Why sparing someone's feelings can undermine trust
The surprising power of being direct
BY
Jessica Wilen, Ph.D is an executive coach and the founder of A Cup of Ambition, a popular newsletter about working parenthood, the psychology of work, and women in leadership.
Leaders known for their emotional intelligence often pride themselves on cultivating trust, psychological safety, and genuine connection with their teams. These are essential assets in any leadership toolkit, particularly in environments that rely on collaboration, creativity, or mission alignment.
But inevitably, there are moments when these strengths—empathy, warmth, patience—need to be supplemented with something sharper: clarity, candor, and the ability to speak directly when the situation calls for it.
If you lead with empathy, you may already be adept at sensing how people are feeling and anticipating the downstream consequences of your words. But in certain moments, the harder leadership move isn't to hold space. It's to draw a line and provide someone a necessary reality check. Conversations like these often feel uncomfortable, but they ultimately serve the integrity of your team, your organization, or the individual themselves.
Confusing directness with harm
Many conscientious leaders hesitate to be fully direct because they conflate honesty with harshness. The fear is understandable: no one wants to be perceived as punitive, cold, or unfeeling. So we delay giving feedback—hedging our language and prioritizing emotional comfort over organizational clarity.
But avoiding the truth rarely protects people—it usually disorients them.
What erodes trust over time isn't directness; it's the absence of it. It's the vague feedback that leaves a team member guessing. The unspoken performance concern that festers behind the scenes. The dissonance between what's said in public and what's whispered in private.
Said differently: kindness without clarity is often just misplaced anxiety.
Directness as a form of respect
When a performance issue arises or a behavioral pattern needs to shift, it's worth asking: What does this person deserve to know?
Assuming your intent is constructive—not punitive—being direct is a sign of respect. It assumes the person is capable of hearing hard truths and of responding thoughtfully. It also models the type of culture most high-performing teams want: one where feedback is not weaponized, but neither is it avoided.
A few ways to ground a direct conversation in professionalism and respect:
'I want to have a conversation that's candid, because I take your role and your contribution seriously.'
'This might be hard to hear, but I trust your ability to receive it—and respond in a way that reflects your strengths.'
'I'm raising this because I value your place on the team and I want to make sure we're aligned moving forward.'
This kind of framing can't mask a poorly handled message—but it can open the door to a conversation grounded in mutual respect, rather than defensiveness.
Delivering clarity without cruelty
A direct conversation should be just that—direct. That means no extended preamble, no hedging language, no passive-aggressive tone. Say what you need to say plainly, and without dramatizing or editorializing.
Consider this structure:
Signal the conversation's purpose: 'I want to give you some candid feedback about how you're showing up on the team.'
Name the issue specifically: 'You've missed several key deadlines this quarter, and it's created ripple effects for others.'
Explain the impact: 'People are waiting on your contributions, and timelines are slipping. It's affecting morale.'
Invite dialogue: 'I'm curious how you're seeing this—do you agree with that assessment?'
Identify a clear next step or standard: 'We need to see improvement over the next month, and I'm happy to support you—but the expectations are non-negotiable.'
This approach allows you to balance accountability with collaboration. It removes ambiguity while still inviting the other person into the solution.
Anticipate discomfort—but don't personalize it
Even a well-structured conversation may evoke a strong emotional response: frustration, embarrassment, disappointment, defensiveness. This is part of the process—not an indication you've mishandled the exchange.
Resist the urge to over-explain, soften your message mid-stream, or rush in to repair the other person's reaction. If the message is true and necessary, the short-term discomfort is a feature of the process, not a bug.
One helpful internal reframe: This may feel hard, but that doesn't mean it's harmful. It means it matters.
Of course, how you follow up also matters. If the person is emotionally reactive or distressed, you can acknowledge the emotion without retreating from the content. A simple 'I know that was a lot to take in—let's revisit this in a few days after you've had a chance to reflect' can provide space for integration while still maintaining accountability.
Clarity shapes culture
Handled well, these conversations aren't just about individual performance—they shape your organizational culture. When feedback is delayed, filtered, or inconsistently delivered, teams become unclear about what's expected, what's tolerated, and what success actually looks like.
Conversely, when leaders are willing to say the hard thing—with steadiness and respect—it signals that performance standards matter, and that team dynamics are worth protecting.
Direct communication becomes an act of stewardship: protecting the integrity of the organization, safeguarding the cohesion of the team, and supporting the growth of the individuals within it.
Final thought
Some people are naturally more direct; others more sensitive to tone and relationship dynamics. But having hard conversations isn't about personality—it's about discipline. It's a practice. And like any other leadership muscle, it gets stronger with use.
For the empathic leader, the goal isn't to stop caring or to suppress emotional intelligence. It's to channel those qualities into a leadership style that's both principled and effective.
The best leaders don't choose between empathy and clarity. They hold both. And they have the courage to speak candidly—even when it's uncomfortable—because they understand that clarity is what allows empathy to be sustainable over time.
ABOUT THE AUTHOR
Jessica Wilen, Ph.D., is a trusted partner to top-tier leaders and organizations looking to elevate their leadership, strengthen teams and cultivate sustainable, high-performing cultures. As a member of the Fast Company Creator Network and author of the popular newsletter, A Cup of Ambition, Jessica writes about working parenthood, the psychology of work, and women in leadership. More
Hashtags
Try Our AI Features
Explore what Daily8 AI can do for you:
Comments
No comments yet...
Related Articles
Skift
6 minutes ago
- Skift
5 Reasons Off-Site Meetings Fail
Dr. Joe Allen, professor of industrial and organizational psychology at the University of Utah and director of the Center for Meeting Effectiveness at the Rocky Mountain Center for Occupational and Environmental Health, believes that a major reason many off-sites fall short is there's not enough education at the college level. 'I always challenge people to find me a course on meetings at a business school, and no one has ever found one for me. 'We do not train people on how to attend meetings and how to lead meetings. And yet, 75% of people's time is spent on meeting related activities if they're a manager or higher up in larger organizations — either attending, leading, or preparing for meetings.' Allen, who has written 200 articles in academic publications, several books including Running Effective Meetings for Dummies, and is involved in the planning of academic conferences ranging from 200 to 5,000 people, keeps seeing the same common mistakes — and offers some solutions. 1. They Don't Have a Mission for the Meeting 'You need to start with a particular goal or goals at the outset of planning,' Allen said. 'What are you trying to accomplish? Before you make decisions, you should go back to the goals you listed and say, 'Okay, how will this help us accomplish that?' and use that as a litmus test for all the different activities, all the different meetings, all the different talks — basically everything on the program.' 2. They Focus Too Heavily on Logistics 'With off-sites in particular, the focus is always on things like getting people to the location or making sure there's the right food,' he said. 'In my interviews and research, the post-meeting comments are always about the destination and the experiences people had. They often talk about how the meeting was great, but it really didn't accomplish a whole lot.' Among the questions he suggests meeting organizers ask from the start: What is the structure of the meeting? Who are you going to put in a room together, or assign to work on a process together? And how exactly are you going to do that? 3. They View Speakers as Entertainment 'When you're bringing in outside speakers, are you doing so for the right reasons?' he asks. 'I've advised people who are about to drop a good amount of money that the speaker might be a really big name and you'll hear some cool stuff, but how is it going to help their business?' 4. They Don't Connect Teambuilding to the Work Environment 'Teambuilding often misses the mark because the further it is away from what you actually do day to day, the harder it is to transfer that to the real world workplace,' Allen said. 'Take something like Space Camp [which does custom corporate training programs]. Doing collaborative activities together in that environment, it's going to be really tough for people cognitively to transition what they have learned.' There's one thing that helps, he says: 'If you immediately go from that to a setting right on site where you can discuss what you did there and how it translates into your work environment, you can get some of the benefits.' 5. The Networking is Not Intentional or Inclusive 'When it comes to traditional networking, there's a bias in favor of people of a certain personality type. When you've got an open bar and people are mingling around, the people who are generally more extroverted are going to be more capable of introducing themselves and making new connections. People who are a little more introverted are going to struggle with that. 'What we have found is that structuring networking by giving people different tasks to do elevates the experience for the introverts. It forces them to be a little bit uncomfortable, which they don't like, but also helps them to be more engaged, and to participate and meet new people.'
CBS News
7 minutes ago
- CBS News
Orphaned bear cubs rescued from Calaveras County neighborhood
A litter of bear cubs seen wandering a Calaveras County neighborhood alone have been taken in by wildlife rescuers in Southern California. The San Diego Humane Society says the three cubs were spotted over the course of several days. With no mother in sight, the cubs were rescued by the California Department of Fish and Wildlife and then taken to the San Diego Humane Society's Ramona Wildlife Center. Officials say the cubs, two males and a female, were about six to seven months old. Rescuers euthanized one of the cubs after finding it had bone defects and a BB pellet embedded in one of her paws. The other two cubs are now settling into their rescue habitat with the goal of minimally invasive care to avoid the animals from bonding with humans.
CBS News
7 minutes ago
- CBS News
Baltimore building demolished after partial collapse
A building in downtown Baltimore was demolished Monday after it partially collapsed, prompting concerns about its dangerous condition, according to Fire officials. The incident caused road closures, which impacted the morning commute for some. The vacant building in the 300 block of N. Eutaw Street – near Baltimore's historic Lexington Market – partially collapsed on Sunday. Baltimore fire crews arrived to find the building in a dangerous condition, prompting concerns about further collapse. According to city and state records, the building was constructed in 1890. The building was located between another vacant building and an occupied building that had to be evacuated, according to Baltimore City Fire spokesperson John Marsh. Multiple buildings were involved in the partial collapse, he said. No injuries were reported. Firefighters condemned two of the buildings. On Monday, inspectors and structural engineers surveyed the two buildings. Later in the day, the red building that had partially collapsed was completely demolished. There is an ongoing investigation to determine the cause of the partial building collapse and the extent of the damage. By Tuesday morning, gates surrounded sections of the building. The area is a few feet away from the Lexington Market retail district, and the demolition caused disruptions to foot traffic near the businesses. The Maryland Historical Trust said this part of the city is known as the Market Center Historic District, and served as the city's retail core for more than a century. On Monday, trains reduced their speed near the Lexington Market Station, and by Tuesday, they resumed regular operations.
