Leadership is not just about vision and charisma — it’s about choices. Sometimes brutal ones. The hardest decisions leaders make often come with no easy answer, no perfect outcome, and no clear applause. These are the moments that define you.
Whether you’re leading a startup team, a growing organization, or a movement, the weight of decision-making is real. And it’s often lonely.
This blog explores five of the most difficult decisions leaders face — and how to approach each one with clarity, courage, and strategy.
1. Letting Go of a Team Member (Even a Good One)
Why it’s hard:
People are at the heart of every organization. Firing someone, especially a loyal or well-liked employee, is emotionally tough — but often necessary for the health of the team.
When it comes up:
- Performance issues that coaching hasn’t resolved
- Culture misalignment
- Company restructuring or financial constraints
How to approach it:
- Start with clarity. Be honest about what’s not working — with yourself and with the employee. Avoid vague justifications.
- Document everything. Keep a record of performance conversations to ensure fairness and transparency.
- Act quickly but respectfully. Dragging it out creates anxiety for everyone.
- Support the exit. Offer a recommendation, a transition plan, or even time off for job hunting if possible.
Bottom line: Keeping the wrong person too long is unfair to the rest of the team.
2. Saying No to Growth Opportunities
Why it’s hard:
Leaders are wired to build. Turning down funding, a major partnership, or expansion into a new market feels counterintuitive — and sometimes terrifying.
When it comes up:
- You’re under-resourced or unfocused
- A potential opportunity compromises your values or strategy
- The timing just isn’t right
How to approach it:
- Revisit your core priorities. Does this opportunity align with your goals, values, and capacity?
- Consider the long-term cost. Short-term gains can lead to long-term distraction.
- Get an external perspective. Talk to advisors, board members, or experienced peers before deciding.
Example:
A fintech startup in Nairobi turned down a partnership with a large bank because it would have required giving up customer data — a core value they weren’t willing to compromise.
Bottom line: Growth at the wrong time or price can kill momentum. Be strategic, not reactive.
3. Pivoting the Business
Why it’s hard:
You’ve poured time, money, and identity into a vision. Shifting direction can feel like admitting failure — and risks confusing customers, investors, and team members.
When it comes up:
- Product-market fit is weak
- A new insight or trend changes your industry
- Your current path is burning too much cash with too little return
How to approach it:
- Listen to the data. Track user behavior, sales, churn, and feedback relentlessly.
- Frame it as evolution, not failure. Share the pivot story clearly with your team and stakeholders.
- Move decisively. Waffling between old and new drains morale.
Example:
Many African startups began as SMS platforms and later pivoted into apps or digital service marketplaces based on changing user behavior and tech adoption.
Bottom line: Staying loyal to a flawed model is more dangerous than course-correcting.
4. Making Unpopular Decisions
Why it’s hard:
You want to lead with empathy. You care about your people. But leadership often requires making choices that some team members or customers won’t like.
When it comes up:
- Changing company policy
- Adjusting remote work expectations
- Cutting unprofitable services
- Canceling a popular feature or event
How to approach it:
- Be radically transparent. Share the “why” behind the decision.
- Hold space for feedback. Let people express disagreement without taking it personally.
- Stay consistent. Flip-flopping to appease everyone weakens your authority.
Example:
A startup founder transitioned from unlimited leave to structured PTO after productivity dipped. The team grumbled at first, but the structure eventually improved team balance and fairness.
Bottom line: Don’t confuse likability with leadership. Do what’s right, not what’s easy.
5. Stepping Back or Stepping Aside
Why it’s hard:
It’s your company. Your team. Your baby. Realizing that someone else might be better suited to take it to the next level is painful — and deeply humbling.
When it comes up:
- You’re burned out
- You’ve reached a skills ceiling
- The company’s needs have outgrown your role
How to approach it:
- Detach your ego. Focus on what’s best for the mission, not your personal pride.
- Get feedback from trusted mentors. Don’t make this call in isolation.
- Explore alternatives. Can you shift roles? Become chairman? Bring in a COO or partner?
Example:
Many successful founders in Africa have brought in experienced CEOs to scale operations while they focus on product or long-term vision.
Bottom line: Sometimes the bravest thing you can do as a leader is let go.
Final Word: Leadership Is Choice After Choice
The hardest decisions leaders make don’t have clear answers. But they do have patterns:
- They involve people.
- They force trade-offs.
- They test your integrity, clarity, and conviction.
You can’t avoid tough choices. But you can meet them with principles, data, and courage. And when in doubt, choose what protects the mission — not just your comfort.
