Dedication and Fallibility

I recently debated a policy issue with a longtime advocate who had spent their career researching and writing in support of a particular perspective. I, in turn, expressed a contrary viewpoint. My basic thesis was that certain policy prescriptions of the past had failed to yield the intended results, and that the underlying assumptions needed to be reviewed. This went over like a lead ballon. The advocate dug in and reminded me that they had spent 20+ years studying and supporting their particular perspective. The not-so-subtle implication seemed to be that I could not possibly be correct since I had not dedicated the same amount of time during the course of my own career.

I should acknowledge two things right upfront. The first is, while I haven’t logged as many miles as some folks, my experience is not negligible. I usually don’t wade into territory about which I know nothing about, and my views on this particular topic are not entirely uninformed.

Second, I should note that I generally like and admire the advocate with whom I disagreed. Maybe they don’t believe this and maybe it doesn’t matter to them. But it sure matters enough to me to acknowledge that, despite the political and social climate of the past few years, it is still possible to disagree respectfully and with admiration intact.

And this is precisely why I was so disheartened during this exchange. No, it’s not because I unsuccessfully swayed the advocate’s opinion. Rather, it was the categorical unwillingness to consider an alternative perspective because of what it might mean for the person’s 20+ years of advocacy. The fear, left unstated, seemed to be that if this person’s sincerely held belief turned out to be wrong or incomplete, then the person’s 20+ years of advocacy would have been all for naught. To my mind, this kind of thinking aptly illustrates the sunk-cost fallacy. And the problem with the sunk-cost fallacy is that it is, well, fallacious.

What I wish I could convey to this advocate is that their 20+ years of dedication is no less valuable or admirable by shifting one’s perspective. I wish I could convey that all of our perspectives are subject to change amidst a changing world with changing facts and circumstances. And that it is not at all a sign of weakness to show some degree of elasticity in one’s perspective but, rather, it is a sign of strength and courage. These are the things I wish I could have conveyed but for the advocate’s categorical refusal to be proven wrong by anybody.

Of course, I could be wrong. What the hell do I know?

Leadership During Crises

Newsom. Cuomo. Trump. Each has responded to the COVID-19 crisis with a different tact. Newsom transparently relays realtime data to Californians. Cuomo has embraced the structured slide presentation sprinkled with anecdotes about his family. And Trump, well, apparently he wants to disinfect your innards

Leadership in crisis is more art than science. We all know good leadership is sorely needed in a time of crisis, but few can point to a playbook because, by definition, an unprecedented moment lacks precedent. Still, there are some immutable principles that would well serve the leader in all of us in a time of crisis.

Connection is paramount in this moment given the various shelter-at-home mandates (or guidance, depending on your views). As of late April 2020, good chances are that your local traffic is sparse and parking plentiful. And if you’re like me, you’ve seen the same four faces — no more, no less — everyday for the past month. Whatever broader community we previously belonged to isn’t as visible, hence, rise of the zoom happy hour and virtual dance party. And thank goodness for these outlets because they allow us to remain connected in this weird time. Leaders can use these outlets to help their organizations feel a strong, empathic connection to one another despite being physically distanced.

Leaders should also relay timely information to their organizations. Whether good news or bad news, there ought to be healthy information flow from leadership to the rest of the team. This serves two purposes. First, it helps sustain an organization’s mission alignment, whatever that may be. If your organization’s mission is to spread love and joy, then your organization needs to hear that message reinforced in the midst of a decidedly joyless situation. Second, sustained information flow helps organizations stay motivated in uncertain times when individual team members are all experiencing personal interruptions.

Next, leaders must provide direction in a crisis. Where do we go from here? When will this end and will my job survive this all? Because it’s not enough to know that you remain connected to a broader team and mission. A leader should lay out a vision for what follows, good or bad. Be a rudder. Now, it is all too tempting to forgo this piece for fear of being wrong. Call me crazy but I believe organizations are far more forgiving of a course-correction so long as the leader is forthright about their operating assumptions. This brings us to a final and perhaps most important principle…

Leaders must embody honesty. Because the only thing worse than a crisis itself, contrary to some belief, is a lie about the cure.

Death to the Pre-Call

Conference calls, previously shunned by technologists and social-media acolytes, have reemerged with great vigor in our socially-distant work environment. More equitable and less invasive than a video conference, a conference call satisfies the need for real-time discussion. It allows cross-functional teams to check in on the status of things, and gives managers a sense of control.

Read on…

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.