TRC 045: The why and how of being disagreeable

Read time: 5 mins

It’s not difficult to find a ton of opinions about how you should be running your company.

And if you speak to ten different investors about what how you should be approaching things, you are likely to end up with at least 7 or 8 different approaches.

You can feel dragged in many different directions from one day to the next.

That’s why many of the best founders are disagreeable.

It's not about being combative or dismissive; it's the courage to challenge how things are done, question the assumptions of others — even when you feel under pressure.

The Importance of Being Disagreeable

Avoiding the Pitfall of People-Pleasing

As founders, there's a natural inclination to accommodate opinions, avoid conflicts, and strive to keep everyone happy.

With one eye on keeping existing investor support for your next raise or making sure key team members are happy, saying yes to keep the harmony can seem vital from one day to the next.

While collaboration is important, excessive people-pleasing can dilute your vision and lead to decisions that steer your startup onto a path to a destination you didn’t intend.

The best companies are rarely built by those who always say "yes" purely to maintain harmony.

Challenging the Status Quo for Innovation

Innovation thrives on challenging conventional wisdom.

Being disagreeable means you're willing to question the "way things have always been done" and explore new territory.

This mindset is crucial for creating products or services that stand out.

This means you won’t be able to please everyone.

Cultivating a Healthy Approach

Listen Actively, Decide Selectively

Welcome diverse opinions and feedback, but filter them through the lens of your core mission and values.

Not every suggestion will be right for your startup, and that's okay.

Saying no when needed is a superpower.

The bigger the company gets, the more opinions you will have to deal with and the stronger (and more senior) the dissenting voices will be.

Communicate Your Vision Clearly

Ensure that your team and stakeholders understand your vision and the reasons behind your decisions.

Clear communication is vital for reducing misunderstandings when you choose a different path.

This is especially important when bringing new people onboard in any capacity (staff, investors, partners etc).

Onboarding is a very easy step to overlook when things are hectic, but it is an essential part of ensuring people are clear about what you are trying to achieve.

Build a Culture That Embraces Constructive Disagreement

Encourage your team to voice their ideas and challenge assumptions in a respectful manner.

This feeds innovation and ensures that decisions are thoroughly vetted.

It’s not about encouraging blame when things go wrong - nothing creative happens in that sort of environment - more that things are well prodded before they are started or pushed out of the door.

This is where ‘disagreeability’ can be a fine line, as the opinion you want to encourage challenge of the most, is your own.

It’s the fastest way to embed this culture into your business.

Stay Open but Guard Your Mission

Being disagreeable doesn't mean being inflexible.

Stay open to ideas that enhance your vision but be prepared to push back against those that don't.

I understand that it’s a fine line - not listening and coming across as an a**hole is definitely not a route to success.

But having the courage of your convictions, being open to opinions, but still having the courage to say no to things, or to say yes, in the face of opposition, is a key attribute to building a business that aligns with who you are and where you want to go.

I have seen too many key moments where founders have given in to investors or their senior team when they really knew it was the wrong decision, and ended up on the wrong path.

It’s good to listen to others and seek diversity of opinion.

But being a pushover won’t get you very far.

Stay strong.

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