When should my startup hire senior executives?

Executives who chase money instead of mission are criticized as sellouts.

But some people point out lots of other people were only pretending to have principles.

Being able to turn nothing into something deserves respect.

Those lines paraphrase Kanye West’s “New God Flow” featuring Pusha T and Ghostface Killah.

Artist: Kanye West

Track: New God Flow featuring Pusha T and Ghostface Killah

Album: Cruel Summer

Year: 2012

Labels: GOOD and Def Jam

Go Hire Some Grownups

A certain clutch of board members has one piece of advice for every fast-growing founder: go hire some grownups to run things. But it can be hard to know which business is in the best position for grownups, and it’s even harder to figure out which jobs should be filled with them. You need someone who already knows how to do the things you don’t. But where do you find the right people? How do you hire and manage them?

You probably also fear that bringing on experience will wreck your startup culture. You’ve got a team full of young, dedicated people and you’re afraid that hiring someone old and accomplished will wreck the vibe. Maybe the veteran will swagger around wearing a suit and order people to look at their sales reports. Those worries are all sincere, and they may be true. So take them seriously. The right outside hire can mean the difference between a failed startup and a triumphant one.

Startups are desperate for time. They exist in a permanent race against an oncoming wall. Good ideas go stale. There are only so many years left for employees to bet their lives on a dream. (Most lose faith after roughly five or six years.) So imagine that Mark Zuckerberg had decided to launch Facebook only last week. The company would need to build all the same products in much less time. The right team of veterans can sharply shorten the road.

Hiring an outside executive is like taking steroids. When it works, your company grows to sizes you’d never reach alone. When it fails, your company rots from the inside.

The only strong reason to hire a big executive is specific knowledge and experience. If the ability is vague or unspecified, you’re just going to freak out the team and waste your money.

Maybe you’re a technical founder and you don’t know how to build a global sales channel, create an unbeatable brand, or strike partnership deals that change the landscape. A world-class senior hire can accelerate success in any of those areas.

The key question when you hire someone to manage an existing team is: Will this person need more outside knowledge or inside knowledge? Which set of knowledge is more important? If it’s inside knowledge, promote inside. If it’s outside knowledge, hire from the outside. Engineering managers, for instance, often should be promoted from within. They need knowledge of the codebase and of the team.

Enterprise sales often requires outside knowledge and experience. The ideal head of sales will have a world-class understanding of customers and a keen ability to hire salespeople from all over the world. As a result, promoted heads of engineering often succeed, and promoted heads of sales almost always fail.

Managing Veterans After They Join

Managing veterans after they join

Running veterans is as hard as hiring them. The big problems come from culture, politics, and accountability.

One is their previous company. Every executive brings a set of ideas and assumptions about how businesses work. Most of those lessons were learned in a much bigger, more structured environment. Those lessons won’t fit a startup, but the new hire won’t know that.

Two is navigating an unwritten organization chart. Veteran executives have mastered it at large companies. That experience, though, looks awful to a startup team.

Three is accountability. You hired an executive because you lacked the knowledge yourself. So how can you hold someone accountable for work you can’t evaluate?

The good news, though, is that all three problems are predictable. If you’re prepared for them, you can not only handle them but get the best out of your older new hires.

First, make clear to every new hire that their job is to adopt your culture, not adapt you to theirs. Maybe their old company really did have a better way to run some things. But don’t be tricked into changing too much, too fast. Past success is a powerful weapon but can become a dangerous excuse. You should adopt a better system only after a lot of thought.

Second, watch for politically motivated behavior and crush it without mercy.

Third, and most important: Setting a world-class bar is the most important thing you can do for your startup’s culture. You have to have a high and explicit bar. Tell all new hires that this is going to be a world-class company and a world-class team, and then actually do it. Focus only on bringing on people you’d be proud of no matter what age they were. Make clear, as early as possible, what you expect people to accomplish. Then don’t accept a B+ just because it’s better than your C.

Don’t set a low bar just because you don’t know what good looks like. Take public relations. Baby companies are cute. All they need to know about PR is how to draw attention to themselves. But awkward teenage companies are another matter. They need someone who’s good at making chicken salad from chicken shit. The best PR pros have spent years building deep personal relationships and learning every aspect of the industry. If the company’s story is weak, don’t set a low bar. Instead, bring on someone who can take the lousy story and make it look amazing.

So how do you set a high bar? Ask the experts. Find the best people in the field and just start chatting. Learn from them what great looks like. For instance, what would a great brand be for your company? Now take that lesson and keep it as your north star even if you have no idea how to achieve it. Part of bringing in a grownup is to get an answer you don’t know. You hire them to show you the way.

But setting the bar is not the whole job. Every executive, no matter what field, must master a set of skills outside their core. It helps to divide them into four basic areas.

One, there are the results against your objectives. A good bar, and measuring it, makes this part easy.

Two, there’s management. Even if the executive hits their numbers, did they build a strong, loyal team? So check on each manager and their team.

Three, there’s innovation and long-term thinking. Someone who hits their quarterly goals can still manage themself into long-term failure, so make sure there’s not a cost later. Say you hire an engineering manager and tell her to ship by the end of the year no matter what. She does it. But how can you know that the architecture won’t blow up when you release version two? Check on how results are made.

Four, there’s working well with peers. Start by talking with other executives to find out if the new guy has been supportive of them. Make sure they’re communicating with and supporting colleagues.

Are You Selling Out

Hiring veterans feels like a sellout. But maybe selling out is just an accusation that ignores what it’s really like to make something from nothing. But don’t leave things to trust. Learn the field and set the bar high. There’s nothing wrong with building something new, and you should feel good about yourself for taking the risk. But there’s also nothing wrong with hiring the best people to help you get there, whatever age they happen to be.