Stolen and shamelessly hacked with love and admiration from a screen shared with me by Farhan Thawar
Introduction
This started as a very short list of questions and comments that Farhan shared with me. He told me that he used a version of these questions to help himself choose what to do next, and where to go next.
I built on those questions, and what follows is a brain dump of all of the questions that I had. As I go through the exercise, I’m distilling the questions down to the most essential, which is section that follows this one. As long as I haven’t finished that list, the Essential Questions section will end with an ellipsis(…).
I’ve also included some analysis on my work history and what I’ve learned in the last 4-5 years.
An implicit question that I have for myself is
What is the value of joining a company versus being starting my own, where I can be held accountable to my own standards?
OR more succinctly
Career - build or buy?
The Essential Questions
These are the questions that I will ask myself about every opportunity.
Will I grow? i.e. Will I be working with people that I align with - intellectually, emotionally, culturally?
Are they interesting? i.e. Are they working on a problem that I want to solve?
Can I help them? i.e. Do I understand how I can help them, and do I want to help them?
Do they treat people well? i.e. Do they treat people as positive templates(seebelow)?
Are they willing to go the distance? i.e. Is there commitment and grit in their formulation of values?
Are they skeptical? i.e. Are they willing to embrace (or have already embraced) some version of productive skepticism?
Obviously, these criteria are deeply personal. While they may seem generic, it’s worth noting that without the context that I offer below, they begin to sound tautological. And then we slip into the trap of becoming a one size fits all “Top 10 things…”. (As an aside, as a general rule, you should resist and reject all such formulations and articles, a priori)
Value Creation vs. Value Protection
”Do the major risks of the company have significant overlap with my skillset?”
- Delian Asparouhov, Khosla Ventures
(Notes that he was taking notes while speaking with Keith Rabois)
(see the original post for more)
I originally wrote this section when I was outlining the details of how I would respond to the role that a company was looking for, and coincidentally found myself answering some fundamental questions about who I am and what I’m looking for.
Is the role that I’m going into a value creation role or a value protection role?
Is the company ready to take a risk on me if it is a value creation position? In this case, the risk involves looking at new ways of building product, building teams, innovating, measuring and leveraging data and artificial intelligence as a strategic differentiator.
My methods are proven(tome, at any rate :) ), but they have a very different tenor than what most executives and leaders are used to.
If they are uncomfortable with this, and unprepared to deal with the discomfort, then there will be a disconnect.
If it is a value protection role, do my values and practices align with the organization?
Is the company comfortable with me, and my style - or more appropriately, am I able to adapt to their way of managing and leading?
PagerDuty
Type of role: [ValueProtection]
For example at PagerDuty I was by and large able to adapt to their way of managing in a role that was value-protecting. The issue was that I came in at too low a level (EngineeringManager) for there to be a reasonable career path for me. More accurately, they only offered me a more senior when I had left and re-applied.
Helpful
Type of role: [ValueCreation]
At Helpful, my role was too narrow(onlyMachine Intelligence) and I did not have the scope to grow a team to my expectations. There were some alignment issues, but nothing I felt was insurmountable. However, personal reasons and circumstances meant that I couldn’t do an early stage startup gig any longer.
ROSS Intelligence
Type of role: [ValueCreation]
At ROSS, I had the scope and the influence, and was aligned with some members of the executive and the board, but not with all, which led to friction, and ultimately to my departure from the company.
Wave Financial
Type of role: [ValueProtection | Value Creation]
At WaveI was in what was sold as a Value Creation role, but which turned out to be more of a Value Protection role. Specifically, I was brought in to create an Artificial Intelligence practice. However, there were a lot of structural issues that required changes, and the company was not prepared to make deep investments in building the infrastructure needed. There was also a cultural difference in styles, which given the scope and influence that I was able to wield was a losing proposition. Further, I had not established meaningful connections and influence at the executive level, though I did make great connections and empathy with folks in the rest of the company. Finally, I was not excited about the work and the team - I took the job as what I thought was a safe bet and this limited the level of my engagement.
The Rest of the Questions
Company Intelligence
What do I know about the company? And how much does it align with who I am?
[Fulfillment]
Will I be working with extremely smart people?
Will I be learning a ton?
Will I be having a big(enormous)impact?
What(c|w)ouldbe my first big win?
[Product]
Is the company working on something that I care about?
Are they working on something that I want to exist?
Are they working on something that I want to be a part of building?
Do I understand what the company is working on?
What are the drivers of the business? What are the challenges? Who are their competitors? Who are their supporters? How do they win? How do they lose?
Do I understand the“equation”that runs their business?
[Reputation]
What does the press have to say about the company?
What does the market have to say about the company?
What do the competitors in the same space have to say about the company?
What do people say about the company?
Good, bad, indifferent - do I understand the message and outcomes that they are communicating?
Does the message match the reality?
Do they have a lot of marketing around how inclusive and wonderful the company is, but folks on the ground(ex-and current employees) tell a very different story?
How focused is the company on Marketing?
[People]
How does the company treat people?
How does it treat its customers?
Note 1: similar templates apply to partners / participants in a multi-sided marketplace or platform play. In other words, how does the company treat the humans in their ecosystem. A good example would be how Uber and Lyft treat their drivers, and how Instacart treats its shoppers.
Note 2:What is the primary motivation for the template? Is it economic pressure, a consequence of the business model that they’ve chosen, or something else?
Negative templates
User-as-adversary
User-as-child
User-as-chattel
User-as-resource
Neutral templates
[per John David Chibuk - neutral states are transitory states are not stable]
[TODO: Expand this section into an article, an essay or a presentation]
User-as-opinion
User-as-reference
User-as-group(peer|reference|influential|motive)
Positive templates
User-as-ally
User-as-peer
User-as-partner
How does it treat its employees?
Are they hiring people who can execute?
Are they hiring people who they want to grow into new roles?
Are they focused on levelling up their team - more specifically, have they realized the return on investment that comes from growing people?
How does it treat its executives?
What are the strengths and weaknesses of the executive team members and team?
Do I appropriately augment the strengths?
Do I appropriately shore up the weaknesses?
What are the existential risks for the company? Have the executives been able to articulate and communicate them to me?
Are executives authentic? Look for the person who guides the ship - are they authentic? Are they greedy? Do they sincerely look to improve the company?
Is there chemistry? Can I gel with these folk?
Does the executive team get along? Are they aligned?
The Interview
Hiring an executive is a very time consuming task. They should be willing to sink 20 hours into the interview process.
[Process]
Are they giving me the chance to see what working with them would really be like?
Are they asking me questions about real problems that they’re having?
And are they looking for answers or going through the motions?
Are they asking junior questions(whichis generally fine) and looking for junior answers?
(A good example would be an interview I had where the interviewer asked me a fairly basic technical question; I asked about the scale of the problem, and it was substantial - 100s of people, 1,000,000s of customers. I told them the beginnings of the simple answer, but steered toward the larger scale problem, and the interview came to a standstill. This then indicated a deeper issue, which we discussed and then amicably decided to end the interview and process.)
Do they understand how to build the trust and rapport needed to have conversations at this depth?
Are they willing to invest the time?
[Strategy]
Have they asked me to put together something that outlines my strategy and way of thinking, and did they really review it?
Or are they just winging the process?
Are they willing to share information on the details of the business(boarddecks, direction, etc.)?
[Hiring]
Are they checking my ability to attract, retain and grow talent?
Are my colleagues people that are able to do the same?
What will I be working on?
”Work on something uncomfortably exciting” - Larry Page
”Seek out impressively smart and effective people working on something interesting” - Paul Buchheit
Am I working on something that is intellectually stimulating?
Am I working on something that is fulfilling?(i.e.I get up every day happy that I am working on it)
Is there an appreciation for the craft of building?
Are they focused on building and delivering at a timely and effective pace?
Will I be a better engineer, scientist or mathematician for having worked with this company, and with this team?
Will I be a better leader at for having worked with the team?
Is my role narrowly defined, or will I have scope and influence across a broad enough area of the company to truly have an impact?
Time and Priorities
Does the company and the team have a good attitude about time?
Do they understand the Pareto Priority Principle - 80% of your time should be spent on your top 3 priorities in any given week, and 20% of your time should be spent on the other things.
Nothing is more frustrating than a company where output is frustrated by meetings
Do they have a good meeting culture?
Do they give themselves and their team members“Bigmeaty chunks” of productivity and focus?
Do they have a collaborative atmosphere?
Have they mastered the use of physical space?(forexample, in Banks and other places, cubicles are rigidly set, or things are fixedly open concept. Companies that have mastered their spaces - like Spotify, some of the Google offices and Pivotal - recognize that constantly hacking and improving your physical space is as important as the product that you are building)
Are they as output driven as I am?
I get deeply frustrated when a team is not delivering, not pushing, not moving forward, and I tend to dial out of the culture at that point
Am I able to influence and push things forward
Am I able to push a big win within the first 4-6 weeks that I am at the company?
Team Dynamics
Do I have a team that I respect, enjoy and learn from?
If I don’t, will I be empowered to build and create that team?
How can I win, even if I(orthe company) loses? Difficulty? Discomfort?
Am I with the right team?
Am I working at Company HQ?
Am I working with people who constantly expect more from me?
Am I working with people who share some or most of my key values?
Appendix: Anti-patterns
Ways of looking at the world that are explicitly or subtly not in line with what I would expect from a company.
The Joel Test
This is a test that has been around for a long time(Theblog post has a date of 2000/08/09). It’s from Joel Spolsky (of joelonsoftware.com fame)
This is the test:
Do you use source control?
Can you make a build in one step?
Do you make daily builds?
Do you have a bug database?
Do you fix bugs before writing new code?
Do you have an up-to-date schedule?
Do you have a spec?
Do programmers have quiet working conditions?
Do you use the best tools money can buy?
Do you have testers?
Do new candidates write code during their interview?
Do you do hallway usability testing?
Alright, so aside from the fact that this gives you insight into the state of development in 2000 - and yes I do remember using CVS for source code management, including the horrible, horrible merge and diff functionality among other gripes, as well as what are now surprising and mind warping comments about building your installer at the command line - but more importantly, there are a few specific things in this note that are cringe-worthy.
First, it is opinionated. And it gives a clear indication of where the author’s mind is. Similar to my list above, it’s hard to refute or contradict any of the statements and questions made in the test, or in the article that accompanies it. However, the choices of questions are important. This formulation is didactic, specific, and does not incorporate a framework for evaluating whether or not it is suitable to the reader.
To wit, things that we have learned about both readers seeking to apply the principles in the article as well as groups trying to integrate the learnings are not given important context about how marginalized or minority people might make use of the information.