Most leaders walk into a broken organization and immediately start fixing things. New processes. New hires. New strategy. Six months later, the same problems come back. The issue is not effort. The issue is that they never understood their leadership legacy before trying to change it. And that blind spot costs organizations more time, money, and talent than almost any other leadership mistake a leader can make. Erik Akesson has spent over 25 years walking into stuck situations across banking, fintech, consulting, and venture capital and making them move.
He joined the Leadership Spotlight podcast, powered by OneStream Live, to share what he has learned about why smart leaders keep hitting the same walls.
In this blog you will find out what leadership legacy really means, why it starts earlier than most leaders expect, how to pace change without burning your team out, and what the military does differently that most corporations completely miss. If you lead a team, run a company, or are building something from scratch, this is worth reading carefully.
What Leadership Legacy Actually Means in Business
Most people think of legacy as something a leader leaves behind after a long career. Erik reframes it completely.
“Legacy is the situation you are in because of the history you have.”
Your leadership legacy is not in the future. It is operating right now. The technology your company runs on, the culture in your office, the way your team makes decisions, all of it is the accumulated output of choices made before today. Many of them made before you arrived.
“Legacy is an omnipresent situation that everybody is facing whether they are aware or not.”
Erik co-authored a white paper on this at BearingPoint alongside the former CEO of one of Finland’s largest banks, the ex-CFO of national airline Finnair, a psychotherapist specializing in inherited trauma, and a Finnish military general. That group was deliberate. Because leadership legacy shows up in every industry, not just banking or tech.
Think of it like therapy. A therapist does not start by asking what you want to change. They start by asking what shaped you. Organizations need that same honest reckoning before launching any change program. The leaders who do this work stop fighting symptoms and start fixing root causes. That is the real benefit.
Why Startups Have a Legacy Problem From Day One
Most founders assume legacy is a problem for old companies. Erik learned otherwise from building his own startup.
When he co-founded Plug Software across three garages in Stockholm, Helsinki, and Gothenburg, the company was brand new. Then their CTO asked one question: Azure or Amazon Web Services?
“I realized later that was a big legacy moment for us. The moment we decided, we locked ourselves into building on that environment and could not easily move from there.”
That one conversation shaped everything. Cost structure. Scalability. Integration options. What felt like a routine technical choice became a path-dependent decision that closed off future options.
“Once you steer down a path, you knock yourself out of others.”
Finnish military general Yuri Ritaala, who contributed to the white paper, made the same point about Finland’s decision to buy the F-35 fighter jet. They did not just buy a plane. They locked in a 40-year ecosystem of compatible missiles, communication systems, and surveillance tools.
“Once you lock yourself into a 40-year decision like F-35, you exclude yourself from other systems maybe 20 years from now, even if better options exist, because they are not compatible with what you have.”
The practical takeaway for founders: build flexibly. Every early decision is a legacy decision. The longer you wait to recognize a lock-in, the more expensive it becomes to fix.
The Optimal Rate of Change: How Fast Is Too Fast?
The BearingPoint white paper introduces what Erik calls the ORC: the optimal rate of change. It is one of the most useful frameworks for any leader facing transformation.
“If you want an omelette, you have to break eggs. If you say you cannot have any damage at all, there will be no omelette. That is not a risk-free outcome. That is just a different kind of failure.”
When Erik looks at teams going through change, he sees the same pattern every time. Around 10 to 20% are forward-leaning and already want change. The large middle group sits on the fence. And another 10 to 20% actively resist.
Most leaders assume the middle follows them. Erik disagrees.
“As a leader, you believe that they will follow you. I don’t think they do. I think they follow that forward-leaning top percent of the team.”
The most effective leadership move during change is not broadcasting vision from the top. It is empowering the forward-leaning minority to bring the middle with them. That is where change actually spreads.
As for the resistant tail:
“The minimum damage you have to accept is usually that you have to remove some of these people. That is the eggs you have to break.”
Too little change builds change debt that eventually forces a harder correction. Too much change too fast burns out your best people. Finding the right pace is the real work of leadership growth.
“People vaguely want change but they don’t want to talk about the side effects. That is one of the key messages to anyone in a C-suite position.”
What the Military Gets Right
In most big corporations, strategy teams are filled with former consultants who never worked in the industry they are now advising. Erik experienced this firsthand.
“When I was head of strategy for part of a bank, I was surrounded by strategy people that had never been in banking. To me that was quite shocking.”
The military does it differently. Every general started as a foot soldier. Promising thinkers are moved to headquarters for strategic planning, then back to field command, then headquarters again. That rotation continues throughout a career.
“If you look at the LinkedIn profiles of top military brass, you will find this pattern repeated: headquarters, field role, headquarters, field role. They keep building both strategic and operational depth.”
The result is a strategy function grounded in recent, real operational experience. Long-term decisions are made by people who know what the ground level feels like right now, not 20 years ago.
“I wish that big banks had the same strategy departments as military headquarters do.”
The lesson applies everywhere. The people making your long-term decisions need recent experience living inside your present reality. Strategy divorced from operations is a leadership legacy problem waiting to happen.
Kalista's Paradox: The Book That Makes Legacy Accessible
After 100 CEO conversations across the Nordics, the feedback on the BearingPoint white paper was consistent: this should be a book.
Through LinkedIn, Erik connected with Elaine Sterling, a Canadian author with Finnish roots who had spent 18 years teaching corporate communications at the University of Toronto and had already written 12 books. Her verdict on the white paper was direct.
“She said it was too academic. It would only appeal to guys like me that fly around airports and buy management books. We needed to write it as a novella so it could reach a broader audience.”
Kalista’s Paradox is the result. It combines a fictional story about a 26-year-old who unexpectedly becomes CEO of a family business, a practical framework explaining how legacy works across banking, military, aviation, and healthcare, and personal legacy stories from 14 co-authors across eight countries.
“What we hope is that Kalista’s Paradox becomes for legacy what Sophie’s World was for philosophy. Opening up access to a world that we believe is seriously underutilized.”
Final Thoughts
The thread running through everything Erik shared is simple: before you decide where to go, understand where you are and how you got there.
“Don’t just set out on a random change journey from where you think you are. Invest time in understanding where you are and why. Then you will choose the right path forward.”
The leaders who understand their leadership legacy make better decisions, build stronger teams, and create organizations that are ready for what comes next. Those who skip that step keep fixing the same problems over and over, just with different labels on them.
Whether you are a startup founder choosing your first cloud platform or a C-suite executive planning a major transformation, the question Erik keeps returning to is the right one.
What led me here and why?
Answer that honestly and your leadership legacy stops being something that happens to you and starts being something you shape on purpose.
Frequently Asked Questions
The legacy trap in leadership occurs when leaders focus more on preserving past success than on adapting to future needs. Instead of asking what is working now, they defend what worked before. This is one of the most common leadership blind spots and one of the hardest to recognize because past success makes the trap feel like good judgment rather than a warning sign.
Leaders fall into the legacy trap when ego, comfort, or fear of change keeps them tied to old ways of thinking. The same habits and decisions that drove early success can quietly become the biggest barrier to leadership growth. Without honest self-reflection and regular feedback, most leaders do not realize they are in the trap until the damage is already visible in their team.
The legacy trap can slow innovation, erode trust, and leave teams feeling stuck under outdated leadership mindset and direction. When leaders stop adapting, teams stop bringing new ideas because nothing changes anyway. Over time the most capable people leave first, and what remains is a culture built around protecting the status quo rather than building toward what comes next.
Leaders can avoid the legacy trap by staying open to feedback, encouraging new ideas, and focusing on impact instead of image. The most important habit is regularly asking what is no longer working, not just what is going well. Building a culture where honest challenge is welcomed rather than punished is the most reliable way to catch leadership blind spots before they become organizational problems.
The biggest mistake is clinging to outdated, control-based habits rather than evolving into a coach-like mindset that fosters autonomy and accountability.
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