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Advice to entrepreneurial spirits

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5 min read

To cope with the real-time complexities of the business world, you need two things that markets and contracts can’t provide: leadership, and team spirit. – Matthew Yglesias, Slate, 2013

Spontaneous name changes may be subtle but they’re revealing. Without anyone noticing, at roughly the same time ‘return-to-office’ softened its branding to ‘hybrid work environment,’ ‘side hustle’ replaced ‘moonlighting’ as the common parlance for being entrepreneurial outside one’s primary job. Both are textual skirmish markers in the topic I opened in the October issue, the subtextual struggle over entrepreneurial talent. Both show that in this environment some people have the initiative – but only the entrepreneurial ones.

Leadership. You need people who can survey a situation, think for a minute and then issue directions everyone carries out. 

Teamwork. A workplace where everyone is obsessed with their exact job rather than pitching in is dysfunctional. 

To affordable housing’s entrepreneurial leaders, be they high or low, securely tenured or freshly hired, I offer this advice:

Identify your company’s leaders and get them to know you. Ignore the titles and organogram boxes; who are the people striving to make the company better, make its people and systems better, make its products and services better? Put yourself within their fields of vision.

Decide where continuity and relationships matter to you. For managers, identify the roles where someone’s value rises rapidly with more time in grade. For workers, define where it’s important to build enduring work relationships with co-workers, and which ones. Invest in these, and for the others, see the next point.

Consciously define roles for part-time or gig workers. For managers, which activities lend themselves to outside gig workers, because it takes less than a full-time employee (FTE), the workload is variable or there are reliable people on call if needed? For workers, if you treat only the part of your job that you love as a gig assignment, could you ethically do just that as a side hustle for someone else? 

Define the activities where in-person working together adds value and organize work-week schedules around those. For managers, how does being in each other’s physical presence contribute to leadership, teamwork, learning, recruitment, retention or advancement? For workers, how does working out-of-office contribute to productivity, availability, concentration, innovation or emotional health? 

Don’t conflate digital connectivity with corporate socialization. At best it’s a surrogate.

Have stated rational positions on hybrid work and side hustles. For managers, develop both and communicate them, preferably in writing. For workers, don’t hide your desires for either and why you want them. For both, be clear about the principles you think govern each.

Get upstream of the hiring decisions. For managers, become visible in the public space beyond the trade associations—universities, conferences, LinkedIn, YouTube—and in every medium, have an accessible and authentic message. For workers, invest in continuing education, company-sponsored or on your own, and meanwhile, learn everything you can about the company that employs you. 

Treat recruitment, retention and growth as all part of a long-term mutual relationship. Too many companies treat recruitment like shopping for groceries: choose, buy, shelve, consume. Too many workers treat interviewing like Tinder: swipe right, say what works, try it, and if disappointed, just swipe left. Both approaches are transactional, but primary employment is an ongoing interpersonal relationship between consent parties; success depends on continuing mutual communication and reinvestment. 

Model the behavior you want your counterpart to have. For managers, voluntarily invest in people’s value: hire for attitude, train for skill; praise in public, correct in private. For workers, voluntarily invest in the company’s value: do the dumb stuff cheerfully and well; when working out-of-office, extend yourself to be more productive and more communicative. 

Decide what you value. For managers, how much is employee teamwork and esprit de corps worth to my unit or company, and which workers have it? For workers, how much is admirable leadership worth to my job experience, and do I get enough of it where I am now?

Be transparent about what you value. Whoever you are, your objective is a job-manager-worker relationship that is optimized on both sides, and this is impossible unless you’re transparent about what it looks like. For managers, don’t train, teach; don’t poach, invite; don’t hoard information or visibility, share both; and if you have employees who abuse these confidences, disengage your company from them. For workers, be respectful and forthright in interviews and intra-company dialog. Given the opening, explain what you value in a job, a company and a career path. Say how you personally trade-off compensation, security, upside, personal agency and moral worth.

Improve the frequency, clarity and McLuhanesque implications of your communications. All of us are more comfortable in our own argot. If you’re older, ditch the phone and use tech channels: text, WhatsApp, Slack or whatever comes next. If you’re younger, write emails as you would write letters. Everybody, have protocols and etiquette about the urgency/response expectations of each respective channel.

Look in the mirror and imagine yourself 30 years older or younger. If you’re 30, ask whom you want to be when you’re 60. If you’re 60, ask who you were at 30. Either way, find those 30 years removed from yourself and ask, ‘Is that an avatar I remember being, or an avatar I’d be happy to become?’   

David A. Smith is founder and CEO of the Affordable Housing Institute, a Boston-based global nonprofit consultancy that works around the world (60 countries so far) accelerating affordable housing impact via program design, entity development and financial product innovations. Write him at dsmith@affordablehousinginstitute.org.