top of page

The Good, The Bad, and The Ugly of Startup Founder Communication

Leadership is communication and effective communication is always a challenge, even in the most ideal environments. So what does that mean for communication for the time-starved, high-stakes, high-failure world of startups? It means everything – especially for founders.

When you think of early-sate startups, think college roommates. Close living quarters and a general lack of maturity lead college roommates to fight; poor communication (of course, binge drinking probably didn’t help) often ends college friendships. The shared desks, tight quarters, and crazy hours of startups make communication scarcely different for start-ups. If you have any chance of growing to become a successful company, you better have strong founder communication.

Start-ups, like any type of relationship, require different communication strategies over time. A first date requires an entirely different skillset than what’s needed to maintain a healthy and productive marriage. To be successful in your startup, you’re got to nail communication in every step in the journey. If you don’t get it right when the only employees at your business are the founders – you won’t get a second date…and you certainly won’t get to successfully manage a team.

Many founders, especially young founders and first-time founders, exclusively focus on their product & customers at the expense of giving thought to team communication. Poor founder communication leads to wasted time, decisions revisited over & over, and a dysfunctional culture that’s tough to overcome. Accelerators and incubators around the country are littered with failed start-ups thanks to poor communication.

In my years in the start-up world, I’ve seen a few recurring behaviors and patterns that predict successful communication versus startups that stall out after that first date. Here’s The Good, The Bad, and The Ugly.

The Good

Open Debate

There’s no room for “Yes Men” or “Yes Women” anywhere in a start-up, let alone inside the founder team. The ante for playing is the willingness to have a take and clearly communicate where you stand. I love seeing founders intensely debating important topics. Not only do these discussions allow the best ideas to bubble to the surface, but they also create a culture where people give a shit and future team members feel obligated to dissent when they have a different opinion. Hash it out and don’t hold back, except to be civil.

The Second Conversation

This is where good communicators differentiate themselves. Second conversations, a staple of great leaders, are initiated after meaningful or tough conversations. Good communicators take the time to learn from their interactions with fellow founders and re-visit how the effectiveness of the conversation, not the substance of the issues. I’ve found it really effective to ask a few simple questions after the dust had settled on a conversation, usually on a late night or early morning call with my co-founder:

  • How did you feel coming out of our conversation about equity/target market/progress in our sprint/anything important?

  • Do you think we used the right process to talk about that?

  • How could we have done a better job communicating?

Ongoing Feedback Sessions

You can’t hide from your strengths and weaknesses, so why try? The best founders are transparent with their personal goals, limitations, and ambitions. If it’s important that you not work certain days (like, say, Fall Saturdays) or don’t feel like your partners are focusing on the right things, speak up and share your perspective. Give frank feedback to help your founders and most importantly seek out feedback to really understand your co-founders perception. Don’t dwell on the past, but use history to be a better leader. Make it happen by scheduling a regular walk or coffee outside the office.

The Bad

Wasting Time on the Unimportant

Efficient founders focus their collective efforts on the core of the business, not on administrative needs or debating anything but the most critical decisions. Don’t fall into the same trap I once did and spend hours debating healthcare plans with your co-founder. Always keep an eye on the big picture and be quick to delegate decision-making. Clearly communicate the owner of day-to-day operational decisions and let them do their thing.

Not playing to your strengths

Do what’s right for the company, not yourself. Start-ups get in trouble fast when founders make decisions based on who they want to be, or the control they want to exert, rather than what’s best for the company. Be real and define responsibilities based on inherent strengths. If you’re not a details person, don’t handle invoicing. If you’re an introvert, don’t lead business development endeavors. If you’re a big picture thinker, be sure to keep time on your calendar to do exactly that.

The Ugly

Lingering Uncertainty

I’ve seen far too many founders afraid of bringing up unresolved issues with their co-founders. Most of these tough issues center on Founder A having concerns about the role or commitment of Founder B and how it impacts the company. Rip off the Band-Aid and have the discussion. Don’t worry about having a perfect conversation; they don’t actually exist in nature anyhow. Instead, worry about the dangers of letting important team issues fester inside the founder team. Uncertainty is terrible for the stock market, and it’s even worse for your start-up.

Undermining Trust

Trust is king and the moment trust is lost amongst co-founders, you’ve lost your company. This doesn’t mean that founders won’t (or shouldn’t) argue with one another, this means that in their heart of hearts, everyone respects the work of the other founders and everyone 100% believes the other sitting around the table are looking out for the best interest of the company.

The most common ways founders erode trust early on? The ole bait & switch. After founders agree who will make the call for a particular part of the business (Let’s say Founder A), someone else jumps in (Say, Founder B) after a decision has been made by the assigned decision-maker (Founder A). Here’s how this story ends: Founder A feels undermined and Founder B is unsettled by the effort or decision-making ability of Founder A. This is dangerous, particularly when the stakes aren’t high. Collaborate on key decisions and get comfortable with lots of small decisions being made by others. Teams need many decision-makers working in parallel, not everyone trying to make each and every decision.


Founding Grand Circus with my partner Damien, I have a trusted partner and respected friend. We didn’t communicate perfectly – nobody does – but I’m proud of our active ongoing dialogue and our commitment to continuously improving our communications.

From being surrounded by countless startups including my own, I leave you with two final thoughts on founder communication:

  1. Have tough conversations. Have them frequently. This is a sign of team strength, not weakness.

  2. Understand the difference between a wrong decision by a co-founder and a decision that you don’t think is best. Fight against wrong decisions and fight like hell to resist the urge to debate decisions that you view as ‘not best’.


bottom of page