The life cycles of tech executives

I often describe the evolution of a company as an upwards spiral: you keep progressing and you’re also on a continuous cycle of having to re-evaluate parts of the company for the next level. One of those evaluations is of executives and their ability to continue to lead the functions they are in charge of. Here’s a rough framework I’ve found helpful.

First, by “executives” I mean third line managers, that is people who manage people who manage people who manage individual contributors. Naturally this implies a stage and scale of company (things are much more hectic and fast paced at an earlier stage) and also functions (a VP-level IC hire doesn’t fit in this model).

Executives’ cycle is generally 2 years long and is divided into four 6-month phases (roughly similar to the forming-storming-norming-performing model of team building, another one of my favorites). The absolute length of the phases conforms to the speed of growth of the company but only by a bit – I’ve noticed the same at FraudSciences, Klarna, PayPal, and TrueAccord at different stages and velocities.

Stage 1: acclimation. The executive is settling in, learning the ropes, understanding where the bodies are buried. At this stage you’re either sighing a big sigh of relief because you’ve hired someone to take a huge chunk of work away or (hopefully rarely) get the sinking feeling that you hired the wrong person. This is the time to correct that mistake. Quick learning executives or ones putting out dumpster fires will have some positive effect even at this stage.

Stage 2: transformation. The executive learned the ropes and is starting to make changes. They may hire new people to replace non-scaling team members, cycle through talent, re-negotiate operating mechanisms with you, and so on. This is when you start seeing their playbook in action, and the seeds of future performance are planted. This is also when this exec will be torched on Glassdoor or in exit interviews for “not getting it”. This is not necessarily a bad signal.

Stage 3: performance. Under-performers are out, new team is in, playbook installed: this is when you’re getting the most out of your exec.

Stage 4: scale. Having promoted or hired their staff, the executive can now extract themselves from daily operations as much as possible, negotiate operating mechanisms with their directs, and be ready to move to the next level of abstraction: take on more responsibilities or deal with, for lack of a better term, “strategy”, as contrast to daily tactics. That means planning ahead, designing their organization, developing new capabilities, and improving cross-functional work.

Interestingly, not delivering in stage 4 is a very common yet often disregarded failure mode for executives, and it’s allowed to fester until they buckle under the weight of daily responsibilities and burnout. I spend a considerable amount of time pushing my directs to enhance their bench, if only because of my own experience of not having done that.

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