Leading... when you're not the leader

How to lead from a position of non-leadership where everyone outranks you and no one cares

I’ve been super lucky to lead a wide breadth of projects, ranging in levels of importance, and also across various disparate project team types. I usually worked with peer teams or led my own teams, but less often I had to lead a team of people to whom I was subordinate. Leading people who outrank you (in common parlance: Managing Up) is quite difficult — especially if you aren’t confident in yourself. However, the opportunities I’ve had leading projects with folks who outranked me led to tremendous personal growth. Two of those projects are laid out in detail below — one from my time in the Army, and one from startups. Big takeaways from both instances:

• Embody confidence???
• Adhere strictly to programmatic best practices ???
• Allow opportunities for vocalizing thoughts/issues/grievances???

Enjoy?:)

Pushing through Institutional Resistance

Circa 2016, the?Army had just opened up combat arms branches to all genders — all gender-related restrictions would be peeled back?to ensure optimal readiness?of all types of soldiers across the force. No longer would we be able to fall back on the narrative of combat arms being a “man’s job”. No longer could the Army preclude someone due to their gender identity from serving in high-profile, prestige-driven positions.

Recently,?Kristen Greist (a classmate of mine) and Shaye Haver graduated from Ranger School, which is?the Army’s elite leadership?course and standard-bearer of infantry leadership capability.?A low proportion of those who start the course pass. The whole event is a 2-month haze-fest in which you are starved and sleep-deprived then required to make leadership decisions. “Thinking through problems in resource-constrained environments” is the corporate translation. My memory of the school is still seared into my mind a decade later — it’s quite the experience. When Greist and Haver graduated, the Army used their success as a “See what women can do” talking point that led to policy reversals related to gender across the force.

I was employed as an operations manager at the Army’s Ft. Benning unit that oversees initial entry training for infantry and armor branches of both enlisted personnel and officers. My task was to develop a standard operating procedure (SOP) for integrating all genders into training environments. The SOP needed to meet a few basic criteria (I’m summarizing):

• Minimize the opportunity for sexual harassment and assault.
• Create avenues for quick-expression of grievance by students to instructors.
• Facilitate construction planning for needed physical boundaries related to changing clothes and using the restroom while in field environments.
• Create a training program for leadership that encouraged support for women as they transitioned into these communities.
• Predict and foresee any opportunities for failure due to gender — not related to ability — and change the conditions such that those opportunities no longer existed.

My boss — a full bird colonel (three ranks above me) — was supposed to oversee the SOP development effort. Instead, he relegated the effort to me. Awesome opportunity for someone with very little experience conducting SOP development for strategic initiatives. Also a really cool opportunity given the team that I was working with: 15 senior-level military and civilian officials, all of whom outranked me, and all of whom had spent their lives in the combat arms community. Awesome opportunity — though challenging from the get-go.

I kicked off the effort with a series of project definition meetings in which we identified requirements, categorized and agreed on them, then decided our overarching mission statement. From the start, the team was intensely resistant to engaging in any kind of conversation, saying things — in an open forum — such as…

• “Let’s just slow roll this and wait for the next president to come into office.” ??
• “Don’t they know this will destroy the Army? What do you think happens when you get men and women together? Bad things!” ??
• “There’s no f^&*ing way I’m doing anything to help females drag down our Army.” ??

During project definition, and through building out of the backlog, I did a few things that really helped drive the effort — especially given that I was not a leader of this group of people who defers significantly to rank.

• First, I adhered to tight programmatic strictures: Meetings never went over time, people were supposed to raise their hands before interjecting feedback… generally, we conducted the project with as much regularity as possible. Harkening to Hanah Arendt,?it’s easier to get people on board with tasks that seem banal.
• Second, I ensured that we left time at the end of each meeting for Q&A/venting. A release valve was essential for this team as they were engaging in an effort that they fundamentally disagree with. To keep the ship moving, I wanted to ensure that each team member had plenty of chances to express grievances — just get it off their chest — so we could move on.
• Third, and most importantly, I ensured that all tasks were broken down into a level of granularity such that we could reasonably tackle them. When building out our backlog, I broke apart high difficulty tasks into smaller medium difficulty tasks, knowing that, given institutional resistance, high difficulty tasks have the potential to create logjams.

Even though I’d set a good foundation for driving project success, the going was tough. People wouldn’t show up to working groups and brainstorms. People would rudely interject themselves and try to talk over me and other participants. Team members would act like their computers weren’t working, and therefore couldn’t complete their designated tasks (keep in mind these are colonels and?top-level SES personnel — “my computer doesn’t work” is an absurd excuse for this level of leader). Being the lowest ranking person in the room was crappy because they could push me around, but also freeing in that I could feign ignorance and generally step on people’s toes to get through tough problems. On more than a few occasions I ended meetings early because people were shouting at each other. Good cop mechanisms worked nicely too — I brought coffee and donuts for the group a couple of times… given that I made way less money than the other team members, they felt bad for me, and were embarrassed they hadn’t thought of it first (which meant I had the upper hand from minute 1).

We, miraculously, finished the SOP revision on time (6 months from flash to bang) to include gaining sign-off from the 2-star level. I was able to facilitate 100% approval of the final SOP among the whole project team (a reversal of approval — we started with 100% disapproving of the initiative in principle). Most importantly, I learned how to project leadership onto a team that outranked/out positioned me to create an awesome, equity-enhancing product.

Merging Competing Ideas

I once led a project that was off the rails from the minute it began. It was a small-scale, low-budget effort. I was equal or lower rank than the rest of the team. The project was meant to feed into lots of other company projects due to its wide scope, and therefore everyone on the project team — and in the company — had their own idea for where the project needed to go.

Indications that I didn’t have a handle on the project included:

• No one answered my questions in chats or channel posts.
• There were at least two direct chat groups that I wasn’t part of that involved significant conversation about technical direction.
• Team members would show up to my meetings ready to fight: From the first minute, people were talking over each other and suggesting ideas, and throwing haymakers. (Because I wasn’t part of lots of the internal conversations they were having in private chats, it took me a while to understand why everyone was so mad at each other)

Bottom line — people at all levels had opinions, and no one could agree. But they were embarrassed about their inability to agree, so they lurked around in the shadows with their communication so no one could pin the tail on them.

A few things that made the alignment of viewpoints difficult: 1) The customer was open to us just creating something innovative and cool and had very few suggestions for the final deliverable; 2) Our statement of work was somewhat broad (which is common for some small-scale projects that are meant to allow for an agile workflow with minimal constraints).

Generally, I like to get project definition (risks, external requirements, project plan, preliminary concept design, and internal kickoff meeting with the project team) knocked out in the first two weeks, no matter project length, but especially for a short project. We’d exceeded our timebox for planning already and really needed to move into the execution phase.?

I kept throwing planning huddles on the calendar to talk through the remaining project definition components that hadn’t yet been decided, but it seemed that every time we met, the team was even more unaligned. I found it difficult to get feedback on what people expected, where we needed to go, or how to offer clarity to our trajectory.

I decided to go back to the drawing board. Square 1. Pull people out of private chat rooms and encourage them to face each other and talk through expectations. I created two meetings — both of which were standardized across all projects after this iteration, which proved their importance — that would maximize communication and planning efficiency.

• Top-Level Sync. Get all the leadership in a room. Let them talk their piece — specifically: Where they envision the project going; What they want to see the project produce; What their hangups are. At the end of the meeting project leaders have a solid understanding of what the company leadership wants and how to ensure that their needs are considered and prioritized in rank order. Air out the results of the meeting in clear language, and get a formal signoff that all the leaders are cool with the alignment across departments. (Use a Confluence page and show signoff via checkboxes. You can even get formal and use Adobe Sign.)
• Project Team Sync. Once the leadership team is aligned, build a project plan and air it out with the project team. At the same time, gather knowledge on where exactly the project will go in terms of trajectory. What specifically are we developing from scratch? What are we cleaning up/building off of? Get feedback from everyone and make sure their needs are heard and documented. Ultimately, the project lead will be the final say on the direction. However, make sure that the project team has a chance to say what they want. The results of this meeting feed directly into the other project definition meetings.

Even though I lost a month in spooling, we eventually pushed through these two meetings… then we were on fire ??. All the guesswork was pulled out as people were forced to talk about their issues in front of each other. I facilitated venues to air out everyone’s feelings, recorded the results, and prioritized the feedback. We could then build a solid plan and produce a cool product.

We formalized these two meetings into the project planning of all following projects. This instance shined a light on the fact that all projects needed initial leveling and alignment between leadership and the project team — especially the small projects in which we had a lot of scope latitude. This project again shows that the best way to push through a tough effort is to be strong as a PM, run hard and fast with programmatic norms and rules, and make sure everyone has the chance to speak their minds. When these three criteria are met, you’ll have a much higher chance of running an effective, change-making project.

Summary

Hope you’ve enjoyed this! Quick recap: