Your Most Senior Leaders Still Need Support: Experience Doesn’t Replace Context
A vice president recently confided in me that they hired a new leader they were excited about, but several months into the role, key initiatives were moving more slowly than expected.
The leader was struggling to build buy-in with their team and campus partners.
The vice president didn't want to micromanage.
They had experienced that themselves earlier in their career and knew how frustrating it felt to have someone constantly looking over their shoulder.
They did what many leaders do with experienced hires: Give the new leader space.
To build relationships.
To learn.
To figure things out.
Except instead of creating momentum, the leader seemed stalled.
As we talked, I asked the vice president a few questions.
Had they shared which campus relationships to prioritize?
Who influenced decisions behind the scenes?
When consensus is needed—and when it isn't?
What success would look like in the first six months?
The vice president paused.
Not exactly.
Leaders sometimes presume that experienced leaders don’t need support or guidance.
What they often need is a different type of leadership.
Why This Happens
Here are the two leadership patterns I see most often in advancement executives, especially when the pressure is high and everything moves quickly:
Highly directive: The leader gives team members the exact answers or directions to follow. It’s fast in the moment, but over time it creates bottlenecks and burnout.
Hands-off: The leader trusts (or hopes) talented people will figure it out. It feels like a safer way to avoid being a micromanager, but over time it becomes isolating.
Neither approach works in every situation.
The leaders I see succeed learn when to lean in and when to step back.
What Experienced Leaders Still Need
Experienced leaders rarely need someone to teach them fundraising strategy, campaign management, or donor engagement.
What they often need is help understanding how your institution works.
Every organization has its own culture, decision-making processes, power dynamics, and expectations. Without that context, even highly capable leaders can struggle to gain traction.
When I Learned This the Hard Way
Early in my own leadership, I didn’t recognize the signs to let go of closely guiding a new manager. She was ready to operate more autonomously, but I kept providing structure that no longer served her. I unintentionally held her back—and it held me back, too. She didn’t need oversight; she needed my trust.
Later, I assumed a manager I’d hired with years of experience could navigate a new scope of authority without much from me. Her team unraveled under the weight of unclear expectations. By not more closely coaching her, I played a role in that.
Those experiences taught me the cost of leading without considering where the leaders were in their roles and careers, and what approach could best support them. Leaders understand there’s a spectrum of what’s needed from them—and they adjust. The right support at the right time builds thriving leaders and high-performing advancement teams.
When someone struggles or stalls, check whether you’re over-leading or under-leading for where they are now.
Recognizing where each person is—and responding with intention—becomes a discipline when you have the right framework.
How to Determine What Approach Is Needed
Before you decide how much direction or autonomy to give, pause and ask:
Is this person new to the role, even if they aren't new to leadership?
What strengths have made them successful and what new skills does this work require?
What context am I holding that would help them succeed faster?
What would help them most right now: direction, coaching, or space?
These questions help you move beyond your default style and lead the person in front of you where they are.
We also use the Hogan Assessment in our executive advisory work to help identify what drives each person, how they respond under stress, and what keeps them motivated. That data gives you language and clarity so you can flex your leadership with intention.
Use curiosity—not assumption—to decide how much guidance or freedom to give.
Adaptive Leadership in Practice
Traditional leadership models often present clear categories—directing, coaching, supporting, and delegating. At Hocking Leadership, we believe leadership is less about fitting into boxes and more about meeting the moment you’re in.
Think of this as a Clarity-to-Autonomy Continuum:
You start by providing structure and direction when the person or project is new.
You coach as confidence builds and understanding deepens.
You support as they take greater ownership but still need a thought partner.
You step back when trust and capability are firmly in place.
Sometimes the same team member will need clarity on Monday and autonomy by Friday on one project but may need more coaching on another project that’s newer to them. The work evolves, and so does your leadership.
The goal isn’t to progress linearly or perfectly. It’s to stay attuned to what’s needed in the moment and to adjust before the gap between your leadership style and their needs grows too wide.
Your adaptability—more than your expertise—is what multiplies your team’s results.
Common Stuck Points (and Better Moves)
Assuming tenure equals readiness
Someone you’ve known for years earns an internal promotion. Because they’ve been in the organization, you assume they’ll run on autopilot. In reality, they’re starting in a new role and need clarity from you early on—decisionmaking power, expectations, and what success looks like.
Defaulting to “do as I say” under pressure
Big goal, short timeline, team not meeting expectations—it’s tempting to hand out task lists. Directing everything keeps the work on your plate long term. Instead, set the outcome clearly and walk with them through the first steps. Then step back.
Avoiding clarity to seem empowering
You don’t want to micromanage, so you leave the path vague. Autonomy doesn’t mean absence. Mutually agreed-upon check-ins, specific milestones, and clear feedback create alignment and trust.
Expecting new executives to “just know”
That AVP you hired may have run teams before, but they still need to know your expectations and how authority flows here. Give them the playbook before you hand them the ball.
Assuming experience replaces context
An experienced leader knows how to lead. They don't automatically know how leadership works here. Before stepping back, ask yourself what institutional knowledge you're holding that would help them succeed faster.
Leadership adaptability means choosing your moments and methods with intention.
Your Adaptable Outcomes
Studies show that leaders who intentionally adapt their management approach are more likely to exhibit higher team engagement. In my work with advancement executives, that engagement translates directly into stronger fundraising outcomes and employee retention.
When you support people the way they need it, they know what’s expected, feel supported, and rise to challenges faster. You protect yourself from both burnout and the “hero leader” trap where every answer has to come from you.
Great leaders create clarity, context, and space for people to rise—and then adjust as they grow.
If you’re preparing for your own next big goal—a campaign, a new VP role, a newly reorganized team—and want to lead with clarity and adaptability, message me to schedule a confidential 20-minute conversation about how we can partner.
