Wrap Up: My “digital tour of service” with the State of Colorado

Every morning I wake up to the local NPR station (KUNC) playing on my Alexa, grab a cup of coffee, lay back down and listen. It’s a preview of the weeks ahead. Working in state government puts you at the intersection of federal policy and local service delivery. Sometimes things state government builds directly impacts people, and sometimes it enables those in county and local government to serve residents and citizens in a better way.

The Colorado Digital Service (CDS), a team I co-founded with Matthew McAllister, is two years old now and I am wrapping up my “digital tour of service.” CDS is a diverse, cross-functional team of senior engineers, human-centered design specialists, product managers and procurement specialists within the Governor’s Office of Information Technology (OIT). We partner with state agencies to develop and improve human-centered solutions to Colorado’s most pressing technical challenges (and we are hiring).

Over the past two years, I’ve been incredibly proud of the work we’ve done on the COVID-19 response, with the child welfare team, and the new Paid Family and Medical Leave division. I can’t wait to see what the team delivers next.

A few lessons learned

A digital service can be an important tool for governments.

The original vision for the Colorado Digital Service was to create a small team of senior product managers, designers and engineers that would work on the Governor’s priorities and plug-in tightly with the Office of Information Technology. This has mostly played out as expected.

Why is a digital service important for your state government?
1. A digital service creates momentum for new ideas on hiring, software delivery and problem solving that can be leveraged government-wide. Publishing the Modern Software Delivery Index, creating an agile vendor pool and finding new ways to connect Colorado tech talent to government are examples of ways the Colorado Digital Service has done this here in Colorado.

2. For agency initiatives that are emerging, a digital service can be leveraged to prototype, build, ship and continuously improve upon these initiatives until the sunset or transfer into an agency program. Bug Bounty, Digital Vaccine Credentials, Exposure Notifications and Developer Evangelism are examples from the Colorado Digital Service just this year.

3. When brand new agency programs or offices are created, a digital service can help with human-centered design, rapid prototyping, product management and vendor procurements in the early stages of formation. In Colorado, we have seen a new Paid Family and Medical Leave program, Office of Early Childhood Education, and Office of Behavioral Health launch just this year.

A lot of progress has been made to improve the delivery of government services, but we still have work to do.

One of the big takeaways from the past few years in government is that some decades old rules combined with perverse incentives hamper government’s ability to deliver. Everyone wants to make government work better for the people, from tech talent who are curious about working in government, to the career civil servants that have been chipping away at problems for years.

Here are a few things that are gradually improving but need to be better.

Hiring – In Colorado, we can’t hire anyone that lives outside of Colorado, we have outdated position classifications and our product, design and engineering salaries continue to be non-competitive with the private sector. We continue to attract great talent despite these constraints thanks to the tireless work from Colorado’s HR folks and agency directors that find creative ways to staff teams. Refactoring hiring is happening but more needs to be done such as improving how funding is allocated to these positions and competing on salary (read Tips for Finding Ways into Public Sector Work).

Delivery teams – Funding for enterprise applications can be sporadic based on a change in legislative priorities, economic climate or specifics of policy which makes it hard for government teams to hire full-time employees so outsourcing to contractors and vendors is the norm. This perpetuates a “project” instead of “product” mentality of “When will it be done?” and “We have to spend the money now.” In government, many of the technology applications that serve programs like Medicaid, child welfare and public safety are never “done”. Delivery teams need full-time government employees that can focus on delivery with a consistent funding stream over time in partnership with vendors.

Procurement – Governments can have hundreds of enterprise applications and initiatives. How government teams decide to work with contractors and vendors is a huge factor in their success. Although there has been a powerful movement in procurement reform across governments at all levels, moving to a modular, agile way of working is still new in government (watch Waldo’s talk on this). When an program team insists on developing a massive list of requirements to be delivered by a certain date for a certain price and then adds additional constraints such as a vendor having to take on substantial liability for the “system as a whole” or having a certain number of employees onsite, they think they are doing the right thing by “guaranteeing success” and reducing risk. Time after time this approach has been shown to fail (read Government tech projects fail by default. It doesn’t have to be this way).

What’s coming next for government teams is pretty easy to envision

The delivery of digital services across the government is maturing. In some Federal and State Agencies as well as local governments, you will see teams working in an agile way, using human-centered design to better understand the problems they are solving and shipping software that works on mobile devices.

Looking ahead, here are a few things that are either a growing part of a government’s portfolio or coming soon.

APIs – Interoperability between agencies, counties and community partners, open data and giving residents/citizens/patients access to their personal data is a growing piece of the puzzle for government service delivery. We are already seeing states subject to regulation by the Federal government to provide Medicaid patients access to their health information and more of this type of regulation will come. There is also a strong demand from the private sector to access open data sets and have ways to transact with governments.

Layers of Government – For programs that span multiple agencies (CDC and CMS for example) or multiple levels of government (Federal to State to Local), a digital service can help break down silos and glue efforts together. There is already collaboration between states happening formally in monthly working groups and informally across networks of peers. Governments at all levels should be working as a portfolio in many of the large enterprise applications like unemployment insurance, Medicaid and paid family and medical leave sharing open source projects and reusing composable building blocks instead of paying the same vendors to duplicate software applications over and over for each state.

Machine Learning – Fraud detection, robotic process automation, public health outbreak prediction and so much more is coming to the government. Understanding how to manage ML pipelines, train models, and incorporate all of the ethical considerations that this technology will raise for a government into the product management process will be critical. Digital service experts that have experience training and deploying models or designing product features that leverage these models will be important. [read Digital Services to APIs to ML]

Onward!

After 20 years building software in bootstrapped small businesses, venture-backed startups and large enterprises, I feel incredibly lucky to have stumbled into government and fallen in love with the work. My work-life has never had more purpose that it does now and I’m excited to continue chipping away at these problems.

Thanks to my Colorado Digital Service teammates, Governor Polis and his team, and all of my colleagues in the Office of Information Technology and within the agencies for helping the Colorado Digital Service get off the ground and become an important part of service delivery to Coloradans. I am grateful to you for giving this idea a chance.As for me, I’m boomeranging back to the US Digital Service to serve another digital tour of service taking my learnings and inspiration from Colorado to the Federal government.

Glenmont to Farragut North

Beautiful, sad, newspaper, phone
Looking down, looking around, tall, short, fat
Hurting inside, motivated, exhausted, music
Glasses, hat, old, new, style, healthy, loving
Depressed, arms open, arms crossed
Friends bump into eachother and hug
Guy with a ponytail stares mindlessly at his phone
Girl with sad eyes daydreams

I’m Joining the U.S. Digital Service

I have never been particularly interested in Government, Civic Tech and Politics with the exception of reading the Sunday NY Times, watching Meet the Press occasionally and being somewhat interested in the Open Data movement.

A year ago I had a conversation with Susannah Fox about AI, Healthcare and Aneesh Chopra’s book “The Innovative State“. I was inspired and began digging deeper into the intersection of Government and Technology. I learned about 18F, Cloud.gov and played around with datasets from data.gov. I watched hearings on the OPEN Data Act and subscribed to newsletters from Think Tanks like the Center for Data Innovation.

As it turns out, there’s an incredible amount of innovation and goodness happening in Government today from the use of open source to data transparency to progressive tech policy.

Susannah connected me with the US Digital Service, a group of Engineers, Designers, Product Managers and Digital Policy Experts that work across the Departments of Homeland Security, Veterans Affairs, Defense, Education, Health and Human Services, and the Small Business Administration to improve websites, access to datasets, user experiences and more. It sounded awesome and I decided to give it a go.

An election, a hiring freeze, a few background checks and many interviews later, I was accepted into the program. My wife, kids and I are relocating from Denver, CO to Washington, D.C. for a year long “tour of duty”.

Learn more about the US Digital Service and how you can join!

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Stapletopia

Friends ask me if I like Stapleton and I tell them a story about how I once vowed I would never live there. I wanted to be in a ski town or a loft downtown, never in a lame, boring, family type neighborhood.

Like most things in my life, every few years I look back and realize what an idiot I was just a short time ago. Obviously, I have changed my tune about Stapleton and couldn’t be happier calling the neighborhood my home. With two little kids, my priorities and lifestyle have also significantly changed.

Stapleton is easy livin’. Walking to the pool, cruising around on bikes, going for runs and hikes on trails, bike commuting to downtown….it goes on.

If you’re interested in the neighboorhood or showing your friends around, this map is my recommendation for experiencing Stapleton. Definitely use Zillow to checkout house prices, etc and remember that April and May are when a lot of houses come on to the market in Stapleton. I’m no realtor (talk to Pam Rios for that), so this knowledge is based on anecdotal observations.

The Stapleton Tour

1. Stop at Starbucks at fuel up. Yes, Starbucks. I know it’s not hip but everyone is super nice and it’s easy. If you’ve never been to a Starbucks because you are so incredibly hip, order a Clove, it’s like a pour-over.

2. Cruise down 29th ave to get a sense of the mixed architecture styles. You’ll see super modern, townhouses, regular houses, apartments, etc all on the same block. Turn right on Central Park then left on 26th. Checkout the rock climbing park, one of a zillion playgrounds for the kids all around the neighborhood.

3. Continue on 26th and wind around Westerley Creek Elementary. Yes, Stapleton schools are good. The PTA and parent support is super strong for the several middle schools in the neighborhood.

4. Wrap around back to 26th again and cross the Westerley Creek open space. This is a great place to run and ride bikes with the kids.

5. Turn left on Fulton street, you’re now in the East Bridge neighborhood and my stomping ground. Turn right on 28th and drive another block to see a park with a playground and pool. There are several of these around Stapleton.

6. Continue East on 28th and turn left on Iola St then right on 29th. Drive a minute and you’ll see the Bluff Lake Nature Center on your left. Turn into the parking lot, get out of the car and walk around for a few minutes. This is a great place for running or hiking with the kids.

7. Get back in the car, turn right out of the parking lot and wind around, you’re now on MLK blvd again. Drive a minute and look to your right to see the Central Park Rec Center. This is a great gym with yoga classes, lap pool, kid pool, etc.

8. Keep going on MLK another few minutes and look to the right again to see Central Park. This is a great running, sledding, bouldering and kite flying park with a huge playground. You’ll see road races on the weekends and an occasional cyclo-cross race in the fall.

9. Turn left on Unita then right on 29th to see the Bistro and Wine Cellers at Stapleton. This is your amazing lunch or light apps and glass of wine conclusion to time well spent touring Stapleton. In the summer, cruiser bikes and craft beer dot the Stapleton landscape. If it’s Fri or Sat between 4p-7p stop in the Wine Cellers for a free tasting.

10. Turn right on to MLK then left on Central Park Blvd to head towards I-70. You’ll see the old Stapleton tower and a new neighborhood called Central Park North. On the left you’ll see the RTD bus stop and the new light rail station, it’s super easy to get to DIA from Stapleton. Cross the bridge and you’ll see a gigantic outdoor mall called Northfield. That’s where Target, Bass Pro Shop and stuff like that is. (see “Last minute xmas shopping”).

Good Luck in your Stapletopia journey and feel free to reach out with questions.

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.

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.

Great Jason Calacanis Riff About Boulder, CO

In an interview with Kindara, a Boulder based startup that helps Women monitor fertility, Jason Calacanis discussed Boulder’s business culture.

“The thing about Boulder is everybody is so damn smart and fit and active and intelligent and friendly, it’s absolutely disgusting as a New Yorker but God, you go there and people are like How Can I Help You and Let’s Have An Interesting Conversation and I’m well read and I’m fit and let’s go for a mountain bike ride and talk about the NY Times I just read cover to cover.”

I love this rant. With Techstars Demo Day a week away, it’s a good time to reflect on the unique ecosystems like Boulder. The Work-Life Balance, Entrepreneurial Density and Exciting Tech Scene make the days fly by and my personal productivity much higher. Techstars is a prime example of the support a Community can provide, this summer has truly been inspiring. I’m just happy to be a part of it all. Thanks for the kind words @Jason…and if you’re wondering, Yes I had Tofu today, read the NY Times and am running a 1/2 Ironman on Sunday to clear my head before Demo Day Aug 9th 😉

Discussion of Boulder, CO starts around Minute 20 of this interview.

10 People that Influenced my Career in 2010

This is the most procrastinated post I’ve had, but wanted to put it out there anyway.

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As a great year comes to a close, it’s fun to reflect on people that impacted you in some way, here’s my top 10 list in no particular order.

Mark Suster

I found out about Mark when he began hosting TWIV. This is now my favorite podcast, I watch it either on the plane or in my basement on the Apple TV. Mark’s knowledge, attitude and passion for his industry is inspiring and motivating. Thanks Mark.

Brad Feld

Ever since I met Brad he’s been a huge source of motivation to me. The type of motivation Brad brings is unique, it’s practical motivation. I have learned more tactics (Morning Think, Life Dinner, Do More Faster) from him than anyone else thus far in my career. Thanks Brad.

Ninan Chako

Since our company was acquired a year ago I’ve been on a ridiculously fun ride. Ninan, the CEO of PR Newswire, asks questions constantly, loves what he does and generates energy whenever he comes to Denver. I am having a great time working for and learning from you Ninan, thanks.

Mark Solon

I met Mark somehow this year via Twitter and can’t think of anyone I barely know that I have more in common with: tech, skiing, biking, investing, family. Mark’s story is awesome and his career situation is one I’m striving towards. Thanks Mark.

Rob Johnson

The project my team began this year involves big data and semantic goodness. I had talked with Rob face to face once before during the 2009 Triple Bypass bike ride around 11k ft at the base of Loveland Pass. This year I have talked with Rob and the GNIP team weekly getting a full blown education in API terms of service, rate limits and the activity format which has been crucial to our success. Thanks Rob (and Jud and Chris).

Dan Primack

I signed up for Dan Primack’s daily email this year (thanks Mark Solon) and have felt more in touch with the PE and Venture Capital industry than ever before. It is the most informative email I get every day, easily trumping any NY Times or WSJ email updates, etc. Thanks Dan.

Vivek Wadhwa

I have never met Vivek and have only seen him speak once, at the Defrag Conference this November in Denver. I talk to people almost daily and cite points from Vivek’s talk about creating innovation culture. Thanks Vivek.

Howard Lindzon

2010 began by dialing into an 8am skype call with Howard on New Years Day, Jan 1st. I was surprised when he suggested that time but then realized this is how people that are motivated, successful and driven role. Time, place, space….these things do not matter to people like Howard. Thanks for starting my year off right Howard.

Jason Keller

Jason was a co-founder of The Fuel Team, acquired by PR Newswire in 2009, and ran global products for PR Newswire for a year. We have been working side by side for 8 years but this year was especially fun. Jason’s work ethic, personal organization, family focus and drive is a huge motivator for me. Thanks Jason.

David Allen

I’m not sure how I learned about David Allen’s Getting Things Done but it has absolutely had one of the most positive impacts on my work and personal life than anything else in the past few years. I have his podcasts, specifically the Guided GTD Mind Sweep episode, at the ready. I use Things for the Mac throughout the day and have used many of David’s ideas to optimize my personal and professional life. Thanks David.

Lists are a funny thing. If I had titled this “the top 20…” then I would have written about amazing people like Micha Hanson, Elliot Turner, Keith Hunniford, Chad Fowler, Fernand Galiana, Paul Kedrosky, and Rod Nicolson. As I finally post this in 2012, it’s fun to see who I’m still working with, who is still a big influence and who has faded from my life.

Using GTD Agendas and Life Dinners to improve your relationship

My Wife Sarah and I try to have Life Dinners every month. It’s a great time to organize, talk about upcoming trips or things we want to accomplish together. Recently we have found ourselves with little to talk about related to life tasks and schedules as we leverage basecamp and email for passive communication about life stuff. However, passive communication can get overwhelming at times. I have found myself barraging Sarah with emails about various life tasks which stresses her out and creates the same problems we were trying to solve with the Life Dinners.

A few weeks ago I attended the “Mastering Workflow” GTD seminar. This was mostly review for me but the tactic of using “Agendas” really stuck. In Things, there’s a “People” list that I have never leveraged before. As life tasks crop up that I need to discuss with Sarah, I associate them with her in the Things and wait until our Life Dinner to discuss. I also do this with my boss as we have a weekly video chat standing meeting to review anything outstanding.

Using Agendas is a great way to cut down on daily email and task switching while still feeling organized.