What I’ve Learned About Leadership Through Difficult Transitions
By Dr. Brian D. Wickstrom
Transitions are one of the great constants in leadership.
Some are exciting — stepping into a new role, launching a new initiative, building a new team. Others are more difficult — restructuring, leadership changes, unexpected organizational challenges, or personal seasons of uncertainty.
Throughout my career across higher education, athletics, nonprofit leadership, and corporate strategy, I’ve experienced both ends of the spectrum. And while every transition is different, each one has taught me something important.
Difficult transitions don’t break leaders — they reveal them.
Lesson 1: Growth Rarely Happens in Comfort
If I look back at the moments where I grew the most as a leader, they weren’t the seasons where everything was stable and predictable.
They were the seasons when:
Expectations shifted overnight
Organizations changed direction
Challenges became public
Communication became critical
Difficult decisions had to be made quickly
Emotions ran high across teams
Transitions force you to evaluate what you truly believe and what you’re willing to stand for.
You learn:
What your values are
What your priorities are
What kind of leader you want to be
And sometimes, the toughest moments bring out your strongest leadership.
Lesson 2: Transparency Reduces Fear
When organizations face change, uncertainty becomes the enemy. Silence creates assumptions. Assumptions create anxiety.
During transitions — especially difficult ones — your team watches everything closely. They want to know:
Are we safe?
What happens next?
Are we being told the truth?
Who is making decisions and why?
One of the best things a leader can offer in these moments is clarity, even if the clarity is simply:
“Here’s what we know today, here’s what we don’t know yet, and here’s how we’re moving forward.”
People can handle hard news.
What they can’t handle is being left in the dark.
Transparency builds trust. Trust builds stability. Stability builds momentum.
Lesson 3: Grace Under Pressure Matters More Than Perfect Outcomes
Leadership transitions are rarely clean. Emotions, opinions, expectations, and narratives swirl around the process — especially in public-facing institutions like athletics and education.
I’ve learned that the most important question during turbulent periods is not:
“How do I win this moment?”
It’s:
“How do I carry myself through this moment?”
Because:
People remember tone
People remember fairness
People remember humility
People remember how you treated them
People remember whether you stayed centered
Being steady, respectful, and committed to values creates a long-term positive impact that outlasts any single decision.
Lesson 4: Transitions Reveal Who You Are — and Who You Have Around You
When things are smooth, everyone appears aligned.
When things are turbulent, the true character of an organization — and its people — becomes visible.
Difficult transitions reveal:
Who communicates honestly
Who steps forward to help
Who chooses what’s best for the team
Who acts with integrity
Who values relationships over politics
Those observations become invaluable in shaping future teams, partnerships, and leadership decisions.
Lesson 5: Every Transition Creates a Chance to Rebuild — Even Better
Some transitions end well. Others end painfully.
But every transition opens a door.
Over time, I’ve realized that difficult transitions often:
Push you toward the next chapter you didn’t know you needed
Open opportunities you weren’t expecting
Allow you to rediscover your strengths
Refocus you on what matters most
Make you more resilient
Expand your capacity to lead others through difficulty
When one chapter ends, another begins — often with greater clarity, deeper purpose, and renewed energy.
Lesson 6: Your Response Becomes Your Reputation
Titles change. Seasons change. Organizations change.
But:
The way you treat people during transitions defines you far more than the transition itself.
I’ve always tried to:
Communicate openly
Stay grounded in values
Show respect even in disagreement
Keep teams focused on mission and purpose
Maintain dignity regardless of circumstances
Leadership is not about being perfect — it’s about being principled.
And transitions give you the chance to demonstrate those principles when they matter most.
Moving Forward With Purpose
Through every professional transition — from athletics to education to the private sector — I’ve tried to carry forward the same philosophy:
Grow through the experience.
Serve the people around you.
Stay grounded in your values.
And keep your focus on the next chapter.
Difficult transitions don’t define you — but the way you navigate them absolutely can strengthen you.
And often, the leaders shaped in seasons of uncertainty become the same leaders who inspire confidence, stability, and hope in others.
