Though I’ve been in startup ops for years, I’ve often wondered how different the roles, responsibilities, and challenges differed across other startups.

To learn more, I recently surveyed 50 operators, across seed to late-stage startups, with the goal of gaining more insight into how the ops role is structured across companies, as well as what common challenges and opportunities exist.

Here’s a summary of key takeaways:

The majority of respondents (72%) came from earlier-stage startups (Series Seed through Series B). I found it fascinating that most startup operators (90%) are non-founders.

As you might expect, the most common titles all had “Operations” in them. The titles seemed to be relatively stage-agnostic (e.g. the COO or VP Ops title could be found in any stage company).

As the above chart shows, startup operators are truly responsible for a wide range of functions. While some folks may have a more specific focus (e.g. GTM or customer success function, or even supply-chain logistics), what’s undeniable is that most startup operators work “in” the business. Most common functions span business operations, finance, people ops, and legal.

Operators who had been at their company for at least a year mentioned that the scope of their role frequently changed as a result of business needs. In particular, multiple people discussed how their career growth (and the number of functions they were responsible for) either grew organically as the business grew — or in some cases, expanded to fill more gaps due to a lack of hiring.

The ops role in general can be described in a number of ways:

1. A “Head of everything” generalist for the business—someone who can kickstart new functions before there is a need for a FTE, or can fill in any gaps.

2. The “PM of the business,” who’s tasked aligning the company on KPIs and strategy and enabling the business to run smoothly.

3. An executor who can “turn vision into reality.” In many cases, an Ops person is a grounding force, especially in relationship to the CEO of the company. If the CEO is “on the business,” the Ops person is “in the business” and is translating the vision into strategic, tactical next steps.

There are so many colorful metaphors to use when describing ops — my favorite was definitely “the nerve center of the octopus” to avoid wildly thrashing arms. 🐙 😂 Otherwise… there were many transportation-related metaphors: keep the wheels on the tracks, keep the engine running smoothly, swap out plane parts while flying it, etc.

By and large, the biggest issue startup operators face is around prioritization and time management. With being stretched across so many different domains, it can be difficult to have enough minutes in the day to catch all the balls in the air. From personal experience, it’s natural to bounce between a 30K view to being nose-deep in the weeds, all within minutes.

Finally, 4 main themes emerged for why startups of all stages can use operations:

1. Operators can be trusted to get shit done, quickly! Speed is everything in a startup, and great operators help turn vision into reality.

2. Operators fill in key gaps as the company grows, pinch hitting along the way until there’s enough need to develop a FTE or team around a specific function.

3. Operators build processes and consistency across the organization, enabling others to stay aligned and move more quickly too.

4. Operators have a birds-eye view of the organization and understand how to connect the dots across orgs, people, and teams, enabling more efficiency and impact.

Call me biased, but operations are a must-have for any startup. 📈

When I was first starting out in my career, each 1:1 provoked a ton of anxiety. My managers had set the expectation that it was on me to put together an agenda each week, but I didn’t have much guidance as to what information would be helpful to cover on a regular basis, or what format to use.

With the benefit of more experience and now with a managerial lens, I see 1:1s as some of the most important meetings I have each week. They are an opportunity to:

1. Connect with each person personally and develop the relationship (and trust!) needed to sustain each other and the business.

2. Share context and align on priorities.

Welcome to Part 3 of my meeting mini-series, with practical tips on how to run better meetings. Today’s post is all about my personal approach to 1:1s.

Here’s a quick refresher on the series and what to expect:

Part 1: RESET - Structurally refreshing your meeting culture

Part 2: RUN - Tactical advice for how to run effective meetings

Part 3: DEVELOP - Tips for getting the most out of 1:1s 👈 You are here!

Recently, I’ve been thinking more about how to provide more clarity and “make the implicit explicit.” In the context of 1:1s, I realized that I had some strong, unvoiced takes on the format! However, I had never formally documented them… until now. :)

The following is the personal user guide on my approach to 1:1s that I shared with my team. As you read it, my advice would be to think through “What of this resonates? What doesn’t?,” and then create your own guide! (Here’s the Notion version, if you want a quick template to duplicate.)

Here goes:

A guide to my approach on 1:1s

Hello! If you are reading this, it’s likely because we are working closely together and have weekly touchpoints scheduled. The below is a living document of my personal philosophy on 1:1s and how we can make the most of our time together. ✨

Why have 1:1s?

I've found that the weekly touchpoint helps us stay in close flow on progress, challenges, and career discussions. Also, as a remote-first company without IRL watercooler run-ins, it's nice to have time carved out to check-in with each other on multiple dimensions, from work to life.

How often should we have 1:1s?

Folks who've worked with me for a while know that I am always looking for ways to reduce the number of standing meetings on the cal. However, our 1:1s are decidedly NOT one of those! :) I expect us to have weekly 1:1s, usually around 30 min. I will do my best to make sure that we keep the times consistent so we can both plan; however, if rescheduling is needed from either side, let's try to keep it rescheduled for the same week.

What should we discuss? Should we have an agenda?

There are various philosophies on how to spend 1:1 time. Some people prefer for it to be 100% employee-driven, and are cool with it being totally unstructured. Other people see the personal life check-in as a waste of time and would rather spend the time as a dedicated working session.

My personal take: I like to take a hybrid approach, where we spend the first few minutes checking-in with each other on how things are going (work and life), before moving on to a pre-set agenda of high-leverage topics.

I find that the personal check-in helps us both better understand any work/life context that may impact our work together and — more importantly — helps us continue to develop our relationship.

At the same time, I also strongly prefer to see an agenda of topics to discuss in our shared 1:1 doc, at least a few hours in advance. You will frequently see me add items that come to mind throughout the week, and I'd encourage you to do the same as well. Doing a little bit of prepwork will help us ensure we're tackling the most important topics every week.

Every quarter, I'd also like to align on your work goals — usually project-based plans that are typically tied to larger company goals and priorities. In addition, I want to check-in on your top 3-5 personal goals and how I might be able to support you in achieving them. Personal goals are things that you personally spend your time on (vs. the broader team), and can involve things such as "I want to further develop my skills in [x]" or include lifestyle goals like "I want to make sure I get outside for a walk every day." As you continue to develop in your career, I'd love to be an accountability buddy for making sure you get the time, space, and support you need to grow.

What to talk about, when?

In terms of what to talk about, I think our agendas can span a range of topics, including:

• Understanding what's top of mind for you

• Learning more about what you're super excited about, or conversely (and hopefully very infrequently) anything that's causing you to lose sleep

• Reviewing strategy + making decisions on next steps

• Brainstorming solutions to roadblocks or solving day-to-day challenges

• Understanding what gives you energy (and what takes it away)

• Feedback on how to improve things (whether related to a process, project, team, or the company)

• Feedback for each other

• Career development

• Anything else on your mind

In the course of our discussion, you'll likely hear me ask a lot of questions to develop a better understanding of the issue and context, as well as what potential solutions could be. And when you share something for review, I'd love your input on:

1. What level of feedback you're looking for at this point? (e.g. broad strokes, final pass, etc.)

2. What role you want me to play for a topic? (Listen, advise, fix?)

One of the things I'm working on is ensuring that we all develop our intuition for making decisions quickly. To that end, I am always up for brainstorming options together and being a sounding board for ideas (especially for hairy issues!), but would also love to hear your recommendations for what to do.

Finally, in terms of what NOT to cover live — I'm a strong believer in covering FYIs/ quick updates async so that we can spend our synchronous time together on the most high-leverage topics. Updates that are better left for async can include things such as:

• Project updates + status

• Vacation / OOO FYI

Feedback and accountability

Someone once told me that "all souls are here to grow." As a big believer in continuous growth and development, my hope is that with regular feedback, we can help each other grow! In working together, I promise that I will share regular feedback on what's going well and what's not, and also ask that you do the same for me.

In our 1:1s specifically, I'd like there to be space for us to each ask weekly, "What feedback do you have for me?"

My approach to feedback, both positive and constructive:

• Whenever possible, I try to provide feedback in real-time. (e.g. be generous with praise and, conversely, don't let things fester!)

• I try to provide specific examples as a frame of reference, as well as the perceived impact.

• I always share with a positive intent and with wanting to improve our relationship.

If you have a preferred format of receiving feedback (or triggers for how NOT to deliver feedback), please let me know so I can adjust my delivery! And I will do the same for you. (Generally speaking, I'm a huge fan of the radical candor approach.)

Last thoughts

We spend so much of our lives working, so let's make sure our time together is both fulfilling and fun! 1:1s are a cornerstone of making sure we develop the type of relationship, rapport, and trust needed to make that happen. I'm grateful for all of you. LFG! 🚀

As always, I’d love to hear your thoughts! What resonated and didn’t? What other tips have worked for you in 1:1s?

Until next time,

Julia

Several years ago, my friend was in a 20-person cross functional meeting at Facebook. It was scheduled for 30 minutes, and the meeting owner opened with, “Before we get started, I don’t think everyone knows each other. Can we go around a circle and say your name, team, and your relevance to this project.” After making it through a few intros, his manager stood up and interjected, “Are we really doing this?!,” and then briskly walked out of the room.

While extreme, the guy kinda had a point. 😂

Welcome to Part 2 of my meeting mini-series, with practical tips on how to run energizing, productive meetings from some of the most effective people I know.

Here’s a quick refresher on the series and what to expect:

Part 1: RESET - Structurally refreshing your meeting culture

Part 2: RUN - Tactical advice for how to run effective meetings  👈 You are here!

Part 3: DEVELOP - Tips for getting the most out of 1:1s

Let’s dive in!

What makes for a great meeting, anyway?

Looking at a calendar stacked with meetings, how does that make you feel?

Likely some of those meetings don’t need to happen. But for the ones that do, imagine feeling excited about every single one of them.

Reflecting on my own experiences with meetings, I think what separates good from terrible meetings is how you feel at the end of it. An effective meeting:

• 🔥 Gives you energy and makes you FIRED UP and excited for what’s next.

• 🤝 Makes you feel closer and more connected to others and your team.

• ✅ Helps you feel productive, engaged, and like you’re making great progress.

So how do we get to that end state?

It all starts with prep

🌶 Personal hot take — meetings with inadequate prep are destined to fail. Great clarity leads to great outcomes, and clarity requires prep work.

Here’s how to set the foundation for highly effective meetings:

Tip #1: Start with the basics — know your intended purpose, and set the agenda in advance

Setting a clear intention of the meeting goal and expectations for everyone is crucial. As Lauren Zion, VP of Business Operations and Analytics at Socure advised, “In general, I think the key to making meetings more productive is to be very specific about the purpose of the meeting, even if it's a brainstorm or inform type meeting.” Zion continues, “If there is a significant amount of background information needed to make a decision or have an informed discussion, I highly encourage sending pre-reads well ahead of time and including this information in the calendar invites along with a specific agenda.”

As another way to quickly indicate meeting purpose, Laura Vang, our head of product, has recently started using a prefix like [JAM] or [DECIDE] in front of meeting names. The visual distinction of those labels has been personally helpful for knowing what to expect when quickly scanning a calendar for the day.

Tip #2: If the meeting purpose isn’t clear, cancel it or ask the meeting owner for more clarity

Don’t be afraid to cancel meetings without agendas. One of Zion’s tips is “to simply cancel the meeting and replace it with a written update or ask the meeting owner for clarity” if the meeting purpose isn’t clear or the synchronous review doesn't seem completely necessary.

In the spirit of doing better at this, I recently created an email template to respond to meeting invites that don’t have an attached agenda:

Though I’ve only had to use it a few times so far, I’ve been impressed with the clarity these few questions have provided! And in other cases, these questions have prompted meetings to be canceled in favor of more async comms or further research.

Tip #3: For recurring meetings, keep the format consistent

Sarah Hinkfuss, Partner at Bain Capital Ventures, encourages keeping to a reliable format for recurring meetings. “Have a structure and stick to it. When people know what to expect, they come prepared.” What I also love about this advice is that it reduces cognitive overload in decision-making — with each meeting, people aren’t fumbling to recreate the wheel, because there’s already a set agenda in place.

Similarly, rituals can drive intended behaviors. For example, my husband has a personal meeting rule of giving people a 3 minute grace period before plowing ahead and getting started. Everyone who works with him knows about the 3 minute rule, and it encourages them to show up on time so they don’t miss out.

Tip #4: Curate your attendee list and avoid attendee bloat

The meetings I get the most energy from are the ones where all the participants are actively engaged. On the flip side, I’ve struggled in meetings where it’s clear that the content isn’t relevant to everyone in attendance and therefore people’s attention and energy wanes.

As a solve for this, Hannah Baker, VP of Operations at Magoosh, recommends being “extremely intentional about the invitee list.” She says, “Make sure that everyone critical is in the room, and that everyone in the room is critical. Attendees should be both adding value to the meeting, and getting value from it.”

“If someone only needs to listen and isn't expected to contribute, share a recording or notes instead of having them join live. Attendee "bloat" can be a real killer of meeting functionality!”

I wholeheartedly endorse this, both for my own meetings, as well as the ones I’m invited to. I have a regular practice of auditing my calendar 1-2 days in advance, reviewing the agenda and attendee list, and then confirming whether my presence (or that of others) is actually needed.

Rituals for running effective meetings

So you’ve done the prep, and the right people are there. What’s next?

Tip #5: Start with a quick check-in

In a distributed, remote-first culture, it’s very easy to hurtle from meeting to meeting and not have as much time to check-in with people. Water cooler opportunities aren’t as easy to come by, and that’s why it can be especially important to have a ritual of checking in with each other to level-set, see how everyone’s doing, and build trust within the organization.

David Clavens, startup advisor and former VP of Marketing at Aalto and Scoop recommends doing a quick, structured check-in to kick-off team meetings and help everyone get more context on their current headspace. “We started leadership meetings with a red/yellow/green that was personal and professional. For example, ‘Professionally I’m green because I’m excited about the next project, but personally I’m yellow because my kid kept me up all last night and I’m kinda tired.’” He says, “With this, you can understand the energy of people when they walk into the room, which is distinctly different from ‘Wow, Bob’s in a bad mood.’”

Tip #6: For recurring meetings, report out on prior to-do’s with “done” or “not done.”

In general, I’m a big fan of sharing status updates async. However, I recently read the book Traction, by Gino Wickman, and particularly loved his recommendation to review any action items from the last meeting and only allow for two outcomes: done or not done. Having the reporting be so binary serves two purposes:

1. It makes for a snappy, efficient update, and

2. It eliminates any excuses (“I wanted to but…,” “I’m waiting for a response…”)

This is a great first step in fostering a culture of accountability and execution.

Tip #7: Try an off-topic “parking lot” to keep meetings on track

Whomever is running the meeting should also be in charge of moderating the meeting, moving the conversation along from topic to topic, and ensuring the meeting is achieving its stated purpose.

This can be easier said than done, especially for complex topics where it’s easy to rabbit-hole into tangential topics. One idea for how to keep people on track is through “parking” off-topic ideas in a visual parking lot. Clavens had some advice here too, “At the beginning of a meeting, I’d say ‘Hey, there are going to be a lot of ideas generated today. As other topics come up, we’ll put them in a parking lot and come back to them later.” He continued, “The parking lot visual made it easy for people to feel like their ideas were valid and heard, but also didn’t derail meetings from their intended purpose.”

In a remote context, I’ve started creating a parking lot section of shared notes docs, so that it’s easy to return to topics down the road. It also gives me a head start on building future agendas.

Tip #8: End every meeting with capturing tasks and deadlines

In the last few minutes of a meeting, someone (usually the meeting owner) should summarize the outcome of the meeting, any next steps, and the owners of those actions. Better yet, a written summary should be immediately sent over Slack or email.

This is easier said than done, especially when there isn’t a lot of time between back to back meetings. If possible, ending meetings early is a gift to everyone involved, and the extra 5-10 min gives people time to wrap things up before heading to whatever’s next.

Tip #9: Ask for instant meeting feedback

Another tip from Traction is to end every meeting with asking “How effective was this meeting?,” and then having people open their hands to share their ratings at the same time. I just started trialing this tactic this week, and am loving that it provides instant shared feedback with very little effort.

Share the knowledge

Tip #10: Send out applicable meeting readouts to a broader audience

Finally, it’s important to think through if any information would be helpful for a broader audiences’ consumption. What important decisions were made? What context do people need for continued alignment and action? Who else may need to be involved in the follow-up conversation? Tasking someone to send out the meeting readout can be an extremely efficient and effective way to catch people up to speed and eliminate meeting FOMO.

The punchline here? Run your meetings with intention and purpose, and everyone will leave with more energy and clear next steps on how to move things forward.

I’m always inspired by new ways to make meetings awesome — what other meeting tips have worked for you?

Coming up next, is Part 3: DEVELOP - Tips for getting the most out of 1:1s.

Earlier this year, I found myself in a 20-person daily standup. Looking around the Zoom grid, the dynamic didn’t feel right. Engagement was minimal, energy felt low, and the content covered usually didn’t apply to all the attendees. Even though the meeting was “only” 30 minutes, the meeting cost was astronomical — in pure dollars, it would easily be close to $1,000 a day, $5,000/week, or $20,000/month. Was it worth it?

“Time is money” — make it count

I’ve been spending a lot of my time recently thinking about meetings, meeting culture, and how to run them more effectively. Starting today and over the next few weeks, I’ll be sharing a 3-part mini-series on how to have higher quality and effective meetings. Here’s what to expect:

Part 1: RESET - Structurally refreshing your meeting culture 👈 You are here!

Part 2: RUN - Tactical advice for how to run effective meetings

Part 3: DEVELOP - Tips for getting the most out of 1:1s

Let’s get into it!

🧐 How we redesigned our meeting culture

Though Abridge is a fully-remote and distributed company, we were indexing too heavily on synchronous communication to disseminate information and status. Even worse, we were spending face-to-face time catching people up on context, instead of higher value decision-making. We needed a way to encourage more asynchronous communication, and make our synchronous time more valuable. But how to begin?

Tip #1: Start with a meeting audit

To figure out what types of meetings we still found worthwhile, we took stock of our collective meeting stack and asked ourselves:

“What do current meetings try to accomplish?”

Actually taking stock of the various types of content covered helped us quickly bucket the types of issues we were regularly spending synchronous time on.

Next, we asked ourselves a simple, but powerful question:

"Could this happen async?”

After a couple iterations, we crossed out status updates and context sharing, and landed on 4 categories of meetings that still felt extremely valuable to hold face-to-face (or on Zoom):

1. 📝 Meetings to make decisions + evolve strategy

   e.g. meeting to figure out “How might we de-risk elements of our plan?” or “Does it make strategic sense to prioritize feature A over feature B?”

2. 🚀 Meetings to accelerate velocity of learning

   e.g. retrospectives, experiment analyses and next steps, weekly demo sessions to share work in flight

3. 🧠 Meetings to jam together + gather input

   e.g. brainstorming sessions

4. 🤝 Meetings to develop people, teams, and relationships

   e.g. 1:1s, feedback, team bonding / social time

In reflecting on why these meetings felt worthwhile to have synchronously, I think a large part is that they tend to be momentum- and energy-creating.

At the same time, it didn’t feel like just identifying worthwhile meeting categories was enough to reset our culture. We wanted a more structural way to force people to rethink their meetings.

Tip #2: Experiment with a variety of ways to move context-sharing and updates async

As an organization, we relied heavily on Slack as a communication tool, but did not have a practice of regularly sending out updates to keep people in the loop. With being more intentional about shifting context-sharing to async, we tried the following tactics:

1. We encouraged people to shift more communication from DMs into public channels so others can follow-along.

2. We created a #decisions channel to communicate out important decisions that the company should be aware of.

3. For each meeting, we made sure someone was tasked w/ sending out a meeting readout afterwards (nothing onerous — just the main punchline and next steps).

Things are still work in progress (especially in regards to what conversations should be in public channels vs. DMs), but we’ve heard very positive feedback from the use of the #decisions channel and with closing the loop on things with meeting readouts.

Most of what happens in Slack is written; however, we also wanted to experiment with other methods of quickly sharing context, rather than relying solely on written communication to convey ideas and thoughts. Different people have different preferences for consuming and learning content, and so we tried a few other ways to disseminate information:

1. We used Geekbot to run async standup updates in Slack. We had middling success with this — not because async standup is inherently worse, but likely because there were too many people in the channel when we tried this (and therefore the burden of keeping up with all the standup posts was very high). This is something we’d be open to continuing to experiment with again in the future, with smaller teams.

2. We encouraged people to create Loom videos to share information in cases where the visual of a screen recording could be helpful. Some people have taken to Loom more than others, but we’ve found that the most compelling use cases for this includes product or work-product walkthroughs, sharing demos of our product with others, and creating tutorials that can live in our team Notion wiki and help memorialize knowledge.

3. We experimented with sharing audio memos in Slack to quickly catch people up. Speaking is faster than typing, and voice memos have been a great tool to share feedback and reactions much faster. (This is recommended more for DMs rather than group channels).

Some of these tactics have worked better than others in terms of organizational stickiness over time. However, the practice of regular experimentation here has meant that on the whole we’ve definitely seen an improvement in terms of context being shared async. Importantly, continuing to invest in async communication (and reminding people that we want to share context async) has helped us shift our meeting time to be more focused on higher-value items (strategy, decision-making, etc.).

Tip #3: Blank slate your calendar

I’ve been at companies that send around periodic reminders for how to run effective meetings. While this can be one tactic in helping people remember meeting best practices, we wanted to shake things up more dramatically.

To accomplish this, we decided on a meeting “reset” and wiped all recurring meetings off the calendar.

While this sounds extreme, it was also an extremely effective way to get people to shift from reactively attending whatever meetings were already on the calendar to being more proactive about how to use the time. It actively encouraged people to rethink what might actually be necessary.

Once we had a more meeting-free calendar, it was easier to identify key gaps in communication and rituals. We could re-think our tactics for better communication, and — where it made sense — re-introduce a meeting (with a more laser targeted agenda, set of participants, and goals).

Tip #4: Set recurring meetings to expire

Recurring meetings can lose steam over time. For example, someone may have initially thrown regular time on cals to kickstart a project, but then the meeting lost value over time as things became more established, the team composition changed, or for other reasons.

A structural way to defend against this is to set an expiration date on recurring meetings (a good starting point is 4-6 weeks). The meeting automatically disappearing from calendars is a good nudge for folks to reconvene and question whether or not the meeting is still serving its intended purpose.

In one case I observed, the meeting expiring led to some frantic “What happened to this meeting?” and “How will we coordinate the work?” messages being sent. It was clear that some folks felt anxious that this meeting had inexplicably disappeared from their cals. If that feeling occurs, it’s a clear signal that the meeting is still valuable!

Of course, there are less drastic ways of doing this… like setting a reminder for 6 weeks out to “Reassess meeting value.” However, I think the potential thrash from a an expired meeting is more likely to galvanize regular introspection and change.

Note: 1:1s are the one meeting I do not recommend expiring — regularly hosted 1:1s have been shown to boost engagement and trust!

Tip #5: Cluster team meetings to protect maker time

One of the most painful types of meeting schedules is when you have a meeting, followed by 30 min of free time, followed by another meeting, followed by another short break. The 30 minute breaks are often not enough time to get a significant task done, and context switching is inefficient and painful — especially when certain functions like engineering and design require blocks of deep thought.

When thinking through meeting cadence holistically, it can be helpful to think through clustering team meetings during a certain block of time so that large swaths of the day are preserved for maker time. (If you haven’t read Paul Graham’s iconic Maker’s Schedule, Manager’s Schedule before, it’s definitely worth a read). It’s also worth attempting to jenga your calendar to try to stack meetings into a more contiguous block.

At Abridge, we’ve been very intentional about scheduling team meetings in the mornings, leaving ample chunks of time in the afternoon for maker time. Anecdotally, I’ve heard from many people in the company that they have a strong preference for segmenting the calendar in this way and absolutely love having afternoons free.

In terms of other ways to think about designated maker time, I know that some companies will also designate meeting-free days (e.g. “meeting-free Wednesday”), and I am interested in giving this a try sometime soon.

Tip #6: Don’t be afraid to cancel meetings

My husband recently joked, “The most efficient meeting is a canceled one.” People rarely complain about getting time back, so sometimes it makes sense to just cancel a meeting if there isn’t anything pressing on the agenda to discuss.

As a close corollary, for every meeting on your calendar, it’s helpful to ask yourself:

“Do I need to be in this meeting?”

Speed is everything in startups, and in many cases, it can make sense divide and conquer among participants. Before you join a meeting, running this quick litmus test on yourself and others can help everyone free up time and go faster.

⚔️ Defending against calendar bloat

It’s easy to stack meetings without much thought, and the meeting accumulation over time can start to feel heavy. People can feel very tied to existing meetings (change can be uncomfortable!), but when things start to look too crazy, I recommend just ripping the bandaid off and making some radical changes to reset the norms.

However, just resetting isn’t enough — to maintain a culture of sharing info async + having effective meetings, it’s also helpful to have champions across the organization who can remind people of best practices from time to time. These are people who will ask, “Who can summarize this in #decisions?,” or proactively remind people “No need to attend — we’ll send the recap later!)”

For making habits stick, it’s even better if there are structural habits to make the cognitive load of meeting running SUPER easy — (e.g. baking in meeting norms into a new employee onboarding session, or setting up agenda templates for new meeting invites).

Speaking of recaps, here’s the quick summary of the litmus tests and tips I’ve used for periodic meeting maintenance:

• Run a calendar audit to understand what topics your recurring meetings currently cover. Next, ask yourself: “Can this be done async?”

• Push as much communication async as possible, and experiment with different modes of communication to make it happen.

• Nuke your calendar from time to time and remove all recurring meetings to encourage people to really think through whether they need the meeting.

• Don’t be afraid to cancel meetings that have outlived their worth. Better yet, set recurring meetings to expire after a certain number of weeks (a systematic way to force you to rethink whether or not the meeting is still needed).

• Be intentional about preserving maker time. If meetings are necessary, try to cluster them in one time block.

• It’s ok to RSVP “no.” Ask yourself: “Do I need to be in this meeting?”

As always, I’d love to hear your tips and spicy takes on meeting management. What’s been effective for you?

And if you enjoyed this content, stay tuned for Part 2: RUN - Tactical advice for how to run effective meetings!

Happy Meeting!

A big thank you to Steve Magoun, VP of Engineering at Abridge, for sharing thoughts on this topic and draft!

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Q: How do you position your value as a generalist [and get a job]?

In between startups, I briefly flirted with the idea of going back to a more established tech company. The problem was, after time away from the big tech world, I had no idea what type of role to interview for. I had done everything from high level strategy to user research, product management, people ops, marketing, web development, light coding, customer support, and more — and yet, it didn’t feel like my skillset neatly fit into any well-defined job ladder. “Jack of all trades, master of none”... right?

At the same time, I had developed a real skill-set — the ability to quickly stand up new systems and functions in an environment of extreme ambiguity. As a relentless doer, my strengths were in problem-solving, connecting dots and ultimately moving projects forward.

After all was said and done, I ended up at another early stage startup whose mission deeply resonated with me. My pitch? To be the person who can fearlessly navigate the chaos and continuously make things happen, in service of the business. (Scroll to the bottom for the exact email pitch I used to land my role as an operator at Abridge.)

Making the pitch

Based on some conversations with other operators, here are some tips to help pitch the value of bringing in an ops person at a startup:

1. Start with understanding the current challenges of the company.

My first job out of college was in ad sales. While it wasn’t the long-term job for me, it introduced me to the concept of solution selling — approaching a situation with empathy to better understand a company’s current pain points and needs (and therefore better position yourself and the role). Some questions to think through:

• What stage is the company currently in? This is helpful context for figuring out the types of challenges a company may be currently facing, as well as how built-out various functions may be.

• What does success in a year look like? How about in 5? Beyond helping you understand whether you are bought into the vision of the company, asking more about success helps you understand where the company’s going and may hint at what opportunities lie ahead.

• What are some current or upcoming challenges the company may face? For example, what types of things are falling through the cracks? Where is the slowness in the business? Pay special attention to this section because in theory, you’d be hired to help sort out some of these issues.

• Who’s at the company today? What types of roles already exist at the company? What departments or functions? Importantly — what types of roles are missing? Could you plausibly fill in the gaps?

2. Think through your unique set of skills and experiences and how they may fit into the current organization.

This is the fun part — where you take inventory of your lived experiences and skills (sometimes a smorgasbord of various roles in differing domains) and think through how they may apply at a particular company.

As David Epstein, author of Range, said, “Modern work demands knowledge transfer: the ability to apply knowledge to new situations and different domains.” What pattern recognition can you apply to this company’s challenges? What similar, interesting problems have you solved before, albeit in a different context?

In my own case, I knew that my prior early-stage startup experiences would help us do similar things at Abridge (and avoid painful mistakes made the first time around). But even at my first startup job, I was able to think through how skills from disparate professional experiences and personal hobbies may fit into existing company needs. For example, I knew my ad sales experience would come handy when we wanted to launch our first AdWords campaign on the cheap. My side hobby as a professional wedding photographer and putting together a WordPress site would come in handy when it was time to create our website. And my experience in general problem-solving would come in handy when on day 1 our website went down, shortly before I had to also provide IT support because our printer was spitting out paper and broke. (I remember my co-founder looking at me when this all happened and saying, “Well, welcome to life at a startup!” 😂

3. Paint a compelling future for the company with you in it. How might you accelerate the company’s efforts?

In making your pitch, the most important thing is to be specific and clear on what you can do for the company. How might you create or level-up existing systems and processes to make things run smoother/faster/better?

As Chloe Yoo, Head of Ops and Finance at HumanFirst said, “As an operator, I can both build and run. This is crucial for early stage startups where the needs of the company change rapidly.” Chloe goes on to say, “A strong generalist will always be a good hire — this gives orgs flexibility when it comes to building out specific functions that come with scale like sales, marketing, and customer experience).”

And beyond the above, there are so many other ways that an operator / generalist can provide value to a company. For example:

• Startups are full of unknowns. A kickass operator can help companies quickly validate various assumptions, strategies, and tactics, before building out a more specialized team to do them.

• A generalist can fill in any temporary gaps in the company, whether it’s due to staffing changes, headcount restrictions, or starting a new department.

• Operators make things happen. They synthesize information, easily context switch, and help people prioritize the work. The best operators I know are hustlers who are efficiency-minded, flexible, and above all — persistent doers.

• An operator with broad exposure to a variety of functions can help startups avoid making costly mistakes early on. Generalists will have a better sense of how various functions work independently, as well as how they can work together to improve the chance of success.

• An operator improves everyone’s lives. They are the glue in the company that holds people together, helps problem solve, and creates processes out of chaos.

The email that landed me my job

Putting it all together, here’s the email I sent to the Abridge CEO in 2019 as my own pitch to create an ops role at the company:

Hey Shiv,

I haven’t been able to stop thinking about Abridge since we met earlier in the week. I think you guys have a great opportunity here. After reflecting on the supplemental material some more, I think you would benefit substantially from bringing on an ops person sooner rather than later. At the risk of sounding too forward, I think that person should be me. :)

Based on my own experiences bringing several new products to market, I think you’ll face a number of operational challenges as you launch your app:

• User acquisition and marketing: As you're first starting out, it will be important to have a passionate base of initial beta testers. I see in your roadmap that Q1 is for branding, but I’m not convinced that branding is the best move for initial user acquisition. In the early days, you’ll probably have a ton of feedback that will inform product development. Branding can come later, when you’ve found product-market fit and you’re ready to scale. For now, I think it’s crucial to figure out how to best reach these initial users through a variety of extremely targeted SEM, SEO, and maybe even high-touch points (e.g. in-person through doctors’ offices). You’ll also want to build up your website content and really tell your story.

• Product strategy: The purpose of a seed round is to maximize your learning per dollar by setting parameters for success/failure, testing hypotheses as quickly as possible, and pivoting when you haven’t found product-market fit. Your whitepaper is impressive in terms of the technical approach; however, you’ll want to figure out a structured way to iterate quickly on an MVP and ensure it’s the right product-market fit before investing too many resources in perfecting your algorithms and scaling the product.

• Account management / customer support / user studies <> development cycle: As with any product, there will be bugs, questions, and frustrated users. Who will manage these relationships, delight your initial users, and escalate feedback to the product/dev team? You’ll need to have amazing customer support so you can transform your initial customers into early advocates who will scale your product via word of mouth.

• Project management: As you grow the team across different functions, project coordination will become more vital in reaching milestones / launch dates. How will you track your launch plan and make sure people have the resources necessary to meet their deliverables on time?

• The other million things you need to get done but don’t have time to as a founder: building your culture, hiring and managing contractors, evaluating software solutions, creating TOS, figuring out internal feedback mechanisms, managing your community of users, dealing with HR/benefits/accounting/taxes, office manager responsibilities, etc.

Here’s my pitch: I’m the ideal person to help you with all of the above and more. I’ve built a company from scratch at Binti and scaled efficient practices at Google. I’m scrappy, I love wearing many hats and navigating ambiguity, and most importantly, I get shit done. I think you’re on to a great idea, and suffice it to say that talking with you about Abridge has me far more excited than going the comfortable route of taking another job at Google.

In terms of next steps, I’d love to set up a co-working day, where I come in and work with you all on some project to see if there’s a good mutual fit. I’ve also attached my resume for more detail on my work experiences.

Final thoughts

It can be easy to underestimate your worth as a generalist, especially in a world where specialized skills are lauded. However, being a generalist operator IS an incredible skillset in and of itself, and your problem-solving, can-do attitude will be an incredible asset for any company. Flex it! 💪

If you have other tips on how you’ve successfully pitched your value as a generalist, I’d love to hear them👇

Leave a comment

📚 Recommended Reads:

• Deep dive: Range: Why Generalists Triumph in a Specialized World (h/t Monik Sheath)

• Quick read: Make Operations Your Secret Weapon

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I’ve been a startup operator for over 8 years now, and if I had a penny dollar1 for every time I’ve been asked “So you’re in operations… what do you actually do?,” I wouldn’t be hustling to make my equity worth something. 😉

While my answer has changed over the years, I’ve never felt fully satisfied with the generalist descriptors, including:

• “I wear many hats… from strategy to customer support”

• “I’m the Swiss Army knife of the company who figures things out”

• “I connect the dots in our team and make things run more smoothly”

The truth is, despite being a prior startup co-founder and now COO at Abridge, I’ve always felt some insecurity in not having a crisp definition of what my role entails, especially when the responsibilities and the challenges constantly change. Unlike a subject matter expert who continues to hone and master their skills over time, I find myself continuing to reinvent myself and my role, depending on the current needs of the business and its people.

At the same time, no two days are the same, and that’s one of the most exciting parts about this role. I continuously shift from operating at 30,000 feet high, to street-level. For example, on any given day I could be leading a strategy session, figuring out a Slack workflow integration, providing feedback on a press release, or ordering a laptop for a new employee.

But, one thing is for sure: as a startup operator, my job is to leverage my generalist skillset to make the company successful. I shapeshift as needed. I get shit done.

Someone recently told me, “If you’ve met one operator, you’ve met one operator.” And to some extent, I think this is true. But I also believe there are many common skills, challenges, and questions startup operators face. The trouble is that startup operators are often n=1 within a given startup (especially at an early stage), and there aren’t as many opportunities to share knowledge within a smaller company.

That’s why I’m creating this space — a place to aggregate tactical advice that helps startup operators accelerate our collective learnings. As a pragmatic dreamer, my hope is that together, we can find a way to go faster and move decades in a day.

If you’re facing any current challenges in your role as an operator, I’d love to hear them in the comments! Thanks for reading, and looking forward to what’s next, together!