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Less Annoying Business: The trap of hiring early employees to be future leaders

published11 months ago
3 min read

Hey Reader,

Tyler from Less Annoying Business here. Here's what's new:

New content

The trap of hiring early employees to be future leaders [Blog post]
A mistake I've made, and seen others make, is assuming that the first employees you hire must be leaders as the company grows. First and foremost, early hires need to be doers, not leaders.

Bootstrapping a software business built on WordPress with Lesley Sim [Video]
I had a conversation with Lesley Sim, an entrepreneur bootstrapping a small software business. In this conversation, we workshop some ideas related to challenges she's facing.

What I'm doing

The last few weeks have been unusually calm. I've had way fewer meetings than normal which gave me the most time for individual contributor work I've had in recent memory. I mostly spent that time thinking about LACRM's long-term strategy which led to a lot of design work (our product design is core to our strategy).

In particular, I've been thinking about how a task list should work. We need to give our task feature an overhaul, and once we do, that's going to be one of the key parts of LACRM that our customers interact with. Most task tools are unopinionated. They let you make projects and put tasks in those projects, but it's up to you to figure out how to structure all of that. I'm playing around with a more opinionated approach that has a built-in workflow rather than just leaving it up to each person to figure out. This is an extremely rough draft, but if you're interested in a preview, here it is.

I also recorded a test episode of a potential new podcast with Dru Riley. We haven't published the episode publicly yet, but I'll share it in a future newsletter. Our plan is to record a handful of test episodes to see how we like it. If the experiment goes well, we'll make it a regular thing.

What I'm reading

Small Giants [book]
I'm not much of a book person, but I just started reading this one at the recommendation of a newsletter subscriber (thanks Michael!) and I'm loving it so far. It examines a handful of businesses that chose to be great instead of big, and a lot of the lessons echo the things I've learned at Less Annoying CRM. A few takeaways so far:

  • Most small giants are "human scale" meaning they're small enough that everyone at the company can know everyone else. This is something I've thought a lot about as LACRM grows. I've heard that around 30-50 employees is where it stops feeling like a single team, and instead it's several fragmented departments. It's often worth it to grow beyond that size, but it doesn't have to be a given.
  • How much does speed matter vs. size? The book makes it sound like slowly growing past the "human scale" threshold is much more sustainable if it happens slowly.
  • Does a business have to "grow or die" as people often say? Not necessarily, but if a business isn't growing, it can be hard to retain ambitious employees because there aren't new opportunities. But as the book points out, there are different types of growth, and they don't all require the team size to increase.
  • Fast growth requires capital, and if you raise that from outside investors, you're limiting your options. Investors expect you to maximize their returns. Once you hop on that rollercoaster, it's almost impossible to get off.

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Josh Pigford
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September 13th 2021

This is an interesting reflection from a founder that originally planned on hiring exclusively "fractional" employees (part-time contractors).

This seems to be a growing trend. I completely understand the idea of not wanting to deal with all the people management aspects of running a business. As a matter of fact, Bracken (my brother/co-founder) and I wanted to do something like this in the early days of LACRM.

But at the end of the day, unless you can avoid hiring employees/contractors entirely, you're going to need to manage people. It doesn't matter how many hours they work or what their tax status is. People working together require coordination, and there will inevitably be messiness that comes with that. That's part of the job, and I question whether hiring fractional employees really gets around that.