The Letting Go Problem

For Chris Tatge, one of the first meaningful handovers in his framing business was the bookkeeping. He found an accountant he trusted and moved the work off his own plate. In his account, the relief made it easier to consider delegating other responsibilities.

The first handover did more than free up time. It gave him an example of work being done well without his direct involvement. That is often what a founder needs before the next conversation about delegation becomes credible.

A handover needs a decision owner

Assigning a task is relatively easy. Transferring responsibility means allowing someone else to decide how to carry it out, within limits both people understand.

Without that agreement, the founder stays involved in every exception. The employee may complete the work but still wait for permission to make it useful. A company can have a management team on paper and a single decision-maker in practice.

Michael McLean describes founders who own their companies but cannot step away from them. The dependence can be hard to see while the founder is available. Look instead at what waits when they are absent: pricing exceptions, hiring choices, customer commitments, or routine spending.

Each item needs a decision. Keep it with the founder, transfer it with clear limits, or stop doing it. Leaving it informally shared often means it returns to the same person.

Advice can create more work for the founder

Ashish Gupta noticed this in his own experience of receiving advice. Conversations added tasks faster than he could complete them.

A capable adviser can identify a useful change. The company still needs someone with the time and authority to make it happen. If every recommendation becomes another founder task, even good advice can deepen the bottleneck.

Before adding work to a plan, name who will own it and what that person can stop or postpone. If the answer is always the founder, the company has a capacity problem to resolve before it has a longer plan to write.

Agree what happens when judgment differs

The difficult part of delegation often arrives after the first decision the founder would have made differently. Reversing it without discussion can teach the new owner to seek approval next time. Ignoring a serious mistake is no better.

Set the boundaries before that moment. Be explicit about the outcome, spending authority, customer commitments, and situations that need escalation. Agree when to review the work. This gives both people a way to distinguish a reasonable difference in judgment from a decision outside the remit.

Recruiter Jamie Crosbie's argument for hiring before the need becomes urgent applies here. A handover takes time to learn. Waiting until the founder is overwhelmed leaves less room for explanation, questions, and correction.

Start with one responsibility that repeatedly returns to your desk. Find a capable owner, agree the limits, and set a review date. Then let that person make the ordinary decisions the responsibility requires. Tatge's accounting handover was valuable because it became a working example he could repeat.