Andrew Skotzko

Connecting the dots between high-level work and low-level tasks

I was cruising around Reddit the other day when I came across this question:

Please suggest a tool that can help in tracking a product development process on high level features while the high level features are also mapped to specific tasks on a platform like Asana, so that at any given day I can get hold of where we stand on a given feature and what’s pending.

I also need the high level thing to be separate in a sense that it can be shared to all stakeholders whereas the task level thing remains private to my core team.

I love this question. It shows the product manager (PM) is thinking about how to help the team in shipping the right product to their users, AND is thinking about stakeholder management (an area where PMs often spend the majority of their time).

The other great thing about this is that hidden behind the question is the sense that the PM is thinking about how to keep everyone involved connected to the context as it shifts. Developers need to know what they’re working on, what’s next, and why.

I’ve gone down this rabbit hole myself many times with various teams, and understand the PM’s desire to have everyone involved in the project understand what they’re working on and why. Each developer or designer should be able to see how their work rolls up and fits into the bigger picture. The PM should be able to start from the abstract level and drill down to see what specific work is underway, and how it all connects.

However you set it up, you need to connect three things:

  1. The major efforts / building blocks to realize those goals
  2. The task-level work advancing those efforts
  3. Bonus level: the overall goals

This can be done manually with e.g. a whiteboard, or it can be digital. Each has its pros and cons. There are many possible ways to implement this.

My current approach uses just two tools: Trello, and ProductBoard.

Tracking the building blocks & features: ProductBoard

I really like ProductBoard for this. They have a simple but powerful tool for prioritizing, planning, communicating to stakeholders, and tracking task progress at a high level.

As of this writing, ProductBoard integrates natively with Trello, JIRA, GitHub issues, among others. They also integrate with Zapier, through which you can use Asana as well as many other tools.

I chose to pair ProductBoard with Trello because it will stay in sync automatically: as tasks are moved along the development pipeline in Trello, their status will automatically be updated in ProductBoard. The tool has options to let your stakeholders view roadmaps, etc.

If you don’t have budget for a tool like ProductBoard, you can create a more basic version of the same functionality with a separate Trello board for the high-level features/roadmap. I like the Hello Epics plugin to connect cards and do a similar work-status-linking within Trello. (You can also do this for free with Trello attachments, it’s just more manual work.)

Tracking task-level work: Trello

This is where Trello comes in. You can push work into the development pipeline directly from ProductBoard, and then as it’s updated in Trello the status will automatically update in ProductBoard. Trello is already one of the most popular project management and work-tracking tools online, so I won’t go into it here.

One important caveat: this has to be maintained. You can set up a great system, but without regular maintenance, it will wither.

The bonus level: overall goals

To really supercharge this, find a way to provide the overall context for the features and task-level work. In an ideal world, anyone looking at their Trello card could see the high-level goal it rolls up to. I like Hello Epics for this, but you can also just add it as a note on the card or as a keyword.

(For goal-setting, I use a goal-setting methodology called OKRs: Objectives & Key Results. OKRs are what most of the top tech companies use. They work. I recommend the approach laid out by Christina Wodtke in this article. Her book is also excellent.)

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Hopefully that shows you an example way to see how all the work being done connects to the features and high-level goals. This will help you keep your head around everything currently happening, and how it all connects.

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A simple framework for tough stakeholder updates

I had lunch recently with a PM named Mark. Mark was feeling nervous. The next day, he was flying to a big stakeholder meeting and needed to give an update on the state of a big project he’s leading. Things had not been going that well. Mark didn’t feel confident in the technical feasibility of what his team was working on.

He said to me:

I want to be honest with them about what isn’t working, but I’m afraid they’ll freak out. I’m not confident in our approach either. How do I tell them the truth but not spook them?

It’s inevitable to be in this place. Especially if you value transparency and intellectual honesty. So what’s an intellectually-honest-wanting-to-inspire-confidence-but-not-feeling-too-confident PM to do?

Good news: there is a simple, three-question framework that will help you feel more confident going into any such conversation,

The three questions in the background

Try to go into any stakeholder conversation having an answer to the following three questions—especially when things are going sideways:

  1. what’s happened?
  2. what’s it mean?
  3. what’s next?

You may not explicitly say these to your stakeholder, but the thinking and information contained in each

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Are you with us, or against us?

Think about the games you’re playing. Are you competing with the other players in the game, or are you competing against them?

Two ideas I’ve been captivated by in recent months are (1) the idea of infinite games and (2) mastery.

An infinite game is a game with no finish line. The point of the game is to keep playing, to stay in the game and keep it going.

Mastery is a mindset, a posture that approaches any medium from the long view. Embracing the long arc of never-ending improvement and ever deeper expression.

They seem related, but how do these fit together? And how do they frame the way we approach competition?

First, embracing the infinite game provides context for everything you do. It supports resilience through the emotional roller coaster of a finite game. When you know the game you’re really playing, you’re secure in that context. And it’s easier to adjust your approach without losing your center or sense of direction.

Once you’ve embraced an infinite context, then mastery is the mindset or posture to play from.

The mastery mindset is one which embraces the path of endless, goalless practice. This posture is the hallmark of the true master in any field. The mastery mindset is the most practical posture to both go the distance and enjoy the ride. It would suck to go on a never-ending journey without enjoying the ride itself. The mastery mindset helps make the infinite game inherently rewarding to play.

So, if we’re playing an infinite game with a mastery mindset, how do we think about the idea of competition?

One of the five things that you need to play the infinite game on a finite level is a worthy adversary.

In an infinite game, the only true competitor is yourself. We are always competing to be better than we were yesterday. To better fulfill our vision, to become more of who we’re trying to be. This is true at all levels: individual, team, organization, or society.

How to view external competitors, then?

Everyone else is there to reveal our weaknesses to us, so we can improve. They are there to provide the stimulus that pushes us to get better.

We need them. We need them to push us to see and reach for new levels of our own potential. Nobody does their fastest time alone. They do it in a race, with others.

This is what it means to compete with the players in the game. Here, we’re each competing to be better than ourselves, together.

Or, we can compete against the other players in the game. Here, we’re each competing against the others, by ourselves.

Are we trying to see how good we can be, trying to do something better than it’s ever been done before? Or are we just trying to beat them?

It turns out that “with us or against us?” is a matter of perspective. A choice. And yes, one choice works better.

One burns out. The other burns on.

What I want for Christmas: A Quiet Internet

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Social media has never been more popular. The world has never been more noisy than it is now.

I think it’s about to tip.

As we wrap up 2018, one of the most challenging aspects of doing meaningful work—and leading a meaningful life, frankly—is being able to actually hear yourself think.

People are really over the noise and the comparison-based existence that has become the norm in the insta-everything world of Instagram. I’ve been feeling this reaction happening for awhile, in myself and a lot of people in my network.

I generally try to avoid writing about the “topic of the day,” but I think there is an underlying pattern worth being aware of here: I think the “quiet Internet” movement may have just crossed the chasm, or is about to.

So what’s really going on here? How should we think about this?

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The work grows out of the work

One definition of art that I find useful is “a generous gift intended to change the recipient.”

From that, it follows that we are all artists, or can be.

If you don’t like “artist,” then “creator.” We each have the capacity to create things and put them into the world from a generous posture.

But what to create?

This question is both useful and dangerous. Useful, because work worth doing embodies thought and intention. Dangerous, because it contains a trap. One that I’ve fallen into many times in the last few years.

The trap is seeking only new ideas and ignoring the ideas you already have. Usually because they aren’t new to you anymore.

I’ve burned a lot of energy this way. I didn’t grok that, as Ted Orland and David Bayles wrote in Art & Fear, “the seed for your next art work lies embedded in the imperfections of your current piece.”

Read that again.

As they go on to say:

The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars.

Despite our wishes, none of us know which of our creations will soar, if any. So we must learn to find fulfillment, joy, energy, and value in the whole journey, rather than only at the imagined end.

This is especially true on long projects that have interminable stretches, when we’re out to sea and land is a long way off.

Making the work you want to make means setting aside these doubts so that you may see clearly what you have done, and thereby see where to go next. Making the work you want to make means finding nourishment within the work itself.

Learn to find nourishment in the journey and work itself.

The work grows out of the work.

Running toward uncertainty

The same way soldiers run toward the sounds of shooting, or firefighters run toward the blaze, effective leaders run toward uncertainty.

Uncertainty exists wherever there is tension. Tension is the indicator of change. And change is the work of a leader.

If you’re leading an initiative of any kind, look for the tension of uncertainty and run toward it.

One guiding mantra I picked up along the way as a team lead is “make good things happen.” (Thanks, Scott.) When I don’t know what to do, I start looking around for something good to help happen.

One of the fastest ways to make good things happen in any kind of project is to create clarity. Even though there will be course corrections later, you free people up to charge ahead right now when they have a clear target.

Some good places to start with are where we’re going, why, how we’re getting there, and what comes first.

Just remember: about the time you’re sick of saying it, that’s when they start hearing it.

Impossible*

“Impossible” and “Unpossible”: we confuse these two ideas all the time, and it doesn’t serve us.

Something that is “impossible” cannot ever possibly happen, according to all known laws of science.

Something that is “unpossible” cannot happen according to reality as we know it.

There’s a difference.

Most of what we call “impossible” is actually “unpossible.” Something I want may be impossible to me, right now, this month, with my current circumstances. That means it’s not impossible, it’s merely unpossible.

Really, instead of saying “that’s impossible” we should be saying “that’s unpossible.” Or “that’s impossible, according to how I have defined this other term.” Or, if we really want to be honest about it, we could say “that’s not possible for me, yet.”

Even something “impossible” should have an asterisk next to it, because our scientific understanding of the laws of nature is always expanding. New discoveries can and will change our understanding of what’s possible. That’s what science does, and it works.

The word that changes everything: “yet.” But I’ll take an asterisk as a shorthand for ‘yet’.

Faster than light travel: impossible*.

Next time you find yourself writing that something is “impossible,” try writing it as “impossible*” instead.

The ‘expiring veto email’

I was coaching a new team lead at a startup yesterday, and he brought up a challenge I think probably affects many teams: how do you deal with being blocked waiting for a decision about day-to-day work from the person you report to?

This happens because nobody likes being negatively surprised. Especially in a startup that is going through many growing pains, there are many fears, not the least of which is the fear of losing control.

(Control itself is an illusion, but that’s a separate topic.)

These managers want to be in the loop and know what’s going on. What they’re afraid of is things going sideways and getting blindsided, when they could’ve prevented it somehow.

This is a reasonable concern. Senior leaders in any org have a different perspective than other people, because they are seeing everything. They can often spot problems from their perspective that someone directly involved with the work can’t. These are often integration problems or long-range implications that aren’t obvious in the moment.

Usually, these people don’t have all the information needed anyway and are ultimately going to push the decision back to the people closest to the work involved.

They just want to be in the loop, know what’s happening, and be able to contribute thinking and guidance if they see something that isn’t working or if they have a different perspective from their vantage point.

The problem is that such well-intentioned practices lead to a bad place: bottleneck.

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On always being wrong

I learned a new phrase from the one and only Seth that has lit my mind on fire and freed up my creativity: “Always be wrong.” (Expect this and much more in his highly anticipated new book, “This is Marketing,” which comes out next week.)

WHAT? Be…wrong? Are you kidding me?

That was my first reaction, anyway.

But here’s the deal, and it’s actually very freeing:

The idea is to be wrong all the time. To ship generously, and get it wrong. But to be getting it wrong from a posture of generosity and service. Coming from a posture of trying to serve. Showing up for people, for customers, with right heart and right intention to serve.

And then, take notes.

Take notes about where you’re wrong, learn the lesson, make it better, ship again.

We’ve given “wrong” a bad name. I don’t know about you, but I’ve grappled with this for a long time. We’ve all been trained that there is a right answer and that we have to have that answer. Looking for The One Answer to Rule Them All, when there are Many Possible Great Answers.

This often manifests as over-preparing, studying too much in advance, trying to reverse engineer it all up front.

Turns out, it’s much more efficient, faster, and simpler to make a generous attempt, be wrong, learn, and repeat. As long as it’s done with the right intention, it builds connection and trust with customers, with those I seek to serve.

But there is a simple fix: take the sting out of “wrong.” Make “wrong” a friend.

How? Two steps:

Step one: Give yourself permission to ‘always be wrong.’ If you do, and the market does, this is permission to get it wrong. Permission to stop endlessly preparing and trying to get it perfect from the jump. Freedom from trying to reverse engineer everything in advance and solve it all before you leap.

Step two: Pair ‘always be wrong’ with ‘always be learning.’ This is about cultivating a growth mindset (for more on how to do this, see Lesson 2 in my altMBA recap).

If you’re just wrong, but getting better and trying again, you’ll burn out. And that doesn’t serve you or those you seek to serve.

This isn’t permission to ship crap. Give it your best attempt. But it is permission to be imperfect and go anyway.

“Wrong” is the doorway to better, and what opens that door is saying “thank you.”

“Wrong” is the only place I get to be a learner and get better and grow.

“Wrong” is a wonderful place to visit. Just don’t stay there.

Adulting: The Fundamentals

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“Get it together, dude.”

“Ugh, I hate my job.”

“I have no idea what to do next.”

“I feel like such a loser.”

We’ve all been there.

Life can be hard, unfair, challenging. But no matter what life brings my way, I want to be always learning, growing, and getting better. I want to get the most out of my life and assume you do, too.

Whenever I’ve thought something like the above, it’s always come from a place of deep frustration. I’ve wanted and needed an answer. I knew something was off, but was stuck as to how to move forward.

In my experience, the real problem is usually that I’ve stopped taking care of the fundamentals. Part of the foundation of my life is out of whack.

So I start in the wrong place, putting the cart before the horse. I address the symptoms but not the causes.

Oh, you too? Glad I’m not the only one.

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