How to coach a builder

So far I’ve mostly written about the individual work of building oneself into a builder. But if we want to fill our world with builders, we also need to know how to encourage and support this work of self-creation in others. 

The idea of coaching someone to build themselves may seem paradoxical: how can we coach someone else to do what, by definition, they can only do for themselves? 

This is not a mere matter of semantics: it poses real, ongoing challenges for any mentor, educator, parent, manager, or leader who wants to inspire or empower people’s agency. If you’ve ever tried to build an organizational culture around values like independence, autonomy, or first principles thinking, you know how easily such values can degenerate into empty slogans, leaving people without direction or accountability. Rather than take initiative to investigate and solve problems within the organization, they start to complain and externalize; rather than conceive ideas of their own and execute on them, they wait for someone to tell them what to do. Confronted with low morale and poor performance, many leaders then swing from “Zen master” to “drill sergeant” and start micromanaging. 

It’s tempting to conclude from such experiences that people either “have it or they don’t”; that the motivation to build has to come from within, so our best bet is to look for people who already have it. But this is plainly false. There’s ample research demonstrating how agency and internal motivation can be successfully nurtured in contexts as diverse as parenting, pedagogy, and leadership, and I’ve argued that this is the fundamental task of effective psychotherapies. 

What all these frameworks converge on, in one form or another, is that people are more likely to function like builders—i.e., to direct their own learning, set and pursue their own ambitious goals, generate innovative solutions to problems, and so on—when they’re coached toward a felt conviction that 1) they are capable of doing so, and 2) it is worth doing. 

What few of the existing frameworks recognize, but all implicitly rely on, is the further felt conviction that building is work; the often complex, sometimes painful, but always chosen work of understanding and shaping the world, and oneself alongside it. I would contend that this is the most fundamental insight of the three: after all, it’s only by doing the work that one comes to see what one is capable of doing in the world, and what is actually worth doing. 

Together, these three convictions constitute the “builder’s mindset.” 

Below are some key ways this mindset has shaped my approach to coaching builders, whether in the context of a particular endeavor (e.g., starting a company or playing a competitive sport) or of their life as a whole. To coach someone through building anything, one needs to know a lot about building in the relevant domain (be it entrepreneurship, sports, or mental health, for example). But one also needs a general perspective on the kinds of beings one is attempting to coach. The recommendations below are focused on sketching such a perspective, which you can then integrate with whatever particular knowledge or skills you want to impart. 

Note: these recommendations are not a substitute for specialized psychological training. If you think you or someone you’re coaching might benefit from more specialized psychological support, you can send them my “self-creator’s guide to finding a therapist” post, or use that post to help them through the search process, if you deem this appropriate. 

A vision and an orientation

To review, the three core convictions one needs to have internalized—implicitly or explicitly—in order to function as a builder are:

1. “I am capable of building X [be it: a startup, the habits and skills of a successful college athlete, etc].”

2. “Building X is worth it to me, as judged in reference to my own long-term needs and values.”

3. “Building X will only happen through my own chosen work of understanding and enacting X in reality.

Abstracted to the broadest level of X—where X is “my own fully lived life”—these three convictions sum up to a vision of the human potential: the vision of a self-directed thinker and doer who is at home in the world; who is equipped to handle whatever challenges life might throw at her, and turn them into rocket fuel; who has formed her own authentically ambitious vision of a life worth living, and thrown herself into the complex, messy, fallible work of making it real.

If we want to help others understand and embrace this vision of their own potential in any given domain of their lives—and thus, at least implicitly, in their lives as a whole— we need to believe in that potential ourselves, and to show them why we do. 

This doesn’t mean we “believe in them” arbitrarily, or cheer them on in some empty, generic “you can do it!” sort of way. It means we watch for, elicit, and even demand the best, most capable, most passionately striving and courageous version of them, even if we only catch occasional glimmers of it at first—and we love and valorize that part of them with all of our being. 

Sometimes this may require us to channel what we know and love about the human potential as such—particularly in those moments when a person we’re coaching falls frustratingly short of that potential. What inner wisdom can we leverage to help us re-envision that person’s path from here to there, and to get reinvigorated for the work of guiding her toward it? Perhaps it’s the memory of that coach or mentor who pushed us to be our best, most authentic self; or perhaps it’s the calling to give her the kind of visibility and genuine respect we never got when we were trying and failing to be our own best selves. Maybe it’s a favorite fictional character or movie scene that viscerally captures the work of becoming a builder in our minds. More likely it is an idiosyncratic, ever-evolving combination of many such particulars and of the emergent meanings and connections between them.

Whatever it is, we must reach deep within ourselves to find and connect with what makes this idealistic vision fully real and meaningful to us—so that we may then do the same for the people we coach, and ultimately teach them to do for themselves. 

Facilitating the work

Recalling that it’s ultimately through the work of building that one develops a builder’s mindset, our main task as coaches is to facilitate people’s work of building—i.e., of understanding and shaping the relevant aspects of their world, and themselves alongside it. 

How do we get a person engaged in the work of building? Obviously this varies depending on the particular context and domain of endeavor, but a universal element is that we need to connect with her around something real in the world that she is already energized (or could easily get energized) to understand and act upon. This could be something as specific as “this project due next week” or as general as “my outlook on relationships”; but it needs to be anchored to the person’s life in reality (as opposed to hypothetical worries or fantasies utterly detached from her life, for example), and it needs to stir at least some emotion in the person we’re coaching. 

With this concern as our entry point, we should be able to invite her into the collaborative work of 1) understanding the concern more fully, and 2) deciding how she wants to act upon it. 

Often this is achieved through open-ended questions like:

• What’s on your mind? 

• How are you feeling about this and why? 

• What’s your understanding of this situation? Based on what?

• Could there be any other way to understand it? 

• How similar or different is this from that other time you felt and thought X? How did things turn out then? 

• What are your needs, goals, and choices in this situation? 

• What are the likely consequences of each one? 

• What obstacles will get in your way? How will you overcome them?

Whatever the particular questions or concerns we jointly grapple with, our background knowledge of the builder’s mindset—together with whatever domain expertise we bring—can guide the questions we ask, the observations we share, and the hypotheses we put forth. 

For instance, if we notice an implied lack of agency in the person’s account of her situation, we can interrogate this with reference to what we’ve noticed about her ability to solve problems and assert her needs in similar situations—or of others like her who’ve found such powers within themselves in such circumstances.

Or if her understanding seems distorted by certain motivated pretenses or rationalizations (e.g., if she’s making excuses for why she’s just “not ready” to take that next important but scary leap in her career), we can gently call her out on this—not from a place of scolding, but of firm conviction that she’s capable and worthy of actually building her best life, not just pretending to.

Know what the work looks like

Having a builder’s perspective on the work of understanding should also sensitize us against the assumption that a person has understood something just because we’ve said it to them, or even because they’ve said it back to us. This applies even to a person’s judgments about the builder’s mindset itself, such as whether they truly have agency over what they build, or whether building is even the right end to pursue (e.g., “isn’t it selfish to focus on building my own career when so many others are unemployed?”). 

Indeed, some of my most genuinely and constructively engaged coaching clients have been the same ones who’ve questioned and disagreed with me most vehemently, at least in the beginning. For instance, some clients might initially question my confidence in their ability to handle a tough conversation they’ve been avoiding. When I point to instances where I’ve witnessed them handling similar or tougher challenges, or qualities I’ve noticed in them that I generally know to be powerful sources of human resilience, I see them weighing my answer thoughtfully—neither rejecting it reflexively nor accepting it at face value. Often this leads them to generate further examples of their own, or to elaborate on my thinking and connect it to other ideas or frameworks they’ve encountered, or follow up with clarifying questions. This is the work of building knowledge, and I make sure to encourage and celebrate it accordingly. 

This looks importantly different from the kind of defensive disagreement that stems from insecurity (which nearly everyone occasionally slips into, especially when confronted with ideas that challenge them to their core). I’m talking about the kind of honest, constructive disagreement where someone is really grappling with a new idea, weighing it against the sum of their own knowledge and experience, and trying to reconstruct it for themselves. 

Know what disengagement looks like

What, then, if the person we’re coaching does not show signs of genuine engagement in the work? For instance, what if they defensively deny or passively acquiesce to whatever we tell them, give minimal responses to our questions, or repeatedly say they’ll take certain actions based on what we discussed and then neglect to do so? 

Assuming we’ve already exhausted our efforts to connect around something real in the world that matters to them (and that falls within the scope of our agreed-upon coaching role), the first concern to connect around is that they don’t seem engaged in the coaching work—and thus aren’t getting the value that coaching is meant to provide. 

Here it’s crucial to remember that our work of understanding the other person’s experience is also complex and fallible, so it’s best to present our impressions as questions or tentative hypotheses, until and unless we’ve gathered enough evidence to be truly certain. For instance, we might start by sharing that “I feel like something about this isn’t really resonating; is that also your sense?” rather than “Why aren’t you doing the work?”

Depending on the nature and strength of our relationship, we might also share that we aren’t getting what we value from the coaching work either—since we’re in it to inspire and empower, not to lecture and dictate. 

Sometimes calling attention to the disengagement will be enough to raise the stakes and inspire the other person to lean in, whether by giving us feedback on what’s not resonating about our coaching approach, or sharing what made it hard for them to engage in the first place. Other times they won’t be ready or willing to engage—in which case we may need to end the discussion and invite them to reopen it when they’re ready. 

Whatever approach we take, it needs to reflect our conviction that building is work—so if we aren’t engaging a person in work, then we aren’t really helping them build. A good heuristic is that if we find ourselves “working harder” than the person we’re coaching, then we’re probably not doing the right kind of work. 

The coach’s inner work

This builder’s orientation to coaching is a departure from mainstream approaches. It means that coaching is not primarily about getting people to learn the particular facts or achieve the particular outcomes we’re coaching them on, nor about providing a nonjudgmental safe space, though these will often be the right means to our ends; it’s about inspiring and empowering people to take maximum ownership over the judgments they form and the outcomes they enact in the world, including whatever failures they must acknowledge and deal with along the way.

Encouraging someone to choose and achieve her own ambitions, and holding her accountable as she does so, is harder than either pushing her toward some conventionally defined form of excellence—like “winning the championship” or “getting a promotion”—or standing by while she coasts through life without any particular ambition. It means constantly resisting the internal and external pressure to slip into one or both of two inertial defaults: imposing goals and standards on her (a la a drill sergeant), and shielding her from the impact of her choices (a la Zen master).

On the one hand, we will be tempted to lean on standard recommendations and performance metrics so we can feel as if we know what we are doing—even when those recommendations and metrics don’t really fit the distinct needs and aspirations of the person we’ve coaching. For instance, we may skip the step of actively listening and really trying to understand a person on her own terms, and instead jump to offering solutions or setting goals that may or may not fully resonate. The implied belief we manifest at such times is that she is not in charge of building her own life; we are.

On the other hand, we may be tempted to indulge her unconvincing excuses for why she couldn’t choose a more ambitious goal or achieve whatever goals she’d set, not because we genuinely believe this will serve her in the work of building, but because we want to spare her feelings. At times we may not even notice the subtle ways we try to cushion people from the struggle, uncertainty, and discomfort that the work of self-creation inevitably entails. For instance, we may jump to reassure her out of her anxiety (“don’t worry, you’ll do just fine!”), instead of trusting in her ability to tolerate the uncertainty; we may inadvertently collude with her BS rationalizations of why she could not have possibly prevented a painful setback or failure, instead of empowering her to own her mistake and learn from it; or we may avoid or sugarcoat the really difficult, uncomfortable conversation about her distracting body odor or revealing style of dress, rather than increasing her awareness and agency over how she presents herself. The implied belief we manifest in these instances is that she is incapable of the work of building her own life.

Minding what we model

Part of the challenge here is that we need to own the work of understanding, internalizing, and applying the builder’s mindset for ourselves even as we coach others to do it for themselves. This doesn’t mean we never feel deep self-doubt about our capability to build anything of value, or that we never feel resentment toward the hard work that our chosen projects require. But it does mean we must work to catch these feelings and interrogate the underlying assumptions as quickly as possible, so we can bring our considered judgment to bear on what we actually do (and, thus, what we model in our coaching).

For instance, we may need to check our defensiveness in response to someone’s critical feedback on our coaching, lest our own insecurity causes us to miss what they’re trying to tell us. Or we may need to reassert the value of our time when we find ourselves compromising our own needs and boundaries to accommodate someone’s demands for coaching. Or we may need to remind ourselves that “there are no shortcuts” or “this is the work I chose” when we find ourselves avoiding the really tough conversations with someone we’re trying to coach, or blaming the “stressful job” for our underpreparedness. 

All of this gets easier with practice, of course, just like any other perspective or habit we work to build into ourselves. But it never becomes effortless, and it never ceases to be a choice. The only way to inoculate ourselves against going too far down any of the various roads described above is to accept that we will sometimes go down them, and embrace the work of catching and reorienting ourselves as often as necessary. 

Embracing the work

Like any worthwhile human endeavor, the work of coaching eludes easy recipes and quick fixes. While it helps to familiarize ourselves with the various traditional coaching frameworks and resources on offer (I’ve amassed a good number of these resources in a much longer document that I’m happy to share on request), none of this material can substitute for the coach’s work of grappling with the full complexity of an individual’s experience, learning to speak that person’s language, and making nuanced judgments about whether, when, and how a given concept or exercise can be authentically assimilated into their understanding and self-development. 

This is the terrifying and wonderful and inspiring work of coaching someone to build. And it is our best path to a world filled with thriving, confident builders.