Andrew Skotzko

Paula Daniels: Living on the edge of your own invention (#8)

Paula Daniels is an award-winning social entrepreneur and Ashoka Fellow with a deep history in food and water policy. She’s the founder of the Center for Good Food Purchasing, a nationwide program that uses the power of procurement at large public institutions to create a transparent and equitable food system that prioritizes the health and well-being of people, animals, and the environment. They are currently partnered with 18 cities and 40 large public institutions, impacting more than 2.2 million meals a day and something on the order of a billion dollars of institutional food spending each year.

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Becky Baybrook: culture, candor, and how Millenials are changing management (#7)

In this conversation, Becky and I dig deep into workplace culture. We explore some vexing questions around belonging and psychological safety, how Millenials are changing management. One area that I think listeners will find especially useful is a discussion we have about what the elements that make up workplace culture, and tactically, how you can get a good read on a culture from the outside if you’re considering working with an organization.

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Barry Brown: Shaping the shapers (#6)

My guest in this conversation is Barry Brown. Barry helps leaders be more of who they are and be more effective in bringing forth the change they seek to make in the world. He’s someone I call a “shaper of shapers,” and by the end of this conversation, you’ll understand why.

We dive right into the deep end about what it means to be a grounded, humble leader, and what it means to embrace the limits within our work as a pathway to our individual and collective evolution. We also discuss how to bring a craftsman mindset to your work.

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Rich Mironov: Building a thriving product organization (#5)

My guest in this conversation is Rich Mironov (@RichMironov).

Rich is known as the “product mensch” in Silicon Valley, and for good reason. Educated at Yale and Stanford, Rich is a 30-year veteran of product management at multiple enterprises and startups that have gone public who now consults as an interim VP of Product helping companies to get their product organizations working at top-notch.

In this conversation, Rich enlightens us on how to create a thriving product organization and how a product leader can right the ship.

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Marshall Mosher: tough product calls, acclimating to fear & what it feels like to be Iron Man (#4)

Marshall Mosher is the cofounder and CEO of Vestigo, a company that uses outdoor adventure experiences to help people push outside their comfort zones, get comfortable being uncomfortable, and build deep trust with their teammates.

Marshall caught the entrepreneurial bug at the tail end of his masters program, and hasn’t looked back since. After graduating from the University of Georgia, Marshall spent time at the Singularity University Global Solutions Program Fellowship at NASA Ames and has been on the path of empowering human experience through technology since then.

This is such a fun conversation and I can’t wait for you to listen to it. We cover soo much ground. We talk about how to make product pivots and how to face down the emotions involved in walking away from a major product investment. We talk about self-identity, and how it affects our ability to pivot and learn and grow.

We spend time talking about how to cultivate trusting teams and create experiences where people deeply connect with each other, and how you can bring that to the people in your life.

Always focused on learning pushing outside his comfort zone, Marshall also shares with us what it feels like to actually fly around in an Iron Man jet suit!

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Barry O’Reilly: Unlearning and creating culture change (#2)

In this episode, we meet Barry O’Reilly, a business advisor, entrepreneur, and author who helps people invent their future instead of fearing it. We start by dropping right into a powerful moment in Barry’s career as an entrepreneur and go on to cover everything from deliberate practice, to culture change within an organization, to how thinking we’re right gets in the way of our own growth (and what to actually do about it). Andrew will be your guinea pig in the hot seat for Barry to demonstrate some of his unlearning techniques.

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May Lindstrom: Delivering love and the power of a North Star (#1)

May Lindstrom
“You can’t do love from fear.”
— May Lindstrom

In this first episode of ENLIVEN, we meet May Lindstrom, the founder of May Lindstrom Skin. She shares her incredible story of creating a beloved company that is transforming the skincare industry and creating a thriving life for herself and her employees. And how she’s delivered love with unwavering integrity.

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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 [Read more…] about A simple framework for tough stakeholder updates