The Coach Who Changed How I Lead | A Tribute to Ola Sage
A reflection on independence, leadership, and the coach who taught me how to listen better, ask deeper questions, and build something bigger than myself.
When a Simple Gesture Turns Complicated
Two weeks earlier we had catered breakfast for a team of engineers. Through some breakdown in communication, the delivery arrived later than it should have.
The team still ate the meal.
But the timing was not what it was supposed to be.
So we did what felt like the right thing.
We refunded the entire $1,800 order.
Not a partial credit.
Not a discount.
A full refund.
And we told the customer we would gladly take care of a future meal as a gesture of goodwill.
It felt like the right move. The kind of thing that builds a relationship.
A few days later, an email came back.
It was not a small follow-up meeting.
It was a request for an all-hands lunch for 225 people with multiple entrée options.
Sesame chicken.
Bacon wrapped meatloaf.
Chicken alfredo.
Pot roast.
A vegan option.
When I read it, my stomach dropped.
Not because of the menu.
Because of the size of the request.
We had already refunded the entire breakfast. The team had eaten the food. We had tried to make it right.
And now the follow-up ask was a full lunch for 225 people, roughly $5,000 worth of catering.
With business already slow, I felt it immediately.
A gut punch.
The kind you feel deep in your stomach.
Part of it was the money.
But part of it was something deeper.
Right now, losing a customer who might spend $2,000 on a future event feels existential. When business is moving normally, you absorb a moment like this and keep going.
But during a slow stretch, every relationship feels fragile.
Losing one customer suddenly feels bigger than losing one order.
And suddenly I was staring at a choice.
Acquiesce to a request that clearly felt like too much and maybe keep the customer.
Or set a boundary and likely lose the relationship altogether.
That is not a comfortable place to sit.
We responded honestly.
We told her we would gladly offer a $300 credit toward a future order, but a meal of that size was more than we could reasonably offer.
It was not an easy message to send.
But it felt like the right boundary.
It no longer felt like we were repairing a relationship.
It felt like generosity had been interpreted as an opening.
You try to do something kind.
And the response makes it feel like the money was left on the bedside table.
Transaction complete.
Now get out.
When Generosity Is Met With Too Much Taking
Over the years I have started telling my kids something simple about how the world works.
Try to find other givers.
Because you are a giver.
When givers find each other, good things tend to happen. Trust grows. Relationships grow. Life feels lighter.
But when givers mix with takers, it can be a dangerous combination.
The giver keeps giving.
The taker keeps reaching for more.
Moments like this are reminders.
Generosity is still the right way to move through the world.
But it helps to have a boundary ready in case your generosity is met with too much taking.
I have written before about the importance of saying no with empathy. Moments like this are exactly where that lesson becomes real.
“Know what’s enough. Build what matters.”
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