My Leadership Philosophy

A founder I worked for was a big fan of the “rule of three” — the idea that naming principles, concepts, objectives, what have you, in a quantity of three makes them easier to remember because human brains cling to patterns. So I got in the habit of building frameworks in threes. Three JTBDs (jobs to be done) for the year, three insights extracted from a campaign analysis, three proof points of a consumer tension at the heart of creative work. (See what I did there.)

And when it comes to leadership, I find clarity and consistency are of paramount importance. Clear is kind, as they say, and consistency builds trust and credibility. So all the more reason to establish precisely three principles that represent my leadership style.

Importantly, these are principles I both a) commit to those I manage and who manage me, as well as b) expect from my team — expectations I have of them towards me, but more importantly to each other. They’re three tenets that describe how I operate in the workplace. They represent how I build a team and how I act as a corporate citizen.


ACE

ACCOUNTABILITY: Do what you say you’re going to do, when you say you’re going to do it.

  • I believe when there’s inherent trust that what was committed to will be done, on the timeline on which it was committed, there’s zero need for micromanagement. There’s no wasted time on following up (I always say a fairy dies every time you have to send a follow-up email to chase something down), and there’s no low-grade frustration that someone has to carry more than someone else.

  • Also, I believe having a clear owner and timeline for action items gives everyone peace of mind — again, clarity is kind — and alleviates the burden on anyone who always step up to take something on if there’s no defined owner. I think RACIs are confusing (how can you be responsible for something you’re not accountable for?) but I like Twitter’s DACIN model: Driver — Approver — Consulted — Informed — Next Steps.

COMMUNICATION: Be transparent and upfront about the good, the bad, the ugly, AND THE MUNDANE.

  • I believe in starting and ending the week strong, bookending it with a “Magic Mondays” team meeting and a “Failure Fridays” team meeting. In the former, we go “around the grounds” to share any highlights from our weekends, then review the week ahead. Depending on the team mandate we may also review business performance or do a pulse check on progress towards our goals. We may have a quick guest speaker. The idea is to kick off the week with positive and productive energy. “Failure Fridays” is exactly what it sounds like — each person (I go first) sharing one thing that failed that week and what we learned from it. Doofy names for meetings, sure. But a) it makes them easier to remember, and b) it turns the sometimes-dreaded team meeting into the possibility of something enjoyable, unexpected, or at the very least a worthwhile use of time.

  • I believe in clear visibility for people on progress and plans. Unless there’s an SEC- or NDA-related reason not to disclose something, there’s no reason to withhold information from people. “Pay grade” is B.S.

  • I also believe in handling moments of truth face-to-face, i.e. not over audio call. Fantastic news, difficult conversations, big changes.

  • Relatedly, no one loves surprises in a business context, even good ones. So I believe the more proactively we communicate as a team, the more trust we build; the more prepared we are when things inevitably miss the mark or circumstances change; and if something’s bothering someone, the better I can help make it right.

  • Lastly, if it’s not obvious by now, I believe strongly in #clarityandconsistency. To me this means creating and committing to a simple strategy everyone understands, and rallying everyone around that strategy by virtue of it being… well, clear and consistent. There’s a lot of security in knowing where we’re going, why, and what it looks like when we get there. It’s easy, especially in a startup or a matrixed organization, to fall down rabbit holes or get distracted by tangents — and of course I believe strongly in flexibility and nimbleness no matter the size or age of the business. But, whenever possible, diversions should fall within the strategic framework for that period of time (quarterly, or even monthly, plans work great in high-growth businesses since things change so often) to avoid overwhelm. In other words: don’t throw missiles.

EMPATHY: Care for each other.

  • I believe time is precious. Being a work parent, or having a time-consuming side hustle or hobby, throws this into relief: being intentional about every hour of the day is key to managing professional and personal productivity and fulfillment. “Time is precious” in action looks like meeting optimization: agendas and pre-reads circulated before, actions, owners, and timelines circulated after; no unnecessary people included; memos for things that don’t need to be meetings at all. And, as time zones and busy periods allow, respecting other people’s calendars, i.e. not scheduling meetings over other meetings. “Time is precious” also looks like, as a leader, modeling turning off work on vacation, holidays, and whenever else is appropriate in the context of the organization or your stated boundaries (for example, reserving 6:30-8:30PM for family time during which your phone is shut off). The old “even if I email you outside work hours, don’t feel pressure to respond” trick = not a thing.

  • Empathy, to me, also means no “fiddling” — for example, making tiny, unnecessary changes to decks, because that’s petty and disempowering — and no busywork whenever possible — for example, time-consuming updates or recaps outside the normal flow of business operations. Depending on the complexity of the org structure, there will always be some degree of bureaucratic requirement for optimal cross-functional and hierarchical workflow. But I believe we can maximize time spent on this by, for instance, standardizing formats and processes.

  • I believe in, as I learned from Danny Meyer during my time at Shake Shack, making a charitable assumption — in other words, assuming positive intent. So much interpersonal workplace tension can be avoided by collectively agreeing we all have the same aim in mind — the success of the business, and by extension each other’s success. As Jacinda Arden put it, I refuse to believe that you can’t be both compassionate and strong.

  • Most importantly, and I stand by this above all principles in my leadership philosophy: I believe in listening for people’s time signature. I’ve been a jazz drummer since elementary school, and one of the fundamental elements of jazz music is the time signature. Traditional jazz songs are in 4/4 time, the typical 1-2-3-4, 1-2-3-4 rhythm we’re used to from all popular music, because they’re easiest to dance to and that’s what jazz, or swing, was once all about. But often jazz is in 3/4, or 5/4, or 9/8, or other unique time signatures. The job of the drummer is to hold down the backbone of the tune, keeping the beat steadfast for the rest of the band, even when the time signature is less comfortable or familiar. As a listener, you can find the time signature of the song by tuning into the drummer’s beat and the bassline. Sometimes it takes a few minutes to pick up the groove, especially if it’s during a solo section when the soloist is bending the time signature even more as part of their personal expression. In a work setting, listening for people’s time signature means taking heed of their personal OS, their individual operating system. What motivates them, what’s their sense of humor, what makes them feel heard and respected? What soft and hard skills are they working on? What are their aspirations and how can you help them get there, either within the confines of the organization or outside it? Is anything going on in their personal life that requires more space, or more flexibility, from work? You can ask people questions outright to get at their style and preferences, as part of onboarding or team personality assessments and whatnot (the latter are fun and a good exercise in self-awareness but maybe questionable in terms of validity). But my approach is to pick up on cues through working together, and slowly adapt my style — how we use 1-1s, how I give and ask for feedback, what channels we use to communicate, how we career-plan — to that person as we learn each other.


Accountability, Communication, and Empathy. ACE. Pretty straightforward. But I’ve found, after managing people for 12+ years, and being managed by people for longer, it’s a helpful tool to convey the rails our team will run on. When we’re all operating with these principles in mind, we get more done, faster; and we have a better time doing it. You can count on each other, you’ll never be in the dark, and you’ll always have each other’s best interests at heart — and you’ll know the shape of each other’s worlds, since you can’t empathize without insight into someone’s personal life. (Plus, I just think it’s weird to spend one third of your life with people and not know if they have a dog, or whether they love fly fishing.)

Like any approach to leadership, I developed these principles over time as a combination of attraction to how I thrived as an employee, and reaction to how I experienced less impactful management. Leading people — not just the act of it, but actually caring about how it’s going and diligently reflecting on and improving the craft of it — takes no less (in fact, more) attention and care as delivering whatever your work product is. I consider it a great privilege to manage a team, as you have outsized impact on those people’s experience of work, which affects their life as a whole.

Above all: having accountability, prioritizing strong communication, and leading with empathy requires being adaptable to company and team culture. Every business has its inherent systems, norms, and vibes, and every team within the business is composed of individuals who create their own climate by virtue of being human. So the above leadership philosophy looks and feels a little different depending on the organization I’m operating within. It’s been a really stimulating professional experience being exposed to such a wide range of companies, from startups with 300 employees to international Fortune 200s with 300,000 employees. How people create and collaborate looks a lot different within these different contexts, which means approach to leadership must, too. But the fundamentals stay the same: Accountability. Communication. Empathy. We figure out the rest together.

Allison StaddComment