Know Thyself: The Quest for a Head of Product

Having spent much of my working life leading product teams, before switching to the VC side of the table, I am often asked what makes a good Head of Product (HoP) or Product Manager (PM)?

carter
carter
Jul 25, 2018 · 11 min read

That question is usually followed up by what they really want to know: ‘Where does one find these mythical humans?’

If you’d like more analysis and insight like this, delivered monthly(ish) to your inbox, sign up to The Operator’s Manual (our newsletter) here.

The truth is it’s still incredibly hard to unearth these individuals in large part because there’s still no industry-wide consensus on what this role encompasses, (indeed it can vary from company to company). There are many reasons for this:

The HoP/PM role, itself, has evolved over time and is still loosely defined — Many tech workers are now interdisciplinary, which means designers can code, and engineers design, etc. Production tools and release cycles have gone from the Dark Ages (basically throwing specs over a wall and praying), to tight daily releases and two-week sprints, while spec’ing features is now often done by designers directly in Sketch or Figma (vs. pages and pages of descriptive text and wireframes). So a lot of the more administrative aspects to product management have, thankfully, gone away.

An ideal HoP fit varies depending on the ‘product’ the company in question is building, as well as the company’s stage — a Seed-stage job listing company, for instance, will need a different type of HoP to a B-stage mobile gaming company… or say, a Warby Parker… and so and on.

An ideal HoP fit depends on the existing strengths and weaknesses of a founder and their team — A strong bench of technical co-founders probably need someone with an equally strong sense of business and UX. Meanwhile, a founder with strong sales, brand, or marketing acumen likely requires someone with the equivalent technical background, as well as a conviction of what will resonate with the business’ target consumers. This principle is true for a lot of leadership roles, but Product is often the glue that brings these disparate functions together.

A lot of the best HoPs go off to start their own companies — the original Head of Product (and holder of the company’s vision) is ultimately always the founder(s)/CEO. Because the HoP is the person who helps actualize and execute a founder’s vision, I’ve come to think of their role as being closest to a DP/DoP in Film or a Producer in Music, which is why the best ones either stay with their ‘directors’ or evolve to ‘directing their own movies’ at some point. So there’s a scarcity factor at play as well, which will hopefully be somewhat mitigated by initiatives such AWIP’s (Advancing Women in Product) to open up the product management field to more women, who have to date been shamefully underrepresented.

Hard skills & buyer’s remorse.

Should HoPs have CS degrees? MBAs? Design backgrounds? Are the best of them former founders themselves? I can think of great examples from each of these cohorts. So I don’t think there are actually any hard and fast rules here. But Product people do need to have a sense of what they are asking for, and generally that requires some experience in (or knowledge of) either engineering or design.

Unlike interviewing engineers or salespeople — it’s really difficult to objectively and quantitatively evaluate HoP candidates’ ‘hard skills’, which results in a great deal of buyer’s remorse, primarily around the failure of new hires to get down into the weeds, do wireframes and specs, properly analyze and present data-driven cases and execute.

This is exacerbated when a HoP candidate has been in a role for a while and looks great on paper, but because they have been in ‘senior management’, far removed from the daily grind, they have either ‘forgotten’ or are less willing to get their hands dirty. I had an experience with a HoP hire who — despite an outstanding resume as a designer — flat out couldn’t launch a product.

(Screening for this is tough, by the way. In an interview, I tend to ask about what their typical day at the office involves. If they say: ‘I get in and answer some emails, do some meetings, and so on…’ you already know that person is a non-starter. When you’re trying to build and launch a product, you need to be wire-framing, looking at the data, writing specs and so on, rather than firing off emails and ‘managing’ people.)

For those of you who haven’t read it yet, I highly recommend Ken Norton’s seminal primer on “How to Hire a Product Manager” to help you evaluate some of the ‘hard skills’ required for this role. However, I do believe that there are some ‘soft skill’ commonalities among all great product leads:

1) Expertise in Communication and Diplomacy

The HoP is often both the bearer of bad news and the broker of peace.

“I know we’ve flip-flopped on this feature a thousand times, but we need to build it this way now…”

“I know we said that we would have an internal beta by this week, but the team discovered some errors in auth that need to be dealt with before we go live…”

“Yes it’s important for the business to be able to do X by next week, but Y is just way more important right now…”

The product lead is a person who must communicate effectively and regularly across so many different disciplines, and they need be masterful at it. It’s been said many times before, but emotional intelligence/EQ is critical. This individual needs to be able to gain respect with each team and maintain that respect and trust over time — no easy feat when dates, scope, and priorities inevitably shift, as tensions bubble over.

Engineering and design, for example, yearn for stability, while the rest of the business demands the agility to shift course quickly to react to the ever-changing market. Even though data is the most persuasive mediator between both of those sides — and if something’s not working it’s very clear from the data that that’s the case — the HoP needs a diplomat’s deftness to act as a stable and rational fulcrum between these two opposing forces. And they must be able to negotiate and regulate peace between them, which can only be achieved with a deep understanding of each team’s perspective.

2) Human-Centered Design and a Detail-Oriented Mindset

Sometimes the most meaningful impact comes from really minor and mundane product changes, and these are almost always picked up by talking to your users. The HoP must be able to study, interpret, synthesize and translate what the data reads and what the users say into product alterations — and prioritize accordingly.

Because they sit in the middle of engineering and design, the best HoPs will be cross-disciplinary, both steeped in design/UX and able to code. The reason this matters is that the product lead needs a thorough understanding of what he/she is asking of their team. In my experience, when stuff breaks down it’s invariably because the CEO/founder/Head of Sales is asking for something unrealistic and the HoP doesn’t push back. If you don’t know what you’re asking your team to do and the level of work and complexity it involves — and ‘just’ ripping something out will potentially destabilize the company’s core architecture — then tempers (and products) soon fray.

The best and most knowledgeable product leads will back up requests with a reasonable, rational explanation of why they think something will work/or why consumers are asking for it, or will need it. Just asking for a bunch of crazy shit to be done not only takes focus away from the core business and product — but results in a loss of personal respect.

Sweating the small stuff

Similarly, when VoIP was in its infancy, design choices — alongside free calling — was what helped put Skype so far ahead of its rivals at the time. We also took an enormous amount of time to design video for Skype. I remember countless meetings with [co-founders] Niklas and Janus, where we were sweating every single detail. Sometimes they would call at the weekends to badger me about, say, the setting menus or the consistency of the fonts within — such was their determination to get the design spot on. The reason, of course, is that this stuff matters. If the product doesn’t feel cohesive, then it’s a broken user experience. We took a lot of time arguing over seemingly obscure design choices for the video feature — and the result was worth the wait.

So I cannot overemphasize the importance of a strong design bench: products live and die by it. Oftentimes companies attempt to wing it with one or two junior designers and that path leads to certain doom. With a strong design cohort, products — including those which are exclusively b2b — become worthy of being beloved by their users.

In the same vein, details are similarly make-or-break. Attention to detail enforces design and brand consistency across the product, resulting in a stronger brand and more intuitive experience. Attention to detail increases effectiveness of marketing copy, as it relates to conversion and retention. Thoughtful and detailed empty states, error messages and considerations for edge cases produce superior products that users can feel. Even thoughtful, clever or amusing error messages on developer-facing portions of products can turn developers into your strongest advocates. A good HoP invests in and takes responsibility for details, and ensures that it all makes sense and works, and any changes are successfully communicated between teams.

3) Curiosity and Intelligence

Curiosity and intelligence go hand-in-hand by definition. I love seeing weird, circuitous backgrounds in people — so as long as there’s some rational narrative behind it. It tells me that they are curious and therefore likely intelligent.

The thing that has always excited me the most about building products and businesses (and now evaluating them on the VC side) is being dropped into a realm of business that I know absolutely nothing about and suddenly having to make my way back to basecamp. I knew nothing about music streaming businesses, preventative healthcare, instant messaging or local online directories, but I loved diving into these vastly disparate areas to better understand them so I could isolate a core problem and devise an appropriate product solution.

So it’s not always important to have previous experience in the domain of the business in question. Someone new to the field, who has done their research and comes fearlessly with well thought-out opinions on product challenges, how they might be approached, and a feel for the competitive landscape is often more valuable that a field veteran. The type of questions that they ask about the space and the business will speak to their level of curiosity and hint at their intelligence.

Speaking of intelligence, the candidate’s intelligence should frighten you. Of all the aphorisms about hiring, the one about only hiring people who are smarter than you could not be more true. Every interaction with this person should make you think to yourself:

“Why on earth would this person report to me?”

4) Vision and Tenacity (and Speed)

“If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea.”- Antoine de Saint-Exupery

Finally, vision. In addition to being able understand the complexities of a particular business and of building and designing a product around it, this person needs to be able to have — and clearly communicate — a long-term vision.

HoPs must be able to take products into realistic new directions that others simply aren’t able to see. In the worst cases these visions make sense and are attainable. In the best cases, they excite people both within and outside the company.

(It’s worth adding a caveat here that vision is earned over time and the founders and CEO are the rightful holders of the company’s vision. Then at some point, once trust has been steadily accrued, the HoP gets to share their vision too.)

It’s also worth noting that vision alone is not enough. It takes incredible tenacity to translate a vision into a product, see that product to market and maintain both product quality and team morale in the process. Tenacity — alongside speed — are the most important factors in the delivery of a vision. No matter what type of product lead you are, if the production process doesn’t go fast, the business eventually dies. And that’s true of any vertical/sector.

So you need someone who is going to drive the momentum of the teams (at least the ones building product) and hold people accountable for missed deadlines. In other words, you need someone to run the trains. Someone who people rally round and respect.

A word on due diligence

When it comes to post-interview reference checks, the first hop out (i.e. named referees) will almost never give the candidate in question a bad review. In my experience, the worst they will say is ‘X needs to develop in area Y’. The second hop out is where you’ll hit pay-dirt. That’s where you have to do a little digging (LinkedIn is your friend here) and find a mutual acquaintance who has managed (ideally) or worked with them. They tend to be a lot more candid.

When you meet the candidate — let’s be honest — you can generally tell in the first 30 seconds–to-two minutes whether that person is going to be a fit for your company. You can run as many filters as you like, and ask probing questions for hours on end, but as with any interview, your decision will ultimately come down to a gut feeling you have within seconds of meeting them. Chemistry dictates that you need to want to work with this person, no matter how dazzlingly brilliant they are. I’ve hired difficult people before, because they’ve been brilliant, and it’s never worked out. You need to get along. Especially in this role.

***

There are, of course, many others things to look for when hunting the Head of Product, however if you are able to Know Thyself — to look inward and truthfully identify your company’s strengths and weaknesses — you’re off to a great start. If you find a candidate who can both complement these qualities and meet the criteria above, you’re in an excellent place.

And by the way, if you do come across any of these mythical humans…please send them my way.

*Carter Adamson is a Venture Partner at Atomico and Head of Product at Betaworks Studios.

Carter has worked for a number of different companies at all stages of their development. He co-founded the online music service Rdio and Sum, a health and wellness wearable startup. He was head of product at Skype, a senior product manager at ICQ and AOL.

Startup Grind

The life, work, and tactics of entrepreneurs around the world. Welcoming submissions on technology trends, product design, growth strategies, and venture investing. Learn more about how you can get involved at startupgrind.com.

carter

Written by

carter

Carter Adamson is a Venture Partner at Atomico and Head of Product at Betaworks Studios.

Startup Grind

The life, work, and tactics of entrepreneurs around the world. Welcoming submissions on technology trends, product design, growth strategies, and venture investing. Learn more about how you can get involved at startupgrind.com.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade