Speed of Collaboration in the Days of Email vs Teams/Slack

Email feels so old and slow, especially when compared to the teal-time multiplayer world of Teams and Slack.

It makes sense for transactional emails but conversations and project managing it sucks. But you can’t just add a client or external contact to your chat app.


What if an initial email is sent and it operates as expected. You send something along the lines:

Hi Becky,
It’s great to meet you. I would love to work with you to get ______ completed by such and such a date. Please find attached a file that is required for this project.
Let me know if you have any question.

Made up by me

This is where it gets fun

Once the recipient replies or accepts the messages, the thread then morphs into more of a live style conversation. No more signatures repeated over and over or from: to: cc: fields creating noise to pour through or weird formatting problems. It’s becomes a chat with multiple players.

  • Participants From: and To:
  • Observers CC:

Attachments, links, and relative information could be pulled and listed to a special tab/space and possibly even anchored at the part of the conversation that was relevant

May you could see if someone was on Live for a short period of time.

It could be wild but it would maybe help or maybe things a lot shittier. But at least we’re trying.

Tune-Yards – Bizness

Tools #3: What the Hell is Going On!

Continuing the thread of re-coaching myself to think – https://ant.cat/tag/untool/

Today’s Lesson – How to look at a problem through a set of lenses (hats in this case) one at a time and focus.

The tool of the week is – https://untools.co/cynefin-framework Cynefin Framework developed by Dave Snowden in 1999

The goal is to help make sense of a situation to help guide a response.

First: Which domain are you in (see diagram below), then the action based on the characteristics

Clear – typically process-oriented situations and problems. Domain of “known knowns”. Approach: sense–categorize–respond. Understand the situation (sense), categorize it, then respond by applying a best-practice solution.

Complicated – typically has multiple right answers. Domain of “known unknowns”. Approach: sense-analyze-respond. Because analysis is needed they require expert knowledge. Experts should assess the situation, investigate possible options and choose a course of action.

Complex – domain of “unknown unknowns”. Approach: probe-sense-respond. we don’t yet know enough about it. It’s not clear what needs to be answered in the first place. Experiment first, learn about the problem. Then sense what you’re dealing with and respond appropriately. The goal should be to understand enough so that the problem or situation moves to the complicated domain where it’s easier to deal with.

Chaotic – just out of control. Approach: act-sense-respond. “First act to establish some stability, to contain the situation. Only then assess the situation and work on bringing enough order to it to move it into the complex domain.” One benefit is that you can try weird and wild stuff because the pain of the chaos creates the chance to solve it in any way possible.

Don’t know which one? You’re in “Disorder” – The best place to start is to break-up into small parts and try to then put them into each bucket above.

Questions to help determine the domain you’re in:

  • Do you know what causes the situation?
  • Is the situation under control?
  • How much do you know about it?
  • Does solving it require expert knowledge?

All credit for the above belongs to https://untools.co/

Holy Crap, finally done: High Impact Management

Reading a business book in public like High Output Management feels like the dorkiest thing in the world. All I think is, “what a try-hard this guy is.” But the cool thing is I’m not in high school anymore and caring about things is cool. So f* those people (who probably don’t exist) judging me.

I started this book on April 20, 2022 (again…originally started multiple times before but just could not make it past the first few pages) –

Here are the takeaways: (this guys took way better notes: https://medium.com/ceoeducation/notes-on-high-output-management-19b8017495d4 )

Chapter 1:

  • Remember the breakfast factory: our job is to understand the “limiting step” in the process
  • Don’t let the wrong step be the limiting step
  • The black box of creating things: how might you create holes in the process to check on things being made and make sure they’re being created
  • QA – In-process test vs functional tests
  • Try and detect problems as soon as possible in the process, it’s the lowest value stage

Chapter 2

  • More on Blackbox Indicators – How do you keep an eye on things? Here are the big chunky phases to create indicators:
    • Sales forecasts – and how do you measure confidence and adjust the forecast process
    • Material management
    • Condition of equipment
    • Workforce
    • Quality
  • Don’t overfit your indicators – “You get what you measure” to avoid this you can pair indicators to create a balance (should add an example here
  • Linearity Indicators vs Trend Indicators (example: measuring output against linearly should show continuous progress as opposed to huge pushes as a deadline comes up
  • What if need to make compromises in QA – you need to do it with a well balanced management team but never ever mess with reliability
  • Leverage
    • Pg. 35 started to hit on how you can change how you work to get more leverage
    • Output vs Activity
    • Embassy example – when 98% are approved when everything single is reviewed…they should move to sample tests

Ok, the rest of the Chapters.

At some point you have to just finish something and that’s where I got with this book. So many great things in there but also I’ll need to revisit. Here are the things that really stood out to me:

  • Remember the breakfast factory:
    • What are your limiting steps?
    • How can you cut holes in the factory box?
    • Where can you find leverage?
  • Strive for output that aligns with outcomes
  • Don’t let the process become the thing – that aligns with Wiggly
  • Be a coach: No credit, Be tough, Good coachs were good players

Excercise at the end of Book

Great things to do after reading this book:


  • Identify the operations in your work most like process, assembly, and test production.
  • For a project you are working on, identify the limiting step and map out the flow of work around it.
  • Define the proper places for the equivalents of receiving inspection, in-process inspection, and final inspection in your work. Decide whether these inspections should be monitoring steps or gate-like. Identify the conditions under which you can relax things and move to a variable inspection scheme.
  • Identify half a dozen new indicators for your group’s output. They should measure both the quantity and quality of the output.
  • Install these new indicators as a routine in your work area, and establish their regular review in your staff meetings.
  • What is the most important strategy (plan of action) you are pursuing now? Describe the environmental demand that prompted it and your current status or momentum. Is your strategy likely to result in a satisfactory state of affairs for you or your organization if successfully implemented?


  • Conduct work simplification on your most tedious, time-consuming task. Eliminate at least 30 percent of the total number of steps involved.
  • Define your output: What are the output elements of the organizations you can influence? List them in order of importance.
  • Analyze your information and knowledge gathering system. Is it properly balanced among “headlines” and “weekly news magazines”? Is redundancy built in?
  • Take a “tour”. Afterward, list the transactions you got involved during the course.
    Create a once-a-month “excuse” for a tour.
  • Describe how you will monitor the next project you delegate to a subordinate. What will you look for? How? How frequently?
  • Generate an inventory of projects on which you can work at discretionary times.
  • Hold a scheduled one-on-one with each of your subordinates. (Explain to them in advance what a one-on-one is about. Have them prepare for it.)
  • Look at your calendar for the last week. Classify your activities as low/medium/high leverage. Generate a plan of action to do more of the high-leverage category. (What activities will you reduce?)
  • Forecast the demand on your time for the next week. What portion on your time is likely to be spent on meetings? Which of these are process-oriented meetings? Mission-oriented meetings? If the latter are over 25 percent of your total time, what should you do to reduce them?
  • Define the three most important objectives for your organization for the next three months. Support them with key results.
  • Have your subordinates do the same for themselves, after a thorough discussion of the set generated above.
  • Generate an inventory of pending decisions you are responsible for. Take three and structure the decision-making process for them, using the six-question approach.
  • Evaluate your own motivational state in terms of the Maslow hierarchy. Do the same for each of your subordinates.
  • Give your subordinates a racetrack: define a set of performance indicators for each.
  • List the various forms of task-relevant feedback your subordinates receive. How well can they gauge their progress through them?
  • Classify the task-relevant maturity of each of your subordinates as low, medium, or high.
  • Evaluate the management style that would be most appropriate for each. Compare what your own style is with what it should be.
  • Evaluate the last performance review you received and also the last set of reviews you gave to your subordinates as a means of delivering task-relevant feedback. How well did the reviews do to improve performance? What was the nature of the communication process during the delivery of each?
  • Redo one of these reviews as it should have been done.

Tools #2: All the Hats

Continuing the thread of re-coaching myself to think – https://ant.cat/dogs-and-tools/

Today’s Lesson – How to look at a problem through a set of lenses (hats in this case) one at a time and focus.

The Untool of the week is – https://untools.co/six-thinking-hats

Based on the book Six Thinking Hats, Edward de Bono – https://www.goodreads.com/book/show/97030.Six_Thinking_Hats

Illustration of the Six Thinking Hats: Yellow for positivity, Green for creativity, Red for emotions, White for data, Black for negativity and Blue for control.


Trying to picture how this will actually work. I’m not great at compartmentalizing. Or maybe I could… starting with the Green Hat, then having people looking at the ideas in phases?

Or is the focus on One big idea, then putting on the Black Hat, then using the Green Hat to work around the Black Hat’s issues, and then trying to find the viable solution using Yellow, Red, White, Blue?

That could be interesting. My brain wonders quite a bit so I could see myself constantly trying to put all the hats on at once, but that’s not helpful to anyone. Much like mindfulness, being able to focus with a specific goal in mind is a muscle that I just need to flex more. But that’s where the Blue hat comes in: “🔵 Blue hat is for controlling the process. Especially in meetings, it’s good to be able to step in when there’s no progress and enable the group to move forward (e.g. by shifting the thinking or discussion to a different hat/perspective).”

Key Takeaway: We all need facilitators and Blue Hat

My daughter’s favorite video/music is a great fit for this one.

Tools #1: Dogs and Tools

Trying to learn as an adult is so hard. You already have so much of your neural network built and weighted that you get pulled back into old patterns. I mean the saying goes you can’t teach an ol’ dog new tricks. But, I think a better version is you can’t teach an ol’ dog new ways of performing old tricks that treated them well so far and got them to where they needed to go. That’s too long I guess.

I stumbled across this site: https://untools.co/ that is all about trying out different mental frameworks. My goal is to read through one of these each week and truly digest it, get into the noggin, and hopefully, it will push this ol’ dog to be some __% better.

What’s funny is that I’ve spent the better part of 10yrs facilitating innovation sessions for groups of 20+ people specifically around breaking your thinking. It’s just really hard to do this for yourself. Turns out people need people.

Old Ignite Workshops

Untool – Conflict Resolution Diagram


  • They reference this was pulled from the “Theory of Constraints” by Eliyahu Goldratt
  • The goal of this tool (aka “Evaporating Cloud”) is to be used when a conflict seems impossible.
  • There are three parts worked in the following order:
    • Demands/proposals of the opposing sides: these are usually mutually exclusive which is what creates the conflict.
      • Ask: What does the other side want to do? What do I want to do?
    • Underlying needs or requirements of both sides
      • Ask: What needs are satisfied by the proposal of each side?
    • Shared goal or objective that’s behind the needs
      • Ask: What will be achieved by meeting the needs of both sides?
      • This is important to come to a shared understanding as you become part of the same team, but you happen to be approaching it differently.
  • Now that the above is taken care of, you’ll need to discuss the assumptions that are behind the original approaches. This will most likely uncover why the approaches are at odds.
  • Ending – now you build the solution together with a focus on the shared vision/goal.

This reminds me of a reverse flow Opportunity Solution Tree that Teresa Torres talks about https://www.producttalk.org/opportunity-solution-tree/

Remember: focus on the outcomes and let that help dictate the path…hopefully a path takes into account kindness 😀

Growth and Leadership: Areas to Keep in Mind

Over the last two days, I put myself in a training (SkillPath “Management & Leadership Skills for First-Time Supervisors & Managers”) to help me better at helping others. About 7 weeks ago I was provided a great opportunity to move into a group product manager role and work with 3 current product managers and hire an additional product manager.

Group product manager has some nuances that make it vary a bit from what I’m used to. 1.) is that I’m still a direct contributor and 2.) I now have direct reports. This made me real nervous. How was I going to get my work done and provide the team with everything they need. We’re only 7 weeks in so we’ll see but I still need to do everything I can to grow in my leadership and not wing it. But truly couldn’t be more excited to work directly with seasoned product managers who know how to get their work done. We’ll learn a lot from each other.

Here are my take-aways from the day. Link to PDF

  • Learn to be direct but respectful = assertive
    • How to say No respectively: Understanding, Situation, Action
  • Focus on Logos (logic) , Ethos (ethics) , Pathos (emotion) ….but really get better at Pathos and being a true listener (body, mind and ears)
  • Don’t be fiddle-faddle with your meaning or words, a real struggle: let your yes be yes and your no be no
    • I thought this was cool quote “Catch somebody doing something right”
  • Be great at feedback: LB-NT (Like Best, Next Time) and maybe add reinforcement and help them prep when the “next time” is coming up
    • ‘But’ and ‘However’ marginalize all your previous comments
  • Be amazing at meetings: setting the stage, coming away with actions, and not wasting everyone’s time
  • If sending someone to training ask them to think about:
    • What am I learning?
    • So what?
    • Now what?
  • Asking is always better than telling
  • “You are paid for your team’s success”

Podcast: Monday Morning Mimosas

Back towards the end of 2017, my friend Sarah Bettencourt asked for me to join her on her podcast to chat about entrepreneurship. It posted this past Monday! We covered a ton of topics and the one I wouldn’t shut up about was Slack.

Monday Morning Mimosas with host Sarah Bettencourt

Here’s why I think Slack is interesting. There are a bunch of hidden communities around the world leveraging Slack as their communication channel and a place to cultivate an audience. The trick is you already have to have an audience to get the channel going, and you’ll need well over 100 people to use it often to bring in enough interaction.

Joining a Slack channel can be near impossible or extremely easy if the host allows it. Either way, the application creates a lot of engagement and opens up the door for a new kind of online social experience.

Side note: Discord is another chat app that falls in this same world, but with a focus on the gaming community. What’s amazing is their onboarding experience…holy moly it’s frictionless.

Instead of a music video, you get the lovely Sarah’s voice:

How Slack Can Help You Be A Better “Preneur” With Anthony Catanese

Winded by Design Sprints

Also posted on Medium:

I love when groups get together and collaborate, but please try to avoid making the same mistakes our team did… It only leads to the group becoming drained, wiped-out, and winded.

TL;DR: Design sprints are amazing, but they aren’t magic. After 5 years, 50 design sprints, and countless ideations for tech, HR, and financial firms, I’m worn out by companies misusing them. The worst thing a product team can do is get stoked about a new sprint process, run five of them back to back with the same team, and burn them out in the process. Below are 12 things a team can do to get the most of their sprints.

A little background: What is a design sprint and what is the typical process? Google Ventures does a great job breaking it down: http://www.gv.com/sprint/ or buy the Sprint Book by Jake Knapp, John Zeratsky, and Brand Kowitz

david-marcu-69433 Photo by David Marcu on Unsplash

When design sprints rock.

Be clear and concise about what you’re trying to solve. Design sprints are not designed to solve world hunger, one giant problem. They’re designed to focus on one specific piece of a big problem and optimize it.

We did this by leveraging “How might we…” questions to break down our big (world hunger) problem into bite-sized chunks. Then we focused on solving only one of the questions during the sprint.

“How might we…” questions are a helpful way to frame the problem at hand and move the team in the same direction.

For instance, How might we… (in regards to the massive problem of world hunger)

  • … inform the public that world hunger is a real problem? (marketing and messaging)
  • … get excess food to the people who need it? (logistics and distribution)
  • … work with partners that will provide the food? (sourcing)
  • … etc

Bring the real voice of your customer into the room.
Before the sprint, set up a time for a customer or two to chat with the team during the beginning of the sprint. Ideally, the chat will take place after the team has figured out what part of the big problem they’re trying to understand. This can be a video call, phone call, or in person interview that the whole team sits quietly and listens to while a facilitator asks questions. The goal is to gain empathy, and understand how the customer’s world works today.

My favorite question to ask during a customer interview is, “If today was my first day on the job, how would you train me to do this part of the job?” It puts your customer into teaching mode which gives the team a whole new view of the problem.

Constraints are key.
Many of the workshops we ran were left wide open with little constraints for the sprint participants. Our hope was to open up all ideas. It didn’t work. Participants often times froze and the ideas that came out fell flat most of the time. It’s like handing someone a blank piece of paper and saying, “Draw me a picture.” Instead, give them some lines and dots on the piece of paper and a mission.

What types of lines and dots can you create to help participants solve the problem? Maybe ask them, “If we only had a week, how would we solve it?” or “How would another company solve it?” or “If smartphones didn’t exist, what would you do?”

Keep everyone present.
Context changes are your absolute enemy. It’s rare to get a dedicated team together to give their full attention to a single priority. Treat this time as sacred. Starting the sprint a little later in the morning, like 10 a.m., gives people the space to get life/work in order so they can focus on the rest of the day.

Let participants design ideas alone, but share as a team.
The bookSprint by Jake Knapp, John Zeratsky, and Braden Kowitz talks about giving people personal time to work by themselves. This was my biggest takeaway from the book and it created the most dramatic and positive results from our workshops. The ideas were thoughtful, more complete, and gave everyone a chance to contribute.

marvin-ronsdorf-196913 Photo by Marvin Ronsdorf on Unsplash

When they suck.

Here are the top ways to burn your team out on sprints.

When the wrong users/customers are tested at the end of the sprint.
Reach out to an array of potential users/customers the week before the sprint and tentatively schedule them to demo the solution at the end of the sprint. Set the right expectations that it’s tentative and their participation would be invaluable. After the first day, when the problem is defined, check your interview list and make sure your potential testers match what you’re looking for.

If the team still feels they demo’d to the wrong users/customers, run the demo again the following week with a new cohort.

When the team can’t be together for the whole week.
Break the sprint into three parts, but don’t feel like you have to run all the parts back to back. Each part can be scheduled separately to find a time for everyone to participate.

 – Part 1 – Defining the problem
 – Part 2 – Prototyping
 – Part 3 – User Interviews (In my opinion, this is the piece you want the whole team together to experience live. It brings life back to the team.)

When the group leaves without a final recap of the week.
Be sure to do a recap with the whole group, get them to share feedback, and determine your next steps. Take lots of pictures during the week, bring them out at the recap to help people remember what was covered.

When the team has no clue how the results translated to a change in the company.
Treat the sprint team like internal customers. Update them continuously as the product is developed or the problem is solved. Keep them informed and encourage them to advocate for the sprint process. Nothing sucks more than time wasted.

When the team feels like they wasted a week of their time.
Set up parameters that are very clear about what it will take for a successful sprint. Success is learning that what is being tested is either right or wrong…anything in the middle is hard to move forward with. Avoid flowery language.

When the facilitator overlooks the little things.
Don’t miss the care and feeding of the team. Be an amazing host. It’s a mentally taxing week. Provide healthy snacks and lunches to keep people moving. Check-in with the team before moving on to new pieces of the agenda. Make sure everyone is on the same page. Questions such as “What’s your biggest concern at this point?” will help bring out a candid conversation.

When it’s the same team, same process…over and over again.
Stop running the same team through the same sprint process over and over again. Change up the problem, add new unexpected teammates that would not typically be involved, like customer support, and try new things in the sprint process. Here are two great books for collaboration exercises: CTRL + SHIFT and Gamestorming.

To wrap-up, team collaboration is an amazing tool and my favorite part of what I do. Don’t give up on the process, keep the team working together, try out new processes, and avoid being winded by sprints.

P.S. here’s a quick tip on remote user interviews:
For remote testing: we’ve used Lookback.io. Great product, but enterprise users may have restrictions on the types of Chrome plugins they can install. Webex is your answer if that’s the situation. Have the user share their screen, and turn on their video. The session can be recorded for the rest of the group that couldn’t attend. Also, be sure to have at least 30mins between interviews to give the team a chance to recap and get some notes down.


No, I agree

I’ve had this one in the hopper for awhile, and silly enough I wasn’t sure how to write it. It’s about communicating.

My Biggest Struggle, Communication

I have to say my biggest struggle, and I think for most people, is with communication. This plays such an important role in everything we do from interacting with families, coworkers, and helping people solve problems, yet we’re all so good at sucking at it.

I realized just how bad I was when I heard myself say, “No! I agree.” Which is it Catter (my friends call me Cat), No or I agree?

In this situation, it’s always I agree.

This is just the tip of the iceberg for me, and is a little communication deal that can be solved just by changing my personal habits. A much bigger struggle  though lies in the same realm, framing the problem.

Frame the Problem

You can conquer nearly anything in this world if you can do one thing, frame the problem. What does that mean? This means that you can take a problem that you’re trying to solve and change your approach based on who you’re talking to. You frame the situation for them in a different way that speaks their language and get’s them emotionally involved in what you’re solving for. Simple…I know.

There is a short blog post here that explains techniques to do this in more detail: www.idea-sandbox.com, and a great video from Clayton Christensen called “Jobs-to-be-Done” that shows this working for a company that wanted to understand why people bought their milkshakes.

Clayton Christensen- Jobs-to-be-Done

Did you catch the reframe of the milkshake problem? The reframe is in the, “Why did you hire this product?” This tilted the problem and gave a  different view to the customers. It took them out of the  process of thinking what they’re doing, and put them in a state of why this milkshake was in their life.

This means that as a product owner you  need to change your messaging for every person involved. You need to nail the problem of your customer to the customer in their language, you need to frame a customers needs to a developer in their language, and you absolutely need to speak the language of your investors.

This is all simple stuff, but we struggle with it – all of us. If we didn’t, then we would understand every product ever created. My hope is that by writing this I can revisit it and understand how poorly I explained it 😉

The Delfonics – Didn’t I Blow Your Mind This Time – Live 1973


I chose this song because I finally saw Jackie Brown last night and because honestly….Didn’t I Blow Your Mind? 🙂

A Letter to Enterprise Product Development

Dear Enterprise Product Development,

I hope this letter finds you well and development on that 3 year project is moving smoothly. I understand you’re very busy, so I’ll make this short.

Do you remember that small company that you read about a year ago on TechCrunch? It was run by 3-4 guys, they only had a few hundred thousand dollars in funding, and were charging only half the normal price of the industry.

Remember how we joked about how all the startups in San Fran operate in a bubble, only provide services for each other, and just exchange each others resources.

I thought you should know they just landed one of your competitors top clients.

You may be saying, “Ok, now what?”

I say IgniteWithUs.


Anthony Catanese


I heard feedback that this didn’t make sense. Maybe I tried to be too deep and obscure. I thought of this letter when I read about a startup that’s starting to make headway and it happens to be in a similar space as the company I work for. A year ago I read about them and I shrugged it off. They’ve grown, pivoted, and now they are competing with our competitors head-on…they’re changing the industry conversation.

That’s where the the last 2 lines of the letter come in. You say, “Ok, now what?” As in, what can I do about it?  Make better PowerPoints? I say you create a new group that innovates, which is what we do: IgniteWithUs.


Le Loup – We are Gods! We Are Wolves!