Hi, I’m Sean, a Silicon Desert technology leader. I’ve gotten enough of these “what’s your management philosophy?” questions to warrant writing it up. So here it goes…

Sean on Management

I believe in Agile management, grounded in the servant leader concepts I learned at Accenture and elsewhere. I’m also a fan of the radical candor I picked up on at AWS. Which is to say,

I’m here to support my direct reports, to add vision and context⁵ to what they’re being asked to do, to set 360° expectations, and to provide regular feedback on the team’s tracking towards those expectations.

I like big, hairy audacious goals (and a lot of Jim Collins’ work in general). I start with the big picture (often on a whiteboard) and, following Agile, break it down into meaningful but workable chunks. Ideally, those fit within a sprint/iteration and get assigned to an owner. However, there is no DRI, as success has many fathers, Agile epics many stories, and stories many sub-tasks.

Failure is something to be celebrated when done fast and gracefully. From blameless postmortems to spikes that didn’t pan out, every step is an opportunity to learn and find a better path. This is called a Learning Culture, and it’s critical in the recipe for success in a competitive business environment.¹

Accountability and professionalism are required for any of this to work. As Amazon says, “Leaders ensure that defects do not get sent down the line and that problems are fixed so they stay fixed.”

I believe in empowering teams to own their full-stack - whatever that stack might be, they need to be able to act as the owners of it. Period, full stop. I use team chartering to help set and enforce the team’s ownership boundaries³ and then encourage them to iterate quickly within those boundaries using the decision-making framework Bezos borrowed from statistical hypothesis testing. To distill it,

Most day-to-day and sprint-to-sprint decisions are Type 2. They should be made by the team that’s as close to the problem as possible. It’s okay to pivot on these. I, as management, generally don’t need to know the details. I should instead be investing my time in the Type 1 decisions.

I’m an advocate for work-life balance. All things in balance, really. If you’re looking for how I stay cool in a crisis, this is it. I have a simple framework for fitting it all in. YMMV, but it’s up to you to set your boundaries. I might produce or respond to asynchronous communications at any time of day, but I make it clear to my direct reports that outside of production down, there is no expectation of response until their next scheduled working hours. I also try to be clear if a response is required, at all, and if so by whom (@ tags are great). We’re all adults and I’m not going to micromanage when work gets done, only that it is done and done to expectations. As long as commitments are met, I don’t need to know when you step away for a few minutes for your mental or physical health or family matters. Keep your calendar up to date, and I have your phone number for production emergencies.²

Some additional leadership concepts I often lean on:

• Theory of Constraints (Removing one just highlights the next)
• Sunk Cost Fallacy / Bygones principle (Only take into account the future costs and benefits when making decisions)

"You can't make up for things that have happened in the past. You just got to think about what you're going to do moving forward. One play at a time." - Tom Brady

• Project Management Triangle/Diamond/Triple Constraint (Good, cheap, fast. Pick any two.)
• The Triple Bottom Line

Sean on Meetings

I was once at a client site that went so far as to post laminated “meeting rules” in each conference room. It may sound cheesy (and we laughed at the time), but each of those rules has become a norm in time. With some paraphrasing:

1. Have a set agenda and stick to it.

It’s easy to get distracted when you’re talking to people you like, or if it’s your only meeting of the day with a person with key information you’d like to hear. But by choosing to derail, particularly for a topic only a few participants are interested in, you’re costing the company a lot of money. I have a penchant for getting right to the point in any meetings I schedule not because I’m not interested in furthering our personal connection via small talk, but because I’d like to be a good steward of our company’s investments. I will also steer the group back towards the agenda because I’d like to...

2. End at least five minutes before the hour or half-hour.

This breaks the cycle of everyone being perpetually late to every meeting from having back-to-back meetings with no travel, setup, or bio-break time. Google Calendar calls this scheduling setting speedy meetings, and I keep it on.

3. Be inclusive of remote participants.

This was before the age of Zoom, and it focused on not having side conversations in the conference room that distract phone participants from hearing the main meeting, or conversely muting and having the remote participants wondering if they’re having connection problems or missing out on some camaraderie. Inclusion can be even better now.

My biggest pet peeve is recurring, agendaless meetings. Given the chance, I will rant about the bad meetings eating up my calendar. But Ben Hilburn is more articulate on the subject. According to Godin, there are three types of meetings:

• Informational
• Discussion
• Permission

The first and the last can be emails or other forms of asynchronous communications, leaving discussions and their resulting feedback as the most valuable to be worthy of investments of synchronous meetings. But before we can have a meaningful discussion, the participants must have a similar starting point.

Enter the narrative. It doesn’t have to be six pages, and it doesn’t have to be prose. It could be an architecture diagram, or an outline, or a working prototype. A living artifact the meeting participants can absorb on their own time before the meeting. And yes, if someone hasn’t reviewed it before the meeting, I will stop the meeting to give them the time to review it. This practice promotes inclusivity. Every participant of the meeting should have something to add to the discussion, and if upon reviewing the document the participant realizes there’s nothing for them to add, it should be okay for them to decline the meeting or drop midway through it. Flow is critical to productivity, and I’d rather my employees stay in flow than be in meetings all day. If it was up to me, maker time would be mandatory.

Finally, we generally work across time zones. Very few companies got to true Agile team colocation before the pandemic, and even fewer will be going back to full scrum team colocation after. So if you’re going to schedule a meeting, be mindful of the schedules of those you’re inviting. After mastering “this meeting could have been an email,” consider the nuances of asynchronous communications.

Things You Should Know About Me

We all have personality quirks and I’m no exception. You can learn about my personal and interaction style in my Insights Discovery Profile. Things I can remember getting called out include:

• I have a Bias for Action. This combined with my preference for Dalio-style radical transparency can rub a Minnesota Nice person the wrong way. I grew up in the Cincinnati metro which has a weird linguistic link to New York City. Between that and my dad originally hailing from the New York City metro, I can exude that culture sometimes. But I prefer West Coast culture, I swear.
• Speaking of swearing, it’s a sign of honesty, core to one of those Accenture values. If you hear it from me, this means I’m letting my guard down and trying to better connect with you. If you’d prefer my guard up, let me know.
• I cohabitate with my spouse and kids and pets. Don’t get offended if I’m working from home and my camera is off. It might be chaos behind me, and you don’t need that distraction. But if you want to see a pet, the rules are the rules.
• I try to overcompensate for tone via chat, but it’s harder to do so via email. And I will probably overanalyze your tone in either medium. So as a rule of thumb please assume positive intent from me, and I’ll do the same for you.
• I don’t like coffee, but I will meet you at a place with smoothies, or at the pub. The sentiment is the same.

1,2,3,5: The five keys to a successful high-performing team