Overview

tldr; Generalists are useful for injecting energy

I’ve recently moved from a large company (~1000 people) to a small company (<10 people), and it has given me a new perspective on the usefulness of generalists. I have spent most of my career working in small companies, and moving abruptly from the largest company I’ve worked for back to a small company has shed some light on the differences for me.

Here, I’d like to focus on how I see the utility of generalists, and their roles inside companies.

Generalists in bad faith

First, I’d like to address the elephant in the room related to being a generalist. I have often see people refer to themselves as “generalists” because they actually weren’t very good at anything - hence “jack of all trades, master of none”. I have referred to myself as a generalists while trying to defend my ego from people who were much more competent than myself.

For the purposes of this post, I’d like to refer to generalists in good faith. That is, people who are truly competent at a broad array of things. The most common trait that I have seen among generalists is that they get bored very quickly if pigeonholed. It is unlikely that you would find a generalist toiling away on the same problem for years unless the problem is highly complex and multi-faceted - like, say starting a business.

What do generalists do?

What I have seen of generalists is that they tend to add energy to the projects that they are working on because they like bouncing around to everyone else’s job. If you don’t have an “everyone else”, then this arrangement works out very well. This leads me to a single rule (here specified as two sides of a spectrum):

1. If you want to get nothing done on a large project, add generalists
2. If you want to get anything done on small projects, add generalists

Generalists can move the ball forward on many fronts, and they often have a knack for seeing where things are lacking due to their expertise in many things. This makes them crucial to small projects because they can see and fill holes that others won’t. However, they can cause havoc on larger projects because they will be stepping on toes.

Stepping on toes

I’m going to make up an example to explain how generalists may cause problems on larger teams.

Let’s say that it’s Bill’s job to do unit economic analysis. New information is presented to Tanya the Generalist (now officially employed as a marketing manager), and she wants to understand unit economics more deeply to make marketing decisions. Fortunately, she used to be a financial analyst at a medium sized business. She uses Bill’s original unit economic analysis to make her own. As a singular incident, this may actually be great. The team has an improved unit economic analysis, and the marketing decisions were made quickly.

But what if this happens 3 times a week? If it’s only Tanya, this might be fine. Indeed, Tanya may be greatly rewarded for her initiative.

Let’s take it a step further, and say that this project has 75 people, and 25 of them behave like Tanya. On smaller teams, this behavior was rewarded, so we should certainly not fault them for acting this way.

If 25 people are constantly creating new unit economics models (ok, this example is starting to feel stretched, but bear with me), then why is Bill even there? Who should use which model? Which one is the most up to date? Tanya made a really useful one the other day, but now Rob has yet a different one, and Arjun will have yet a better one tomorrow. Now, everyone is going to Rob, Tanya, and Arjun (and maybe several others) for their unit economics model.

What they should do is send the information they have to Bill, and let Bill manage the model. In this case, making their own models may be a way to communicate this which would make the problem much less severe.

But remember, these people are generalists. They don’t just do 2 things, they do lots of them. Now they’re also drawing up designs for advertisements, reaching out to prospects, and changing priorities of the engineers. Obviously, on a large project, this would be chaos. If things got done, they would happen in spite of the generalists, not because of them. These projects need people who are focused and dedicated to a single function.

However, if you’re short-staffed on a small project, these people are a godsend. Keeping them busy with a few different roles will keep them happy, and it will make your understaffed project acheivable.

Where to put generalists

It is easy to promote generalists to management because they are able to see the holes between teams and have a desire to work more closely with members of other teams and departments. However, the movement to management should be more carefully considered. It is often (but not always) the case that managers need to execute a specific set of routines in order to be good managers. If these routines are rigidly defined, management will not be a good place for a generalist because these routines will bore them as well.

The most successful places that I’ve seen for generalists are either small companies that need people who can wear many hats or at large companies in positions that act like consultants. Both of these types of roles allow the generalists to move between projects and priorities; keeping them happy, helping the company, and minimizing chaos.