Scaling Your Product Org Fast. Ten Things to Know.

If you’re in the tech world, at some point in your career you’ll be part of scaling a product organization (engineering, product management etc) really fast. You may be a founder, a VP Engineering, Director of PM or a project leader of an engineering group.

Whatever your position, it’s going to be a challenging, fast-moving potentially bewildering time.

These are some of the larger issues that come up (having done it a few times, and coached people who are in the middle of it now), and how you might start to get to grips with them.

It’s not an exhaustive list. The good news is you’re not on your own.

tl;dr Version

  1. Yes, you’re doing it for the first time. So is everybody else. Get over it. The skill you need for the long-term in the tech industry is the ability to learn whilst keeping a clear head. Everything else stems from that.
  2. Work hard. This is an opportunity and there is much to do. Don’t grind yourself into the ground, but this isn’t a time to really get into balancing your life, either
  3. Know your cultural core values. Being clear here is a tool that will save you heartache and time when the crunch decisions come. Which they will
  4. Find, hire or otherwise determine your number 2 — somebody who complements you as a leader.
  5. Hiring is just time-consuming, exhausting and at its core, pretty simple: you have to see lots of people. Lots. More than you ever imagined.
  6. Yes, you’re going to need managers. You’ll be surprised how many are sitting in your organization now. Find them. Promote them. Don’t be scared.
  7. Engineers don’t like Managers (sometimes. maybe often). There are reasons. Have your organization be one that gets it right (that is: Engineers and Managers get along fine).
  8. Who defines the product? This comes up a lot. The Product Manager does. But there are considerable subtleties to this. I suggest you read the whole thing.
  9. Yes, you’re going to need some process: weekly staff meetings, one on ones, project reviews and decision points. Process does can be light-weight, elegant and effective. Learn to love it.
  10. Overcommunicate. There’s a lot going on. Make sure your team knows about it all — good, bad and ugly.

“Help! I’m Doing it For the First Time!”

Yes, you probably are. Here’s why it’s fine:

  • pretty much everybody else is, too — from Mark Zuckerberg on down to the most recent startup to get a seed round. Great companies are routinely put together by people who are doing it for the first time.
  • the skills you need are a) the ability to work hard (of which more later) and b) the ability and desire to learn. All the time. Without stopping. Everything else is temporary.
  • the nature of our business is constant, rapid change. It’s very rare that you will repeat a situation identically twice in your career. To some extent, you’ll always be “doing it for the first time”.
  • “I’ve done it before” can be a hindrance. Experience, particularly successful experience, tends to make you believe you know something. Which you may, but it may be the wrong thing. Example: two years of a successful turnaround may look great, but be completely wrong for a company that just needs flat-out expansion. And the reverse. A person who was super successful at mid-period Google my be exactly the wrong person for early-stage you.

So if there’s a voice saying “I can’t do this — I’ve never done it before”, just shut it down. There are other things to be concerned about. The Google guys did it. The Intel guys did it (referenced because I love the picture). You can do it. (And Ben Horowitz’s book is mostly about doing it all for the first time).

Work Hard, Take Time Off, Have Fun.

So I have a slightly (maybe) controversial view of work-life balance: sometimes it’s not appropriate. Sometimes the span, the arc of your life, is best served by really going for it. Scaling a product organization fast is probably one of those times.

If you’re successful, you will have created something terrific, something that pretty much everybody in the team will remember, and something that you can be proud of. You’d work hard if you were training for the Olympics, right? This is like that. But if you’re successful, you’ll probably make a lot more money, although you’ll be much less fit.

So work hard. Work weekends. Work evenings.

But wear it lightly. Yes, contradictory, a little. Here’s the (big) thing: there are a lot of hours to be put in and a lot of tough decisions to be made. But it’s not the end of the world. There will be other times and other places.

Consequently, don’t be stupid. Eat right, do yoga, pay soccer, go running, something. Stay at least a little bit healthy. Not enough hours to do all that? Yes there are.

And have some fun. We filled an entire floor of our offices with purple balloons, sprayed graffiti on the walls, went to the Ramp and got hammered on Friday night. (Yeah, I know, not original, but this was twenty years ago).

This is a pretty nice take on energy vs time.

(Oh and beware of things like the Bezos quote: “work hard, have fun, make history”. Usually a corporate slogan like that is code for “work really hard”. If you’re going to have fun, have fun, don’t talk about it).

Identify Your Cultural Core Values

Sounds a bit woo-woo. Like you should put it off. I don’t think so. Here’s why: at various points during the process of scaling, you will be faced with difficult decisions, mostly about people: who to hire, how much to offer them, how they will fit into a team that may not take to them, who to let go instead.

It will help, at all of these junctures, to have an idea of what you really value. An example: you can hire a killer PM from Google. But you’ll have to pay her 50% more than anybody else in the product organization. What do you value here? Excellence? Teamwork? Diversity? Fairness? Growth at any cost? And bear in mind that this is going to come out at some point. What are you going to tell people? How does what you tell them align with the values you have shared with them?

There will be others.

So how do you get to your core values. Here’s a light-weight process you might try:

Get the central team in a room for two hours. Be still and quiet for five minutes. Start to put on the board words that resonate with you. Be authentic (see above: everybody “moves fast” and “only works with world class people”). Put anything up there. Leave it.

Get together again a day or two later for another two hours, and bunch the words. Get it down to seven or fewer words that resonate with you all. That’s it — a fast, light-weight process. It’ll get you started. You can iterate.

Or you can hire somebody for an offsite and spend forever writing a long and complicated statement. Up to you. I’d go for the light-weight version myself.

Why is culture so important to a business? Here is a simple way to frame it. The stronger the culture, the less corporate process a company needs. When the culture is strong, you can trust everyone to do the right thing. People can be independent and autonomous.

Brian Chesky Co-founder, CEO of AirBnB (who is, by the way, doing his job of running a pretty giant company, for the first time I believe).

Find Your Number 2.

If there’s one thing that’s going to help you in all this, it’s finding your number 2. Because:

  • you will have a sounding board for difficult decisions
  • you will have more bandwidth at the top of your org. Surprisingly, you will have more than 2x the bandwidth. A good number 2 makes your own processes much faster, in addition to adding their own.
  • you will be able to deal with a wider range of issues as the number 2 will have skills that you don’t (or you have not hired the right number 2).

Important things about the number 2:

  • they need to overlap with you a lot in terms of skills and values
  • but they need to complement the areas where you are naturally weak.

Example: I suck at, and don’t enjoy, deal-making and negotiation. At the VP level, that’s part of the deal. I almost always ended up with senior people reporting to me who were great at that.

Bear in mind: the number 2 reports to you. It’s not “two in a box”. Why? Because you’re in charge. Ideally the number 2 has more experience than you in some areas and less in others, and wants, eventually to have your job when you, and they, have learned stuff, and are both moving up.

But where do I find one? You find them while you’re doing the rest of the scaling. Keep your eyes out when seeing who’s in the team who might develop, and keep this role in mind when hiring.

If you have it in mind, you’ll find the right person.

“Help!! I Need to Hire A Ton of Really Great People!!!”

Yes, you do.

Here’s the big secret about hiring: it’s a numbers game. The more people you see, the more great people you will hire. That’s it.

And it takes a lot of time, most of which seems like a complete waste — ploughing through resumes, going to meetups, listening to yet another dud interview. Ugh. There are a few things you can do to be efficient (don’t spend time on candidates that won’t work out, make sure your sourcing recruiter — if you’re using one — is super-focussed, make sure everybody in every network you have knows that you are hiring), but really, it just takes time.

That’s the game. You need to be spending at least 30% of your time hiring if you’re scaling an organization fast. At least. (Elad Gil, of Google and Twitter, makes the same points, with more detail).

See also “working hard”. And there are enjoyments to the process: the thrill of finding and closing that Great Person; the fun of meeting interesting people. Get your fun where you can.

“But There Is So Much Competition for the Great People!!”

Yes, there is. But there’s only one you.

What makes your company/team special? (hint: it’s not that you move fast, or only hire the very best. So does everybody else). Who are your people? What is special about what you’re building (hint: yes, it changes the world. So do all the other 5,000 startups in SF right now. “changing the world” is not special. changing a particular piece of it that is super-important to you — special).

The clearer you are about what you really value in your people and what you are building, the better — the more you will be able to express that in your search communication, in interviews and in the final closing.

When a person matches the essence of what you’re doing, when they feel that you and your people match them, they’ll turn down the big bucks from Google. At least maybe. And if they only wanted the big bucks, well, that would have been a problem down the line.

So in your ads, your meetups, your interview process, communicate what it is about you, your team and your mission that really resonates. And you’ll find the resonance in other people.

This is a nice, short summary making something of the same point.

“We Need to Get Some, Like, Managers, Or Something”

Well, if you’re ending up with more than, say, ten engineers or product people, yes, somebody is going to have to manage them. That would be a manager.

Here’s a little secret about managing an expanding group of dedicated people: it’s not that hard, and a little goodness goes a long way (see also “Doing It For The First Time”).

So look around: do you have engineers or product managers who take responsibility and get shit done? OK, those look like managers. Ask them if they want to take a shot at it. Yes? OK, promote them. Here’s what they need to know:

  • how to communicate clear goals and have some way of knowing when those are achieved
  • how to help people when they get stuck
  • how to listen to people (really listen)
  • the basics of running a meeting (start on time, have the minimal number of people, have an agenda, stick to it)
  • the basics of time management (but if they get shit done and take responsibility already, then they probably already have this baked in)

That’ll get you started, and will save you a ton of time trying to hire a new boatload of professional managers (see also: “Doing it for the first time” — dangers of).

A couple of good resources to get you started thinking about engineering management. And software lead weekly is always good (and, truth in advertising, is where I get a bunch of good sources on first level management as it is really occuring the world).

Now. You probably will want to hire some managers from outside. Be careful. A successful manager in one environment will not always match yours. So check what you need: tech ability? Project management? Ability to deal with uncertainty? What is it that adds to what you have already. Don’t be dazzled by resumes.

A word about “Culture Fit”

“Culture fit” doesn’t mean that the person you are thinking about hiring looks like you, sounds like you, or acts like you. It doesn’t even mean you like them that much. In fact, if you don’t end up hiring some people that are quite different from you, you’ll end up without the creative cultural friction that’s necessary for great results.

“Culture Fit” means they share your core values. The core. Everything else is up for grabs.

True story: I once hired a woman from Georgia to run a big part of our org. She was smiling, open, engaging and unfailingly polite — more or less many of the things I was not at age 30. But, man, she could get shit done, and loved the products we were building. Her intensity (which I value highly) was there, it just looked (very) different to mine. Great fit, and a huge success.

“Managers Suck All the Life Out of Engineers”

Engineers can be wary of managers, in spite of being very clear about what they want.

I vividly remember being called a “suit” when I showed up to take over the engineering group of a startup down on Townsend Street. I was wearing Levis 501s, a tee-shirt and Converse AllStars. So this goes deep. For some reason, management gets a bad rap. I don’t know why.

OK, I do know why. Creativity vs Control is the reason.

The goal of engineering and product managers is to make the group successful. That’s it. There is a perception that managers “control” engineers and creative people. Here’s the thing: building technology is a creative process — nobody is in control. To do a great job as a manager, you channel the creative process so it produces something great more or less on time for about the right budget.

Remember that, and repeat it to the group and to yourself a few hundred times a day and things will go better.

“I am in service to the creative process”. Try it. You will spend more time making sure that the team has what it needs, and less time wondering if you are “in charge” or “in control”.

Make sure the engineers have a quiet place to work, a minimum number of meetings, really fast machines, are paid what they are worth and have time for an occasional rant, and you’ll be way ahead of the game. Double points if they are clear what they are working on and why.

By the way: sometimes making firm, timely decisions is a thing that teams need. “Serving the creative process” means making sure it comes out right, not being steamrolled by it.

Yes, there are some subtleties here.

“Who Defines the Product??”

So you’re moving from a world where defining the product was pretty easy, or at least well-defined. Maybe it was being done by one or two people who everybody knew, and now it’s being done by a bunch of people who have their own ideas about what it should be and how it should work. Scary.

Who defines the product? OK, you need a few things:

  • a clear, final decision-maker. Probably the Product Manager.
  • the understanding that this is a creative process
  • the understanding that the PM does not fully control the process. They are there to provide a service, which is clear, well-thought-out, timely decisions and a clear, well-thought-out project context (time and budget). This is not to belittle that job: doing those things well is creative, hard and takes terrific skill. Getting the role clear makes it easier.

Don’t conflate decision-making with design. And definitely don’t conflate decision-making with the protean, murky and wonderful business that is technical inspiration. You want the engineers to come up with wild wonderful stuff, totally out of the blue. That’s where (some of) the magic lies.

So. “Who defines the product?”. Official answer: the PM. They make the decisions. Reality: it’s a collaborative creative process.

There are many great resources about Product Management.

Process In General. Yes, You Need It.

So “process” is often seen as The Official End Of The World. That wonderful free-wheeling time when everybody was creative and stuff just happened is now dead and controlled by the evil hand of rules and regulations.

And, you know, that can happen. When groups start forming who’s only purpose is to define process, I kinda draw a line (probably a weakness on my part).

Good process can be elegant, lean and of great value.

Thing one, first thing, do this: write stuff down. Please. There are too many touchpoints now for everybody to understand the implications of a quick great idea you and Sam had at lunch. Choose a project coordination tool (Basecamp, Slack, whatever) and write stuff down. The minimum “stuff” comprises the decisions you make (this goes waaaaayyy the hell back to “The Mythical Man Month”).

There are reasons:

  • writing stuff down helps you understand it more clearly
  • writing stuff down lets other teams adjust their work accordingly
  • writing stuff down gets other eyes on your decisions and will make them better over time

Thing two: be clear who makes decisions and when. Good decisions, made at the right time, are a great service to everybody.

Thing three: the earlier you get clear the difference between the engineering career path and the management career path, the easier your life will be. Engineering skills and management skills are both valuable, as are engineering and management people. They have different motivations, but both want to be as successful as they can be. Give them a structure they can use to measure success in their career.

Thing four: get good at meetings. The uber-process, the process on which all other processes depend.

Is the meeting:

  • a decision meeting?
  • a status and discussion meeting?
  • a brainstorming meeting?

If it’s a decision meeting, get a decision. if it’s status and update, time-box it, and leave with specific actions. if it’s a brainstorming meeting, time-box it, leave with a ton of new ideas.

All of this is hammered into the ground in a very thorough Google Ventures presentation. It takes an hour, and doesn’t have many laughs, but you’ll be the better for watching it.

I’m sure I’m understating the amount of process you need. But I don’t think I’m understating that it can be light-weight, elegant and designed to do the job that is needed and no more. Not to mention that the tools now available are insanely good.

Get good at this.

Over Communicate

Do weekly emails to everybody, have weekly all-hands if you can, stick stuff on the wall, use collaboration tools: do whatever to over communicate what’s happening, both good and bad.

There is a lot, really a lot, happening when you are scaling this fast, and as humans we don’t like uncertainty. So the more you can keep your team informed as to where you are in the process, what changes you are making and why, the less uncertainty there will be, and the more happiness.


Work Hard. Life is to be lived intensely. This is an intense moment. It could be a great moment. Dig in.


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