I am a fan of business autobiographies. I loved Howard Schultz’s Pour your heart into it (4/5), and Shoe Dog Phil Knight (4.5/5) the most of the 50+ books I have read so far. I would give his book 3.5/5.
Since Bill Gates himself recommended the book by Bob Iger, I thought I should read it.
The story itself is pretty compelling, with the first few chapters mostly about his youth and childhood. The story of how he joined ABC, followed by his vision for Disney when he was being considered for the CEO role are the best parts.
I do not want to give the entire book away, but I felt the book itself did not give me any more glimpse into Bob Iger than what I had read in the press before.
He does not address the #MeToo movement issues, the book is very well scripted and he chooses not to reveal anything about himself more than what he feels is necessary and skips all the parts about his relationship with the previous CEO.
The great parts that I loved were his discussion with Steve Jobs before the acquisition of Pixar, the discussion of how the changing media landscape is a catalyst for companies such as ABC, FOX, NBC and CBS.
You are in a meeting with a few others. There is a presentation or document which has been provided to all of you in the meeting. After 20 minutes of the presenter talking and in slide #11, you get a question that pops in your head, about something that was presented.
You ask the question – “Why is it …”?
The presenter responds “Yeah, that’s a good question. I think …”.
A few minutes later in slide #17, another person asks what you think is the exact same question, but phrased differently.
Everyone in the room exclaims “Wow, that’s an insightful question”.
You wonder if it is because you were asking the question early, or because you are never able to get your point across easily, or because others don’t view you as “insightful”.
If you ever wanted to have a bigger impact on most situations, where people consider your point of view as impactful and insightful, then read on.
Over the last 3-4 weeks, I have been reading over 50+ articles, books and research on what Insight is. Here is a summary.
The capacity to gain an accurate and deep understanding of a person or thing
First, the definition and origins. The word Insight (noun) comes from Scandinavian origins (insikt) meaning inner sight or wisdom.
John Kounios is the leading insight researcher in the world, and a professor of psychology at Drexel University. He has done extensive work on understanding how everyone can be insightful.
First, most people solve problems in 2 ways
Analytical reasoning or Insightfully
Analytical reasoning is logical and structured.
Insightful thinking is creative.
If think you can just meditate on a problem for long and come up with an insight you are probably right, but most of us dont have that luxury.
You can coax an insight by looking at the problem more creatively.
According to his research, there are 3 things that are important to put your mind in a frame to generate insights.
Positive Mood: Creativity flows from a state of feeling safe or secure. When you feel safe or secure, you can take risks. And creativity is intellectually risky. When you come up with new ideas, they can be wrong. When you try to implement new ideas, you can meet resistance.
Large Spaces: If you’re in a large space – a big office, with high ceilings, or outside — your visual attention expands to fill the space, and your conceptual attention expands.
Take a break: When you take a break from a problem that you’re stuck on and do something completely different, you forget the bad idea that you were fixated on. It allows other ideas, better ideas, to bubble up to the surface.
The problem is these are not solutions that are useful if you are in a meeting room with others (say nothing if you are in a Zoom call).
What can you do to be more insightful then?
There are 5 things I have found, each of which I will expand on next week. They are :
Ask the question “For this to be true, what needs to be false”?
Look for exceptions in the data
Only look for the anomalies in the data, argument or thesis
Reframe the question by assuming you are the “customer”
Ask yourself “If <someone else who you admire> were to look at this problem, how would they frame it?
This research paper was published by the New York University professors Deepak Hegde and Justin Tumlinson. In this paper they posit that there are 2 theories, both of which are based on information asymmetries.
When information frictions cause firms to undervalue workers lacking traditional credentials, workers’ quest to maximize their private returns drives the most able into successful entrepreneurship
Information Frictions and Entrepreneurship
The researchers have built a mathematical model to view data on a) who becomes an entrepreneur vs working at a firm, b) what their earnings over time are and c) why do entrepreneurs choose to start a company.
Empirical analysis of longitudinal samples from the U.S. and the U.K. reveal the following patterns:
(i) entrepreneurs have higher cognitive ability than employees with comparable education,
(ii) employees have better education than equally able entrepreneurs, and
(iii) entrepreneurs’ earnings are higher and exhibit greater variance than employees with similar education.
What this means it that employers value people’s degree, credentials, etc. Most entrepreneurs believe they are as good (or better) than their peers who might have graduated with a degree from a better institution.
For example, potential employers commonly accept educational attainment and work history as signals of unobservable ability. However, the signals are imperfect if a worker believes his ability exceeds what potential employers can infer from his observable characteristics, then he chooses entrepreneurship and becomes residual claimant of his productivity, rather than join a firm in which he would be paid according to his observable signals.
I had a chance to read Essentialism – the disciplined pursuit of less this week. It was a quick read, with many stories and examples, and I would give it a 3/5. The big takeaway for me is to make conscious choices, say no to a lot of things and make routines that help you say no to trivial things more often. Here is a PDF copy of the book (Thanks to heram)
The basic value proposition of Essentialism: only once you give yourself permission to stop trying to do it all, to stop saying yes to everyone, can you make your highest contribution towards the things that really matter.
The way of the Essentialist is the relentless pursuit of less but better. It doesn’t mean occasionally giving a nod to the principle. It means pursuing it in a disciplined way.
Essentialism is not about how to get more things done; it’s about how to get the right things done.
If you don’t prioritize your life, someone else will.
ESSENCE: WHAT IS THE CORE MIND-SET OF AN ESSENTIALIST?
1. Individual choice: We can choose how to spend our energy and time. Without choice, there is no point in talking about trade-offs.
2. The prevalence of noise: Almost everything is noise, and a very few things are exceptionally valuable. This is the justification for taking time to figure out what is most important. Because some things are so much more important, the effort in finding those things is worth it.
3. The reality of trade-offs: We can’t have it all or do it all. If we could, there would be no reason to evaluate or eliminate options. Once we accept the reality of trade-offs we stop asking, “How can I make it all work?” and start asking the more honest question “Which problem do I want to solve?”
Steps to Essentialism
STEP 1. EXPLORE: DISCERNING THE TRIVIAL MANY FROM THE VITAL FEW. Essentialists systematically explore and evaluate a broad set of options before committing to any.
STEP 2. ELIMINATE: CUTTING OUT THE TRIVIAL MANY. To eliminate nonessentials means saying no to someone. Often.
STEP 3. EXECUTE: REMOVING OBSTACLES AND MAKING EXECUTION EFFORTLESS: Essentialists invest the time they have saved into creating a system for removing obstacles and making execution as easy as possible.
There are three deeply entrenched assumptions we must conquer to live the way of the Essentialist: “I have to,” “It’s all important,” and “I can do both.”
There are 5 variables to consider for the compensation, which might make it complicated, so I will try to simplify for 2 of the variables in this post – size of company and job location. I have collected data from 11 sources – PayScale, Glassdoor, LinkedIn, Salary.COM, Comparably and VC databases such as Pitchbook – sources below.
The variables are:
Size of the company: Impact of the role to the organization is a key determinant. Startups pay less than larger companies, but give more in stock. Seed stage startups will pay less than later stage, but give you more equity (in terms of % ownership).
Industry segment and sector: CTO roles in technology pay a lot more than roles in non technology companies, but that is changing quickly.
Scope of the role: CTOs are expected to be technical leaders, but many organizations also expect them to play the role of VP of Engineering and CIO in certain cases.
Years of experience or CTO background: The rule of thumb is that more experience equals higher pay and equity. Similarly if you have experience building large scale systems at companies such as Amazon, Facebook, Google or Microsoft, you will get paid more than if you are not.
The numbers below assume you are hiring a CTO, as opposed to having a co-founder as a CTO.
The next question is how can I get on the more or show that I deserve more than the guideline range? That question is best answered situationally and if you want to setup time with me for some advice feel free to email me.
The data is above is very subjective and has many nuances. Obviously salaries are very personal and negotiations play a big part in the final salary you get.
There is a an old myth that 80% of the jobs are not advertised. Depending on who you talk to, you will get a variation of this number – from 40% to 80% of jobs are apparently filled without more than 2 people being interviewed. While that is not true in my experience for all jobs (it is closer to 20% or less), it is very high for senior roles. In this post I will give you a few actionable tips on how to make your name on the shortlist when founders, CIOs, CEOs and board members are looking to fill that crucial role of CTO for their organization.
The first thing to realize is that there are far fewer positions than there are # of qualified candidates and for roles in the C suite, the right fit is absolutely crucial. So, while you may be interviewed, it is also likely that in 70% of the cases an internal candidate is chosen. The reason I mention this is so you realize that in most cases, you should be looking internally within your organization to see if there is a need for a CTO position.
In this post my goal is to give you more “at bats” – or more chances of being interviewed for external positions.
The hiring executive for a CTO tends to be the CEO or founder in 34% of the cases (more for technology companies), the CIO (Chief Information Officer) in about 30% of the cases (especially larger companies) and CDO (Chief Digital Officer), CPO (Chief Product Officer) or board member in the remainder.
If you were to leverage this data, then the strategy to get shortlisted for CTO positions becomes both easier and harder.
Easier because you know who are likely the key people to hire CTOs.
Harder because those people are very difficult to network with.
There are 5 primary strategies you can use to make sure you are “Top of mind” for these positions.
Make a short list of potential CEOs and CIOs in the companies you would like to work for (market segment, size) and find a way to add value to their work. I would recommend curating articles and content for them which helps them get a summary of key trends weekly.
Build and maintain relationships with colleagues at your current company who are thinking of starting their own venture
Build relationships with recruiters – there are specialty CTO hiring firms such as CIO Partners, YScouts and CTO Recruiter.
Build a comprehensive social profile so you get inbound requests for CTO positions – GitHub, LinkedIn, Twitter, Blog and speaking engagements
Contribute and work with a open source project which gives you an opportunity to work with the founder who could use help from you as a CTO
Now that you know ways to network your way into a job, what are the ways to find out about CTO jobs that are open?
There are 7 sources that have some listing of CTO positions. In no particular order, I would keep tabs on them every other week. The links below will only list the CTO open positions.
The plan itself comprises of elements you have to do each week, month and year. I have outlined several steps you might have to complete in each of the 5 areas.
You can take as long as you wish (2-3 years or 12-15 years), but being consistent and disciplined helps.
Body of work
Most items on this list will be “must have”. Either you have to show where you did these, or the products and solutions you built have to have the level and sophistication of success.
Area of work
Understand and outline customer problems
Have you been able to talk to and solve specific customer problems and show that you can articulate the problems in good detail
Define use cases
Outline what use cases are defined by the customer problems
Architect the solution
Display the ability to architect the solution using components
Choose the right stack
Asses the technical details of the problem to pick the right stack to build the solution
Develop MVP / early version
Either build it yourself, use no code / low code tools, get it developed or outsource it
Iterate and scale the solution
Show that you can go beyond the initial MVP
Deliver multiple versions
Show that you can build multiple versions and ship products through the stages of the product
Body of work
Most of the items in communication need not be external (For e.g. you dont need to have a YouTube video or Twitter profile) but they help if you can get inbound inquires for CTO positions that are not published.
Area of work
Proof of documents that outline detailed requirements Tip: Most CTOs I know use a blog or SlideShare to showcase this
Showcase complex architecture tradeoffs that were made. Tip: If you can showcase a few on SlideShare it would be great
Maintain and drive content for an engineering blog with examples of your work, etc.
Showcase ability to connect with developers and other technical teams by speaking at conferences, etc.
Show your ability to communicate at scale Tip: Record a few YouTube videos (one or two a month will suffice)
Engage with thought leaders on platforms such as Twitter (don’t need to tweet daily, but some engagement is preferred)
Most of these items will be asked in interviews and also checked on during references.
Area of work
Ability to hire first set of developers, who are willing to work on problems without clear definition
Show that you can groom and develop talent over time. Tip: Most CTOs I know have 3-4 public recommendations on LinkedIn of people who have worked for them
Showcase the ability to hire early interns / young members who can be groomed over time
Display the experience to manage individual performances by either coaching or dismissal
Coach and Mentor
Show how you can help team members grow in their roles and careers
Help team members achieve potential by helping them see the bigger picture, convince them to achieve greatness
Most of the items in trust are in display during interview questions.
Area of work
Show how you can collaborate with other senior leaders to set goals that the team can align on
Proof that you can align to metrics, drive metric definition, and outcomes using scalable processes
Explain how you worked with other leaders to help achieve corporate goals
Examples of how you changed your mind, based on data or otherwise.
Display examples of architecture decisions that were made from your “gut” – how do you make decisions?
How you treat others especially those who are junior and not yet tenured
Most of these items will be based on opinions of other people’s view of you – analysts you interact with, customers you talked to, others you interviewed. The best way to showcase these is to have an opinion and outline it – in any way you are comfortable doing so.
Area of work
Show how you have streamlined development, testing, release and operational processes and are adopting new trends (Agile, Scrum, etc.)
Perspectives on open source tools, latest technology trends (Containers, Service Hub, Serverless for e.g. in 2020)
What tooling and infrastructure trends can you outline to help you develop faster and with fewer resources
If you look at the pipeline above, (these are rough numbers I got (via LinkedIn) by searching for Developers (Satista), Software Managers, Directors and CTO. While not accurate, they are directionally right.
There are some caveats to this data.
I agree that a) it is not a perfect pipeline – i.e. not every one who is a developer wants to become a CTO, b) most people dont go through a straight line in terms of career growth and c) 29 million developers in 2020, is much larger than 10 million in 2010 or 5 million in 2000, when most of the 1 Million CTO’s started their careers.
One of the things that I enjoyed about working at Amazon was a mechanism called “Working backwards”, or what Steven Covey called “Begin with an end in mind”. Applying that mechanism to one’s career is a very interesting use case and an effective one that I recommend.
If you want to work backwards from “becoming a CTO” to currently “am an engineer”, then we start with the definition of what all is needed to be in that role.
The working backwards mechanism has 3 components:
a) Define the requirements with metrics to measure,
b) put a plan that shows how to achieve those requirements over time and
c) measure and track towards the plan monthly, quarterly and annually.
The top 5 requirements & metrics that qualify a person for that role are:
A body of work that shows the ability to solve complex business and technical problems with technology solutions, as measured by the impact of those products in terms of revenue and customers.
A proven ability to communicate (written, spoken) technical challenges with customers, employees, and media in a simple, concise way as measured by the number of documents (articles, papers) and speaking engagements.
A history of being able to attract high quality talent and build and develop high performance teams as measured by the size of the teams and the current roles of the individuals they hired before.
A willingness to build trust with other executives (sales, marketing, etc.) and help align on objectives to generate outcomes for the company as measured by the business impact (revenue, profit) of the companies they were a part of.
An ability to “see around the corners” and spot technical trends that will impact customers as measured by the new products introduced to market by the individual and the market impact of those products.
There are other subjective criteria as well, but what I have observed is that when two candidates are close on these requirements and there is little to choose between them, other factors – personal relationship / chemistry with the CEO, industry specific knowledge or expertise and brand of the individual become more important.
Now that we have the 5 requirements and a high-level overview of how to measure them, the next step is to put a plan in place and then track to the plan each quarter and every year.
I will try to outline a version of a plan in the next few posts.
A frequent question I get that I want to help answer in the next few blog posts is “How do I become a CTO? or Chief Technology Officer.
I used to give a few simple answers before: a) Focus on building a great technology profile -e.g. GitHub profile, speaking engagements, etc., b) Network as much as you can with potential founders and c) Learn as much as you can about the business elements of your industry, especially customer trends.
I realized these were good enough for a 30 minute career counseling call, but not very valuable for people who want to plan their career for the long term.
Now that I have more time, I thought I would take a data driven approach to answering this question.
There are great articles on what a CTO does, so I am not going to answer that question.
Instead lets focus only on what it takes to become a CTO.
There are about 780K people with the title “CTO” on LinkedIn and roughly 159K with the title “Chief Technology Officer”.
Filtering them by size of company, indicates 11% are in large organizations (> 10K employees), and over 75% are in small (<100 employees). Many of the large organizations have multiple CTOs (e.g. Microsoft has 38 people in my network alone with a CTO title). Many of them are CTO of a specific business unit, or industry vertical function.
Segmenting by location, 38% of CTOs are in the USA, 27% in Europe and the rest in other locations.
So roughly 1 in 30 software developers could become a CTO.
In my LinkedIn network, I have 1st degree connections with 541 colleagues with the title of either CTO or Chief Technology Officer.
I spend a few hours learning to deploy a LinkedIn scraper. It took me a lot longer than I thought it would, but that’s another story.
I scraped my network for 7 parameters:
Name: E.g. Mukund Mohan
Title: E.g. Chief Technology Officer
Location: E.g. Greater Seattle Area
Company / Organization: BuildDirect
All organizations they worked at before, title and tenure in each organization. E.g. Director of Engineering, Microsoft, 5 years
Education: E.g. Bachelor of Engineering and years at school (If available)
Skills: e.g. product management, startups, etc.
I put this data into an CSV file just to view it in an easy way for me to visually review it.
Three patterns (or archetypes) emerge:
The career technologist (52% of my network)
This individual has over 16.5 years of average experience after graduating, working at 4.6 organizations with an average tenure of 6 years in each.
This indicates that the most frequent way to become a CTO is to have tenure as a developer and grow in organization(s) over time. There were CTOs with over 27 years of experience in my network, and the lowest in this segment had 14 years of experience as a technical leader.
This individual has about 10.2 years of experience after graduating, working at 3.1 organizations with an average tenure of 3 years in each.
This indicates the 2nd most likely way you can become a CTO is to start your own company (likely with a co founder). I tend to have more startup CTOs in my network than others do, so this may be due to my background and experience.
This individual has 8.7 years of experience after graduating, working at 2.3 organizations with an average tenure of 4.6 years.
This archetype is unique and hard to find because they were at the right place at the right time. They joined a fast growing company (Google, Facebook, etc.) at the early stage and grew with the organization quickly enough to then get a role elsewhere as a CTO.
The rest are a motley crew of technologists with long tenure, but I am not able to put them into a specific bucket. They have done several roles, including software development, product management, etc.
In the next few posts I will address questions such as