Jon’s FAQs & Strategies
Real questions, real situations, and clear strategies to help you think bigger and take action today.
Contact Jon to GET UNSTUCK
Clarity Closes
Complexity feels impressive.
Clarity closes.
Simplify the message.
Say it in one sentence.
The AI Shift
Your next colleague may not be human.
This shift is already happening.
Conversations
Most conversations fail before they begin.
Not from what’s said.
From what wasn’t prepared.
Prepare the conversation.
Decide the outcome first.
Ask Better Questions
One of my clients kept “building rapport.”
Weeks passed. Great conversations. Zero deals.
Then they asked one direct question. Everything changed.
Here’s the reality about sales:
Rapport without direction is just hanging out.
Pros don’t sell harder. They ask cleaner.
When my clients make this shift, they:
– Ask better open-ended questions
– Listen more, explain less
– Keep control by staying curious
– Get clearer yes/no answers
– Close with less effort
Selling isn’t convincing. It’s asking. Then guiding.
Here’s an action step for today:
Next call or meeting, remove one explanation.
Replace it with one clean question.
Momentum follows.
Titles Expire. Values Don’t.
What Thomas Jefferson Quietly Taught Me About Brand, Soul, and Legacy
I read something recently that made me pause.
When Thomas Jefferson wrote his own tombstone, he intentionally left off President of the United States.
That wasn’t humility. It was clarity.
He chose to be remembered for his ideas, his values, and what he built—not the title that brought him status. It made me reflect on how often we shape our lives and brands around appearance instead of alignment.
Living authentically isn’t about being seen. It’s about being true.
When your actions match your values, your brand becomes quiet. Clean. Trustworthy.
So consider this:
-How do you lead when no one is watching?
-How do you sell—do people feel respected or pushed?
-How do people feel after spending time with you—steady or diminished?
-What do you protect when it costs you comfort or approval?
-If the title disappeared tomorrow, what would still be worth standing for?
Those answers tell the truth.
On Jefferson’s tombstone, he chose these words instead of “President”:
-Author of the Declaration of American Independence
-Author of the Statute of Virginia for Religious Freedom
-Father of the University of Virginia
No rank. No office. Just contribution.
Titles expire. Values don’t.
Most people don’t hit their limit
They stop at the first signal to slow down.
I see it in my work—and I catch it in myself too.
This one stuck with me.
Winging it feels flexible
It’s usually lazy preparation.
Decide your priorities before the day starts.
Decide first.
Then open your calendar.
Clarity beats effort. Every time.
Most people don’t fail from lack of effort.
They fail from unclear execution.
A new client shared how they avoided follow-ups for months.
Not because they didn’t care.
Because silence felt safer.
Didn’t want to seem pushy.
Didn’t want to “bother” people.
Then something clicked:
Every deal they lost
was lost to silence.
That awareness changed everything.
Here’s what no one tells you about sales:
Follow-up isn’t pressure.
It’s leadership.
Follow-up is the game.
The best salespeople don’t wait for perfect timing.
They create clarity.
They create a reason to call.
They bring value to every conversation.
When my clients fix this:
– Deals close faster
– Sales cycles shorten
– Ghosting disappears
Silence doesn’t protect relationships.
It quietly kills them.
The hardest decisions don’t look urgent.
They just keep coming back.
If it hasn’t gone away, it’s not solved.
What decision keeps tapping you on the shoulder?
Overthinking Feels Responsible
It’s usually avoidance.
You already know the next move.
Stop overthinking.
Call. Follow up. Ask.
Sales Matter
If sales matter, they get protected time.
Prepare Your Day
Reactive days don’t produce sales.
Top performers decide their day before it starts.
Prepare your day.
Or it will run you.
Did You Ask?
If you didn’t ask, you didn’t finish the job.
Opportunities Don't Disappear
They expire.
If you haven’t asked,
you haven’t earned the yes.
Ask for the meeting.
Who are you waiting on?
You're not stuck
You’re overloaded.
Too many inputs kill progress.
Action: Remove one thing today.
Plan Heavy?
If your plan feels heavy, it’s wrong.
Plans should create energy—not pressure.
Action: Reset before planning.
Calm First
Most people try to solve problems while anxious.
That never works.
Calm first. Decide second
The call you’re avoiding
is the deal you’re delaying.
You don’t need a better script.
You don’t need more confidence.
Pick up the phone.
Make the call before noon.
Most people don’t need motivation.
They need clarity.
When everything feels important, nothing moves.
Clarity creates momentum.
Action: What’s the one decision you’re avoiding?
The best leaders aren’t faster.
They’re clearer.
“Jon, how do I think bigger every day?”
Your thoughts are the first place your results take shape.
They set the tone for getting UNSTUCK and thinking BIG.
Here is a simple daily system:
a THOUGHT AUDIT that shifts your mindset and your momentum:
Ask yourself these 3 things:
– What’s one thought I need to release?
(the one that holds you back from getting UNSTUCK)
– What’s one thought I need to elevate?
(gets you thinking BIG)
– How would my day change if I led from that elevated thought?
When you upgrade your thinking, you upgrade your outcomes.
What thought are you releasing, and what thought are you elevating, right now?
THINK, SELL and LEAD BIG(GER)!
JD
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I stay ready when things change?”
The best time to build your Plan B is while Plan A still works.
Keep sharpening your edge to THINK BIG:
-Learn new skills
-Grow your network
-Stay curious and adaptable
Plan B isn’t fear. It’s freedom.
What’s one thing you’re doing right now to future-proof yourself?
THINK, SELL and LEAD BIG(GER)!
JD
Jon, how do I become a better salesperson… without pushing so hard?
In sales — and in life — most people try to be Luke Skywalker.
They want to be the hero. They want the win.
But the real power comes from being Yoda — the guide.
Your clients already carry their own story, their own challenges, their own moment of truth.
Your role isn’t to dominate the scene… it’s to illuminate it.
You guide by asking grounded, thoughtful questions. You guide by listening for what isn’t being said.
You guide by helping someone see the path that’s already inside them — they just haven’t slowed down enough to notice it.
This isn’t selling. This is presence. This is alignment. This is leadership.
When you show up as the guide — calm, clear, steady — the call transforms.
The energy shifts. People open up. And trust grows naturally.
Stop trying to “close.” Start trying to center the conversation.
Yoda said it best: “A Jedi uses the Force for knowledge and defense, never for attack.”
Sales works the same way.
Guide with clarity. Guide with curiosity. Guide with intention. The results follow.
What’s one moment when you realized you were guiding — not selling?
THINK, SELL, and LEAD BIG(GER)!
JD
“Jon, how do I stay calm under pressure?”
Reaction is instinct.
Response is leadership.
Count to ten.
Pause before you reply.
You’ll say less, mean more, and lead stronger.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I scale without burning out?”
You can’t scale what you refuse to let go of.
Delegation isn’t giving up control — it’s creating capacity.
Ask yourself:
-What can I delegate today?
-Who can I trust to take it off my plate?
-How can I use that freed-up time to prospect, lead, or grow?
4 minutes/day saved = 24 hours/year
16 minutes/day saved = 96 hours/year
32 minutes/day saved = 192 hours/year
What’s one task you could delegate today to free up your time?
“Jon, what books are you reading right now?”
-The Singularity Is Nearer – Ray Kurzweil
Kurzweil is one of the world’s leading futurists and inventors, known for accurately predicting major technology shifts.
I’m reading it to understand how AI and exponential technologies will transform business so I can stay ahead & help my clients do the same.
-The LinkedIn Edge – Jeb Blount & Brynne Tillman
A tactical, real-world guide to turning LinkedIn into a relationship and revenue engine.
I’m reading it to grow my business using the tools and power of LinkedIn—then teach others how to do it even better.
-Hardball: Are You Playing to Play or Playing to Win? – George Stalk & Rob Lachenauer
A bold playbook on how great companies compete fiercely and think strategically to dominate their markets.
I’m reading it because David Senra talks about how so many founders he studies have read it—and I want to see why it keeps showing up in the playbook of legendary founders. Founders Podcast
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I make meetings shorter and stronger?”
Every 4 minutes saved/day = 24 hours/year/person.
Shrink the room, sharpen the work:
90 → 60
60 → 30
30 → 20
15 → 10
Always:
- Clear agenda
- Clear purpose
- Clear next steps (owners + deadlines)
Meetings should create clarity, not drain time.
How do you keep meetings short — and powerful?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how should I be using AI in my business?”
As a business coach, I see it firsthand — Leaders who use AI to simplify, systemize, and strategize are freeing up time to think bigger, move faster, and be more productive.
⚙️ Mastering AI takes intention, but the payoff in clarity, speed, and focus is massive.
⚡ AI isn’t always replacing people. It’s challenging us to elevate how we think, lead, and create — and that’s where the real potential gets unlocked.
🚀 The opportunity isn’t about how smart AI becomes — It’s about how we use it to amplify our productivity, leadership, and results.
👉 How are you using AI to grow faster, lead stronger, and think bigger?
“Jon, how do I take the lead without controlling everything?”
Real leadership starts where ownership begins.
If you don’t own the process, you can’t lead the outcome.
When data changes, systems shift, or processes evolve — someone has to take charge.
Not to control — but to clarify.
Because every data point affects something else.
Before you move forward, ask:
-Who owns this?
-What changed and why?
-Did we communicate it clearly?
Leadership means creating the flow before chaos happens.
Be nice. Be firm. Be clear.
Then roll out the new standard — and inspect what you expect.
Where in your business do you need to take ownership right now?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I actually use data to lead better and SELL more?”
Your data is talking.
Are you listening — or just reacting?
Data doesn’t lie — but it also doesn’t lead.
It’s your job to interpret it, prioritize it, and forecast with it.
Ask yourself:
-Is this data lagging or leading?
-What story does it tell?
-Are we painting the right picture with it?
The best leaders use data not as a mirror, but as a windshield.
It’s not about where you’ve been — it’s about where you’re going.
Own your data.
Drive your direction.
What’s one metric you’re using right now to drive — not just track — growth?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I actually hit my goals?”
I get this question all the time.
Here’s my answer:
Work Backwards, Move Forward.
Stop planning forward.
Start planning backward.
If you’re planning forward, you’re already behind.
The best leaders start at the finish line.
They ask:
“What do I want this to look like by December 31, 2026?”
Then they build backward.
Year → Quarter → Month → Week → Day
Until every move has an action plan and meaning.
That’s how you turn vague goals into specific and measurable outcomes.
Because every task needs three things:
– An owner
– A specific and measurable result
– A deadline
Airplanes don’t have rearview mirrors for a reason
They’re built to move forward.
So is your business.
If January 1st were tomorrow…
Would you be ready?
Work backward to move forward.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, why do some people spot opportunities faster than everyone else?”
It comes down to Re-Perception — the ability to notice what others miss and read the moment with clarity.
In an AI-driven world where speed keeps rising, this becomes a real advantage.
Not more noise. A sharper view.
The people who move ahead are the ones who see differently, not the ones who hustle harder.
Three ways to strengthen your Re-Perception:
1. Pause before you respond. Ask: What’s the signal here? What am I overlooking?
2. Shift the angle. Step back for perspective, then lock onto the detail that changes the outcome.
3. Use AI as your extra lens. Let it challenge assumptions and surface patterns you’d normally skip.
Re-Perception keeps you sharp, relevant, and ready for what’s next.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I actually prompt AI the right way?”
I get this question every day.
Q: Prompt engineering sounds complicated. What am I missing?
A: It’s simpler than it looks. Treat AI like a top performer you just hired — it needs direction, not magic.
Q: So what do I actually tell the bot?
A: Three things:
-Context — everything the bot needs to know to do its job well.
-Task — exactly what you want it to do. Clear, specific, and outcome-focused.
-Format — how you want it delivered.
Q: Why do my bots feel generic?
A: Most people under-direct AI. Vague inputs = vague outputs. Clear roles and rules turn AI into a teammate, not a tool.
Q: What’s one prompt I can use today?
A: “Act as my ___ and give me the fastest, simplest way to solve ___.”
Q: What’s the upside of doing this well?
A: You unlock the 90% of power most people never tap — faster ideas, cleaner decisions, better outcomes.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I build momentum when results feel slow?”
Big wins make headlines.
Micro wins build pipelines.
Define what winning looks like at every stage:
-A call that opens a door
-A relationship that builds trust
-A client who says, “You get me.”
Small wins compound.
Momentum builds quietly — then explodes.
What’s one micro win you can celebrate today?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I stay relevant in an AI world?”
AI can automate everything — except connection.
Technology moves fast. Trust moves slower.
And that’s your edge.
Be real-time. Be curated. Be human.
Walk the floor. Go see your clients. Shake hands. Build relationship capital that no algorithm can replicate.
Because when everything feels automated, the personal touch becomes priceless.
How are you keeping the human touch alive in your business?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I bring more CLARITY into my business for 2026?”
Clarity wins. Noise slows everything.
Your real competitor next year?
The distracted client — overwhelmed by news, markets, and life.
You can’t change their distractions.
You can make your message unmistakably clear.
Sharpen your clarity — sharpen your impact:
Start with three essentials:
-One word you want to be known for
-One place your sales pitch needs clarity
-One move you’ll make to grow your brand
Clarity isn’t a tactic.
It’s an advantage.
Where will you bring more clarity today?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I stay consistent?”
Consistency looks like nothing is happening… until everything changes.
It’s not about intensity. It’s about showing up when it’s boring, quiet, and unseen.
Ask yourself:
-What’s the smallest action I can repeat daily?
-What rhythm can I build that won’t break under stress?
-What’s one metric I can track to stay accountable?
When you stay consistent, you multiply your momentum.
One quiet day at a time becomes massive progress no one saw coming.
What’s one tiny action you can commit to every day — no matter what?
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, how do I stay motivated through rejection?”
100 calls. 100 No’s. One Yes.
That’s not failure — that’s math in motion.
Gamify your grind.
Track your No’s. Celebrate progress.
Every rejection brings you closer to the BIG win.
When you remove emotion, you build rhythm.
And rhythm beats luck — every time.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, when’s the best time to prospect?”
When everyone else slows down, that’s your moment to accelerate.
December isn’t a quiet month — it’s gold.
Clients are planning, reflecting, budgeting — and picking up the phone.
-Call the people who told you “no.”
-Call all old proposals from the past three years — minds change.
-Reconnect with the people who “weren’t ready” — and meet them in person.
While others coast, you build momentum.
And the momentum you build in Q4 becomes the revenue you collect in Q1.
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, why do I need to grow my sales skills in an AI world?”
Because everything is sales — influence, clarity, and connection.
AI can support you, but it can’t replace trust, presence, or the way you move people.
Ask yourself:
-Am I communicating value clearly?
-Am I asking for the next step?
-What follow-up have I avoided?
-Am I showing up as a guide — or hoping they figure it out?
Sales isn’t pressure.
It’s clarity and service.
Strengthen your skills and every part of your business grows.
Want to get sharper?
Start here: https://lnkd.in/eJSQ5zjZ
THINK, SELL and LEAD BIG(GER)!
JD
“Jon, what’s a great way to grow my business quickly?”
Meet 100 people in 100 days.
Then repeat it every 100 days.
It’s the simplest, most reliable growth engine there is. Business grows through conversations — not waiting.
How to do it:
-Coffee meetings: Fast, easy, low cost.
-Go to their office: Build rapport and respect.
-Invite them to yours: Position yourself as a resource.
-Use lunches selectively: Save them for deeper connections.
This isn’t about pitching — it’s about connecting.
More conversations = more opportunities, more referrals, more momentum.
Most people won’t do this.
The ones who do — grow. Fast(er)
THINK, SELL and LEAD BIG(GER)!
JD
Clear thinking beats busy effort every time.
Question: What actually matters this week?