Position for success
Success is achieved by first understanding what failure looks like.
Contents
Leadership Moments: Snow Crash
One Minute Pro Tip: Meeting Death Criteria
Chapter Teaser: Uncertain Futures
Appearances
(paid) Cutting Room Floor: Matching your team to the environment
Leadership Moments: Snow Crash
The worst snowfalls in Boston are the heavy, fat snow that starts mid-afternoon on a weekday. Of course everyone is at school or work, and now the commute is awful. Plows aren’t able to clear the roads that are full of cars, every town clears at a different rate, and it can be a recipe for disaster. And for some of those drivers, it’s one of their first snowfalls, ever.
Our daughter got her license to drive only three months ago. It’s been wonderful not having to make the roundtrip drive twice a day every day, especially since she and her brother are in the same school. She was confident that she could make the drive home, but her brother, who had been on a school trip that day, and watched the commute get worse and worse, was less convinced.
We’ve reiterated, time and again, that, if you’re not comfortable driving or being driven by someone, call for a ride. We thought we were planning for a situation where alcohol might be involved, but our son felt safe texting us that he’d rather we come pick them up (so we did, and our daughter drove one car 95% of the way home with me as her passenger, until we got to a steep icy hill, where I took over and promptly ran the car into a curb, but that’s another story).
We thanked and credited our son quite profusely for making the initial call – and thanked ourselves for making a safe space for him to raise his concern. Whether you’re parenting or leading a large organization, you need to create that safety to let risks get escalated.
One Minute Pro Tip: Meeting Death Criteria
Everyone laments having too many meetings on their calendars, but are you actively out killing your meetings? Every recurring meeting you’re in should have death criteria: the things which, when they become true, will let you end the meeting series. Now you can actively pursue those outcomes, because the goal of your meetings is always to coordinate making change happen.
This is true even for the one-on-ones you have with your staff. They aren’t just checkins, they’re your opportunity to develop your staff so that you can promote them out from under you. Every tactical topic is an opportunity to teach them and give them more responsibility. If you’re checking in on the work they did since the last meeting, can you exchange updates in writing to evolve the meeting to strategy for the next week, month, or year?
One of my colleagues was even more blunt: they’d list the death criteria for specific meetings. If those things became true before the meeting happened, the meeting would be canceled. This was a great way to incentivize engineers: do this 15 minutes of work and avoid a 30 minute meeting.
Chapter Teaser: Uncertain Futures
Chapter 15: To engage in the present, be of two minds about the future.
It's easy to get wrapped up in "What-If"s about the future. When one of those futures is very scary, it can keep you from navigating a path towards a more successful future. But if you can embrace the worrisome future – explore it, roleplay it, accept that it might already have happened, process the emotional baggage that comes with it, and then temporarily lock it in a mental closet – you can free yourself, and your anxiety, up to be able to engage in planning for a better future. You might not always get to control your destiny, but you can keep your destiny from controlling you.
For leaders, getting trapped worrying about the possible futures and stuck in analysis paralysis becomes a recipe to create even worse futures. It’s acceptable to acknowledge the bad future, but don’t let that keep you from directing your team to make the better outcomes possible.
Appearances
If you missed my Jan 24 Budgeting for Cloud Security webinar, it’s recorded. My guests had a lot to talk about leadership in the security budgeting process.
Just published “How to Find and Hire Cloud Security Professionals”, but it’s a blog post that has very generalizable tips on hiring.
I’m in Tel Aviv all this week - catch me at the YL Ventures Fireside Chat if you’re in town.
Behind the paywall: the last chapter to be cut from 1% Leadership.
Cutting Room Floor
This chapter was the last one to be cut from 1% Leadership, so while it had some editing, it didn’t get the full set of editing that went into the book. It discusses understanding if success is even possible before you start a project.
A great football team will be much less effective if they’re playing in a hockey rink.
“TEST: A meteor has struck the headquarters” –incident subject line
Managing organization-wide complex incidents is often a problem that reduces to “send a lot of email around the company.” I suspect that every team that oversees incident management at some point decides that a better system is needed for coordinating that many people; and my team was no different. Some projects we tried were highly successful, but others, despite the herculean efforts of the involved team members, reached the final stages–before failing. All that effort, wasted. But sometimes, understanding why the effort was ineffective can be educational.
Having to hunt through email inboxes to understand what the status was on a given incident had become untenable for me, so I tasked a member of my team to implement something better. An email-based, time-limited incident tracking system was just ripe to plug a ticketing system into it, and off he went. With some entertaining hiccups (an email loop caused the prototype system to reply to itself on a test incident, while also copying most of the company, informing them that the headquarters had just been destroyed by a meteor), the system made it through integration testing, meeting all of the needs of the incident management team, and when it came time to complete its rollout … that meteor strike incident felt like some lazy foreshadowing.
The organization already had a handful of relatively company-wide ticketing systems with email integration. While none of them were really suitable for the problems we were trying to solve, executive stakeholders hadn’t heard that case before we’d built a new system, and now saw any argument to justify the need for a new system as efforts to defend what seemed, to them, like a wasted investment. Most of the incidents already had tracking tickets in two of those systems, so the need for any system wasn’t obvious from the outside. Not only did we end up needing to entirely scrap our project, but when one of the other ticketing systems was being upgraded, we then had to switch to using it, despite its mismatch to our needs.
Not only had we not made the progress we’d invested in, we actually went backwards. The people working on the project had the correct skills to apply to their project, they’d worked with diligence, and they’d achieved everything they set out to do. Even in looking for errors to learn from (not to cast blame, of course), that was a dead end. The real error lay in misunderstanding the organization; the playing field we were operating in wasn’t the one we thought we were.
All of the previous improvement projects had similar stories. Relatively small tools, deployed and maintained by our small organization, which we used to make our jobs easier. They gained wider adoptions organically, as nearby teams saw how we used them and voluntarily adopted those tools. The new system, however, was going to need to be used almost overnight by the entire company. Changing how that many people operate would need delicate messaging, executive buy-in, and was no longer just a technical project. It had become a people and process intensive task, and we hadn’t prepared for that work.
It was a lesson in understanding the constraints on effectiveness that organizational realities put on the value we could realize. Skill and effort were present, but the prep work hadn’t been done to make those useful to us. It doesn’t matter how skilled your team is, or how hard they work on a project. If you put them onto work that is likely doomed to failure from the start, you’ve sent them into the wrong arena for success.
A great football team will be much less effective if they’re playing in a hockey rink.