“I looked into your glass to see if you had enough.
You looked into my glass to make sure you had as much.”
That single distinction explains more about business, sales, and relationships than just about any metaphor I could share. Though I didn’t know it at the time, I learned this important lesson from my grandfather, Leif, with a fishing rod in my hands.
Grandpa Leif loved to fish. Loved it. He went at least twice a day, sometimes more, and even in the rain. It wasn’t unusual for him to head out early in the morning and then again in the evening, like the river itself was calling him back. When school was out for summer, and I wasn’t tied up with chores on the farm, he would often ask me to come along.
Grandpa wasn’t really a talker. We didn’t fill the air with words. We just sat together, or walked the riverbank together, with lines in the water. Catching fish seemed almost irrelevant. What mattered was that we were there. Together.
Looking back on it now, I realize how much he understood about relationship building without ever saying a word about it. He wasn’t trying to get something from me. There was no preconceived outcome. He was simply present. And that presence said: This time matters. You matter.
That mindset – the quiet decision to value togetherness over personal gain – is rare. And it’s the same mindset that separates transactional relationships from meaningful ones, especially in sales and business.
In sales, we like to focus on tactics and closing strategies. But beneath all of that is a question every prospect is subconsciously asking: Are you here to make sure I’m okay, or are you here to make sure you get yours?
The best salespeople I know, behave a lot like my grandfather on those fishing outings. They slow down. They listen more than they speak. They’re paying attention to what’s not being said. They look into the other person’s glass first to see, do they have enough clarity, enough confidence, enough support to actually succeed?
On the other end of the spectrum are the people constantly checking their glass, and yours, wondering: Am I winning? Am I ahead? Am I getting as much as they are? That mindset turns every interaction into an unnecessary and unfortunate competition.
What’s ironic is that the people who focus on making sure others have enough almost always end up with more – more trust, more referrals, more long-term business. It applies to partnerships, teams, friendships, and even families.
Think about the people you feel most comfortable with. The ones you can exhale around and be yourself. Odds are, they’re not keeping score. They’re not watching to see if you’re getting more than they are. They’re watching to see if you’re okay. That’s the same feeling I had sitting beside my grandfather – no pressure, no ledger, just shared presence.
Now think about the opposite. Relationships that feel tense or draining often have an invisible scoresheet running underneath them. Who owes whom? Who’s up? Who’s down? Those relationships might survive for a while, but they’re built on a bed of sand.
This is why the type of people you work with, and choose to work with, is key.
You can have the best product, the smartest strategy, and the most aggressive growth plan, but if you build with people constantly checking your glass to make sure they have more, you will always feel slightly on edge. And it’ll suck the joy right out of you.
On the other hand, when you intentionally surround yourself with people who are looking to see if you have enough – enough support, enough credit, enough margin – it’s different. Hard conversations become easier. Growth becomes a shared goal and experience.
The real work, in sales and in life, is learning to spot the difference. Listen to the questions people ask. Notice whether curiosity flows outward or inward. Pay attention to how they behave when there’s nothing obvious to gain.
Then choose accordingly.
My grandfather never taught me this with spoken advice. He taught me with time. With presence. With a fishing line cast into still water and no expectation of return.
I miss him. And over time and life experience, I’ve learned a lot about who he was. I’ve learned the lesson he lived masterfully – that being with someone, fully and generously, is worth more than anything.
In business and in life, the goal isn’t to make sure you always have as much.
It’s to seek out and choose people who care that everyone at the table has enough.
Until next time,
Kenyon Gleason
NASGW President