Leadership isn’t developed by completing a curriculum. It’s developed by applying new thinking and behaviors to the real challenges a leader faces every day.
HuntJack combines guided discovery, coaching, practical tools and real-world application to help leaders become more intentional about how they lead themselves, develop others and influence the business.
What You Get With Tom
Direct Access
Every engagement is directly with me.
Guided Discovery
Development starts with the leader’s priorities—not a predetermined curriculum.
Practical Application
Real business and leadership challenges become the classroom.
Tools When They Matter
Resources and frameworks are introduced when they support a real development need.
You didn't get to where you are by accident. But the skills that made you a strong individual contributor — or even a good early-stage manager — aren't the same skills that grow a team, attract talent, or scale a business. The gap is real, and it widens every year you don't close it.
The organization can only grow as fast as the leader grows. If your decision-making, communication, or strategic thinking has plateaued — so has your team's output. Leadership isn't the nice-to-have. It's the bottleneck.
Most executive coaches apply the same program to a CFO, a regional manager, and a small business owner. The result: everyone gets the same advice and sees mediocre progress. Your challenges are specific. Your coaching should be too.
You've probably read the leadership books. You walked away energized — and six weeks later nothing had changed. Understanding isn't transformation. What changes behavior is accountability, application, and a coach who remembers what you said last month.
Tom Sheffield spent over 30 years in corporate leadership — from the ground floor to senior positions at the state, national, and global levels. He didn't read about organizational dynamics in a textbook. He navigated them, built teams through them, and made decisions under the same pressures you face now.
When Tom coaches you, he's drawing on lived experience — not a certification program. His approach is education-first: he wants you to understand why a certain decision-making framework works for your personality and your organization, not just hand you steps to follow until the next crisis catches you off guard.
"Leadership is the lid. You can't build a team that performs beyond the level of the person leading it. My job is to raise your lid — and help you understand why it was there in the first place." — Tom Sheffield, HuntJack Consulting
Whether you're running a growing small business or managing a division in a larger organization, the leadership gap is the same. The context is different — Tom's approach adapts accordingly.
You built the business. Now you're managing people — and nobody prepared you for that part. Tom helps owners transition from doing the work to leading the team that does the work, without losing what made the business great in the first place.
You've been a solid manager. The next step — VP, C-suite, or founder — requires a different kind of thinking. Tom's coaching helps you close the gap between where you are and where the role demands you to be.
Turnover is high. Communication is off. Performance has plateaued. Most team problems trace back to a leadership dynamic — not a people problem. Tom helps you diagnose which, then fix the root cause instead of the symptom.
Stepping into a new role — new company, new scope, new expectations. The first 90 days matter most. Tom helps you navigate the transition, build credibility quickly, and avoid the costly leadership mistakes that are especially common in new environments.
Development doesn’t always require the same hat.
Sometimes the best response is a question. Sometimes experience can shorten the learning curve. Sometimes a practical tool helps. And sometimes expectations simply need to be clear.
Effective development means knowing which approach the situation requires.
Every leader’s situation is different. Rather than beginning with a predetermined curriculum, development starts with the leader’s role, business priorities, challenges and goals.
Stop reacting to what's in front of you and start leading from a position of clarity. Tom helps you develop the discipline to think three steps ahead — and the frameworks to actually apply that in a busy organization.
Great leaders don't just manage — they move people. Tom works on how you communicate upward, downward, and laterally so your ideas gain traction and your team executes with conviction rather than compliance.
Every leader faces decisions with incomplete information and real consequences. Tom builds your decision-making muscle for precisely those moments — so you act decisively without recklessness and thoughtfully without paralysis.
The people who surround you determine your results. Tom helps you build hiring instincts, develop the people you have, and create a culture where top performers actually stay — and underperformers are addressed honestly.
Reorganizations, market shifts, team turnover, strategy pivots. Change is constant and most leaders handle it reactively. Tom coaches you to lead through uncertainty in a way that steadies your team instead of amplifying their anxiety.
Whether you're targeting a promotion, preparing for a new role, or figuring out your next chapter, Tom helps you map the path clearly — and then builds the capabilities you need to walk it confidently.
No intake forms. No cohort onboarding. Just a direct path from conversation to coaching that actually sticks.
30 minutes with Tom. He listens to your current situation — your role, your team, your sticking points, your goals. You walk away with more clarity than you started with, even if you decide coaching isn't the right fit right now.
Based on what Tom hears in the discovery call, he designs a coaching engagement around your specific leadership gaps, goals, and timeline. No generic program — a customized approach that addresses what's actually holding you back.
Regular one-on-one sessions with Tom, plus real accountability between them. Tom tracks what you're working on, follows up on commitments, and adjusts the approach when the market — or your team — changes on you.
Tom's free discovery call isn't a sales pitch with a soft close. It's a real conversation about where you are and where you want to go. Most leaders leave with a clearer picture of their leadership gap — whether they hire Tom or not.
Same-day appointments available · M–F 9 AM–5 PM EST
Not vague "confidence" or "clarity." These are the specific, observable changes clients describe after working with Tom.
You stop second-guessing every call. You have a process for making decisions under pressure that doesn't rely on gut instinct alone — and you can explain the reasoning clearly to your team.
The constant supervision, the follow-ups, the nagging — replaced by a team that understands the vision, owns their piece of it, and delivers because they want to. That's what leadership at the next level actually feels like.
Whether you're building toward a leadership transition, a new role, or just a sustainable pace that doesn't cost you your health — Tom helps you see the path clearly and build toward it on purpose rather than by accident.
"Tom's coaching cut through the noise. He's been where I've been — and he speaks from experience, not theory. I finally felt like I was getting advice from someone who actually knew what it was like to lead under pressure."
"Working with Tom was different from any consulting or coaching I'd experienced. He challenged the way I was thinking, not just the tactics I was using. Six months later, my team is stronger and our revenue reflects it."
Tom is direct about this: not every leader is the right fit for his coaching. Here's how to know before you book a call.
✅ This Is Right for You If…
You're open to being challenged on how you think, not just how you act
You want direct feedback — not validation — from someone with real experience
You're willing to do work between sessions, not just talk during them
You recognize that your current leadership approach has a ceiling
You value education over prescription — you want to understand, not just follow steps
⚠️ This May Not Be Right If…
You're looking for a coach who will agree with you and affirm your decisions
You want a quick fix — 3 sessions and a different team dynamic
You believe the problem is entirely external — the market, your team, your boss
You're not willing to be held accountable to what you say you'll do between sessions
You want a coaching program with a set timeline and predetermined milestones for everyone
Most executive coaches bring a certification and a coaching methodology. Tom brings 30+ years of having been the person you're trying to become — from entry-level roles all the way to senior leadership at the state, national, and global level. When he coaches you through a high-stakes situation, he's not guessing what it feels like.
Certification programs teach coaching methodology. Tom brings 30+ years of actually being a senior leader — from blue-collar entry roles to state, national, and global-level corporate positions. When you're navigating a high-stakes decision, a difficult team dynamic, or a leadership transition, Tom's coaching comes from having lived those moments, not having studied them. His education-first approach means you leave each session understanding the why behind the guidance — which is what changes how you actually lead when Tom isn't in the room.
At most executive coaching firms, you meet the lead — and then get assigned to an associate coach who delivers the actual program. With Tom, every session is one-on-one with Tom directly. There's no handoff, no junior coach with six months of experience, and no standardized cohort program that applies the same milestones to every client. Your coaching engagement is built around your specific leadership gaps, your organization, and your goals.
Engagements vary based on your goals. Some leaders work with Tom intensively for 3–6 months around a specific transition or challenge. Others engage on an ongoing basis as a trusted advisor as their organizations grow. Tom discusses this during the free discovery call — the goal is always to match the engagement length to what you actually need, not to lock you into an arbitrary timeline.
Tom is based in Tampa, FL and works with executive coaching clients across the USA via phone and video. If you're searching for executive coaching near me or leadership coaching services nationally, Tom is fully available for remote engagements. Many of his most effective coaching relationships have been conducted entirely over the phone — the quality of the conversation matters more than the medium.
Thirty minutes. Tom listens to where you are — your role, your team, the challenges you're facing, what you want to change. He doesn't use the call to pitch you. Most leaders leave with a clearer sense of their leadership gap and what would need to change to close it — whether they decide to work with Tom or not. If there's a fit, Tom will explain what an engagement would look like. If there isn't, he'll tell you that honestly too.
Whether you're ready to step into a bigger role, build a stronger team, or just finally get honest about what's holding you back — Tom is ready to start with a free 30-minute call. No pitch. No obligation. Just clarity.
Same-day appointments available · M–F 9 AM–5 PM EST · Tampa, FL · Serving the USA
