Why working with others feels so hard

team work, how to work better with othersWhen you start a business, you imagine:

  • Motivated people

  • Clear tasks

  • Smooth communication

  • Everyone rowing in the same direction

Then reality shows up:

  • A co-founder goes quiet after a tough meeting.

  • A teammate feels ignored but doesn’t say anything.

  • Someone dominates the conversation and others shut down.

  • You walk away from a call thinking, “Something felt off… but I can’t quite say why.”

The hardest part about working with others is that most of the tension isn’t visible.

On the surface, people smile, nod, agree. Underneath, there might be:

  • Fear – “What if I’m not good enough?”

  • Pride – “I need to prove I’m right.”

  • Insecurity – “They don’t value my contribution.”

  • Exhaustion – “I’m overwhelmed, but I don’t want to look weak.”

As a founder, you’re not just managing tasks. You’re navigating all of that emotional undercurrent, in others and in yourself.

That’s why meetings can feel heavier than the agenda. And why a small misunderstanding can lead to:

  • Quiet resentment

  • Passive resistance

  • Slower execution

  • People mentally checking out

If you’re planning for starting a business, this is the part to anticipate early:
You’re not just building a product. You’re building a space where humans work together under uncertainty.

And uncertainty amplifies emotions.

So let’s look at what you can actually do about it.

1. Listen first: the underrated superpower of early-stage founders

Most first-time founders think leadership is about:

  • Having the answers

  • Making the final call

  • Being “right”

In reality, especially when you start a business, leadership is much more about:

  • Asking good questions

  • Actually listening to the answers

  • Letting people feel seen and safe

When people feel safe, they tell you what’s really going on. And when you know what’s really going on, you can actually fix things before they explode.

What “listening first” looks like in practice

Here are simple behaviors you can turn into habits:

  • Begin meetings with a quick emotional check-in

    • “Before we dive in, how’s everyone doing today, honestly?”

    • You’ll be surprised how often this explains the energy in the room.

  • Repeat back what you heard

    • “So if I understand you correctly, you’re worried that launching in March is too rushed for testing. Is that right?”

    • This shows respect and clears up confusion early.

  • Ask the quietest voice in the room

    • “We’ve heard a few takes here. Alex, what’s your view?”

    • Quiet doesn’t mean disengaged. Often, your best insights are sitting with the person who speaks last.

  • Separate the idea from the person

    • Instead of: “You’re wrong.”

    • Try: “I see your point. Let’s test that assumption against the data.”

Why this matters when you’re starting a business

In the early days, you move fast and break things. You will be wrong sometimes. Everyone will. The question is:

  • Can your team disagree without breaking trust?

  • Can you change direction without making people feel stupid or small?

Listening first makes it possible to shift strategy without damaging relationships. And that’s gold.

2. Create safety: where growth and honest feedback can actually happen

You can’t build a successful startup if people are constantly:

  • Afraid to speak up

  • Afraid to disagree with you

  • Afraid to admit mistakes

If you’re planning for starting a business, it’s tempting to focus on tools and frameworks. But you also need to build something more basic:

A culture where people feel safe enough to tell you the truth.

Signals of an unsafe environment

Notice these red flags:

  • People agree with you too quickly.

  • After the meeting, someone messages you privately with their “real” opinion.

  • Mistakes get hidden, or only discovered when it’s too late.

  • Jokes feel sharp, personal, or passive-aggressive.

If you see this, don’t panic but don’t ignore it. You can reset the tone.

How to build psychological safety (without sounding like a corporate manual)

You don’t need posters and slogans. You need consistent behavior. For example:

  1. Normalize “not knowing”

    • Say things like:

      • “I’m not sure yet, what do you think?”

      • “I was wrong about that assumption, let’s adjust.”

    • When you admit you’re human, others feel allowed to be human too.

  2. Respond well to bad news

    • If someone tells you: “We lost a customer because of a bug,” and you snap or shame them, guess what? Next time, they won’t tell you.

    • Try: “Thanks for flagging this. Let’s fix it together and see what we can learn.”

  3. Praise the behavior, not just the result

    • Don’t only celebrate success. Also celebrate:

      • Asking a hard question

      • Calling out a risk early

      • Owning a mistake

    • This shapes what people think is “allowed” here.

  4. Use humor to make things human

    • You don’t need to be a stand-up comedian.

    • Gentle, self-deprecating humor can de-escalate tension and remind everyone: we’re not robots; we’re learning as we go.

When safety is high, people will:

  • Share ideas earlier

  • Surface risks sooner

  • Help each other instead of competing for credit

And that is exactly what you want when you start a business with limited time, money, and energy.

teamwork, working together, listening to team mates

3. When opinions collide: data over pride

Disagreements aren’t a sign something is broken. They’re a sign people care.

The problem isn’t disagreement itself. The problem is how you handle it.

As a first-time founder, you’ll see this scenario a lot:

  • You believe Feature A is the key to growth.

  • Your co-founder believes Feature B is more urgent.

  • Your marketer wants to delay both while fixing the landing page.

Suddenly, it’s not about the features anymore. It’s about:

  • Who gets to be “right”

  • Who feels heard

  • Who feels respected

If you let ego drive the conversation, you’ll end up with:

  • Political decisions (“We’ll just do your idea this time so you stop complaining”)

  • Long debates that go nowhere

  • Decisions based on who speaks the loudest

The “data, not drama” rule

One of the simplest ways to handle conflict is to make a shared agreement:

“When we disagree, we go to the data, not to who has the strongest opinion.”

In practice, this can look like:

  • Run small tests

    • “Instead of arguing for a week, let’s A/B test both landing page headlines for 7 days.”

    • “Let’s prototype the leaner version of Feature A and let real users tell us if they care.”

  • Use clear criteria for decisions
    Before you decide, define:

    • What problem are we solving?

    • How will we measure success?

    • What’s the time-box (e.g., 2 weeks, 1 month)?

  • Write things down

    • Capture decisions, assumptions, and experiments in one place.

    • When tension rises again later, you can point back to: “This is what we agreed to test.”

A simple framework for tough product or strategy decisions

Next time your team is stuck, try this structure:

  1. Clarify the question

    • “What exactly are we deciding right now?”

  2. List options (no judgment yet)

    • Option A, Option B, Option C

  3. List pros & cons for each

    • Impact

    • Effort / time

    • Risk

  4. Choose 1–2 options to test

    • Short experiment, clear metric

  5. Schedule a review date

    • “We’ll regroup on this in 2 weeks with results.”

This doesn’t just solve the immediate disagreement. It teaches your team a way of thinking.

And when you’re planning for starting a business, having a simple decision-making habit like this can save you from endless circular debates that drain your energy.

4. Build your “human operating system” from day one

Most founders obsess over systems for:

  • Product development

  • Marketing funnels

  • Sales pipelines

But they don’t build systems for something even more important:

How we treat each other. How we communicate. How we give feedback. How we work when we’re tired, stressed, or scared.

Think of this as your human operating system.

You don’t need a 50-page culture deck. Instead, you need a few clear, lived principles and tiny rituals that keep you grounded.

Example: 5 simple “team rules” for early-stage startups

You can adapt these, but something like this works well:

  1. We are honest, even when it’s uncomfortable.

    • No fake agreement in meetings. If something doesn’t sit right, we say it respectfully.

  2. We criticize ideas, not people.

    • “This approach has some risks,” not “You always overcomplicate things.”

  3. We use data whenever possible.

    • Opinions are welcome; experiments are better.

  4. We assume good intent.

    • If someone snaps, we check in: “Are you okay?” instead of silently resenting them.

  5. We balance ambition with humanity.

    • We push hard, but not by burning each other out or tearing each other down.

You can share these in your first team meeting, then re-visit them monthly and ask:

  • Are we actually living these?

  • Which one are we slipping on lately?

  • Do we need to adjust or add anything?

Tiny rituals that make a huge difference

Rituals are small, repeated actions that embed your values into daily work. For example:

  • Weekly 30-minute “real talk” session

    • One question: “What’s one thing that’s bothering you about how we work together right now?”

    • No blame, just improvement.

  • Monthly 1:1s focused only on the person, not the project

    • Ask:

      • “How are you doing?”

      • “Where do you feel underused?”

      • “What’s one thing I could do to support you better as a founder?”

  • “No surprise feedback” rule

    • If something bothers you, you bring it up privately within 48 hours.

    • You don’t wait 3 months and then explode.

  • Celebrate small wins

    • End the week with: “What went well?”

    • This keeps people from feeling like it’s only about what’s broken.

These are simple, but they compound over time. Just like your product roadmap, your human operating system gets better with iteration.

Bringing it all together: humans first, metrics second

When you start a business, you’ll hear a lot about:

  • Hustle

  • Product-market fit

  • Jobs to be done

  • Revenue

All of that matters. But here’s the quiet reality:

  • A great product with a broken team won’t go far.

  • A strong, honest, emotionally healthy team can fix a broken product.

The hardest part about working with others isn’t something you “solve” once and forget. It’s something you keep learning, adjusting, and practicing.

Key ideas to remember

  • It’s not the strategy; it’s the humans.
    Emotions, egos, fears, and the need for validation are always in the room.

  • Listen first.
    Make people feel heard, not managed. The quality of your listening determines the quality of your decisions.

  • Build safety.
    Make it okay to say, “I don’t know,” “I was wrong,” or “Something feels off.”

  • Use data over pride.
    When opinions collide, let experiments and evidence decide, not ego.

  • Create your human operating system.
    A few clear principles and simple rituals can transform how your team works together.

Your next step as a first-time founder

If you’re planning for starting a business right now, here’s a simple exercise:

  1. Write down three ways you want people to feel when they work with you.
    For example: respected, heard, supported.

  2. Write down one habit you will start this week to support each feeling.

    • Respected → “I’ll stop interrupting and let people finish their thoughts.”

    • Heard → “I’ll summarize what I heard before sharing my view.”

    • Supported → “I’ll ask each teammate once a week: ‘What’s blocking you, and how can I help?’”

  3. Share this openly with your team or future co-founders.

    • “This is how I want us to work together. Hold me accountable to this.”

This is how you start leading humans, not just metrics.

And as you keep planning for starting a business — your roadmap, your MVP, your go-to-market — remember:

The real “unfair advantage” isn’t just your idea. It’s how well you handle emotions, conflict, and collaboration when no one’s watching.

If you build that skill set early, everything else in your startup becomes easier to fix.

Because in the end, your startup is people.
Take care of that system, and it will take care of your growth.

Author: Guido Picus

Linkedin My book: Maverick Soul

Guido Picus is CEO of GrowthApp.co, helping first-time founders turn ideas into real businesses. He’s a serial entrepreneur with 20+ years of startup and marketing experience, including a successful exit to Deloitte Digital.

1/5/2026
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