12 Jan Hiring Leaders for New Market Entry: Mistakes Companies Keep Repeating
I’ve watched this happen too many times.
A company announces its expansion into a new market. There’s excitement, capital is committed, and the board is confident. Eighteen months later, the whispers start: timelines have slipped, breakeven keeps moving further out, and everyone’s wondering what went wrong.
The usual suspects get blamed—regulation, culture, competition, timing. But here’s what I’ve learned after years of working with companies expanding globally and into India: the problem almost always started with who you hired to lead the entry, not with the market itself.
The Question Nobody Wants to Ask
When was the last time your board spent as much time defining the leadership profile for a new market as they did perfecting the market entry deck?
I’m guessing never. And that’s exactly the problem.
Why This Matters to You
If you’re on a board or in the C-suite preparing for expansion, this isn’t about theory. It’s about avoiding the expensive mistakes that turn growth opportunities into capital drains, the kind that leadership consulting is designed to prevent.
By the end of this piece, you’ll understand:
- Why “local market experience” can actually work against you
- The difference between operators and market architects (and why you keep hiring the wrong one)
- Why your first successful market expansion doesn’t predict your second
- How governance design determines whether even great leaders succeed
- What actually works when hiring for ambiguity
We're Solving the Wrong Problem
Here’s how most expansion plans get structured:
- Set up the legal entity. Check.
- Hire a country head. Check.
- Replicate the business model. Check.
- Build the team. Check.
- Looks logical on paper. Fails repeatedly in practice.
Why? Because market entry isn’t an operations problem—it’s a leadership problem disguised as one.
Operating in a mature market means executing within established patterns. Entering a new market means making judgment calls without playbooks, building credibility before you have results to show, and navigating stakeholder ecosystems you don’t fully understand yet.
Most companies hire leaders who are brilliant operators. Then wonder why they struggle when there’s nothing yet to operate.
Mistake #1: The "Local Expert" Trap
Let’s find someone who really knows this market.
Sounds reasonable, right? It’s not.
Don’t get me wrong—local knowledge helps. But when it becomes your primary hiring criterion, you end up with leaders who:
- Default to “how things are done here” instead of questioning whether they should be
- Resist experimentation because they’ve seen too many failures
- Overestimate how relevant their past wins really are in this new context
- Struggle when the playbook doesn’t apply
I’ve seen companies hire the most experienced local executive available, only to watch them optimize for yesterday’s market while competitors figure out tomorrow’s.
New markets don’t reward people who know all the answers. They reward people who ask better questions.
Mistake #2: The First-Market Fantasy
Your head of APAC crushed it in Singapore. Naturally, you want them to open the next three markets.
Here’s what you might not realize: the skills that made them successful in market one can become obstacles in market two.
Opening your first new market requires entrepreneurial hustle. You’re figuring things out, moving fast, building as you go. It’s about improvisation and grit.
The second market? That’s when you need to start thinking institutionally. You can’t just wing it anymore. You need governance, process, scalability.
By the third or fourth market, you’re managing a portfolio. The job has completely changed.
The leader who opened Singapore brilliantly might be the wrong choice for Indonesia—not because they’re less capable, but because the challenge is fundamentally different.
Mistake #3: Hiring Someone to Run What Doesn't Exist Yet
This one’s painful because it happens so often.
Boards hire leaders with impressive track records—usually running large, mature operations. Big P&Ls. Established teams. Proven processes.
Then they drop them into a market where:
- There is no team yet
- There are no processes
- Everything must be designed from scratch
- Credibility must be built before it can be leveraged
What worked when managing 500 people doesn’t work when you’re the only person in the country convincing the first hire to join you.
I’ve watched this play out identically across industries. Six months in, the board starts noticing the discomfort. Twelve months in, they’re discussing “cultural fit issues.” Eighteen months in, they’re searching again.
You hired a brilliant operator. What you needed was a market architect.
Mistake #4: When Experience Becomes Dead Weight
Industry expertise seems non-negotiable when hiring for expansion.
We need someone who’s spent twenty years in pharma” or “They must have fintech background.
But in unfamiliar markets, deep industry experience can actually slow you down. Here’s how:
- You assume what worked elsewhere must work here (it doesn’t)
- You miss opportunities because they don’t fit your mental model
- You’re slower to adapt because you’re unlearning while learning
- You optimize for certainty in an environment defined by uncertainty
Sometimes the leader who’s done this exact job in three other countries is less effective than the one who’s proven they can figure anything out in any context.
Mistake #5: Believing Your Brand Will Do the Heavy Lifting
Global companies entering India think their brand recognition will smooth the path. Indian companies going global think international clients will line up because of their track record back home. Both are usually wrong.
Because here’s the reality:
- Regulators don’t care about your logo—they care about the person sitting across from them
- Partners don’t trust your brand deck—they trust whether you understand their context
- Teams don’t follow brand promises—they follow leadership behaviour
Your brand might get you the first meeting. Your leader determines whether there’s a second one.
The India Factor: Why One Playbook Doesn't Work Both Ways
Coming into India:
You need leaders who can navigate regulatory complexity that doesn’t always follow written rules, build relationships in ecosystems where informal networks matter more than org charts, and operate effectively before formal structures are fully in place.
Expanding from India:
You need leaders who can demonstrate governance maturity that global partners expect, build process credibility immediately (not eventually), and adapt culturally without losing authenticity.
Using the same evaluation criteria in both directions? That’s a mistake I see repeatedly.
A Story You've Probably Lived
A global consumer brand entered India a few years ago. They hired a strong commercial leader—someone brilliant at sales execution and scaling operations.
What they didn’t assess: comfort with regulatory ambiguity, ability to navigate stakeholder relationships beyond commercial metrics, or fluency in India’s informal business ecosystems.
Growth stalled. Not because the product was wrong or pricing was off. Because relationships weren’t built properly and regulatory approvals kept getting delayed.
By the time they made a leadership change, they’d lost a year of momentum and millions in invested capital.
The strategy was fine. The leadership wasn’t designed for the actual challenge.
When Boards Make It Harder (Without Meaning To)
Sometimes leadership fails not because you hired the wrong person, but because you set them up in a system designed for failure. In many organizations, this tension plays out inside the senior leadership team itself — where unclear authority, overlapping roles, and misaligned expectations turn the C-suite into a battleground rather than a decision-making powerhouse.
I see boards unintentionally increase risk by:
- Giving vague mandates (“grow revenue” without clarity on how or by when)
- Creating unclear success metrics (is it market share or profitability first?)
- Taking too long to clarify decision rights (who approves what?)
- Limiting board access during the critical early phase
Even exceptional leaders struggle inside weak governance structures.
What Actually Works
After working on dozens of market-entry leadership searches, here’s what I’ve learned:
The most successful expansions happen when companies:
- Design the role around what must be built, not just managed. What needs to be created from nothing? That’s your job description.
- Align early and deeply between board, CEO, and CHRO. This can’t be delegated to HR alone.
- Challenge the “safe” profile. The candidate who looks perfect on paper often isn’t.
- Assess for adaptability over familiarity. How have they handled ambiguity before? That matters more than whether they know your sector.
Success isn’t accidental. It’s architected.
Three Questions Before Your Next Market Entry Hire
Before you approve that country head hire, pause and ask:
Are we hiring for familiarity or adaptability? Be honest. Are you choosing this person because they feel safe, or because they’re actually the right fit for the challenge?
Have we designed this role or just filled it? Did you define what this leader must build, or did you just copy-paste from the last market?
Are we giving them the governance structure they need to succeed? Clear mandate? Defined metrics? Board access? Decision rights?
The Uncomfortable Truth
Markets don’t reject strategies. They expose leadership assumptions that should have been challenged months earlier.
Getting the leadership hire right at entry is one of the most powerful decisions a board can make. Getting it wrong is one of the most expensive.
If you’re preparing for market expansion and want to think through the leadership architecture before you’re nine months in, wondering why timelines have slipped, let’s talk.
