Follow your weird

To really win, you have to seem strange to your true peers, not just the world at large.

Photo by Elias Castillo

Look, I have to say it: You’re weird. Even if I don’t know you, I’m confident: Somewhere, maybe lurking deep inside, something about you is just not right. I don’t know what, specifically. For all I know, you might be one of those weirdos whose particular strangeness is just how authentically normal you are. *shudder*.

This might be insulting to you, calling you weird. It happens a lot: I think I’m complimenting someone and they get all huffy. Conversely, people are often afraid I’ll be hurt when they shyly let me know that I, ah, don’t really fit. Don’t worry; you’d need to know me a lot better to successfully offend me.

Society is not a huge fan of weirdness — I mean, the definition is pretty much, “does not fit into society” — and it trains you away from it. We’re social animals, so you probably do what you can to conceal, or at least downplay, anything different. It makes sense. It’s a basic survival mechanism.

I know I do it. I can’t hide everything — some stuff just can’t be covered up — but I can usually skate through a conversation or two before people back up a step and give me that funny, sometimes frightened, look. Being on the west coast helps; I’m a little less weird here than I was in the south. It probably also helps that I cut my mohawk, and the spiked leather jacket and knee high boots stay in the closet now.

I’ve written a bit about my struggles to balance authenticity and fitting in. I think it’s important to call out it out, because those who experience this struggle rarely have the luxury of admitting it. I’m lucky enough in multiple ways that I can be up front about it now. But resolving this conflict matters for more than psychological reasons. Our own goals usually require that we learn to embrace our weird. Not just grab on to it, actually, but really live in it. Inhabit it.

That weirdness is how we win.

This is easiest to show in investing. We have a natural tendency to do what is proven to work, but that is only assured of getting “market” — in other words, mediocre — returns. If you study the best investors, they’re all doing something that seems weird. Or at least, it did when they started. The first people who paid to string fiber from NYC to Chicago to make trades a couple milliseconds faster were considered pretty weird, but they knew the truth: Normal behavior gets normal returns, anything more requires true weirdness. (Well, or fraud. There’s always that if you’re afraid to stand out.)

It’s the same way in life. You can’t say you want something different, you want to be special, but then follow the same path as everyone else. “I’ll embrace what makes me special just as soon as I get financial security via a well-trodden path to success.” Oh yeah. We definitely believe that.

There’s a nice sleight of hand you can do, where you can say you’re doing something different, but really you’re a rare form of normal. The first few doctors and nurses were really weird. Those who recommended you wash hands before surgery were literally laughed at, considered dangerous crackpots1. But now? Most people become a doctor in pretty much the same way. Being a doctor is normal now, even if it’s not common. That’s probably good.

But what if your job is innovation? What if you’re whole story revolves around being different? Can you still follow a common path?

Because that’s what too many entrepreneurs today are doing: Trying to succeed at something different, by doing what everyone else is doing.

I mean. Not literally everyone else. But close enough.

It starts out innocently enough. There aren’t many people starting tech companies at first, and boy howdy are they weird. Someone makes a ton of money, all their weirdness gets written up — “hah hah, see how he has no sense of humanity but is somehow still a billionaire?” — and now we’ve got something to compare to. Hmm. Well. We can’t consistently duplicate Jobs, Gates, Packard. But if we tell enough stories enough times, we find some kind of average path through them. Ah! Enlightenment!

Now that we know what “most” people do, we can try it too. I mean, we have no idea if the stories about those people have anything to do with why they succeeded, but why let that get in our way? Conveniently, every time it works we’ll loudly claim success, but silently skip publishing any failures. Just ask Jim Collins: He got rich by cherry-picking data in Good to Great to “prove” there was a common path to business success. It turned out to have as much predictive value as an astrological reading, and is just business garbage dressed up in intellectual rigor, but that doesn’t seem to have hurt him.

The business world keeps buying his books. They need to believe there’s a common path that anyone can travel to victory. Otherwise, what would they sell? What would they buy?

Obviously this doesn’t work. There is no standard playbook to winning an arms race. Once there’s even a sniff of one, people copy it until it doesn’t work any more. This is pretty much the definition of the efficient market hypothesis: There’s no standard way to get above-average results. Once Warren Buffet got sufficiently rich as a value investor, so many people adopted the strategy that, well, it’s hard to make money that way. Not impossible, but nowhere near as easy as it was fifty years ago.

Of course, you can go too far in being weird. There has to be something in your business, in your strategy, that makes you different enough that you just might win. But adding a lot of other strangeness for no good reason worsens already long odds. The fact that Steve Jobs did so well even though he was a raging asshole, even to his best friends, made his success just that much less likely. Most people are a bit more like Gates and Bezos: Utterly ruthless in business, and caring not a whit for the downsides of their success, but perfectly capable of coming off as a decent person whenever required.

I’m rarely accused of being a world-class jerk, but I don’t pass the smell test as normal for very long. Jim Collins might say maybe if I were more pathological I would have succeeded more. With Jobs and Musk as examples, it seems reasonable, right? In truth, it’s just as reasonable that I would have done better by dropping out of Reed College, like Jobs did, rather than foolishly graduating from it. Think it’s too late to retroactively quit early?

Yes, you have to learn to love your weird, but it shouldn’t be arbitrary. You can’t realistically say that you’re going to rock it in business because you’re addicted to collecting gum wrappers from the 50s. I agree that that’s weird, but is it usefully so? Being a jerk is weird, and bad, but it’s not helpfully so. And really, dropping out of college isn’t that weird for someone in Jobs’s financial position at the time. It’s only if you have a bunch of money that it seems so.

I recommend you take the time, think deeply on what opinions you hold that no one else seems to, what beliefs you have that constantly surprise you by their lack in others. What do you find easy that others find impossible? What’s natural to you, but somewhere between confounding and an abomination to those who notice you doing it?

Those things aren’t all good. And in many cases, you’ll need to spend your entire professional life managing their downsides, like I have. But somewhere in that list is what sets you apart, what gives you the opportunity to truly stand out. They’re the ground you need to build your future on.

Unless you just want to be normal. In that case, I don’t think I can help you.

  1. This is an amazing example of sexism. The doctor’s wards had three times the fatality rates of the midwife wards, but of course, they were doing nothing wrong at all.

Great advisors reveal your truth, not theirs

Giving answers is easy, and usually worthless

Photo by Blake Cheek

Being an advisor to other founders is a contradictory affair: Be helpful, but do not give advice. That is, I want to help you do your best work, but I don’t think I can or should do it by telling you what to do or think.

I obviously think I have value to add or I would not sign up to help. Well, maybe it’s not obvious; our industry is rife with advisors who attach their names and little else to projects. It’s true I’m motivated to join partly by the possible long-term reward, but mostly I’m helping because I enjoy it and am learning a lot.

While running Puppet, I was constantly confronted with a classic leadership struggle: How do I simultaneously help people improve their own answers, yet get them to do what I want? There are many who will say this is a false struggle, that I could have avoided it by focusing on empowering people instead of trying to get them to do what I wanted. Pfft. The literal definition of leadership is providing direction and getting people there, and that’s doubly so for a fast-growing startup where alignment is critical to execution. I spent a decade slowly, incrementally, getting better at this, but felt my incompetence as keenly at the end as I did at the beginning.1

Advising companies allows me to practice the empowerment-half of this skill without the other complications. Unlike when I was a CEO, I know I should not be setting direction or making decisions. My job is not to provide answers, but to help people do their own best work.

My only explicit training for this was when I was an organic chemistry lab tech in in college. My primary task was repeating questions back to the students: “I don’t know, which layer do you keep?”2 When I started dating my now-wife in college, she told me her friends were bitter that I would not give them answers. I knew my job. I was there to help them get an education, which required they did the work on their own. This has also been helpful experience for being a parent: “I don’t know, what is 12 times 9?”

Advising CEOs has similar constraints, but it’s a lot more open-ended, and has no answer sheet. In the lab, there was one right answer, it was always the same, and you could reason it out with the information at hand. Labs were also usually a day of work, maybe three days, and mistakes were pretty cheap, in the grand scheme of things. I don’t expect one of those students to track me down later in life and lay at my feet all of their struggles or successes. Most importantly, we were studying an objective space that I did actually know more about. When push came to shove, I knew the answers, and I could reason out anything that wasn’t obvious.

Helping CEOs is considerably harder. I’m rarely asked about questions that have a single right answer. No competent CEO would bother getting advice on an easy question, or one whose answer wasn’t important. Wrap into this the fact that I can’t possibly know the company as well as the person asking me the question.3 It’s inconceivable that I would often have answers available that the expert in the seat doesn’t.

That simplifies the challenge: Prod the questioner into getting to their own answer, no matter how much they complain. And they do sometimes get upset: I had a CEO exasperatedly demand what I would do, after a long session of forcing him to work through what he cared about, what he saw as the right answer. When I relented — only after he had already done all the hard work — he could see how thin and useless my answer was. By the time he’d decided what to do, he saw that what he learned from the process was at least as important as the answer, and my just providing a solution could never give that.

There is still some risk. I’m by no means a master of this technique. I know I have at times presented people’s options in stark ways, which sometimes felt like no choice at all. My own predilections, such as toward a consumer-style sales model, are hard to separate from any guidance I might provide. It’s honestly just hard to know sometimes whether you’re successfully getting someone to express their own implicit belief or leading them to agree with one of yours.

It’s a skill I expect to spend the rest of my life trying to master. But it’s worth doing, and I’m enjoying the learning process.

Helping CEOs instead of running my own company provides a kind of repeatable laboratory environment. I get to learn at the same time, though, because it’s much harder than being a lab tech.

It’s not enough to just parrot questions back. I spend my time listening closely and drawing out more information, then replaying back what I heard. Listening is a woefully underrated skill. I’ve been loving the opportunity to practice really hearing what people are saying, and trying to differentiate between the words they use, the meaning behind them, and their intent in saying it at all.

As you look for advisors, be sure you demand the same discipline from them. Don’t accept answers. They should hear you, understand your dilemma, and be able able to point out where you haven’t thought completely, or clearly.

A great advisor should provide light, not direction.

  1. If this whole definition of leadership annoys or offends you, I’d ask how you differentiate between leadership and management, and also how you expect a company to align around a direction without someone picking the direction.
  2. Nearly every experiment in organic chemistry involves using liquids to separate chemicals, where part of the solution ends up in an aqueous (watery) layer, and the other ends up in another layer, like separated oil and vinegar in salad dressing. One of those layers is now waste, and the other one has the chemical you’re working on. Don’t throw away the wrong one!
  3. This is another big difference from when I was the leader; I knew Puppet itself better than anyone, even if I could not know your specific area as well.

Hold on to your why

Founders need to retain their own mission while they build out the company’s.

Photo by Sharon McCutcheon

Managing a high-growth company is the hardest thing I’ve ever done. One big reason is that I only received problems that no one else could figure out. Some were organizational problems that should naturally route to the CEO, but a lot were functional issues that I was no more capable of solving than anyone else.

I eventually discerned a repeated pattern in solving these problems. At first I would just get a few issues. I’d muddle through — do a bit of research, ask for help, and sort things out. As we grew, more and more of my time would be spent on this one kind of problem. I’d become better and better at handling it, and just about the time I’d start feeling like I knew what I was doing, I’d realize, “Oh: There are people out there who specialize in this”. I could just hire someone to do it full time, and they’d be better at it than I ever would. Duh.

I’d then spend three months, or six, or twelve, hiring for the role, and bam, suddenly my time is freed up and I’ve got an actual expert in charge. Well, kind of. At this point I’m a self-taught semi-expert who does not buy into the orthodoxy of the role, and we’ve got a year of my weird solutions, so there’s a lot of friction as we sort out just how to add this new skill set to a growing org. But the point is, my time spent on this problem drops precipitously, and I no longer have much opportunity to put my new-found skills into practice.

Usually just in time for something new to come into focus.

This pattern — gain just enough expertise to hire someone — played out again and again, for me and for other founders I’ve talked to.

In some ways it’s thrilling. You get experience with all of the key areas at the company, and you’re always learning something new.

In other ways, though, it is soul-crushing. Over the eight years I managed Puppet while in fast hiring mode, I rarely got to spend time doing anything I was good at. Humans have a psychological need to feel competent, to feel like they are in control and know what’s going on. I don’t need this all the time, but please, just a little? Sometimes? Nope. Pretty much the second I started to feel like I understood something, I had to hire for it, and my problem changed from doing to managing.

After years of this, I knew just enough about everything to suck at it, but not enough to actually be useful to anyone.

Only as my tenure as CEO came to a close did I begin to see what I uniquely added to the organization. I began being comfortable not delegating certain problems, and felt justified in spending hours on something as an individual contributor, rather than seeking leverage in everything I did.

Only once this happened did I start to feel comfortable as a CEO. I wasn’t just routing problems, I was actually solving some of them. I was not spending 100% of my time in areas I was incompetent; just most of it.

I know the advice as well as you: Great leaders delegate, they empower. If you’re doing the work yourself, you’re not a real leader.

Bullshit.

Yes, building and running a team absolutely requires that you empower the team. But that doesn’t mean you don’t get to do anything yourself, that you hand everything off and have nothing left.

Just like everyone else, you, too, need a reason to show up, to stay engaged. You have to hold on to your own why.

If you don’t remember why you, personally, are in the job, then you’ll look up in a few years and realize it’s not there any more. You’ve moved too far from what gets you up in the morning, and suddenly you can’t do it. Or worse, the company has developed but you haven’t. You’re no better at the thing you want to master than you were when you started, because you haven’t been spending time on the problems you care most about.

Some of this is that you need a place of safety. I am a highly fireable person, and raising venture capital made for downright tenuous tenure. The less confident I was about my own strengths, my own value, the less safe I felt. And humans need to feel safe to do great work.

More than that, though, I needed a platform for learning. I was pursuing mastery, but of what, exactly? Of not mastering things?

I know other leaders really are master delegators, hirers, organizers, etc. But that was never going to be me.

I had to peel things back, really understand why I was there, what I cared about, what I wanted to be the best in the world at. And, really, what I was good enough at that I ended up in this place, running this company. Then, as the problems rolled by, I could be sure to push that forward just a little bit, even if my focus was on the organization’s needs, not my own.

The times I lost this sense of why I was there and what I was getting better at were some of my most depressing days. But the days where I could connect what I felt good at, what I spent my time on, and what the company needed from me were the best days.

I don’t think that’s any different for me, or for other founders, than it is for anyone else.

But all the discussions of leadership I hear leave this bit out: You’re a human, too. You have to provide the why for the whole organization, but every individual deserves to be able to translate that into what they do every day. Even you.

Putting OKRs Into Practice

The true story of trying to put Google’s planning system into use

When Google was less than a year old, they began using a planning system presented by legendary venture capitalist John Doerr of Kleiner Perkins. When I went to put it into practice at Puppet in the early days of growing the team, things were not as easy as they appeared. Success involved creation of a complete solution, not just a description of the documents you need to create.

When I went to try to use the system as described by Doerr, I had multiple questions it didn’t answer. Just to start with, when and how do you make and update these OKRs? It’s great to say you should have this recording of your goals, but I could easily come up with multiple conflicting mechanisms for developing it, none of which are obviously better:

  • The CEO could develop them independently and deliver them to the team
  • The executive team could develop them collaboratively
  • They could be sourced from the front-line team

None of these is obviously right or wrong, and of course, neither are they sufficient explanations for how to do it. Do you do it one sitting? Multiple revisions? How long should you spend on it? How often should you update them? Can you change them mid-stream if your situation obviously changes? There’s a lot left to the reader. You can say it doesn’t matter, but of course, it does, and even if you’re right, you still have to pick one. Why go through the effort of describing the output but skip the whole process you used to create and maintain it?

Here’s how we did it.

Startup Days

Starting by reading John Doerr’s original presentation, even though it’s relatively thin. In summary, you should have three to five top-level objectives, and each of these should have a couple of key results associated with it. Together these constitute a company’s Objectives and Key Results, or “OKRs”. These should then cascade down to the rest of your team, so that each team and person has OKRs. This is a useful high-level tool for communication and focus, even in small teams. (Note that I’ll use ‘goals’ and ‘objectives’ interchangeably here; far more people use the shorter term in practice, and we treated them equivalently.)

At Puppet, we spoke of an operational rhythm, which is essentially the set of repetitious tasks we run and the cadence we execute them on to keep the business working. But the OKR system as presented includes no operational rhythm, no indication that people are involved in creating these goals or that doing so takes any time. So we invented our own rhythm:

  • As early as possible each period, the management team meets to decide the company OKRs. This started out as a 45-minute meeting that just recorded the goals that were in my head, but evolved over years into a two-day offsite where the leadership team first acquired a shared understanding of where the business was and what we needed to do, then built the goals from there. In retrospect we should have put in these longer days earlier; your team should frequently think deeply about what you should be working on, rather than just running all the time.
  • The rest of the company has some time to build its OKRs from the top-level goals. Initially this was a couple of days, but it eventually morphed into a couple of weeks.
  • These cascaded goals are then used to modify the company OKRs if needed. (In other words, we supported a merged top-down and bottom-up planning model.) This is when management would learn if our view of reality was materially different from that of the people at the front line.
  • At the end of every period, the management team records how we did against our goals. Again, this began as just writing down the score, but grew to become a more complete retrospective run by a project manager. This meeting it at most a couple of hours long, and just includes the leadership team.

When we began this process, we wanted short-term goals, so we ran this cadence eight times a year; thus, we called our planning periods “octaves.” As we matured and could think and execute in a more long-term fashion, we reduced this to quarterly.

I think this system is sufficient for most companies of 15 to 250 people. Some companies might grow out of this at relatively few people, whereas others might scale very well with it. I expect most people could scale this system successfully by gradually increasing the amount of time spent on each session, with more time in deep discussion, and also by assigning a project manager to run it. I ran the whole process until we were probably 250 people, which was a mistake that took too much of my time, resulted in too centralized of an organization, and limited our effectiveness because I suck at project management.

Note that these are pointedly not plans; that is, they are not step by step instructions for how to achieve a goal. We’re declaring what we want done, but not how we expect to do it. This is both a blessing and a curse. On the one hand, it provides a lot of freedom for people at the front line to figure out the right way of accomplishing something, but it also leaves a gaping hole in your organization. At some point, someone has to actually do the work, but where in your operational rhythm does a team translate goals into a plan for accomplishing them? Do you make that time? We didn’t until far too late, and it mattered.

Scaling

As we scaled the company and this system, we found a few critical gaps.

The biggest one is obvious enough that I cringe now just thinking about it. You would never try to build a product without being clear on who would do the work and, of course, you shouldn’t try to accomplish your company’s goals without assigning each objective and key result to an individual, yet our initial version (and the one presented by Doerr) had nothing to say on people. At some point we added the requirement that every objective had a name assigned to it, which was a huge change for us – and a really positive one.

The lack of accountability for each goal was exacerbated by the fact that we didn’t have any mechanism for in-quarter check-ins on the goals. We’d frequently only find out at the end of a quarter that a goal was going to be missed, when it was far too late to do anything about it. So we built a weekly operations review (“ops review”) where we reviewed progress against the goals. This meeting is a predictive exercise, not a status statement. Goals are green if you expect to accomplish them on time, even if you’re still two months away from the deadline. We mostly focus just on the areas we don’t expect to hit, which allows us to invest early in correcting our execution or changing our expectations.

It’s worth reiterating, because this was so hard to get people to understand: The goal of the ops review was not to describe the status of each goal; it was to build a shared understanding of whether we were likely to achieve our goals and then build an action plan to resolve the predicted misses. The majority of people entered that meeting with a belief that they needed to justify their paycheck, and it took a lot of education to get them to understand the real purpose.

This addition to our rhythm was pretty awesome. In one move, it basically eliminated the firefighting that had driven so much of our execution. We still had fires periodically, but they were actual surprises, not just sudden surfacing of old information, or realizing at the end of the quarter that a goal never had an owner.

The downside of the ops review is that it’s expensive (it necessarily includes a lot of top people at the company) and it takes a lot of work to make this kind of meeting worthwhile every week. I got the idea for this meeting from the excellent American Icon, about how Alan Mulally turned around Ford. A long, weekly operations review with his senior team was one of his key tactics. My team often complained that weekly was too frequent, but if a company as big as Ford was responding weekly to the conditions on the ground, shouldn’t a small startup be at least that responsive?

Around this time, we integrated the budgeting process into the planning process. It’s important to recognize they’re different — you should build the plan you want then find a way to budget for it, rather than building a budget for your departments then letting them decide how to spend it. It’s important that your should be good at both, though, and it was around this stage we started to develop the budgeting skill and learning how to integrate it into planning. That was painful, to put it mildly.

As we scaled, the company goals tended to get expressed in terms of departmental targets within sales, marketing, engineering, etc. When we were small, this seemed like a feature because it had natural lines of ownership, but as we grew it became clear it was a critical flaw. It’s important to translate plans to people and teams, but this was dysfunctional. It discouraged people from building goals that relied on other teams, and thus encouraged silos in the company. Talk about a failure mode. When we added names to each objective, we rebuilt the whole process to be structured from the top down around company goals rather than team goals, which allowed us to crack this departmental view and force shared goals and collaborative execution.

We also eventually added a layer of OKRs above our annual goals, giving us a roughly three year time horizon. These became crucial in sharing and deciding what the priorities were for a given year.

What might come next?

The above roughly describes the system as it stood when I stepped down from Puppet in 2016. It was obvious at the time that we were in need of another step-change in capability in our planning system, but the new CEO took responsibility for driving that. By the time I left, we could see many opportunities to improve what we were doing.

The big one is that we needed to push all the local knowledge about this process into code. We were using multiple different formats and tools, because different meetings require different interactions, and it was too difficult for most people to track what was happening, where, and why. For instance, our source of truth for the OKRs themselves tended to reside in Trello, but it’s a poor fit for storing updates and presenting the predictions of whether a goal would land. I couldn’t imagine trying to run a report on quantitive goals based on Trello data. Thus, we ended up storing the weekly updates in spreadsheets, which are exactly as powerful and readable as shell scripts. It meant we couldn’t trust most people to update the data, because the document was so complicated. I would have loved a single source of truth that anyone could use. In addition, I wanted to have an app automatically pull any data from original sources so I didn’t have team members doing manual work that could be automated (I mean, duh, Puppet is an automation company).

I also wanted a significantly better retrospective process that truly helped us improve the business by laying bare how our wonderfully laid plans went wrong. We were good at the work of looking back and being transparent about where we were, but there was a lot of room for improving how we tie that work to how we operate.

Lastly, I hate that our goals were built around quarters. I think having a cadence for building and validating plans is critical, but it’s silly that this cadence got translated into the timelines for the goals themselves. It often implied that each of our goals would take exactly a single planning cycle. Some obviously do — we have quarterly sales targets that we need to hit during exactly a quarter — but many of our top-level objectives were shoehorned into a quarterly system. I’d much prefer a Kanban-style on-demand planning system that would allow us to have a high-fidelity plan for what we’re working on now, and a quality backlog for what we’ll do as goals complete.

Conclusion

I’m not convinced it matters much what planning and execution system you use, but I’m utterly convinced you should have one. In the end, it’s merely a team-wide mechanism for developing, communicating, and tracking what you’re trying to achieve. It’s obviously important to have goals. I think most of us would agree you should, in some way, share those goals with the team so everyone is working toward the same ends. And, of course, your goals tomorrow should probably be somehow related to your goals today. (This is surprisingly hard.)

If you don’t have one yet, you could do worse than building an operational rhythm from what we built at Puppet. You’ll have to work through a lot of initial discomfort as you translate vague words into technical terms whose meaning is widely agreed upon around your team. But it’ll be worth it.