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Stuck in the Middle (Management) With You.

Middle management isn’t sexy, but it’s essential. It’s not a dirty word. I'm a middle manager and I'm proud.

October 15, 2019

When I started my career at the turn of the century, middle management was perceived to be a dirty word, a word that expressed incompetence and inefficiency.

At the time they were blamed for not being able to deliver multimillion pound epic four-year waterfall projects. It couldn’t possibly be the senior managements fault. It had to be the bureaucratic middle managers, who had no measurable output. So must be not doing anything useful.

There was a craze for ‘flattening’ company hierarchies and removing these besuited morons, allowing communication to flow better through the company.

There were some truths in this, but we were only really starting to understand the benefits of agile software development and smaller teams. At this point, people didn’t seem to realise that it’s impossible to estimate how long a software development project takes pasts a few weeks and where committing to contracts spanning years with set requirements.

Middle management got the blame, and it became a dirty word, even a punch line in jokes. It was used to categories the kind of boring, besuited, middle-aged guy who has elevated himself to his1 highest level of incompetence. Who probably drives a Ford Mondeo.

The return of hierarchy.

Recently, as I progressed through my career, I’ve noticed that companies seem to be naturally returning to more hierarchical structures. They are focusing heavily on smaller, more agile, empowered teams.

If you keep you follow the Bezos pizza rule and keep your teams ‘small enough to be fed by two large pizzas’ then you naturally need a tree-style reporting structure.

For example, even if you consider a company of 240 employees with an average team size of 6. You have 40 teams, if all apply the new work manifesto rule that ’40 hours are enough’ then if all of the teams report to c-level, they all get precisely one hour of higher leadership time a week. This example excludes that c-level having any time for any deep work.

So you need to add levels in-between and the larger your company grows, the more levels you need. Consider it as a binary tree, the larger your data set, the more branches you’re going to need.

These levels become the critical communication and guidance system for the entire company. There is no point in having fantastic leadership from the top and remarkable tech talent to implement the idea if the communication between those two elements is terrible.

You are not sexy.

The challenge comes from the perception of middle management; no one sees this as sexy. Not one single thought leader stood on stage at a conference and put ‘Middle Manager’ in their intro slide. It’s not perceived to be sexy. This opinion is bullshit.

Middle management plays a critical role as companies try to work out what the next ‘new work’ manifesto they want to implement this week.

One thing that I think we’re beginning to understand is that two things do tend to work in software development:

  1. Small, tight, delivery teams.
  2. Agile development. Both of the above are great, but add a significant amount of overhead to all processes. You have to decentralise a lot of people management skills that can’t be performed by higher management.

Imagine trying to set and review delivery expectation for more than eight people, or trying to manage personal development plans for 20/30 reports?

What we do is hard, and we’re fantastic.

The more I write, and think, about what it is to be a people manager in tech, the more I realise it’s fucking hard. You have to keep an eye on so many different things, you can’t focus on developing one speciality because your team will all demands different things from you as the team grows and prospers.

To give your team the best service you need to be good at so many different skills. In this situation, the stereotype of the generalist no longer fits. The “Jack of all trades, master of none” moniker no longer fits. You need to develop skills quickly, that means you can act as the master of everything when the master isn’t immediately available.

It’s ok to feel overwhelmed by this, and it’s ok not to be prefect. However, it’s not ok to be ashamed of your position. Being a great middle manager is something that should be revered.

I’m proud to be a middle manager.

All hail the middle managers.

  1. I know, I know. This example is intentionally gendered because it’s a historical story and it would, invariable, be a man.

Phil Bennett

Phil is an engineering manager at Klarna with 20 years experience in the tech industry. He has an empathetic team lead who is always striving to get better at helping others get better. He also has an unhealthy interest in burgers.