Tag Archives: team building

Founder Intuition vs. Team Expertise vs. Customer Expertise

When founders of startups start to hire employees to work on various parts of the business, it tends to be uneasy for both the founder and the employee early on. The founder may have done that job in some capacity before they hired for it, but they are not an expert. The incoming employee may bring more expertise, but they don’t know the business yet. The founder is going to have a lot of opinions as is the employee, and they won’t necessarily match. In this essay, I’ll talk about how to think about balancing founder intuition vs. team expertise, and how that changes over time. I find that this same balance is true for customers vs. founders when they start businesses too, so we’ll cover that as well.

Generally, the biggest mistake founders can make when starting to hire a team is defer too many decisions too quickly to new employees. This is most painful with new executives, but can also be damaging when hiring new individual contributors. Founders frequently convince themselves that this new person they hired is an expert on this topic, and they should defer to them. The opposite actually tends to be true. The founders are experts on the business. And incoming employees should defer to them until they are confident they have become more of an expert on a certain aspect of the business.

The opposite mistake tends to happen later on as the business grows. The founders have now staffed the company with a lot of great talent who have had time to learn the business, have impact, build processes, know customers really well, etc. Meanwhile, the founders are scaling a bigger business and getting further away from the details. Founder intuition becomes less reliable because the founder(s)’ advantage of having spent more time on the problem goes away. Their thoughts become perhaps dated. And they won’t really know it. This degradation of founder intuition also happens at different times for different parts of the business.

Great founders start to back away from relying on founder intuition when they see the expertise developing on the team, or are proven wrong in a meaningful way by the team that makes them start to question their often blind faith in their own judgment. Moving forward, founders have to calibrate how their intuition stacks up against team expertise on every topic of the business to know how much to intervene vs. let the team drive. Think of this as a simple graph.

It’s incredibly hard to accurately graph where the founders and team are on this graphic for every topic within the company, and when they cross. Normally, founders tend to navigate this based on factors like personal interest, what areas of the company they perceive to be doing well or not, etc. Having worked with lots of founders myself as a leader, advisor, investor, or board member, I default to founders needing to operate differently at different stages. On a bunch of different axes, I have mapped how I think companies optimally behave as they grow (changes in italics).

Phase 1: Starting Phase 2: Scaling Phase 3: Expanding
Founder makes decisions Founder starts to delegate decisions Founder empowers team completely
Speed > Precision Speed with some precision Precision > Speed
Generalist > Specialist Specialist = Generalist Specialist > Generalist
Done > Perfect Done > Perfect Done Perfect Trade Off
Focus > Breadth Focus > Breadth Breadth Focus Tradeoff
Execution > Strategy Execution > Strategy Strategy = Execution
Hungry > Seasoned Hungry > Seasoned Seasoned > Hungry
Cheap > Robust Cheap Robust Trade Off Robust > Cheap
Teamwork > Process Some process Process First
Doers > Managers Doers with some doer-managers Managers + Specialists

Obviously, this table can be a bit crude, and understanding when the company is shifting between phases is not always apparent to everyone inside the company. But it provides a default guide on when to delegate and empower teams as a company grows. I find that just asking the question of what phase the company is in builds good awareness on how one might want to be operating at the moment.

If you are a startup employee or leader, you have to respect founder intuition greatly. The company would not have gotten to the point you could have even been hired had that intuition not served the company well. But when you’ve really spent the time to understand the business and you or your team can start to have better judgment than the founder, it’s important to signal that confidence and get alignment on the operating model shifting. It will not be an easy conversation, but worthwhile to have.

What can you gain from such a conversation? First, you make the above graph visible to the founder in a way they may not be aware. Second, you can calibrate where each of you think you are on this graph. If the founder believes their intuition still serves the business better on a topic than the expertise you have built, then you can have a conversation about what would signal those two lines crossing to change how decisions are made in that area? Keep in mind, in some cases, that answer may be that there will never be a signal that changes how much control the founder wants to exert in an area. Companies are not democracies, and founders have the right to run the company any way they want. If they want to drive decisions on what tech stack the company uses or which segments are interesting, they will. If you don’t like it, you should join another company. But most founders want to do what is best for the company, and giving them the signal on where it’s valuable for them to lean in vs. that potentially being unhelpful is worth figuring out.

On the flip side, if the founder is putting decisions on you or your team where the founder would be better fit to make the calls themselves, tell them! There is no shame in admitting you’re not yet equipped to make the calls and empowering the founder to make more direct decisions for a while. This is not an admittance of incompetence. It’s driving clarity on decision-making rights that are optimal for the business. If you’re still asking the founder to make those same calls a year later though, expect them to think you aren’t developing the expertise you should be.

What is ironic about founders and employees facing this split between intuition from expertise is both have to do that same analysis with the company’s customers. When startups are small, most founders and employees tend to think the customer knows best. This may be experienced by changing the product based on customer feedback, allowing customers to experiment with different ways to use the product that help them become successful, etc. But as a company scales, it starts to see every way customers use a product, and what works best. For a marketplace like Airbnb, it might be seeing that hosts that provide toiletries get higher ratings, or for Eventbrite it might be seeing that emailing past attendees of an event a certain time before the next event maximizes their chances of buying another ticket. Then, the company’s job switches from observing what customers are doing and adopting them to teaching customers what best practices the company is aware of that will make them more successful.

So, in summary, founder intuition is extremely valuable, and new employees and leaders should learn to leverage that vs. ignore it because they’ve seen things before. But founder intuition does ebb over time in most areas as founders scale up the company, and of course, teams get a lot smarter as they spend time on deep company problems. This also happens with your customers over time. Having a dialog about where teams are in this journey is important to helping startups scale, clearing a path for teams to have maximum impact, and for leveraging founders’ scarce time in the areas that are most highly leveraged.

Currently listening to my 2022 playlist.

Transparent Optimism

When I started managing teams at Grubhub over a decade ago, I was pretty obsessed with high performance. I wanted my team to have very clear goals, remove any roadblocks they would face to being successful, and make a big impact on the success of the company. I was able to hire a strong team, and we got to work, 100xing the size of our customer base over four years. As part of this process, a lot of what I tried to do was reduce distractions for the team. Any time there was strategic misalignment or confusion at the top ranks of the company, I would hide that from the team so it didn’t affect their performance. In other words, I wouldn’t let confusion at the top level create confusion at their level.

As the team grew over time both in size and in scope, I started to see cracks in this strategy I didn’t immediately understand. The first symptom was people on my team saying that while they felt very supported by me and were growing in their skills and their career, they didn’t have much visibility in what other members of the team did or how their roles worked. So, I created a Friday meeting we called “Team Learn” where every week, one team member would deep dive on what they were working on so the rest of the team could learn more about it. Initially, these were topics like email marketing or Google Adwords, but we started expanding them to other topics the team wanted to learn about, like venture capital and emerging channels. This meeting was so successful other teams wanted to participate, so I eventually expanded the meeting to include other teams.

This didn’t solve the root problem though. As my team got more comfort or clarity in their feedback, I started to understand the root problem more. While I was shielding my team from any swirl related to top level strategic decisions or screw ups or whatever elsewhere in the company, I was not the only person they talked to at Grubhub. So, they would hear from peers about all of these other things going on I had deemed to be unimportant or distractions, and the fact that I didn’t ever mention them made it feel like I was hiding things from them. It made them feel as if they couldn’t handle that level of knowledge and weren’t being treated as senior as they should be. 

So I shifted my approach. I made a commitment to share what was going on, but also contextualize it so as not to create doubt or swirl in their minds about what was going on at the company. We were definitely winning, after all. I moved from extreme editorial filtering to complete transparency, followed by contextualizing how this will all work out and why we win. When we hire great employees, the push to focus them and not distract them, while good, can easily be used as an excuse to not share hard things, and that creates a belief that the team can’t handle unresolved conflict, work through confusion, or understand strategic fog or even help lift it, and creates the perception that you as a leader are hiding things. It’s like hiring a bunch of strong engineers, and then only feeding them tickets of what they need to code through Jira because if we actually got them involved in deciding the problem, “they couldn’t possibly understand the business!” It doesn’t make a lot of sense when you think about it.

At Eventbrite, I have come to call this style transparent optimism. I’m going to give you all the context, the good, the bad, and the ugly, and explain how I think we come out on top. I trust my team with being able to handle all of that context and ultimately help us work through some of the thornier issues together. This is a style of communication that will not work with all cultures. Company cultures have to decide where they exist on a spectrum of open vs. closed in their communication. If I tried to apply this style at Apple, for example, I would quickly be fired for sharing things they do not want shared. So I bias toward cultures that have a comfort with this level of transparency, which is not all companies! Many companies would not even let me write a blog like this while working there. At Eventbrite now, I host quarterly AMAs with the team, the CEO does them twice a month, and both the CTO and I wrote monthly internal blog posts on what is on our mind. 

Obviously, I am biased, and communication styles come with pros and cons. With transparent optimism, I create risks of more interpretations of what is happening, external leaks, and it just requires me to communicate a lot more. But ultimately, I think it creates a default trust and default respect with the team, and helps them contribute more to the success of the company.

Currently listening to Scurlage by µ-Ziq.

The Rise of Department Operations Roles, and How to Tackle Inefficiency

At every company, there are well defined roles you would expect to see. In software, they tend to be roles like engineering, product management, design, marketing, legal, finance, etc. But as companies scale, they tend to invest in more specialized roles over time. During that transition, operating in one of these roles can be confusing. One interesting trend emerging at many companies including Eventbrite is the creation of departmental operations roles. Oh, you’ve seen them: Marketing Operations, Sales Operations, Design Operations, Product Operations et al. My first instinct when I hear an “operations” title is “inefficiency.” Not that the operations person is inefficient, but that there is inefficiency at the company. It is okay to be inefficient at things at your company. At various times, it will make sense to be inefficient in tons of areas of the company. The danger is in accepting inefficiency for the long term. We should strive to eliminate inefficiency over time at companies, not embrace it. Thus, the goal of departmental operations teams can be somewhat paradoxical. By explicitly attempting to remove inefficiency, they are actually attempting to remove the need for their roles entirely. 

The Intercom Biz Ops team was the first to just come out and say it. This can create a remarkable conflict of interest though. By doing a good job, will I eliminate the need for my job? As a result of this conflict of interest, we have started to see people in these roles try to define them as long-term necessities in organization, which means employees are optimizing for themselves instead of the company. What is interesting about this trend is that this job security issue shouldn’t be a conflict of interest. The goal of every job inside an organization should be to eliminate the need for it so you can do more important things. This is a great way to get more responsibility and promotions. There would be no greater pride for me than feeling like I am no longer needed in my current role at Eventbrite, for example.

So, if you want to do a great job in a departmental operations role, how do you do that? Well, the real question is how do we solve inefficiencies at companies? It’s like solving any problem within your company. You use various tools. I have a very specific hierarchy I like to follow to solve these problems, and I wish more companies used it instead of defaulting to hiring people and creating roles. If you’re in a department operations role, you can consider this a playbook to helping the company be more successful.

#1 Software
Any problem or inefficiency we can solve with software is superior to other forms because it automates away the inefficiency in the future once it is built. Now, it may be the case that we cannot think of or do not have the resources to develop a software solution to the problem, permanently or temporarily, or that there is no software we can buy that helps. This is okay, even normal. Companies tend to under-invest in leveraging engineering to build solutions that help their companies become more efficient, largely because so many companies are engineering-constrained. But just like engineers have started to work more on business problems like growth or marketing, they will eventually start to work more on internal tooling that enables their and other teams.

#2 Process
My next goal would be to solve the problem or inefficiency with process. Process innovation is a remarkable thing. By understanding the issue and proposing a way of operating to solve the problem, the pain point can frequently be mitigated or disappear. Now, this is not as automatic as software because it requires people doing things to follow the process and usually more training than software. But processes can become hard-to-break habits, especially once employees see the benefits of them inside an organization. This is more of where departmental operations roles tend to thrive today. By understanding the strategy of the business and the day-to-day operations, operations team members can spot inefficiencies, test different process solutions and assume responsibility for scaling out ones that work. But these solutions can be led by anyone. The more this happens without dedicated operations people, the more efficient an organization is.

#3 People
My next best option after process is to solve a problem with a person. Hiring is expensive, so it should be considered carefully. I definitely prefer hiring for concrete roles that have well defined value inside companies. Engineer, designer, analyst, etc. If you need to hire an Operations role because the problem is nebulous, temporary, or today can’t fit into one of those roles, you can do it. But you should have a career plan for those roles to evolve into a more well-defined role. Fortunately, team members that showcase generic problem solving skills are great fits for many other types of roles inside companies, so they rarely have to worry about their next internal career move. Still, it may be more efficient to actually look at one of the other solutions below.

#4 Advisors or Consultants
Sometimes the right person isn’t available, or the problem is well time-boxed. In this situation, I prefer to find consultants or advisors. Subject matter expertise exists out there in the world for almost anything. Working with individuals that have specific experience makes it easy to align incentives even if this subject matter expertise isn’t hireable full-time. If the issue is temporary, you may not want to hire full-time anyway.

#5 Agencies and Firms
Lastly, I look at agencies or firms. With these companies, it is hard to prevent misaligned incentives. But they do have expertise and bodies that you can throw at a problem with less risk of being stuck with them full-time. 

Where Operations Wins
I am not against Operations roles; I just want companies to understand how to use them well and to scale out of them whenever possible. Early stage companies can absolutely crush with Operations. Smart people Swiss Army Knifing problems is many times the fastest way to scale in the early stage. Operations roles can also thrive in larger companies, if they root out inefficiency with the tools above and don’t succumb to empire building. We can’t yet automate transportation needed for the delivery of the business? Call that the Operations team. We can’t automate training for our customers yet? Call that the Operations team. 

The COO role is very common, though its definition is ambiguous because it tends to be a grab bag of executive inefficiency. Usually, the COO manages what the CEO is inefficient at. That can be management in general, or parts of the company the CEO is less capable of adding value to. The COO role can also be a roll up of certain executive functions when the CEO has too many direct reports as well. 

This is all fine and even optimal. But every operations role you add you should also add to a list of inefficiencies you hope your company can solve one day, and always be thinking towards software or processes that make these current roles unnecessary so those people can take on even more important roles over time.

Currently listening to Good Times by Moire.

The Types of Product Team Organizational Structures

There is no one perfect way to structure a product organization within a company. Like most things in a company, organization structures only make sense for given moments in time, and as changes happen with the business, so does the organizational structure to match. Product teams are no different, but they tend to vacillate between four different types of structures over time, which I’ll explain along with their pros and cons. These structures tend to work best when aligned with how engineering, design, and other partner functions are structured, so there are 1:1 relationships between leadership roles in those functions.

Alignment of Structure

By far the most important rules of product organizational structures is that they should closely mirror the partner functions. So engineering, product management, and design should tend to have structures that match each other whenever possible. This can’t always be 1:1 as engineering teams tend to be much larger, but if engineering is organized in a very different way from, say, design or product management, it can cause many problems. It can create misaligned incentives as well extra coordination between managers as one director may have to interface with four different peers to align their work instead of one. Assuming the company tries to align all of the development functions, let’s talk about a few ways they can be aligned.

Organization by Type of Product Work

In the Reforge Product Strategy program, we talk about the different types of product work. A common organization structure is to separate teams based on the type of work they are doing. One pillar is the innovation pillar working on new products. One pillar is the core pillar trying to strengthen the core product with additional features and maintaining the core. One pillar is the growth pillar trying to grow overall usage of the current product. One pillar is the platform pillar working on internal features that support other product and engineering teams to allow them to scale. 

The organizational structures can be quite stable, but the level of investment in them can change quite dramatically over time. Product leaders need to consistently be thinking about the right allocation between these different types of work and changing resourcing among them based on the needs of the business. This reshuffling can create change fatigue of individuals that have to move around teams.

Organization by Customer

If a product has different types of customers, a common structure is to separate product teams by the customers they build for. This is very common in marketplaces that have supply and demand teams, or in subscription companies that have self-serve and enterprise, or free customers and paid customers. This allows product people to become experts in understanding their customer well to deliver them value. 

These organizational structures tend to be very stable in marketplaces, but less so in subscription companies if the contracts between those teams are not written correctly. For example, I’ve seen companies that have split into free and paid where the free team is penalized when a person upgrades, which should be the very goal of a free plan. But, since the free plan was goaled on usage, whenever someone upgraded, their usage was removed from the free pillar’s metrics. Even in marketplaces, there can be issues with this model as great products are things that benefit both supply and demand, and it’s hard to build a great product if you only know one side well.

Organization by Value Proposition

If a product has different value propositions, a common structure is to separate product teams by those different value props. For example, at Pinterest, we thought about our value props as Discover, Save, and Do, and had different product pillars for each of those value props. This makes it easy to align OKRs or goals to the value you’re trying to provide your users.

This organizational structure can last for quite a while as value propositions do not change dramatically over time in most companies, but some necessary product functions don’t easily fit into this structure. Great product goals tend to be focused around value created for the customer that, in the long run, create value for the business. Value prop structures are more likely to ignore or de-prioritize that second part of long run value for the business. These structures can also overly focus on the product engineering part of the engineering stack as their goal is to deliver more value. If not handled correctly, this structure can lead to an under-investment in important maintenance, scaling, or growth work as the desire is always for new features that aid in delivering this value prop.

Organization by Initiative

Companies tend to have strategic initiatives that emerge from annual planning, so a common organizational structure is to align product and engineering around those initiatives. This process can work well when initiatives are new, and the organization isn’t sure what types of product work will be most important to succeed in an initiative yet. The initiative structure allows PM’s and engineers to flex between innovation, growth, scaling, etc. as needed to support the ultimate outcome for the business. This requires product folks to be more agile in their planning and in the skill sets they are leveraging. We organized this way at Eventbrite when I started as Chief Product Officer.

This organizational structure tends to be the least stable because initiatives change frequently or at least on an annual basis. Once the type of work that is required to be successful for an initiative becomes clear, many times teams like to specialize by switching into one of the other structures above.

Mixing and Matching 

What a lot of companies end up doing is mixing and matching a couple of these approaches to fit their needs. For example, while Pinterest used the value prop structure for the core product team, it also had growth and monetization teams to balance the business needs of the company. That combination proved fairly stable for a while. No organizational structure is perfect, and emerging trends in product, like having product managers work deeper into the technical stack on platform, infrastructure, and DevOps, will continue to shape changes in how product leaders structure their teams to drive effectiveness. Nevertheless, it’s important to think through the tradeoffs of different organizational structures to make sure they match best to the needs of the company at the specific point in time. What is most important is aligning this structure between engineering, product, and design as much as possible to the teams work in unison.

Currently listening to Hand Cranked by Bibio.

Buffing, Nerfing, and OP: What Video Games Can Teach Us About Talent Management

One of the more interesting, but less talked about, dynamics in the video games industry in the last few decades is that the product they initially ship to customers is no longer the final product. Because of online connections via mobile phones, PCs, and consoles alike, video game creators can push constant updates to their games to make them better over time in response to real-time player feedback and behavior. This makes their approach to development much more like other software in that it can be more agile and less like producing a film or a piece of hardware.

Like any change in the video game community, gamers notice, and a whole lexicon has been created based on these new abilities of game developers. One of the more common genres of video games that receive these changes over time are fighting games and shooters. If you grew up pre-internet like me, then examples include Street Fighter and Mortal Kombat and GoldenEye. If you’re, the youth, as they say, then you might be more familiar with Overwatch, Fortnite, and Call of Duty.

What these franchises do now is ship their initial products, watch the community play, and make adjustments over time. As the community plays, players and developers notice that certain characters or items are incredibly powerful, perhaps more so than the developers intended, or they change the game in some unexpected way. The community deems these OP for overpowered or OD for overdone/overdosed.

Before game developers could update their games over the air through the internet, that would mean certain characters would stay overpowered and make games lopsided if you didn’t use those characters. Players would create rules to adjust for these issues, like not allowing anyone to play as Oddjob in GoldenEye, or just blaming losses on your friend using a “cheap” character.


Oddjob was considered OP in GoldenEye because he was smaller than other characters, making him harder to hit.

What developers now do is notice these patterns and update the games over time to re-balance the game. When this occurs through over the air updates, serious gamers read through the patch notes to figure out who has been buffed and nerfed. Buffing is when a character or item is underpowered, and the developers do something to make it stronger. Nerfing is when a character or item is overpowered, and the developers do something to make it weaker. When these patches occur, the power dynamics change overnight in the game, leading to a lot of players trying new characters to see who they can gain an advantage with. This also can extend a game’s lifetime because it forces people to try new things in the game.


Cassie Cage was nerfed in the first major update to Mortal Kombat 11. Holy graphic improvements, Batman!

I find the concepts of buffing and nerfing fascinating and incredibly relevant to organizations, where employees are the players. All organizations are going to, intentionally or unintentionally, overpower people or areas of the company over time. Organizations need more tactful ways to adjust when these mistakes occur, and the buffing and nerfing of the video game industry is a concept I think can be applied successfully to organizations in this case.

So, how do founders and executives get good signal as to the current dynamics of their “players”? Video game developers watch play data and observe the community. Founders and other executives don’t usually have the same analytics video game developers have, so they need to rely on qualitative signals. Many organizations use business results and culture surveys as a signal into organizational success, and use performance reviews, 360’s, 1:1’s, calibrations, skip levels, Q&A’s, and all hands to build even more signal. If you’re not doing any of these today in your organization, start. Organizations usually know how to use these tools to identify who is doing well and needs to be buffed, and this can result in more scope, more resources, or official promotions. But our tools for nerfing are incredibly crude today, so I’m going to talk more about how to effectively nerf in an organization.

How To Execute a Nerf — Conditions for Play

One thing I want to call out about being overpowered. This is often the failure of an organization, not an individual or a team. We tend to treat OP situations in companies as a failure of the employee or team because it’s a lot easier, and we have mechanisms for those situations, such as demotions and firings. And this is typically the way organizations fix OP problems. To do a nerf effectively requires an organization to understand that it failed in structure or talent management, creating the OP situation. Talent management doesn’t just include performance management, but mentorship opportunities and career pathing. Only then, can it think about using these nerfing tactics effectively.

Nerf Tactic #1: Change the process

One way an employee or team becomes OP is because they manage a key process in some way that gives them undue influence over others. The easiest change then is to change the process to re-balance some of that power. In order to understand how to do this, you need to a) understand the process and b) understand the failings of it according to others. When members of your team that are OP manage a process, they seldom see the flaws in it because of how much control it gives them. So you have to seek out different people’s opinions in the organization as to what is going wrong. A signal that revisiting a process may be a good solution is when other senior team members complain, or if they have enough power, start opting out of certain other processes.

Nerf Tactic #2: Change the structure

Another way an employee or team becomes OP is the structure itself. This tends to happen when functions are grouped. For example, if a GM also has control of sales and marketing, they may become OP. Or if your CMO owns customer service, they may become OP. Neither of these are bad if they occur, but they may end up giving that executive too much power, so they can bully other teams, or they may not be as effective at managing either the scope or the function they’re less familiar with. In this case, the easiest path is to separate these functions or create more dotted line ownership to re-balance the teams.

Nerfing Mistakes to Avoid

#1: Don’t Wait Too Long to Nerf

The longer a power balance is allowed, the higher the chance that the organization will blame the strife on the person/team that is OP rather than the structure itself. Even when that person or team is nerfed, animosity will remain that may make the organization not want to work with the person or team, and continue to impair their performance. When you wait too long to nerf, you’re effectively destroying people’s careers in your organization, which may lead to them leaving. The worst situation is when you have to let go of someone who could have been great with a less powerful scope, but you waited too long to do it. In this case, firing or radically moving the person to something else is the only option.

#2: Don’t Change Titles When You Nerf, Especially Downward

As I said earlier, the most common way organizations nerf today is through demotions, which implies the employee failed instead of the organizational structure. If you absolutely have to change titles because the scope change is that significant, I prefer keeping the level the same, just changing the functional name of the role. Say, for example, you have a Director of Strategy, and they became OP, but you want to retain them. Changing their title to Director of Competitive Research is better than changing their title to Manager, Strategy. Why is this? The demotion indicates failure not only to them, but the rest of the organization. These people usually exit their organizations shortly after the demotion.

Organizational Mistakes That Prevent Effective Nerfs

#1: Inflate Titles

I was talking with a startup recently who hired someone to be their first product manager. They had made a mistake that happens commonly in startups — to make the role attractive or to reward performance once in the role, startups inflate the role title (to be more senior than what that role means on the market). One common example is calling your initial Product Manager a VP Product, or worse, a Chief Product Officer. When the company grows 3x and you’re now asking that product manager to manage people for the first time, these people frequently aren’t ready. Then, in order to fix your organizational mistake, you either have to change their title, which will look like a demotion to them and the organization to hire someone more senior, or try to seek out on the market effective mentorship for them to scale up their career progression faster than is normal.


In the words of Keith Rabois: Wrong.

It’s enticing to inflate titles to make people happy or to attract talent, but it removes your ability to nerf without demoting. In practice, I like to reserve C level titles for public companies and VP titles for managers of managers, though I will be the first to admit that impact is not defined by the number of direct reports. This is not always possible with companies that need their employees to do a lot of external to company work. “Head of” is a happy medium startups are starting to use, but it can still feel like somewhat of a demotion when that title is converted to, say, a Director, when a VP is hired.

#2: Confuse Being OP and Poor Performance

I want to be perfectly clear: do not nerf for poor performance! You nerf when someone was performing well, and a process or scope changed to unintentionally give them too much scope. If you have a good CMO, and you ask them to take Customer Service, and they don’t manage it well, you still have a good CMO. Change the scope, not your performance management strategy for the CMO.

What if you promoted someone to a new level, and they are not meeting it? Well, that is not following performance management best practices. You should be promoting someone when they are already performing at the next level for some time, which eliminates the risk of overpowering them. This is why you want to have career guides with clear levels and expectations for them, so you promote only when it is appropriate. Hired someone at too high a level? Do not nerf; demote or fire. Yes, they will most likely leave, which is why you want to be careful about the titles you give just based on interviews and not actual job performance. What if you have a big hole to fill in the organization and have to do it internally with someone who hasn’t demonstrated all the skills necessary? It happens, but recognize this should be more of a last resort situation.

What about people who move into new roles where they are not effective? This is also a situation I prefer not to have happen. I much prefer creating apprenticeship programs within organizations where individuals try the role for a while before they are permanently placed in that role. Apprenticeship is therefore the evaluation of whether the person can meet the expectations of the role. I recognize this is not always possible, but it’s a sound strategy nonetheless. We do this in product management at Eventbrite today. Those in other parts of the organization in good standing with their manager can work with a product manager on a project to see if they like it, and for the organization to see if they would be good at it.

Nerfing Best Practices

#1 Take the Blame

If you are nerfing an individual, it’s important to make sure they don’t feel like it’s a demotion. When announcing the nerf to your employee, make sure they know the reason for the nerf to occur, and that it is your fault, not theirs. You gave them too demanding a scope, and you’re fixing it. If you’re nerfing a team, this is usually less of an issue. Also, make sure that others in the organization that were affected by the OP individual or team know that you believe this to be your fault, and they should not hold animosity toward the individual going forward.

#2 Thank the Individual You’re Nerfing

Whether the change that made the individual or team OP was intentional or not, thank them for their effort to help the company, and say that the nerf is a way to make sure they can create a positive impact for the company with the right scope. People should not be penalized for trying to step up for the organization.

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I think it’s incredibly important to manage performance of people and organizations. The gaming community has created a vocabulary that provides a solid analogy with corporations, allowing us to separate performance issues from structural mistakes. The more companies can separate those issues from each other and use different tactics to manage them, the stronger those organizations will be.

Currently listening to my 2019 playlist.

Thinking Outside the Job Title Box: How to Thrive in Undefined Roles

As a leader of a large team, the members of my team tend to have pretty well-defined roles, like designer, or product manager, or researcher. They also tend to interface with other employees of the company with pretty well-defined roles like engineers, analysts, data scientists, etc. Now, most of the time, these well-defined roles operate in cross-functional teams. But, what if you don’t operate within one of those roles, or don’t want to fit the mold of these well-defined roles? How do you work with teams? To answer that, it may first be helpful to understand how these teams form.

“In the beginning, there was an engineer.”

Most startups begin with an engineer building something from scratch. As the company scales, usually a designer is added next. Then, as keeping track of projects between the designer(s) and engineer(s) becomes onerous, a product manager is added. Then, as the team scales and problems become harder, the product manager and engineer(s) don’t have enough time to fulfill the analytical needs of the team, so they hire an analyst. Then, keeping up with users becomes too time consuming for the designer or product manager, so they add a researcher, etc. This is an overly simple example, but all cross-functional teams grow larger as the company scales, with more specialized roles over time. One issue you may have if you don’t fit into this model is that you want to perform a more specialized role than the company has scaled into needing yet.

The opposite can also be true. You may want to do bits and pieces of a well-defined role, but not all of it, or may want to combine some elements of a few different roles into your job. Either of these situations can be totally fine. But each require a more tactical, subtle approach to working with teams than fitting within well-defined roles. When people outside of the cross-functional teams want to work with these cross-functional teams, they frequently perceive friction. They interpret this as political, when in fact, it is structural.

By definition, when you don’t have a clearly defined role to others, they do not know how to work with you. The onus is on you to prove value so that they want to work with you, because they don’t have to. Usually, my advice when people come to me with these problems is to switch to a more defined role. There may be a valid reason to leave your role less defined though, and in this case, I propose a framework for finding a valuable fit within a cross-functional team.

While all cross-functional teams have well-defined roles on paper, in reality, for all the needs of a team, people within the cross-functional team trade off responsibilities based on skill set and interest. You may have a PM who’s better at execution, so the designer takes on strategic duties, for example. What you’re trying to find with a less defined role is a team that has a need for a skill set, and wants someone to fulfill that need.

What happens in each of these boxes? Well, if your role is not needed or wanted, then you don’t get an opportunity to help. If your role is wanted, but not needed, you tend to be superfluous and lowly leveraged. If your role is needed, but not wanted, you experience rejection. If your role is wanted and needed, that’s where the magic happens. You integrate into the cross-functional team well, help them achieve their goals, and likely are happy in what you’re doing.

Two Tips to Make These Roles Work

#1 Get a senior leader to sponsor your effort
It’s almost impossible to make this type of role if your manager and ideally someone very senior in the organization support it. If senior leaders are very strict about team formation, it just might not be the company where you can be successful in a non-uniform role. Also, if your manager doesn’t support the direction you’re targeting, there will be a big mismatch come review time that will stifle your career.

One way to be more successful with managers and senior leaders is to be very clear why you want to work this way and what value it adds to the company. I would not recommend going to managers and senior leaders suggesting you not fit a typical role in the organization, and then ask how you can be effective. You are not giving them two problems: 1) someone who won’t fit into the traditional organizational structure and 2) someone who doesn’t know how to help the company. For many managers, this would trigger them to ask why you’re at the company in the first place if you don’t know how to help.

#2 Approach teams with humility
Your approach to talking to managers and senior leaders about your role should be very different from how you approach teams. While with managers and senior leaders, you want to make a clear case of the value you can add and what you want to do, that can not work so well for approaching teams. A better approach gets across a few key points:

  • You’re interested in the problem they’re working on
  • You think they are doing interesting work
  • You’re just here to help in whatever way you can
  • These are the skill sets you have that may be valuable
  • Finally, the ask: What can I help with?

Whether you have a traditional or non-traditional role in a team, the first step is building trust, and that is usually earned by doing smaller tasks the team is not getting to and would like help on. From there, you earn the right to work on more critical tasks. It may take some time to get to the role you’re most interested in playing on the team, and that is normal.

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At Eventbrite, we have multiple people who sit outside the traditional paradigm of well-defined roles who are thriving. They all found a way to add value to a team that was wanted and not competitive, and the team operates better for it. But this all happens on an opt-in basis. The teams chose to accept them. If you want to play outside the lines, you have to understand that other teams playing with you is entirely opt-in on their part. This is the risk of not participating in the structure the company operates in; you may find opportunities to help that the team isn’t welcoming to, and there’s nothing you can do about it.

An Alternative Approach to Re-Orgs At Your Company

Re-orgs are an essential part of scaling a team at a company. The organizational structure of the company six months ago may no longer align to the needs of the company or its customers today. While most people would agree with the statement above that insists re-orgs are necessary, everyone hates them. They almost always make some people unhappy, cause employee departures, and stifle productivity both before and after they are executed.

I’ll start with a story of how this works in practice. Grubhub had a fairly stable structure for most of the time I worked there. While it was stable, it certainly wasn’t traditional. While we had crafted large sales, marketing, and customer service teams, we had a very small engineering team for our size and no official product and design teams. The latter two we de facto managed by marketing and a combination of executive leadership. While most companies at the time had a clear product manager role, Grubhub did not. We had product strategy led by marketing and the co-founders, and project managers within engineering that worked with those stakeholders to build effective software. I hired a member of my team to build a loyalty program. This meant that they would do user research, build models that project impact and costs, and work with engineering to launch experiments that would increase frequency of ordering on Grubhub. The person we hired was, in short, awesome. She did a bunch of great research partnering with our UX researcher, built detailed financial models that projected impact, brainstormed many ideas with our designers, and built good rapport with our project managers and engineers when it came time to finally build something.

Around this time, we started discussing as a leadership team if it made sense to start building a product management function for Grubhub. Being privy to those conversations, as I was having my quarterly review with this member of my team, I suggested product management would be a good avenue for her if we create that function, but she would probably need to leave my team to do it. We talked through the details of why I felt that made sense given what she was doing, and she was very open to it.

Fast forward three months, and as I’m on my way to work, I receive an email from my manager the VP Marketing asking to meet when I get in (she always got in super early). When I did, she announced that we were creating a product management function, and that as they thought about what the members of that team should look like, they felt like this member of my team was a perfect model of what a product manager should be at Grubhub. So, effective immediately, they were moving her off my team to be the first consumer product manager. The co-founder of the company was meeting with her when she got in to explain the move, and email would go out right after, and my 1:1 was with her later in the day.

That 1:1 was awkward. While this was ultimately what I wanted for her, and she was nervously happy about it (it’s nice having the co-founder of the company say your behavior is a model of behavior they want at the company), things still felt off. What is supposed to happen to her current projects? What new projects is she picking up? She at one point during the meeting said “oh, you seem sad”. And I wasn’t, just more caught off-guard, and thinking even though we’re making the right decision, are we making it in the right way?

This I find is usually the best case scenario for re-orgs. VPs and C level execs are attuned enough to make the right calls, but execute it top down without director, middle management or IC involvement or feedback on their ideas, leading to a change that is good on paper and may be good in practice too, but seems to strip the team of control. And far more common is the flip side of this scenario: when VPs and C level execs think they know what is good for the people and the team, don’t seek out necessary feedback, and make the wrong call for both the organization and people’s careers who are affected by the re-orgs.

For one of my the companies I advise, going into 2019, for one our business units we knew we likely had to change our organizational structure. Trying not to repeat re-org mistakes, we started working on a structure that would make the re-org act like a feedback-fueled progress driven by the teams instead of by people above them. The first thing we worked on as a leadership team was the objectives for 2019. What did we need to achieve next year to be successful? We then went to the product managers, designers, and engineering managers and explained the objectives. We then tasked them to propose the organizational structure that would help them with these objectives.

They worked directly with their teams to make sure everyone understood the objectives, everyone’s interests and career aspirations, and then they proposed the structure to the leadership team. After this presentation, we worked more to understand the constraints that led to this recommendation, worked through some of those constraints so the team didn’t need to make as many compromises on what they wanted, and then solidified the structure. The product managers, engineering managers, and designers talked through the changes with the rest of the teams, and organically the teams started planning with the new structure in mind. They then set their own team objectives to the align to the business units, as well as their roadmap and key results.

By involving the team members that would be effected from the beginning and making it their decision, we avoided a lot of the awkwardness or bad calls of many re-orgs I have participated in. The teams are happy and working on the new objectives seamlessly. Now, there will certainly be re-orgs that can’t be this inclusive, such as those that involve the transitioning out of an executive, or with teams that would not be capable of tying the objectives to an effective team structure. The former will never be seamless when people’s managers leave. The latter indicates a separate problem of lack of team responsibility that needs to be addressed first. But if you are not facing one of these scenarios, here are some things I have learned you may want to incorporate into your next re-org.

  1. Start with making sure the objectives of the company/team/business unit, etc. are clear, and that the executive team is aligned on them.
  2. Inform the teams affected that the new objectives create an opportunity for them to re-organize to be more effective at achieving these objectives.
  3. Empower the teams to propose a new structure that would better allow them to achieve the objectives
  4. When these teams present their proposals, make sure they focus on talking through the constraints that led to their proposal. These are frequently resourcing e.g. not enough Android engineers, cross-department collaboration or lack thereof e.g. no SRE support next quarter, technical or design debt, et al., They can be relationship based or based on location for distributed teams.
  5. Resist the urge to edit the choices directly as a leadership team. Instead, focusing on editing their constraints.

The Analyst Career Path

I’ve written before about analytics teams as a crucial function in today’s technology companies. Technology companies are rapidly hiring analyst roles to pair with their product teams. And while my previous post discussed how to hire analysts and structure their teams within organizations, I haven’t written about how analysts should approach their careers.

Many technology roles, at startups in particular, have an issue with career progression. While established industries have defined career ladders, the path of career advancement is much less clear in many technology roles. Engineering, being the largest and oldest function in technology companies, now has a well defined individual contributor and manager career path all the way up to VP Engineering and CTO. Product Managers know they can progress to manager roles at their companies all the way to VP Product, and if they want to remain and individual contributor, they can still grow by working on more and more complex and strategic products over time. As I’ve talked to many analysts and analytics teams, this progression is not as well defined. I will outline how I think about this progression as someone who has been an analyst and managed analysts.

Option 1: Graduate into Data Science

If someone wants to remain an individual contributor and not manage, at some point the only way to become a better analyst is to graduate into a data science role. Now, there is some confusion with where the line is between analyst and data scientist, and many companies just call all of their analysts data science as a form of title inflation. I define the role of an analyst as someone who uses data to help identify and communicate business opportunities, and drive decisions for teams. This includes targeted analysis driven by others as well as free form analysis driven the analyst. From a process perspective, this includes everything from making recommendations, helping with experimentation, and creating dashboards to help others make decisions. From a tooling perspective, this means everything from writing SQL queries, identifying logging opportunities for product engineering and database design opportunities with data engineering, creating new dashboards and visualizations. An analyst retrieves, analyzes, and recommends, and is judged by not only how good those recommendations are, but how often they are followed.

So, how does data science differ? A data scientist writes code beyond SQL to manipulate data for analysis and potentially for product experience. A data scientist can write an algorithm that powers a personalized experience in the product, or just do more complicated analyses requiring more sophisticated querying using Python, R, etc. Data scientists jump in when analyses are too complicated to be handled by analysts, and also frequently partner or embed with product and engineering teams to change the product. This is more than just a higher-power analyst role though. Data scientists have deep expertise in certain areas, like machine learning, statistical inference, and focus on solving specific, hard problems over longer time horizons.

Option 2: Become an Analytics Manager
If you wish to get on a management track, becoming an analytics manager is the natural path. Since analysts are being hired so frequently, they need managers who can mentor and coordinate learnings between teams. While analysts are best embedded, analytics management bears the important responsibility of solving company-wide analytics issues related to tooling, process, etc.

Option 3: Graduate into Product Management
The third path that analysts can choose to grow their career is migrate into product management. Technically, product managers and analysts are peers in cross-functional teams, but product management has better career pathing that doesn’t require as much technical investment as data science, and product managers tend to have a bit more power in organizations today.

The migration of analysts to product manager is increasingly common as more and more product teams rely on data as the foundation for most decision-making. This has certainly been most true on growth teams and teams that utilize personalization, but I believe all future product teams are data savvy. A significant percentage of product managers at Pinterest started as analysts at the company. This same migration is also true for marketing analysts. They tend to become quantitative marketers over time, or switch to product analytics.

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Being successful as an analyst is peculiar is that it almost requires a switch in roles over the time in ways that are not true for design, engineering, and many other roles in technology companies. Fortunately, the analyst has a lot of choices on how to progress within an organization. Hopefully, managers of analysts get better at outlining these different opportunities and help analysts position themselves toward the best ones for them over time.

Thanks to George Xing for reading early drafts of this.

Currently listening to Compro by Skee Mask.

The Autonomy Spectrum: How Much Autonomy Should You Give Your Teams?

Many people are familiar with Dan Pink’s work in Drive that to be the most productive, happy at work, etc., you need to have autonomy, mastery, and purpose. While a lot has been written about how to create purpose inside companies and crafting compelling missions, I would like to spend some time to dig into the details on autonomy. As founders and senior leaders of companies, it can be tough to understand how to give autonomy to employees and also drive toward a singular vision and commit to things that need to happen for other components of the business to work. I have found creating a spectrum of autonomy is helpful, and discussing with senior leadership and your team where you are on that spectrum.

How do you create an autonomy spectrum for your team or company? It’s helpful to start at the extremes. On one end of the spectrum, you would tell your team exactly what to do and how to do it. This is a complete lack of autonomy. On another end of the spectrum, employees have free reign to work on whatever they would like to work on. These projects may have nothing to do with the business, or could be completely aligned. That represents 100% autonomy.

Usually, people agree that neither extreme is particularly helpful. So how do you decide where in between your company or team should be? I like to work backward from 0% autonomy, and see where leaders start to get less comfortable. Let’s take an example recently from my time working with one of the companies I advise. The CEO asked me to come in and help the leadership team think through an expansion of their product. So that is step 1 of the autonomy spectrum, handing a business opportunity to the team from the CEO.

CEO: We have this opportunity for expansion (Business Opportunity)

Working down from that requirement, one executive volunteered to lead this initiative and did a bunch of research on the expansion opportunity. She talked to potential customers of the expansion, validated the pain points of this segment, and discovered a need the company could solve. So, she started settling around a vision of a new product experience leveraging the company’s existing strengths and identifying what new strengths needed to be built.

Executive: The way to attack this opportunity is to solve this specific problem for this segment (Persona and Product Vision)

The team she managed built an MVP attempting to solve this problem, and measured a lot of early usage and did qualitative research on what they had built. At this point, I stepped in to temporarily lead the product team and saw specific issues from the data and the research around the breadth of the solution, the quality of the options we provided, and the value of our solution vs. existing competitors in the market.

VP Product: Solve these four problems with the event discovery app (Problem Scope)

I also saw a team whose operating cadence matched a mature product with clear requirements rather than a fast moving team that uses research and experiments to find product-market fit. So, I created a new process that would structure them better for the problems they were facing and give them more autonomy.

At this point, we worked as a team to organize all of the product teams to work on these problems. As a leadership team, we chose not to identify solutions to these problems, but to put the product teams in charge of determining their own potential solutions. We created a weekly time where our persona would be in the building to provide feedback to our work. We also created a weekly meeting to review research feedback and experiment results.

VP Product: Test ideas with our target persona and run experiments targeting these problems (Process)

This is where we chose to sit on the autonomy spectrum. Prioritize business opportunity, vision, scope, and some process. Create autonomy for the team to define solutions and deeper process on how they want to get there. There are of course other options here. We could have chosen to prioritize ideas the teams invent to solve these problems, even come up with the solutions or how they would validate with research and experiments. There is no clear cut place to draw the line where you start thinking this way.

What is more important is to try to move the line to the left over time. When I advise leadership teams, I tell them that their goal should be to push decision-making as far down the org chart as possible. For leaders that have historically erred on the side of low autonomy, they need to understand how far they can start to push decision-making down without creating chaos. After all, Pink says that mastery is about providing stretch assignments, but not assignments employees cannot possibly be successful in. This process usually starts by moving to one additional layer of autonomy than normal and measuring results. If that is successful, leaders can be confident moving to another additional layer of autonomy. If this is not successful, then leadership needs to think about what type of training it needs to build so that this is possible in the future. I foresee a future at this company where the teams are in charge of prioritizing the problems as well as the solutions because they will be the experts from talking to our persona every week.

This is how Pinterest operated. Product teams created their own missions and problems they wanted to solve, and they were approved by the leadership team. Every six months, teams updated their OKRs to define the new problems they wanted to target and how they would measure success. No company starts there. Especially with startups, founders are used to setting the vision as well as coming up with product ideas. But as companies scale, leaders have to defer decision-making more so they can continue to move fast. The founders cannot be in every meeting nor can they be the experts on every topic.

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Autonomy is a difficult topic to grasp inside a company. No CEO or senior leader wants to hand over the reigns to every decision to a team of varying levels of experience and confidence, but trying to make every decision stifles creativity and limits execution pace. Use the autonomy spectrum to build a honest understanding of where the company or teams you manage are and where you would like it to be over time. When you’re confident you are in the right place, communicate this spectrum and why you have made the decisions you’ve made on the level of autonomy you’re comfortable with. Employees will have a much clearer understanding of their role and can build better mastery and purpose as a result.