One of the running themes in this newsletter is that indie consultants serve as shadows to the client principals they work with, especially leaders. To serve well in this role, it is important for indie consultants to learn to identify real leaders accurately, by a robust and useful intrinsic definition rather than by titles. Here is mine:
A leader is someone with a high level of individual agency within an organization, with responsibility for an independent connection to external reality.
For those who like Boydian jargon, a leader is simply someone who owns their OODA loop. Or more precisely, they own the risks of their agency and decisions.
I tend to only work with leaders by this definition. Not because I’m a snob, but because it is the easiest, most robust situation, and I’m lazy. Your job as an indie consultant is to get inside the OODA loop of the “client” as an ally, and help advance their goals. This is easiest when the client is a single person rather than an illegible ghost in the organizational machine.
Identifying Leaders
A leader is someone who can directly judge and use any thinking or work they sign off on. They are not intermediaries accepting counsel or advice on behalf of other individuals or groups, and sending it up or down a chain of command (or into the blackhole that often exists deep inside large organizations). They are not applying inflexible standards controlled by others that they lack the discretion to override.
When you work through non-leader intermediaries, there is high risk that you will end up doing the wrong thing, or doing the thing wrong.
For example, perhaps you do work for a low-agency middle manager who is sourcing a report that will be presented to the CEO. The CEO will actually sign off on the report, declaring it good or bad, but you never get to meet them while doing the work. In such a situation, the chances of things going wrong are very high. Your chances of getting stiffed on the payment go up. The likelihood that you’ll get thrown under the bus and blamed for failure goes up. The chances of reputational damage go up.
All these risks can be mitigated and managed, and it’s possible to craft good gigs out of such situations, but it is neither easy nor particularly fun. So it is best to work directly for leaders when you can.
A true leader will acquire and maintain control of as much financial agency they need to do what they think is their job, including the ability to pay for other people’s time and labor. If they can’t acquire this agency, they will typically leave.
This means for an indie, a leader is also someone who can in practice determine entirely on their own whether to pay you, even if they nominally need someone else to sign off. Being recognized as a leader within an organization means your funding requests within your domain are not typically challenged. So you, as an indie, only have to make one person happy.
Leaders include executives by default, and others (such as uniquely skilled individual contributors) by exception.
Trust, but verify, that the defaults hold. You might find leaders in unexpected places, who are a pleasure to work for, or you might find that someone who walks and talks like a leader, and has all the right titles, isn’t actually a leader in any meaningful way.
Finally, don’t go by size of organization a leader runs. Leaders may or may not have a large number of reports “rolling up” to them, but they tend leave as much of the direct management work to others as they can.
Having to directly manage a lot of people directly weakens leadership tendencies, and strong executives tend to limit that to a few direct reports, so they can focus on leading. They encourage high-autonomy organizations where people need little management.
This does not mean they neglect people working for them. It just means they have a laissez-faire approach based on high situation awareness, strategic intervention behaviors, and strong inspection and monitoring habits. Like good teachers, they seem to have eyes in the back of their head. They are able to get the behaviors they want out of the organizations they lead without micromanaging or spending all their time in meetings with reports.
But their focus is on leading, not managing.
Working with Leaders
Within the idea of an indie as a shadow, there are two aspects to working with leaders, an opposed aspect and an integrated aspect. In areas where the leader is still growing, you occupy a somewhat opposed role, where you are growing as well. In areas where they have integrated personalities (where they have “eaten their shadow”) you have to occupy a much more aligned role, and you need to be integrated in complementary ways.
The net effect is something like being an evil twin. The “evil” part is the opposed growth aspect. The “twin” part is the integrated aspect.
Sparring work in particular, is about managing the tension of these two aspects of work. This means your ideal client is someone who is mature in the same ways you are, and growing in the same ways you are, just from the “other side.”
When this condition is not met, elements of coaching (teacher/learner) dynamics enter the sparring work. I personally tend to avoid this, again because it makes things harder. Being cast as a teacher or student in a consulting relationship means there are mis-aligned learning curves to navigate, in addition to the actual work of the gig itself. This introduces additional risks into the gig: they may like the work but be disappointed in your performance as a teacher or student. Or vice versa.
Again, the risks of learning curve elements can be mitigated and managed, and as with working for organizations instead of individuals, it’s possible to craft good gigs out of such situations. But as in that case, it is neither easy nor particularly fun. So it is best to work directly for evil twin leaders when you can.
Opposed Aspect Work
For the opposed aspect (where you’re growing together), the shadow aspect of everything positive associated with leaders is often a visible part of the perception of consultants they work with.
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If leaders are missionary, their indie consultants are mercenary
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If leaders are idealistic, their indie consultants are cynical
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If leaders are holy warriors, their indie consultants are pragmatic operators
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If leaders are charismatic stars, their indie consultants are grey blurs
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If leaders are taciturn doers, their indie consultants are voluble talkers
Generally only indies can truly play this opposed role. Consultants from larger firms don’t relate individually to leaders in the same way. Instead, the self-shadow relationship holds at an organizational, firm-to-firm level.
This default shadow role means the default perception of an indie consultant showing up in an organization is negative. This is why it is important for indies to be conscious of their halos. Consciously managed halos are how you counter-program default negative perceptions (created by the shadow position). You will never completely counter-program it, and that’s not a good thing to aim for anyway. You just want to be perceived in a way that allows you to be effective. You don’t need to be universally liked or admired within the organization. It’s okay to be in the shadow zone.
That said, in rare situations, the default perception of an indie consultant is positive. If the principal has a terrible reputation, then people supporting them can sometimes end up with positive perceptions, as foils who mitigate the negative traits. These are not good clients to work for generally.
Basically, you are the evil twin in the relationship by default, but if the principal is obviously seen as evil by everybody, you might be seen as good.
Integrated Aspect Work
If you have a passing familiarity with Jungian psychology, you’ve probably heard something along the lines of self-actualization being about “eating the shadow” or “integrating the self.”
This means, as (and if) they grow and become more self-actualized, leaders and their indie consultants start to resemble each other in key ways. Each begins to integrate their personality in complementary ways to the other.
This is why it is important to primarily work with clients you admire and respect. You are their shadow, but they are yours too. Either both of you grow, or neither of you does.
But while working in areas of shared growth is fun, working in areas of shared maturity is even more fun.
The biggest such area is being right. I got the idea from the Amazon leadership principles (a rare non-vacuous document of its kind) that includes this one: Good leaders are right a lot. You can actually make a triad of such statements:
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Good leaders are right a lot
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Good managers win a lot
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Good employees accomplish a lot
It is crucial to recognize that leadership often means being right but not winning. This is because leaders own risks they don’t entirely control, which means their game is more like poker than chess. Even with perfect play and no mistakes, they might lose.
By contrast, managers tend to control the risks they own, and play more deterministic games, so it is appropriate to judge them based on their win rates.
And down the hierarchy, non-leader individual contributor employees are typically judged on effort and output, whether or not it is winning output, or output that is right about a lot. That’s called doing your job, within the inner reality of the organization.
For an indie consultant working with a strong leader, striving to be right a lot, in ways that are complementary to ways in which the principal is right a lot, is the most important area of aligned, integrated work.
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Good leaders are right a lot. Good indie consultants are right a lot.
There are several other areas where leaders and their consultants can be aligned and integrated, but this is the most important one. They have aligned gut instincts, and are therefore right a lot in complementary ways. When they disagree, chances are, there is either incorrect or missing information in the picture, or an analytical error somewhere. So it is possible to have an important and interesting discussion that gets somewhere, instead of a futile argument that runs aground on fundamental misalignments.