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The CTO’s Golden Derrière: The misguided perception of rockstar tech leads.

Phil Bennett Posted by Phil Bennett in Uncategorized 7 min read

Over the last couple of decades, the explosion of tech companies led to their leaders being idolized as people with superhuman capabilities; Gods of industry, savant business leaders with visionary missions to change the world.

However, they’re simply not much better than you or me.

People love to use the analogy that your career is a ladder that you climb. You’re forever looking up at those above you, seeing the back of them as they climb up ahead of you. If you’re lucky you can also see the back of your leader’s leads in the distance at the top of the ladder.

For the last couple of years, I’ve been looking at the rear view of my CXOs and the directors of engineering that report to them. And I can tell you they look remarkably similar to the backs of everyone else around me!

Exponential Competence Curve

There’s a common perception that the capabilities of people increase exponentially as they get promoted. But what I’ve noticed is, that in reality, the people above me are a little bit better than me, with a little bit more experience. Just like the people who report to me are only a tiny bit less experienced than me.

Instead of this exponential increase toward becoming a legendary CTO, most people make smaller incremental steps as they learn, develop, and get promoted.

Sure there are outliers, people like Steve Jobs and Bill Gates buck this curve. However, these are almost mythological creatures, they are not the norm, and they aren’t the type of people 99.99% of us will be working with.

The Golden Derrière Dilemma.

The problem with this idolization of the C-suite and top-level management comes in the fact that when assessing their actions most people will assume there is a lower chance these people are making mistakes.

When a CXO takes an action or makes a decision, it will frequently have a global impact on a company, impacting every employee. If the people don’t agree or are hurt by these actions they will tend to assume the CXOs with the ‘Golden Derrière’ will have chosen this course due to considered, intelligent, and deliberate motivations.

If the action then doesn’t match their own moral compass they will assume varying levels of evil and ill intent.

When the reality is more than likely they are “just trying to work things out, and get through it” just like the rest of us. Only their problems tend to be harder, and have more implications.

When trying to process actions taken by CXOs that you can’t attribute to being in the best interest of the people in the organization it’s very easy to jump to the conclusion that their actions are due to them aligning more with the shareholders than the people of the organization.

An Example: Employee Equity Failures.

Employee equity in tech companies has become a majorly desirable option for both employees and employers alike. It allows employees to share in the success of their companies, and it allows employers to defer chunks of compensation to a point when the companies have become financially successful.

However, with financial markets re-adjusting, and the economic situation across the world taking a significant battering over the last couple of years, some of the programs have ended badly for the employees. With reports of employees losing out heavily on taxes, ending up with negative equity, and even ending up holding massive loans with no way to pay after being laid off.    

The Gold Derrière View

If you assume the leader of these companies do in fact have Golden behinds. You would assume the higher leadership knew exactly what they were doing during this process you can read it at best as a desire to keep real cash from their employees, and at worst a flagrant disregard for their financial well-being.

The Normal Butt View

I think however the ‘Golden Derrière View’ is very far away from reality. When making these decisions, to get it right, the leadership needed to:

  • Implement equity programs that worked fairly with a fast-growing number of employees, taking into account the specific tax rules and regulations of the employee’s country.
  • Predict correctly the economic outcome of the initial COVID waves.
  • Predict the borderline catastrophic global financial situation that basically cut Venture Capital funding for tech companies off overnight.
  • Do all of the above for the first time!

The last point is worth considering in more detail, A lot of the companies who have come across this problem have had astronomical growth in their valuations and the number of employees.

It’s generally perceived that keeping minimal changes in c-suite members is a good thing, so you end up in a situation where you have CXOs moving very quickly from being managers of 10s or 100s of people to top-level managers of multibillion-dollar companies, with thousands of employees across the world.  

The people also by nature of their roles need to be obsessively enthusiastic about the prospects of their company.

Personally, I do believe that these rushed programs are generally applied in order to get people in on a good valuation. In true start-up fashion, they wanted to “Get something good out quickly, then sort the details later”

Unfortunately, the market reacted before they could sort out the details. People got financially hurt, and the ‘Golden Derrière Theory’ creates a lot of ill will, and significant bad press!

Expected Competence.

The major question here is in a time when start-ups can explode and implode within months does having consistent senior leadership, something that has historically been perceived to be really important, become more of a hindrance than a help?

Being a great CEO, or CTO of a company of a few people valued a few million dollars, is a very different task than managing a multi-billion company with thousands of employees across the globe.

Should we expect competence from those people, or should we be more flexible and more understanding of these people when they make mistakes?

Why can’t we have both?

I think the answer comes from looking at the topic from both ends.

Firstly, I do think we need to stop idolizing these senior tech leads, they really are just, predominately, normal people just trying to make it through the day.

Recent history is littered with a lot of these fabled leads causing unmitigated disasters. As I write the details of the FTX catastrophe are starting to emerge, and we appear to be watching the end of Twitter play out in front of our own eyes.

If we paint these leaders more as normal humans, potentially flawed in all the ways a normal human can be, then when they tarnish their golden sheen it becomes more palatable, understandable even.

Additionally, I think if we keep their humanity constantly at the front of mind this should mitigate people like Musk and Bankman-Fried being able to create incredibly high, but disastrously fragile value through mostly ego alone.

We are yet to see how his take over of twitter will play out, but it looks like it might have been pertinent If the banks were to stop and ask questions like, “are you actually capable of running Twitter?”, “what human flaws do you have that increase our risk?”.

If they had asked these questions, maybe they wouldn’t be looking to sell their $13 billion Twitter-related debt for 60 cents on the dollar only a few weeks after the acquisition.

Top Level Responsibility

As well as adjusting our own perceptions we also have to ask those who are strapped to the front of these rocket ship companies, please check themselves.

Are you the right person to implement this thing that has a critical impact on your employees? Would it be better for you to hire an expert for that? Or delegate?

This might sound ridiculous, but the large consultancy companies manage these kinds of things for people over and over again, but their dinosaur-like reputation puts them at odds with the hyper-fast start-up mentality.

Maybe we do have things to learn from the old-school traditional business practices. I’m not suggesting we run back to the lethargic, bloated business activities of old. No one wants any more “digital transformation plans”. However, sometimes employing someone to run a slow, deep, well-considered due-diligence on your evangelical super egos CEOs recent breakneck change in directions is the right thing to do.

Be wary of the Golden Butts, their poop frequently stinks just as bad as anyone else.