Spooky Trustworthiness at a Distance

Last week, I kicked off my 4-part series to mark my tenth anniversary as an indie consultant with a look at the past and future of my workflows at the inbox level.

Workflows are the lowest layer of the consulting stack. The level at which Fingerspitzengehfühl (“finger-tips feeling”) operates. I like to think of workflows as the embodiment of your trust in yourself. Intra-personal trust if you like. In this second part, I want to take a similar ±10 years look at trust between you and others, or interpersonal trust. For indie consultants, this is primarily trust between you and clients. This is the second layer of the stack.

How Trust Actually Works

Indie consultants tend to be highly conceptual people. So we tend to model interpersonal trust in ways that are too abstract, like game theory (prisoner’s dilemma anyone?), crypto-like “proof of work,” or “trust signaling” through devices like a clear personal manifesto on a website, a list of values, or a curated bunch of gushing testimonials speaking to the virtues of a fictionalized version of yourself.

If you go down that road, the risk is not that you will fail to build trust, but that you will succeed at building a sort of ersatz, dehumanizing “artificial trust machine” that “works” in the sense of making money, but turns you into an increasingly commoditized and packaged offering. At best you will turn into a “trusted personal brand” within a clearly circumscribed market niche, rather than a trustworthy person living and working in a world of other humans.

What’s the difference?

A trusted personal brand represents a clearly specified and bounded promise, and a demonstrable record of delivering against it consistently. A trusted personal brand lowers risk on some close-ended front.
A trustworthy person it is worth trusting — somebody it is interesting to take risks with in an open-ended way. They increase your capacity for risk, and win or lose, you will be left feeling enriched rather than betrayed.

Not that there’s anything wrong with wanting to be a trusted personal brand. If that’s what you want, by all means go for it. If you play it right, and get a little bit lucky, you’ll make more money in a year than I have in ten, and move on from this level of the game entirely.

But the deeper reward of being an indie consultant is the chance to forge yourself into a trustworthy person in a fully human sense — but on a larger scale than most humans will ever enjoy. Everybody has a circle of coworkers, friends and family within which they are viewed as trustworthy or not. Indie consultants have a shot at a more public sort of trustworthiness in the open economy that goes beyond such local, personal circles.

This trustworthiness is condition that magically leads random distant strangers to reach out to you, and take on risky, uncertain challenges based in part on your support and promise of fellowship.

I like to think of it as projecting “spooky trustworthiness at a distance.” It’s my substitute for sales and marketing.

The “distance” of course, is distance on a social graph. Like between dwarves and elves in Middle Earth.

When it works, spooky trustworthiness at a distance opens up a world of optionality for you, where epic adventures can be had. Adventures where you won’t be the hero or heroine, but the shadow of fascinating heroes and heroines. What I’ve been calling shadows’ journeys in previous posts.

This requires an approach to trust that may feel awkward and unfamiliar at first.

Spooky trustworthiness at a distance rests on an individualized, anthropological understanding of how your actual gigs actually come about — or fail to. Trust, in other words, lies in the truths contained in a collection of stories that you start building with your very first client. It eventually turns into a sort of personal ethnography, or thick description, of the interpersonal dynamics triggered by your visible, available presence in the world of work. You are supply. The story of demand for you is a story about trust.

In my case, I can identify a sort of three-act arc in the ten-year story.

Act 1: Trust Ramp-Up

Here’s a quick tour of how I ramped up with the first few clients, and how trust developed in each case:

In February 2011, I got my first two clients off of Quora. Strangers who decided to trust me on the basis of my answers to questions on a public site. These were sparring gigs. The amounts were small, but the confidence boost was huge (thanks Gene and Mat!)
I got my third client in June 2011 via friends at a PR firm I had hired for a project at the job I had just left behind. It was a medium-sized strategic marketing writing gig. Though I got along fine with the client and was paid directly by them, the trust equation never really extended past my friends. It was a subcontract pretending to be a contract.
In early 2012, I landed my first big gig, my fourth client, for an analyst report project. It came via a reader of some of my enterprise software blogging (back in 2009-12, I was briefly blogging for the Enterprise 2.0 blog). It did not go well, due to misaligned expectations that didn’t become clear until the eleventh hour.
My fifth client — who I still work with, and is now my oldest client — cold-approached me in 2012 on the strength of my Gervais Principle series of blog posts. I’ve now worked with him across four senior executive roles at different companies, and I first developed 80% of my bag of tricks working with him.

The interesting thing is, at the time (2011-12) I could not easily tell what was working. But it was quickly clear what didn’t work well — my unhappy fourth gig taught me that initial trust must be converted to working trust by getting expectations aligned and crystal clear early on. But not through painful and structured conversations seeking “alignment” or clarifying “expectations.” That’s a waterfall approach to trust that basically never works because you just don’t know each other well, and end up making ritual noises. Instead, you do it by iteratively setting and delivering on small, bite-sized goals that get larger and larger.

Alignment and expectations are not things you define at each other, but things you learn about each other iteratively, possibly adapting and compromising along the way.

If all trust in a gig is actually “trust debt” linked to a big, uncertain deliverable outcome, you’re setting yourself up for trouble. Do not mistake a pleasant, collegial relationship for working trust.

Working trust is primarily a learned, shared, and genuinely felt confidence in the mutual acceptability of future work output before it is delivered.

This is a weird definition of trust — and one that I’m writing down for the first time, though I’ve operated by it for ten years. So what I learned in Act 1 is that there’s actually 3 elements to trust, with working trust being the most important:

Discovery trust: you trust the pathway that catalyzed the relationship, whether it is a chain of referrals, or a social object like a blog post. It is tempting to rely on credentials for this, but that doesn’t work. Credentials are filter criteria, not trust criteria.
Commitment trust: you establish enough 1:1 rapport to sign a contract that you feel good about, without too much scrutiny or a lingering sense that you might potentially get screwed over.
Working trust: you learn to trust each other according to expectations that have been aligned by iteratively learning about each other early on.

In Act 1, I experienced four kinds of discovery trust across five clients in two years (trust via mediated readership, trust via referral, trust via subcontracting, and trust via direct readership).

Commitment trust was always the same — the contract only got signed after I met in-person with the client and had a chance to establish rapport. That’s all it was — a test for a kind of shallow capacity for simply getting along during a low-stakes meeting.

Here is a contrarian opinion: it’s not worth getting too clever or careful with contracts. If you find yourself doing that, you’re attracting the wrong kinds of clients and losing at the game of becoming a trustworthy person. Most of the real risks in interesting gigs cannot be captured in contracts no matter how clever you get.

Early on, I just made up my own one-page contract and have used it for the majority of my gigs. When the client wants to use their own contract for whatever reason, I give it a quick once-over for typos and obvious mistakes, and just sign. If I find myself hesitating or wanting to argue minutiae, I back out. You cannot fix in the contract what is missing in the commitment trust level.

Working trust was the hardest to learn. The first year convinced me to avoid “working trust debt” (it’s like technical debt in software), and instead build working trust early and aggressively — in my case by specializing in what I call a sparring approach to consulting. This is of course not always possible. Many types of consulting are built around big deliverables and a lot of back-loaded risk. You have to figure out your own approach to mitigating that.

Act 2: Track Record

After those first five clients, I settled into a pattern. I had a non-empty track record, and always had 1-2 active clients going, even if billings were at a trickle. Though nobody has ever asked for references to past clients, the fact that they exist and are credibly listed on my website seems to make a big difference, both in clients’ ability to trust me, and in my own confidence in how I present myself. A track record is not really about the verifiable list of gigs you point to. It is about the confidence you project and inspire due to that list existing.

My slowly growing ability to do this kicked off, somewhere in early 2013, a second act in my adventures with trust.

The fact that I was mentioning a consulting practice in my writing and talks without sounding apologetic, or like I was faking it, and clearly not starving on the sidewalk, seemed to create the beginnings of an aura of trustworthiness.

Starting around 2013, almost all my clients came via my own blog: direct, inbound leads. The majority — perhaps 70% — tended to reference the Gervais Principle as their reason for reaching out to me. A few came via a couple of other lightning-rod type bits of writing. Interestingly, almost none of my leads came from my few attempts to write “content marketing” type lead-gen content.

Referrals, which accounted for 2 of my first 5 gigs (and probably more than 60% of my revenue over that period) became vanishingly rare, and stayed that way. I’d say they now track at around 1% of leads, and maybe 5% of closes. This was very surprising to me in the early years. I’d expected referrals to play a bigger role, and even made some half-hearted efforts to catalyze them. But apparently, the kind of trustworthiness I operate with is not very transitive.

Act 2 lasted perhaps 3 years. In terms of the three kinds of trust:

Discovery trust: was increasingly being established by my own visible online presence, mainly my writing, but speaking gigs played a small but crucial role. I was real! There was video evidence! I was not a dog on the internet!
Commitment trust: remained the same — the in-person rapport meeting remained key to establishing it. I’ve never had to change the approach I adopted in Year 1.
Working trust: increasingly I was only doing sparring work, which besides many other benefits, has a sort of pay-as-you-go trust learning structure. There is never any trust debt, and no nasty surprises lurk in distant deliverables. I’m only as trustworthy as my last sparring session.

Along the way in Act 2, in 2014, I did a year-long stint with Andreessen-Horowitz, a gig I think of as a charismatic megagig that significantly reshaped trust perceptions for me.

Charismatic megagigs are are important, and you should try and land a couple. They are what turn a strong but commodity track record into a differentiated one that marks you as the only person who can do certain things. I think I have 3 such on my record, though only one has a significant public aspect.

It proved to be an interesting milestone, since it added a sudden sharp spike of glamour and visibility, and added some high-visibility narrative color to how and why I was trusted, and by whom.

This actually had one significant downside, as I started getting a bunch of low-quality leads from second-rate entrepreneurs hoping for introductions into elite Silicon Valley circles in the guise of a consulting engagement. In many cases, it was openly crude overtures that assumed I was in the influence-peddling business (I’ve never accepted money or gifts to make introductions, and have never made an introduction that I didn’t actually think had potential).

But the upside of the gig (besides the Breaking Smart workshop I spun out of it) was that it triggered a shift to Act 3, where I was not just a track record from nowhere. I could be located with respect to economic scene landmarks — I was a guy with a track record in the tech scene. I was part of the software-eating-the-world bigger story, if only as an extra.

This is important. Nobody is every trusted or trustworthy in isolation. You are trusted against a larger backdrop or scene. Your fortunes rise and fall with that scene. You can have a reputation that is hedged across multiple scenes, but you can’t be a “trusted guy from nowhere in particular.” I’ve seen changes in how new connections react to me based on how the reputation of Silicon Valley and tech have changed over the years. If the reputation of the tech scene ever takes a terminal nosedive, I’ll probably go down with it.

This is neither good or bad. It’s just the way it is. Stick around long enough, and you’ll be part of both the hero and villain sides of every story you’re in.

Act 3: Part of the Scenery

After 2016 or so, things got a bit… diffuse. I could tell from the way leads led to gigs that it wasn’t really about track record anymore. Somehow, mere visible survival, general approachability, and avoiding the allure of packaged, branded self-presentation seemed to have done the trick of making me look “established.”

It feels kinda like being a human bus stop in a city. People who traveled certain routes in certain scenes were simply aware of my existence because I was a visible part of the landscape in those scenes. This can feel a bit strange — you end up being at once seen and not-seen.

One result of this is that gigs these days feel less like the result of mechanical effects or numbers games, and more like little vignettes in a big story where I have a small role. Vignettes that could be footnotes in a sufficiently voluminous business/economic history. The logic has gone from statistical to narrative.

In Act 3, the three aspects of trust start to work differently in some sort of mature mode:

Discovery trust: This works via simple known presence. You’ve been around long enough, and the world is small enough, that enough people already know who you are. You’re part of the scenery that’s their mental model of a scene. You don’t need to be “discovered” by the local economy any more unless you want to venture into new domains or geographies because you’re bored (which I suppose might happen to me some day).
Commitment trust: This still hasn’t changed. It’s still about meeting face-to-face (on video is okay, but not ideal) and establishing rapport, and signing a contract you don’t have to think too hard about.
Working trust: This has again broadened somewhat beyond sparring work. I now am more willing to take on more complex kinds of work, including calibrated amounts of “trust debt,” but only with people I’ve established baseline working trust around something simpler like sparring or a quick workshop.

So that’s where I am now, in the middle of the third act of a 3-act story of evolving ability to trust and be trusted by real people, while remaining an actual person rather than a brand. How does this act end? How many more acts remain? I don’t know but I can speculate.

The Future of Trust

Looking ahead, I can see some interesting new challenges already emerging. Some are a result of personal things — in the next 10 years I’ll go from 46 to 56 years old. When I started, most of my clients were my age or older. Increasingly, most of my clients are younger than me. In rare cases a full two decades younger.

I can see clear signs of a looming trust problem I haven’t had to deal with so far — simply being out of touch with the world my clients live in (feels weird to think some of my future clients may be in kindergarten right now).

This isn’t an academic problem. Already, I’ve found myself saying no to potential clients who are clearly looking for some sort of paid elder mentoring rather than the kind of consulting I am comfortable providing.

I’ll cross that bridge when it becomes impossible to avoid crossing it.

A slightly different trend is also shaping my anticipation of trust trends. The Great Weirding has left the business world in a very altered shape. The Culture War has reshaped the landscape of trust. Tribalism is an actual factor now, in how consulting works. Increasingly, to access some space of gigs, you first have to gain membership into some sort of tribe that controls access to that space. I don’t like that, and avoid that kind of space, but it may become harder and harder to do so.

Trust works differently now in subtle ways I’m still trying to make sense of. Spooky trustworthiness at a distance is getting spookier. I have a feeling only half of what I think I know about trust will remain true in 2030. The challenge will be figuring out which half to keep, and which half to toss.