A Guide to Working With Romeen

9 min readApr 30, 2019

Nearly two months ago, I announced my next adventure transitioning from McKinsey & Company to Metasys Technologies. The first 60 days have been jam packed — leading an organization of 75+ (and getting up to speed!) comes with a number of challenges, but after getting into the trenches over the last month, I could not be more excited for the future of the company.

Over the past few months, I have been reflecting quite a bit on what it takes to be an effective leader. It’s a pretty uncontroversial statement to say being an effective leader requires clear and transparent communication. But how do you actually effectuate this? Nuance and practice is often where this value statement becomes muddy.

I’ve seen many misunderstandings and frustrations loom in workplaces simply due to miscommunication. As an entry point to being an effective leader, I think there is clear low hanging fruit opportunity: be as clear and transparent as possible about the way you work as quickly as you can when entering a new organization.

One of the exercises I valued most from my time at McKinsey was the “team learning.” Whenever we kicked off a new project, we took the time for each individual to discuss a host of topics: personality type, aspirations, pet peeves, ideal routine, what was going on personally that was of specific importance at the time, and learning and development goals. As an operator, that dynamic shifts since you are not working with new people every 3–4 months, but the underlying principles are consistent.

The best example I have seen of taking the “team learning” principle, but putting it into the context of an operator’s world is what Claire Hughes Johnson did at Stripe with her “working guide.” I took inspiration from her and put together a “Guide to Working with Romeen.”

The intention of the guide is to give your colleagues a better sense of your personality, understand how you think, and get a feel of what interaction approaches work best for you. Most importantly, it not a mandate or set of rules — it’s a starting point for a conversation on how to best work together. I have found the guide to be most effective when discussed in 1:1s and when the conversation is bi-directional; I encouraged each member of my team to draft a similar document and share it with their immediate teams and the company at large.

My guide is structured in 4 sections and goes from strategic to tactical: (1) Personality Type, (2) Operating Principles, (3) Communication Style and (4) How I Think About Meetings.

In my experience, I have found this exercise to be significantly helpful in increasing collaboration. I hope you find it helpful as well.

*************

PERSONALITY TYPE

ENTJ (Extrovert, Intuitive, Thinking, Judging)
I am a borderline E, N, and T but a strong J. What does this practically mean?
E: I love people (and am a big people person), but I also appreciate space and time to think — this is how I get my best work done
N: I like talking about big conceptual approaches, but I appreciate a pragmatic and specific plan on how we are going to get there
T: In a vacuum, I prefer to make decisions with facts over feelings — this is of course context dependent
J: I am a big planner and love structure — if I feel like our plan or approach isn’t tight, I will openly communicate this and push us to get there

If you’re curious to see what your personality type is — check this out. Drop me a line; I’d love to know what your MBTI is!

MY OPERATING PRINCIPLES

I. We dream about mission and live by metrics

I believe deeply in the “Mission to Metrics” framework:
Mission: Our company has a singular north star that we aim to accomplish
Strategy: The tactical plan on how we will achieve our north star
Role: The specific part each of us play in the plan
Metrics: The guideposts we use to gauge how we are performing against the expectations of our role
To me, alignment is when everyone is crystal clear on our mission, strategy, the role we individually play and the metrics that will be used to measure success
In my experience, I’ve seen a direct correlation between clarity and fulfillment. I like to ask myself if I enjoy coming to work and take pride in the company I’m working for as routine pulse questions. When “Mission to Metrics” is working properly, I’ve always found my answer to those questions to be a resounding “YES!”
To maintain adherence to “Mission to Metrics,” I like to resort to data so we are operating from an informed perspective

II. The best ideas should win regardless of hierarchy

I value good ideas and love working as a team to get to the best idea; I believe ideas should win on their merit, not simply because they are from the highest ranking member of the team
I judge idea quality based on data and intuition (but as I mentioned above, I bias towards data and facts over “gut feel”)
When we are working through an idea or problem, I’ll encourage you to keep the “obligation to dissent” card in your back pocket. What does that mean? If you have a different perspective, speak up! I love healthy debate and believe an open exchange of ideas gets us to the best answer
I really appreciate clarity of thought no matter how complex a topic is. If I feel we are scattered, you will hear me bring us back together with orientation questions — (e.g. what is the problem we are trying to solve, why do we need to solve it, when do we need to solve it by, and what is the shortest path to solving the problem). If you have certain “go to” approaches to solve complex problems, fill me in on your approach. I’d love to learn from you and be cognizant of the way you think

III. Once a decision is made, let’s collectively move forward in one direction

I’m a firm believer in the Amazon principle of “Disagree and Commit.” What does that mean? Once we come up with the answer, even if you thought differently though the debate process, commit. We are one team; once we’ve made a decision, let’s put the “debate phase” behind us and move forward in one direction

IV. We are only as good as our execution

I’m not a micro-manager, but I do sweat the details. You’re thinking — how do those 2 phrases make sense together?
As long as I feel things are on track, then I’ll stay out of your hair (I’m really not interested in imposing my style on you or “putting you in a box” because I know that can feel stifling)
But if I feel things are off or I haven’t been able to fully wrap my head around the situation, I will lean in to understand the situation and make sure we are going through it in the right way
At the outset (over the next 3–6 months), I will get into the weeds and often dive in deeply. Please do not take this as me not having confidence in you; it’s anything but that. I want to make sure I can best help you and having maximum context and understanding will allow me to do that moving forward
If action items or deliverables need to shift because of new priorities or new information please let me (and any team members) know ahead of time so expectations are managed
I expect you will make a number of decisions without me; if you come to me, I’ll work to quickly understand the situation, but then I’ll likely employ a coaching style I’m familiar with — the Socratic method e.g. “What do you think we should do?” I do that not to punt on responsibility; I do it to coach you and to help you trust your judgment. If there are alternative coaching/discussion styles you prefer, let me know!

V. Think about our company like we’re a pack of cheetahs; we have speed and agility on our side

We are not a 1,000+ person company (yet!). This is an advantage, not a disadvantage
I want us to be really intentional in our prioritization of how we spend our day and what we work on since our time (especially at our scale) is super valuable
The last line of defense is each one of us — I will always lean in to support, but I expect you to carry your weight. We are all in this together

VI. Push each other to be your best self

Your personal and professional life is important to me and I want to make sure I am doing everything I can to support you. We likely won’t talk (in depth) daily; please make sure to let me know how I can help you
Over the next few weeks, we’ll do a deep dive session to discuss a variety of topics — your background, your ambitions, what you like about your job, what you believe you’re good at, what you would like to do more of. This will help me get to know you better and understand where you are in terms of your personal development, interests and long term ambitions.
Let’s maintain this cadence moving forward and continue to check in. If you feel like we haven’t spent 1:1 time together in a while, please ping me and set up time on my calendar on a Friday afternoon and let’s grab coffee/connect over video conference. I would love to stay plugged in to things that are at the top of your mind and find ways to be helpful.

VII. Feedback and learning are a two way street

I’m a big fan of constructive and consistent feedback — I like to give it and I like to receive it
I’m a strong believer in upward feedback so if you feel there’s something I can do better, please let me know
Let’s learn together — help me learn and I’ll help you learn. It’s not my job to disrupt the already great work you are doing, but it is my job to find ways to help you to continue to accelerate
Fill me in on your learning, best practices and how you think about our company. I want to hear your perspective on what we can do better

VIII. Let’s have fun

The journey matters just as much as the the end result
I’m always up for a good joke — I’m terrible at delivering them, but I’m always in the market to hear them :)

COMMUNICATION

Style

Overall, I like more communication rather than less
I’m a visual person — I like to see things written down and how they flow together
In that vain, I like quick drafts — it doesn’t need to be perfect; bias towards putting something down on paper so we can talk about it

Email

I will always read email you send to me or I’m included on, but I won’t respond just to say I’ve read it (I don’t want to add more email to either of our plates)
If you feel I haven’t responded and I should have, don’t hesitate to resend or ping me. It’ll help me if you’re clear on when you need a response by
Please add me to emails or documents that might be helpful for me to see to understand something you are working on or something that’s going on within the team (FYI emails are welcome)
My office is always open, but please be a good judge/steward of time — I want to give you the most thoughtful response. If it’s a long topic and not time sensitive, email me and I’ll read and respond

MEETINGS

It’s my intent that we will do planning on a quarterly cadence and we will check in at a company level monthly (weekly for teams) to discuss if we are on track
I’m a strong believer of the “maker” and “manager” scheduling concept — if you feel your schedule isn’t being optimized (after reading this post), let’s talk and figure out how to fix it
For meetings to be most productive, I appreciate if documents for the session are sent out ahead of time and have a strong preference for them to be sent out sooner rather than later. I’m at my best when I’ve had time to digest the information and give proper thought
If it’s your meeting, please come prepared with an agenda, perspective on what success looks like and let me know how I can help you to achieve that success
I like to spend more time problem solving and collaborating in meetings vs. using the meeting solely for updates so let’s work together to make that happen
I appreciate being fully “present” in the meeting (e.g. limiting laptop and email activity). I’m not always perfect at this, but I commit to trying my best.
I like to default to 25 and 55 minute meetings (to leave time in between meetings); I’ve typically found this to have a positive impact on keeping everyone’s schedules on track
I like to know how everyone on the team is feeling so I will routinely do skip level meetings (e.g. meet directly with you, without your manager) to make sure you have direct access to me and information is flowing up/down