Remember when it was just the five of you – three co-founders and two devs? You were flying from city to city knocking down your first few big contracts. Every Uber ride and hotel night was a flurry of emails with your co-founders – COO and CTO – implementing your first few customers and steering your first two developers towards product market fit. When you got back to the office Thursday evening from three days on the road, your team was still nose to the grindstone at 8pm. All hands on deck, rowing together.

On your last trip, you got back to the office from a major contract proposal – $1M ARR! But the office at 6:30pm is a ghost town. 15,000 square feet with 200 desks and all you see is a smattering of developers and two SDRs flirting with each other. Why doesn’t everyone work longer, harder? Why aren’t they more committed like you?

Does this sound familiar?

The truth is things probably started changing between 25 to 50 people. A startup’s evolution is like the human journey from hunter/gatherer tribes to complex societies with specialization. The scale and timelines are different, but the analog holds. In humanity’s early days, we operated like a just-founded startup: a small extended family unit that trusts each other and carves out very broad sections of responsibility: hunting (sales), gathering (implementation and customer success), and child/family care (product)… or something like that.  For the most part, everyone did anything they needed, because a loss or win for one member equally affected the others, largely based on shared DNA (equity) and an inherent motivation to continue that line.

A small town of 200 people or a modern city of 1M is different. Most citizens are not family members, and the town or city thrives based on job specialization and a common currency of money, not DNA. Likewise, somewhere around 25 people, a startup begins to rapidly specialize. In sales, you now have SDRs, AEs and managers. In product/tech, you  have developers, dev ops and PMs. And while most new hires have a little equity, junior and mid-level hires tend not to place much value on it – a sad truth. Employees are now mostly motivated by cash, affiliation (also known as culture) and the opportunity for self-advancement.

So now we understand that motivations have evolved, but is it a problem that people aren’t in the office until 8pm like they used to be? In fact, this shift can be a positive sign of a startup’s maturity:

You’re hiring more senior people: Experienced hires have families. They like to be home to put Sue and Skippy to bed, and they require much less “on the job training”. Both mean fewer hours in the office overall versus an inexperienced predecessor or team member. However, experienced hires should also be happy to hop on a plane any time or hammer through some emails after children’s bedtime.

Sales is processifying: There is a basic reality that sales people cannot sell at night – prospects don’t want to talk then. Sure, they can update notes, prioritize leads, schedule emails, etc.. But guess what? When sales process is humming, those activities are done contemporaneously during calls or with the real-time support of a good sales tools stack and sales ops function. For sales people, evenings are for hitting the gym and pounding protein shakes… or whatever it is they do.

Growth is not a successive journey of firefighting: Startups are a marathon not a sprint. If every day is a new firefight, people won’t stick around. A calm but intense culture with a regular working pace can be a sign that your people are on top of things.

However, empty offices at 6:30pm can also be a bad sign if associated with any of the following:

Where are the developers? Developers tend to start their days later and end them later too. Night creatures – or maybe it’s to avoid screen glare from the sun. It would be concerning not to see some tech and product folks hanging around well past 6:30pm. You can work on product at night!

Too much layering: One of the first things that can happen as a startup gets bigger and adds management layers is managers push too much down to reports instead of running the ball themselves. Bad sign. This is especially true for “support functions” (anyone that doesn’t build or sell, like finance, recruiting, ops, HR) Everyone wants to be a leader. Fine. But everyone still needs to do work. I’ve seen 7M ARR startups with three person finance teams. That better be a sweeeeeet board deck.

Lack of accountability: Accountability is measured in process and outcomes. On the process front, when you ask people questions, do they have the answers? Or do they point to other people? Is everything becoming a group decision? On the outcomes side, I view things bi-modally: (1) outcomes that are controlled perfectly internally by an organization (product launches, financial reporting, budgeting, etc) and (2) outcomes that rely heavily on external factors (sales, partnerships and hiring). Misses of the second mode don’t necessarily mean you  have a company or culture problem – startups are hard, and there are a lot of external factors that affect them. But if your team is consistently whiffing things it perfectly controls, there is for sure a culture problem.

Missing numbers with excuses: Despite the realities of externalities in outcomes you don’t control, they should never be used as an excuse. Welcome to capitalism!

Inflexibility to heroic undertakings: While persistent firefighting is a problem, team members should not hesitate to grab buckets when a conflagration appears. Resistance to last minute travel, pulling a late night or working a weekend when needed spells trouble.

So how does your growing startup stack up?

One thought on “It’s 6:30pm. Do you know where your team members are?

  1. Great post. The great ape tribe or the anthill. Different sizes & modes of organization. Fact is we’re happiest & do our best work in the former (no surprise). So how to we take that organizational mode & make it work at scale?

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