I’ve mentioned my fellow indie consultant Tom Critchlow in this newsletter a few times before. In this guest newsletter, Tom describes his version of the practice, and explores his mental model of sparring practice as a sort of tenure for consultants. For those who have been following this series (Part 1: Introdution to Executive Sparring , Part 2: The Guru Factor), this post should serve as a helpful second example of the model. — Venkat

I’ve long aspired to be an indie consultant with a default mode of sparring work. From reading about it on Venkatesh’s website to experiencing it in brief flashes on consulting projects (often waking up on the mat, dizzy, wondering what hit me), sparring has been an aspirational end goal; something to quest towards.

I’ve been an indie consultant for ~6 years and have gradually managed to secure sparring consulting engagements. But rather than operate on stand-alone sparring engagements they’ve been embedded (often at the end of) a “more traditional” consulting engagement focused on deliverables and such.

However, I recently participated in the first sparring training dojo as part of the Yak Collective and came to the realization that pure consulting sparring is an odd thing to quest for. For starters, it’s not very lucrative, as Venkatesh outlines:

I estimate that a good sparring partner can support no more than half a dozen active clients in any given month without burning out. And it typically takes half a dozen meetings of 60-90 minutes across six months or so for the sessions to become truly high-value.

Most importantly, though you might be able to bill at a high rate, due to the individualized, automation-resistant, time-intensive nature of it, you’re not going to get mega-rich doing it. Sparring is an artisanal kind of consulting. You can make a decent living from it, but if you’re solving for big money from a 4-hour work week, you should look to a different kind of consulting business model.

Introduction to executive sparring

Contrast this to a more traditional consulting gig that might be 5 figures a month and involve several days of work a week.

So how can it be that sparring is such an aspirational model for indie consultants?

Thinking vs Doing

I believe the answer lies in the aspirational nature of sparring work — in short, it’s thinking for a living.

Maybe the best analogy is: reaching a point as an indie consultant where you can generate enough clients to be sparring as your sole consulting work is like reaching tenure. You’re set.

Let’s illustrate with a dumb graphic:

My theory goes:

When you start out consulting most of your billable hours are spent doing. You get hired for things like writing content, managing ad campaigns, photo shoots, executing campaigns, building websites.

As you get more senior, more experience and as you get access to more senior executives the work starts to include thinking. Your website design project is so good that you’re included in the brand refresh project, your marketing campaign was so good you are invited to restructure the marketing org, your project management was so good you’re invited to help shape OKRs for the company, etc.

Thinking for a living is more fun.

Thinking – the work where you’re looking at client’s organizations as complex systems with access to real decision makers is where the rewarding high value work comes in.

As you get a taste of thinking for a living it becomes tempting to want to spend all your time thinking.

The (wrong!) mental model here is of the indie consultant rising to partner status — a partner at McKinsey or Bain spends all day long thinking, not doing. So we chase the same as an indie consultant — aspiring to get paid handsome sums of money to think all day long.

Except. As an indie typically there’s no one to delegate to.  So you need to roll up your sleeves and blend doing and thinking. (I’ve written about this concept under the label “strategy and stewardship” in this post the strategic independent).

This is where I find myself 6 years into my indie consulting career. Blending executive sparring with executive level capacity building for clients. This might look like:

• A weekly sparring session with the CMO, and:

• 2-3 days a week working with the marketing org on various strategic initiatives

The first feels like getting paid to think, the second feels like getting paid to do.

My hunch however is that this is a local revenue maximum. I often work with clients where I get paid approximately a sparring day rate across all my work — both the thinking and the doing — and this lets me bill well and log a good number of hours per client.

While I’d love to abandon the doing work and focus on the thinking — on the sparring — I think it’s a mistake to prematurely optimize for thinking for a living. Especially while I am young enough to have some doing left in me.

But — 6 years into my indie consulting career — I’m laying the foundation for transitioning to sparring in the next few years. Sounds crazy? There are some good reasons.

The Benefits of Sparring: Owning your Time

So is sparring just an intellectually stimulating but less-well-paid version of consulting?

No — there are some clear benefits of chasing sparring as consulting.

Firstly, I’m a decade younger than Venkatesh and still able to pull stunts like billing 3 days a week to one client and 3 days a week to another client. Dipping into energy reserves and sprinting on work for sustained periods throughout the year. Much like physical fitness I can already feel my capacity for this declining.

Secondly, doing captures a large portion of your head space. When you’re managing a marketing org you can’t “take Thursday and Friday offline to write blog posts”. Operational work requires high availability and an “always-on” mentality. Especially if you’re in doing mode for multiple clients at once. It can be incredibly demanding on your time and any side project / writing / teaching / long-term research gets consistently interrupted, paused or put on hold.

Thirdly, doing is not resilient work. Doing work is much more reliant on the economy, access to local clients and more. Conversely, sparring work thrives in uncertainty as Nicolas Colin wrote in Launching My Executive Sparring Practice:

What do you do as an executive in a world perpetually ridden with uncertainty—because of the nature of computing and networks, because of macroeconomic ups and downs, because of the public constantly threatening to erupt in revolt, because of activists that are all too happy to fuel that perpetual fire to force you to comply with whatever they demand? 

What you do is find a good sparring partner who will help you navigate the uncertainty with clear strategic insights and frequent adjustments to your worldview, helping you to constantly refine your long-term thesis.

Shifting to remote consulting has been a big strain on my consulting practice — not so much on Venkatesh’s.

In a nutshell, sparring work is long-term stable, well-paid work relative to the amount of headspace and energy required.

Tenure-track not Partner-track

Which brings me to the (correct) mental model — not of an indie consultant reaching “partner” but of indie consultant reaching “tenure”. The ability to consistently generate sparring clients is a great way to earn steady money, thinking for a living and with a reinforced OODA loop that connects the value you create for clients to the value you generate personally from sparring. As Venkatesh outlined:

You and the client are each driving complementary OODA loops that intersect in the practice of sparring. You are inside each other’s OODA loops in a way that mutually reinforces both your learning processes. Yours is an appreciative learning process, theirs is an instrumental learning process.

The guru factor

The ability to earn good stable money while keeping a significant amount of time and headspace free is not to be under-estimated. It maps to the idea of a tenured professor in the way that they are free to explore self-directed initiatives and projects.

Let’s update that doing/thinking chart form above to include a third wave of “self-directed” work:

As the doing work gives way to sparring work, so too does sparring work give way to self directed work. I’ve plotted myself and Venkatesh (roughly) on the chart to illustrate roughly where we both land.

Venkatesh, obviously, has been busy: Ribbonfarm, ArtofGig, Breaking Smart, Refactor Camp, Tempo, being a Berggruen Fellow, book #2 etc and is now earning a not insignificant income from self-directed projects.

And this is the end goal — the aspirational nature of yearning for sparring work — it’s that it’s a path, an enablement to get to a place where you can have some model of “tenure” to explore your own self-directed projects without having to force those projects to live on their own immediately. You leverage skill in doing into sparring work and you leverage skill in sparring work to get to self-directed projects and revenue.

Personally, I’ve updated my mental model. I’m no longer chasing sparring as it’s own goal but rather chasing sparring as a means to create leverage to maximize time, energy, and self-directed interests.

The Compound Interest of Networked Writing

The final point I’ll make here is about how to chase sparring. For indie consultants who want to follow this path (and to be clear there are other paths to follow) the evolution and progression across this chart from doing -> thinking -> self-directed is defined by the volume and quality of the thinking in public.

As Venkatesh illustrated in the guru factor:

About 90% of your effectiveness as a sparring partner derives from the depth of your appreciative world view, developed and expressed through critical reading, writing, podcasts, and talks. Only about 10% depends on your in-session sparring skills.

So we might overlay on the graph above a model of thinking in public (writing or podcasting or public speaking or vlogging):

Thinking in public is both a product of spending time sparring with clients and a necessary driver of getting sparring clients. In short, chasing sparring as a consulting model (and ultimately chasing the self-directed “tenure” model) requires investing in thinking in public, creating a self-reinforcing feedback loop of clients hiring you for thinking and higher quality thinking in public.

Last week, I introduced the idea of executive sparring as a practice distinct from coaching. Continuing the series, this week I want to talk about the most crucial aspect of being a sparring partner — developing and embodying a deep, appreciative world view complementary to that of leaders of organizations, which makes you a useful foil to them in their work.

For better or worse, getting into the sparring partner business means coming to terms with a growing perception of a “guru factor” around what you do — even if you are younger and less experienced than your clients. This is a fraught business. It creates serious reputational jeopardy. There is a fine line between “guru” and “laughing stock” (or to use a more appropriate modern term, lolcow).

The jeopardy turns into double jeopardy if you happen to be Indian. And into triple jeopardy if your middle name happens to literally be Guru.

I’m not complaining. Just noting obvious facts.

So a good way to start figuring out the core of the appreciative worldview that can potentially form the core of your sparring practice is to own the guru-jeopardy and ask — what am I a guru of?

Take a stab at answering that question before we unpack the concept. As a hint: contemporary Western usages, such as unix guru, design guru, and of course, management guru, are actually closer to what I think is the correct understanding of gurudom than the literal translation of teacher.

The core of gurudom is not a teacher-student relationship, but a seeker-world relationship.

Nerding out over the innards of Unix, and developing an appreciative worldview through the lens of that nerding out, is closer to the true spirit of gurudom than being good at teaching computing skills. Gurudom is nerddom plus a certain guru factor.

Being a computer science teacher makes you a good person to learn (say) sorting algorithms or good Python style from. But being a Unix guru makes you fun to spar with about the future of computing, and an interesting companion for explorations of that future. People can go as deep as they like with you, knowing that you can keep up, even if you don’t agree with them.

Sparring and Appreciative Knowledge

Appreciative world views, which are at the heart of guru factors, emerge via accumulation of appreciative knowledge, a term due to urbanist John Friedman, who defines it in his book Planning in the Public Domain as follows:

The social validation of knowledge through mastery of the world puts the stress on manipulative knowledge. But knowledge can also serve another purpose, which is the construction of satisfying images of the world. Such knowledge, which is pursued primarily for the world view that it opens up, may be called appreciative knowledge. Contemplation and creation of symbolic forms continue to be pursued as ways of knowing about the world, but because they are not immediately useful, they are not validated socially, and are treated as merely private concerns or entertainment.

Friedman uses the term manipulative knowledge in opposition to appreciative, but he doesn’t mean manipulative in a Machiavellian sense. He simply means knowledge of how to actually do things to drive change in the world, accumulated by actually trying to do those things.

I prefer the term instrumental knowledge for this. I previously wrote about appreciative versus manipulative (or instrumental) knowledge here, if you want to go deeper, but in this post I want to apply the distinction to consulting work, especially sparring.

Here is the big idea to keep in mind:

About 90% of your effectiveness as a sparring partner derives from the depth of your appreciative world view, developed and expressed through critical reading, writing, podcasts, and talks. Only about 10% depends on your in-session sparring skills.

In this, sparring skill is similar to negotiation skill. In negotiations, 90% of success depends on the preparation you do before you sit down at the negotiation table. Only about 10% depends on your negotiation skill.

Gurus versus Pundits

These activities at the core of strengthening appreciative capacity — reading, writing, podcasts, and talks — are not primarily marketing activities, though they do serve a marketing function as a side-effect. They are integral to developing your capacity for sparring, but pursuing them for the sake of getting better at sparring doesn’t work.

I think of these activities as nerdy reflection, something very few people have much time for. It’s a time-wasting, bunny-trail-exploring nerding-out over the significance of things you’re seeing in your life.

So how do you develop appreciative capacity? The linked OODA-loops diagram above should convey the gist. You and the client are each driving complementary OODA loops that intersect in the practice of sparring. You are inside each other’s OODA loops in a way that mutually reinforces both your learning processes. Yours is an appreciative learning process, theirs is an instrumental learning process.

This means you cannot become a “guru” at something by deciding to study all the classics relevant to your interests. That turns you into an erudite scholar, an entirely different thing.

Why?

For much the same reason you cannot become a unix guru by reading scholarly papers and books about operating systems. You have to be at the keyboard, messing around with shell scripts, hacking away.

More generally, you cannot develop appreciative capacities in instrumental ways, anymore than you can develop instrumental capacities in appreciative way.

Here is another way to think about it: you cannot learn how to swim by reading a hydrodynamics textbook on dry land. But equally, you cannot figure out the molecular structure and chemical properties of water simply by swimming around in it.

This is easy to get when we’re talking about swimming versus chemistry, but gets a little tricky and very meta when we are talking about instrumental versus appreciative approaches to book-learning itself.

The thing is, instrumental means develop prowess at instrumental capabilities rather than appreciative capacities, even when the object of the learning activity is appreciative knowledge. You do have to develop your instrumental scholarship capacities to some degree, but they can’t be the primary focus.

That is not to say becoming an erudite scholar with a command over the canonical texts of a tradition is not a worthwhile thing. Go for it if that’s your thing. It just doesn’t develop sparring capacity or a guru factor.

If you are a completist about Sanskrit words for these things, the word for erudite scholarship has been imported into English as well: pundit (in India it is usually spelled Pandit, and is a common last name, as is Acharya, which is roughly synonymous). The differences are worth noting:

1. Pundits engage in scholarly debate with each other within an institutional tradition, and are governed by internal conventions and hierarchies. Gurus spar with all interesting comers, be they beggars or princes, and in any context.

2. Pundits can become institutional stewards of traditions, but rarely create new traditions. Gurus often create new traditions, but usually end up on the margins of even traditions they helped create.

3. Pundits often gain a great deal of worldly fame, wealth, and power, and this is viewed as just reward for their institution-building work. Gurus on the other hand, rarely do, and if they do, are viewed as having sullied their reputations.

4. Pundits represent and embody institutional epistemic authority, and take offense at challenges to that authority. Gurus have no such formal locus standi in relation to the traditions they may draw upon, and are rarely offended by challenges to their authority because they claim none to begin with.

5. Pundits often participate in visible and ceremonial and ritual forms of knowledge performance as the core of their work (traditionally, conducting temple services or sacrificial rites). Gurus typically do not. In consulting, this maps to doing talks or workshops around fully formed theories, versus informal “theorizing” discourses.

6. Pundits often present in highly ceremonial and authoritative ways, with a strong and consciously crafted halo, but often accompanied by ritual protestations of humility. Gurus stereotypically present in self-effacing ways, often being mistaken for beggars, but often present in poorly socialized ways, as irritable curmudgeons, or unpredictable trolls for example.

7. Pundits typically enjoy teaching, usually do it very well, and seek out opportunities to do more of it. Gurus typically don’t enjoy teaching, usually do it poorly, and seek excuses to avoid doing it.

The tension between pundits and gurus is so commonplace, it is practically a trope in Indian history. Similar archetype pairs exist in other traditions. In the Christian tradition, the distinction between regular and secular clergy is somewhat similar, as is the one between research and teaching faculties in universities.

A loosely similar modern one is the Straussian distinction between “great thinkers” and “scholars,” though that one is fraught with additional political-philosophical baggage, and conservative norms of reverence of ancient traditions that makes it not quite analogous.

Why does all this matter?

It matters because appreciative knowledge is not punditry.

Punditry is the result of an instrumental approach to appreciative knowledge. Gurudom by contrast, is the result of an appreciative approach to instrumental knowledge.

(for completeness of the 2×2, an appreciative approach to appreciative knowledge makes you a critic, and an instrumental approach to instrumental knowledge makes you a vocational learner).

In the world of consulting, gurus favor freeform sparring, backroom influence, and proximity to consequential decision-making. Pundits favor developing and delivering workshops and talks, building scaled institutions, and crafting powerful public images. Pundits develop personal brands (not always strong ones). Gurus develop reputations (not always flattering ones).

Both usually do at least a little of the other kind of activity out of necessity, but basically you have to choose, and choose fairly early, which path you want to go down. It’s like figuring out if you’re left-handed or right-handed. I’ve done my share of workshops, public speaking, and teaching. But none of that stuff comes naturally to me, I’m not very good at it, and I don’t enjoy it much. For better or worse, I’ve wandered down the guru path rather than the pundit path.

Peripheral Learning

What do I mean by “appreciative approach to instrumental knowledge”?

A good way to think of it is: Gurudom is weakly codified appreciative knowledge of the sort that develops on the peripheries of instrumental practice. The kind of knowledge that develops when you let attention wander towards the margins of instrumental activity, to metacognitive musings around it. You do have to play, but if playing well becomes the whole point, you’re better suited to playing excellence than coaching excellence.

Here we run into a problem though. Letting your attention wander to the margins of instrumental activity is dangerous. If you do it in mission-critical situations, you can become distracted and make costly errors.

This is one reason the best sports coaches often turn to coaching after mediocre career as players. A weakness for metacognitive distraction that diminishes performance on the field turns into a strength in coaching.

In live-fire situations, letting your mind wander to metacognitive concerns is often a sign of an even deeper weakness. It is a sort of displacement activity triggered by fear or anxiety, rather than actual philosophical curiosity about meta-concerns. This sort of person does not turn into a good coach, because they typically exit the live game with too much insecurity to be effective foils to better players.

There is, however, one activity which allows you to safely let a significant portion of your attention wander to the margins of instrumental activity.

This is of course sparring.

Linked Learning Loops

We are now in a position to appreciate the linked-loops diagram at the top of the page, representing the sparring process.

Sparring is a safe-fail activity immediately adjacent to live-fire activity. It benefits from a little bit of peripheral attention-wandering. It benefits from the kind of experimental trial-and-error attitude, accompanied by mindful critical attention, that is fueled by things you notice out of the corner of your eye.

So appreciative knowledge developed through the work of peripheral attention during sparring is what compounds gurudom, and makes you better able to spar.

This might sound like “the best way to get good at sparring is to do more sparring,” but that’s not quite it. While there is a component of mindful deliberate practice, it is only necessary, not sufficient, and it’s not unique to the sparring partner. The principal too, has to be mindful in that exact same way during sparring sessions, letting attention go to peripheral vision to a far greater extent than they would in the ring during an actual bout.

What makes the sparring partner role different is that you take the fruits of marginal attention around sparring and convert them into nerdy explorations which then turn into fodder for your own private pursuit of things that interest you (via writing, reading, and such), creating a growing store of appreciative knowledge. It is a virtuous cycle that powers growing guru-dom. This is the red loop in the diagram.

The yang to that yin is the loop experienced by the client you are sparring with. In the best case, the same sparring experience is cashed out differently. For the client, the fruits of marginal attention around sparring is converted into superior live-fire application, which leads to a growing store of instrumental knowledge. This is the blue loop in the diagram.

These two loops — both of which are metacognitive OODA loops with the sparring serving as an “Orientation” activity for both parties — are at the heart of sparring.

Where this beautiful symmetry breaks down is in the relative value of the two loops. The client’s loop passes through the real world. The sparring partner’s loop passes through the adjacent possible of the real world. The former, by virtue of having more skin in the game, is worth much more money. This is why the client typically pays the sparring partner rather than the other way around.

If the sparring sessions go well, the client will be forged into a better live-fire decision-maker and leader, while you will inevitably develop tendencies of a guru-like nature, whether or not you want them.

Recognizing Gurudom

The process I’ve described above should make it clear that you cannot actually choose to become a guru. Equally if you’re doing certain things well enough to be paid to continue doing them, you cannot avoid becoming a guru either.

This means gurudom is a tendency in your life that you recognize and come to terms with at some point, based on how people are choosing to relate to you. Including both how they are laughing or sneering at you, and how they are praising and appreciating you.

Again, think unix guru, design guru, or management guru. Not guy with long beard running a commune with sex slaves in the basement and Rolls Royces in the garage.

Some willingly lean into gurudom, some have it thrust at them (and some, like me, have it hang over their entire lives thanks to nominative determinism — I’ve been the butt of “guru” jokes since age 10, thanks to my middle name).

Gurudom is not primarily about a teacher-student relationship. A guru, or equivalent concept in other cultures, is rarely primarily a teacher, though teaching activity usually occurs on the margins of gurudom. The concept of a guru combines four elements that all play a role in sparring:

1. Reluctant teaching that is closer to preceptorship

2. Individual striving for esoteric appreciative knowledge

3. The capacity to keep up with others on their journeys

4. A degree of genuine (and costly) indifference to worldly rewards

Of the four, the teaching element in a conventional sense is the least important. It is the one that can be most easily delegated to others, and often is, at the first opportunity.

In the traditional Indian education model, known as the guru-shishya parampara (literally, “teacher-student tradition”), only the very earliest stages — the first few years — look like conventional teaching, focused on drills, repetition, and homework. And these are often handled by senior students of the guru, much like how graduate students do much of the actual teaching in American universities.

Teaching responsibilities can in fact seriously interfere with the actual responsibilities of gurudom, which are closer to “research” in the academic sense, but not quite the same.

As a result, gurudom finds its best expression via two core activities: sparring with peers in the same intellectual weight class, and through the ongoing development of an appreciative world-view. This latter activity can be understood as being a preceptor, which is closely adjacent to, but not the same as, being a teacher.

The natural fit with sparring and preceptorship is why faculty in American research universities are generally terrible teachers, prefer PhD students to undergraduates, and prefer to treat those PhD students as much as peers as possible, often handling actual advising responsibilities with great reluctance.

As with universities, which evolved in the West from the priesthood, with its vows of poverty and chastity, the guru tradition too has an uncomfortable relationship with worldly wealth. In India, gurus were traditionally expected to live in simplicity and relative poverty in humble ashrams in the forest, outside the civilizational core. They were expected to spar with kings, train princes, groom their own replacements, and produce pundits for the institutions that needed them.

The word is usually translated as hermitage in English, but modern day ashrams run by literal gurus are often relatively luxurious retreat destinations, suitable for entertaining kings and presidents, with great comfort lurking beneath a facade of theatrical simplicity.

Management gurus of course, usually skip the simplicity signaling and go straight for the 5-star leadership retreat experience in lieu of real ashrams.

The spirit of the ashram tradition though, is today best represented by the research laboratory, rather than a luxurious leadership retreat campus.

Emissary of the Adjacent Possible

Past the basic drilling stages, in the traditional Indian model, the student progresses to something that resembles more of a sparring process, focused on debates and disputations around classic texts.

These start out as rehearsals of traditional arguments around age-old questions, heavy with appeals to authority, and progress to increasingly free-form open debates on the “live” questions of the day. By the time the student gets to advanced stages, striving to best the master, in “the student becomes the master” mode, is the expected mode of engagement.

Here a fork in the road appears. The princes of course, go back to their kingdoms, assassinate their fathers, and ascend to their thrones. As adults, they may return to spar with their gurus.

As for the rest, some head towards punditry — stewards of the tradition within institutions embedded in secular life within the civilizational core. Others stay on the margins, and head towards gurudom in their own right — setting up the equivalent of experimental laboratories for their own nerdy reflections as best as they can.

This developmental path is not restricted to intellectual traditions. You can see a similar path in Indian music education, which begins, as in the West, with young students practicing scales and set compositions in ragas, and moves on to learning to render compositions in particular styles, peculiar to specific traditions. But at this point it diverges from the Western music tradition, and heads towards the free-form structured improvisation that is raga performance. These performances often involve a strong element of sparring with accompanying musicians (similar to call-and-response jamming as in jazz) known as jugalbandi.

Some version of this can be found all over the world of course. In Japanese martial arts for instance, we find the idea of kihon (drills), kata (set forms), and kumite (sparring). In the medieval European tradition of gallantry, young noble-born boys were sent off to serve as squires to peer knights, where they learned jousting, horsemanship, and other knightly skills.

Historically, this kind of education has always been something of a luxury, since it cannot be delivered at scale. Around the world, it was largely only available to princes being groomed for imperial leadership roles, or commoner students showing some promise as future pundits and gurus. There is a reason it is generally restricted to business executives today — paying someone in your intellectual weight class to spar 1:1 with you is not cheap.

For those providing this kind of education, the core activity — call it research, call it nerdy reflection, call it saddling senior students with the real teaching duties and sneaking off down bunny trails — became a way of life. Those who adopted this way of life, whether they were called gurus or something else, primarily engaged with the civilizational core by sparring with its leaders — and those being groomed for leadership — at the margins.

That is the essence of the guru factor — your stake in the margins of civilization, as an embodiment and emissary of the adjacent possible, bringing appreciative knowledge to life in the real world.

That’s a rather nebulous thing to try and be. But the core is simple enough — spar, nerd-out, write/speak about, spar some more. Pick people who you can keep up with, and who can keep up with you, as your sparring counter parties, regardless of what they can pay you. Recognize the adjacent activity of punditry and consciously choose one or the other.

The rest is just a matter of doing this steadily, for years, making money as best you can along the way.

Next time, we’ll talk about the actual content of accumulating appreciative knowledge, the content of your guru-factor, but to set it up, consider the opening question: what are you a guru of?

“Nothing!” is a perfectly fine answer.

Gurudom is something that creeps up on you after years of messing around, nerding out over things that interest you, and sparring with people. If you do have an answer, it is probably something that happened when you weren’t really looking.

For me, it happened to be organizational sociopathy and office politics.

The good news is, if you’re a guru of something, it isn’t a box that contains and confines you. That’s a price you pay for the rewards of punditry.

To be a guru of something is to look at the world through that thing rather than being put in a box defined by that thing. There are no restrictions on what you’re allowed to look at. The thing you’re a guru of is merely the appreciative perspective on the world people associate with you.

In other words, if people want to learn about X, they go looking for a pundit of X. If they want to see some aspect of the world through X, they go looking for a guru of X.

You can now ask useful follow up questions.

• Is your relationship to appreciative knowledge closer to punditry or gurudom?

• Is that what you actually want?

• If you somehow ended up on the wrong side of that divide relative to your natural inclinations, how do you cross over?

• How should you relate to those on the other side? As complements? Evil twins? Deadly rivals?

All useful questions, which we’ll get to in the next part.

For a while now, several of my fellow indie consultants have been asking me to share more details about executive sparring, a style of 1:1 consulting that I’ve been developing and practicing for almost a decade now. Before I get into it, I recommend watching this short video of Mike Tyson, at age 53, sparring with his trainer, to get a visceral sense of what I’m going to be talking about.

Yes, at their most intense, executive sparring sessions can feel like the intellectual equivalent of this. Not all sessions are this intense, or this combative, but the most valuable ones — both for me and for the client — are.

Like the sparring partner in this video, an executive sparring partner would not last very long in the ring in an actual competitive bout with a high-functioning executive client. Yet a good sparring partner can provide a great deal of value in a non-bout sparring session.

At this point, I’ve worked as a sparring partner with several dozen senior executive clients (some of them for years) in organizations ranging from startup scale to Fortune 100 corporations, and across half a dozen industries. Sparring work now constitutes almost the entirety of my consulting practice. It’s a fairly demanding and intensive kind of highly personalized 1:1 support work, and is neither cheap, nor very scalable. So unlike things like training workshops, or process/capability consulting, it’s not the kind of thing you can offer at scale. You’re not going to rack up hundreds or thousands of clients in a few years. You’re not going to be sparring with an auditorium-scale audience. Writing a book about your business ideas won’t make it any more efficient. You’re not going to be automating any of it.

I estimate that a good sparring partner can support no more than half a dozen active clients in any given month without burning out. And it typically takes half a dozen meetings of 60-90 minutes across six months or so for the sessions to become truly high-value.

Most importantly, though you might be able to bill at a high rate, due to the individualized, automation-resistant, time-intensive nature of it, you’re not going to get mega-rich doing it. Sparring is an artisanal kind of consulting. You can make a decent living from it, but if you’re solving for big money from a 4-hour work week, you should look to a different kind of consulting business model.

Teaching Sparring

Earlier this week, after conducting a first informal sparring workshop for a few friends, I decided I was finally ready to write about it.

While this series is primarily going to be for consultants who want to do this for money, it should also be of value to executives, since a significant part of being a leader is serving as sparring partner to peer executives and senior reports. In fact, most sparring happens among peers within organizations or industries. Executives hire people like me mostly when they cannot find suitable sparring partners within their own organizations or its immediate institutional neighborhood — which is as it should be.

Sparring is primarily valuable for senior executives who have already risen through the ranks of individual contribution and middle management (though that journey can happen surprisingly fast in startup environments), and is an alternative to the default style of working 1:1 with executives, which is generally called coaching. Unlike in sports, the two are hard to combine for reasons I’ll get to.

A question I’ve wondered about over the years is: can sparring skills be taught, assuming a broadly suitable temperament and an aptitude for it?

I’ve been at it for 9 years, and it probably took me 3 years to get it to consistently good enough that I felt I could do it with almost anybody. Can that learning curve be shortened?

Yes and no.

Some aspects of the skill-acquisition can be speeded up. Some things that took me years to figure out, I can probably teach in a day or two. But other elements of getting ready for the role — like reading widely and deeply about technology and business to develop an appreciative worldview of it (a sparring Weltanschauung if you will) took me decades (I’ve been reading business and technology books since I was a teenager), and I don’t think can be speeded up. I think will take anyone decades.

Fortunately, if you’re interested in developing sparring skills at all, you’ve probably already been doing the right kind of preparation anyway for other reasons, including plain curiosity. So you’re probably more prepared than you realize. It’s a question of recognizing the significance of what you’ve been doing, wax on, wax off style. But you’re probably not as prepared as you need to be.

In the pilot workshop a few days ago, I finally got a chance to try and explain and demonstrate the model to a small group of six willing guinea pigs via a small workshop. The participants were six indie consultants like myself, most of whom already had significant experience working with senior executives in a similar mode, but wanted to refine their practice and understanding of it, and make it more legible to themselves, to be able to continuously improve their practice.

The pilot workshop worked well enough that I decided this idea is actually in a teachable state, so I’m probably going to offer an improved version of it in the future, but before I do that, I decided I need to write up some of the core ideas.

So this is the first in a series of what I expect will be 4-5 newsletters covering the core ideas of sparring (the rest of the series is going to be paywalled though 😈).

In this introductory part, I want to do three things:

1. Define sparring

2. Distinguish it from other 1:1 relational practices like coaching

3. Situate it in the broader context of executive development

In the rest of this series, I will work through how to actually develop sparring partner skills, and a consulting business based on those skills.

Sparring as Live Theorizing

The goal of sparring is simple: to improve the quality of live theorizing executives do around their ongoing work.

The central insight driving the practice of sparring is that busy executives typically do not have time to do more than dip into fully formed theories of management or leadership, delivered through books, or executive education. Even the “case method” MBA students learn, which rests on live conversation/debate in groups, is too far removed from actual live situations to serve the purpose.

If you’ve ever read an HBR case study, you’ve probably had that uncanny sensation of looking at the business problem-solving equivalent of stock photography. A lot of fresh MBAs, who earned their degree perhaps too early, come across that way to me when they talk. They come across as smart, prepared, and with interesting things to say, but fundamentally lacking in serious exposure to live-fire, high-stakes executive decision making.

For strong executives, theorizing happens in a rough-and-ready form in the context of live action, working out how to act in, or respond to, specific situations unfolding now, involving specific people, constraints, and timelines.

Weak executives, by contrast, often come across as eager to avoid, sidestep, or ignore the hardest parts of the situations they are being paid the big bucks to handle. Much of their thinking happens on the sidelines, around situations that might unfold. Often their theorizing is too polished and refined — a dead giveaway that they’re far from the live-fire action.

Consider the analogous situation in boxing. A top boxer might study videos of an opponent for an upcoming title fight with their trainer, form a hypothesis about their weaknesses, and “workshop” bout strategies for that specific upcoming bout with a sparring partner. For example, Muhammad Ali famously did exactly that in preparing for his Rumble in the Jungle bout against George Foreman, abandoning the “float like a butterfly, sting like a bee” style he was famous for, and adopting a “rope-a-dope” style designed to wear out Foreman. Wikipedia describes how that came about:

According to photographer George Kalinsky, Ali had an unusual way of conducting his sparring sessions, where he had his sparring partner hit him, which he felt “was his way of being able to take punishment in the belly”. Kalinsky told him: “Do what you do in a training session: Act like a dope on the ropes.” Ali then replied: “So, you want me to be a rope-a-dope?”

According to Angelo Dundee, Kalinsky told Ali: “Why don’t you try something like that? Sort of a dope on the ropes, letting Foreman swing away but, like in the picture, hit nothing but air.” The publicist John Condon popularized the phrase “rope-a-dope”.

If this anecdote is accurate, than Ali’s intellectual sparring partner, as opposed to the one in the ring, was the photographer Kalinsky. It’s weird how often this is how it ends up working. You might talk for hours, but in the end, it’s one casual phrase or thought that ends up unlocking the critical idea. My very first client said as much to me — that after twenty hours of chatting, the value I delivered all came out of one phrase I happened to drop casually in thinking through a problem: “penny auction.” Two seconds in twenty hours.

That pattern has repeated for nine years. Hours and hours of conversation and emails, punctuated by scattered moments of high-leverage usable insight — a phrase here, a 2×2 there, a particular quote or metaphor that fits the situation. It used to frustrate me a lot initially. Was there no way to cut out all the hours and just formulaically arrive at just those moments of insight? So far I haven’t found one. You have to put in the time — and learn to enjoy it.

Insights like this cannot be found in textbooks, cranked out of fully-formed theories, or by “solving” cartoon case studies in a classroom setting (the equivalent of a punching bag or boxing dummy). They can only emerge through the process of preparing mindfully for specific live-fire challenges with a live sparring partner who can keep up with you.

Like good boxers, good executives instinctively seem to follow a similar, highly situational preparation regimen. They typically study developing situations that require action (many even like the “review the game tape” metaphor), form one or more working hypotheses about how to tackle them, and “workshop” them with trusted partners before actually trying them “in production” so to speak. At any given time, they are shepherding a dozen situations along towards resolution, and workshopping multiple ideas about what to do, often with multiple sparring partners.

This short passage from a classic paper by Karl Weick, What Theory is Not, Theorizing Is, gets at the essence:

Products of the theorizing process seldom emerge as full-blown theories, which means that most of what passes for theory in organizational studies consists of approximations. Although these approximations vary in their generality, few of them take the form of strong theory, and most of them can be read as texts created “in lieu of” strong theories. These substitutes for theory may result from lazy theorizing in which people try to graft theory onto stark sets of data. But they may also represent interim struggles in which people intentionally inch towards stronger theories. The products of laziness and intense struggles may look the same and consist of references, data, lists, diagrams, and hypotheses. To label these five as “not theory” makes sense if the problem is laziness and incompetence. But ruling out those same five may slow inquiry if the problem is theoretical development still in its early stages.

I quote this passage on my own consulting website and describe sparring in relation to it as follows:

The bulk of my practice comprises 1:1 work with senior executives as a conversational sparring partner, to stress test and improve the rigor and quality of their ongoing thinking about their evolving challenges.

Of course, executive work is not boxing. Meeting rooms are not boxing rings (though they can sometimes feel that way). Purposes in organizations are generally more aligned, non-zero-sum, and non-adversarial than in a boxing ring. The preparation is much more of an intellectual process.

But many of the challenges of preparation are very similar.

Who Can Spar?

The executive sparring partner role is a relatively new kind of external consulting role for a simple reason — the kind of immersive shared context required between client and sparring partner could not exist 30 years ago, due to the sheer difficulty of creating the shared knowledge environment in pre-digital environments. This means, historically, the role has almost always been played by trusted insiders and colleagues rather than paid outsiders.

Usually, executives spar with trusted peers who understand the industry well enough to keep up. Common sparring partners include:

1. An executive in another company in an adjacent non-competing business.

2. A board member, key investor, or a retired executive from the same organization.

3. An academic studying the industry or domain (rare).

4. A peer executive in the same company.

That last option is less common than you’d expect. Conflicts of interest often prevent direct peers from serving as sparring partners for each other, despite being the best suited for it in other ways. Peer executives are often competing with each other for power, influence, and control over specific situations, so mutual sparring support is limited to windows of opportunity when they are not striving at cross-purposes.

Despite these problems, peer-to-peer sparring still constitutes the vast bulk of sparring going on in the world, simply because of the numbers involved. It is just a highly unpredictable and unreliable source of sparring support. If an executive relies solely on peers for sparring support, they may find it unavailable just when they most need it.

Basically, it is surprisingly hard for senior executives to find the combination of three key required traits in one reliably available person:

1. Sufficient domain knowledge to allow shared thinking in insider-language

2. Absence of conflicts of interest and misalignments that get in the way of trust

3. Intellectual capacity to process at the typically demanding level

In the past, these three requirements often ended up forming a pick-2-of-3 triangle in a field comprising only insider candidates. But on the other hand, outsiders typically faced far too high a barrier of acquiring enough insider knowledge to play the role.

Until the internet happened.

The Internet as Sparring Arena

Thanks to the internet, it is possible for vast numbers of people who are technically “outsiders” to keep up with an industry or a specific company from the outside, participate in lively discourses around it, and be generally informed and prepared enough to play sparring partner roles.

In 2020, often all it takes to form a surprisingly deep and useful mental model of an organization is a few hours spent on Google, LinkedIn, Glassdoor, Wikipedia, and social media. Throw in a phone call or email or two, and you are probably 80% of the way there even before signing an NDA and being given a peek at internal information.

And you do not need limited, narrow and expensive subscriptions to business intelligence/dossier services to do so. Most of the valuable situation awareness information is free.

Add to that the trend towards increasing openness — many executives openly discussing their challenges on Twitter among other things — and the set of potential sparring partners available to any executive vastly expand. In fact, many seem to show up on Twitter to do exactly that — free sparring sessions with random members of the public!

If you’re an executive at a small, cash-starved startup and cannot afford to pay for a sparring partner, I highly recommend this approach. To the extent you can, just blog or tweet publicly about your work, and you’re very likely to find the sparring you need for free.

And if you’re looking to get into the business of being a sparring partner, there’s no better training ground than Twitter. You can literally try to provoke and engage thousands of executives. You’re very likely to get your first clients that way. I got my first couple of clients via Quora, and almost all the rest through some social media outlet or the other — Twitter, my own blog, contributions to industry blogs, and so on.

But information availability, while necessary, is not sufficient. Being a sparring partner calls for a particular temperament and personality (not learnable), and a particular mode of being attuned to others (learnable).

Sparring Partner as an Archetype

I’ve previously written about the idea of consultants as a well-defined archetype — shadows. This is particularly true of sparring partners. I also previously wrote about elements of consulting style, and offered this 2×2 of 4 types of 1:1 consulting roles, corresponding to 4 types of clients. While most clients are a mix of the 4 types (achiever, integrator, tester, explorer), most consultants, in my experience, can typically only serve in only one of these roles well.

Let’s get at the elements of the sparring partner archetype (both innate and learnable) via comparisons with the other 3.

1. Unlike a therapist or life coach, a sparring partner does not support inner work except occasionally as a side effect. Psychological insight into human nature is helpful, but not central to effective sparring.

2. Unlike philosophical counselors or mentors, the sparring partner does not occupy the position of a respected elder guiding an executive through inner or outer challenges they themselves have already been through. Your own banked growth experiences are helpful, but not central, to effective sparring.

3. Unlike an executive coach or teacher, the sparring partner does not support general-purpose behavioral development (forming good habits, losing bad ones, developing specific skills), in areas like productivity, emotional self-regulation, or “crucial conversations”. Behavioral insight is helpful, but not central.

What is central to effective sparring partnerships is actual understanding of the business domain and organizational environment itself. Having access to the enabling background knowledge is one half of the problem — largely solved by the internet. But actually being able to think on your feet with that knowledge is a different matter altogether, and the other half of the problem. One most people will fail at.

Often, this is a matter of the sparring partner having enough relevant career experience. People in classic “coaching” roles usually do not — they often have backgrounds in helping professions/fields like psychology, social work, or HR, but rarely in the fields where executives tend to emerge.

Most executives typically have career backgrounds (if not educational) in technology, finance, sales, or marketing, and are facing deep problems in those functional line-management domains. They usually need sparring partners who have at least a passing familiarity with the domains their work touches.

CEOs typically face problems that transcend even those functional domain boundaries and require knowledge going beyond, in that nebulous pile of backstopping activity that is “leadership”. They require sparring partners with domain/function experience and something more — a sort of philosophical fit of sparring styles.

This requirements makes “casting” for sparring roles much harder than for executive coaching roles, and it’s not a problem that can be solved by credentialing.

Executives typically know they’re not looking for traditional executive coaching, but can’t quite put a finger on what they are looking for. But they can recognize it when they see it.

Casting for Sparring

Much of the challenge of being cast in the role of a sparring partner is being visible in the right places when/where executives are looking for sparring support. That will be a topic for a future episode of this series, but let’s talk about how the casting process works.

Executives seeking sparring support often unconsciously look for sparring partners they can talk to in their own language, without having to constantly explain themselves, dumb themselves down, or having to provide quick tutorials on basic working concepts at every conversational turn.

They might provide a few pointers to learning resources, if they really want to work with you, but even that is rare. In general, they will expect you to learn enough to spar with them effectively in the very first hour. As a rule of thumb, if an executive has to spend more than half the time in the first hour of a sparring engagement explaining basic background ideas (especially basic technical concepts or basic business ideas like how to read a balance sheet), it’s not going to work out.

The ideal sparring partner is someone who already has a sense of the history of the industry and its technological foundations, has some functional depth in all the important domains the executive has to deal with, and has already been thinking about the latest fads doing the rounds.

The ideal sparring partner already has an opinionated take on important questions that are at least wrong (rather than not-even-wrong, which is the most common state), based on having kept up with the industry in question.

How do I know this? I know this because my clients have disproportionately been technology leaders, either leading technology/engineering functions, or having risen to CEO-level general roles from the technology leadership side. And this is not an accident. It is because I’m an engineer by training myself, and much of my writing and social media presence is suffused with technology references, metaphors, analogies, and historical anecdotes.

For a technology leader who reads one of my blog posts or a twitter thread, it is immediately obvious that it won’t take me painfully long to get sufficiently up to speed to serve as a useful sparring partner. I’m not going to be asking a machine learning company CEO what an eigenvalue is. I am not going to be terminally befuddled by a chemical industry CEO mentioning the ring structure of Benzene. Or by a CFO talking about gross margins and EBIDTA.

I’ll say more about this knowledge preparedness aspect later in this series, but make no mistake — sparring is a knowledge-intensive role. You have to know a lot, and showcase what you know, just to get in the game. And you have to be willing to learn a lot, very rapidly and efficiently, at short notice, to stay in the game.

If you have the temperament you’ll already know it. You probably read widely outside your field, and fairly deeply. You keep up with industry level trends in one or more large sectors at a play-by-play level. You keep up with science and technology news, at more than a casual level. You can parse at least half of any casual insider conversation you might hear about any industry in a coffee shop, and three quarters if you’re given a few minutes to google stuff (this is a game I used to play with myself a lot in coffee shops, back in the beforetimes when sitting around in coffee shops was a thing).

You don’t get there overnight of course. It takes years of being interested in business and technology and keeping up. But fortunately, it’s not a specialized kind of interest or attention. Whatever your reasons for your past interest and curiosity in business and technology, the fruits are going to be valuable in a sparring role.

Sparring in Executive Development

Let me wrap up this looong first part by placing sparring partners in the context of executive development more broadly. The short version is this: there is no element of sparring anywhere in the typical executive development offering suite, which is why I have an indie career at all.

The traditional executive coaching model does not work for sparring, because most coaches do not have the right background to serve as sparring partners. Other elements of the leadership development world do not address the need either. People in that world do acknowledge the need, but generally leave it alone as an area to be covered by mutual peer-to-peer support. Which also does not work great for reasons I’ve already pointed out.

The slightly longer version.

Back in 2008, when I was still confused enough about my own life priorities to imagine I might want to be on the executive-suite track myself, I was sent off by my employer, Xerox, to a “early high potential” leadership retreat at the Center for Creative Leadership, where I was subjected to a battery of psychological tests (Myers-Briggs, FIRO-B, CPI 260, Skillscope 360… see this pile of material I came home with).

It was a all a lot of fun, but felt like a bit of a LARP. Like I was pretending to be someone I was not — and doing it fairly well. Clearly, in some way I fit into this world, but not the way I was present in it during that program.

The capstone piece of the retreat was a couple of sessions with an executive coach. It was the first time I had done anything like it, and my expectations were low.

The exposure to executive coaching was particularly valuable because the coach assigned to me was pretty good at it, and it was a valuable session as a coaching session. I came away impressed by how well the coach had been able to get under my skin, and help me see some things about my behaviors. But I also came away with the impression that useful though it was, it somehow wasn’t even remotely helpful with the actual challenges I was facing at the time, in leading my project teams.

Perhaps that was just a matter of finding the right coach? Unfortunately, that’s not the case. I learned that my experience of coaching was in fact typical, from a book I read around that time: What Got You Here, Won’t Get You There, by Marshall Goldsmith, a pioneering executive coach, who in some ways invented the field (you can read my 2008 review here),

Goldsmith is known for pioneering the modern style of executive coaching, focused on behavioral rough edges. It begins with the assumption that anyone headed for the executive suite already has high competence and capability in their core leadership/managerial areas, but might require help addressing one or more seemingly innocuous blindspots and behavioral rough spots that end up being a huge liability.

Goldsmith’s model is the mainstay of 1:1 consulting models. As far as I can tell, all executive coaches practice some version of it, even if they’re not aware of it.

Unfortunately, the Goldsmith model has its limitations, and it became clear to me that coaching was not going to be the source of the kind of support I could actually use. Though I didn’t know it then, and didn’t call it that, what I needed — and never got — was sparring support. The few people around capable of serving in a sparring partner role with me were far too busy to spare more than the occasional hour, and usually available only when they wanted to talk to me, not when I wanted to talk to them.

Cut to three years later, in 2011, with my first couple of clients, it immediately became clear that what I was doing was in fact sparring — filling the gap I had myself perceived from the other side in 2008.

The idea that sparring is a distinct kind of 1:1 relational work has since been repeatedly validated by my experiences in the nine years since.

In fact, several of my wealthier clients have hired me for sparring while already working with both a coach and a therapist. These have been some of my best sparring relationships, because the client already recognizes that these are different roles, that call for different sorts of people to be cast in them. The sparring work does not accidentally slide into these adjacent kinds of work that I have neither the temperament, nor the taste for.

So that’s it for my introduction to sparring. In the coming weeks, I’ll cover several other topics: how to prepare for a sparring role, how to conduct yourself in a sparring session and in the follow through, assessing fit with a potential client, what kinds of potential clients to seek out or avoid, scoping engagements and setting expectations correctly, and how to find interesting sparring roles.

For now, I won’t be offering any in-person workshops outside of informal ones for people contributing to the Yak Collective, but if there’s enough interest, I might make an online course or something.

If you’re an executive looking for a sparring partner now, or might be looking in the future, drop me an email. One of my intentions in writing this series is to go beyond merely offering my own sparring services, to teaching the model and playing matchmaker to some extent, connecting executives with suitable sparring partners. We’ll see how that goes.

You’ve probably heard of the halo effect, where a generally positive gestalt is created around things or people with specific positive traits. For example, charismatic and articulate people who project confidence are viewed as more trustworthy and intelligent.

Take a second to think about this question: what color is your halo?

Or less figuratively, what do you think is the gestalt effect of how you are perceived in a client organization.

I got the idea for the question from a 1970s job-hunting classic called What Color is Your Parachute? According to author Richard Nelson Bolles, the title came about as a joke:

Years later, Bolles explained the book’s memorable title as his response at a business meeting in 1968 when someone told him that he and several co-workers were “bailing out” of a failing organization, prompting Bolles to joke, “What color is your parachute?”. “The question was just a joke,” he said, “I had no idea that it would take on all this additional meaning.”

It is interesting that a precipitate exit from a job in the industrial world is, by default, perceived as a catastrophic failure event that requires a parachute to survive. Even senior executives think in terms of “golden parachutes.”

One of the hardest mental shifts to make as an indie is letting go off this catastrophic failure mental model. You only need a parachute if you think you’re in a crashing airplane. If you don’t believe that exiting paycheck employment is like jumping out of an airplane, parachutes are moot.

As it happens, I’m in that situation right now. Next week, my 9-month fellowship at the Berggruen Institute will end. I’ll be back to full-time indie consulting starting May 15. Yet, though it’s a fraught time out there in the open economy, it doesn’t feel like I’m stepping out of a flying airplane without a parachute. To my pleasant surprise, I have enough confidence (and savings, and live cash flows, and active clients) that it feels like just stepping outdoors again, after a sabbatical indoors. The weather outside is bad, and things are probably going to get rough, but I’m not about to plummet to my death.

Certainly, there is risk involved in leaping out of paycheck employment, but in 2020, it is hardly leaping-out-of-a-plane level of risk. Or if it is, indies leap out not with parachutes, but with wings. Pandemic or no pandemic.

Halos over Parachutes

A parachute is for people who might fall to their deaths. Halos are for angels with wings who can sort of float in the air without an organization beneath their feet. Your future depends not on the color of your parachute but the color of your halo.

So a better question for the gig economy is this: what color is your halo?

Halos are very important in indie consulting, because they shape how you are perceived when you enter a client organization as an outsider, which is very different from entering it as an employee, as you’ll have learned if you’ve been at it for more than a few months.

In consulting work, it is important to be able to recognize a few important types of halos, including your own. Here is a picture of a handful:

Non-Indie Halos

Let’s take a quick inventory of the five non-indie halo types in the picture above:

1. Star Employee halo: This is the most basic kind of halo. The star employee harmonizes with the organizational background without blending in, is generally viewed positively, and sets the internal standard by which the halos of external parties are judged. The star employee is the hero of the organization. The halo color is gold, as in Golden Boy. I enjoyed a Golden Boy halo for a couple of years a decade ago. It was fun, and came with many privileges, but it is frankly an over-rated experience, since it tends to create limiting perceptions.

2. Big Consulting Firm halo: Employees of big consulting firms are the main external parties with recognized internal status (contractors and below-the-API staff are generally not “seen” at all). They tend to have somewhat robotic, one-size-fits-all, terminator-type halos. They project a mix of effective professionalism and intimidation (through borrowed authority of the CEO, and perception of involvement in things like layoffs). Their halo color is blue, as in blue chip. Big consulting firms are often seen as emissaries of the broader industry or market. There is a hint of benchmarking and judgment in the very presence of one of them in your workgroup.

3. Specialist Consultant halo: Specialist consultant types, such as lawyers or CPAs, tend to be put in well-defined boxes (hence the square halo). Their halos too are blue, and they too are seen as emissaries of the broader industry or market, but less threatening. They are sometimes indies, but more often part of partnership firms, receiving both paychecks and a share of profits. The often represent a particular sort of risk management, but crucially, they don’t own the risk, and don’t participate in it. They just help clients manage it.

4. Auditor/Inquisitor halo: Some sorts of outsiders have unambiguous threatening halos: auditors, compliance consultants for health regulations, pollution, sustainability, or diversity, trainers offering sexual harassment seminars, and so on. Their halo color is green, as in green-lighting (as in signing off on your compliance/conformity to some sort of external standard), but also as in green-washing (accepting complicity in a theater of compliance, particularly common in sustainability, hence the term).

5. Charismatic halo: Charismatic outsiders — famous authors, celebrity professors, ex-Presidents — tend to be brought in for largely ceremonial purposes such as keynotes during marquee meetings. They are not there to provoke, rock the boat, or actually make any difference. They are there to lend star power and charisma to the status quo. Their halo is therefore the same color as star employees — golden. Except their halo is actually star-shaped, since they are stars in the broader world outside. Often, they model, in exaggerated form, one or more desirable characteristics the organization wants to encourage in employees. They also afford senior leaders a chance to BIRG — bask in reflected glory.

That’s just a sampling of the halos you might see in a typical organization. There are many more, but that should give you an idea of how to think about perceptual gestalts of people against organizational backdrops.

Let’s talk about the sixth cartoon, the indie halo.

The Indie Halo

The indie halo…

Now here we run into a problem. Indies come in many varieties. In fact each indie is technically a distinct variety or they wouldn’t be called indies. There may be a certain amount of imitation in methods and postures, but we aren’t cookie-cutter types.

In one of my earliest newsletters, I argued that indies are shadows. In another, I argued that a fixed self-image is a dangerous thing for indies and that the right self-image is that of a trickster.

My opening question was a trick question. There is a correct answer: as an indie, your halo should not have a fixed color. The whole point of indie status is a certain amount of adaptability.

Personally, I have appeared in client organizations with a whole range of halos. I’ve had opportunities to do the charismatic star halo (even if only at D-list level) thing, the nerdy specialist halo thing, and the ersatz Big 3 thing. The only kind I haven’t done is the green audit/compliance thing.

But these fixed halos, even in imitation, are the exception. The default mode of indie consulting is to adapt to a very specific situation. Sometimes this means projecting confidence and charisma. Other times, it means projecting a narrow kind of competence. And sometimes it means projecting an annoying Jiminy Cricket type of conscience-on-the-shoulder personality.

You can never tell until you’re in the situation what the right way to play it is.

This is in part because indie consulting, no matter what you do, nearly always has a strongly improvisational component to it. You have to go yes, and… in response to the opening overtures of the client. And the nature of that improv response depends on the nature of the situation, and the posture the client is adopting within it. Your task is often to provide a response that is surprising without being disruptive.

If you’re new to this, one trick is to spot the local star employee halo, and then play foil to them in an interesting way. You don’t want to be seen as competing with the local hero, nor as the natural villain opposed to them. You want to be seen as someone whose presence makes the local hero’s journey more interesting. If you’re lucky, that local hero is in fact your client. If not, it’s a trickier improv challenge.

It takes time and practice across many situations and with many clients to develop a broad “halo range,” but once you’ve expanded beyond a couple of basic postures, you’ll find that it gets easier and easier. It’s a sort of method acting practice.

So take another stab at answering the question: what color is the halo?

But this time, think of the range you might develop around it, and how you might expand it.