1:1 Leadership Coaching
with Jon Dwoskin
Jon helps you stop managing problems and start leading what drives real business results.
Contact Jon to GET UNSTUCK
Are you…
Struggling to influence and align your team?
Not sure how to find your voice?
Making decisions but not seeing progress?
Leading, but feeling like you’re the only one doing the work?
Jon helps you cut the clutter, focus on what drives progress, and lead so your team follows consistently.
Working with Jon was a game-changer for me and my business.
As a President of my business and a benefits advisor myself, I had the knowledge—but not the strategy—to truly grow and differentiate myself in a crowded market.
Jon helped me see my value clearly, refine my messaging, and build a marketing and outreach strategy that actually worked.
Jason, President & Benefits Advisor
Jon helps you lead effectively.
Strategic Leadership
Clarify direction, set priorities, and lead people with purpose, not pressure.
Team Alignment
Run better meetings, delegate clearly, and hold your team accountable without micromanaging.
Operational Clarity
Focus on high-impact activities and build structure that scales with you.
Inside Jon’s Leadership Coaching
Eliminate meeting fatigue, stalled decisions & lack of clarity to lead with intent and precision.
- Improve how you run meetings and manage time
- Lead performance conversations with clarity and purpose
- Sell your ideas with persuasive presentations
- Get unstuck on decisions with real-time support
- Build trust and influence at every level
- Identify your leading activities & cut what’s slowing you down
- Get fresh ideas when you need them most
How it Works
Step 1: 90-Minute Deep Dive
A focused kickoff session to evaluate your leadership strengths, team gaps, and operational bottlenecks.
Step 2: Weekly or Bi-Weekly Coaching
Option 1: One 15-minute session per week
Option 2: Two 30-minute sessions every other week
Step 3: Daily Support Access
Call, text, or email Jon anytime with a guaranteed same-day response.
Jon’s Guarantee
- Guaranteed value on every call or you don’t pay.
- No contracts – month-to-month investment.
- Same-day responses to all calls, texts, or emails.
With Jon leading our sales meetings and the 1-1 time he spends with them, it has freed up my time to do mission critical work the company needs as a principal of the business.
It has also kept our sales team on track, growing their pipelines and keeping their sales skills sharp.
Jeff, Principal
Since I started working with Jon, I have become much more organized, efficient, and focused.
Every week, I learn new tips and strategies to implement into my routine.
Our last 15-minute call made me at least $500k in potential commissions.
Charles, Sales Associate
I’ve been a marketer for 28 years and I can honestly say I’ve gleaned more from you in the last 2 years than I have in my whole career.
Thank you for believing in me, pushing just enough, but not too much to make me more
efficient and better.
You bring out the best.
I can’t thank you enough.
Ginger, Sales Executive
THINK Business & Sales: Pick. Up. The. Phone. With Gabe Lullo
Always Be Prospecting Today on THINK Business, I sat down with Gabe Lullo, CEO of Alio, a company that makes 11 million cold calls a year. Yes, 11 million. We dug into something every business needs to...
3 Must-Read Books to Grow Your Business and Life: Smart Brevity, Think Faster, Talk Smarter, and Atomic Habits
If you’re feeling stuck in your business or personal life, it’s time to think big and take actionable steps toward growth. As a business coach, I’ve seen the power of small shifts and strategic thinking transform careers, companies, and lives. Three books I...
THINK Business & Sales: Following Your Talent with Charlie Cooper
Following Your Talent: A Conversation with Duke Photographer Charlie Cooper Most people know their talent long before they have the courage to follow it. Charlie Cooper — Duke sophomore, award-winning...