Why Great Startup CEOs Need to Hold Themselves Accountable

Written by Dave Bailey

CEO turning off alarm clock

Increasing your discipline is hard. Use these tips and systems to help you tackle the hardest issues first without burning out.

Making yourself more accountable can speed up your decision making and help you build a stronger business.

Autonomy is liberating. As CEO, it’s up to me to decide what I should focus on today. But this power has a dark side. We all have a bias to focus on things that are exciting and fun to work on and put off the least enjoyable tasks until later.

I’m certainly guilty of this. In my last venture, I waited too long to fire the employees that didn’t fit, and to sack the offshore development agency that wasn’t delivering. And famously, I failed to market my product before it was too late.

These were important problems with non-trivial solutions, and they impacted the entire company. The stakes were high, with customer accounts, ship-dates and morale on the line. Yet no-one was screaming, “Fix this now!” as they were for a hundred other demands in my inbox.

I learned that when something is important but not urgent, it’s easy to put it off until later. And sometimes, later is just too late.

Who’s really holding us accountable?

As CEO, I answered to the board of directors and shareholders. I reported monthly on the strategic performance of the business, but there was no time to get stuck into weekly operations. Besides, no one on my board had actually run a tech startup on a day-to-day basis anyway.

I sought advice from my network of mentors and advisors, but very few of them checked to see if I’d followed through. And was it even their place to do that?

I realised that the only person holding me accountable for my weekly performance was me. No-one was truly incentivised to push me on important operational issues, to stress-test my plans of action, or to call me out when I missed a personal deadline. And occasionally, just occasionally, self-accountability just isn’t enough.

Swept under the startup rug

I’ve worked with many founders that, like me, avoided going deep on important issues until they reached crisis point. They knew these issues existed . . . but they always came up with reasons for waiting to address them. Issues like:

  • Having less than six months of runway
  • Building on top of an unscalable architecture
  • Keeping the wrong people on the team
  • Ignoring signs that the market isn’t ready
  • Pursuing invalid revenue assumptions
  • Moving against technology trends
  • Extremely low user retention
  • Co-founder conflict
  • Unsustainable working hours

Issues like these are often too scary to bring up with the board, and are typically too complex to cover in a one-hour mentor session with someone that barely knows the context. Sometimes, they’re even too painful to admit to ourselves. We’ve all met a founder in denial, haven’t we?

Founders that have lost their companies and careers as a result of not addressing these issues all share the same regret: “I wish I’d addressed the real problem sooner.”

Building a system of accountability

The goal is to reduce the time between recognising important issues and addressing them. I call this limbo time. Reducing limbo time has a direct impact on your speed of execution and your time-to-revenue. 

The strongest-performing founders don’t rely solely on their notebook — and their personal willpower — to keep themselves accountable. They set up systems of accountability that guarantee clarification of important issues early, that enable them to plan effectively, and that help them to act quickly.

  1. Clarification. It’s helpful to talk through important issues with someone that’s able to ask good questions, which can help you assess the issue from different angles and reveal the blind spots we all have. Having someone play back your words is a great way to recognise faulty internal logic.
  2. Proactive planning. When solutions are too big to implement in a day, they need to be broken down into manageable chunks. To stay proactive, look for one or two actions you can implement straight away, and prioritise them over urgent, but relatively unimportant, tasks.
  3. Follow-up. Your to-do list isn’t always strong enough to hold you to your word, especially when there are a hundred other urgent items on it. Share your deadline with a co-founder or mentor and ask them to hold you accountable to it.

Find a CEO coach

Being a founder CEO is an incredibly hard job, even with the support of co-founders, mentors and advisors. Just as top athletes need a coach to keep them aware of the bigger picture, so too do top CEOs.

A good coach asks the right questions and plays your answers back to you, to help you recognise and clarify the important issues in your business. They pass on practical tools and personal experiences to help you grow as a leader. They help you stay proactive and they follow-up on difficult action items, to ensure you follow-through on the hardest parts of the job.

What are the important issues that you should be dealing with, but aren’t? Be honest — what are you waiting for?

Continue reading about CEO responsibilities: 

Originally published Mar 15, 2019, last updated Aug 20, 2021

coaching founders psychology

About Dave Bailey

Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week. 

I will never sell your information, for any reason.

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