The Human Side of Leadership: Challenges No One Prepares You For

When I finished my keynote and opened the floor for questions, I was honestly surprised by both the number of hands that went up and the depth of the questions people asked.

They weren’t about productivity or KPIs.

They were questions like:

• What do you do when you’re a leader and you screw up? How do you rebuild trust?

• What happens when you’re promoted over someone who has been there longer and there’s resentment?

• What do you do when one person’s negative attitude starts affecting the whole team?

• What about when the leader is the problem — and they don’t realize it?

• What if you tried to be vulnerable with your team and it completely backfired?

None of these are technical leadership problems.

They’re human ones.

And the reality is that most leadership development focuses on strategy, planning, and performance management. But the moments that shape a team most often happen in conversations, reactions, and relationships.

These are the moments that reveal the human side of leadership — the part most leaders are left to figure out on their own.

When workplaces are built on strong relationships, performance usually follows. People trust each other more, communicate more clearly, and are more willing to solve problems together.

Research from Harvard Business School professor Amy Edmondson shows that psychological safety is a key factor in high-performing teams.

Let’s look at a few of these leadership challenges.

When You Mess Up as a Leader

At some point, every leader will make a decision that doesn’t land well.

The instinct in that moment is often to explain, justify, or over-apologize.

A more effective approach is usually much simpler: own it.

You might say something like:

“That didn’t work the way I hoped it would. Let’s take a step back and figure out what we can learn from it.”

From there, get curious.

What didn’t work?
What would the team suggest doing differently?

Inviting input doesn’t weaken leadership — it often strengthens trust, especially when people see their ideas considered.

Repair doesn’t come from having perfect answers. It comes from being accountable and moving forward thoughtfully.

When You're Promoted Over Someone With More Seniority

This situation can be uncomfortable for everyone involved.

If someone applied for the same role and didn’t get it, it’s understandable that there may be disappointment or resentment. The first step is often to check your own reactions.

Are you feeling defensive?
Guilty?
Hoping they’ll immediately approve of you?

Acknowledging the transition can help reset the tone.

You might say something like:

“I know this might not be the easiest transition, especially since you’ve been here longer than I have.”

From there, create space for conversation. Ask what would help the working relationship feel productive going forward.

At the same time, clarity still matters. Setting expectations about how you’ll work together helps move the team forward.

When One Person’s Negativity Starts Affecting Team Culture

This is one of the most common leadership challenges people raise.

Tone spreads quickly in teams. One consistently negative voice can influence how others begin to see the work or the workplace.

One helpful reminder is that culture isn’t written on a poster.

Culture is shaped by what gets reinforced — and also by what gets tolerated.

A useful reflection question for leaders is:

What am I tolerating right now that is shaping the tone of my team?

Often the choice becomes this: a short uncomfortable conversation now, or a much bigger cultural issue later.

When the Leader Is the Problem

Sometimes the person struggling isn’t the team — it’s the leader.

And sometimes that leader genuinely doesn’t realize the impact they’re having.

In those cases, the conversation often has to start with impact.

For some leaders, the human side of leadership doesn’t immediately resonate. But the impact on results often does.

Turnover, burnout, disengagement, and lost productivity all carry real costs.

Helping a leader see that connection can sometimes open the door to a different kind of conversation — one that connects people’s experience at work with the outcomes the organization cares about.

Leadership Is Often Messy

The common thread in all of these questions is this:

Leadership isn’t just about decisions.

It’s about navigating relationships, tension, missteps, and expectations.

Those moments can feel complicated — and sometimes lonely.

They’re also the moments that shape how leadership is experienced inside an organization.

That’s a big part of why I created The Leadership Lab.

It’s a small-cohort leadership development experience designed for leaders who want to think more intentionally about the human side of leadership — alongside others who are navigating similar pressures.

Inside the Lab we explore leadership through three perspectives:

• Leading Self

• Leading Teams

• Leading in the Organization

And we work through the real situations leaders are facing right now — not hypothetical case studies.

The next Leadership Lab cohort starts April, 2026 and includes:

• 15 spots in Thunder Bay

• 8 spots virtually

You can learn more about the Leadership Lab here.

Over the next few weeks, I’ll also be writing more about each of these leadership challenges and sharing practical ways leaders can navigate them.

Because the human side of leadership is the part most people are figuring out as they go.