capacity notice
I work with a maximum of 10 individual leaders at any time to ensure responsive support and the personalized attention effective coaching requires.
capacity notice
I work with a maximum of 10 individual leaders at any time to ensure responsive support and the personalized attention effective coaching requires.
Master conflict resolution, build team alignment, and develop the leadership skills that advance your career—without the trial-and-error that damages relationships and limits your growth.
You were promoted because you're excellent at product work. But product leadership isn't about being the best individual contributor—it's about navigating team conflicts, building stakeholder alignment, and having difficult conversations that actually resolve issues.
Without systematic training in these skills, you're constantly firefighting. Conflicts drag on for weeks. Stakeholder conversations create confusion instead of clarity. You're working longer hours, but the problems persist.

I'm Matthew Stublefield, and I've spent 20+ years leading product and technology teams across diverse industries—technology, healthcare, education, manufacturing, media, and finance.
What sets me apart isn't just the breadth of experience—it's that I bring systematic frameworks rather than just "what worked for me once." I've seen what works across different organizational cultures, team structures, and industry contexts. When you're facing a leadership challenge, I can draw from multiple proven approaches and adapt them to your specific situation.
My Background:
20+ years leading teams from 2 to 400 people across technology, education, healthcare, and manufacturing
10+ years in product management roles, including Director of Product Management at CoinDesk and Senior Product Manager positions
Master of Science in Project Management (MSPM) with emphasis in conflict and dispute resolution
Grief Counselor Professional (GC-P) certification—which means I can support the whole person, not just the professional persona you bring to work
Consistent track record of helping teams achieve 2-3x productivity improvements through systematic leadership development
I've navigated the exact challenges you're facing: building alignment across technical and business stakeholders, resolving team conflicts that threatened project timelines, managing up to difficult bosses, and transitioning from individual contributor to leader of leaders.
The difference is that I've systematically studied what makes leadership work across contexts, combining formal training with hands-on experience across multiple industries. This means I can help you develop skills that work in your specific environment rather than applying rigid methodologies that don't fit your organizational culture.
Most executive coaching happens in monthly or bi-weekly sessions, leaving you stuck when challenges arise between meetings. My approach combines scheduled live sessions with ongoing support, so you get help exactly when you need it.
Live Sessions: We build systematic skills and frameworks for conflict resolution, stakeholder alignment, difficult conversations, and strategic leadership. Sessions are scheduled at your convenience and focus on developing capabilities you can apply immediately.
Asynchronous Support: Between sessions, you have ongoing access to guidance via your preferred platform—Signal, Telegram, Discord, or email. When you face a team conflict on Tuesday or need to prepare for a difficult stakeholder conversation on Thursday, you don't wait for your next scheduled session.
This combination creates faster development and more sustainable results than traditional coaching approaches.

Matthew leads with empathy, kindness, and a calm, consistent presence. He balances high standards with a genuine commitment to work-life balance, and he offered thoughtful guidance not just on my work, but on my career and life more broadly. He is a wealth of technical and organizational knowledge. He also navigates challenges and conflicts with respect and clarity. As a product leader or coach, Matthew is the kind of person who leaves a lasting, positive impact on every team he joins."

What sets Matthew apart is his Mr. Rogers-like demeanor. His ability to foster collaboration and create an atmosphere of trust and respect made even the most difficult tasks manageable and, dare I say, enjoyable.
Matthew is the kind of professional you want on your team when stakes are high and the path forward is uncertain. His technical and strategic excellence is matched only by his character, and I cannot recommend him highly enough.

I met Matthew when I was applying for an Internship in the United States. I just came from the Netherlands and I was desperately searching for an internship in the United States.
He helped me with improving my documents, scheduling, planning but also improving my English and grammar. For him it was probably difficult to work with me as a foreign person with different beliefs and a thick accent, but he stayed calm and we both got the best out of each other.
Matthew sees opportunities and solutions that others may not even have thought about.
Conflict Resolution: Navigate and resolve team conflicts quickly instead of letting them fester and damage productivity. Learn when to intervene, when to coach others through resolution, and how to create environments where conflicts get addressed constructively.
Stakeholder Alignment: Build alignment across engineering, design, product, and business functions—even when stakeholders speak different languages and have competing priorities. Develop frameworks for effective communication that actually creates shared understanding.
Difficult Conversations: Handle challenging discussions with confidence—whether it's addressing performance issues, managing up to difficult bosses, or navigating organizational politics without compromising your integrity.
Strategic Leadership: Move beyond tactical firefighting to strategic thinking. Develop the capabilities that position you for your next promotion while improving your current team's performance.
Personal Growth: Leadership development isn't just about career advancement—it's about becoming the best version of yourself. The skills you develop will improve not just your professional effectiveness but your overall approach to relationships, challenges, and growth.
Coaching packages start at $497/month for three sessions with flexible scheduling and asynchronous support included. We'll discuss which approach fits your situation and budget during our discovery call.
Package Options:
3 Sessions: $1,347 if paid in full (or 3 monthly payments of $497)
6 Sessions: $2,567 if paid in full (or 3 monthly payments of $997)
12 Sessions: $4,769 if paid in full (or 3 monthly payments of $1,897)
All packages include live sessions scheduled at your convenience, plus ongoing asynchronous support through your messaging platform of choice between sessions.
To determine if coaching is the right fit for your situation, I need to understand what you're facing and your timeline for development.
After you submit this form:
I'll review your situation and send you a calendar link within 24 hours to schedule a 15-minute discovery call
During our call, we'll discuss your specific leadership challenges, your timeline, and whether coaching is the right fit for your needs
No pressure follow-up - this is a strategic consultation, not a sales conversation. If coaching isn't right for your situation, I'll tell you that directly
And if your question isn't here, grab my email or Telegram from the footer to contact me.
Send me messages whenever you need guidance—video, audio, text, or screenshares through your preferred platform (Signal, Telegram, Discord, email, etc.). No prep work or formal structure required. Just share what's happening when it occurs, and I'll respond during business hours with personalized guidance.
Think of it like having an experienced product leadership mentor available when challenges arise, without scheduling headaches or calendar coordination. You get expert perspective on your specific situation in real-time—whether you're preparing for a difficult conversation, navigating a team conflict, or working through a stakeholder alignment challenge.
You'll start applying new frameworks and approaches within the first session. Most clients notice improvements in how they handle difficult conversations, make decisions under pressure, and communicate with stakeholders within 1-2 months.
Sustainable behavior change and measurable team performance improvements typically take 3-6 months. You need time to practice new approaches, adjust based on what works in your specific context, and build new patterns with your team and stakeholders.
The timeline depends on your engagement level and the complexity of your current challenges. You'll see consistent progress in your leadership capabilities, with the most significant team and career outcomes building over the full coaching period.
That's exactly why I use flexible delivery. Sessions are scheduled at your convenience around your existing commitments—no rigid meeting schedules to work around.
Between sessions, you send questions when challenges arise and receive guidance within 1-2 business days through your preferred messaging platform. You get help when you need it most, not when the calendar allows.
Most clients find that the frameworks they develop actually reduce firefighting time and make their existing responsibilities more manageable. A few hours of coaching often saves dozens of hours you'd otherwise spend struggling with team conflicts, preparing for difficult conversations, or dealing with misalignment across stakeholders.
In my experience, clients who engage genuinely with the coaching process see meaningful improvement in their leadership effectiveness. However, if progress isn't happening as expected, we'll explore what's occurring together.
Sometimes the approach needs adjustment—perhaps different frameworks, modified communication strategies, or addressing underlying challenges we hadn't initially identified. I'm committed to adapting our methods until we find what works for your specific situation.
We'll assess progress throughout our coaching engagement. If after our initial sessions you're not seeing value, we'll discuss whether to adjust our approach or end the engagement. My goal is your development, not just session completion.
Occasionally, coaching reveals that someone might be better suited for a different type of role or organization. While this isn't the outcome anyone hopes for initially, it's valuable clarity that serves your career well in the long run.
Absolutely. I work with many people in "influence without authority" roles—product managers, principal engineers, UX designers, technical leads, and others who need to lead projects and align teams without formal management authority.
The core leadership challenge is usually the same: getting everyone aligned and moving in the same direction. Whether you have formal authority or not, effective leadership is about influencing people to do their best work and feel good about contributing to shared goals.
I have extensive experience both in these roles myself and coaching others who are navigating the complexities of cross-functional leadership, stakeholder management, and project coordination without direct reporting relationships.
All coaching conversations are completely confidential. What you share with me stays between us and isn't reported to your manager, HR, or anyone else at your company.
This confidentiality creates the safe space you need to discuss genuine challenges—whether that's conflicts with your boss, concerns about team members, doubts about your own capabilities, or sensitive organizational dynamics you're navigating.
The only exception to confidentiality is if you express intent to harm yourself or others, which requires me to seek appropriate help. Beyond that legal and ethical boundary, everything we discuss remains private.
You can speak openly about what's actually happening without worrying about political fallout or career consequences from being honest about your struggles.
Practical leadership insights and frameworks from 20+ years of leading teams. No fluff, just actionable guidance delivered to your inbox.
© 2025 Fieldway - All Rights Reserved
Springfield, Missouri, USA
Springfield, Missouri, USA
© 2025 Fieldway - All Rights Reserved