Recently, my son asked if he should take a job.
I didn't have the perfect answer.
But I knew this:
Forward beats frozen.
Clarity rarely comes before the first step.
It usually comes because you took it.
Keep moving.
#BillsWeeklyWisdom#Leadership
My daughter is in Brazil on a mission—near where I was at 19.
It’s hard: new country, new culture, difficult language
She said: I chose this hard.
We can’t avoid hard
But we can choose what our hard is in service of
Choose your hard
Then get to work
#BillsWeeklyWisdom
Saw this shirt today:
“The worst days in the arena are always better than the best days in the stands.”
I’d rather build than critique.
Lead than observe.
Create than consume.
The arena isn’t comfortable.
That’s exactly why it’s worth being in.
#BillsWeeklyWisdom#Leadership
I've loved selling since my first lemonade stand
Not for money
Because of value
Sales isn't convincing one to buy something one doesn't need
It's solving problems, achieving outcomes, and recognizing value
Whether you know it or not, you're in sales too
#BillsWeeklyWisdom
The first question of AI was:
"Can we do it?"
The next question is:
"Should we?"
More specifically:
Where does AI create enough value to justify its cost?
Technology gets attention.
Economics determines adoption.
#BillsWeeklyWisdom#AI#Leadership
Trust in AI isn’t a technology problem.
It’s a leadership problem.
People don’t need AI to be perfect.
They need to understand it, trust it, and remain in control.
AI can generate outputs.
Humans still own outcomes.
#BillsWeeklyWisdom#AI#Leadership
AI optimizes things for speed:
faster decisions, faster responses, faster execution.
But speed can become a tax on judgment
Good judgment often requires reflection, context, patience, and restraint.
Speed scales execution.
Judgment determines direction.
#BillsWeeklyWisdom
A favorite greeting is the Zulu phrase:
“Sawubona” — “I see you"
Real leadership is seeing people:
their effort, ideas, potential, and humanity
Too many feel invisible at work and in life
I see you. I’m grateful for you & always here.
#BillsWeeklyWisdom#Leadership#Empathy
Insurers moving to exclude some AI-related claims from coverage is a much bigger story
Companies rushing to deploy AI
Insurance markets may already be signaling risks aren’t fully insurable yet
AI generates outputs
Companies still own outcomes
#BillsWeeklyWisdom#AI
A conversation last week
A founder—sharp, prepared, building something real
But what stood out most wasn’t the idea
It was his attitude
He didn’t have all the answers.
He had curiosity and willingness to learn
That’s what drives success
#BillsWeeklyWisdom#Leadership#Startup
AI transformations don't fail because of bad tech.
They fail because of broken trust.
Would your team tell you if it was failing?
Start there.
#BillsWeekWisdom#AI#Leadership
AI makes information abundant
Research, analysis, and ideas now seconds away
Which means clarity becomes rare
Teams rarely fail from lack of data
They fail from lack of direction
With much info, clarity becomes the leadership advantage
#BillsWeeklyWisdom#Leadership#AI
Worked with enterprise AI since 2005
AI makes us more productive-research/analysis/ideas
But most important were never those tasks-
Judgment
Accountability
AI generates options
It cannot own outcomes
AI won’t replace leaders
It will expose who aren't leading
#AI#Leadership
Woke up Saturday to war in the Middle East…on top of so much else
It’s heavy
Focus on what you can control — your work, your goals, your effort, your emotions
Don’t let what you can’t control control you
Control your inputs
Own your response
#BillsWeeklyWisdom#Mindset
My son spoke at a service about consistency.
He said that change doesn’t come from big moments.
It comes from doing things over and over.
Discipline isn’t loud.
It’s consistent.
Small actions. Repeated.
That’s where real change is
#BillsWeeklyWisdom#Consistency#Discipline
I’ve made a lot of mistakes in life and in my career—too many to count.
Mistakes happen. Life is meant to be lived.
The real choice comes next:
learn from it… or repeat it.
#BillsWeeklyWisdom#Growth#Leadership
Life builds resilience in contrast—joy and loss. 11 years ago, my daughter was born; the next day, my father passed.
These events define how I lead: with empathy, presence, and humility to embrace the hard parts, not just the easy ones.
#BillsWeeklyWisdom#Resilience#Leadership