LOTR: Boromir's search for a better-fit fellowship
"Maybe Twilio will let me take the ring to save Gondor.."
TL;DR: Boromir worked with a group he didn’t get along with. He wanted to get a sense for how to find another organization that aligns with his values and how he works best with people.
You’ve been together for years at this point. You thought it would last forever. When you started, everything seemed so nice: they gave and gave, so you felt compelled to give in return, even when they didn’t ask. But they did ask, and the asks kept coming. Maybe it came from a place of wonder. If you could give so much, maybe there was no limit. Maybe you could do it all.
But you couldn’t. Not because of a fault of yours, but you’re human. You do have limits. And you need more than lip service.
Over time, it became clear: you weren’t going to get your needs met the way you needed. And you tried talking to them, you tried having a genuine conversation about what you need. But they told you it’s just crunch time, and we all gotta put in a little more right now. Budgets are tight, we’re all tightening our belts and feeling the squeeze a bit, but really, truly it’ll just be for peak season.
But peak season came and went, and it was more of the same. So you decided it was time you went, too.
A client I worked closely with over the course of a few months, Boromir, was in this position. What seemed like a great relationship between him and his place of work turned out to be not so great: when they saw he was willing to go above and beyond, they asked for more and more of him. But without more care taken to make members of the organization like Boromir feel engaged and considered, he saw it wasn’t going to work out.
Boromir had reached out to me when he felt this dissatisfaction, a growing sense that his ideas were being sidelined, a distance from his peers and management. All this culminated in him feeling dread when he worked: if the work he was doing wasn’t rewarding, and the group he was working with didn’t make him feel valued, where was this going? Outsized compensation could have offset these feelings for a time, but truly that sense of social cohesion and collaborative energy is so key to a feeling of belonging, that without them, Boromir was bound to leave before long.
First meeting
In our intro meeting, we started by getting to know each other. I learned that he was the youngest child of two, as I was, and that he also looked up to his older sister. He’d found a lot of purpose in helping people, but could often get frustrated by the problems that prevented that help. Although he considered himself a realist, it often meant that he was all too aware of the challenges that he faced and had that feeling of “if only people saw it my way..”.
Then I asked Boromir to walk me through why he sought me out; what was it that he wanted help changing, fixing, or accomplishing?
We talked about the role he had at the time, and the journey that brought him to that point. As noted above, he shared with me the sense that he couldn’t convince others on his team that suggestions he made were worthwhile. When all was said and done, Boromir felt like the only option he had left was to find another team. He made it clear that what he wanted was to find a place of work that felt like he fit.
This took up the full time, so we scheduled a follow-up meeting to get to the root of what Boromir needed and how we could get him there.
Second meeting
Discovery
With an hour on the books, Boromir and I dug in. Although he knew he wanted a new place of work, our time was best spent equipping him with the skills to find and evaluate roles and organizations on his own.
We started by talking through what Boromir needed from a logistical standpoint and what Boromir valued in a role. Put differently, these are the policies and cultural norms of an organization.
As an example:
A policy would be “Unlimited Paid Time Off”
A cultural norm would be “Most people take about a week off a year”
These are not always two-sided; you can have an official policy untempered by a cultural norm, or a cultural norm followed until a policy is codified. I’ll talk more about these another time, but suffice it to say that for any issue close to your heart, it’s important to know both sides when considering a job offer.
Here’s a short list from my discussion with Boromir:
“I need a manager and peers that encourage process improvements and new ideas”
“I want a workplace that has a social element, so meetings are productive, but where a casual conversation is considered socially productive”
“I need to have the One Ring so I can save Gondor”
I’ll admit, I can’t say he and I were aligned on bullet 3.
Skills
Once we settled on the requirements Boromir had for any potential employer, he was already feeling a bit better. He now knew what he wanted. But he’d gone through interviews before and even at his current job, he’d thought this would be a great fit. What happened? What was he missing?
I shared with Boromir some of my experiences working with a number of different teams and my time as a hiring manager. Although you’ll never be able to know for absolutely certain (after all, teams change, you change, your needs change), there are two main things to look at through the hiring process, regardless of the role:
The content
The structure
This applies to every step: the job posting, the recruiter screen, the call with the hiring manager, the interview prep, the interview, the offer. Even the presence or absence of any one of these is indicative of what the people you’d be working with value and how they approach work.
How, then, do we go about finding these bits of information we now know are important? For structure, that’s easy: whether it’s laid out for you explicitly or not, you go through the process and can say “they did / did not include a conversation with a member of the team as part of the interview”.
For content, here’s the trick: you can ask.
It’s still important to be cognizant of how you ask, as it does inform how you are perceived; but I’ve worked with folks that were afraid to be straightforward in their conversations with potential employers. They didn’t want to inadvertently reveal some mythical flaw in themselves by asking the wrong thing.
Crucially though, what you are actually revealing is that you are experienced and are aware of what you want out of a workplace. That is an asset, not a flaw.
Based on the list of what Boromir needs from his new workplace, I suggested keeping an eye out for these flags as a starting point:
Ask the manager (or a team member) how they prioritize and implement improvements to team processes. Compare it against how it worked at your company - do they emphasize crowdsourcing and group discussion? Do they silo it off to one owner? What phrasing do they use to describe the process? Is it grounded in an understanding that systems play a part in performance, or do they emphasize individual responsibility?
Do they include a “culture fit” portion to the interview? Do they let you meet other members of the team? Even the presence or omission of this section is indicative of what they prioritize for their team.
Is it not better to destroy the One Ring, such that none might fall to the temptations of its power?
Conclusion
And so, with those skills, Boromir set off in search of a new organization that aligned better with his needs and values. He sought understanding and opportunity. And power.
Haven’t heard from the guy in a while. Hope he’s doing well.