A Comprehensive Guide To Navigating Product Leadership During COVID-19

Alex Schiff
The Startup
Published in
19 min readApr 21, 2020

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There is no other way to say it: the world was flipped on its head during Q1. Everywhere. As far as I’ve seen, there are very few industries or positions that weren’t meaningfully upended both directly by COVID-19 (shelter-in-place orders, supply chain issues, etc) or by the ensuing economic fall-out (plummeting sales).

This essay will attempt to provide some concrete, tactical advice based on what I’ve seen work and not work managing teams through this crisis, and it draws on both personal experience at Occipital (leading Canvas) as well as advice I’ve seen from others that has resonated with me (particular credit goes to Reforge’s Growth In Turbulent Times series).

The first section is, I think, broadly applicable, but the second will focus on B2B products (as that’s what I am in the headspace of worrying about right now).

Managing your team

Embrace the fact that for the foreseeable future, you are a remote team.

We are, I believe, going to be in a remote-primary environment for longer than people realize. I am telling my teams to be prepared to do this through 2020.

People are going to refuse to accept this reality just like they are refusing to accept the necessity of shelter-in-place today. But for companies in technology, law, accounting, and pretty much any industry that isn’t dependent on physical equipment or infrastructure, dig in for the long haul.

First, social distancing isn’t just going to go away entirely when shelter-in-place is lifted — we are, I hope, going to tell people it’s okay to go see their friends and family in small (<5-person) gatherings before we send people back to work en masse.

Second, certain sectors will come back to work first, and they will be prioritized based on 1) need to be physically present at a location to do the job, 2) ability to perform the job with appropriate distancing, and 3) economic pain that industry is experiencing. Technology companies — at least the ones that aren’t working on hardware, cars, or other physical goods — are going to be at the bottom of that list.

Finally, if you aren’t working on physical goods or it’s not otherwise severely inhibiting to work from home, it’s frankly just your responsibility to tell people to work from home if they can until we are out of the weeds on this. Do your part and stay the fuck at home.

This may feel disruptive, but remote work has been an increasing trend for years:

That means that this is not a new problem (whether you agree with it or not), and you should take advantage of all of the great content out there. This guide from Zapier is the most comprehensive set of content I’ve come across. But there is a ton out there.

Note: If you were previously collaborating across multiple offices, congratulations! You have an advantage: you are already accustomed to doing your job without being co-located with your team. Lean into that, because there are a whole lot of people (including your competitors!) that have never had to do this.

Increase the frequency of your communication.

This is the most common advice I’ve seen, and the most obvious. For anyone you directly manage, make sure you are engaging with them at least once a day. And for people you indirectly manage (i.e., you manage an engineering manager who manages that engineer), try to make your presence known to that person at least once a day by engaging in Slack conversations, listening in on scrum huddles, etc. Or just say hi and see how they’re doing.

This may seem hilariously simple for people that work directly with one cohesive group that run daily stand-ups, but if you work with larger or more fluid groups, your main daily interaction might be informal water-cooler conversation. In a fully remote world, people can feel disengaged very quickly in the absence of feedback, so go out of your way to have daily touch points.

Ensure no one is ”management orphaned.”

If you are like most companies dealing with COVID-19, there have probably been layoffs at your company. That might mean someone’s manager was let go, and there isn’t a clear person they are supposed to go to for direction or help.

If you notice this, make yourself that person, or broach the topic with the best candidate. Don’t let it sit, or be afraid you’re over-stepping your lane. You may not be the best person to manage them or direct their priorities (or just may not have time to manage them well), but as a product leader, you are likely to be fairly in touch with changing product priorities, so you can at least make some informed suggestions vs. that person guessing in a vacuum.

This comes with responsibility. If you do a tolerable enough job, it’s no longer a screeching problem, and it becomes low priority for others to address it. It also means that you now become the source of blame for someone working on something that someone else disagrees with, even when you’re basically just guessing yourself. This is why it’s important to: 1) defend your assumptions, but don’t try to pretend like something was an informed decision if it was a guess to try to keep them busy, and 2) flag to your leadership team if you are taking responsibility for someone’s work, and clearly state your concerns in doing so.

It might suck to take on extra responsibility right now, especially if you aren’t very comfortable with the area that person is working on, but it could make a difference in that person being laid off if things get worse (as higher-ups may determine that someone is simply “spinning their wheels” and not being utilized). It’s also an opportunity for you to step up within the company, learn new skills, and make yourself essential.

Finally, if you have been management-orphaned, raise your hand to someone in leadership. You’d be amazed at how often people don’t realize who was managing who if it wasn’t them.

Be honest without being gloomy.

This is also not novel advice, but it’s important — especially because right now, everyone is gloomy (with good reason!). Your team will see through bullshit. They read the news, and their friends are getting laid off. If the numbers look catastrophic, state them honestly — and what you’re doing about it. If you’re asked if you’re about to do layoffs, don’t reply “Oh god I don’t see how we can’t,” but communicate if it’s a possibility (and how you’re trying to do what you can to prevent it).

Take a look at President Trump talking about coronavirus vs. New York Governor Andrew Cuomo:

Who seems more credible right now? If your interests (physical, economic, or otherwise) are on the line, who are you going to listen to? The person who is telling you like it is, that’s who. Not lying about bad news, even when it’s scary, is how you win the trust of your team. If you don’t have the trust of your team, they are definitely worried about getting laid off, and are either a) not being productive due to anxiety or b) looking for another job.

Remember: careers are long story arcs. You’re likely to run into people you lay off again — and you might be on the other side of the equation. People (usually) won’t hold a grudge that you couldn’t afford to keep them if the money just isn’t there, but they almost always will hold a grudge if you were dishonest about it.

And they definitely will if you do anything like this.

On calls, avoid the temptation to jump right in to work.

This one is easy. When you get on a scheduled call, just ask how the other side is doing — and ask genuinely. Nothing is worse than feeling like someone is asking how you feel because they’re supposed to or they read it in a Medium post. Similarly, very little is more uplifting than knowing someone outside of your immediately family actually cares about your well-being. Listen, even if it means the call takes a little longer. Where else do you have to be?

Be conscientious of the fact that everyone’s situation is different. The best case scenario is “distracting.”

The reality is that even though we’re all stuck at home, we are living wildly different realities. I’m living with a close friend (who I have previously lived with) and his girlfriend, which means that my primary conflict during the day is that I smoke up the kitchen when cooking salmon. Your co-worker might be responsible for keeping their kids engaged with remote learning — or simply from lighting their house on fire. They may be running around caring for an elderly parent whose caretaker can’t visit them anymore. They might be living with someone they have a strained relationship with — or worse, someone who is outright abusive. You just don’t know.

And that’s just in your own country. If you have coworkers in another country, there may be pre-existing issues you’re not aware of that might make this even more disruptive. Their health care system may have been starting from an overwhelmed state, so they may be legitimately terrified about a loved one. They may have significant issues with Internet bandwidth in their homes, or even lose power — regularly, before the crisis. You just never saw it because they paid a small fortune for their office Internet or had a generator.

Just be aware and be understanding. If a project is delayed, you’re going to survive, and people may be dealing with matters of literal life and death right now. You may not even know, as, for better or worse, many cultures are not as forthcoming about personal problems as Americans.

Managing up & across

Report data early, report it often, and state the unknowns.

As a product leader, you’re likely the expert on what’s happening in the product or area you oversee. 90%+ of your colleagues, to be frank, won’t know which metrics they even should be looking at to assess true damage. In an early-stage company, the data is often so naturally spikey looking at a chart, it will just generate more questions than answers without a narrative anyway. You also need to be looking at both leading and lagging indicators, and understand the complete picture of how local regulations and headwinds will affect these numbers.

I’ll use the product I manage, Canvas (where we power home improvement companies 3D mapping spaces), as an example.

This is a chart of our weekly volume of scans uploaded to our Scan To CAD service, which is the current primary key metric for that product:

The most basic reading of this chart is that shelter-in-place killed our volume, which makes sense because 1) people can’t visit homes to scan them, and most home improvement projects were put on hold, and 2) these orders came in on a rolling basis. So, it follows that when these orders are alleviated, volume will rebound.

However, people need to buy our hardware (for now) in order to scan spaces. Hardware sales fell off a cliff in mid-February:

Hardware sales are not the KPI for Canvas, so if you’re on the outside looking in it would be easy to ignore it. However, hardware sales are a leading indicator for volume (because it means new customers), and they started dropping hard in mid-February as the gravity of the pandemic started to come into full view.

What else might support that this was an early sign of economic headwinds?

SPDR S&P 500 ETF Trust (SPY) Chart via Yahoo! Finance

This was an early indicator (and it’s just that — an indicator, not a conclusion) that we were starting to face headwinds on customer acquisition— over a month before jobless claims started dominating headlines. As a result, we shifted our planning to prepare for a recessionary 2020 immediately when volume began to dip, which was far earlier than most.

You can see from these charts that the data I had to report was fucking miserable — and the only reason I even feel comfortable sharing them is because I know they probably look a lot like yours. But I reported them early, to more people than I usually do, and in each report I tried to put it in context as best I could. Perhaps more importantly, I stated when I didn’t have a concrete answer:

This is how you build confidence from above and across. No one is expecting product performance to be good right now. That’s not an excuse; it’s just the reality of a combined health + economic crisis (unless you are Amazon, DoorDash, Zoom, or similarly “positively” impacted). But you have to make sure people are informed — it buys you trust and autonomy to make decisions, but, more critically, it ensures decisions aren’t made about your area based on an incorrect understanding of what’s really happening.

Be proactive, and start the conversation.

This goes hand in hand with the above, but if you have data demonstrating you need to make changes, don’t wait for other people to tell you to do it. Flag what you’re doing so others can weigh in if they have an opinion, but chances are, they’re looking for you to come up with a plan. That’s why you’re in the position you’re in.

(In our case, that meant doubling down on accelerating our recently teased phone-only 3D capture tech. If you need to measure, document, or otherwise capture data about spaces you can’t visit right now, let’s talk!)

If you can’t execute changes on your own, make a proposal. Start the conversation. Don’t let inertia or fear win. Whatever you do, make sure the leaders above you know that you’re their partner to enact change. Otherwise, you won’t be in the room when decisions get made.

Check politics at the door.

Now is not the time to be pissing around for influence. Communicate what you need from other people clearly, communicate your blockers, and don’t be taken advantage of. More than ever, though, your personal success depends on collective success.

Also, life is hard enough right now! Try making it easy for other people for a change.

Business

Many of your customers are about to go bust.

This is a sad, sad reality, but if the looming recession is as bad as people think it will be, many small businesses simply aren’t going to survive. To quote an analysis in the Washington Examiner:

Roughly 170,000 small businesses closed between 2008 and 2010. Over the last three months, 630,000 retailers have either permanently or temporarily closed their doors. Meanwhile, 1 in 4 small businesses say they are less than eight weeks away from closing permanently, according to polling by the U.S. Chamber of Commerce.

If your revenue is concentrated among small businesses, it’s going to be a long winter. So, what do you do?

  • Your absolute first priority is revenue preservation — be flexible to avoid churn. This might mean delaying payments, restructuring roll-out timelines, or swapping customers out for a different product offering that is more conducive to the current times. It’s tempting to force customers to commit to paying out their current contract when you’re hurting for revenue, you’ll buy their loyalty (for a long time) by engaging them proactively to make sure your relationship is mutually beneficial. In an environment where most current revenue is at risk and most new revenue will be a heinously uphill battle, this is, reluctantly, the best thing you can do for your cash position. You’re playing for the long-game.
  • Build a model where your smaller customers go bankrupt, and act accordingly. What happens if the smallest 20% of your customers all die? What happens if that number is 40%? What that means (and how likely this is) varies wildly from business to business, but know the answer and plan for it.
  • Focus the majority of your revenue preservation efforts on your biggest customers. You should be doing one-on-one calls with all of your top customers. Frequently. First, you need to understand how the crisis is going to affect their business — both to understand how to support them as a partner, but also to inform your thesis on how to approach the broader market. Then, you need to ensure you’re doing absolutely everything you can to preserve their business. This doesn’t mean ignore your smaller customers, but you need to prioritize your time on what is likely to preserve the highest absolute dollar-values. Now is not the time to worry about being over-concentrated.
  • Focus your growth efforts up-market. Yes, as you focus on large companies, sales cycles elongate, and incoming cash becomes further off. But bigger companies are going to be most likely to weather this and have cash to spend, alone invest in the future. I’d rather deal with a longer sales cycle than chasing companies whose primary concern is surviving the next 30 days. Besides, for the next 12 months, all sales cycles are going to be long, so you might as well make it worthwhile.
  • Cut costs with lead times proactively. Many of your most expensive costs have a termination period, so you can’t just flip them off. If you can avoid cutting those costs until you get more data, great, but most companies don’t have the luxury of holding on to big costs for 30, 60, or 90 days if the revenue that supported it dried up. Pick the version of the future you think is most likely, cut accordingly, and bank on the fact that vendors will be thrilled if you withdraw the termination at the 11th hour.

Recession-proof your spend.

The surface-level advice I often hear is “cut every non-essential expense.” Some — perhaps most—of those reading this may have no choice. However, recessions are also when the strong create distance from the weak. They do this by acquiring the best talent on the market, and investing in growth and seizing share when no one else can.

Every company is different, so the only advice I will offer is to think holistically about how you cut.

  • We have to cut all our SaaS subscriptions! We can’t afford time-savers, and every penny counts! Really? They probably add up to <1% of your annual spend, and cutting them might make life really shitty (and hurt productivity) for the people you’re depending on to save the day.
  • We can’t possibly make that hire! Ignoring the fact that not making the hire means you might have your most expensive staff doing low-value work (or that you might demoralize them), it might mean you simply won’t achieve the goals you need to hit to reach your next funding milestone. Then you’re dead, and all of this is for naught.
  • We can’t let the senior leader go— they make sure we are working on the right things! And they are the most experienced hands we have! Do you think people just sit on their hands if they don’t have a boss? In many organizations, your top-paid staff do the least in terms of actually keeping the ship running. Laying off junior staff can leave a vacuum in operations that creates a downward spiral.
  • We can’t possible invest in that right now! Sure, take a fresh look at all your expenses and make sure the thesis holds true in the new normal. But don’t just stop investing in growth. If you have the cash, now is when you seize share when your competitors are quiet (or dying).

Product

Quarantine-proof your product.

The world is on quarantine. More importantly, it will be on various forms of quarantine for some period of time. Probably not all of the next 18 months, and not as restrictive as right now, but it may be for larger parts of that time and more disruptive than we care to admit — setting aside the lasting psychological impact. So, how do you quarantine-proof your product? Ask yourself these questions, and then make changes until you can answer “No” to as many of them as possible:

  • Do any parts of the product experience depend on visiting a specific location?
  • Do any parts of the product experience depend on people being physically co-located?
  • Are any parts of the product experience impeded by wearing masks, gloves, etc?
  • Do any components for the product depend on international supply chains?
  • Do you rely on in-person meetings for sales, onboarding, or retention?
  • Do any triggers depend on travel, movements, site visits, in-person interaction, etc? (Don’t overlook this. A podcast-listening app, for example, may not depend on travel for usage, but one of its primary triggers is likely commuting.)
  • Do any customer segments depend overwhelmingly on travel, events, bars and restaurants, or other public gatherings?

Prepare your product for a world in which public gatherings are put off for 6–12 months, in-person interaction is highly restricted, and movement of goods and people is vulnerable to shock. That might mean:

  • Reassessing your target inventory levels for physical products (to make them more resilient in case of disruption)
  • Finding local vendor back-ups for components and materials
  • Reassessing the shipping experience (what if people don’t have a business address to send to?)
  • Auditing your product and website’s susceptibility to poor Internet connections
  • Adding collaboration features to the product experience
  • Integrating with collaboration and remote work tools like Slack and Zoom
  • Auditing all aspects of interaction with other humans within your customer journey in a remote context
  • Reassessing the viability of any and all events (including trainings and onboardings) as being done through Zoom, CrowdCast, and streaming platforms and either reorienting or pivoting accordingly.
  • Reassessing (and likely cutting) all outdoor and in-person customer acquisition strategies
  • For the love of God, make sure you have COVID-proofed your messaging.

This is an abbreviated list to get you thinking. Don’t defer this because it seems like the country might open back up in May. Pandemics, like the 1918 pandemic, often happen in waves:

Source: https://www.cdc.gov/flu/pandemic-resources/1918-commemoration/three-waves.htm

Try to make these “and’s” and not “or’s” in your product and business. We don’t know how this virus is going to evolve post-Q2, so this is about disaster-proofing, not destroying, your existing business in a very uncertain time. You should be planning in weeks, not quarters where possible — no one knows what the world is going to look like in Q3/Q4.

(Unless your business depends on crowded in-person gatherings — then you should probably hunker down for a very long and very brutal 12–24 months.)

These are also opportunities, as your customers are all trying to figure out how to operate remotely as well.

  • Can you provide them tools to engage with their customers remotely in ways that weren’t possible before?
  • Can you help them maximize digital channels that were previously an afterthought?
  • Can you provide them access to an audience that they couldn’t reach before?

As always, the best way to explore these questions is to talk to your customers. Get on the phone (or Zoom) and ask broad, open-ended questions. Are they totally frozen, or is their demand being pushed into a new channel? How are they expecting the next 6–12 months to go? Are they entering hibernation, or trying to seize the moment to do something new and innovative? Are they sitting on their hands, or feeling pressure?

This is the time to get creative! Saturday Night Live produced a show entirely from home. MLB is talking about sequestering everyone in Arizona to play a season with no fans. Most of these experiments will suck, but what do you have to lose?

Recession-proof your product.

This is the literal only chart that matters for this discussion:

And this is just March — as of this writing, we’re already over 22,000,000 jobless. We likely already have the highest unemployment rate since the Great Depression, and the St. Louis Federal Reserve projects hitting 32% (far worse than any year recorded in the United States).

Some jobs will come back quickly as shelter-in-place orders are lifted, but we are in for a long period of social distancing that will make some of those losses permanent. The average business keeps 27 days worth of cash on hand, so many businesses have already gone under. Suffice it to say, there’s going to be a lot of economic pain in the year ahead.

I have told my team to be prepared for a totally frozen Q2, a very, very bad recession through 2020 and a modest recovery starting in 2021.

So, how do you recession-proof your product?

  • Audit your customer segments and score them based on vulnerability to recession. This report is a start, but you probably need to get much, much more granular (as it’s usually impractical to wholesale switch industries). Do any of your segments have government contracts? Do any of them operate on more predictable schedules vs. being driven by consumer behavior? Do any of them have multi-year contracts with their customers? Ask yourself what tweaks you could make to appeal to segments that are less correlated with the economy. That “kind of interesting” niche you’ve been ignoring may just be the diamond in the rough to focus on right now.
  • Target larger customers who, while hurt, are unlikely to die. This means slow sales cycles (especially now), and slow sales cycles could mean cash flow problems — but that is a better problem to deal with than all of your customers being bankrupt. Focus on securing small, beachhead deals with clear and immediate ROIs. Don’t bother pushing the big multi-year deal right now. This might mean changes to your website and purchase funnel to cater to this kind of buyer, getting more hands-on with sales conversations (if you’re used to a hands-off eCommerce flow), or building out more enterprise-friendly features like permissions and dashboards.
  • Given lengthening sales cycles, you may want to consider using this as an opportunity to sell and market ahead of engineering. With, say, a 6 month lead time, you have plenty of room to test demand for certain features and products and wait for buyers before committing resources.
  • Ask yourself how you fit into existing budgets, not new spend. This is good product management and sales acumen in general, but critical as buyers pull back spending.
  • If you have the cash, prioritize discounting and pricing strategies that lock in customers for longer periods of time at the expense of generating upfront cash. Even consider buying out competitors’ contracts — a very clever idea I heard on Reforge’s Growth In Turbulent Times: B2B Edition.
  • Lean into features that enhance direct cost-savings and direct revenue-generation for your customers. This is what is going to motivate people right now, not time-savings or efficiency. Amidst layoffs, businesses are not prioritizing convenience and time-savings — it’s about hard $$$.

Above all, the most important question to be asking is the same question you should always be asking: am I a vitamin or a pain-killer?

You better figure out how to be a pain-killer.

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Alex Schiff
The Startup

Product @Square. Prior: built Canvas @occipital, co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily.