How to Lead Through Uncertainty: What the Best Executives Actually Do

We are in chaotic times on many levels. For most business leaders right now,
uncertainty isn't a phase. It's the operating condition.
Market volatility, AI disruption, shifting workforce expectations, economic headwinds —
the list of pressures facing executives at mid-market companies has never been longer
or more simultaneous. And yet some leaders consistently hold their organizations
together, keep teams moving, and come out of turbulent stretches in a stronger
competitive position. Others freeze, over-correct, or lose their teams' confidence
entirely.

The difference rarely comes down to information. It comes down to specific skills,
habits, and frameworks that most companies never formally teach.
Three Wisory Advisors — executives who have led through airline crises, corporate
restructurings, and media consolidations — share their experiences on what has
worked for them when the ground is moving.

Why Leading Through Uncertainty Is Different From Normal Leadership

Traditional leadership development assumes a relatively stable operating environment.
Leaders are taught to plan, execute, and measure. Uncertainty breaks that model.
Plans become obsolete before they're implemented. Measurements lag behind the
reality they're meant to capture. Teams look to leadership for signals that the standard
playbook can't provide.

What changes in uncertain environments isn't the fundamentals of leadership. It's the
specific capabilities that get tested most. Communication that used to be sufficient
becomes inadequate. Decision-making frameworks built for stable conditions start
producing wrong answers. The relationship between a leader and their team gets
stressed in ways that don't show up during normal operations.

The executives below have all been in those conditions. Their frameworks aren't
theoretical. They're what actually held their organizations together.

1. Stop Trying to Eliminate the Chaos — Build Systems to Operate Inside It

Jackie Yeaney has held CMO roles at Delta Airlines, Tableau, Red Hat, and Ellucian.
She now sits on two public company boards and coaches approximately fifteen C-level
executives on leadership and organizational dynamics.

Her first observation about leading through uncertainty is about the instinct that derails
most leaders before anything else.

Jackie worked with a client who was burning energy trying to make her environment
calmer and more routine. Yeaney's advice: stop. The goal isn't serenity. It's developing
the systems to operate at full capacity while the ground is moving.

As Jackie states: "I don't believe the chaos is going to get better. We have to figure out
the mechanisms of dealing with it better, not of getting rid of it."

Most leaders waste significant energy trying to restore stability before they allow
themselves to lead effectively. They treat uncertainty as a problem to solve rather than a
condition to operate within. The result is delayed decision-making, inconsistent
communication, and a team that reads the hesitation and amplifies it.

Her framework: projecting calm while still projecting urgency. Because both are true at
once. If leaders show visible anxiety, the whole organization mirrors it. If they're so
composed that nothing feels urgent, teams stop moving with the speed the situation
requires. The leaders who hold teams together during uncertainty aren't suppressing
their awareness of the problem. They've developed the discipline to hold two signals
simultaneously and transmit the right one.

"Stop beating yourself up over things you can't control," she says. That's not a soft
observation. It's a precise description of where leadership energy gets wasted most in
uncertain times.

The practical application for mid-market leaders: Audit where your leadership energy is
going. If a meaningful portion of it is directed at trying to make the environment more
predictable rather than building the capacity to operate within an unpredictable one, that
allocation needs to change.

2. Communicate Clearly Before You're Ready — Because Silence Has a
Cost

Soni Basi is a seasoned CHRO who has served at large organizations including
Allergan, AIG, Estee Lauder, and Edelman — most of them mid-transformation when
she arrived. Her read on what actually holds organizations together during volatile
periods is one word: clarity.

"When there's a rumor mill, it's a really unhealthy culture," she says. "You can either be
addressing it head on or you can let people make their own assumptions."
Silence from leadership during uncertainty doesn't read as neutral. It reads as bad news
being withheld. Teams don't sit in ambiguity — they fill it. And what they fill it with is
almost never accurate, seldom helpful, and consistently harder to undo than the original
message would have been.

The clarity Soni describes isn't false confidence. It isn't telling people things are fine
when they aren't. It's being specific about what is known, what isn't, and what the
organization is doing about the gap. That kind of communication takes more courage
than most leaders expect, because it requires speaking before you have all the
answers.

"Culture can either be an accelerant to what you're working to accomplish or it can be a
major drag," she says. In uncertain conditions, that variable almost always traces back
to whether leaders communicated honestly when it was uncomfortable to do so.

The practical application for mid-market leaders: In periods of uncertainty, increase your
communication frequency before your instinct tells you to. The cost of
over-communicating is almost always lower than the cost of the assumptions that form
in its absence.

3. Build the Relationships That Make Honest Thinking Possible

Jim Fielding is a legendary leader in the consumer and retail space. Jim spent twelve
years at Disney, including four as President of Disney Stores globally, before becoming
CEO of Claire's and then President of DreamWorks and 20th Century Fox Consumer
Products. He has led through media consolidations, pandemic shutdowns, and
institutional uncertainty at some of the largest consumer brands in the world.
His most consistent observation across all of it: the leaders who hold up best in
uncertain times are not the ones who have the most answers. They're the ones who
have built the relationships that make honest thinking possible when they don't.
According to Jim: "The best kind of leader is the one who can raise their hand and say, I
need help. That's huge strength."

He means this operationally, not philosophically. When he was CEO of Claire's, he
joined the Chicago CEO Society specifically to find peers who understood what the role
felt like from the inside. Throughout his time at Disney, DreamWorks, and Fox, he kept
coaches and trusted advisors in regular contact. His reason was straightforward:
leadership at that level is structurally isolating.

"You don't really have a peer in the company," he says. "Everyone reports to you."
Isolation is where bad decisions get made, where blind spots go unchallenged, and
where the small miscalibrations that compound into large problems go unnoticed
longest.

The other quality Jim looks for in the leaders he now works with is what he calls
helicopter ability: the capacity to operate strategically at altitude and get tactical on the
ground, and to read which altitude the current moment requires. In uncertain
environments, that range isn't optional. Leaders who can only operate at one level tend
to be either too slow or too reactive when conditions shift.

As Jim states: "Hover at the strategic level, but when needed, swoop down and get
tactical."

The practical application for mid-market leaders: Map your current sounding board
honestly. Who in your network has the context, the candor, and the relevant experience
to give you genuinely useful input on the decisions you're facing right now? If the honest
answer is "not many people," that's the most important gap to close before the next
difficult period arrives.

Three Leadership Capabilities for Navigating Uncertainty

Based on the frameworks these three executives use in their advisory and coaching
work, these are the specific leadership capabilities that most directly determine
performance in uncertain times:

1. Dual-signal communication: The ability to project calm and urgency
simultaneously, so teams neither panic nor stall.

2. Proactive clarity: Communicating what is known, what isn't, and what the plan is
before the absence of information creates its own narrative.

3. Structural self-awareness: Recognizing that leadership isolation is a feature of
the role, not a personal failing, and building the relationships that compensate for
it intentionally.

None of these are truly innate. All of them are learnable. And most of them can be
developed faster and better with someone who has already led through the challenge
you're facing.

The Bottom Line on Leading Through Uncertainty

The leaders in this piece haven't navigated uncertainty by being more certain. They've
developed specific capabilities — projecting calm without losing urgency,
communicating clearly before they were ready, and building the relationships that make
honest thinking possible when the stakes are high.

What separates leaders who thrive in these conditions from those who just survive them
isn't experience alone. It's access to frameworks, relationships, and perspectives that
most leaders can't build inside their own organizations.

Work 1:1 with a Wisory Advisor on Your Leadership Challenges

The pressures facing executives at mid-market companies right now are real, specific,
and rarely solved by generic leadership content. What moves the needle is a
conversation with someone who has faced the same category of problem at the same
level of stakes.

Wisory members get 1:1 access to executives like Jackie, Soni and Jim — at the
moment a decision matters most, not after it's already been made.

Explore membership at thewisory.com →

About the Advisors

Jackie Yeaney is a Wisory Advisor and former CMO of Delta Airlines, Tableau, Red Hat,
and Ellucian. She sits on two public company boards and coaches CMOs and senior
executives on leadership, board dynamics, and navigating organizational uncertainty.

Soni Basi is a Wisory Advisor and former CHRO at Allergan, AIG, Estee Lauder, and
Edelman. She advises mid-market companies on culture, talent strategy, and building
organizations that hold together through transformation.

Jim Fielding is a Wisory Advisor, former President of Disney Stores globally, CEO of
Claire's, and President of DreamWorks and 20th Century Fox Consumer Products. He
is an executive coach and author, and advises consumer-facing companies on
leadership, culture, and competing through periods of significant change.

Jackie, Soni, and Jim are available for 1:1 advisory sessions through The Wisory.
Members get direct access to executives like these, on the specific challenge, at the
moment it matters. Learn more and book time at thewisory.com.