User Guide, Shawn Christian COO, Main Street

My style:
Ask for forgiveness later rather than asking for permission first — i’m obsessed with experimentation and how we can leverage existing infrastructure to cobble together hacks that 10x the business

Avoid saying out-loud what is implied. this also applies to ‘busy’ work — be able to dictate the value you’re creating before starting any endeavor. work for the sake of work is not work — work is a means to an end, so let's get to that end as soon as we can!

I move incredibly fast and typically don’t linger on something unless it will have an outsized impact on the business

Worry about the impact first, and how to scale it second

I learn best through self discovery and autonomy, which is also reflected in my leadership style — i need you to let me know if you aren’t comfortable with ambiguity


Communication
Hierarchy of communication (most→ least urgent): call→text→slack→email
Preferred: slack

I like fast turnaround and acknowledgements on written comms — e.g., i love ‘on it’

If i suggest a discussion, i will find time. don't say “let's discuss” without a follow-up of when we’ll discuss

I don’t expect you to respond to everything in real-time, but i do expect you to close the loop on everything we open. if it’s on my plate, i will do the same. i expect you to take full responsibility for and create transparency around all things under your purview. I get frustrated when i have to ask about something twice.

Frameworks and context are critical to sharing your work. i am always interested in the reason why you believe what you believe.


Reporting
Create a regular, systematic, and clearly framed written process by which you share your progress against plan. collaborate with me on this. make it as quantitative as possible:
1. Make the line between this, your okrs, and the company okrs clean
2.
Share this with me no less frequently than once a weekalways share your model


1:1s
With the advent of productivity tools, I realize that communication is typically quite fluid so i’m comfortable meeting ad-hoc but will rely on dedicated 1:1 time if we need to level set

I will rely on you to set a 1:1 cadence to whatever fits your work style the best. i’ve consistently operated under the motto of ad-hoc mtgs > recurring 1:1s

In regards to the framework of 1:1s, see below:
1. Maintain a running google doc that we collaborate on
2. This is mostly your time and your agenda
3. I like using 1:1s to check-in on how you’re doing, what you need from me, personnel issues, broad strategy questions that we can seed/discuss


First 3 months:
I lead with trust, and will lean heavily on you to bring me up to speed. apologies up front for the amount of questions and un-based assumptions i’ll have.

I’m well versed in a low-skill marketplace; so there will be a learning curve with this supply base for me


Feedback from me to you
I commit to providing direct feedback.

The #1 way to succeed is to make measurable business impact that’s in-line with our mission and the company okrs. i will measure your success by the business impact you make. if you’re not sure how your role or work output contributes to business impact and/or if it’s not clear how to measure it, do not proceed until we are aligned.

I’m a proponent of celebrating wins / learnings every day!

On the flipside, i am extremely passionate about our mission and may come off as combative because i will disagree and agree with you forcefully. just in case it rubs you the wrong way (which inevitably will happen), it will be because: 
1. I’m so excited by the substance of our disagreement

2. You did something that i felt was poorly constructed, incomplete, inadequate, or otherwise didn’t meet my expectations. we all have triggers that cause us to look unfavorably on our colleagues and these are mine:
(a). You’re giving up too soon and aren’t showing enough grit. i love when you demonstrate creativity, resilience, and tenacity when confronting adversity
(b). You aren’t showing enough rigor. i love when you intensely evaluate the pertinent evidence, integrate that information from a wide range of sources, and apply sound judgment to make solid, smart decisions rapidly
(c). You aren’t connecting your work to impact on company okrs — see the forest for the trees
(d). You are shirking responsibility and not acting like an owner. be an agent for the change you want to make at this company and show fearlessness. it’s ok to fail and take calculated risks. speak your mind when something is broken and pair it with solutions.
(e). You aren’t engaging in your own learning and teaching. a thread that binds us together is curiosity — about our industry, business, customers, function, and perhaps most importantly, about ourselves
(f). You aren’t showing enough leadership or investment in engaging your team. internalize our company mission and connect it to your team’s, communicate and evangelize it often, always make recruiting exceptional talent your top priority, build morale, career-ladder your team, deliver clear feedback, design your org to scale for 12-18 months, attack conflict swiftly, and be proactive with resolution
(g). If you do one of the above that causes me to react negatively, i’ll share my observation of your action, the effect it had on me, ask for your opinion, and then clarify the feedback. i’ll do this either immediately if nobody else is there, after the meeting, or during our 1:1

I’m frustrated with you because you have done parts of (ii) multiple times


Feedback from you to me
Commit to providing me direct feedback when i’m blocking your or the company’s success

I am flawed. I tend to expedite process. i can be bursty. i’m quick to settle on the solution and knowingly ignore the nuance in between. i struggle identifying with people who waste time and don’t exercise sound logic.

I respond well to feedback. i don’t like yes-men/women and after we establish a healthy trusting relationship, you will be rewarded if you give me feedback on how i can better support you and the company. our relationship will get better if you do this well.

I encourage you to be clear with me on how i can best work for you. consider writing a user guide like this for yourself as i will honor it (or tell you if/when i can’t). through our relationship, i will work to understand your style and how you’re best supported.


On Micromanagement
I am hands off until i lose trust in you. our relationship will feel more like a partnership or me supporting you than boss-manager if we’re successful at not losing trust.


Me as a resource to you
Be clear what you need from me for your success. role, comp, org change, more feedback, more context, more board interaction, etc

Be clear when you need the company’s resources. be data-driven about why you need it, gather alignment from the pertinent stakeholders, and show that you’re being cost conscious. i like justifications that include, “this is what [company we respect] does” + “this is the roi” + “this is what an experiment would cost and if it works, from there i can shut it down or scale it up” + “this is the most cost-effective solution for these reasons.” develop a nose for value and bargain-hunt.

I love to work through problems together if it’s useful to you


Professional Development
I try very hard to hire leaders that i would like to work for myself and are meaningfully better than me at the function you lead. as a result, it’s unlikely i will be a mentor to you in your role. my biggest value to you is to be a strong vocal advocate for your success, get you the resources you need to be successful, empower you to make an impact without friction, remove any blockers to your success, lead and foster collaboration amongst the leadership team to align on a strategy that maximizes our impact, and surround you with a team of peers that inspire you.

(a). I will help connect you with people at other companies that are leaders in your function
(b). I will change your role to help you change/increase your scope of responsibility/influence if you are performing and that is your goal
(c). I will create an environment where you can perform and feel fulfilled. i commit to doing all of these and expect you to hold me accountable if you don’t feel sufficiently supported.

I’m highly results-oriented and as a result, it’s not my first instinct to focus on professional development. i will do my best, but it will benefit you to clearly communicate your professional goals


Hiring/managing your team
Always lead w/ tech

Collaborate with me closely on your org structure design

Collaborate with me on your new hires

Share with me your team management system—how you communicate the vision, set goals, create alignment, foster high engagement, and cultural nuances/recruiting practices/performance review processes that are unique to your team

I’ll push you to push out poor performers and get frustrated when we take too long to act. be fair with terminations— take responsibility that you (or your predecessor) made a mistake hiring them, and don’t surprise your employees that they are being let go

Recognize and support your top performers lavishly. help me help you recognize your top performers

Don’t let your cultureamp results be a surprise

Don’t surprise me with employee departures. we should know about these before they happen

Pay accordingly for talent (creativity can be useful)

Know the tech talent ecosystem and where the best talent resides — don’t rely solely on our internal recruiters to hit your hiring goals


Contribution to Strategy
Our leadership discussions are a critical time. be engaged, don’t multitask, keep up with the pace of the discussion, work to grasp the nuances, and participate actively – if you’re quiet i assume one of two things:
(1). You’re frustrated and don’t agree (ping me)
(2). You agree and don’t want to prolong the conversations (ping me)

When building product or exploring a new venture, find the quickest path to an MVP and make sure you document it so it can be easily passed and iterated on

Be proactive in identifying new opportunities that propel the business forward. it’s not enough to just wear your functional hat in strategy discussions. this is a time for you to take off your functional hat and own the overall company strategy.


Logistics
Tell me about your personal space boundaries. i will respect them

I like to have open-ended conversations after-hours.

I like having beers when thinking philosophical / discovery / innovation (someone must take notes lol)

I tend to snooze slack when i’m busy personally

I can talk anytime (24x7) if something is urgent

Take vacation whenever you see fit so long as you’re covered on your okrs

Keep your calendar current, make your calendar responses status accurate (ie- don’t accept meetings you can’t attend, say tentative if not sure)