Practical insights for leaders

Why is delegation harder than it sounds?

Effective delegation comes up again and again as a stumbling block for leaders. When done right, delegation makes your life a whole lot easier. And, frankly, it is a required skill for leaders. 

For leaders to have mixed feelings about delegation is very common. By far the most common concern from leaders is that they know they should delegate more often, but for any number of reasons, they perceive it as an unproductive – or even risky – proposition. Common counters I hear include, “It’s quicker to do it myself”, “I don’t want to over-burden the team”, “this project is critical”, “I don’t trust others to execute how I would”, and “I have no one to delegate to”. 

There may be times when your reservations about delegating are accurate. But, if you heed them every time, you are virtually guaranteeing that you are going to perpetuate the status quo with respect to how work gets done. So, commit to delegating. See below for my favourite article on delegation and a ‘delegating with input’ tool (ask me for a step-by-step delegation script).


Read: Management Time: Who’s Got the Monkey?’ | HBR Article | 12 mins

Do you ever feel that you’ve spent the entire day sorting out other people’s problems?  If you find that as a manager, you are typically running out of time while your subordinates are running out of work, then HBR’s timeless classic, ‘Who’s Got the Monkey,’ is a must-read.

To use the article’s monkey-on-the-back metaphor, managers are trapped in an endless cycle of dealing with other people’s monkeys, yet they’re reluctant to help those people take their own initiative. As a result, managers are often too busy to spend the time they need on the real gorillas in their organisation.

Oncken and Wass’s article, first published in 1974, remains a powerful wake-up call for leaders on the importance of clear communication, delegation, and accountability.


Tool: Delegating with Input

Sit down with your direct reports to review their key areas of responsibility. Ask them*: 

– What does great support from me look like? 

– Are there areas where you believe I get too involved and can let go more?

– Are there areas where I need to get more involved and give you more help?

– Do you ever see me working on tasks that someone at my level doesn’t need to do?

If you don’t ask these questions, you might be delegating without input – and literally without a compass. You will be flying blind. *H/T to Marshall Goldsmith for these great questions.


Call me a masochist, but one of my favourite parts of running a business is the connection between my decisions and actions and the business’s success. The results don’t lie! I left investment banking partly for a better quality of life, but my unrelenting standards and insistence on doing everything myself left me feeling burned out in the early days. Lesson learned. The cartoon below looks eerily familiar!