People Management and Team Leadership

Managers and “stupivisors” are generous founts of comedy and derision in our popular culture. Michael Scott. Mr. Burns. TPS Reports. Chances are pretty good that none of these names conjure up a particularly flattering view of management or leadership. And I think this is quite a shame considering how much of our professional lives we spend, or will spend, under the management of another.

To further complicate matters, the vast majority of managers find themselves managing in multiple directions: down to their direct reports; across to their cross-functional contemporaries; and up to their own boss(es). Given the multidimensional quality of people management, it’s no wonder we managers (yes, I’m one) manage to strike out as often as we do — we take a lot of at bats. So it is worth considering a common grammar and framework to improve our impact as managers.

Let’s start with managing down to a team of direct reports.

First thing’s first: management is not the same as leadership. To be clear, this is not an original idea of mine. And yet it is easy to trivialize. Management elicits compliance either through fear of some punishment or hope of some gain. Leadership, by contrast, means inspiring a voluntary choice to follow.

Here’s the difference.

One can lead through fear of deprivation. “Do this or else you won’t get a bonus.” “Complete this by Friday or else I’ll give the next assignment to someone else.” Or simply, “Do this because your job is on the line.” To be sure, these are hard nosed tactics and may not always fly in certain settings where policy or decorum dictates otherwise. But I’d venture to guess that this is the framework — the proverbial stick — most people have in mind when they think of “management.”

Of course, one may also manage through reward and incentive. This is also a form of manipulation, albeit more benign. What does this look like? This is the proverbial carrot: “Accomplish this and you’ll get a bonus.”

Now, candidly, either approach can work a short while because we’re all somewhat conditioned to respond to them. And, honestly, should be part of a leader’s arsenal. But the mistake many people manager’s make is that they fail to diversify their leadership toolkit.

In an ideal world, people would follow you, not because they fear recrimination, and not because they’re compelled by personal financial gain. But because your vision of a path and destination a naturally aligns with where they want to go as part of their own personal or professional development.

How do you do this?

First, start by making your path and destination explicitly known. Your team cannot willingly follow you if they don’t first know where you plan to go: Want to build lean team of legal generalists? Say so. Or do you want to build a bench of seasoned subject-matter experts? Tell them so they’re not surprised. Do you envision building a vertically integrated legal team or more of a matrix style? Whatever the course, tell your team, first and foremost.

Next, expressly invite your team for the ride and make clear that the ride is optional. We all know from experience that employees do not always buy into the strategic vision or direction of a company, yet they suppress voicing opposition for fear of recrimination. This is a destructive paradigm, in my view. It is also completely fine to acknowledge differences of opinion.

Finally, and critically, ask your team to hold you — the leader — accountable to the direction you have set. Give them a mechanism to provide feedback like a regularly scheduled check-in or survey. Now, this is hard to do because feedback always invites criticism. But, as a leader, you need the wherewithal to consider feedback of all sort, and to turn it into action for the benefit of your team.

Personal Lessons About Team-Building

Over four years ago, I was tasked with the enviable project of building from ground zero an in-house legal and compliance team at Affirm. Given my dearth of prior experience, I had no business managing such a project, and each hiring decision was fraught with self-doubt: could I successfully harness this person’s talents and experience without outing myself as a fraud?

Four years and dozens hires later, I’ve grown more confident in my team-building role though I find it no less challenging — and certainly no less critical — today than it was on day one. With typical year-end reflection, I thought now would be good time to reflect on and share three lessons learned.

Get over yourself: Your new team members in many ways will, and should, be more talented and forward-thinking than you. After all, this is precisely why you’re hiring them. One person alone cannot possibly have perfect knowledge and judgment, and it is unreasonable (and potentially stupid) to think oneself master arbiter of all questions. Healthy dialogue with a talented team will always yield better results.

Share information early and often: Think about the onboarding process and how you might best set up your new teammates for success. Transfer your knowledge about the business to each new hire in digestible, actionable bites. Who will be their primary points-of-contact for the lines of business they’ll support? What are those personalities like? What are the organization’s communication channels? The more efficient this knowledge transference, the better your new teammates will be able to bring their unique expertise to bear.

Think ahead 2-3 years: When we started building the legal and compliance team, it was very tempting to hire for more immediate and discrete needs. Luckily, several friends and colleagues advised against this temptation and urged me to think about higher potential candidates that could grow a job function instead of just “keep up” with a job function. This is admittedly challenging particularly when staring at a mountain of immediate work. Still, it is well worth taking the step back and thinking about what the needs might look like 2-3 years out.

Accept change: The team you build today will not be the team you keep. I’ve been struggling with this a lot lately because of some recent “regrettable attrition.” Change is a fact of life, and it can be quite healthy by forcing a hiring manager to constantly consider retention. But even when your team inevitably loses a high performer, it could be because of the opportunity you, the hiring manager, afforded them. That has to be worth something. Besides, people can always decide to return.

Building the legan and compliance team at Affirm remains the most rewarding and challenging experience of my career, and I am thankful for the opportunity to have “learned on the job.” In sum, I suppose the biggest lesson I’ve learned is that it’s okay to not have all the answers. But it is important to ask the right questions even at the risk of revealing ignorance. After all, teamwork makes the dream work.