10 Unexpected Challenges Every Leader Should Expect


Feeling overwhelmed by the unforeseen hurdles of leadership? Explore how expecting the unexpected can transform your approach to leadership. Why wait to be caught off-guard?

Challenges Are, Well… Challenging

As leaders, we know many aspects of our role will be challenging. For example, we look ahead at our weekly meeting schedule and mostly know in advance where challenges may exist. We know that our role requires making decisions which can be challenging. We know pending projects may present a challenge.

Expected challenges are challenging.

Unexpected challenges can derail or even destroy us, though. 

When we anticipate a challenge, we can somewhat prepare to face it well. When a challenge appears rather unexpectedly, we are caught off-guard. It’s these types of challenges that do the most damage.

Preparing for the Unexpected

This is one of the core reasons I wrote Big Shoes To Fill.

Helping the unexpected become expected better prepares leaders for success.

What are some unexpected things we can and should expect? Here are 10 I consistently see:

1. Staff Changes

Staff stability is a myth. I remember when I felt I finally had the perfect team constructed. It lasted a month before one team member accepted a great opportunity in another organization.

His decision to leave bothered me. I didn’t take it personally, as this opportunity was an excellent fit for him, but I hated the thought of our “perfect” team becoming less than perfect. I was caught off guard.

We cannot expect staff stability. There’s no such thing. It’s a myth. We should always work to develop leaders and remain prepared to launch leaders. It’s part of the job.

Additional Reading: 

Every Three Years: The Impact of Millennial Job Hopping on Workplace Culture 

2. Frustrated People

If you’re a leader, you have, by definition, followers. If you have followers, you’ll inevitably make people frustrated.

Leadership requires too many decisions for everyone always to agree. 

When we expect everyone to be happy followers, we set ourselves up for even more frustration. Rather than be caught off guard, we should expect people to be unhappy from time to time. These moments can be excellent learning experiences for us and those around us. When we expect it, we’re better prepared to learn from it.

3. Resistance to Change

I have an entire section of Big Shoes To Fill dedicated to this fallacy. People don’t resist change, but they do resist loss and uncertainty. When you attempt to lead a change of any kind, expect some pain.

Leaders caught off guard by the frustrations of change tend to blame the frustrated people. When we expect challenges, we’re better prepared to process frustrations with them.

Big Shoes To Fill can help you become an expert in leadership changes. 

4. Non-Work Challenges

This will shock nobody: The areas of our life don’t remain in nice, tidy compartments. When one area of our life is a mess, our entire life suffers.

If you lead a team, individuals will face non-work challenges that will directly affect their work life. It’s unfair to assume this won’t happen. We should expect it, offer support, and create a tenable expectation during these hardships.

5. Evolving Customer or Culture Preferences 

No product, service, or approach lasts forever. The only constant in life is change. We must evolve our businesses as customer, culture, or congregational preferences evolve.

We find ourselves caught off guard when we don’t expect these changes.

When I interviewed Frank Blake, the former CEO of Home Depot, he noted that “People around you who believe they understand the business might only understand the business from 20 years ago.” This is the reality of product and service preferences. It’s, therefore, critical to keep your pulse on what the customer wants. Expect things to evolve.

6. Leaking Vision

I first heard the term “vision leaks” from my former boss, Andy Stanley. He most likely heard it from someone else.

It’s true. While you may own and ooze the vision, most people around you are less invested than you. You’re the leader, after all.

We should expect people to lose sight of the why behind our what occasionally. We can keep the vision out front by repeating it over and over and over again. But this won’t keep it from leaking every so often. When we expect our vision to leak, we’re better prepared to diagnose vision-related issues and reinforce our why.

7. Operational and Strategic Certainty 

While we should always have mission and vision clarity, it’s impossible to expect strategy or model certainty. In a changing landscape, how we accomplish what we’re called to do must change.

Leaders who expect their strategy to remain constant get left behind. This is true in every organization but is especially noteworthy in a local church. You see it everywhere. If a church operates today the same way it did decades ago, it cannot remain connected to culture and the evolving needs of its community.

Additional Reading: 

How to Make Great Decisions Without Any Clarity 

Certainty vs. Clarity: How Effective Leaders Navigate the Difference 

8. Busy Seasons

We should rarely find ourselves caught off guard by a busy season. We usually know when these seasons are, allowing us to plan accordingly.

For instance, I led a church for over 13 years. I knew summer would be more relaxed than Easter or Christmas. I knew that preaching weeks were more hectic than non-preaching weeks.

When I paid attention to these pending busy seasons, I could prepare in advance by creating the necessary margin in my work life. But when a busy season caught me by surprise, it was challenging to catch back up.

It’s impossible to see every busy season in advance, but if you can prepare for those you can identify today, you’ll be prepared when they arrive.

Additional Reading: 

4 Preparation Commitments that Make All the Difference 

6 Steps to Break Free from the Busyness Trap

9. Unsolicited Feedback

Unsolicited feedback can be the worst. Whenever someone says, “Can I share something with you?” we cringe.

Unexpected feedback often hurts. When we’ve worked hard to create a product, offer a sermon, or lead an endeavor, unsolicited feedback feels much heavier than it should. On the other hand, when we begin expecting it, the feedback can help, even if the timing is poor.

I recently preached at a church. I do this often when working with pastors and church teams on ministry strategy and discipleship pathways. After the first service, a staff member said, “Can I give you some feedback?” I immediately responded with a yes, because I know how often this happens in churches! I wasn’t caught off guard, which allowed me to receive his suggestion and slightly adjust for the next service. However, had I been surprised by his request, I may have politely listened while internally discounting.

10. You’re Own Discontentment

Finally, no matter how much you love your job, team, customers, etc., you’ll sometimes find yourself disappointed. It’s human nature.

When discontentment hits the unprepared, it feels heavier and change feels more necessary to resolve the tension. On the other hand, when we expect some moments of discontentment along the way, when it arrives, we’re better prepared to weather the internal irritations and pinpoint the actual realities of our frustration.

Learning to Expect the Unexpected

In navigating the complex journey of leadership, the paradox of expecting the unexpected becomes our true strength. These ten challenges, while unforeseen, mustn’t be a surprise. Ultimately, leadership is less about the avoidance of difficulty and more about the readiness and resilience we cultivate in response. After all, if leadership were easy, everyone would do it.