Ask HN: Dev promoted to more strategic role in startup. What literature?

184 points by rodh ↗ HN
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?

83 comments

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

http://www.amazon.com/The-Essential-Drucker-Management-Essen...

https://en.wikipedia.org/wiki/Peter_Drucker

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.

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.

"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.

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.
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.
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).

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?

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.
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.

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.

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

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:

http://www.endeavor.org/

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.
> 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.

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 !

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

Enjoy

> > 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.

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)

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.
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.

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.

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.
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.

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.
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)

[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.
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.

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...

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.
Karate kid learned from a book in the beginning.

Wax on. Wax off.

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

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.

http://en.wikipedia.org/wiki/Porter_generic_strategies

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