The ‘Great Blue Hole’ in Belize, a popular dive spot.

Dan Jacobs from Apple was famously quoted once: “I’d rather have a hole in my team than an asshole in my team.”

When our founders thought about how to build out the different parts of Skyport they spent a lot of time first talking about the culture they wanted, the organization values that they wanted to in the end pervade the group so that people would default to ‘doing the right thing’.  We often talk about some of the great organizations we have seen where fifteen to twenty years after organizational genesis people were still talking, almost reverently, about the founding team members who set the cultural tone.

One that always stood out in my mind was cisco Systems’s New York sales organization.  People like Bill Nuti, Nick Adamo, Chuck Pease, and Carlos Dominguez were but a few of the early team there that built a great and lasting culture.  Was there any one thing, no.  There were hundreds of little things that conspired to create a lasting and pervasive culture that was stronger than the individual – thus employees in order to thrive and survive must apart to the culture rather than try to change it.

A few examples that always stood out for me of these types of things:  Chuck Pease would Fedex bagels to the cisco engineering offices in Menlo Park on most Friday’s.  This built a rapport between sales and development.  This kept development keenly aware of these crazy guys on the east coast asking them to do some very special features for the financial customers.  It also showed respect.

Managers were usually famously protective of their teams, sometimes to a fault: if a candidate who was a top-performer on your team was up for a promotion to some other part of the company some managers would do whatever they could to keep the candidate on their team: including lowering their performance evals, threatening to or reducing stock option grants, etc.  Not the NYC team.  When a regional manager was getting promoted to run enterprise sales for Germany the entire office showed up at Tir Na Nog on 8th Avenue and celebrated his success long into the night, giving him a plaque and cards signed by the entire office.  They thought bigger than their own slice of the world.

Bill Nuti was a very skilled sales manager, but he always told his account managers to make certain the systems engineers never once bought lunch or dinner.   This broke down the caste system and barriers between organizations that sometimes had a bit of friction or resentment.

At Skyport we started with a question, “what do we want our culture to look like and what steps can we take to create the type of culture that lasts?”   The founders wrote down their thoughts, creating the ‘Culture Manifesto’.  But more important than even a document is how do we implement and create it.  There’s a few things we’ve started with:

Every Friday we do a company meeting, just for an hour.  The leadership team spends a bit of time with a broad update, each individual is given the opportunity to talk about what they worked on this week and any goals for next week.  Our main goal is to keep everyone talking, keep the lines of communications open, to ensure that people know who they can reach out to quickly to solve a problem.

We don’t do daily free lunches and dinners.  We don’t want to create a culture of entitlement.  But we did site the office in the middle of one of the most robust and vibrant dining scenes imaginable for a plethora of food choices.  I have three decent sushi spots and an amazing ramen place within a few steps and one of the best Mexican restaurants I have ever set foot in just around the corner.

We invited some of the sales team to sit in and participate in the product team meeting.  This is highly unusual – but the feedback from the sales team, empowered and required to be the tip of the spear with customers, is direct and informative.  This also helps us break down the castes that often develop in companies.  I’ve seen before where groups are treated very differently and look down their noses at other parts of the company.  We always try to stress that each part of the business from GTM to Development Engineering to Finance/Operations has a dependency on each other and under no circumstances should we lower the bar in any part of our business on who and how we hire.

Hiring is the most critical success criteria though.  Hire well, and the formative culture we are creating becomes pervasive and quickly is reinforced and strengthened.  Hire poorly and we create frustration and angst — but usually in the people we most want to retain.  So how do we weed them out in the interview process?  How do we ensure we are not bringing the wrong people on?

We instituted a few practical principles we’ve seen work well at other companies.  Each candidate goes through at least five, sometimes up to twelve interviews.  Most interviews are designed to focus on cultural fit and alignment more than just grilling them with technical questions to prove who is smarter.  After the battery of interviews the interviewers all get together and have an open discussion about the candidate – we always try to have the people with fancy titles present their views last so they don’t artificially influence someone else opinion.  I have always felt the admin or coordinator has a major seat at the table here: if any candidate is ever disrespectful to them they aren’t going to grace our doorway.

I always ask myself three questions at the end of my interview of someone.

  1. Would I invite them skiing with me for the weekend?  This means I am willing to accept that I could get stuck in bad weather in the car with them for 6-8 hours and not be thoroughly sick of them.  If I hire this person they will be spending a lot more than 6-8 hours around me and if I don’t genuinely enjoy their company I will most likely not spend the time with them that is necessary to ensure organizational success.
  2. Would I lend them my car?  A sign of trust.  I keep a car at the office and leave the keys with the office manager so that if anyone needs it because CalTrain stopped or they have an important errand it is there for them.  If I can’t trust you with my car how can I trust you with something that is of much greater value – our company.
  3. Would I invite the candidate to a dinner party with friends/family?  If I am worried about how they would represent yourself around my friends how can I trust them with our customers and partners.

In the end we tell every hiring manager that culture is 51% of the hire.  Even in systems engineering where technical prowess often reigns supreme we’d rather have a mailing list where no-one causes a flame war or writes those emails we have all read that are designed to show off how smart they are and make others feel inadequate.  If you are great technically your job is to make everyone around you better, not just to make yourself look good.

When we do systems engineering technical interviews we like to ask questions like, “What are the first 13 packets that hit the wire after you type into a web browser assuming all caches are cleared.”  But I’ve hired a candidate who forgot the ARP lookups, had no concept of DNS recursion, and missed the TCP session setup.  Why did he/she get hired?  Because after the interview they researched the question and wrote down the correct answer and emailed it to me.  Just like a good SE does when they don’t know something – they admit it and then follow-up accurately and quickly.

The last question we often ask of a candidate is a scenario: “It’s Friday night, your customer just had an outage and they requested you onsite Saturday evening at 10pm for an emergency change control.  The problem is that Saturday eve is your (anniversary, kids mother/daughter camping trip in Yosemite, father/daughter dance, thing you can’t get out of that has no cell/Internet access).  What do you do?  Do you support your customer or spend the evening with your family as you had planned?  The purpose of this question is to see what they prioritize and if they think linearly or not.  (Before you flame me, read to the end please.)

I can’t say its foolproof – I’ve still had to let some people go for cause, and others primarily because in 6-9m they never ‘got it’ and were off by themselves.  One of my best managers, Darrin, and I used to watch our groups at a sales meeting and see who was the ‘lone sheep’ off by themselves and not hanging with the rest of the group — we were batting 1.000 on predicting their likelihood to stay for the next year when last we looked at our picks.  If the culture is strong and the management actually leading more than just managing then the teams tend to stick together and take care of each other.  When you have to cut, cut early, don’t let them fester – its not good for them, you, or the rest of the org.

As to the correct answer to the whether to put job or family first when faced with a tough decision like the scenario we laid out – there isn’t a wrong answer, but there is a best answer.  We personally prefer the candidate who won’t let their customer down, and won’t let their family/friends down.  We want the candidate who looks at the A/B choice and picks C.

C is – ‘I call my manager or peer and ask them to help; I explain the situation and they jump right on helping me because I’ve done it for them, no questions asked, before and I’ve documented the customer situation well enough that it can be a seamless handoff.’

In summary, in a startup hire people you trust and genuinely want to be around.  They don’t need to be your best friend, they need to be someone you want to spend a lot of time with solving really fun problems who you can respect and who will respect the organization they are a part of.