In my first post, I covered several CTO stereotypes. This is the first in a series of deep dives to better understand and learn from these stereotypes. Now, let's dig into The Side Quester.
The Side Quester gets caught up in unimportant details or side projects. They may be drawn to complexity, novelty, or immediate gratification (reacting/firefighting). Qualities like perfectionism, avoidance, or curiosity can get them (us) into trouble.
Side Quester Traps
A few of the traps Side Questers fall into:
Too Comfortable - You are comfortable as an expert. In fact, your previous success probably came from you being an expert. Now, you may no longer be an expert and have to become a beginner again. Being a beginner is uncomfortable work, so slipping into comfortable work is tempting, like taking control to “make things happen faster.” This results in you not doing your actual job but doing other people’s jobs instead. Comfort can also look like focusing on your strengths (a good thing) as a justification for staying away from hard things. Embrace the hard things and the beginner’s mindset. Get comfortable with that uncomfortable feeling of staying the course and doing your job, not getting sidetracked doing the jobs of others.
Reactive Firefighting - Going on unintentional side quests, but side quests nonetheless. The whirlwind happens, and we follow the path of the current urgent issue – and we let it take over. Some firefighting is necessary, but not intentionally limiting resources spent on firefighting will cause the firefighting to overshadow the actual work that needs to get done.
Bad Timing: Solving a real problem with a brilliant solution—that isn’t that big of a problem right now. I have fallen into this trap a few times. When you find a great solution to a problem, you want to implement it! You can improve the process, eliminate inefficiency, and make things better. However, it might not be the right use of resources in the current business context - it's just a tempting side quest. Future theoretical problems are usually the culprit here – they aren’t problems yet, and many will never be problems! Humans are bad at guessing what the future holds - be extra careful anytime you are predictively buying software or implementing solutions for future problems.
Each of these traps can hinder your business's progress. True progress demands ruthless prioritization—but not just prioritization—alignment has to occur with business goals so that you aren’t just doing the right things but doing the right things at the right time.
The Side Quester In Real Life
The Comfortable Academic Quester
A friend told me this story:
“Our company brought in a new technology leader. Before he started, the team struggled with discipline and getting work done, and the business was losing trust.
The team was used to having near-full autonomy and viewed themselves as slightly superior to most of the rest of the organization. They were working on more difficult, sophisticated problems, so they deserved space to work and need not be bothered with work that was beneath them.
The new leader was brought in to improve discipline and communication and deliver more meaningful business results. The leader got off to a good start. He correctly identified a trust problem with the business and needed to restore it. But then the side quests started.
This leader decided the way to restore trust was through external validation of expertise. The logic was: If I can get my team certified by a third party that they know what they are doing, the business will start trusting them.
Needless to say, this didn’t go well.
The team quickly learned that if you showed up to the study sessions and worked on your certification, you could do whatever you wanted. The team clearly took advantage of the situation. Also, the leader really enjoyed the process of getting complex engineering certifications (since they are hard to obtain), and he lost interest in the original purpose of the role.”
Drifting toward comfort and solving the surface problem instead of the deep problem killed this opportunity. Unfortunately for all, the leader got fired, and the team was dismantled.
The Optimistic Futurist Quester
This next story is my story. Several years ago, I was on a quest to implement dynamic pricing on a very large e-commerce website with 30k+ SKUs. I knew that Airlines, Amazon, and others had solved this problem, so I figured it was a solved problem for e-commerce – just a Shopify app install away.
I was wrong.
The high-level business value alignment was there. It was the right thing to work on to move the business forward. However, the timing was off for the solution. There wasn’t a button-click solution (that actually worked) available to solve pricing for a large website with B2B and B2C traffic that included highly competitive products (multiple sellers) and unique branded products. Nor was there a solution that accounted for items with sparse sales history and item category groupings that were wrong.
Again, this wasn’t an unsolvable problem. I talked to companies that specialized in pricing that could have solved the problem, but they weren’t button-click solutions and were prohibitively expensive.
My mistake was taking a software side quest before we deeply understood the problem. I wanted a software solution to work because that was easiest for me (and my team). The best solution (at the time) was having an analyst dedicated to pricing with tools to help enable research and pricing updates. It was not nearly as fun, but it was the right solution and made a huge impact.
The Cost of Side Quests
Internal Cost
Ill-advised side quests lead to wasted time and effort, but the largest impact is eroded trust. Lack of trust from the business creates lots of problems:
Hard to get funding for future projects - No trust tangibly translates into less money for innovation/initiatives. This correlation isn’t always the given reason, but it is a huge factor. Every project is a bet by an owner/investor; if they don’t believe in the innovation, they may not want to move forward, but they also may not move forward because they don’t believe in the people.
Discouraged team: The team feels that it isn’t making a difference. If they don’t feel like they are contributing, it's hard to have a productive team.
Carefree team - Sometimes, teams think things are going great and have no idea (or don’t care) if they are contributing to the business. This is how teams get dismantled if the leader doesn’t fix it.
Complexity
Sub-optimization is another cost. Sometimes, a side quest isn’t an obvious failure - but it leads to more systems to maintain or additional unneeded complexity. These aren’t huge immediate problems, but quest after quest, they become problems until somebody says… let's just start over.
External Opportunity
External opportunity cost is often even larger than the internal cost. External costs include:
Customers not seeing progress - Customers expect you to improve over time, and when they don’t, they assume stagnation—or worse, regression.
Lack of partner confidence—Just like customers, partners lose confidence and stop investing in your vision (and no longer recommend you), making it harder to grow.
No Momentum—Both of these problems translate into a lack of momentum / visible progress, which causes the team to get stuck. Momentum is hard to sustain once support is lost.
These costs impact perception as well as real outcomes. Market opportunities are perishable, and every delay gives competitors a chance to get ahead. The cost of inaction or misdirection isn’t just the effort spent—it’s the value of everything that could have been if the focus had been maintained on the right things.
Avoiding Bad Quests
Tips for self-aware CTOs
It's hard to be objective, and it's hard to take time to stop and think. The best way I know to do this is to:
Write out your business's goals (try to come up with them if you don’t have any formal goals).
Describe how you and your team can help with the business's goals.
Put all ideas and initiatives through this framework (using something like OKRs can be helpful), but it's more important to actually do this!
Boring right? Ya - it can be, but it becomes exciting when you see it work!
Lastly, you should still spend some time experimenting and learning - doing trials and pilots, trying new things, etc. However, don’t let them devolve into an ill-advised side quest! Be willing to kill these projects quickly if they won't bring value or would be in conflict with other, more important things.
Tips for Other Executives and Boards
CEOs - Create a strong vision and tirelessly communicate what needs to be done. Also, work on guiding principles to help determine what should be worked on versus not.
CFOs - Push back on technology spending - require strong business justification, but be open to change. This is a tricky balance; on the one hand, you want to be a good steward of company resources, but on the other hand, being too heavy-handed may result in a lack of innovation and cost avoidance that is detrimental to the company's future.
Board of Directors - Set reasonable expectations for growth and profit. Also, don’t condemn reasonable efforts that everyone presumed would be successful but were not. Share your past mistakes and help the current executives avoid making them!
An occasional side quest can be fun - that doesn’t make you a side quester. It's okay to experiment and invest some resources in risky projects. You also don’t want to kill curiosity, but you do need to focus the majority of your efforts on the projects that have the best chance of making a difference for the business!
“But We Have to Do Something!”
CTOs should be willing to stay focused and not change things when it's not the right time. Just because you can change or improve, it doesn’t mean you should. Also, don’t underestimate the non-monetary cost of change. Free isn’t free when change is involved. If you love change, realize that most people don’t like change. Use your change dollars on things that will make a significant impact.
Lastly, one of the biggest lessons I have to keep learning is that sometimes, the right thing to do is nothing. When asked about investing tricks, Warren Buffett said, ‘The trick is, when there is nothing to do, do nothing.’ It’s a simple yet powerful reminder that patience is often a wise strategy.
Next time you hear the voice in your head, “We have to do something!” Realize— you don’t. You can actively choose to do nothing and stay the course, avoiding the lure of the side quest...
Opportunity cost is the biggest losses. Like most things, you can only achieve freedom through discipline. When you are constantly going on side quests you don't have the freedom to take advantage of the big opportunities