Let’s Start by Cleaning Up Your Room

The building wasn’t anything special. The open office format wasn’t an issue because we weren’t living in a future state or what is better known as the present moment.

The people were nice and most of the time there wasn’t a feeling that everything had to be done for no particular reason. Yet, when things needed to get done there was chaos and panic! Everyone would be running around, firing off emails, trying to figure out how to contribute yet keep their heads down and not be a target.

This feeling made no sense to me, based on the environment and areas we were trying to solve for.

Frankly, I found the hysteria somewhat comical. It reminded me of a Monty Python skit like the Holy Grail. The “knights” were very serious. They envisioned themselves to be embattled individuals who believed they were on the most important of quests. While at the same time it felt like with all the chaos you always had someone bashing coconuts mimicking the sound of a stampede of horses.

Don’t get me wrong, I’ve been the knight in that skit. I wasn’t so much laughing at anyone in particular, but more about how I used to view myself. I was laughing at me… and them.

As an aside, this wouldn’t be the last time I jumped up on my high horse. Sometimes we learn and grow. Sometimes we dig in. It’s always better to take the former perspective. The later makes you look silly and frustrates everyone around you.

I learned that the chaos would soon subside. I also learned from people with far more experience than myself that if they wanted to change the outcome, they would have to change the script; and that wasn’t going to happen. There were too many knights in this organization and we had an unlimited supply of coconuts.

My VP walked onto the floor with purpose. They locked eyes with me and took a direct line to my desk. “There’s no support for this approach!”

Wait. What? How did I become the target?

“Well of course there’s support!” I replied with equal intensity. My team’s body language recoiled in horror like they were saying collectively, ‘Ohhh … rookie mistake!’.

They paused for a second and then began to counter attack. “No, there isn’t any support from the executive team. You’ve been working on this for six months and I just got shut down without so much as a discussion.” I rolled my eyes and stood up. I know I shouldn’t have done that – roll my eyes – but it was a natural reflex to people in authority who feel the need to ‘inspire by fire’.

Clearly they were frustrated and understandably so; however I had been busting my ass for six months and they hadn’t asked for any updates. At no time did they bring me into the room with other stakeholders. My thought immediately jumped to, “Who the hell was this individual to speak to me like that in front of my team?”

In retrospect there were many mistakes I made throughout this process and not updating key stakeholders was one. Another was the realization that this was my VP’s team. They were ultimately accountable. While I was responsible for the path forward, they would shoulder any failure or negative outcomes.

There was a long pause. I tried to take a different tack. “If I may? Let’s step into a meeting room and I can explain.” They glared at me. “You’ve got five minutes.” At this point I felt like was walking into a scene from Scarface and Al Pachino was not happy. Obviously he didn’t have a gun but I thought I might be getting fired.

I took a deep breath.

“I have all six team leads aligned. If you go back to your meeting I will get them to come down and I can explain the approach. You have buy-in for the strategy. It’s the template for proposals I was provided. It’s structured like a business process document crafted by a multi-million dollar consulting firm. I can’t tell the story of the work that needs to be done using a 50 page if/then statement.” I would soon learn the irony of that remark.

They took a deep breath.

“You have ten minutes.” They opened the door and left. I waited for a minute. I’m not sure why I paused. Perhaps I was just collecting myself. Perhaps I was trying to look calm in the midst of the tornado of activity that just blew through the office. I can’t recall what made me move from 0 to 60 but I quickly snapped out of it and jumped on the elevator.

I rounded up the six leads and booted it down the stairs to the meeting room. I had a few minutes to catch my breath as another project was being discussed. Eventually all team leads walked into the room.

“Thank you for your time everyone.” I’m not sure why I opened with that line. It felt like I should be apologizing for nothing in particular. It also felt like I was pitching them on a strategy to get the technology they invested in working efficiently. They weren’t framing the problem from the perspective I was about to provide, which I believed would help them realize the ROI they were promised by the enterprise software company.

I recall thinking ‘this better work. I’m swimming way outside of my lane. Here goes nothing.’

“How many of you have children?” The room came to a quick stand still. My VP’s jaw dropped. Literally! I can still see it fall down in slow motion. Ever insistent I forged on, “Indulge me. Hands up! Who has kids?” They all raised their hands.

“Great! Now imagine your child coming home from school one day proclaiming, ‘I’m never cleaning up my room again!’ And they don’t… for seven years!”

One stakeholder started laughing. “What’s funny?” I asked. “I’m sorry, but when my child doesn’t clean up their room I can’t see the floor after a few days!” The room lightened as everyone could relate.

My VP was still not smiling. The team leads in front of me began shifting restlessly, whispering to one another. I knew I had to reassure them as well, so I pressed on with the metaphor.

“Exactly! The concept is the same with your information. No one can find anything because in seven years no one has put any thought into organization or governance. Put aside the document you gave me to explain this approach and forget about your opposing technical preferences, at least for the moment. What I want to do is an inventory of everything – all documents, web pages, audio, video – literally everything. Essentially I want to clean up our respective ‘bedrooms’.” They still looked a little confused.

My VP was losing his patience. “Jeff, we don’t have time for this get to the point.” I nodded in their general direction and carried on.

“If we can have the leads do that work – which they’ve agreed is the best approach – we don’t have to worry about technical issues and you can lead with a single strategy around what we publish over time.” The team leads relaxed and smiled in agreement. My VP leaned back thoughtfully looking upwards, as if pondering the idea.

I continued. “Again, if we take the time to inventory everything and put governance around what, why, and when we publish, the organization can be unified and you can realize the ROI on the technology you just bought.” The executives were now leaning in with interest.

“I want to create a situation where I could pull a 12 year old off the street hand them a plain language document on where to find your kids report card from grade 10. In this scenario they would not only be able to easily find the report card, there would only be one version, not 50 as we have now with so many pieces of content in so many different, yet connected spaces.”

Everyone got the metaphor and the strategy. I left it to the team leads to outline details and the timeline over the course of coming weeks and months ahead.

No one asked me to revise the business proposal. Not that I could. Again, they weren’t asking the right questions. I mean, they were from their perspective but they were looking at the tool without considering the output. That is, the output is what the tool was promising to deliver, but it couldn’t do that if we just dumped our mess into the product. It didn’t have the intelligence to make that happen. Most tools still do not.

To be clear, I wasn’t arguing for or against any design discipline. I wasn’t commenting on the technology or the people in the organization. I just wanted to get everyone doing the right thing, at the right time, in the right way, with the right feeling the first time. Hawaiians have a term for this – they call it Kina’ole. It’s a philosophy that, unbeknownst to me, would drive my approach to business in the years to come.

At the time I didn’t get why this meeting was such a big deal. In retrospect I realize what I had accomplished was bigger than the promised ROI or making my VP look good. It was that I achieved alignment. This would continue to be the biggest fundamental challenge in my career. It’s disconcerting that it has been, but that’s the reality of the complexity of the machines we’ve built and continue to grow.

About a month later I was asked to attend a meeting by one of the stakeholders who was in the room when I was presenting using the metaphor of a messy bedroom. There were three people I didn’t recognize when I walked into the room. I didn’t have a good feeling but I quickly brushed those thoughts away.

“Thank you for your time.” The stakeholder opened with the same line I did. My bad feelings started to come back. “I think in order for teams to find things, we need to get organized. The work to be done would be analogous to cleaning up your basement.” There was a printed deck with a messy basement and the next slide was a clean basement. I knew where this was going. What wasn’t clear was why was I in the room?

They finished presenting their deck – which mirrored my own. I didn’t care. I honestly didn’t. In fact I’ve never cared about recognition of ideas; as long as we are aligned, I’m good to go. However, while I gained alignment I also changed the strategy. A strategy that would not benefit me.

Should I have cared more about who got credit? No. If I did my future would be forever changed and looking back I can’t say that would have been for the better.

“I’d like to introduce you all to our new contractors from the multi-million dollar consulting firm who will be leading this initiative.” I began thinking in one word syllables. “What?” “Why?” “Really!?”

They began asking questions to try and get an understanding of next steps. I outlined the work to date and the best path forward. They asked more detailed questions. I answered all of them. They assumed I would be their team lead on the ground. One of them actually said, “That’s great Jeff. Can I assume we’ll be working closely with you during the contract?” They were wrong. I didn’t know it at the time, but I was done.

I heard a gentle knock at the door as the meeting was wrapping up. It was my Manager. “Sorry for the interruption. Jeff can I borrow you for a minute?”

My Manager took me out for lunch. I asked some pointed questions and they answered directly and professionally. “Am I being let go for doing my job?” I asked. “Let’s put it this way. In doing your job you inspired the stakeholders to put their budget elsewhere.” They paid for lunch. I went back to the office and wished the team well.

It was the summer of 2003. It was a time in my life where I had lost a lot personally and now professionally. Yet in this loss I felt a weight lift. I was forced into a kind of minimalist mindset and lifestyle. I knew I needed to take some time for myself and get back to creative pursuits.

One morning, a couple of weeks later, I stumbled across Adam Curry. He wasn’t crazy but he was talking to himself. He was publishing something called a podcast. His blog was a simple bullet point list of topics and a tagline read, “there are no more secrets, only information you don’t yet have.” Though Adam is nothing of a futurist, I began to think further out because of the ideas he shared and that one tag line on his blog.

Field Notes

Nearly twenty years ago I started by simply asking a company that employed me to consider a metaphor instead of sticking to their own mental models. To begin by getting aligned. To consider solving a problem from a different perspective. To ask more questions rather than assuming any one individual or team had the best answer.

What I lost in employment I gained in so many other areas that extended well beyond design, code, and business.