The Silent Killer of Your Operating Practice: Fear
A must-read for any new Ops leader (guest post for First Round Review)
*An interlude in the Dear New Ops Leader programming, to share a piece I wrote for First Round Review on fear . I’m excited to share this with you during the New Ops Leader series, as it folds in nicely alongside the lessons & learnings I wish I knew when I was starting out. I hope you enjoy.*
Big thank you to the incredible Yoko Li for this original cartoon, which captures the spirit of this post perfectly :)
There’s a distinct feeling I’ve had in leadership meetings – a pounding in my chest – whether it’s a large in-person meeting, or staring at a dozen faces on a Zoom screen. It typically arises not as a response to what is being shared in the meeting, but from what I’m not saying.
Because, instead of taking the leap and bringing up that concern about our launch plan (and risk upsetting Jon, who has been working nights and weekends on this), or surfacing that unaddressed risk in our financial model (and rabbit-holing the discussion for 20 minutes), I decide to just not go there. Maybe the issue will resolve itself naturally.
It’s a feeling that I now can identify as fear – and looking around, I can’t help but wonder who else in the room might be feeling the same way.
The problem is, going there is exactly what makes these operating exercises valuable.
Rather than focusing on day-to-day execution, something most startups excel at, strong operating practices (like goal-setting, planning and business reviews) require something different. Teams must use a wider lens (much wider than the one they look through every day), deeply consider future states (possibly distinct from the one they are currently chasing), and agree on a concrete course forward (one rife with unknown-unknowns).
This requires that teams put all of their cards on the table, and enter a space of reflection versus reaction. That they express the underlying concern that is preventing them from buying in completely. That they sidestep fear, for even just a moment, in order to envision what could be true.
Slowing down to go fast
Now, before you start grumbling about how you don’t have time for this – you’re running a startup! You need your teams to just “move fast, break things!” (or insert your favorite mantra here) – please, hear me out.
Behind these pithy slogans tends to be a dangerous assumption that everyone is on the same page – that they know what to move with urgency towards, and what can break; that they know how the company is performing, and that they are interpreting and processing the events of the market in a similar fashion.
But I’ve found that in most teams, especially those operating in complex environments while rapidly shipping, this is simply not the case.
And this problem compounds as teams start to scale. In fact, I regularly observe teams grow from 10 to 25 and completely lose the thread on what they are there to achieve. During times of change, execution is no longer about staying heads-down and building – instead, it becomes about:
Staying grounded on a thesis and figuring out how to get smarter over time as a team.
Saying “no” to countless distractions and focusing on making the right few bets.
Bringing in and properly utilizing new skill sets to expand the team's capabilities over time.
The above requires intentionality and real alignment on what you are going after, and what really matters along the way. To achieve this, as a leader, you need to acknowledge and help mitigate fear.
In this piece, I’ll cover a few common fears that plague all of us in the workplace, particularly around goal-setting, and I’d like to offer a few tactics for keeping them at bay.
In most organizations, goal-setting tends to be a time when hopes and fears are translated onto a page.
These lessons were born from patterns that I started to recognize during nearly a decade leading dozens of leadership teams at PayPal, and now as a COO advisor to early-stage startups.
Whether you’re considering H2 planning, or just navigating the difficult terrain of today’s market, I hope you pick up some practices that you can apply to help keep your teams aligned, grounded, and operating with less fear.
5 COMMON FEARS (AND HOW TO KEEP THEM AT BAY)
So, let’s dig right in and go through a few scenarios that tend to undermine the very collaboration needed to get the most out of your operating practice (along with some fictional archetypes to help bring each to life).
THE FEAR OF FAILURE
Julia is a seasoned SVP who refuses to set an aggressive target for her team. She’s learned from previous roles that if she sets a target and misses, it’s likely that her budget will be cut next year. So instead of buying in and going big, Julia goes for a modest target that she knows her team will over-perform against.
Tyra is gun-shy to agree to a target, and she’s gone silent on the email thread. Why? Because the last time she went “big” and failed, she felt like she lost vital ground with her peers and her CEO. The culture claimed to believe in “fail fast” – until Tyra did.
Golden Rule #1: Set the tone.
As a startup executive, you are leading everyone through a grand expedition — what you're attempting has never been done before, and it's going to require that you utilize every ounce of skill and resources that you and your team have at their disposal.
But at a fast-growing company, it's very easy to become hyper-focused on your piece of the puzzle, rather than how the constellation of pieces fit together. This is why team-building exercises, like ropes courses and escape rooms, are a favorite on leadership team offsite agendas: to remind you that you’ll accomplish much more together, versus going about it alone.
The act of “team-ing” is a muscle – and if not exercised, it will atrophy.
So, at the start of a goal-setting exercise, or better yet, throughout the quarter – remind your leadership team that they are, in fact, one team. Reinforce the expectation that everyone works together to reach the summit. Also, state the rules of the game. Some tactical tips include:
✨ Subscriber Question ✨
I’d love to know what you subscribe to or read on the Wednesday and Sunday reading breaks you mentioned. The outside in awareness is something that I’m working on getting stronger at this year so any suggestions would be very welcomed.
— Amazing, Incredible Subscriber (in response to Stay Heads Up, While Heads Down)
Dear Reader,
It’s daunting trying to prioritize between the endless resources you can theoretically incorporate into your weekly routine, and I will confess, I switch mine up from time to time.
To shed some light on one way to approach things, here’s a bit more about what I do:
Wednesdays – “happenings”, things that are time-sensitive in nature. Information I might want to know mid-week, in case I want to show up smart somewhere…
Twitter – I do a Twitter sprint first-thing in the AM (my feed is curated around web3, AI and any industries specific to my portco / clients — pick your poison!)
Morning Brew (sent daily!)
The Information – they tend to have helpful exclusives
Linkedin headlines – I peruse the Top News
Bonus: Fridays – roll-ups (this is an extra, when time allows)
Find a roll-up specific to your industry
Let someone else curate the most important news for you!
(Hint: I’m currently testing some customized news roll-up platforms, stay tuned for my top pick)
Saturdays – for more blue-sky, interesting stuff. Less time-sensitive information to consume, the goal is learning / connecting dots.
For commutes – learn things from smart people:
In-Depth (First Round Review)
There are endless ways to design your personal information-absorption strategy. Carve out dedicated, recurring, time (a crucial step) and pick a few resources that feel engaging and easy to read. Sample different things and don’t try to “fill your funnel” all at once—get in the groove and build up. Hope this helps!
<3 Amanda
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