Things You want to Tell to your Boss but Can’t

8 min readOct 31, 2020


Photo by Ricardo Mancía on Unsplash

“What would you like to tell your boss but are afraid to share?”

A simple question can turn silence into insights. There are a lot of things that employees are thinking, but wouldn’t ever dare to tell their bosses.

As a cultural transformation consultant, I spend a lot of time talking to — and observing — teams behind the scenes. Every time they bring up a concern, my immediate reaction is, “Have you shared this with your boss?”

Of course, people give me a strange look, laugh at me or simply ignore the question.

Chances are, they don’t feel the culture is safe; people are afraid of getting fired, or consider their boss to be intimidating. Whatever the reason, how can leaders fix a problem if they don’t even know it exists?

We’ve uncovered many recurring themes by talking to thousands of team members. Here are the top seven things people would love to tell their bosses.

1. We Are Afraid to Speak Up

Unfortunately, fear is a pervasive emotion in most organizations. Not speaking up is how people adapt to survive potential attacks — they prefer being ignored to being criticized. Most leaders don’t pay attention to silence. They assume things are fine.

Most organizations have a silence problem — the truth is forced underground. A study by Milliken & Morrison shows that 85% of employees feel unable to raise a concern with their bosses. Management has to rely on rumors, gossip or insincerity.

“When I’m asked to share my opinion, I feel like walking on eggshells.” — VP of engineering

Fear paralyzes us but also filters our behavior — we choose the safe path, not the right one. Psychological safety — the shared belief that a team is safe for interpersonal risk-taking — is essential to drive collaboration, decision-making, and innovation.

Sounds easy and obvious, right? However, leaders tend to ignore symptoms, no matter how evident. They don’t pay attention to the silence, neither listen to the powerful voices of quiet people. Even when we share our findings from both surveys and interviewing people, some leaders don’t want to admit their teams are afraid.

“This is not what I observe.” — The initial response is skepticism, followed by denial. This reaction is a bit annoying, especially because I see this happening very often.

Organizations can’t build a fearless culture — where people feel safe, and silence is no longer needed — if they don’t first recognize they have a fear problem.

2. Don’t Take Feedback Personally

A parents-teachers conference is an excellent opportunity to practice empathy. As someone obsessed with human behavior, I like to observe things from a distance. Teachers usually measure their words and try to get approval from parents — they want to avoid emotional outbursts.

Most parents seem to be looking for validation, not feedback. They want to hear their children are great, not that they have “areas of opportunity.” CEOs experience a similar behavior — just like parents, they struggle to tolerate constructive criticism. They take it personally.

Three key things block feedback according to Douglas Stone & Sheila Heen, the authors of Thanks for the feedback: truth, relationship, and identity triggers. When we feel attacked, we shut down.

Identity triggers are all about us — we take feedback personally. We confuse the part (the feedback) with the whole (our identity). That’s because we associate our self-identity and reputation with the organization’s performance — if something is not working, we are to be blamed.

“Our CEO doesn’t want to hear anything negative.” — CHRO of Fortune 500

In this MIT Sloan piece, Adam Grant explains how the first barrier to change is resistance to new data. The “that’s not what my experience has shown” reaction makes executives immune to feedback. That a problem wasn’t detected before doesn’t mean it didn’t exist. Or it can be a new, emerging issue.

Rejecting ‘bad news’ harms your organization more than your self-image. You are not the company. It’s okay to feel pride and joy about your organization (or your kids). But, don’t let your love and passion ignore areas of improvement.

3. Who Makes the Call?

Decision-making is a recurring tension among organizations. People say they are not more proactive because they lack power. However, lack of clarity seems to be a bigger issue. Most people get stuck because they are unclear how decisions are made in their organizations — this could be an excuse or simply miscommunication.

Try this. Ask your team members to describe how they make decisions. Let each person write down their own ‘versions.’ Then, ask each person to share their notes with the rest. Surprised? I usually facilitate this exercise when I start coaching a new team. Most of the times, people share multiple approaches. How can a team align on a resolution if its members are not first aligned on how to come up with a decision?

“We don’t have a single approach to making decisions.” — COO of a CPG company

In a management survey, 98% of workers stated that an effective decision-making process should include input from everyone impacted by the decision. Yet, 40% of interviewees said that leaders continuously fail to ask theirs.

Involving people is key but having a clear process is even more important. Many organizations default to “consensus” in the absence of a clear decision-making approach. Maybe it’s a natural aversion to conflict and criticism.

A clear decision-making approach increases participation but also removes the excuses (“I don’t have the authority to decide that.” or “I prefer to wait because I don’t know how we make decisions here.”).

Clarity doesn’t mean defaulting to one single method. The nature and complexity of the different types of decisions require different approaches — autocratic, full delegation, democratic, consent, consultative, etc.

4. We Have Emotions — Pay Attention

Recently, I’ve been receiving a lot of calls from executives that want their organizations “to become more human.” While this is right in my ally, I’m skeptical at first. Many want to create a “purpose-driven” workplace without addressing their emotional culture.

Emotions, both positive and negative, are a fundamental part of who we are. Research shows that organizations that encourage people to be open about their emotions are more collaborative, productive, creative and tend to make fewer mistakes — particularly in high-pressure situations.

“My boss forgets we are human too.” — project manager, fast-growth startup

Organizations that tackle employees’ moods and feelings outperform those that ignore emotions or force people to suppress negative ones.

Herb Kelleher, the co-founder of Southwest Airlines, taught us that we don’t have to check your heart or your sense of humor at the office door. In his own words, “You don’t hire for skills, you hire for attitude. You can always teach skills.”

Make space for addressing emotions. Authenticity eats faked positivity for breakfast. As Sigal Barsade wrote, “Every organization has an emotional culture, even if it’s one of suppression.” Inhibiting feelings leads to a toxic process in our brain. Negative emotions are powerful signals — instead of silencing them, pay attention.

Your Emotional Culture Is Powerful — Just Listen

Teams thrive when emotions are not suppressed

5. We Want to Be Challenged by Our Work

Employees don’t just leave bad bosses or toxic cultures — they quit jobs that don’t challenge them.

Research by Gallup shows that more than 75% of employees believe their bosses don’t motivate their team to unleash their true potential.

An engagement survey by Facebook confirmed the same perspective. While the social media platform’s bet was on managers, the results told a different story. Employees leave Facebook because their job wasn’t enjoyable — they weren’t growing professionally or felt their strengths weren’t used.

“We want to feel challenged by our boss, not criticized.” — Sr. Analyst (Spain)

If you want to keep your best talent, pay more attention to how you design their work. Most companies force people into jobs that are pre-designed rather than adjusting roles to people’s talents. As Facebook’s research uncovered, the best managers do the opposite: “when they find talented people, they’re open to creating jobs around them.”

People thrive when they are challenged to give their best. Jobs are not functional as I wrote here — people want to work on something meaningful. And everyone finds meaning in different ways.

6. Stop Wasting Our Time

We have an addiction to meetings — and reports. There’s nothing wrong with either. Like most things, how we do them matters more than what we do. Meetings can be a time-waster or an effective way to move projects forward.

However, many organizations suffer from ‘mandatory’ meetings — most people feel compelled to attend even if they don’t add any value to the meeting (and the other way around).

“We waste our time doing that weekly report that no one cares about, except my boss.” — Sr Project Manager, global telco

Useless activities drain teams — they suck both time and passion. Having a clear purpose is key. Most people go to meetings without clear expectations of roles and outcomes. The same happens with analyses or tasks that are part of the culture — no one dares to challenge them.

The organizational uniqueness bias, as Adam Grant calls it, makes people work on autopilot. Some things must be done without questioning and others “will never work here.” That’s how leaders shut down improvement. They keep their teams busy with useless reports, inefficient meeting, or meaningless jobs.

Invite your team to the conversation. Get feedback on what’s working and what is a time waster. Identify essential tasks. Let people opt out of meetings — no one better than oneself to know where to focus own energy. Allow people to self-select teams and projects. Ask for input — prioritize meaningful tasks or meetings and get rid of those that don’t add any value. Check out this exercise.

7. Your Stars Are Crashing

Managers tend to see what they want to see. They reward functional performance but ignore leadership skills. That’s why most people that are promoted end being terrible bosses.

The halo effect occurs when managers have a hugely positive view of a particular employee. They see them as more extraordinary than they actually are — they miss to acknowledge areas of improvements.

“Our VP of social media is brilliant, but he’s clueless about how to lead people.” — Community manager (NYC)

There’s nothing wrong with rewarding people, but the leadership aspect must be addressed simultaneously. A star employee can quickly turn into a toxic manager crashing the entire team.

Basic management training and coaching can go a long way. Google was able to improve performance for 75% of its worst managers by helping them learn how to define a team purpose, take care of their people and stay results-oriented, among other things.

Ongoing feedback and open conversations help uncover team tensions. Don’t let the halo effect distort your perspective. Star employees can crash a team regardless of how bright they are if they don’t learn the basic management skills. Don’t overestimate top-performers and underestimate the rest.

Large organizational transformations are a hot topic — leaders are looking for a silver bullet to become more innovative, agile and adaptive. But, we forget that the most effective transformations happen from the inside-out. We must help our teams become the best version of themselves.

In my experience, small changes can create a big impact. Start by listening to what your team is trying to tell you, but are afraid to say. Most of the problems start and end with trust.

Gustavo Razzetti is a change instigator who helps purpose-driven organizations create positive change. Consultant, Author, and Speaker on team development and cultural transformation.