Soft Skills Are the Hardest Part of Leadership: Here’s How to Teach Them

Soft Skills Are the Hardest Part of Leadership: Here’s How to Teach Them

Posted by Feelings Found on

Written by Alexandra Dawson

 

Your Team Meetings Suck Because Your Managers Don't Know How to Feel

 

Let's get super real for a second. Because let's face it, AI is here to stay, and we aren’t talking about the huge lack of connection at work.

 

I get it, you've got the managers who can run a P&L like nobody's business, but what if you needed to ask them to help handle a coworker who’s having a panic attack or quarter life crisis, would they be able to navigate the situation confidently? Or would they suddenly set their Slack status to “BRB” while they scurry off asking ChatGPT or Googling "how to be more empathetic" on their way to the bathroom?

 

I’m going to assume the latter response.

 

Here's the thing that everyone knows but nobody is willing to say out loud: We're promoting people into leadership roles and then acting shocked when they can't lead humans. Baffling right? It’s like handing a teenager the keys to your car, without ever teaching them to drive, then wondering how on earth they managed to hit a fire hydrant and why there's a pile-up in the parking lot.

 

The Real Cost of Emotionally Illiterate Leadership

 

"People don't quit jobs—they quit their managers."

 

(Read that again)

 

Insert Eye rolls and “Yeah, we've all heard that one before” But do we know what that actually looks like in our daily life? Because it’s happening every day and nobody is talking about it:

  • Your best people are quietly updating their LinkedIn profiles
  • Team meetings feel like a performance at a theater
  • Everyone's burned out but pretending they're "crushing it"
  • Feedback sounds like warfare, not a conversation

 

In fact, 76% of employees say they're more engaged with highly empathetic leaders. The other 24%? They're probably too emotionally exhausted to answer the survey.

 

And frankly, ignoring soft skills isn't just bad for company morale—it's expensive as hell. Low retention, high burnout, and teams that are emotionally checked out while physically present. That adds up to more “Mental Health Days”, “Sick Days”, more budget dedicated to training, higher churn, and ultimately could lead to watching your top tier talent putting in their two week notice to go work for your competitors.

 

Here's Why "Soft Skills" Are Actually the Hardest Skills

 

We need to talk about what soft skills actually are (because half the corporate world is still confused):

 

Personality: empathy, resilience, not being a complete nightmare to work with

Behavioral habits: showing up mentally and physically, following through with tasks, active listening, communicating consistently

Teachable skills: conflict resolution, negotiation, critical thinking

Contextual competencies: reading the room, cross-cultural communication, stakeholder management without wanting to scream (or break something expensive)

 

These skills are messy, very situation-dependent, and require actual emotional intelligence. They require the ability to connect with others, to see the world through someone else’s perspective, and lots of empathy. Which is exactly why they're so dang hard to teach—and why most leadership programs completely avoid them.

 

So, companies can’t just write a check and send their executives and managers off to retreats every few years and hope they figure it out.

 

Soft skills aren't personality traits you're born with. They're learned behaviors.

 

Stop Hoping Your Managers Will "Just Get It"

 

Would you let someone run your personal finances without any training? No absolutely not. So then why are businesses letting managers run teams without any emotional intelligence?

 

The corporate world keeps promoting high performers into management roles, but then they cross their fingers hoping that their managers magically develop people skills.

 

Spoiler alert: they won't. (Please. Make it make sense?)

 

Leadership isn't a personality type—it's a teachable skill set that has to be learned. And in 2025, it's time we started treating it like one.

 

How to Actually Teach Soft Skills (Without Everyone Rolling Their Eyes)

 

Skip the Corporate Jargon, Use Real Life Examples and Scenarios

 

Nobody needs another training on “better workplace mentality” or an updated PowerPoint Presentation about "active listening." What we need is practice handling real situations before they escalate to something we can’t handle.

 

Instead of this: "Let's discuss the revised conflict resolution strategies."

 

Try this: Set up a role-play where one manager plays Person 1, who's been missing deadlines, and another manager plays the role of Person 2.

 

Give Person 2 this scenario: "Person 1 has just snapped at you in the team meeting. You can see that they are overwhelmed, but the project is behind and KPI’s are not on track. What do you say?"

 

Then, grab a snack, and sit back and watch them fumble through it the first time.

 

The second time, give them some tools: "Person 1, I noticed you seemed frustrated in the meeting. Can I ask what’s going on?" instead of "Your attitude was unprofessional."

 

Then have them practice the "your team member is crying in the conference room" scenario.

 

The goal is to make it real, make it safe, and make it useful. Because when it comes to empathy and soft skills, practice and repetition are key to mastery.

 

Storytelling > Corporate Jargon

 

Stop with the PDF’s, videos, and instead of sending your managers to another workshop about "synergistic team dynamics," try this:

 

Provide them with story-driven prompts that actually make people think: "Tell me about a time you felt completely misunderstood at work.”

 

“What did your manager do or not do?” Now flip the script—”How would you handle that as a leader?"

 

Then throw in some self-reflection exercises that don't feel like a homework assignment: After a tough team meeting, ask: "What emotion am I avoiding right now?”

 

“What would happen if I named it?"

 

“Who do I have that I reach out to for support?”

 

Guided journaling prompts (yes, really): Give managers 10 minutes of free time to journal like: "This week, I felt triggered when _____ because it reminded me of _____. Next time, I'll try _____."

 

Reflective debriefs after meetings: "How did that feel?" is just as important as "What went wrong?"

 

Try Reflecting: "On a scale of 1-10, how emotionally safe did everyone feel in that room?"

 

Give Them Tools That Actually Work

 

Generic leadership handbooks belong in a recycling bin. What managers need are concrete, practical tools they can use in the moment (in vivo) the moment. They aren’t going to grab a handbook, skim the table of contents, only to have to find a highlighted section on emotion regulation theory while hoping it’s somehow related to chaos unfolding in the lunch room next door.

 

What managers need is something like the Feelings Found Needs Wheel, because sometimes you just need to figure out what the hell is happening emotionally before you can fix what's happening operationally.

 

How to Scale This Stuff Without Losing Your Mind

 

You don't need to send everyone to a 3-day mindfulness retreat in the himalayan mountains, although that would be really awesome, you just need to find ways to embed emotional intelligence into the daily culture:

 

Start small by Adding a 5-minute "Feelings Forecast" to team stand ups like the following:

 

Manager: "Before we dive into sprint planning, let's do a quick feelings forecast. I'm at 6 today—feeling optimistic but slightly overwhelmed.

 

What about you, (Insert name of coworker)?"

 

Coworker: "I'm at a 4. Anxious about the client presentation tomorrow."

 

Manager: "Got it. What do you need from the team to get to a 6?"

 

Include emotional debriefs in project retro

 

Instead of running through the same old typical questions like: "What went well? What didn't?"

 

Try something like: "How did we feel during that launch week?”

 

“What emotions came up when one of the bugs was discovered?”

 

“How did we handle stress as a team?”

 

“What would we do differently next time—not just process-wise, but emotionally?"

 

Encourage naming needs during 1:1s

 

Manager: "You mentioned feeling frustrated with the marketing team. What specifically do you need from them?"

 

Employee: "I need clearer timelines and less last-minute changes."

 

Manager: "And what do you need from me to make that happen?"

 

These aren't touchy-feely exercises—they're real, practical, and can easily be turned into a repeatable routine. These micro rituals are set up in a way that normalizes emotions and feedback without making it awkward or too weird.

 

How to Know If It's Actually Working

 

Listen for the Shifts

 

All teams are unique and there’s no one size fits all solution. The key is noticing if there’s a change. Are people speaking up more in meetings? Is feedback starting to sound like a conversation instead of a monotonous performance review? Are your teams actually collaborating instead of just coexisting?

 

Ask the Right Questions

 

Skip the generic employee satisfaction surveys. Here are some actual questions that get real answers:

 

Instead of: "Rate your job satisfaction 1-10"

Try something like: "Do you feel safe offering critical feedback to leadership?"

 

Instead of: "How would you rate team communication?"

Try something like: "Can you disagree with your manager without it being career suicide?"

 

Instead of: "Are you satisfied with management?"

Try something like: "Do you feel heard, or just managed? What's the difference?"

 

Follow-up questions that matter:

 

  • "When was the last time you felt genuinely supported at work? What happened? And how can we replicate that in your role?”
  • "If you could change one thing about how feedback is given here, what would it be?"

 

Track Psychological Safety

 

Here's a fancy term for a super simple concept: Psychological Safety-  "A shared belief that the team is safe for interpersonal risk-taking."

 

In other words: Can people really be human at work without getting fired?

 

What Emotionally Intelligent Leadership Actually Looks Like

 

Meet Halo. Star performer, got promoted to management, and six months later her team had completely mentally checked out.

 

What she used to do: A team member would reach out to Halo.

Team member: "I'm struggling with this project."

Halo: "Just prioritize better. Here's a framework that works for me."

The turning point? Learning to say: "I don't know, but I'm here."

What she does now:

Team member: "I'm struggling with this project."

Halo: "That sounds overwhelming. Tell me more about what's not working."

Team member: "I keep getting pulled into other people's urgent requests."

Halo: "That's frustrating. What would need to change for you to have more control over your time?"

 

The difference? The first response is fixed. The second response is more open ended and allows for exploration.

 

Not having all the answers, and still creating space for honesty, vulnerability, and shared problem-solving.

 

Here’s another example: When a project failed, old Halo would say: "Let's analyze what went wrong and create a prevention plan."

 

New Halo says: "Before we dive into solutions, let's talk about how that felt. I'm feeling frustrated and a little embarrassed. What's coming up for you?"

 

Because here's the thing: Yes, technical competency gets you promoted. Emotional intelligence keeps your team from quitting and jumping ship for the competition.

 

Your Next Steps (That You'll Actually Do)

 

Stop overthinking this. Start small with these steps:

 

✅ Run a 15-minute soft skills audit with your leadership team

Ask: "What are we good at? What makes us want to hide under our desks?"

Then get more specific: "When someone comes to you upset, what's your first instinct? To fix it or to feel it with them? Neither is wrong, but knowing your default helps."

 

✅ Use the Needs Wheel during team reflections Next time tensions are high, pull it out: "Before we problem-solve, let's figure out what everyone actually needs right now. Is it clarity? Autonomy? Recognition?."

 

✅ Practice the "name it to tame it" technique When emotions are running a little high in meetings: "I'm noticing some tension in the room. I'm feeling frustrated, and I'm guessing others might be too. Can we take a few minutes to explore what's happening before we move forward?"

 

You don't need more tools or software. You don't need more consultants. You need more self-awareness.

 

TL;DR The Bottom Line

 

Your managers aren't broken. They're just really overwhelmed and under equipped for the human part of leadership.

 

We need to stop crossing our fingers and hoping they'll "just get it." We need to teach them the skills they were never taught.

 

Because if your team's emotionally checked out, your leadership probably is too.

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