Ask Why It Won’t Work, And Other Lessons This Founder Relies on While Building From 0 to 1

 is slightly obsessed with one exercise these days: pre-mortems, or the act of thinking through why a particular strategy, product idea, or candidate might not work out down the line. This isn’t a typical focus area for founders. In our experience, they’re usually an optimistic bunch, the types who spend time dreaming up big ideas and figuring out how to run through the walls that may stand in their way — more the “move fast and break things” school of thought.

 want this?’ is often a far more interesting question than why they would

. When you're working on a product idea, there's a thesis for why you believe you’re right and it's really easy to constantly confirmation bias yourself into believing it’s the optimal decision. But once you can also find the counterpoint, the scenario where you’re wrong, you can start teasing out when it would start to make sense — the point at which it 

Oftentimes the question of why something 

 work uncovers the element that actually 

Song has had plenty of experience with making things work these last few years. Since co-founding 

 in 2018, the CEO has had his hands full with the intricacies of the 0 to 1 phase of company building. 

Prior to starting Persona, Song spent five years at Square as an engineer and early team member at Square Capital. It was here where he first had the insight that led to starting a company. From fraud prevention in lending, to trust and safety with food delivery for Caviar, he gained exposure to the wide range of use cases in identity verification — and saw that one-size-fits-all solutions were falling short. With low- and no-code building blocks, Persona’s platform enables customers to craft a more tailored experience.

As investors in Persona’s seed round, the First Round team has had front-row seats to this early startup journey, and we’ve come to believe Song is one of the most thoughtful founders around. And as 

, Persona is at a particularly interesting inflection point — they’ve raised a $50 million Series B and are looking to double their 50-person team this year to keep up with revenue that’s surged more than 10x and a customer base that’s grown to include some big logos like Square, Postmates, and Gusto.

In this exclusive interview, Song takes time to share what he’s learned on his company building journey so far, diving deep into how he brings the pre-mortem mindset to every aspect of running Persona. 

Starting with recruiting, he shares the lessons he learned — and had to unlearn — from his time at Square. Next, we chatted about why Song believes it’s not about going down to first principles, but rather studying other companies to find unusual moves and experiment with different strategies and frameworks — of course, questioning why they might not fit your business along the way. From the strategy behind Persona’s multi-product approach — including a candid discussion about the risks — to why his engineers sell, Song shares a detailed look at his go-to-market thinking.

In our view, there’s a trove of insights in here for founders or those toying with the idea of starting a company one day, but there’s also plenty for engineering leaders and hiring managers as well. Let’s get to it.

LESSONS ON RECRUITING: HOW TO HANDLE YOUR FIRST 10 HIRES AT AN EARLY-STAGE STARTUP

Much of Song’s hiring philosophy stems from his days at Square. “One key piece of how Square scaled this was setting up an entire ladder of how to progress as an interviewer. They weren’t putting people on the critical path of determining whether someone would get an offer or not on Day 1,” he says. 

“There was an entire training process for anyone to become an interviewer and it was very rigorous,” Song says. “Then you'd start off on the interview panels. And once you got your bearings and did a fair number of interviews, you'd become a phone screener, assessing the technical capabilities of candidates on the initial calls. Usually the more senior interviewers were the really good phone screeners. And then for the folks who were incredibly predictive as to whether someone will be successful or not within the organization, they became barometers — the people at the very end of the hiring process who helped determine whether to extend an offer.”

Below, Song delves into his top hiring takeaways from both from his time at Square and building out Persona’s early team.

Lesson #1: Get granular on why a hire won’t work out.

It was from those barometers that Song picked up a critical hiring lesson. “The best hiring advice I received at Square was that when you're about to extend someone an offer, you're thinking to yourself, ‘There’s so many problems this person can help us solve, they’ll be amazing.’ And this almost certainly will be true. But

 it's actually far more helpful to think about all the ways in which this person may 

 work out for your organization — who on the team they might not interface well with, the types of projects they may not succeed in

“The first three months of any new hire is a honeymoon period that masks a lot of otherwise clear problems. Thinking really deeply about all these potential pitfalls can help set you up for success downstream and make sure that this individual is successful as well.”

Of course, every hiring manager weighs the pros and cons of candidates. But Song shares some practical advice on how to spend more time measuring the minuses. Here’s how he operationalizes this “why they might not work” mentality: 

. “In the early days, I used to write a doc, jotting things down for myself as to who would this person work with and how would they do. These days as we’ve scaled, it’s more about coaching hiring managers to think deeply about this,” says Song. 

. “We ask managers to make a really strong pitch to themselves about why this person may not work out and just be heavily aware of the potential pitfalls.” There’s an important distinction here, though. “Externally to the rest of the hiring panel and the team, you should be the absolute champion for the candidate. But internally or in discussions with your own manager, you need to be thinking through what may not go so well,” he says. 

Bias toward no if you’re on the fence. 

“Although saying no may feel harder, it's far better to be a little bit more pessimistic. Hiring is such a big deal when you're only 10 people — it's a 10% incremental difference in terms of the size of your team. That's enormous. So being a little bit more pessimistic can really save a lot of heartache in the early days.” This may seem obvious, but consider the strain that early-stage startups feel as they struggle to stand out in the hiring market. “It often feels so hard to hire folks. In the early days, there's so much difficulty in trying to convince anyone to join. We initially had a tendency to rush decisions and try to hire someone a little bit sooner than we actually needed them. But adjusting to be more cautious and bias toward no has paid off so much for us.”

This approach of course hinges on a crystal-clear understanding of what you’re looking for and a well-developed sense of what a candidate brings to the table. Here, Song shares his criteria:

“This 11th hire has to work well with all of the first 10 people on the team. As companies scale, generally you have more pockets and groups — and problematic relationships can be a little bit more hidden away. But for the earliest stage, there’s no escaping it. Think critically about whether this individual will actually interact well with everyone else here,” says Song. “More specifically, I try to think a lot about how this candidate would interact with the top five people I expect them to work with on a daily basis. And what are core aspects of their working style? Is one person particularly process heavy, whereas the other is much more loose and adaptive? Are the communication styles fundamentally different? Does what they value differ greatly?”

“If this person is more of a big idea type of thinker, could they handle particularly complex projects where there's a lot of nuances? Are they more social? Do they prefer a leading role versus a supporting role?”

“Who are they as an individual and what will really make them feel excited about being here every single day? We want to make sure that we can provide that, that this is a place they can be successful. But especially for non-technical roles, it can be really difficult to assess how a person will actually do the job,” says Song. “For most of my interviews, I actually ask very little about how they would solve a particular problem. When it comes to questions like “What was the hardest challenge you've ever faced?’ often a lot of candidates have canned answers. Instead, I focus on the incentives. What do they care about? What motivates them? What drives them? If it's an hour-long interview, I’ll spend 40 minutes diving very, very deep into what this person wants to do. What is their ideal day to day?”

I'm a big believer that if you can get to the root of someone's motivations, you can sort of work out how they would tackle many problems.

“For example, if someone's incredibly motivated by supporting others, you can usually get a good sense of how they’ll behave when there's a product launch or when a customer challenge arises,” says Song.

uncovering motivations through interview questions

 isn’t easy. “I like to ask, ‘What do you want to do after this role?’ and ‘What are the most important things that you're looking for in your next role?’ For the latter, it’s common for candidates to focus a lot more on the size of the market and impact on the world. But for us at Persona, I’m heavily biased towards people. So if I don't hear that the number one thing that motivates them is people — the folks they work with, or the customers they support — I usually think that this probably isn't the best fit,” he says.

Even when Song does hear that shibboleth in a candidate’s answer, there are still deeper depths to explore. “When you say people are important in your next role, what do you mean by that? Does that mean day-to-day or long-term impact? Is it someone you can joke with or hang out with after work, or is it about being surrounded by people who are similarly motivated? Is it people who you admire versus people who you can learn from?” he says.

Lesson #2: Focus on setting the foundation and finding the glue.

It helps to have an understanding of the pitfalls you’re likely to encounter when hiring, and these lessons were hard won, Song says. “When hires haven't worked out, it usually stemmed from us not understanding the role itself nearly well enough, especially for the first person in a specific role we weren’t that familiar with,” he says. 

“Early on, we had a tendency to hire much more for potential. But requirements of the company often outscaled that potential, which meant that the individual had to grow far faster than they may have even been able to, and in a way that frankly may be toxic towards their own growth trajectory. It was key to spend more time on understanding that role and doing it ourselves for a while to figure out 1) what level seniority we need to hire for and 2) whether we needed to hire someone who already understands this role deeply.”

Song offers up an example: “For our first business hire, we brought in 

, who had a lot of experience leading people and had been at a variety of startups — she knew what she was doing, which was important because she was setting the direction for sales, marketing, customer success, and much more. Whereas on the engineering side, both my co-founder 

 and myself came from engineering backgrounds, so we could really tackle a lot of the foundational pieces and bring in some less experienced folks who could grow with us.”

Part of this comes down to understanding whether it’s a 

. “On the product side, we were still trying to understand what our product is and oftentimes the mistakes that you make are much less costly. Design is also easier to mold and redesign in the early days, and we’re a B2B SaaS company so it wasn’t an absolute pillar initially. Of course, this has evolved and changed, so we’ve started hiring more and more senior folks in these areas as we’ve scaled.”

If you're trying to hire someone to lay the foundation in a function, you can't really bet on potential no matter how much they have — because everyone else will be building off the exact same foundation.

Another frequent pitfall? Missing the mark when assessing the candidate’s motivations. “When it doesn’t work out, I always look back and try to think about what I missed in terms of what this person cared about or wanted to learn. And I think we've had a couple of cases where we felt an immense alignment in terms of core things like people and culture, but we didn't effectively highlight 

what joining a startup for the first-time requires

. There’s an immense amount of pressure, and work-life balance can be very hard to achieve, especially in crunch periods. Painting a picture of what that looks like is important,” he says.

But that’s not to say that Song’s in the “don’t hire anyone from FAANG” camp.“The vast majority of folks here at Persona actually have no startup experience and largely come from big companies. I often joke that we're an entire company of people who have never done startups, but are all trying to learn together at the same time — and I don't know whether that will be a disaster or not,” he laughs. “Hopefully it’s clear that it’s a very friendly learning environment for all of us.”

This runs counter to common wisdom that candidates from top tech companies tend to flounder on a smaller stage with fewer resources. “There are a lot of founders out there who don't have experiences at a larger company, so it can be a bit of a black box in terms of assessing an incredibly specialized candidate and figuring out if they will actually adapt to a startup,” he says. While there are risks, Song sees clear advantages.

“One, you generally have a sense of what this function looks like at scale. Because startups grow unbelievably quickly, knowing what the end result looks like and being able to plan backwards is impactful. If you've only been at startups, you've seen how it works at a smaller operation, but the scaled up portion may be far more challenging and the pace of startup growth makes it very easy to level out.”

The key is finding the big company candidates who have scrappiness in spades. “We're looking for the people who have been the ‘glue’ — the ones who plug all the holes, are maybe a bit less recognized but constantly make it work and tackle problems that no one else was really dealing with,” says Song.

To unearth these hidden gems, ask more about the larger architecture to see how they interfaced with different functions or problem areas. “The utility player type engineers can go so deep on so many different topics of the entire company,” he says. References are also a great place to mine for insights. “If you ever hear things like, ‘If you asked this person anything about the company, they knew how it worked,’ or ‘They will literally run through walls to get something done,’ or ‘They will work with anyone,’ that’s a great sign this candidate could be amazing in a startup setting.”

Candidates who filled the gaps and served as the “glue” at big companies both know what the future looks like and have the scrappy spirit that makes for a great startup hire.

Lesson #3: Think of hiring as a segmentation exercise.

“One mistake we made in the earliest days was that we tried to create an entire track for interviewing. When it was just my co-founder Charles, myself, and maybe two other people, we prematurely created an entire interview loop, with phone screens, interview problems and onsite interviews, perhaps to make it seem a lot more mature than it actually was,” says Song. “But coming from a large company like Square, often when candidates apply, there's a very high probability that they'll join you. You're an established company. They intentionally came in. And when you're a small startup, it's very different.” 

Startup hiring isn't just about sussing out whether this person's qualified, but actually remembering that every single interview is also a sell.

“If you're trying to attract top talent, a ‘First, let me make sure that you're good enough’ approach creates a weird power dynamic that makes it incredibly hard to hire. You really have to start with a much more back-and-forth approach,” says Song. “Keep the early conversations casual, and make sure the relationship is more of a horizontal-like camaraderie dynamic where you look at the individuals as equal — because for these first 10 hires, it really will be more like that.”

To foster this atmosphere in interviews, Song and his co-founder focused on turning them into conversations where candidates could teach them what they do. “Given that we were so early, we didn't know how half these functions worked. 

 of the things that you aren’t particularly good at as a founder is important,” he says.

Vulnerability also plays a critical role in another aspect of Persona’s recruiting philosophy. “I try to think about hiring almost as an exercise of segmentation. Today it seems as if every single startup out there is talking about hiring for mission, or how they’re going to become the largest company in the world. As a result, 

this ‘You're riding on a rocketship’ segment of recruiting messaging is incredibly crowded. So we’ve taken almost the complete inverse approach

. I often say to candidates something along the lines of:

We're not trying to change the world, we're just hoping to make it slightly better. And hopefully if we succeed, people never think about their personal information being lost or mishandled ever again. It's essentially removing a burden for a lot of people. Whether it's a rocket ship or not, I can't promise you that. I don't know where Persona will be in 10 years — if we are huge, that'd be absolutely amazing, and if we're still alive, frankly, that would also still be amazing

We're just trying to take it step by step, and make sure that this is a great place day-to-day for everyone here. As a founder, all I really try to index for is that 10 years down the line, if we were to suddenly go out and say, ‘Hey, there's going to be a reunion,’ we would all really look forward to seeing each other. And if that were true, I would think I've done a great job.

“And a lot of this hopefully runs a bit counter to traditional startup hiring messaging. In practice, it’s been really helpful for us, not just from standing out in the market and winning candidates over but also in reinforcing a culture of humility, a culture of really wanting to work with other folks and 

 a lot more about the day-to-day experience,” says Song.

Find out what’s uniquely attractive about your company. It doesn't have to be what's traditionally attractive — there will always be a segment of the market that is under-tapped.

LESSONS ON BUILDING THE BUSINESS: FIGURING OUT YOUR MODEL AND GETTING BETTER AT DECISION-MAKING

With a team assembled and a product that’s starting to take shape, the next frontier is fleshing out the strategies that will get it into the hands of customers, help the business run like a well-oiled machine, and set the scene for the company’s next play. 

 tend to be overlooked, and Song highlights another neglected area: whether a popular framework or strategy is actually the right fit for your startup.

At an early-stage startup, you'll be just bombarded with advice. You'll hear that X company did Y and it was so successful, or this strategy works so unbelievably well, whether that be OKRs or frameworks for product decisioning, like 

. All of this advice is correct — given the right context

“What's much more interesting than figuring out how to execute this framework perfectly is discovering when it does 

,” says Song. This concept originally comes from game theory. “It’s the specific spot in which the decision shifts, where you were going to bet and now you’re going to fold.” 

As individuals, we focus way too much on one decision versus another, but not nearly enough on the meta question of the context that would cause that decision to change.

A few variations of this framing to get your gears turning:

•Where's the decision point where suddenly something went from not working to working?

•What are all the criteria that have to be true to flip your decision? 

•What’s the situation in which this strategy wouldn’t be effective? 

•How do we figure out the context in which this situation would be true?

Song takes us through two popular frameworks as examples:

: “This made a ton of sense for Google, but that's because they were an incredibly metrics-driven company, where you could measure a millisecond in render time difference and translate that directly into company value. But if you're an early-stage startup and you're trying to figure out how to launch, that may not make a lot of sense — your metrics may not be very clear yet.”

: “This has been incredibly en vogue in Silicon Valley these days.

If you understand your customer base, it makes a ton of sense. But if you’re super early as a startup and you think, ‘I know what the customer looks like,’ you're probably lying to yourself,” he says. “In my opinion, it’s actually important to hedge and try to target different customer segments to see where the market pulls you. Otherwise you risk making your product overly centralized in the demographic that might not make a lot of sense for your business.”

No framework is perfect. Don’t just pick the latest trend off the shelf. The question is not so much, “How do we make this work at our company?” but rather “When does this 

Below, Song shares more about how early-stage startups can approach thinking outside the box, the companies that have inspired Persona’s strategy, and of course, how to figure out where it all might go south.

Lesson #4: Study other companies to source your inspiration.

“Culture can be a huge indicator of the business strategy and growth trajectory that you'll take. When you look in the Bay Area, I think 99% of companies out here are effectively cultural descendants of Google. When I was at Square, there were so many things that we did where our defense — implicitly or explicitly — would be, ‘Well, this is how they did at Google,’” he says. 

And it’s not just on the engineering side. “It’s everything from using OKRs to offering free food to structuring company benefits. Of course, Google is one of the most successful companies of all time. But this has enormous ramifications in terms of how your company will grow, the types of products that it's going to build and the kind of business model it will follow,” says Song.

“This Google-esque strategy can be amazing for building mono-product companies, but if you look at a lot of startups out here, there aren't many that’ve really been able to succeed beyond that — most have a flagship product with some sort of upsell type of motion to other types of products. But if you look outside the Valley, you’ll see companies with many different entry points into their business, and I think one key piece of this is because the cultures are really divergent.”

There's an incredible wealth of knowledge from other companies that didn't descend from the Google philosophy, but founders need to set aside the time to seek it out. “There's an enormous amount of value in exploring these alternative business models that aren’t well-trodden paths,” he says. Song shares a few that he’s been personally focused on learning from while building Persona:

“It’s a very multi-faceted platform and an incredibly complex system with so many different entry points and almost micro businesses. 

 talks a lot about how systems-based thinking is a huge part of everything that they do, that it's not so much about, ‘Oh, if we do this, then this will happen,’ but rather ‘If we do this, how is the entire system as a whole impacted?’” says Song. 

“The leap from causal-based thinking to systems-based thinking is very large. That's a really hard thing to build in culturally. 

As humans, we're often more wired to think about things procedurally. X causes Y causal things is just easier for us to work through. And as a result, we tend to think a lot more about the execution of something rather than the concept of it, or how the entire system works together

,” he says. “Lately we’re trying to think a lot more not just about the execution of a given framework, but rather how it plays in conjunction with all of the other kinds of frameworks, processes, and ways we make decisions at Persona.”

These days it’s less and less about what’s the right decision right now, and more about systems-based thinking. 

You have to make peace with the tradeoffs and the unknowns — or otherwise risk a serious case of heartburn. “You start seeing this push and pull of how you have to modify the entire equation of the company to still make this entire formula work out. What are the trade-offs I'm making? What would the evolution of this company look like two years down the line where we've really focused on this, but now we've become a bit weaker in this area?” says Song. “And any trade-offs that you make will actually emerge two years down the line.”

Just like engineering, when you build a company there are so many trade-offs that you have to make. There isn't a perfect formula. 

plenty of unconventional moves in Atalssian’s story — read our recent interview with former president Jay Simons

 for a more detailed accounting. Here’s what stands out to Song: “They built in Australia, they have dozens of products like Bitbucket, Bamboo, and Statuspage, all of which can be used independently of each other, and all of which are entry points into the entire Atlassian ecosystem. They launched a second product, Confluence, in just their second year, building their go-to-market and product innovation muscles early,” he says. 

“The inspiration here for us is where can we start spinning up second product lines? We have an initial product that seems to have found some traction and we're already trying to explore alternative products that would hopefully find their entire own entry points into the market,” says Song. “We’re trying to take a much more deliberate approach of constantly testing theories and re-evaluating if we are setting up a foundation for something that could eventually be large and gradually building our way towards finding that growth curve.”

Unsurprisingly, Song applies the pre-mortem technique to his own startup. “One of the greatest fears here is that we lose focus and stretch ourselves too thin. We might fail if we can't execute at the pace that we need to. Or if this idea of synergy between our different products isn't necessarily just sticky as we thought. Or if this culture is actually non-scalable and caps out at a hundred people,” he says.

But startups are a game of chance, of course — nothing’s guaranteed. “We have effectively traded market risk for execution risk. This decision to pursue a multi-product approach started with wanting to build a VC-backable business. For myself, I didn't feel this immense confidence that this idea and the market we’re in will suddenly become absolutely enormous. But I felt if we could create a culture where we can keep building new product lines and constantly launch new businesses, then it would be possible,” says Song.  “At the very least, I feel a little bit more comfortable with that trade because the market risk one just gave me way too much anxiety.”

This mindset was also more motivating on a personal level. “It felt like this strategy would create a culture that’s much larger than myself. It wasn't like ‘Rick has a brilliant idea and then this company went off and fulfilled it,’ but rather it became a company where many folks have amazing ideas.” 

My dream is that one day I walk in and I'm absolutely surprised by the things that we're working on and feel as if there was no way I could have ever come up with any of this.

“Microsoft has one of the most diversified revenue streams in the world. From Azure to Office, from individuals to enterprise, they’ve absolutely perfected what it means to build a platform where every product has its own go-to-market strategy. It's amazing how deeply coupled product and business are at Microsoft,” he says.

“How can we have people really focused on go-to-market from the earliest days? We have smaller teams of about five people, maybe three engineers, one designer, and one product manager. And 

everyone’s job is to think about go-to-market

,” says Song. “And it isn't just about upselling existing customers. It's about cold emailing people and trying to figure out whether this new product resonates with them 

 trying to sell them our verification product.”

As you spin up a second product, relentlessly emphasize go-to-market and spreading the knowledge of how to actually sell — don’t just hire an AE for that team and ask them to figure it out.

This isn’t the typical playbook in many startup orgs, but Song is a firm believer that everyone has to embody this go-to-market mindset. “Right now, I imagine that every single person on the team is incredibly tired of me telling them how important it is to understand go-to-market regardless of your role,” Song laughs. “That means engineers cold-emailing people, having some of the most uncomfortable conversations of their lives in the same way that Charles and I did when we were starting the company. It means having PMs think very hard about pricing, about what actually resonates.”

“Microsoft has clearly found a way to consistently execute on new product lines and sell them into existing customers. So you have to ask, why are other companies not able to replicate what they’ve done? What has not worked for others that has to work for Microsoft?” says Song. 

product and go-to-market have to be in lock-step

 to make sure the value proposition of what you're building has immense potential. But while at the early stages of a startup, product and business are literally joined by the hip, as the company scales, these two functions start to divide more and more — whereas at Microsoft, they clearly seem to be much more embedded,” he says. Another area this approach can go off the rails? “Think about prioritization problems and having your roadmap be overly dictated by sales or customer success.”

Lesson #5: Focus less on first principles, and more on how it all fits together.

Of course, borrowing inspiration from unorthodox models and trying new strategies on for size can go too far — taking every aspect of company building down to the studs of first principles would slow your progress considerably.

For Song, it’s less about reimagining everything yourself, but more about finding successful strategies that are overlooked. “

We're not trying to reinvent the wheel and find an entirely brand new strategy or cultural building approach that no one else has ever thought of

. Microsoft has been figuring this out over the last 40 years, the folks at Atlassian for more than a decade,” he says.

Ask Why It Won’t Work, And Other Lessons For Building From 0 to 1

From all the ways a candidate might fail, to how a commonly-used framework might not be a good fit, to where a go-to-market strategy might fall apart, Rick Song shares the pre-mortem technique he relies on, as well as other company building lessons from Square and his startup, Persona.

Persona's Rick Song shares the hiring and go-to-market lessons he's learned while building from 0 to 1.

Ask Why It Won’t Work, And Other Lessons for Building From 0 to 1

Hiring a VP of Engineering? Use This Framework from Shopify’s VPE to Get it Right

. He joined the company after the acquisition of Helpful.com, where he was co-founder and CTO. Previously, he was the VP of Engineering at Pivotal and Xtreme Labs.

When advising fast-growing startups, one of the most frequent questions I get asked is “How do I hire a VP of Engineering?” After more than 20 years, eight companies, and thousands of hires, I’m starting to suspect this may be the wrong question. A better one is, “

In 2018, a company I advise wanted to understand how their VP Engineering hire could be let go after only one quarter at the company. They had written up a thoughtful job description, sourced many candidates, and put the final ones through multiple rounds of interviewing prior to extending an offer — all for the new hire to last only three months in the role. What went wrong? It turned out that the company had a mistaken assumption about what they 

 in a VP Engineering. In this case, they hired a deep technology-focused leader when they needed an empathetic people leader to scale the organization. Luckily they figured that out quickly, and were able to pivot to another candidate who was a better fit.

But how do we help companies avoid this all-too-common churn? For me, it always comes back to defining what you’re looking for and what good looks like on a very granular level. Answering that will help you better understand how to find, hire, motivate, and grow folks into this role. You may find you don’t even need a VP of Engineering — many times, a team lead, manager, or director is what’s called for. (Even better than looking outside your four walls would be to promote someone internally to take this leadership role.)

First, consider what’s necessary at each level:

: An engineer with the capacity to guide others but who’s still primarily a sole contributor. Not just a high performer with seniority, but someone who helps others with their craft.

: An engineer with the capacity to lead others. Managers still contribute, but they also enable others to contribute. Managers focus on ensuring their team remains effective over time.

: A leader who manages multiple teams and managers. An empathetic person with a proclivity for systems thinking who has made mistakes and would make better choices in the future.

: A leader with a vision for how to build a highly effective engineering organization. Great ones know what work to hand off and are continuously motivating those beneath them in the style required.

Next, if a VP of Engineering is indeed what you’re after, I’ve found that candidates must be skilled in all three classic areas:

: Who’s involved and how are they motivated?

If you ask a technology leader how they would rank the above three skills from most important to least, you get a good sense of their skills and interests. But even more valuable is the chance to tease out whether their skills align with what you need right 

The order of these will change over time for both your company and the person. In early-stage companies, for example, you’re usually looking for someone to pair with a very technical co-founder or CTO to help define the early development process. As the company scales, the requirements change. You might now be looking for a more people-focused leader as the team grows in size and technical craft and career development comes into focus. A failure to adjust these profiles and fine-tune the hiring search is where most startups run aground in my experience.

A “right fit” in a VP of Engineering is partly a function of timing — their skills and interests must match the present need.

There is tons of content and advice out there around navigating this important hire, but few practical decision frameworks that help founders and technical leaders probe more deeply into what it is they’re looking for in a VP of Engineering. Over the years, the process-people-technology framing is one I’ve come to lean on and coach startups through. In this article, I’ll dive into each of these skill areas to discuss why they’re important, how to know whether they’re a priority for you at this stage, and how to recognize people who are a good fit for each. 

There are many different and successful people, styles, and processes that help you build effective engineering teams. There are no silver bullets. But hopefully this framework — along with some questions to ask in interviews and red flags to watch out for — will help you dive a few levels deeper into figuring out what type of leader you need to grow your company.

PROCESS: ASSESSING A CANDIDATE'S OPTIMIZATION SKILLS

A great engineering leader has opinions on a favored development process. This doesn’t necessarily mean they will force this process onto your company (well, maybe), but it’s good to have strong opinions and their own toolbox of process techniques to try out.

This need goes beyond just fine-tuning the development process, however. They also need tools for winning and keeping engineers’ trust. Back in 1968, 

 on how to motivate employees. Many of the lessons still resonate today. The most notable finding is that employees can become greatly dissatisfied based on company policy and how it’s administered. Good leaders must reduce this dissatisfaction, and it’s an especially urgent need in engineering.

Most engineers care deeply about optimization and suboptimal processes can drive them crazy.

Another danger for any technologist is to get so excited by technology and forget about why they are building in the first place. The customer matters, whether internal or external. A great leader knows how to run projects with short feedback cycles, as well as projects with very long ones. This means the customer may see value early and often (as with a feature update) or over a long-term horizon (as with a platform rewrite). 

Let’s dive into a few of these specific areas:

1. Experiments with the development process

I don’t believe there’s truly one correct way to write software. As such, every development team and environment can be different and still be successful. You only have to look at the debates around closed versus open offices or in-office versus remote work to see that there are many ways to win.

This means a strong leader must know whether to experiment with ideas like pair programming, daily standups, remote work, flex time, weekly retrospectives, frequent one-on-one’s, quarterly themes, and so on. Just because a technique worked in their last role, doesn’t mean it’s going to work at your company. 

Similar to how a product leader runs experiments with users in the product, an engineering leader on a growing team is running experiments in their domain: the development process

More specifically, a strong engineering leader knows 

 to try process improvements for the development team. For example, at Shopify we started experimenting with six-week development cycles in 2019, as a way to break our work into more manageable chunks, demo high-fidelity work and make better prioritization decisions. After experimenting with this in one team, it quickly grew to become the cadence for all of engineering and commercial teams company wide. 

Good process is like a traffic light. It may slow down the commute for a single driver, but it optimizes the system for everyone on the road.

Look for these qualities to find a strong experimenter: 

•Has shipped code with different development processes.

•Has examples of things that have failed but they’ll try again.

•Has strong opinions but is willing to change their mind.

Ask these questions to surface the best candidates:

•Describe the development process at your last company. What would you try again and why? What would you not try again and why not?

•What have you changed your mind about when it comes to the development process or engineering team practices?

Watch out for these red flags to avoid a mishire:

•Strong opinions, strongly held. Not reflective on their experience. If things didn’t work before, they would do the same thing again. 

•Has delivered software only using one development process.

It’s often overlooked how powerful a dissatisfier administrative tasks can be. Referring back to my favorite 1968 HBR article, the most powerful reason for employee dissatisfaction — company policy and administration — is almost as powerful a force as the top satisfier — achievement.

I keep this image as a favorite photo on my phone and refer to it often.

The best leaders can shield engineers from unnecessary admin and policy due to shitty systems like vacation tracking, getting their expenses paid on time, submitting resume referrals, or even helping to kill ineffective meetings (this one requires advanced skill).

A good leader will also find ways to be attuned to what’s bothering the team from a process standpoint. One way is via surveys (once the team gets large enough). 

You’ll be surprised what you can learn from a quarterly survey just asking simple questions like “What’s the worst part of your day?” or “What tool do you wish we used but don’t?”

Letting your engineers spend time working keeps them happy (technically, less dissatisfied). 

, VP Engineering at Twitter, suggests adding a question to your quarterly surveys on “time wasters” in your engineering organization and then having a crack team eliminate them.

Look for these qualities to find an unblocker:

•Unblocks all issues (not just engineering ones).

•Regularly identifies and destroys time wasters.

•History of high morale engineering orgs.

•Describe a shitty system at your last company. What did you do about it?

•On larger teams, how do you get a sense of what’s working and not working?

•Has a tolerance for sub-optimal systems. Doesn’t have a track record of making things better.

•Only focuses on engineering issues. Doesn’t broaden to fix organizational issues.

3. Focuses on continuously delivering value to the customer

Some of the best engineering leaders I’ve worked with want to interact with customers. This means they are always thinking about 

 to deliver value the customer can feel. Notice I didn’t say 

. This means they like to ship frequently to get feedback.

In tandem with a product and UX leader who wants to experiment with the product and how it works, an engineering leader should have a process cadence that allows the customer to give regular detailed feedback. A great process, without unnecessary back-office spinning (undue refactoring, long QA cycles, approvals, etc.) will let the customer see the product often and give a steady stream of comments on the order of days or weeks, not months.

 they understand what the customer wants. It’s really important to realize that the customer owns the problem, but that you can own the solution. Keeping these two ownership circles distinct, allows two great processes to happen separately. Firstly, the customer can vividly articulate their needs without “solutioning” too early. And then, the technology team can dream up and test amazing prototype solutions to their problems. Win-win.

Look for these qualities to find a champion of the customer:

•Knows which projects are appropriate for a fast feedback cadence.

•Says things like “This will take three weeks, but if we make this change we can test in two days.”

•Let’s the customer own the problem, but takes ownership of the solution.

•How would you get feedback on a platform rewrite?

•How do you handle customer feature requests?

•Describe a time where you felt your team wasn't shipping frequently enough. What did you do about it?

•Works with very long feedback cycles and is unable to figure out how to get feedback more quickly.

•Triages and implements customer feature requests, instead of understanding the customer problem.

PEOPLE: ASSESSING A CANDIDATE'S TEAM BUILDING CHOPS

I don’t think it’s an overstatement to say that “people” are the most important tool in the engineering leader’s toolbox. However, at different inflection points in a company’s growth, people concerns can become either more or less important as their primary focus.

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