From Old to New

A personal transformation journey

I talk a lot about transformation. In fact, almost every conversation I have with IT leaders is about a journey going from old to new. Whether it is about a change in thinking, a nudge to the culture, or a shift in process, the theme is always about the introduction of something new.

New appears like a novelty, something shiny and attractive at first. At the same time though, the primitive parts of our mind take hold and recoil from the novelty, like the body fights off a virus. The new is chaotic and unknown while the old is comfortable and tangible.

I talk about some of these transformation stories on this blog. Often the results are dismal because for many enterprises, it’s hard to let go of what already exists and is well known. To succeed in any transformation, you have to be comfortable with being uncomfortable.

I was originally going to title this post “Stack Overflow has a Stack Overflow”. Sure, not a great techie joke, but in a sense Stack Overflow has also been undergoing its own transformation. You may have seen this in the more overt way they present their business offerings on the site. They changed how they package and sell their solutions. Stack is evolving from the quirky startup with unicorn dolls in the lobby to a company that wants to be a unicorn.

This has not come without its challenges. With their founder, Joel Spolsky, stepping down some months back, the leadership vacuum has meant missed opportunities, slow decision making, and questionable strategic choices. The vision to the market is confusing, relationships with moderators strained, and product direction rudderless. They have lost many smart, honest, and dedicated folks in the past year, included one person they let go that was the heart and soul of the community. Meanwhile, the business itself has not matured nearly enough to support the transition.

They recently ushered in a new CEO to the company. He will be tasked with filling the void of leadership and fixing the current “overflow” with a proper memory flushing. Of course this will introduce even more changes to come, more turnover, and more near term turbulence.

This also means the end of my time at Stack Overflow.

Yes, I decided to leave a company that I have passionately boasted about for the past three years. From starting with a mere concept to launching what has become the fastest growing business, it has been an incredible honor to be part of the Stack Overflow Enterprise team. I still proudly wear the T-shirt 😄

Just hanging with Kent Beck at YOW! Singapore…

But why leave? I have no fear of the uncomfortable, which has perhaps been the defining thread of my entire career. I like to push the boundaries, try new things, fail and pick myself back up again. That was what attracted me to Stack Overflow in the first place, and what led to my recent adventures building a local presence and business in APAC. I love building things.

The strategic direction for Stack Overflow however is to pull back from some of these initiatives like APAC expansion and refocus the business. I cannot entirely blame them given that global expansion is incredibly difficult, time consuming, and expensive. It’s a long term strategy that requires patience, planning, and perseverance. It will be up to the new CEO and leadership to decide when it is the right time to invest in the region, though I suspect that will not be any time soon given all the other challenges before the company.

I strongly believe in APAC however and the opportunity to make a positive contribution. Sound advice on business and engineering transformation strategies, collaborative innovation, and developer culture are woefully in short supply. Being someone that has been involved and seen transformation projects across many industries and companies, I am looking to bring some insight and much needed guidance to organizations in the region.

My talk on collaborative innovation in Ho Chi Minh City

This is the start of my own personal transformation. I will still write this blog weekly, the Heretechs podcast has been released with our first six episodes, and I continue to travel the globe giving talks, meeting companies, supporting developer communities, and advising IT leaders. I am passionate about the potential to impact organizations through the tools of digital transformation, innovation strategies, culture change, and community building. The only difference is that I will be doing this under the DEV.BIZ.OPS moniker.

If this post feels self-indulgent, it’s because it is mostly about me and my situation. So to get back to why you read this blog in the first place, let me share a perspective on transformation and the process of making difficult choices. This is a framework that has served me well when making significant and life impacting decisions:

  1. Start with your “Why” — We rarely take time to consider what feels true to ourselves. Take time to introspect and understand what feels most aligned to your passions and experience. Your NorthStar will clarify any significant decision you are presented with.
  2. Frame decision as a choice — When you narrow focus on the issue at hand (should I leave my job, do I want that promotion), you tend to forget that there are probably many other options that you have not considered. This also gets you out of the mindset of thinking about the “problem” and resetting around “opportunities”.
  3. Brainstorm on various options — Once you have as least one choice identified, let your mind wander to think through various possibilities that could pose interesting future paths. The creative effort will open new avenues that you have not actually explored when you were narrowly focus on your “problem” mindset.
  4. Envision what success looks like for each option — With options identified, consider what positive outcomes would come from selecting each option. Explore under what conditions the choice would deliver those positive outcomes.
  5. Consider barriers to each option — Just as for success, envision the roadblocks and the negative outcomes that could evolve from deciding on each option.
  6. Test each option as feasible — Are you able to probe each option to see the results of making a decision for a particular option? Even if this is not feasible, thinking through the test conditions can help guide you through the execution of a chosen decision.
  7. Make a decision based on the data — Going through this exercise would not be worthwhile if you simply relied on your gut. Use the work you have done to explore options and the outcomes of those options to arrive at the most sound decision.
  8. Realize nothing is ever final — Sunk cost fallacy often guides us to continue down a path even if the outcomes are clearly trending negatively to expectation. Though it might be painful at the time, reversing a major decision is often the most sound strategy.

Thanks for all of your support, advice, and friendship during this transition. If I can be of help to you, your team, or your organization, I would welcome the opportunity to support your transformation initiatives.

What is your approach to decision making from a professional and personal level? How does your organization go about prioritizing strategic decisions?

Can I talk to my rubber duck at work?

https://workplace.stackexchange.com/questions/83451/can-i-talk-to-my-rubber-duck-at-work

Just don’t let potential hiring managers know during a job interview…


We help IT leaders in enterprises solve the cultural challenges involved in digital transformation and move towards a community based culture that delivers innovation and customer value faster. Learn more about our work here.

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