July 12, 2019

Help me write my book by annotating the outline

Experiments in cultivating annotations on this site

Hey, let’s try something new today. Two things I want to do:

Firstly - I’ve got annotations installed by default on my blog so everytime you highlight some text you get the ability to leave an annotation. Think of it like in-line comments just like Google Docs. But few people know how to use it or have an account - so the best way to get people comfortable with this is just to actively encourage it Directly cultivating community is a great thing to kickstart engagement - I did this a long time ago when I first installed disqus and it was fun! See that post here: Intentional Communities ! Please try it out and let me know how you feel! (Yes I’m aware hypothesis kinda sucks on mobile… sorry!)

Secondly - I’m in the middle of writing a book. And I want to use the excuse of cultivating community and getting people familiar with Hypothesis to help me out by annotating the book outline below.

I’d love to get your comments, feedback, ideas and suggestions for where the outline and chapters fall short, where you enjoyed what you read so far and where you want to see more. (Of course, if you don’t want to use Hypothesis then there’s the usual Disqus at the bottom of the post).

The Book - Working title: The Strategic Independent

This book all started when I wrote a blog post called The Consultant’s Grain My working title for a while was going to be just The Consultant’s Grain. Thoughts? I think I prefer The Strategic Independent but open to feedback… . That post triggered me thinking about writing a book about being an independent consultant. But over time the ideas and work around being independent started to form into a slightly broader thesis - The Strategic Independent - where this book should be helpful for any kind of independent, freelancer or contractor that wants to think holistically about the work they do and how they fit into client organizations.

So, the working title The Strategic Independent.

What this book isn’t: it’s important to note two concepts that I’m directly trying to shy away from. Firstly - this is not a beginners guide to consulting. There’s a fair amount of content out there about that and I think it’s a market that’s better served already. Plus - while some of the beginner ideas are useful I’m more interested in exploring the ideas I myself am wrestling with i.e. the mid-career consulting concepts and ideas (I’m almost 5 years into my indie consulting journey now).

Secondly - I’m trying hard not to write the “If you follow these ideas you too can be rich” book model. There’s a ton of that out there already and I hate it. I want to explore the messy reality of how it feels to be a consultant. Where can you trip yourself up? What is the emotional journey? How do you actually get things done inside organizations? How do you do weird and interesting work that keeps you engaged? These ideas are more important to me than just chasing the money (though hopefully if you do those ideas well the money will follow).

So, here’s a summary of the pieces I’ve written so far and the overall book outline. Please annotate all over it with ideas and suggestions!

Chapter 1 - Intro and overview

This will be… some kind of intro I suppose! Most of these ideas are explored in my post The Strategic Independent (4,700 words) including:

  • The foundational frame of “work in context”
  • The interplay between strategy work and execution that allows you to retain clients for 12-18+ months at a time
  • What “strategy and stewardship” is and how I think about it
  • How to learn to be more strategic in your work and how to deliberately learn from client engagements
  • Only letting clients “in the strategy door” as a way to find good work and avoid issues later on

Chapter 2 - From Networking to Networked

This chapter will cover the messy reality of finding clients and what it means to be “networked” not “do networking”. There are two posts I’ve written here already:

Small b blogging (1,800 words) - although this post wasn’t deliberately part of my strategy writing there’s a re-write of this post that explores networked writing (aka blogging) for indie consultants. The core of the idea is to write for community and connection, not mass appeal. It references the idea from Venkatesh of “release, rework, reference” For those not sleeping at the back of class you might notice this post itself is a great example of reworking and referencing my own work!

When I re-write this small-b-blogging concept in the context of indie consulting I should explore some concrete examples from other indie consultants to better demonstrate the idea in practice I think.

Strange Attraction (3,000 words) - this post explores how I think about “lead generation” for my consulting work and contains a bunch of examples. The core concept being that building networks of interesting peers and then keeping them up to date with your work and how you work can generate warm intros which is the holy grail of consulting.

I think there’s one more post in this series (unwritten today) exploring the idea of “trust totems” - i.e. reference objects that give potential clients confidence that you’re an expert and allow them to find purchase on what you do. Things like books, how to guides, conference talks etc all act as trust totems and many mid-career consultants will have these by default. But it’s important to understand that case studies kind of don’t count here! It’s more important to show rather than tell here.

Chapter 3 - Bridging the Gap

This chapter is all about going from warm lead to long-term retainer and all of the things that go into that. Broadly I think there are two concepts to flesh out here (neither of which I’ve written yet):

The idea of workshops as portals into organizations. Something I’ve mentioned informally to a lot of folks and always seems to be useful is that I try and start all my consulting engagements with a workshop. Not a structured learning workshop but a free-jazz exploration of the problem space. These workshops are like magic portals that get you inside the client’s organization very fast and also begin building bridges so that you can close a larger ongoing retainer much more easily for two reasons: you have more context for the problem and you already built trust with the client.

Some kind of post exploring sales, how to structure a proposal, how to write an SOW etc. I don’t consider myself an expert here so I’m not 100% sure what take I’m going to have here but I think it’s a common pain point so I want to try and approach this in a way that hasn’t quite been covered before. Perhaps by exploring the emotional and inner anguish that comes with money talk and invoicing?

Chapter 4 - Effective Strategy Work

I’m pretty obsessed with doing effective strategy work. Work beyond powerpoints and documents - work that actually transforms and changes organizations. This chapter will explore how to do good work for clients, while recognizing that it’s hard to actually bring about change for clients. This is probably where I’ve done the most writing to date:

High fidelity consulting (1,000 words) - “Ideas without details and details without ideas are both risky”. This concept is all about moving beyond documents to a higher fidelity of work to enable you to be more provocative and useful with your outputs. This post is a short sketch of a longer piece that would explore more real examples of how I’ve done this in my own work.

How to get things done (500 words) - there’s a few provocative ideas in this post that need exploring and expanding. Most notably the deck linked here that really gets into the heart of the idea that “Amateurs talk about strategy. Professionals talk about logistics”. Again, when I flesh this post out to be a longer piece I need to bring in more real examples from my own work.

Yes! and… - “How to think on your feet without bullshitting”. I’ve got an analogy in my head around why improv comedy is much like consulting. Thinking on your feet, making things up without resorting to outright bullshit, keeping the focus of a room and so on. This post is not yet written, so let me know what you want to see in this post!

Strategy is the organic flow of ideas and people (900 words) - here we start to expand our idea of what kind of work we’re hired for in the first place and recognize that it’s all about the people. The title of this post is taken from an excellent paper by Stripe Partners and there’s lots more thining to do here. I think I can fold my idea of “shadow org charts” and how to understand power flows inside client’s teams inside this piece to make something compelling.

The consultant’s grain (2,500 words) - the piece that started it all! This piece is grounded in the insight that “(their) culture eats (your) strategy for breakfast”. It’s crucial to recognize which recommendations and strategies will go with the organization’s grain and which will go against the grain. Very different approaches are needed for each situation. This post is getting old now and likely needs a re-write but I’m still mostly happy with it.

Ways of seeing (3,800 words) - this was the first piece I wrote as a deliberate longer form beginning of my book writing practice. It’s the sequel to the consultant’s grain piece above. This covers how you actually understand and recognize an organization’s culture and embraces the idea that perhaps the pinnacle of consulting work is to help your clients to see in new ways.

How (and why) to roll your own frameworks in consulting engagements (5,000 words) - you could easily imagine this as the third part of a mini-trilogy directly following on from the two posts above. Ff teaching clients ways of seeing is important, this post shows you how to actually do it and walks through some pitfalls I’ve fallen into in my own work trying to rely on off the shelf frameworks. This post is long because there’s 4 real case studies from my own consulting work that really help to illustrate the idea.

Did I miss anything from this section? I think the meat of the book is here.

Chapter 5 - The Inner Life of Independents

This chapter is essential to ensuring that the book stays grounded and doesn’t come off too “finished” - the infinite game of being an indie consultant is ongoing and messy. This chapter will really explore those ideas of what it means to be an indie and how it feels.

I, consultant (2,700 words) - this is the only full post I’ve written for this section that tries to explore the wreck of how it feels for me personally to use the word “consultant”. I think there’s some important ideas in here but this post didn’t come out quite how I wanted it to - I think it needs a rewrite. Maybe I’m too close to the problem to properly write this one :)

Maybe one way to do this is fold in my post the power of labels (1,000 words) that uses references from folks like Robin Sloan (media inventor).

Another post that I have in draft right now is all about managing your time (but really, managing your energy) as an indie. Working with a coach last year I came up with an energy matrix spreadsheet that I found super useful as a way to think through balancing work and life during a particularly busy period and I want to tell that story and explore idea of time tracking, calendaring and scheduling for indies. This post is in draft right now and called “the jigsaw of independence” but that might change…

Finally, the very reason I’m writing this book is as a way to create a narrative thread through an otherwise disconnected set of client projects. This is important for a few reasons: so you can create some notion of personal learning and development but also so that you can deliberately learn and grow and not feel like it’s a treadmill of one client project after the next. Maybe this post would be called “of ladders and treadmills” or something.

Anyway - would love your annotations, comments and tweets on this outline. What is resonating? What is missing? As you can see I’m probably 60% of the way through writing the book at least in terms of raw word count (there’s obviously an editing process to turn a set of blog posts into a book).


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This post was written by Tom Critchlow - blogger and independent consultant. Subscribe to join my occassional newsletter: