258: On Fostering Managerial Initiative [Ask Jason]

Dear Jason,

After grinding on my business for several years, I've finally hit a point where we're generating solid revenue. We've built a capable team, and I'm now installing "heads of" to run various divisions.

Despite this progress, I still find myself driving initiatives and constantly following up with my managers. I don't want to micromanage, but I also don't have full confidence that they'll deliver without heavy oversight.

What am I missing here? How can I effectively transition to the next phase of growth?

Sincerely,
Captain Can't-Let-Go

Dear Captain,

There's an interesting transition from being a high agency achiever, which is what most founders have to be in the early days, to becoming a player-coach, to becoming a full-on delegator.

I see many of my clients struggle with this transition because it requires a different set of skills and forces you to go against some of your instincts.

To get to where you are today, you've had to identify problems and act immediately to address them. If there are holes, you plug them. You don't wait around for others to figure it out and hope it gets done. You make sure it happens.

As an individual and as a direct manager, this approach can work.

You follow up on tasks, check in with people directly, and if necessary, do the work to get the project done. But once you start managing managers, things change. You have to get the work done through your managers rather than through direct action.

Not everybody can handle this transition.

Michael Jordan was one of the greatest basketball players to ever live, but he made a notoriously bad coach and team owner. Because he couldn't understand why other players couldn't simply perform at his level of excellence and intensity.

Meanwhile, Steve Kerr, who played on the Bulls with Jordan, has successfully transitioned into a highly effective coach of the Golden State Warriors. Kerr understands that coaching requires a completely different skillset than playing – it's about developing others rather than showcasing your own abilities.

In a situation where things aren't happening, there are two possible explanations:

1. You don't have the right people, or
2. You aren't leading them in the right way.

Today, we'll focus on the latter.

In order to drive effective action through your managers, you need to make sure they understand the priorities for the organization.

What are the high-level goals that the company is aiming for? Whether it's product development, revenue growth, or building a competitive advantage, your managers should be crystal clear about the company's objectives and how their department's work contributes to these goals. They should be able to draw a direct line from their department's key initiatives to the top-line objectives and understand it's their job to help get the organization there.

One of the most popular reprinted Harvard Business Review articles of all time is the 1974 piece "Who's Got the Monkey?". The idea is that managers must not take the onus of responsibility for a problem (the "monkey") away from their subordinates. The mantra it advises managers is thus:

"At no time while I am helping you with this or any other problem will your problem become my problem. The instant your problem becomes mine, you no longer have a problem. I cannot help a person who hasn't got a problem.

When this meeting is over, the problem will leave this office exactly the way it came in -on your back. You may ask my help at any appointed time, and we will make a joint determination of what the next move will be and which of us will make it.

In those rare instances where the next move turns out to be mine, you and I will determine it together. I will not make any move alone."

The article also offers what I believe is the first formulation of the five levels of delegation:

1. Wait until told (lowest)
2. Ask what to do
3. Recommend a solution, act after approval
4. Act first, and provide an update right away
5. Act on own, provide routine updates later (highest)

Mid-level managers should mostly act at Level 3 and 4, while senior leaders are acting mostly at Level 4 and 5. But the only people at Level 1 should be interns and trainees, and only at Level 2 rarely.

One of the most important monkey's a manager should have is ownership of The Plan and evaluating the progress against The Plan. The Plan might be a strategy doc, a Gantt chart, a product roadmap, but it most entail how the manager aims to contribute to the company's top level objectives.

That manager should also be able to provide their own evaluation of their progress against The Plan, to be discussed and reviewed by you. If you understand and agree with The Plan, and they are on track against it, all is well.

If The Plan is not clear, not effective, or not on track, then it is a monkey on your manager's back to fix it, with your careful, non-ownership help.

And if after repeated attempts, they fail to fix the issue, then they are probably not the right fit for the organization and you need to make a personnel change.

So to sum up:

1. Make sure you and your managers are clear about the organization's top priorities
2. Make sure your manager understands they own the monkey and what level of initiative they are expected to take
3. Make sure your manager owns The Plan, a clear and credible path towards success
4. Regularly check in on progress against The Plan, and address issues along the way.

Remember that your job as founder / CEO isn't to grab the monkey back when things get tough. Your job is to create the conditions for your managers to succeed with their monkeys. This means providing clear context, removing obstacles, and coaching them through challenges without taking over.

When you find yourself tempted to jump in and "just do it yourself," pause and ask: "Am I helping my manager grow, or am I reinforcing their dependence on me?" The most successful leaders aren't those who carry all the monkeys themselves, but those who build a team of confident, capable monkey-handlers who deliver results without constant supervision.