Letting Go

Founders and early hires in startups operate as generalists working on specific problems. There is too much to do and too little time to specialise. As the company gains momentum, new initiatives increasingly require exponential amounts of effort. The generalist model of everyone working on everything fails to scale.

This is the moment when you as a leader stop being the best at your job and the requirements begin to outstrip what you can achieve. The level of control you have so far enjoyed starts causing damage.

There are other common symptoms at this stage: you do not prioritise work that a specialist would, you are accused of micromanagement when you thought you were defining priorities, and decisions take longer because you are required for everything. The details and micro-optimisations are now increasingly more important with scale and you are slowing down just when you need to move faster.

The default solution, if you have the means, is to hire more people. But hiring people, painting a vision, and assigning tasks under the guise of delegation is not enough. As a leader, your big-picture thinking is infectious and your team will view everything through your lens. The big picture will get so big that few people will be able to remember the details that matter and prioritise work incorrectly. This is bad: wrong priorities will lead to randomised roadmaps and demotivated teams.

People work best by knowing the boundaries for failure and success. Your job, as a leader, is to translate your big-picture thinking into tools that every employee can use to define these boundaries. Good delegation is not about assigning tasks but providing the tools that employees can use to invent new solutions, optimise existing ones, prioritise work, and ultimately make autonomous decisions.

You then have to calibrate these tools to know when to nudge, intervene, or take control. Intervene when things begin trending towards failure, but otherwise nudge people towards success. Taking control of work should happen only in the most extreme of circumstances.

Many founders and first-time leaders think like generalists and expect everyone to work the same way. Interviews are calibrated for specialists but new hires are expected to function as generalists. This makes everyone unhappy. Instead, as a leader, embrace your generalist thinking by constantly pivoting to focus on the broader challenges and work with the specialists on the details.

Your job is to define the direction, provide the tools, and make room for success. Good leadership and delegation is about letting go.