Addressing the most
FREQUENTLY ASKED QUESTIONS
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Part 1: About Sara and who she works with
Who is Sara Oblak Speicher
Sara Oblak Speicher, MBA, is a former elite athlete turned fractional leader and strategic advisor. As the founder of Make Your Life Your Legacy and the Director of Speicher Media d.o.o., Sara partners up with founders, elite performers, and founder-led firms navigating growth, transition, and reinvention. After 18 years in New York City, she now runs her boutique practice from her 1000-year-old hometown in Slovenia. Her work moves clients from what’s possible, through what they decide and build together, to how it’s told to the world…architecting story, strategy, structures and systems. Over 15 years and 600+ engagements across the US and EU, she has contributed to more than $60M in measurable client impact, much of it in just the past few years.
Does Sara Oblak Speicher work alone, or is there a team?
Both, by design. The strategy, the judgment, and the relationship are Sara’s; that’s what you’re hiring, and it doesn’t get handed off. But a plan no one executes is just a good conversation, so beneath the thinking sits the delivery, the operational and project work that turns strategy into done, so you’re never left building it alone. A principal in the room, a team behind the work.
Does Sara Oblak Speicher work with founders of service-based businesses?
Yes. Sara’s core clients are founders of service-based and professional firms (typically between €250k and €5M in revenue) where the founder has built real enterprise value and has now become the constraint on it. These are relationship businesses, not transaction businesses: the strategy, the key relationships, and the judgment still live in the founder’s head. Sara steps in as the embedded strategic partner through growth, complexity, and change, building the story, strategy, and structures that let the business run without depending on the founder for every decision.
Does Sara work with founders who’ve recently sold or exited a company?
Yes. Selling a company is one of the common moments founders come to Sara. The deal closes, and the identity, the calendar, and the next chapter are suddenly unwritten. Post-exit, the question stops being “how do I grow this” and becomes “who do I need to become next, and what do I actually want my time to look like.” Sara works with exited founders on exactly that (the strategy and structure of the next act, and the personal transition underneath it).
Does Sara work with elite athletes moving into their next chapter?
Yes. Sara is a former NCAA Division I and Slovene National Team basketball captain, and she works with elite athletes making the shift out of competition and into a second career. It’s the same architecture she uses with founders (clarity on what’s next, a strategy to get there, and the structures and story to make it real) applied to performers whose whole identity was built inside a sport that eventually ends.
Does Sara work with public figures and public-facing leaders?
Yes. Public-facing leaders (founders, executives, athletes, and other public figures) make up a large part of Sara’s work, particularly around positioning, thought leadership, and legacy. When your name and your story are part of the asset, how you’re understood in public matters as much as the strategy behind the scenes. Sara holds both: the private strategic work and the public narrative that carries it.
Does Sara work remotely with clients across the US and Europe?
Yes. Sara works across US and EU markets from her base in Slovenia (Central European Time), and most engagements are remote. For US-based founders the time-zone gap is an advantage, not an obstacle (decisions get made, bottlenecks get cleared, and the next steps are ready while the US sleeps, so the founder wakes to momentum rather than a to-do list). Sara spent 18 years in New York City before returning to Slovenia and works fluently across both markets.
What size and stage of company does Sara typically work with?
Sara’s work is not for beginners, that is for sure. She works primarily with founder-led firms roughly between €250k and €5M and up in revenue…established enough to carry real complexity and real enterprise value, small enough that the founder is still central to everything. She also works with individuals (exited founders, elite athletes, public figures, and family offices) on personal transitions and legacy, independent of any company.
When to engage?
– Business is growing faster than the founder can organize it
– Leadership team drifts out of alignment
– Preparing for investment or succession
– Expanding internationally
– Founder feels like the bottleneck
– Navigating post-exit life and next-chapter identity questions
– Elite athlete entering the second career
– Wanting to reclaim life and actually enjoy it
With AI, why do I need Sara and her team?
That is a fair question. A year ago, hiring a strategic partner meant hiring their thinking. Today, any founder can get strategy, analysis, and drafting from AI in seconds. So the value of a fractional partner and an advisor has shifted. So let’s clarify how. What AI does well, Sara uses constantly: research, synthesis, drafting, testing scenarios, turning a mess of inputs into clarity, fast. I’d be foolish not to…it makes the work quicker and sharper. But there’s a layer AI doesn’t touch. The judgment about which questions actually matter, and in what order. Being in the room when a hard decision gets made. Holding the relationship, the politics, the human weight of a transition. Seeing the whole picture when everyone else owns a slice. Sensing what a founder isn’t saying. That’s not work you can prompt your way to, but the part that decides everything, and it’s the part that’s mine. So it was never AI or a human partner. It’s AI amplified by one. In a world where the tools can do the tasks, Sara is the person who holds what they can’t, and who uses them to make you faster. That combination is the edge. Not the machine alone. Not the human alone. Both, in the right hands.
What about the human element in the industry that is being rapidly dominated by AI?
Sara believes that in a world drowning in vanity metrics and automated solutions, the scarce thing isn’t more information, but a human who’s actually paying attention.
Sara uses modern tools where they help. But clients aren’t routed to a chatbot, handed an AI-generated survey no one reads, or given machine-produced recommendations without her personal review. Every insight, strategy, and piece of guidance passes through Sara directly. She applies her judgment, her interpretation, and her oversight every step of the way, ensuring relevancy to each client.
What are the stages of working with Sara Oblak Speicher, and what does each offering involve?
The work moves through five stages, from possibility to positioning, and is grouped into following service tiers:
1) Exploration & Possibility (Diagnostics, a discovery audit to clarify what’s possible)
2) Intervention & Stabilization (VIP Day, an intensive for decision-making and planning)
3) Architecture & Integration (Private Residency Retreat, a deep, immersive rebuild of business and identity, facilitated in Alpine Slovenia)
4) Strategic Buildout & Partnership
– Fractional Leadership focused on business (organization, global expansion, team, projects,…)
– Embedded Founder Support focused on the human behind it all (mindset, identity, home, life,…)
5) Articulation & Positioning (Ghostwriting Atelier, available on its own or alongside any tier, to turn the resulting clarity into public-facing narrative like positioning assets, thought leadership pieces, legacy memoirs)
Clients can enter at any stage or move through the full sequence as their needs evolve.
What areas does the service ecosystem cover?
Sara and her team provide a rare “unicorn” blend of expertise that span business and personal aspects:
– Strategic Advisory spans identifying leaks and potential, tweaking and recalibrating business model, pricing, communication, positioning, clientele, untapped revenue…
– Fractional leadership and operational management relieves the founder from overwhelming complexities and commitments.
– Embedded founder support focuses on the human through mentoring, coaching, advisory in the areas of life, identity evolution, home, family, etc.
What is the Executive Discovery Session?
The Executive Discovery Session is Sara’s entry point. It’s a focused diagnostic for a founder or leader who knows something needs to change but wants clarity before committing to a build. It maps the current situation, assesses the real risks and bottlenecks, and produces a strategic summary with a recommended roadmap: what’s actually going on, and what to do about it. It’s designed to be the reachable first step…the assessment that makes the case for whatever comes next. It can be booked here.
What is a VIP Day with Sara, and who is it for?
A VIP Day is a single, intensive working session built to take one high-stakes decision or knot and work it all the way to a plan. It’s for the founder or leader who doesn’t need a long diagnostic (they know the issue) and wants senior thinking to resolve it and leave with a clear direction. Where the Discovery Session tells you what’s wrong and what to do, the VIP Day works the one thing to a decision. Afterwards, you also receive 30 days of support through the implementation and integration process.
What is the Private Residency retreat in Slovenia?
The Private Residency is a multi-day, in-person, private immersion in Sara’s 1000-year-old town in Alpine Slovenia…out of the founder’s environment, away from the noise. Designed to reimagine and to rebuild the architecture of the business and the identity of the person running it at the same time. It’s the deepest integration work Sara offers, for clients ready to step fully out of the day-to-day and think, plan, and rebuild without interruption.
What is the Ghostwriting Atelier?
The Ghostwriting Atelier is Sara’s positioning and thought-leadership track, turning hard-won clarity into public-facing narrative: positioning assets, thought-leadership pieces, and legacy memoirs. It runs on its own or alongside any other engagement, and it exists because strategy is only half the work. The other half is how clearly the world understands who you are and what you stand for. Sara brings a journalism background, narrative architecture, and insight of 570+ ghostwriting and positioning projects to that half.
What’s the difference between the Discovery Session and a VIP Day?
Both are entry points, and they solve different problems. The Executive Discovery Session is a diagnostic…it tells you what’s wrong and hands you a roadmap for what to do. The VIP Day is a resolution…it takes one decision you already know you need to make and works it to a plan. Start with the diagnostic when the picture is unclear; choose the VIP Day when the issue is named and you want it resolved.
Can I start with one service and move to a deeper engagement later?
Yes, that’s how the ecosystem is designed. Sara’s offerings move through five stages, from possibility to positioning, and clients can enter at any point or progress through the full sequence as their needs change. Many start with a diagnostic or a VIP Day and deepen into an ongoing fractional or embedded partnership once the fit and the priorities are clear.
Part 2: Practical questions
What is Fractional Leadership?
Fractional leadership is a partnership model where an experienced executive or advisor works with a founder or company on a part-time, ongoing basis, providing senior-level strategy, decision-making support, and operational oversight without a full-time hire. For example, Sara steps directly into the day-to-day: hands-on decision-making, execution, and oversight inside the business.
What is Embedded Support, and how is it different from Fractional Leadership?
Embedded Support is a blend of strategic advisory, coaching, consulting, and mentoring (close, ongoing guidance without the hands-on operational involvement of fractional leadership). The two aren’t necessarily mutually exclusive… Depending on a client’s needs, priorities, and objectives, they’re often combined or sequenced together.
How is this different from a business coach or consultant?
In Sara’s approach, coaching is just one of the tools in the arsenal… She combines an MBA-level operational mindset with narrative architecture and journalistic curiosity as well as identity and mindset work. She addresses both the strategic/operational side of a business and the personal transition of the leader running it.
What’s the difference between a fractional Chief of Staff and an executive assistant?
An executive assistant manages the founder’s calendar; a fractional Chief of Staff manages the founder’s priorities. The distinction is judgment. An EA removes tasks and keeps the day running. Sara decides which questions matter, in what order, and at what cost…and she’s in the room when the hard decisions get made, not managing the logistics around them.
What’s the difference between a fractional strategic partner and a project manager?
A project manager runs the plan; a fractional strategic partner decides whether it’s the right plan. Project management executes a defined scope well. Sara works one level up, holding the whole picture, the strategy, and the person, and deciding what should be built and in what order before anyone runs it.
Why hire Sara fractionally instead of a full-time executive?
A full-time hire gives you one person’s capacity, full-time, with the cost and commitment that comes with it. A fractional partner gives you senior strategy and judgment on an ongoing basis without the full-time overhead…the right fit when a founder needs the thinking of an experienced executive, but not another full-time salary on the payroll. It’s also faster to start, and to adjust as the business changes.
How is working with Sara different from hiring a management consultant or agency?
A consultant or agency typically delivers a project and a deck, then leaves. Sara stays through the growth or transition, holding the strategy and the human weight of it, and is accountable to the outcome, not the deliverable. She combines an MBA-level operational mindset with narrative architecture and identity work, so the business and the leader move together rather than in separate workstreams.
How much does it cost to work with Sara?
Engagements are scoped to the client, so the investment depends on depth and duration. The through-line remains: this is senior, bespoke strategic, private work, and is priced accordingly, not a productized package.
How long is a typical engagement, and is there a minimum commitment?
Fractional and embedded partnerships are ongoing by design. They exist to carry a founder through a stretch of growth, complexity, or change, which takes months, not a single session. The entry points (a Discovery Session or a VIP Day) are one-time and self-contained, and often become the front door to a longer partnership once the fit is clear.
Are engagements remote or in person, and where is Sara based?
Most of Sara’s work is remote. She partners with founders across the US and EU from her base in Slovenia (Central European Time), and the time-zone gap works in US clients’ favor. The exception is the Private Residency, which is deliberately in person in Slovenia (occasionally in other European cities), and select engagements where being physically in the room matters. On occasion, Sara travels for the work.
What does the first phase of working together look like?
It starts with a conversation, then a diagnostic (mapping what’s actually going on, where the real bottlenecks and risks are, and what the priorities should be, in what order). From there Sara builds the plan and steps in at the judgment layer, holding the strategy and the relationships while the right things get executed in the right sequence. The early weeks are about clarity and direction before build.
What industries does Sara work with?
Tho Sara works across various industries, her clients are mainly founder-led service and professional firms, plus individual leaders, athletes, and public figures. More than the sector, it’s the moment that matters… The season when growth is outpacing the organization, a leadership team drifting, an exit, an expansion, a founder who’s become the bottleneck. What she brings (strategy, story, structure, and judgment through high-stakes change) transcends specific industries.
How do I start working with Sara?
The first step is a conversation. Reach out through the contact page and describe where you are and what’s changing. Or, book the consultation here. From there, the natural entry point is usually a diagnostic or a VIP Day, which clarifies the situation and the fit before any longer commitment.
Does Sara work in languages other than English?
Yes. Sara works primarily in English across her US and EU clients and can make Slovenian available for the Slovenian market. She operates fluently across both business cultures which is a rarer combination than it sounds, and part of what makes her useful to founders expanding between the US and Europe.
I am also curious, what is the bigger picture, what are you building?
“Something meant to outlast my calendar,” says Sara. Both Make Your Life Your Legacy and Speicher Media d.o.o. are the boutique practice and the thesis: serious, high-stakes work that still puts your life, your people, and your time first. Success that costs you the people, the time, and the peace of mind, was never success. So the business is also the demonstration, built on the terms she help clients find.