My Last Day At PivotDesk

David and I have decided that it’s time I leave PivotDesk.  This has been the hardest choice of my professional life.

I wrote the team at PivotDesk a few days ago and stopped by the office to wish everyone well.   We have made commerical real estate more efficient and cost effective for everyone from entrepreneurs to small business owners to brokers and I’m extremely proud of that.

Hopefully this post helps others avoid a similar situation in their companies and gives some context on how this can happen to the best of teams.  As several mentors and incredible friends have told me, this is way more common than people realize.

Alright (sigh), now that’s out of the way so let’s talk about what the hell happened.

Over the past six months I gradually lost the confidence of my teammates.

Here’s how it happened.

Tunnel Vision
For the past three years I’ve woken up in the morning thinking about how to grow PivotDesk and fallen asleep almost every night thinking about what else I should have done that day.  At the park with my kids I was always reviewing my task list, on the weekends I’d crave time alone so I could think about what’s coming up, everything was about growth, scale, more.

I was so caught up in this type of thinking for so long that I had blinded myself to all of the other things that make a team truly work well together.  As all teams do, we’ve had a few disagreements over a variety of situations.  I handled these situations with little care, love or respect for my teammates.  I just wanted it over so we could go back to growth, scale, more.  Little did I realize, I was slowly eroding the support from my team that is needed to succeed together.  And worse, I was growing defensive and outwardly frustrated as my stress level rose.

Stuggling With Co-founder Balance
I began as VPE at PivotDesk and after our MVP and Engineering team took shape moved to VP of Product where I’ve been for the past two years.  I also have a second job as Co-founder.  This job has no job description or performance metrics, rather it’s a mix of a zillion different things from sales to ops to bizdev to customer support.  Finding the balance between these two roles has not been easy and is another reason I ultimately lost the team’s support.

Just a few examples:

  • Taking coffee meetings instead of attending daily standup.
  • Running the company meeting instead of focusing on a great product update during that company meeting.
  • Letting my week fill up with sales, finance, pr and exec team meetings and not leaving myself enough time for deep product focus.

As I asked others on my team for feedback once I realized things were going sideways I heard things like “No one really knows what you do anymore.”

Making the Hard Decision
Saying “hard decision” doesn’t even come close.  When David and I talked about the possibility of me leaving I started visibly shaking, my mouth turned dry and I started having trouble breathing.  As the words “If I’m getting in the way at all, we should seriously consider that I unhook from PivotDesk” came out of my mouth it was surreal.  All of the emotions started kicking in; the Imposter syndrome, anger, disbelief.  We decided to give it a week, talk to the people that have seen this the most, then regroup and make a decision.  For a week I let all of the “Co-founder projects” slip and focused only on product.  I felt like our team was in perfect harmony and kicking ass.  We released a major feature and were collaborating perfectly on the next feature.   Our OKRs were lining up to our analytics informing what we were building and planning on our roadmap.  Ironically, it was one of my favorite weeks of work ever in my career.

At the end of the week David and I spoke again, there was no change in the team’s support, it was time to unhook.  I was crushed.

When talking with a good friend and mentor of mine this week he said “You are not special!”  As I laughed and said, “Hey, thanks a lot.  Is that supposed to make me feel better.”  He said yes and went on to talk about seeing this happen in different ways over and over in fast growing startups.  The company changes so fast and sometimes people and teams simply aren’t the right fit for the phase of the business anymore.  This did make me feel better and he encouraged me to not assume 100% of the burden.

The Next Chapter
It’s incredible how much of one’s identity can get wrapped up in the company they are trying to build.  The constant pitching, the t-shirt wardrobe peppered with company logos and talking about the business at every holiday, lunch with friends or phone call with Mom really adds up.  It’s what you live and breathe as a startup founder and I wouldn’t have had it any other way.

For me, one thing has always stayed constant over the past 20 years of my professional life whether working at a big company or startup, the love of building software.  From the first 10 years as a software engineer through today as a product guy, day-dreaming about cool ideas and turning them into reality is thrilling.  I still get nervous as a I watch customers, friends and teammates use the products I’ve help build.

I don’t know exactly how the next chapter reads, but I’m positive using PivotDesk to share office space will be a part of the mix.

 

3 Tips Product Managers Can Use To Do Great Work

Product Managers need to envision the world as it should be while having a clear understanding of how their customers see the world today.

Here are three ways to succeed in doing this as a Product Manager.

1. Understand / Measure
You have a great idea for a feature and a vision of the positive impact building this feature could have on the bottom line.  As the Product Manager, this is a very exciting feeling, you can make the world better!  However, this is precisely the time to be super careful.  Before building, you need to undestand how everything is going to be measured and be able to articulate why the product needs this feature to your team.  If the feature is an iteration on an existing feature, do you have a good benchmark?  If this is something brand new, thinking through how everything is measured helps you elaborate the idea.

Tip:
Create an Evernote notebook for the new feature and add three notes: Benchmark, Business Impact and Customer Stories.  If you don’t feel good about the quality, accuracy and depth of these notes, you shouldn’t move forward with the feature.

2. Talking With Customers
No one cares what you or your company does, they care about their problems and how you will solve them.  During customer meetings, pitch your idea of the future conversationally and then listen to the subtext in what is being said rather than the exact specifics.  There’s a huge difference between what people say they want and how they behave, as I’m sure you’ve heard before many times.

Tip:
Use coffee meetings to have an informal discussion about your customer’s life.  Ask questions like “What are you working on?” and “What would make your job easier?” to get the conversation going.

3. Don’t Forget About Changing The World
Is this you?  Your email is a constant stream of things customers can’t do with your product and examples of how other products are doing things much better.  Of course it is, that’s life as a Product Manager.  A mistake PMs make is turning this input into a todo list for the product and losing focus on game changing ideas.   Remember, you are at the intersection of what your customers need, how your product can help them and how that can fuel your business.  You are in a unique position to envision and empower amazing ideas that get turned into real life and job changing solutions for people.

Tip:
Keep a notebook next to your bed.  When you wakeup with some incredible product idea you’ve been dreaming about, sketch it out.  This will help you be free of the constraints and realities you may face on your team and allow you to think big.

For further reading:
What, exactly, is a Product Manager?
Good Product Team Bad Product Team

 

5 Evernote Hacks PivotDesk Uses To Do More Faster

On the eve of an awesome day 1 of #EC2014 I wanted to summarize a few Evernote hacks our team uses to work smarter and do more faster.

1. Use a @today tag
I forget where I read about this but it definitely wasn’t my idea.  Tag notes as @today and add a @today tag search to your shortcuts.  At the end of each day, think about what you are doing the next day and tag relevant notes with @today.  The next day you are ready to rock.


2. Use an Inbox notebook
I have a notebook called “Inbox”.  The web clipper and email forwarding default to that notebook and sometimes when I’m in a hurry I create new notes in Inbox.  Every few days I “process” the Inbox notebook just like I do with my physical inbox and Things inbox.  It also lives under shortcuts so it’s always top of mind.

3. Use Evernote for Company meetings
I heard this tip from Phil on a podcast long ago.  Every two weeks PivotDesk has an all-hands company meeting and multiple people update the company on parts of the business.  Funnel analysis, KPIs, Customer Stories and a CEO update are all components of this meeting.  I have a stack called “Company Meetings” and a notebook for each meeting.  I invite contributors to the notebook in advance then publish it to the rest of the company the morning of the meeting.  We typically have 5 -7 people attending remotely and the rest jammed in our conference room.  We use Google Hangouts so everyone can see each other and then use presentation mode in the conference room as we talk through the data.

4. Use Evernote for Board meetings
In the past, as we prepared for an upcoming Board meeting we would discuss good and bad things in the business that had happened in the past few months and look forward a few months.  We had a lingering feeling that we were forgotting to tell a fun customer story or leaving something out.  Now, with Evernote, we create a new notebook immediatelly following a Board meeting that we use to capture data points, customer stories, articles and anything else relevant to preparing for the next Board meeting.  This has eliminated the need for a long conversation to discuss what happened in the previous quarter because it’s already captured.  This has been a huge time saver for our Exec team.

5. Use a shared Travel notebook for business development
Our team is constantly meeting with customers, partners and prospects around the country.  As a 20 person company, each of us is very well networked in different ways.  We have a “Travel” notebook that we share, each note is tagged with a city.  If our CEO has a trip to LA in the next few weeks, we will clip LinkedIn profiles, articles and add notes about people to meet with, upcoming events and news in that city.  Our CEO is able to leverage the reach and insights from everyone’s network to plan a productive trip.

About PivotDesk
PivotDesk is an online marketplace that connects companies with excess and unused office space to startups and small businesses that need flexible, month-to-month space to grow their business.

Notes from my Sharing Economy talk to CU students

Watch a video created by PivotDesk showing “A Day in the Life of the Sharing Economy”.  Using car sharing, home sharing and new service models are now the new normal for some people.

Many companies are renting inventory they own.  Technology and insurance innovation enables people to share this inventory.

  • Zipcar
  • Car2Go
  • Netflix

The phrase “access over ownership” is used to describe these Business to Consumer marketplaces.

There are new examples of B2B services such as Getable.

Many companies now capitalize on remnant assets.  Extra office space, under utilized cars and camping gear that gets used once a year are all examples of remnant assets.

These marketplaces enable peer-to-peer transactions.

Leveraging spare time has created some of the most successful sharing economy companies.

  • Uber
  • Lyft
  • Homejoy
  • Rover
  • TaskRabbit
  • Postmates
  • Instacart

Companies considered part of the “sharing economy” are mostly marketplaces.

  • Craigslist
  • eBay
  • oDesk
  • Thumbtack
  • OpenTable
  • Yelp
  • TripAdvisor

Marketplaces characteristics include:

  • Liquidity
  • Curation
  • Ratings and Reviews
  • Frictionless payment
  • Mobile
  • Social Proof
  • Frequency
  • Network Effects

Here’s a quick slide deck I built using HaikuDeck.

https://www.haikudeck.com/p/e4dHuawFSA

And here are a few links I recommend for anyone thinking about marketplaces:

All Markets Are Not Created Equal: 10 Factors To Consider When Evaluating Digital Marketplaces by Bill Gurley

Marketplaces One Pager

Sharing’s Not Just for Start-Ups
by Rachel Botsman

How GTD Areas of Focus relate to Product Management

One of my favorite GTD concepts is Areas of Focus. Using Areas of Focus in your personal productivity system helps group work into context. No need to look at todos like “Get House Painted” when you’re at work. It’s better to look at only work related stuff that you want to be focused on.

For the longest time I’ve had Areas of Focus like House, Family, Marriage, Gear and Travel. I had one Area of Focus for work called PivotDesk. Inspired by a recent webinar on GTD Connect given by David Allen, I decided to refine my work-related Areas of Focus.

Old: PivotDesk

New: Product Management, Feature Development, Product Performance, Product Marketing

As I went through this exercise, I had a chance to think through the different types of work a Product Manager interacts with to get the job done.

Product Management
Idea management, sprint planning, processes, team, budgets, timelines, product roadmaps, internal communication and demos.

Feature Development
Scoping, customer interviews, idea validation, wireframes, designs, details and QA.

Product Performance
Instrumentation, A/B testing, analytics and KPIs.

Product Marketing
Product tour, blog posts, inbound channels, segmenting visitors and drip email campaigns.

I’ve found each of these areas requires a different headspace, pace and communication style. When focused on Product Management, my head is very much in business and planning mode. I’m emaliing, looking at the calendar and updating people. When focused on Feature Development, I am putting myself in our customer’s shoes, feeling empathic and brainstorming ideas. I’m staring at personas and drawings taped to the wall and getting whiteboard marker stains all of my arms and clothes. I’m far, far away from my email and calendar.

What do your Areas of Focus look like?

What I Want To See From The David Allen Company In 2015

I am such a damn fanboy. The #selfie I took with Phil Libin from Evernote at Collision Conf was something I talked about for weeks and the time I ran into Joe Gebbie outside Om Malik’s Design Conf and updated him on PivotDesk was a highlight for me, not sure why. Actually, I do know, these guys have executed on big things that impact my daily life and I admire that.

So of course, because I’ve embraced GTD and experienced the benefits over the years, I’ve become a fanboy of the whole crew, David Allen, Kelly Forrester, Mike Williams and the David Allen Co coaches I’ve interacted with.

But what happens when a fanboy feels let down?

GTD and it’s principals are rock solid in my view. I’ve lived, taught colleagues and survived by some of the concepts in GTD and can never look back. However, the community around GTD is weakening.

Given a system for GTD, or in general just doing a better job at executing on your day-to-day tasks, why care about a “community”? When I started going deeper and deeper into GTD I found myself leaning on gtdconnect and podcasts for inspiration. I realize this sounds lame but I did it and it yielded results.

Ex: During the past 2 yrs…. 1) I had two little kids 2) got my MBA and 3) co-founded a tech startup. I sought comfort in listening to the same podcasts over and over. Something about the iteration, background noise and community felt like a massive advantage I had in my corner.  Do More Faster, Get Things Done, Inbox Zero were things I enjoyed and made me happy….along with producing good results at work and home.

As GTD Connect has faded, Kelly Forrester has moved on and the whole thing seems weak, I still occasionally listen to old podcasts but am now rethinking my approach. I don’t want to move on but maybe I need to.

Ideas

Here are some things to do.

1. Lots of interviews with people in different domains – the interviews with GTD’ers doing amazing things throughout the world are fascinating and keep me paying my monthly fee.

2. More presence. My company PivotDesk is based in Boulder, CO, one of the most vibrant business and tech scenes in the world. If you asked 100 people on the street about GTD maybe 1 would know, this sucks. Why aren’t there more ways to scale the GTD philosophy in a way driven by the David Allen Co? I would help.

3. Better Software. I use Things. My buddy that has no clue about GTD but crushes it uses Wunderlist. My other buddy I’m educating about GTD uses Asana. The smartest engineers on our team at PivotDesk use only PivotalTracker and nothing else to manage their own personal life. I totally get the “tool agnostic” thing but I’m bummed that David Allen Co hasn’t done more with thought leadership around software to support GTD. I’ve reached out a few times to Intentional Software to beta test some of their rumored projects and have gotten zero response. That’s incrediblely lame and a good signal whatever they’re working on will probably suck. I have no financial gain or career gain, I just want to help and got a goose egg…boo!

4. Meetups. A women in Denver has planned a GTD event in which 3 people show up each month. She is trying so hard to make this work and it’s nice/lame. Where is the support from David Allen Co? These people are your evangalists and they have no support/training/kuddos. They are passionate about what you are selling and you are absent. Embrace this crew of people.

I will continue to be a fanboy in 2014. What David has done is amazing and the dude is great. I evangalize GTD, teach people about it, and use the approach every single day. It’s been a life changer.

However, as I look to 2015 I bet I evolve. Continue to pay $48/month for GTD Connect, no. Buy David’s revision, of course. Tell others about GTD, of course. Be a fanboy, probably not.

Mike – keep GTD Connect an exclusive, amazing resource that’s worth paying for and give the GTD amplifiers a voice. Let me know how I can help.

When will it be done?

The physical world has a funny way of revealing insights into the digital world. Earlier in the day the PivotDesk Engineering team demoed a new feature that’s “almost done”. As I walked through our “almost done” new office without Internet, a floor or paint on the walls I didn’t really think things were almost done. It reminded me how varying the definition of done can be and how important it is to define that for any project.

office

We use a MVP approach at PivotDesk and I believe in iterating to make things better and better over time. Walking through our office had me thinking about how much effort should go into projects and when. For example, if our office had an Internet connection we could move in, sit on the dusty floor and start working. We would be in the environment and give real-time feedback like “this office would be better if we had desks and chairs”. On one hand this is true early feedback that should be useful, on the other hand it’s completely ridiculous.

How much effort should you put into the first version of a feature you are building? If a little more effort, polish, investment was made, how would your user feedback change? If the feature was a bit more stable, how much extra time and reduced costs would that provide to the project?

I am confident our office is going to “launch” on time and on budget just as features of the PivotDesk platform do. The trick is finding the optimal time to let the “users” in the front-door.

The Mailbox App is a Great Tool for GTD

I strive for Inbox Zero but am usually not there. I totally buy into David Allen’s GTD philosophy of “Mind Like Water”.  An empty, processed inbox in which all next actions have been delegated, deferred to my projects list or simply done immediately (if < 2 min) is where I prefer to keep my head.  In that state, I make better decisions about what to work on and can focus on “doing”.

The new Mailbox app enhances the processing phase of the GTD workflow.  As you wake up to an inbox with 50 or so new emails as I do each day, Mailbox makes it very easy to archive, delay until later or reply.

20070206-gtd-workflow

The interesting part for me is the delay feature.  You have to make a decision on every email you read and delay empowers you to control the context in which you want to deal with that email.  Yesterday I received an email from a Vendor that had several contracts attached and was a page long.  This type of email nags at me on some level if it sits in my inbox so I touched “delay until later” which will hide the email and show it again in 3 hours.  In 3 hours I knew I’d be at work, most likely in front of my big monitor with headphones on ready to tackle an email like that which needs to be broken down into multiple actions, docs may need to be printed out, etc.  This clarity enabled me to plow through other emails whereas with Apple Mail or other email clients these emails tended to pile up until I was a bit overwhelmed and put off by my inbox.

snoozes-shot

I hope you find some GTD power in Mailbox as I have. There’s a waiting list and it took me two weeks to actually get access to the app from initial download.

 

What Breaks My Heart

HBR blogger Umair Haque has a great post called “Have to Have a Year that Matters“.

In the post he asks “What breaks your heart?”

Follow your passion, we’re often told. But how do you find your passion? Let me put it another way: what is it that breaks your heart about the world? It’s there that you begin to find what moves you. If you want to find your passion, surrender to your heartbreak. Your heartbreak points towards a truer north — and it’s the difficult journey towards it that is, in the truest sense, no mere passing idyllic infatuation, but enduring, tempestuous passion.

When I ponder this, the collection of unsolvable global problems come to mind. But as I think deeper, I realize one common denominator in this collection is a fundamental lack of opportunity, people not getting the chance to try. Being pushed down, discriminated against, facing unfair rules and regulations, no education, no economic opportunity and being blocked by stupid shit that supports the status quo all crush opportunity.  This breaks my heart.

As I look at my own career and co-founding PivotDesk, I realize how connected things are. On the surface, PivotDesk seems like a marketplace for office space, but there’s something deeper. PivotDesk creates opportunity instead of destoying it.  PivotDesk helps companies be more efficient, to waste less and to do more.  We say all the time that “this is not just about office space” and we truly believe that.  PivotDesk is about setting people and companies up for success, doing our small part in helping them do something amazing with their opportunity.

 

 

Late Again

I once heard someone say “When it comes to time, a women getting ready to leave is equivalent to a man saying when he’s coming home.”

In my life, this couldn’t be more true. I suck at being on time, especially when it comes to family stuff and getting home. Everyone I’ve ever worked with sucked at being on time. I’ve had so many conversations with myself or colleagues having one foot out the door knowing they should leave NOW but unable to resist work talk. Even more difficult is spending precious time with friends and wanting to squeeze just a few minutes out of the day to hangout with them just to let others around you down later. (see: choosing to have that second beer at Happy Hour instead of heading home)

Try this exercise, close your eyes and visually levitate over a situation in your mind, clearly understanding how each person feels in their own way (think: scene from Scrooge or overhead view of a RPG game). This is an exercise I try often and rarely achieve success. When you do, it can be powerful. Think about what a pain in the ass it is for your wife, friend or colleague when you are 45 minutes late, regardless of why you are. Use the overhead visualization technique to see that scene in your mind.

When it comes to time expectations, do these things:

1. Choose short term disappointment over long term trust damage.
Get used to over estimating the time it will take to do something or be somewhere. This is as true for your wife expecting you home for dinner as it is estimating delivery of a new software feature. Estimating high will yield short term disappointment but it’s worth it to not lose long term trust.

2. Schedules Matter
In my marriage, I have assumed synchronicity on schedules so many times and been wrong that’s it’s embarrasing. Schedules need to be taken seriously, not just treated as a minor annoyance. Big mistakes can be made by scheduling mishaps.

3. Reiterate. Reiterate. Retrospect.
As soon as you feel like you have your system dialed in it’s probably time to retrospecct on schedules. Never assume you have this figured out because life changes quickly which changes expectations surrounding this.

4. Always Txt
I have gotten in countless arguments trying to defend my guilt riden tardiness when a simple txt would have sufficed. Instead of texting “Running an hour late, sorry.” which would take 3 seconds, I skip that and send a mental message to my spouse that I am not thinking at all about her or the family, when in fact I’m stressed about running late. (I did this tonight which prompted this blog post.)

If you have a career or interest that involves attending after-work events, and you have a wife, family, friends, etc in which you have set expectations, don’t mess that up.

Good Luck. Being on time for meetings and presentations is one thing, being on time for your family and friends requires a different type of discipline.