The Magic of Middle Management: Pure Career Upside

Introducing the Abacus & Pencil Career Framework

Last week, when I asked the question that has been bugging me for years (Why aren’t we hiring leaders based on their ability to build teams of lieutenants?), I received some incredibly thoughtful responses and follow-on questions from many of you.

If you missed the previous post you can read it here.

Let me summarize them below – I’ll touch on some of the underlying themes today and address others in depth in the coming weeks.

1. With the right product you can get to $100M ARR without any mid-level management. Why can't you just hire those Directors and VPs later?

2. Without intentional and ruthless clarity, you move slowly, or not at all. Will you inevitably destroy your culture in the process?

3. What should I do if finance won't let me pay the $$$s required to attract the upwardly-mobile high-performers that will form our next layer of leadership?

4. How do you match people's horse power with their career path vs. their point-in-time experience or prior job title?

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First, we need to understand what middle managers do. And explain why they aren’t just paper pushers (or rather, shouldn’t be).

When I talk about middle managers I mean the two highlighted rows below in the Abacus & Pencil Career Framework. I have developed and used this framework over the last fifteen years – from structuring my own career, mentoring my teams, to guiding my clients. This view of the career ladder has held true across Fortune 500 companies, Series A/B/C startups, and pre-IPO unicorns.

The framework is self-calibrating: it helps you determine the appropriate level of talent for each role based on the expectations of how they relate to everyone else around them. Of course, an Engineering Director at Google is a totally different kind of role vs. a Customer Success Director at a $15M ARR Series B startup – but that difference is captured in the ability to influence your peers. This makes the framework portable across industries and company stages.

There’s a certain magic that happens as we move through that middle manager layer.

The difference isn’t that the more senior you are the more decisions you make – everyone, down the the newly hired SDR, makes $1M+ decisions (e.g. by choosing which leads to qualify). The difference is whether the direct consequences of the decisions you influence are borne by you and people in your direct reporting line vs. elsewhere in the organizational reporting tree.

The middle management layer is where the balance is struck between having the context-specific expertise to go deep in one area every day vs. having the ability (and time) to step back and understand goals that you’re not directly responsible for.

The key is that the second part of this balance (stepping back to dig into goals you’re not responsible for) is in many ways optional.

Directors don’t get fired because they failed to connect the dots between customer success and engineering. Afterall, they’re not responsible for org. design or setting strategic priorities.

This means that, as a middle manager, you have only career upside (no downside), if you carve out the time to help lift up your peers.

It’s precisely this career risk-free opportunity to connect the dots that encourages a middle manager to raise their hand and say: “Hey, that story we’re telling investors doesn’t match what the teams are doing every day.” or “There’s a risk nobody is talking about, and I think it is my job to surface it for the leadership team.”

AS A LEADER IT FEELS LIKE PURE MAGIC WHEN YOUR TEAMS ARE CONNECTING THE DOTS THIS WAY. When they close your blind spots without even asking and start operating autonomously across reporting lines.

What does this mean for a VP or CxO?

A strong middle management layer enables VPs and CxOs to do their best work. A CEO cannot influence teams at scale - set the culture and direction of the company without having 1:1s with every employee - without VPs to reinforce it across the teams. Similarly, a VP won’t have the time to reinforce that direction and make thoughtful muti-quarter decisions around it, if they’re busy coordinating day-to-day execution with a dozen other VPs, or, worse, holding their ICs directly accountable through constant check-ins.

This means that leaders can’t live up to their full potential without the shoulders of middle managers to stand on.

There are always exceptions to the rule (I’ve met some), but exceptions don’t scale.

Let me illustrate that using the same table.

Without a middle-management layer the burden of cross-functional coordination falls down to the IC level and devolves to being tactical – and, as a result, upward feedback on strategic decisions gets stuck with teams too busy chasing weekly goals.

Over the course of this quarter I’ll keep exploring this question: Why aren’t we hiring leaders based on their ability to build teams of lieutenants?

Next week, I’ll talk about where on the path to $100M in ARR this goes from a nice-to-have to becoming an existential risk.

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