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Stay Heads Up, While Heads Down (Dear, New Ops Leader | Part 4)
The art of using context to focus on what matters to the business
(Hello, new Ops Leader! I’m back with Part 4 of an ongoing series dedicated to you :) In it, I share things I wish someone would have told me when I was starting out. This week I also aim to cover some recent reader questions, you know who you are, I hope this is useful!)
This part is all about staying in tune with what really matters in that company you’re helping to build.
Let’s remind ourselves of something: you’re in this role because you’re great at solving problems, and we all know that you don’t half-ass nothin’. But when you go “all in”, you might (ok, you will) lose the forest for the trees.
It’s easy to understand why — while everyone is heads-down on that new feature, or closing that big customer, you see opportunities to resolve issues and remove bottlenecks that surround them.
This means you naturally start to focus on things that fall outside of what can be thought of as the “core business” — things that are:
Really deep in the weeds – like quickly resetting your compensation framework globally.
The risk: you’ll be dissecting the bark on the tree, and will lose your view of the forest.
Really meta – like helping teams work smarter across geographies.
The risk: you’ll be contrasting and distilling themes across “beings” in the forest, forgetting that they are trees.
Really peripheral – like evaluating new vendors for that thing that costs you a ton of money every year.
The risk: you’ll closely follow a trail, only to find yourself outside of the forest completely.
The best Ops leaders learn to balance their hyper-focus (heads down), with some perspective (heads up).
This balance helps them effectively filter signal from noise, make wise decisions (notably, on their Definition of Done), and roll-out the right things in ways that garner adoption.
Let’s break down how to effectively do that… AKA:
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Stay Heads Up, While Heads Down
Be a humble truth seeker - know the business, and the reality of how the team is performing.
Know thy context - keep your finger on the pulse of market dynamics, industry trends, and what your frenemies are up to.
Stay grounded - know employee sentiment, and be led by first principles.
Without these things, you’ll be off-balance and risk becoming out of touch.
1. Be a humble truth-seeker
It's easy for your view on the business to be developed by proxy - i.e. things are going well (or terribly) if the CEO / CPO / whoever, tells you they are.
I’m here to encourage you to develop your own view.
A humble truth-seeker hones in on the measures that matter most (using acumen and strategic context) and really watches them. If things look awry, they engage curiously - asking questions for the good of the group, in order to get to the truth of what's not working and why.
Your truth seeking will depend on your stage. If your team is pre-product/market fit, make it your business to know the guiding thesis of what you’re building and how your team is viewing north star metrics. If you’re in “scale” mode, know how things are going across your funnel and be fluent on the rationale for your roadmap.
How I’ve done this before:
I keep saying this, and will repeat it again: build strong peer relationships. The views of a diverse set of peers will be one helpful input for you.
You’ll also want to regularly attend and engage in product reviews and finance rhythms. Discussions covering progress vs expectations are great place to learn, contribute, and stay close to what’s happening.
Pro Tip: don’t forget that, regardless of what you’re focused on at the moment, your primary focus is always on helping the company reach its potential. Wear the hat of someone with a shared mandate in these meetings. Whenever possible, offer solutions to bottlenecks that are within your sphere of influence. This will ensure you’re attending as a true partner at the table vs a critic or spectator.
2. Know thy context
Start-up land forces you into a perpetual state of survival, obsessing over the problems looming largest, before pivoting and tackling the next most urgent thing. For Ops leaders, the "problem stack" tends to be "internal" — meaning the de-bugging you do serves the inner-workings of the organization versus the market.
It’s really important, though, to remember that you’re designing and building systems within an ever-evolving organism, in an ever-evolving industry. Context matters.
When you find yourself endlessly doom-scrolling your emails or Slack, consider that you might be operating in an echo chamber of your own company.
To remedy this, create space for “heads up” moments & compare notes with others.
How I’ve done this before:
Wednesday and Sunday reading: Have short blocks in your week for reading up on what’s happening in your market / industry. Some like to ingest from Twitter multiple times a day — I find concentrated sprints twice a week much more manageable.
Friday calls: I hold time every other Friday for calls with other operators in similar roles at other companies and investors / advisors. These are informal opportunities to compare notes, brainstorm, you name it. I get a TON of mileage here on the state of the hiring market (something that is typically hard to gauge from the confines of your home office).
Syncs with market-facing team members: when possible, I like to set up semi-regular and totally informal syncs with team members with a great pulse on the market. Super plugged-in BD managers, for example, are a great connection point to customer / market context.
3. Stay grounded
Lots has already been written about how easy it is for a leader to get out of touch with the ground-truth in a company.
It’s really important for an Ops leader, specifically, to have a sense of team sentiment. This helps you to “read a room” more accurately and know how to navigate complex issues.
There are lots of ways to do this poorly — like the time I worked for a leader who did a lot of "rah rah culture stuff" right after a layoff; or the time I kicked off a cross-functional strategy project in the midst of a busy product sprint.
It’s actually laughable how easy it becomes to get so wrapped up in your stuff, your timeline, your tool that you forget there’s this whole company out there, doing things.
So, before you work yourself into a tizzy — try these things:
When rolling out a new idea, start with principles and remain flexible on implementation details (especially tools) — allow the teams closest to the problem to have the loudest voice there. As you start to encounter bumps in the road (inevitable with anything new), stay close to key team members for the ground truth, and focus on aligning the team around key principles.
Build an informal board of employee-advisors. Compose your “board” with a diverse and mature group of truth-tellers who will give you the unfiltered facts. (note: not gossip — but truth on how your ideas are being received, how teams are feeling, and why).
If you’re not in an office, randomize your encounters. Consistently schedule 1:1s with various members of other teams to broaden your vantage points on key company issues (here’s a Slack tool I’ve used for this in the past).
Your unrelenting focus is your strong suit — make toggling that focus between the weeds and the forest your superpower.
Thank you for reading. Until next time!
Find the rest of Dear, New Ops Leader here:
Part 1: Dear, New Ops Leader...
Part 2: Pick Your Boulders
Part 3: Don't Lick the Cookie
Part 5: Invest in Yourself
I truly do this for the DM’s. If anything above was helpful to you, or you have a question, or a joke — I’d love to hear from you. Just reply!
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