When Aiden, the Chief People Officer (CPO) of a rapidly scaling tech startup, first joined the leadership team, he was excited to bring structure and strategy to a company that had doubled in headcount in less than two years. But within months, he noticed a troubling pattern: teams were bypassing their functional leaders and going directly to the founder and CEO, Michael.

At first, Aiden assumed this was the natural growing pain of a founder-led organization. But as he looked closer, the issue was more complex. Michael, though visionary and deeply invested in his team’s happiness, had a tendency to be a people-pleaser. When a group of engineers disliked the CFO’s directive requiring partial in-office work for regulatory and financial reasons, they didn’t raise the concern with the CFO. Instead, they went directly to Michael. Wanting to avoid conflict and preserve goodwill, Michael agreed with them on the spot, unintentionally undermining the CFO’s authority.

This cycle repeated across departments. Leaders would establish policies aligned with the company’s strategic needs, only for those decisions to be overturned, sometimes in casual hallway conversations, because Michael wanted to reassure employees. While well-intentioned, the CEO’s overstepping left the leadership team fractured, credibility strained, and employees confused about which rules actually applied.

People-pleasing tendencies in CEOs are not uncommon, especially in founder-led organizations where loyalty and culture are prized. But without boundaries, these habits can unintentionally destabilize the very leadership structure designed to support growth.

For business leaders like Aiden, the challenge isn’t just about managing their own function—it’s about managing up. The question becomes: how do you support a CEO who oversteps in the name of employee satisfaction, while ensuring other leaders maintain credibility and the company doesn’t drift into chaos?

Because objectivity diminishes the higher anyone goes in an organizational hierarchy, Aiden wasn’t getting objectivity. Fortunately, Aiden is in an executive mastermind group and those executives encouraged him to pursue the following steps:

High-performing leadership teams thrive on clear ownership. One effective approach is to create a “decision rights map” that makes visible which leader is accountable for which areas. For example, workforce policies might sit under the CFO’s purview, while the CEO provides input only at set review points. Codifying authority in this way helps employees understand where to direct concerns and reduces the temptation to bypass functional leaders.

When a CEO agrees too quickly to employee requests, leadership peers can step in to reframe the moment as an opportunity for alignment. A useful response is something along the lines of: “That’s an important concern—let’s make sure the relevant leader is looped in so it fits into the broader plan.” This keeps the CEO connected to employees while reinforcing the authority of the leader responsible for the decision.

To avoid conflicting directives, organizations can set up systems where employee concerns raised directly with the CEO are logged and routed back to the appropriate leader. This preserves the CEO’s role as approachable and empathetic, while ensuring that input is integrated into structured decision-making rather than creating confusion.

Sometimes a CEO needs help connecting the dots between short-term reassurance and long-term leadership credibility. Leaders can surface real examples—such as policies being ignored or authority eroding—to show how quick promises can undercut strategic goals. Framing the issue as a trust and alignment challenge, rather than a personal flaw, helps CEOs recognize the importance of consistency.

When these practices are in place, CEOs learn to respond differently: “I hear your concern, and I want you to know we value it. Let’s make sure the right leader is brought into the conversation so we can get this right.”

The result is a healthier leadership dynamic: credibility is preserved, employees know which channels to follow, and the CEO maintains their approachable style without undermining the authority of their team. Ultimately, these guardrails allow fast-growing companies to scale without sacrificing trust or clarity.

Fast-growing startups depend on both visionary leadership and operational discipline. When CEOs lean too heavily into people-pleasing, they risk undercutting the very leaders who drive sustainable growth. Business leaders who find themselves in Aiden’s position should remember: managing up isn’t about controlling the CEO—it’s about protecting leadership integrity and creating structures that allow empathy and authority to coexist.

When Maya Patel took on her new role as team manager at a fast-growing tech firm, everything seemed picture-perfect. The office radiated positivity with green plants adorned every corner, meetings ran smoothly, and her team of high-performing professionals appeared engaged and cheerful. Yet Maya couldn’t shake the feeling that something was missing.

Over time, she began noticing whispers in the hallways and closed-door conversations in small groups. Employees praised the company’s culture in public but privately expressed frustrations about inefficiencies, communication breakdowns, and missed opportunities. The concerns never reached team-wide discussions; instead, they simmered quietly.

Maya’s situation is not unusual. Many business leaders find themselves in organizations where everything looks flawless on the surface, yet undercurrents of dissatisfaction flow beneath. The challenge lies in addressing those undercurrents before they grow into cultural cracks.

Maya described her challenge as “two dogs barking through a fence.” On either side, energy and passion were evident, but the fence prevented resolution. Her team members weren’t voicing issues openly, so frustrations stayed contained within cliques. When she tried to intervene, the discussions quickly escalated into defensiveness rather than collaboration.

This metaphor captures a common leadership dilemma: when teams hesitate to bring up problems directly, managers often step into the role of mediator, sometimes with little success. Without a clear path for open dialogue, teams can appear harmonious while failing to address what truly holds them back.

Maya’s experience highlights strategies any business leader can adopt when facing a seemingly “too perfect” team culture that hides unspoken tensions.

Leaders must create psychological safety where team members can voice concerns without fear of judgment. Regularly reinforcing that constructive criticism is valued, not penalized, opens the gate for dialogue.

Maya implemented monthly “pulse check” sessions where every team member was invited to share one challenge and one improvement idea. Framing this as part of continuous improvement made it clear that speaking up was not only acceptable but expected.

Private grumbling was redirected into collective brainstorming. Maya encouraged employees to bring concerns with at least one suggested solution. This shifted conversations from venting to action-oriented dialogue.

To reinforce trust, Maya prioritized acting on small but meaningful suggestions quickly, whether it was streamlining a reporting process or clarifying project ownership. Demonstrating responsiveness signaled that voicing issues led to results.

By facilitating cross-group discussions, Maya ensured concerns were addressed directly rather than passed around in silos. She often played the role of translator, reframing complaints into neutral, solution-focused language that allowed both sides to listen productively.

Within a few months, Maya’s team began shifting from guarded perfection to authentic collaboration. Employees no longer felt the need to whisper frustrations in hallways. Instead, they trusted that their voices would be heard and that their input could shape team practices. The metaphorical fence came down, not by silencing the barking, but by giving both “dogs” a safe yard to meet face-to-face.

For business leaders, the lesson is clear: a team that looks perfect on the outside may be struggling with unspoken tensions underneath. By creating structures for honest feedback, modeling openness, and acting decisively on what is shared, leaders can transform hidden dissatisfaction into shared growth.

Maya’s journey demonstrates that handling complaints isn’t about preventing barking—it’s about opening the gate. When leaders replace silence with structured dialogue, they build teams that are not only high-performing but also resilient, authentic, and ready to innovate together.

In early March, weeks after a difficult round of layoffs at Finverity, a mid-sized fintech firm based in Austin, Chief Operating Officer Daniel Kim sat quietly in his office, reviewing an email draft for the third time. The company had just let go of 40 employees, nearly 20% of its workforce, as part of a necessary restructuring. On paper, the move secured another 18 months of runway and realigned Finverity toward its most profitable tools. But the human cost was palpable.

The halls were quieter. Slack messages had taken on a colder tone. Managers reported a sharp decline in employee engagement, and HR flagged an uptick in anonymous feedback about "leadership silence" and burnout. For the employees who remained, trust had cracked. Daniel knew the numbers looked better, but culture, morale, and credibility had taken a hit.

This was the moment Daniel decided to stop focusing solely on operational recovery and start leading the emotional one. 

When layoffs occur, many leaders default to generic statements: “We’re realigning resources,” or “This wasn’t an easy decision.” A short internal memo is sent out, a brief all-hands is held, and then leadership often attempts to return to business as usual.

But “business as usual” rarely exists after a layoff.

The absence left behind isn’t just about empty desks or missing team members, it's about the emotional and psychological aftermath. Employees are left with unanswered questions: Am I safe? Why were certain people let go? Could this happen again? What does this say about our future?

Layoffs fundamentally alter workplace dynamics. They often introduce:

Without open, ongoing communication from leadership, that silence gets filled by speculation, anxiety, and worst-case assumptions. What could have been a moment of unity becomes one of fragmentation.

Don’t rush into “getting back to normal.” After a layoff, what was “normal” no longer exists. The emotional toll is real grief, guilt, anxiety, and distrust often simmer beneath the surface. The worst thing a leader can do is ignore it.

Instead, create intentional space for open dialogue. Host team check-ins where employees are encouraged to share how they're really feeling, and not performatively, but authentically. Acknowledge the loss, validate the discomfort, and resist the urge to pivot too quickly into productivity talk.

Layoffs are not just operational events—they are emotional ones. Leaders must create space to process burnout, fear, and grief. Hold honest conversations, not to fix things immediately, but to listen. This can happen through small-group meetings, anonymous feedback tools, or one-on-one check-ins. Most importantly, leaders should reaffirm their commitment to the remaining team through visible, ongoing action—not just reassuring words.

After giving space to reflect, teams need a new direction. Avoid forced optimism and instead focus on building a future grounded in clarity. Reframe the internal message from what was lost to what is now possible. Use forward-looking language like “Here’s where we’re headed,” or “This is how we’ll rebuild together.” A vision workshop or all-hands Q&A can reinforce alignment and give employees a sense of purpose in the new chapter.

Buy-in grows when people feel ownership. Invite departments to co-create goals, and connect their work back to the company’s mission. When people can see how their role fits into the bigger picture, engagement follows. Empower team leads to facilitate planning sessions that allow input from all voices—not just top-down directives.

Morale isn’t rebuilt through pizza or ping pong—it’s rebuilt through trust and real conversation. Host “Reconnection Days” or off-site sessions that focus on culture, values, and vision. Drop the presentations. Instead, prompt teams to reflect on what they want their culture to feel like moving forward. These gatherings should prioritize honesty and shared understanding—not performance metrics.

Rebuilding trust is a process, not a moment. Leaders must regularly check the pulse of their teams through surveys, anonymous feedback, or town halls. Share progress transparently—what’s improving, what still needs work, and what’s being done about it. Celebrate small wins, especially moments of collaboration or resilience. Progress may be slow, but consistency builds momentum—and that momentum restores belief. Using tools such as AIM Insights can help with tracking and reinforcing progress.

In the months that followed, Daniel Kim didn’t just regain the confidence of his team, he helped redefine what leadership looked like in a post-layoff workplace. By choosing transparency over distance, dialogue over damage control, and shared purpose over performative perks, he reminded his company that trust isn’t rebuilt through strategy decks, it’s earned through presence, honesty, and follow-through.

 For leaders navigating the difficult terrain after a restructuring, the lesson is clear: the business may survive the layoff, but the culture only survives if you lead what comes next with heart.

On the surface, Maya seemed to have it all under control. As CEO of Vireon Labs, a fast-growing AI-driven data analytics firm, she was known for her composed presence in boardrooms and her fierce commitment to innovation. Investors praised her strategic vision. Employees admired her sharp decisiveness. But beneath the calm surface, Maya had been grappling with a quietly growing concern: the company’s churn rate for enterprise clients had increased over the past two quarters, and recent customer feedback suggested dissatisfaction with post-sale service.

It wasn’t a crisis yet, but it could be. Then came the investor call that dropped the curtain. 

During a routine quarterly meeting, one of Vireon Labs’ long-standing investors raised concerns about declining client retention and recent dissatisfaction from referred accounts. The question caught Maya off guard. While she had seen the warning signs of the rising churn rates and lukewarm feedback, there wasn’t yet a concrete solution in place.

Instead of deflecting, Maya acknowledged the issue head-on. She recognized the gap, explained that the leadership team was aware of it, and committed to making it a top organizational priority. Her response was honest and unguarded, a clear shift from the polished answers typically expected in investor settings.

Surprisingly, the investor welcomed the transparency and expressed openness to working through the next steps together. Rather than losing confidence, the admission became a starting point for deeper alignment and collaboration.

What Maya demonstrated in that moment wasn’t a lapse in leadership; it was strategic vulnerability.

In many organizations, vulnerability is still viewed through a narrow lens: as weakness, oversharing, or a lack of control. But in reality, when vulnerability is paired with accountability and clarity of intent, it becomes one of the most powerful levers a leader can use to foster trust, unlock collaboration, and drive meaningful change.

In Maya’s case, acknowledging she didn’t have a fully formed solution didn’t erode her credibility; it strengthened it. By confronting the issue head-on, she signaled to both investors and employees that honesty would take precedence over image management. She took full ownership of the gap, but she didn’t shoulder it alone. Her candor invited others into the problem-solving process, creating space for shared responsibility and engagement.

In the broader workplace, vulnerability plays a similar role. When leaders are open about challenges, whether it's slipping metrics, internal friction, or external market shifts, they create a culture where truth can surface without fear. That transparency fuels psychological safety, the foundational element of high-performing teams.

Moreover, vulnerability accelerates alignment. Rather than wasting time on maintaining appearances or managing assumptions, teams can spend their energy addressing root causes. It builds resilience by normalizing adaptive problem-solving over perfectionism.

In today's rapidly shifting business environment, where complexity and ambiguity are constant, vulnerability isn’t just an emotional quality; it’s a strategic necessity. Leaders who embrace it set the tone for agility, accountability, and authentic connection, all of which fuel long-term performance. 

Vulnerability in leadership doesn’t end with the admission of a problem; it begins there. Leaders who know how to move from honesty to execution can use vulnerability as a launching pad for cultural transformation and business results. Here’s how:

The first and most critical step is to name the issue with clarity. Avoiding euphemisms or downplaying the problem sends mixed signals and creates confusion. When leaders are direct about what’s going wrong, they foster alignment around what needs to change. Clear articulation of the problem ensures that everyone in the organization is solving for the same thing and understands its importance to the business.

Once the issue is identified, it must not be treated as the responsibility of one team or individual. When top-down directives follow transparency, it often limits creativity and isolates the burden. But when leaders distribute ownership and emphasize that the issue affects the broader organization, they invite cross-functional collaboration and more diverse problem-solving perspectives. For instance, if customer retention is declining, that may stem from issues in sales handoffs, onboarding, product usability, or customer support. Collective momentum builds when each group understands how its work influences the outcome.

Vulnerability at the top sets a tone, but it needs to be matched by psychological safety at every level. For transparency to translate into traction, employees must feel safe speaking up about what isn’t working. If team members fear backlash or judgment, critical insights remain buried. It involves consistent behaviors, asking for input before solutions are drafted, publicly recognizing those who raise concerns early, and responding constructively to hard feedback. 

To avoid stalling in analysis or endless meetings, leaders should introduce structure through a focused, time-bound discovery phase. A sprint format, typically lasting 2 to 4 weeks, allows organizations to explore root causes quickly and collaboratively without disrupting day-to-day operations. During this period, cross-functional teams can gather data, conduct interviews, map processes, and identify systemic gaps. It’s important to assign a facilitator or project lead to maintain momentum and synthesize findings. At the end of the sprint, teams should deliver insights and proposed next steps in a format that drives action, not just discussion.

Transparency becomes transformational when it leads to change. The final step is translating the insights from the discovery sprint into specific, measurable improvements. These actions should be prioritized based on impact and feasibility, and communicated widely to the organization.

Leaders must establish clear accountability for implementation, set timelines, and track progress against defined outcomes.

Months later, when stakeholders revisited the issue, the conversation looked very different. It wasn’t just about metrics or performance updates; it was about progress and perspective. What had shifted most wasn’t just the numbers and how the company approached challenges.

Rather than trying to have all the answers from the outset, the leadership team had embraced a new rhythm: one centered on open dialogue, faster iteration, and shared accountability. The organization had become more agile, not because every issue was solved perfectly, but because problems were addressed more collaboratively and transparently.

In the end, the most valuable outcome of the experience wasn’t just operational, it was cultural. Vulnerability had become embedded in the company’s DNA, turning what could have been a liability into a long-term advantage.

On the surface, Micheal looked like a dream hire. As the VP of Technology at a fast scaling fintech firm, he moved fast, delivered faster, and held his team to exceptional standards. Colleagues praised his work ethic. The CEO trusted his judgment implicitly. Micheal didn’t just meet deadlines, he bulldozed through them, building systems that scaled and workflows that hummed with efficiency.

But there was something building slowly.

It wasn’t anything major at first. A bug in the product’s dashboard that should’ve been caught. A delay in a data migration project with no proactive heads up. A misconfigured server that took days to surface. These were minor errors, but they shared a troubling theme: no one knew about them until they became unavoidable.

Micheal’s instinct wasn’t to hide. It was to fix it. Quietly. Silently. After all, in his mind, owning mistakes was a weakness. Admitting fault would diminish his authority. The less leadership had to worry, the better. But that’s where the danger crept in: small mistakes left unspoken that compounded over time. And for a business growing fast, every day a mistake goes unaddressed is a day risk quietly metastasizes.

When Micheal chose not to surface small mistakes, he didn’t do it out of malice, he did it out of a sense of responsibility. But that sense of “I’ll fix it myself” gradually evolved into a pattern of withholding information. In a leadership role, withholding, even unintentionally, becomes dangerous not just for the team, but for the organization.

Delayed Visibility = Escalated Cost: What starts as a minor issue can quickly evolve into a major operational disruption when not surfaced early. Small bugs become cross functional fire drills simply because leadership wasn't informed in time.

Poor Data Leads to Poor Decisions: When issues are hidden, leaders make strategic decisions based on incomplete or inaccurate information which impacts everything from resource allocation to investor communications.

Silence Breeds More Silence: When a senior leader withholds problems, it sets a cultural precedent. Teams may follow suit, eroding trust and psychological safety. Without a culture of transparency, systemic risks go unnoticed until they explode.

When a high performing employee begins withholding mistakes out of pride, leaders must act quickly, but thoughtfully. Here's a clear 5 step approach to address the issue while preserving trust and performance:

Before assuming the worst, pull the employee aside, and have a transparent conversation of what is going on. It could be work related stress or a personal issue. Showing empathy, not suspicion opens the door for honest dialogue and signals that you care about the person, not just the output.

Dig deeper into why mistakes weren’t communicated. Avoid blame, instead, ask, “What made you feel like you had to handle this on your own?” Often, pride is a shield for fear or pressure. Use coaching to uncover the root cause and align on shared expectations.

Clarify that real leadership isn’t about perfection, it’s about visibility. Frame early communication as a strategic behavior. Then model it yourself. Share your own mistakes in team settings and how transparency helped prevent larger issues. This redefines what “strong leadership” looks like. Opening up to that vulnerability will also build a stronger relationship.

Build simple routines that make it easy, and expected, for your team to surface issues early. Something as quick as a weekly 15 minute “Red Flag Roundup” can give everyone a low pressure space to share blockers or risks. Pair these check ins with transparent performance updates so everyone knows how their work stacks up against expectations. When transparency becomes part of the rhythm, it feels safe and normal.

Make it a point to praise people not only for delivering results, but for speaking up when something’s off, even if they had a hand in the mistake. When someone flags a problem early, thank them publicly. This shows the team that being upfront isn’t damaging, it’s leadership. Over time, this reshapes the culture from “look perfect” to “work smart and stay accountable.”

High standards are an asset, until they’re paired with ego that discourages openness. Even top performers can become blind spots when they value perfection over transparency.

The takeaway for leaders is clear: Don’t wait for avoidable crises to expose cultural weaknesses. Create an environment where speaking up is rewarded, not penalized. Redefine strength as accountability, not invincibility. Because in business, it’s rarely the initial mistake that causes the most damage; it's the silence that follows.