need to cultivate isn’t necessarily about knowing more, but from seeing differently. As Choe describes, a panoramic leader builds relationships, curiosity, and humility to uncover the perspectives that your own vantage point can’t reveal.
Who sees something you don’t, and when did you last ask them what they’re seeing?