Cowboys & Villagers – Simple Thoughts on Hiring

Cowboys & Villagers – Simple Thoughts on Hiring

Your first hires were probably mistakes. Mine were disasters; they demonstrated humanity's fascinating ability to self-implode. Hiring is hard.

You'll probably begin by hiring people who look like you. Not demographically (right?), but people who share the same traits you share: hard working, perfectionist, and maybe even unforgiving. Or, you've hired people you want to be friends with – people you'd enjoy going to a concert with or perhaps carrying on a different type of relationship with (i.e. platonic).

So while I was digging a bit deeper into SaaStr this evening I came across an interesting discussion between Sarah Lacey and Slack's CEO, Stewart Butterfield. Slack is a team of 40 year-old plus employees. Slack doesn't screen for age, but the company does focus on building a village. Not a frat. How many times do we as builders have to learn these lessons?

This clip highlights the struggle of managing towards a culture with balance and purpose. Sarah discusses with Stewart the work / life balance at TechCrunch with grueling hours and punishing schedules. This thought is then juxtaposed against PandoDaily, where she takes the marathon approach of business building.

These two conclude by discussing the design of a business foundation that is mature and respectful: hallmark traits of a dependability and resilience.

Deviating from the narrative they've laid, my experience in hiring and development of employees leads to my understanding that short-term benefits of bringing on cowboys – my way or the highway folk – comes at the cost of any long term benefits. The rapidity of responsibility delegation is only matched by the rate at which they hand it back on their way out. Cowboys don't stick around; they're cowboys!

Following from that philosophy, there are two hiring questions I fall back on during the candidate screening process:

  • what do you want out of this experience?
  • what resources do you need to call on to be successful?

The first question is about alignment and fit. If my needs (as a hiring manager) and your desires are aligned, we can do business today and work in a common direction. If there is a mismatch here and yet I advance the candidate down the hiring-pipeline, I ought to soul-search about what I'm trying to accomplish. I (read: you) need a reality check.

The second question – really a topic for another day – should help you determine whether the candidate has been there before or whether they're just a Peter principle candidate.

Building a village in your business is about hiring function-focused staff who are able to provide excellence and depth for today's needs. The villagers take pride in their work and stay firmly focused on improving themselves and the village. They demonstrate ownership and long-term buy-in. They often idolize the cowboy, but realize those dreamy nights spent under the stars are often spent alone.

Remember, you're also a villager. Yes you, the founder, the exec, the CEO. It is up to you to as mayor to bring in good citizens. More good citizens will follow.

Or don't. Develop organizations that lack the fundamentals of dependability and resilience. Your villagers and best talent will exit alongside the cowboys. They'll just be headed in separate directions.

Devin Fee

Devin Fee

I'm a father, and engineer turned businessman. I have built my career in the world of early stage, venture backed businesses.

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