3 person founder team.

Good delegation is making sure that each founder is playing to their strengths and asking for help on things that others are better at.

Functional boundaries are very flexible, and delegating is based mostly on optimal speed and quality of delivery.

Delegation to freelancers can already be in full swing at this stage, and is mostly about very clearly defined specific processes that have not yet been automated but still need to be done, and shouldn’t be done by a founder who has to focus on continued growth.

Sticking points preventing effective delegation:

  1. Admitting to a weakness.
  2. Asking for help.
  3. Feeling OK with “putting more work on someone else”.
  4. Clarity and specificity in delegation to freelancers.

10 person startup team

Good delegation starts to be about functional ownership and clear role expectations.

Yes, people still need to play to their strengths, but leaders are now responsible for setting clear expectations not just at the task level, but at the role level. If the requisite strengths to deliver on a role are not there, there has to be a replacement or a reshuffle.

The organisation is still very flat, and leaders are extremely close to all deliverables.

Delegation at this scale often has to start happening in some sort of task management system, helping to enforce clarity and avoid tasks falling between chairs.

Delegation is now also a tool to grow team skills.

Sticking points preventing effective delegation:

  1. Setting the right people in the right roles.
  2. Lacking task management (leading to lacking overview and follow-through and follow-up)
  3. Avoiding the temptation to “do it better” than a subordinate.

30 person scaleup team

Good delegation now starts to involve letting go of details. The organisation is approaching maximal size to continue with only 1 layer of management, as the amount of direct reports is becoming unmanageable for the founding team (depending on structure)

Projects are defined broadly by leadership, and the way to deliver on them is further defined by subordinates.

Functions in the org are well defined but still flat.

Sticking points preventing effective delegation:

  1. Accepting that you can’t see all the detail anymore.
  2. Accepting that you’re “losing touch” with things you used to be really good at.

100 person scaleup team

Middle managers. Middle managers everywhere!

Good delegation from C level includes setting broad strategic objectives and making it extremely clear to the middle-management team why the strategy is a good one. Then it’s also about communicating loud and clear to the entire organisation again and again what the direction is.

Good delegation from middle managers now involves making strong connections between the project/task level and the strategic direction. It has to be clear what we’re doing, and why we’re doing it (i.e. how it helps with the company direction).

Functional units may be approaching the 30 person size, meaning functional managers are hitting the sticking points from the previous stage, while C level is encountering new challenges.

It’s important for C-level and middle-managers to start being aware that cross-functional delegation ACROSS THE ORG may start to slow down - at this size it’s still manageable by taking people by the hand and bringing them into a room to talk things through. It’s necessary to build and maintain strong working relationships across sub-teams. At the first sign of silos happening, it’s time to take a large sledgehammer out and smash them to pieces.

Sticking points preventing effective delegation:

  1. Feeling like you’re not doing “real work”.
  2. Not communicating in a way that builds a following. Leadership needs to step up to a new level here. Be someone worth following.
  3. Allowing silos to form.

300 person maturing business

2 scary things happen on the road to 300.

  1. C level disconnects from front line.
  2. The “close tribe” feeling breaks because of size. Humans can typically only feel lasting, strong tribal connection to a group of somewhere between 100 and 150 people, depending on the person. 300 means AT LEAST 2 tribes forming.

Good delegation is about ALL the things it has been about so far, but now with an extreme focus on facilitating delegation of work between the inevitable tribes that have spawned. The tribes must be kept friendly.

C-level can pretty much only work through culture and strategy, and are so far from front-lines that special care must be taken to retain an understanding of the customer and the value creation in the business.

Functional VPs set the direction of work as C-level releases the reins.

At this stage, the operations function probably has some hand in workflow management, instead of only direct value chain ops.

Sticking points preventing effective delegation:

  1. Seeming out of touch / actually losing your connection to customers and the true value creation of the business.
  2. Allowing the emerging tribes in the organisation to build friction that prevents effective delegation.
  3. Someone from the C-level still having opinions on front line execution (i.e. undercutting their chain of command)
  4. Ossified processes - process MUST update dynamically to support the reality of the operation, and front line must be enabled to make those process changes.

1000+

…? DM me if you know.