I’m a big believer in developing heuristics over the course of your life. These are rules of thumb you internalize so that you don’t have to re-invent the wheel the next time you do something similar.

An example would be doing 30 minutes of any physical activity 3 times a week to stay healthy. You don’t think about whether it’s cardio or weight lifting, whether it’s high intensity or low, you just simplify it to “move my ass 3 times a week = I’m staying healthy”. The thing about heuristics is that they aren’t always optimal, but the efficiency gains you harness over time from quick decision making more than make up it.

I’ve found that between important life transitions, conscious effort to synthesize the heuristics I’ve developed helps me accelerate my little cheat sheet to life. Now is one of those times, as I’ve recently moved to work at Shopify.

Before that, I spent enriching years as a Director of Product Management at FreshBooks. The role was more akin to the traditional “group product manager”, which entails leading a group of product teams and driving the execution. By the time I left, the group was about 40 people across 5 teams, spanning all the payments, partnership, and mobile products at FreshBooks. It was basically a small company within a larger one, and I consider it the greatest management challenge I’ve faced to date.

After a month to consolidate my thoughts on the experience, here are the heuristics I’ve formed to help guide me in the future.

1. With strategy, be a broken record

One of the things you have to do as a director is constantly get up in front of the team to inspire them against a product vision and ensure they’re aligned with the strategy so everyone moves in the same direction. It usually goes something like this:

“People hate [problem]. Our team exists to create [service that solves problem] and make it accessible to [large group]. We will achieve this by [doing this and this] which makes sense because [rationale]. We will measure success by [metric that matters].”

It’s human nature to feel ridiculous saying the SAME DAMN THING every week, especially with the same oomph every time. But you must realize that as it’s creator, you live and breathe this strategy and therefore it feels redundant and obvious to you. To others, it continues to stay novel well beyond the first time they hear it.

Hearing something and internalizing it are two very different things.

Remember that there’s a lot of noise competing for people’s attention, and it’s likely you have many people simply not listening at the moment, or just plain forgetting the strategy despite your repetition.

A single person off strategy can derail a team. It is worth feeling redundant in order to optimize for 100% alignment with the team.

2. Ask the right questions, then live with any failures from the team

It’s almost cliche to ‘let your people fail’, but in practice it’s hard to do when your ass is on the line as is always the case as a director. When you see it missteps happening in front of your eyes, it isn’t easy to hold your tongue.

Your tendency will always be to correct mistakes as they happen, but that ends up stifling the team’s sense of ownership, and develops a terrible creative dynamic whereby the team is trying to please a single person instead of work the problem.

You also can’t do nothing. So the heuristic here is to exert your influence by asking questions throughout the creative process. You’re in a perfect position to take several steps back from the weeds, and ask the team the basics of why the customer cares about this and why their approach is correct. Stimulate the conversation but don’t direct it towards any particular conclusion. Let the team digest and incorporate those questions into their thinking, and then just live with the consequences.

If the team fails, the only thing you must do is to make sure there is consensus that it actually was a failure, and then instantly move on. No punishment, no I told you so — just keep asking the same questions*.

Over the long term, your team will begin to internalize your thinking into theirs and then boom — you’ve achieved the dream of making yourself redundant.

*Assumption is you’re asking the right questions!!!

3. Force transparency, and get accountability for free

An open book makes for a good story.

Teams need to have the processes in place to continuously transmit their progress and the traction of their products to the organization.

Whether it’s reporting the metrics of a live product, the status of one in development, or the insights from user testing — a lightweight way to project the status of metrics the company cares about, available to anyone who wants to see them, creates a virtuous cycle in a product group.

“What if the team is doing poorly? Isn’t it demotivating?”

This is often talked about, but I don’t buy it. My principle is that you are not working with children (even 18 year old interns). People can handle it, and if they can’t they need to learn, because building successful products is hard.

The irony is that this line of thinking is actually often the cause of demoralization. When the team knows the product sucks, but there is a constant cheerleading and false projection of success by the leadership, people lose confidence — their thinking is, ‘either the leaders are too stupid to see it, or they think the team is too stupid to realize it’ - and start heading for the exits.

4. Create the shield of safety, but fight a war inside it

Engineers and designers should not be trying to solve problems under duress. It leads to bad products. Most people need to feel safe in order to be effectively creative.

As a leader, you need to find the right balance between ensuring that people really care about the success of the product, but are not in fear of their jobs should it fail. The only role who’s ongoing existence should be tied to success is yours (and likely your PMs).

In private conversation, it may be a shit-storm with your stakeholders. There may even be conversations of shutting it all down if you don’t grow. But to your team, you need to project confidence, optimism, and urgency — all at once, all the time.

To create the shield of safety, you need to wear “The Face”. Anyone who’s been an entrepreneur or leader of a team knows about The Face. It’s the white-collar equivalent of “service with a smile”, and is an analogy for the acting you must do to project the aforementioned qualities. Make no mistake, this face is critical, and directly affects the team’s performance.

In my opinion this is the toughest part of the job, and will be the first thing to break should you begin to wear out.

5. Get down into the weeds

I’ll keep this one short: there is no job too small. If your team is struggling to hit a timeline, you need to step up and help get shit done. Write the FAQ copy, do the manual QA, find the beta testers — your team will appreciate this.

This also has a second order effect of earning trust by showing you can also do the work.

6. The way you think builds the creative boundaries for the team, so think big.

You need to push the team to think big and long term. They will only think as big as you do. If you are too pragmatic all the time and focused on the not-too-hard or not-too-risky stuff, your team will only develop incremental product, and nothing innovative will ever emerge.

For example, if there’s some shitty way that your credit card processor pays out sellers on your marketplace and it causes a bad user experience, accepting that “it’s just the way the industry works” limits the scope of innovation. Pushing your team to make the best of it, instead of challenging them to find another way entirely, means you will never get disruptive products to market.

Sure they may fail, but the alternative is always needing to ship incremental features just to drive short term, and linear growth (at best), which is not why you and your team are here.

In hindsight, I was bad at this, often folding to the pressure to ship quickly and garner short term gains. But lesson learned.

7. Building and developing your team into leaders is your highest leverage activity

You should always have the goal of making yourself redundant. That is the clearest sign of effective leadership, and a skill that is insanely valuable to companies of all stages.

If you have the right people in place, you need to focus most of your time on developing them, unblocking them, and thus empowering them to do more than they ever thought they could. Throw bigger and bigger responsibilities at people, and 9/10 times they will stretch and meet the challenge. Humans are great like that.

If you don’t have enough people in place yet, you need to spend a disproportionate amount of time on hiring. This was ultimately my biggest failure during my time as a director - I was short a PM for over a year, relying mostly on HR to bring more candidates in the door (which didn’t pan out), and compensating for the gap by doing the PM work myself to hit the deadline — not long term thinking.

I should have been having ten meetings a day with every person I could find through my network until the right candidate was hired. I will not make that mistake again.

Heuristics are built for specific contexts

Using heuristics means appreciating that they won’t be good in every situation. In a different industry, culture, or stage of company they could be terrible principles to apply — so using them aren’t an excuse to stop critically assessing your decisions. At the same time, building these up are some of the most efficient ways to elevate your thinking and enable yourself to grow.