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Ask HN: Dev promoted to more strategic role in startup. What literature?
184 points by rodh on June 24, 2014 | hide | past | favorite | 81 comments
I am a developer and the startup I joined as employee #2 a year and a half ago has been growing steadily. There are now double digits employees and I've been given more responsibility and authority.

Aside from development, some of my responsibilities up to this point have already included project management, staff management and proposal writing. Now I am joining the senior management team and taking on more strategic responsibilities, including determining the direction of many of the company’s future plans and projects.

There are several paths I am looking at for preparing myself for my new responsibilities. I thought I’d start a discussion as out of the demographic on HN, I am sure I am not the only one in such a situation.

Self-teaching directions I’ve been looking at so far are: - Business Analyst processes. - Agile planning - Agile requirements modeling - Effective proposals - Business development

Although there is certainly no absence of literature in this area, I've found it hard to find good recommendations. Does anyone have any suggestions for specific books in those areas, or any other areas that would benefit a developer taking on a more strategic role?

Honestly I would get a mentor. Find someone either in your org or out of your org that has the skills and career you would like to work towards and start talking to them. If you hit it off you may have found someone who can help you through the bumpy parts of your career and help you plan your next steps. Some people charge for this as career coaching and that can also have some value but it's challenging to sort out the best ones. Every place I've gone I've looked for a mentor to bounce ideas off of and generally double check my thinking and how I'm approaching problems and my career. You can go to industry events and start reaching out or just look for people you admire and reach out and start a dialog.

I personally think the concept of apprenticeship is lacking in the technology industry and we loose out on what other older professions have with clearer career paths because of their established practices of guiding people though their careers. That said I've seen it abused too so there always needs to be balance in these things.

I personally coach about five people (for free) in my current company and they come from all areas of the org not just my group. I was very lucky in the early days to have several great mentors in my life who helped me and I feel it's my job to pay that back now in the latter years of my career.

Books are wonderful but nothing beats interacting with successful people.

> get a mentor

Seems easier said than done. I wouldn't want to share details of what I do with random people. Probably not with coworkers either unless it's strictly related to the job at hand, but at that point the advice they can give you is also more limited. Also, you need to find someone with more experience than you, so you don't have much to bring to the deal.

> Books are wonderful but nothing beats interacting with successful people.

That I can certainly agree with.

I can't agree more with Kator's comment. Find a mentor - maybe pay for a business coach if you want but you would probably be able to find an experienced serial entrepreneur in your industry after one or two conferences.

I would however start today not with a book but a clean sheet of paper. Take a long hard look at you, your decisions and imagine explaining it all to a judge in five years time. What bits will you be proud of, which embarrassed by and which will land you in jail.

If I was to give five points I wish I had done more of:

- Always be hiring

- Always be filling the pipeline

- Always cut more out than you think is possible. Do less better.

- never ever lie, and stand up and speak the truth as needed

- know where the money is going

Spot on, for sure a mentor is great but introspection is a powerful tool.

The first thing I ask when I start coaching someone is what are your goals with your career? In my career I can literally boil it down to four points:

1) Passion

2) Leadership

3) Compensation

4) Hybrid (Tech + Business)

At any time in my career I can score these 1-5 (5 being best) and the closer I get to 20 the better I feel. That said this is just the "what's your motivation" phase, next comes the "what's standing in your way" phase where you look deeply at your strengths and weaknesses and see how they block your ability to receive what you're looking for in your career. Then comes the "ok so now what" phase where you start setting goals to help shore up your weaknesses and magnify your strengths. Then it's "rinse and repeat" basically measure, adjust and execute.

In my experience a good mentor/coach/consultant prompts introspection in a much more powerful way than books are able.

I like that - might choose a different four but the idea is solid

Also totally behind the rating on a five point scale.

> might choose a different four but the idea is solid

The goal is to personalize these parts so they're your own. By all means I encourage people to pick their own but boil them down to succinct things you can describe in an elevator pitch.

They're very powerful when you talk to a manager or a potential employer about what makes you happy as an employee. It can be hard for a manager when you ramble on about what you want but I can blast these out along with a short example of each and use them as the basis of a productive dialog with the person I'm talking to.

In short, yes, pick your own, but know them cold and know how you measure them and how you can communicate to others when your not at a 5 in every area! :-)

I think mine are :

- Autonomy - Collegiate - Purpose - Family - Money

Thanks for making me think it through !

Listening to LSE podcast ("Risk savvy") and mentions defensive decision making - where an intuition is to take decision A but fear of lack of defensibility if it goes wrong leads to recommending decision B

This is an interesting corollary to my "never lie" - and if you have any cultural affect on the company push for "failure is good if we fail fast and learn from it"


> > get a mentor

> Seems easier said than done.

Point made, it's work, and successful people will tell you that the road ahead is full of work. Take the challenge, figure out how to find and develop a trusting relation with someone who will be able to help you progress in your career.

> Probably not with coworkers either..

Yes I would suggest outside the org or if the org is big enough someone who isn't directly up your reporting tree. At one job I picked an exec who had lot more experience then me but he was in finance so he wasn't worried about my motivations, I didn't want his job nor did he want mine.

It's a good recommendation.

Endeavor runs a mentorship program, I know some entrepreneurs which have been mentored, and they have been very happy with their mentors:


There are other, more local mentorship programs (I know some in my home country but I don't know where you're located).

This is very true and valuable advice. I've witnessed first hand the tremendous growth my boss (the CEO and co-founder) has undergone in the past year thanks to his mentor. I am actually in the progress of getting a mentor too, with the founders' help. I'm very grateful for that.

Agreed. This should be step #1.

In the last five years moved from development, to leading the development team to more of a product management role. Fully agree with that DanielBMarkham it's "the people part of things is where you'll screw up", so I'd focus on communication and team-building as much as processes.

I've found a few books really useful:

* The Checklist Manifesto: How to Get Things Right (https://www.goodreads.com/book/show/6667514-the-checklist-ma...)

* Drive: The Surprising Truth About What Motivates Us (https://www.goodreads.com/book/show/6452796-drive)

* Making Ideas Happen: Overcoming the Obstacles Between Vision and Reality (https://www.goodreads.com/book/show/7696135-making-ideas-hap...)

* Delivering Happiness: A Path to Profits, Passion, and Purpose (https://www.goodreads.com/book/show/6828896-delivering-happi...)

* Rework (https://www.goodreads.com/book/show/6732019-rework)

These days I get the most value from articles and videos. Here is a list of my recommended articles on Medium, which might be useful - https://medium.com/@nickboyce/has-recommended. Some great stuff in the list recommended by ravivyas too.

Edit: Something else I have been experimenting with is buying executive summaries of major books, in order to familiarise myself with as many perspectives as possible.

Can you elaborate on the purchasing of executive summaries? Sounds interesting; I also like to forage and often find that, for certain books, I really just want the technical footnotes.

Sure. There are plenty of summaries available on Amazon, for instance, this summary of Good to Great (http://www.amazon.co.uk/gp/product/B008VGWCHY/ref=oh_aui_d_d...).

There are also some really great mini books like Scrum: a Breathtakingly Brief and Agile Introduction (http://www.amazon.co.uk/gp/product/B007P5N8D4/ref=oh_aui_d_d...)

Also, I haven't tried these yet, but there are a number of subscription services available for summaries like http://www.summary.com/ and http://www.getabstract.com/en/

The other way of cheating is by watching talks by the authors, which give you the key concepts from the book in an hour. For example Simon Sinek presenting Why Leaders Eat Last (https://www.youtube.com/watch?v=ReRcHdeUG9Y)

Rework was Awesome! I would recommend The Lean Startup http://theleanstartup.com/ in addition to those above. Made to Stick was a good one too.http://heathbrothers.com/books/made-to-stick/

The Lean Startup was a real eye-opener for me, even though I thought I understood all the key concepts (I didn't). For some reason I always assume everyone on HN has already read it!

Made to Stick looks great. Added to my wishlist, thanks.

Disclaimer: my day job is helping companies continue to operate at scale the same as they did when there were only 5 of them. Turns out this is not a trivial thing to do.

Agile/XP practices are a good starting place in-between cowboy programming and micro-management hell -- as long as you don't take them as a recipe book. They're simply best practices that you can and should learn. Then prune/modify as necessary. There are really too many books to list separately. I'd advise joining a local Agile User's Group and noticing who has their shit in one sock. Then find out what they're doing. You can also bring in external coaches.

You need a couple of good books on the people part of things. I can guarantee you that the people part of things is where you'll screw up. "Drive" is really good. http://amzn.to/1qtZdEd So is PeopleWare http://amzn.to/1iBnasO

For strategic stuff, especially in a growing company, you're going to have to master large work queues without having them eat you alive. If you'll allow me to self-promote, my Backlogs series is geared exactly towards this problem. http://tiny-giant-books.com/backlogs.htm

One observation: as you grow, it's not enough that you pay extremely careful attention to whom you hire. You also need to create an on-boarding system where new hires can learn and adopt the culture -- things like pair programming, how the build works, good coding etiquette, and so on. Setting the table for strategy to work is actually more important than whatever the strategy is.

Second observation: I imagine you're going to be swimming in business book recommendations. Business books are like dieting books: everybody has a few favorites. (I imagine this is because the material inside matches how they already feel). Better to identify specific areas, like Agile Requirements Modeling, and find books targeting those areas. Then look for practical advice. Otherwise you'll just have a ton of books that you'll spend hundreds of hours reading and not really have much to show for it at the end of the process.

Links to the books Drive: http://www.amazon.com/gp/product/B004P1JDJO

and Peopleware: http://www.amazon.com/gp/product/0321934113/

for those who are worried about clicking url shortners

DanielBMarkham has been on this site for a long time and is pretty well known, so I would trust him not to put shady links.

I also heartily agree with him that lots of business books are best digested as summaries - look them up on wikipedia, for instance. The fundamental problem is that many have a simple idea, but you can't sell a 10 page book. So it gets fluffed up with lots of case studies and extra material until it's long enough to sell as a book.

It sounds like you've taken the most important step, which is appreciating that "what got you here won't get you there".

One of my favorite books when stepping into a new role is M. Watkins, "The First 90 Days", which is very helpful in formalizing an effective approach to succeeding quickly when in a new management role.

It is worth trying to get some education in people management. While much of it is common-sense, it's worthwhile covering the basics -- the applicable laws, managing conflicts, that sort of thing. I have yet to find a good, practical book on organizational engineering (if anyone has a suggestion, please post it), but this is an area that I feel someone in your role should seek to understand well, because it has a big impact on the success of a business.

One of the most important, fundamental skills for a senior level manager is understanding finance. I recommend B. Knight, "Financial Intelligence" as a primer.

My favorite book on business strategy is M. Porter "Competitive Strategy", however, this book and all other business strategy books should be taken with a large grain of salt. They often suffer from survivorship bias, being applicable only to certain industries and times, and in at least one famous case, allegedly faking the data used to draw their conclusions. I treat business strategy books as leisure reading that simply provides another perspective.

I would have recommended the same books. In addition to that please read Books by Peter F Drucker on Management, strategy and how to treat Humans.

In startups, human interaction is most important more so than a huge corporation because both employee and employer needs to understand the importance of each other. Make sure you treat them right and make sure they are excited,valued and well treated.

Get a mentor, you need to keep them engaged, request with specific questions, ask for suggestions. No one wants to receive a specific mail asking me to be a mentor. they would rather send a note/ give a suggestion which will help you.

All the very best for you and company, and keep us posted on how your journey is.

If you're looking for a book on strategy, you can't go wrong with Peter Drucker.



Can't forget Moshidora (What If the Manageress of a High School Baseball Team read Drucker's "Management"): http://en.wikipedia.org/wiki/Moshidora

Definitely this.

The Effective Executive (Drucker) has been by far the best book on management I've ever read. No fluff. http://www.amazon.com/The-Effective-Executive-Definitive-Har...

In a senior role, effective communication becomes more important. One of the best books I've read about how to communicate effectively is http://www.amazon.com/The-Pyramid-Principle-Writing-Thinking...

It introduces a specific method to write concise, effective business documents. Then it shows how you can use the method to critique your own thinking.

Yes, I can't recommend this book enough. Throughout my career, I've come into contact with a number of consultants from Harvard/MIT, Bain, McKinsey, etc. They all had a way of communicating ideas so clearly and effectively that I could understand exactly what they were saying, almost immediately. There was virtually no loss of information between what they spoke and what I heard. The ideas and thoughts all just flowed into my brain painlessly. I aspired to communicate as well as these people, but I just couldn't figure out the formula.

Finally, one late night, sitting across from my managing director (the leader of a prestigious boutique pharma-consulting firm), I asked him rather bluntly, "How did you learn to speak so well?" He gave me a rather blank stare, and thought for a little while. "Ah!" he exclaimed, jumping up from his desk and darting over to his bookcase. After a little rummaging, lo and behold, he pulled out an old copy of the Pyramid Principle. I leafed through the book and found a number of notes and highlights as he explained to me that what I held was the single most influential book he'd ever read. He told me to read it, not as a way to structure presentations or emails (although it helps there), but as a new lifestyle. Fold the ideas and principles into your very being, so as to become second nature, and you'll never have trouble communicating again.

It's a must-read book.

+1. What a great endorsement for the book. Your two paragraphs capture so much and in such a delightful way that it's hard not to want to buy the book.

On a related note, this book (http://www.treesmapsandtheorems.com/) is excellent.

The author approaches communication from the principle of Gestalt psychology and really helps one understand how our minds communicate.

I'd second this book. I've just finished it and am writing up a synopsis for my blog. It's been useful for improving my own writing and I intend to use the processes laid out to assess decisions made by others in future.


When it comes to Management, I have to second vellum's advice and go with Drucker:


Classic (Mad Men era) of Marketing is ruled by Ogilvy:


However, I cannot stress enough the role of analytics in modern business strategy/marketing and Kaushik's book is the best:


The number one thing I'd suggest it learning to communicate effectively. Since you have been promoted already I assume you have some skills in this area - that's good! But it can be worth deliberately focusing on improving both your written and oral communication skills.

The best book bar none that I've read about strategy is "Good Strategy, Bad Strategy" by Richard Rumelt: http://goodbadstrategy.com/

I highly recommend it. It's clear, intelligent, properly defines what strategy is (which most other books fail to do) and isn't, and how to go about designing and implementing it. It's very low on bullshit and very high on examples and insights from both history and business.

"His strategy was to risk his lead ships in order to break the coherence of his enemy’s fleet."

He defines strategy incorrectly. He means "tactic". I think the problem is that "strategy" sounds more important, but it irks me every time someone confuses the two. (The US military thinks the difference is merely one of the size of the operation, which is also wrong.)

Nelson's strategy at Trafalgar was to have a decisive battle versus a skirmish. He wanted to destroy the French navy (and was willing to risk everything to do it).

Actually, Rumelt does not attempt to define the difference between strategy and tactic. I guess from his point of view, that difference is irrelevant - the two are linked, I suppose. The book, however, is about good vs bad strategy, not about strategy vs tactics.

Your comment is thoroughly unfair on a whole book full of insight and useful, actionable advice that can be applied profitably to competitive situations in business. You criticise one example, saying it does not fit your definition of strategy vs tactics (a topic the book doesn't even cover), and appear to discard the entire book based on that. This is a very unfair way to treat a book and I encourage you to think about what you write, when posting negative criticism of this sort.

Your comment is akin to implying that 2001 is a crappy movie because it doesn't fully explore the effects of void on the exposed human body. Yes, that's true, but it's entirely irrelevant.

For what it's worth, at the core of the Good/Bad Strategy book is a useful definition of strategy as a combination of three things:

1) An insightful diagnosis of the situation

2) A set of guidelines/policies/plans to take advantage of the diagnosis

3) Coherent action to implement that plan

In merely laying out and explaining this definition, this book enables the reader to correctly make the difference between useless fluff and actual strategy. Rumelt then explores all three stages and, in particular, spends a lot of time (rightly) on presenting tools that can assist in generating the insightful diagnosis (aka "aha moment") that is a prerequisite to good strategy.

Irrespective of whether it is "strategy" or "tactics", Nelson's key insightful diagnosis, according to the book, was that his seamen were more experienced at firing cannons in choppy waters than the more numerous Spanish/French Armada. Based on a "fair fight" situation, the British would have lost. But Nelson leveraged his insight into a plan that enabled him to pit the British fleet's strengths (skill at shooting in choppy waters) against the Spanish/French armada's weakness (lack of same skill), instead of pitting the British's weakness (numbers) vs the French/Spanish's strength (again numbers). That insight won the battle dramatically and set up the British Navy's domination of the seas for centuries.

Conversely, saying that Nelson's "strategy" was to have a decisive battle vs a skirmish is, by Rumelt's definition, a great example of "bad strategy". There's no insight in that - just a wish, a hope. In short, "Let's win with a decisive battle" is wishful thinking, in the same way that "Our strategy is to grow our usage numbers by 6% every week" or "Our strategy is to double our turnover next year" are wishful thinking.

Strategy begins with an insight of how to change a losing situation into a winning one, and follows with plans and actions to take advantage of that insight. Whether you then call it strategy, tactics, or some term of your choosing, is fairly irrelevant. The point is, this book presents, with great detail and tools, a solid way of thinking about strategy that can actually be useful to someone who actually needs to "be more strategic" and, as the OP appears to be, is confused about what that even means.

Sorry for the rant - I just felt irritated by the brief and unfair put-down of my heartfelt recommendation of this book in what I perceived as an unfair way.

> Conversely, saying that Nelson's "strategy" was to have a decisive battle vs a skirmish is, by Rumelt's definition, a great example of "bad strategy".

Nelson's tactics were in pursuit of his strategy, and even they remain open to question. The fact Nelson is revered as Britain's greatest naval hero is a great example of "it's better to be lucky than good", and not a great example of excellent strategy (or tactics).

I haven't read the book. It may be great. But the introduction doesn't inspire me. Post-hoc analysis of success is subject to the same problem as basing one's life choices on what elite athletes say in interviews.

You cannot define something incorrectly. He can very well define "strategy" as something, you would label "tactic". That does not make it incorrect. It is great that a definition is done for an overloaded and ambiguous word like "strategy".

I have not found a good clear definition for "strategy" and "tactic". Could you give yours?

Let me give a concrete example:

In the WWII Pacific Campaign, the overall allied strategy was called "Island Hopping" and the intent was to establish a chain of bases to allow the supply of airfields within range of Japan, and bypass most of the islands the Japanese had conquered. Anything action beyond achieving that goal was superfluous.

In one campaign an Australian field commander on a disputed island fought a vigorous offensive against the Japanese garrison. His job was defending the airfield, but as a consequence of his excellent leadership and tactics, he managed to capture almost the entire garrison with little loss.

MacArthur was, reportedly, furious:

1) The Japanese garrison was starving and almost out of ammo and posed no real threat.

2) Now supplies would need to be diverted to deal with the Japanese prisoners.

3) Ammunition and other supplies had been wasted and lives put at risk to achieve non-objectives.

Great tactics, but counter to the strategy, and thus unproductive.

A more recent example:

The US invasion of Iraq was a superbly executed piece of tactical planning and execution in pursuit of an idiotic (stated) strategy (conquer Iraq, the people will happily become democratic, and the Middle East will be inspired by their wonderful example). It's possible the real strategy was to generate business for large defense contractors, in which case job well done. Bravo.

In chess, strategy is long term, tactic short term. A tactic has a very concrete goal, and in a few moves you will be able to say "it worked" or "it didn't work". A strategy has a more abstract goal, and sometimes you won't be able to tell to what degree it worked.

In general, I'd say tactics are about working a defined problem, strategy is about defining the problem, or picking which problem to solve.

Aaaaaand.. Amazon thanks you. (As do I.) :-)

I don't think there's anyone writing better, more actionable advice on this particular transition than Michael Lopp at http://randsinrepose.com

I'd read everything on that site.

Seconded. If paper form is more your thing, I've found his compilation book "Managing Humans" (http://www.amazon.com/Managing-Humans-Humorous-Software-Engi...) to be a great place to start.

Here is what I did when I moved from development to product & Marketing

1. Follow people in the same field 2. Ready up on blogs and posts : I use Zite, Flipboard and medium 3. A book that helped me to a large extent is Good to great by Jim Collins (http://www.amazon.com/Good-Great-Companies-Leap-Others/dp/00...)

Also The Personal MBA by Josh Kaufman http://www.amazon.com/Personal-MBA-World-Class-Business-Educ...

4. Video from people in the same field. 5. This article https://medium.com/@noah_weiss/50-articles-and-books-that-wi...

Some great tools:

1. Trello - Project/product and pretty much manage any thing 2. Qlikview - Data Analysis : Excel on Steroids

It's a very short list, but I am learning on the job :)

Josh's book is great - he sums up a lot of thinking from other books. He also has an account here, IIRC. Jim Collins, on the other hand, seems to write kind of empty books without much actionable advice. In my opinion, at least.

There are lot's of good advice already but I'd like to add few more. You need to make a mind shift from dev/manager role to strategic senior manager. My recommendation is to read: Good to Great ( http://www.goodreads.com/book/show/76865.Good_to_Great ) On War ( https://www.goodreads.com/book/show/117031.On_War_Indexed_Ed... ( I'm not sure which English translation is the best )

and try to see how practical tips both give for decision making. Art of War is also good, but I'd prefer Clausewitz since it's much more straightforward.

And read this masterpiece http://www.ikea.com/ms/en_US/pdf/reports-downloads/the-testa...

I recommend the http://www.manager-tools.com site for lots of really great content on practical leadership & management. As for process ... yes, you can read all you want, but at the end of the day your success will be defined by your ability to sell a good idea (SDLC/ALM processes) to your team, not the pure quality of the processes themselves. If people don't want to or can get around process, they will.

I've never worked in a startup, but I run my teams as if they were small, fairly-independent-but-often-symbiotic entities. I started as a dev back in '99 and am one step below CIO in a 45,000 employee large corporation. If you'd ever like to chat about your problems or bounce ideas off someone, I'd be happy to.

Developing strategy, relies on understanding the patterns evident in the mechanics of doing business, (startups and mature corps alike).

To that end, I strongly recommend Michael Porter, who literally wrote the book on modern "Competitive Strategy". There is no other single source of strategic theory that is better than this. Anybody that has taken a b-school class on strategy worth their tuition will recall concepts like Porter's 5-forces.

Other answers seem to offer more recently offered books and some might dare to argue his frameworks are dated but really it's in a robust, tried-and-true-kind of way. Other books that try to cover defining strategy, value chain, industry analysis are often derivative of his work.

If you don't end up reading it at least get a list of his key concepts and google the shit out of them. They all seem like a "duh, i knew that" on paper, but you should have these theories in your back pocket whenever you need to formulate a battleplan.



Understand Lean paradigm as a way of delivering business value: http://www.amazon.co.uk/This-Lean-Resolving-Efficiency-Parad...

In terms of agile - I believe that scrum and related are too operational-related and not really strategic. You can skip that and delegate crunching it to others.

Master delegation - 1 minute manager, etc. - read at least one short book about it. Don't fall into micromanagement trap.

Couldn't help but notice that book has a terrible review from the author John Seddon - although he has always been a vocal critic of management thinking such as lean.

From a technical perspective, I have found 'The Mature Optimization Handbook' invaluable: https://www.facebook.com/notes/facebook-engineering/the-matu... (HN discussion here: https://news.ycombinator.com/item?id=6763683)

'Team Geek' is a great primer on technical leadership: http://shop.oreilly.com/product/0636920018025.do

Another recommended book is 'Shipping Greatness': http://shippinggreatness.com

Assuming you're already familiar with 'The Lean Startup', there has been a series of excellent 'sequels' on many more specific disciplines that you will likely find useful: http://theleanstartup.com/the-lean-series

A recent addition (that I am still digesting) on Agile processes beyond Scrum is 'Unblock!': http://www.continuousagile.com/unblock/ (Posted to HN a few days ago: https://news.ycombinator.com/item?id=7921200)

One aspect of strategy, crucially important, is actively, and continually deciding what not to do.

It is necessary to not do great projects and not pursue great ideas, because of scarcity of resources: the organization cannot undertake all of the good and great ideas it encounters.

There is nearly no organization that is not over-committed in its operations. This is constant, challenging, and avoidable problem.

Actively deciding not to do a project, or not follow a particular line of effort...instead of failing, by default to give enough resources or effort to an idea or project aids the organization to focus and excel in particular well-chosen areas. And avoid being mediocre in multiple areas and spread thin as an organization, by actively choosing to do less. What great project will you abandon, to focus on the other great projects you're already doing?

Mission statements fail to inform about what the organization will NOT do. A strategy does.

* Stuck: Why It’s So Hard to Do New Things in Old Organizations (recorded lecture, December 6, 2007)

By Rebecca M. Henderson, (now at Harvard Business School) formerly Eastman Kodak LFM Professor of Management, Sloan School of Management, Massachusetts Institute of Technology

Video lecture (skip the first 15 minutes) (total time one hour) http://video.mit.edu/watch/stuck-why-its-so-hard-to-do-new-t...

Take a look at the concept of servant leadership. I've worked at one business that used it, and it was phenomenal. The crux of it is that bosses are only as successful as the people doing the actual work, so the boss should focus on what is needed for them to be successful.


If you're under 50 people, you're still too small for many processes. Read every book you can lay your hands on about people-management (not project management, not product management, not strategy) and remember to over-communicate. The best lever you have at this point is to become a great manager of people--you'll motivate them to do good work and help turn some of them into great managers as the company grows.

Start with the "classics" like "mystical man month" (Brooks) for example, then get many of the books by Tom de Marco and possibly read Richard Gabriel's "Patterns of Software". The book about the "Chandler" project (forgot it's title) is also a particular good read. Those two in particular are interesting reads about why things fail.

Go on to reading the Toyota management style in itself, there's a couple of books about it, that's what many IT techiques are getting their ideas from.

It's mostly about finding your values so to speak and pinpoint what you really think makes up a good software development company - maybe your focus will be on organization, maybe on other things, so get an overview first.

These two articles are hopefully also an interesting nudge to think about many things:



O'Reilly has a very interesting book with analysis which practices actually work and why/how - sadly I also forget the title. There's for example a chapter about when and why pair programming works and when and why not.

Also, just watch carefully and learn to notice "good organization" - happens in surprising corners and niches and try to see WHY it's good.

"The book about the "Chandler" project (forgot it's title) is also a particular good read. Those two in particular are interesting reads about why things fail."

Dreaming in Code, by Scott Rosenberg. Highest recommendation. 10x coders hired by visionary engineer to scratch their own itch. What could go wrong?


Not "mystical" but "mythical" man month.

1st "Thinking in Systems" http://www.amazon.com/Thinking-Systems-Donella-H-Meadows/dp/...

2nd Article "Leverage Points" http://www.donellameadows.org/archives/leverage-points-place...

after these two you will have enough know-how on how to identify and manage systems (i.e.: your growing company)

then the only thing between you and success is reality, for how to influence the company reality you live in please read

3rd "Seeing Systems" http://www.amazon.com/Seeing-Systems-Unlocking-Mysteries-Org...

good luck and have fun (with the books, with your new responsibilities)

Foundations of Business Strategy started last week on Coursera:


Probably not too late to catch up.

What a fantastic suggestion. I've used Coursera on technical topics in the past, but it hadn't even occurred to me to look there in this instance. Thanks.

Wow, lots of good recommendations in this thread already... I skimmed them, but apologies in advance for any dupes:

I'd suggest some general "business strategy" works that will help you understand the context of how/why the very highest level business decisions are made, as well as some works that deal with tying together strategy and tactical execution (which includes technical initiatives).

1. Understanding Michael Porter - John Magretta. http://www.amazon.com/Understanding-Michael-Porter-Essential...

Porter's framework is VERY influential in the business world, and having at least a passing familiarity with his work is important at the higher levels. Going straight to the primary sources (Porter's books) can be a bit daunting as they are big, dry, and academic and not exactly what you'd call "page turners". This book is a fairly solid overview of the key elements of Porter's approach, and a good read before diving into the meat of Porter's works.

2. Competitive Strategy - Michael Porter. http://www.amazon.com/Competitive-Strategy-Techniques-Indust...

3. Competitive Advantage - Michael Porter. http://www.amazon.com/Competitive-Advantage-Creating-Sustain...

4. On Competition - Michael Porter. http://www.amazon.com/On-Competition-Updated-Expanded-Editio...

5. Good Strategy, Bad Strategy - Richard Rumelt. http://www.amazon.com/Good-Strategy-Bad-Difference-Matters/d...

6. Blue Ocean Strategy - W. Chan Kim, Renee Mauborgne. http://www.amazon.com/Blue-Ocean-Strategy-Uncontested-Compet... This book has its critics, but I think it's a worthwhile read. Some people argue against the whole idea of a "blu e ocean" market, but even if the authors aren't 100% right about everything, I think the lines of thinking this book fosters are valuable in a general sense.

7. The Discipline of Market Leaders. http://www.amazon.com/Discipline-Market-Leaders-Customers-Do... I think very highly of this book and the author's approach to strategy. It's not radically different from the Porterian approach in some ways, but I'd say it's narrower in focus and simpler. The big takeway is the idea (which should be obvious, but often isn't) that "you can't be everything to everyone". The authors push a model of choosing a market discipline to appeal to a certain type of customer, and making that discipline the core of your business.

8. The Machine That Changed The World. http://www.amazon.com/Machine-That-Changed-World-Revolutioni... Have you ever wondered what this "lean" stuff is all about? Or why Toyota is so revered by business leaders? Here's a good place to find the answer to those questions.

9. Working Knowledge- Davenport and Prusak. http://www.amazon.com/Working-Knowledge-Thomas-H-Davenport/d... Perhaps the seminal book on Knowledge Management, or at least one of them. If you want to understand the importance of knowledge in an organization, this is a very valuable read.

10. Outside Innovation - Patricia Seybold. http://www.amazon.com/Outside-Innovation-Customers-Co-Design...

11. The Future of Competition. http://www.amazon.com/Future-Competition-Co-Creating-Unique-...

12. The Balanced Scorecard. http://www.amazon.com/Balanced-Scorecard-Translating-Strateg...

13. Strategy Maps. http://www.amazon.com/Strategy-Maps-Converting-Intangible-Ta...

14. The Strategy Focused Organization. http://www.amazon.com/Strategy-Focused-Organization-Scorecar...

15. If Only We Knew What We Know. http://www.amazon.com/Only-Knew-What-Know-Knowledge/dp/14516... Another seminal title in the Knowledge Management world.

16. Common Knowledge - Nancy Dixon. http://www.amazon.com/Common-Knowledge-Companies-Thrive-Shar... Another seminal title in the Knowledge Management world.

17. Winning The Knowledge Transfer Race. http://www.amazon.com/Winning-Knowledge-Transfer-Michael-Eng...

Getting a mentor will help, usually someone outside the company that you trust enough to question them honestly (too many people try to get mentored by people they think of as infallible and then fail to ask questions when their understanding is incomplete).

If you are looking for reading material, consider putting the books "Execution" and "Facing Reality" (by Larry Bossidy with Ram Charan) on your list. I found these to be a good concise description of some of the more 'meta' aspects of senior leadership.

Consider the book 'Becoming a Technical Leader' [1], by Jerry Weinberg. He and his students (e.g. Johanna Rothman, Esther Derby) have a whole host of excellent books and courses in the space you describe. They're also very approachable, if you want to discuss these matters.

[1] http://www.geraldmweinberg.com/Site/Technical_Leader.html

The Heart of Change - best book I read in the MBA

Six Thinking Hats - best way to think like an analyst (and to lead meetings that are effective)

Both of these are killer and quick and easy books.

If you are looking for an intellectual discussion around management (helpful for some people) I'd recommend checking out Henry Mintzberg.

He's been writing on Management for 4 decades and he's opened my eyes to what management is about. http://www.amazon.com/Managing-Henry-Mintzberg/dp/1605098744

The book Understanding Michael Porter was a good introduction to strategy for me. I used it in my EMBA program when I was struggling to grasp business strategy. That gave me a solid grounding in how to think about it and some of the basic concepts. From there I was able to branch out to other books on strategy. But that one was a good starting point for me and some classmates.

Mobile MBA by Jo Owen - less empty words, more practical advice. My absolutely favourite management book.


How to Measure Anything -- By Douglas Hubbard

The successful role models in my life have a keen ability to at least relatively measure large, nebulous things. For thinking in probabilities and ways to gauge intangibles like "effectiveness" I think this book is excellent.

I'd recommend, if you have not already read them, reading the relevant seeming articles off the front page of joelonsoftware.com and possibly Dharmesh Shah at onstartups.com and Paul Graham's essays. There's a lot of good stuff there.

"Strategic Management" Fred David, http://amzn.com/0132664232

Some people find it too academic but it covers pretty much all of the essentials of strategy and business policy practices.

If you are in the bay area then we should go grab coffee some time. I was in your position a year ago and I'm more than happy to share my experiences and struggles. Send me an email and we can connect.

I warmly recommend you to read Peopleware: http://www.amazon.com/gp/product/0321934113/

One of the best book I found in similar situation is High Output Management and Only Paranoid Will Survive by Andy Grove.

[Meta] I really wish I could see upvote counts for this post. Answers here are reviews and each vote for a review matters. If only 10 people have voted for anarchitect's list of sources, that means there is very little consensus here which could mean that there are no truly good books on this somewhat ephemeral topic.

I'd suggest reading Four Steps to Epiphany to learn about customer development.

Just learn how to think. The best way to learn to think is to solve many problems. Solve many problems many times. Don't just solve the ones you already know how to solve.

I am not sure you can learn how to think from a book, but the recommendations here can be good to "know what you don't know."

Maybe the best question you should be asking is not what to read, but what problems you can solve you have not solved before. Here is one constraint: if you can solve it yourself, and not through others, then it is not a very interesting problem.

Karate kid learned from a book in the beginning.

Wax on. Wax off.

Obviously a book won't do. You need a training montage.

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