CEO diary entry: control, accountability, whiplash & anxiety

What I'm learning as I build koodos labs

This piece started as a personal reflection, a kind of open diary entry. It's a vulnerable exploration, a little disjointed and I’m sharing it is an experiment. I've learned and am learning a lot about what a CEO's role is, and how it shifts with the growth of the company. I don’t claim to have mastered it — I am constantly learning and invite other thoughts or viewpoints. I hope offering a glimpse into my journey and my development as we build koodos labs is helpful, or at the very least, interesting.

On Control, Accountability, and Authority

In an effort to mirror what it’s like building a product and company, I ran an activity where my team had to piece together a puzzle without knowing the intended final image. When building a company, we have to be open to the fact that we don’t know what the final outcome needs to be as the puzzle pieces come together. And yes, even the founder doesn’t really know what the final image is. This led to a dialogue around whether stepping in or standing back was the most effective mode for the CEO to be in, especially considering the unique insights team members brought to specific segments of the puzzle.

Brian Chesky suggests that detail-oriented involvement from the CEO is crucial for maintaining alignment and momentum. He posits that the more proximate the main decision-maker is to the project the better. At the early stages, the founder is domain expert in many aspects of the company, but as the organization expands, the domain expert should ideally be the decision-maker, and often this isn’t the founder. Finding the balance between being in the details and empowering autonomy becomes a sophisticated dance of leadership.

Logically-speaking, I (as the CEO) am ultimately held accountable. And as a leader, I am in a unique position where I could have a lot of control, and could also shift accountability internally. So someone who's directly responsible for a project could technically have no authority (just do what Jad says) and full accountability (if the project goes south, they're ultimately responsible). And so where there’s accountability, there must be agency. And agency requires trust and letting go of control.

A rule of thumb my friend Matt Braley shared is to train the leader do the job to our standards, figure out how to measure the standard, then step away when we see the standard is met 80%+. Naturally, I’ve found that I let go when I trust the person, and I won’t when I don’t. If I don’t trust handing over the reigns, I should really ask myself “can we up-skill the person in a reasonable time so that we’re comfortable?” And if not, then the difficult question should be “why is is this person on the team?”

Despite my ultimate accountability as CEO, or someone's direct responsibility for overseeing progress towards a goal or project, it is essential to establish expectations and foster an environment where everyone takes ownership. That means that no one person is to blame, and that every member on the team is taking 100% responsibility. Everyone accepts their part in both successes and setbacks, openly discusses contributions to challenges, and actively works together to find solutions, fostering a culture of accountability and shared growth. Creating a culture where collective ownership is embraced means that success and failure are shared, fostering an environment of mutual accountability and collaborative growth.

On Whiplash

Navigating a startup is inherently turbulent, with constant learning and shifting priorities. Deciding what takes precedence and for how long is incredibly challenging but critical to progress. This journey demands a blend of urgency and the acceptance of imperfect processes, focusing on agility and on-the-fly problem-solving rather than flawless execution from the outset.

The CEO's actions can rock the boat even more as it navigates the turbulent waters. Underpinning it all is the view that clarity is kindness, and that getting to clarity is the ultimate goal. A few things worth aligning around could include:

• How much time we're "budgeting" for a bet, so that we're committing to a focus for some time, and also so that we're thinking about the scale of the project based on a specific time horizon.

• What part of the discovery process are we currently in? Are we diverging? Exploring different approaches, sketching 100 solutions, running lots of quick tests in different directions, etc. or are we converging: narrowing our focus, testing one thing out and maintaining constraints? 

• The communication flows day-to-day, ensuring that we're collaborating (and not working in silos) as much as possible, and also making room to check in that we're on track for a high impact project and naturally pre-morteming so things just float when there are blockers. Importantly, we should aim to do this in a way that doesn't apply unnecessary pressure or constrains creativity and play.

On Conscious Leadership and ‘Amping It Up’

I find myself toggling between two versions of myself as a leader.

The first: the empathetic, people-first servant leader. A la Concsious Leadership Group.

The second: the driven, results-focused executive that runs towards discomfort and doesn’t accept coasting. A la Frank Slootman’s Amp It Up.

This internal conflict generates both personal anxiety and confusion among my team regarding which version of me they’re dealing with. My goal is to forge an integrated leadership style that harmonizes these aspects, leveraging their strengths to guide my actions and decisions.

On Learning and Anxiety

I tell myself that it’s very natural to be anxious when we're trying to do something very hard, especially when the process requires making a lot of mistakes on the way. Rome wasn’t built in a day, and neither is the process of inverting the internet’s personal data model. Unlocking a retentive consumer product lots of people love is something very very few products can get to — and so I must remind myself that we’ve already achieved more than most startups can dream of.

I had heard many times that startup success is PACE OF LEARNING. But it took me a while to internalize that. A good way to maintain a strong pace of learning is to be in discovery mode – and this applies even at established companies (see: Kodak, or every big tech company that is trying to be bold and take risks again).

One way to reduce anxiety is to shift to a discovery mindset that celebrates learning, not just results. And to trust the process and maintain that learning will lead to results. There’s a lot of inertia against shifting toward a discovery mindset:

• Conditioning: We've been rewarded our entire lives for being right, knowing all the answers, and avoiding mistakes. But perfectionism slows us down when we need to learn by trial and error. We'll suffer endlessly unless we get comfortable with being wrong, not knowing the answers, and making mistakes.

• Incentives: Typically folks get recognized for results over learnings. That’s how we’re typically rewarded through school. This might work well in established businesses where the levers are well understood. But at a startup, we first have to learn what the levers are before we can set the right targets and strive for results. And learning leads to out-sized results.

• The illusion of knowledge: We can't learn things when we believe we already know, so this illusion of knowledge hinders our effort to discover. Recall the bull: beauty is in the simplest outcome (and often we’re stuck amidst the higher complexity phases, and so we actually don’t really know until we get to the simplest form of the bull or can explain a complex concept like a 6 year-old). We often view new information, especially contradictory information, as a threat thanks to our various cognitive biases (including our friends confirmation bias, hindsight bias, consistency bias and sunk cost fallacy).

This requires balancing being a confident visionary with being a curious, skeptical scientist. It's less about feeling confident we have the right answer, and more feeling confident that we can figure it out. When we work from a place of insecurity, we see information as a threat. But new information is the currency of discovery. Great scientists build the confidence to push aside their self-doubt and run toward surprises. To seek discomfort. A discovery mindset means openness, experimentation, focus on users and data, collaboration, bold thinking, and risk-taking.

Hit reply and let me know if this was interesting or useful, or not. This is an experiment :)