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Proactive Resourcefulness: Mastering the Art of Anticipation
👉 Click to download your FREE Info Finder Cheatsheet here!
About proactive resourcefulness
Operations roles are tricky and tough, not just because of the sheer amount of work you have to do. To be an amazing operator, there is an incredible amount of ambiguity you must navigate in your role.
During my career as an operator, one of the main takeaways I’ve had is that efficiency isn't just about doing things quickly - it's about anticipation. That's where Proactive Resourcefulness comes in.
I define proactive resourcefulness as anticipating and finding information to complete tasks without outside guidance, thus saving time and enhancing strategic decision-making.
Being an operator is less about being a psychic, and more about being a detective who sleuths and finds clues, even before anyone else knows they need them.
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Why it’s important
Time is the only resource you can’t buy more of.
This is especially true for your exec.
To remember how important it is, I frequently ask myself, “Is this question really necessary for them to answer?
Would I pay $50 per answer they give me?”
Even asking it this way helps me scrutinize whether I really need their help, or if I can do it myself.
If you take nothing else away from this write-up, take at least that part.
By exercising proactive resourcefulness, you are digging up information before being asked. That means you're not only saving time — you're showing you're two steps ahead. And execs love it when you think faster and more in advance than them.
Proactive Resourcefulness not only sharpens your critical thinking, but also shows you’re not just a task-doer: you're also a strategic thinker. Demonstrating both of these skills is one of the quickest ways to build trust with your exec. In fact, proactive resourcefulness might be the best way to build it from a business perspective. You prove that you’re reliable, dependable, and sharp.
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When to Use It
Proactive Resourcefulness is usually best exercised when the information you’re looking for could be documented, and is therefore searchable.
Here are a few places you can search for the information you need:
- Calendars (Google Calendar, Apple Calendar)
- Inboxes (Gmail, Superhuman, Outlook, all email accounts, including personal and work)
- Collaborative communication spaces (Slack, Microsoft Teams, Discord)
- Digital note-taking platforms (Notion, Evernote, Apple Notes)
- Cloud storage (Dropbox, Google Drive)
- Password management apps (1Password, DashPass)
And here are a few examples of information types you could probably gather on your own, along with common culprits on where you can find such kinds of information. I've created an easy graphic for you to reference here.
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The How-To Guide
How to Sleuth
- Discern: Assuming you know what you’re looking for, establish whether the information is searchable or not. If it is, roll up your sleeves - it’s detective time.
- Search: Start with the most likely location of finding it (as you can probably tell by now, inbox, calendar, and notes are your friends)
- Exhaust: Don’t leave any stone unturned - get creative. Usually, you can probably grant yourself access to something using the password management app to log into accounts to sleuth your information.
- For example, if you can’t find your exec’s frequent flier number, you might log into their Expedia account to find it there instead.
- Think critically - and obviously, don’t do anything unethical.
- Try to keep your search to 5-10 minutes, so you’re not going down too deep of a rabbit hole.
If you’re not successful in your search
Once you’ve sleuthed, if you’re not successful in finding what you need, communicate this with your exec. You can do it one of the following ways:
👉 In your async channel - if you don’t have an async channel setup with your exec, set one up. You can learn more about how to do that here.
- Save your “ask” from taking up precious in-person/live time - post your question in the async channel.
- Bundle all your questions into one message for the exec, rather than pinging them over and over again (this is a good rule of thumb, in general, so you don’t annoy people with too many separate pings. How would you feel if you were pinged multiple times with multiple asks, versus one full ask? You wouldn’t like it much, either.)
👉 SOD or EOD reports (start of day / end of day reports saying what you plan on doing or accomplished)
- Bold your questions as sub-bullets under the subject at hand
- See if you can get them to give you the shortest answer possible: yes, no, or single-word/single-sentence responses
- I like using this format:
👉 During 1-1s
- Resort to this only if you already have a 1-1 happening soon!
- Bundle all your asks across multiple tasks and projects into one rapid-fire topic, and don’t take more than five minutes doing this.
- See if you can get them to give you the shortest answer possible: yes, no, or single-word/single-sentence responses.
- Here is an example of how I would plan for this topic (fill in the task in brackets):
👉 During other relevant meetings
- Resort to this only if you have a task that is project-related and it makes sense to bring it up during the meeting so everyone is informed on your progress.
- Write your questions out ahead of time and share it as a topic within the agenda
- Again, follow the template outlined in the graphic above under in the 1-1 section. It shouldn’t take more than 5 minutes - if it does, you can probably write a little more thoughtfully or (even better) send it out asynchronously instead of eating up valuable meeting time.
If you are successful
Once you’ve sleuthed, if you are successful in finding what you need, communicate this with your exec by practicing the following:
👉 Proactively share the information you found in your update via whatever established comms form you have
- If it’s project-related, try informing under the project task board
- If it’s a one-off task, try posting this update in your SOD/EOD report
👉 In the update, share a screenshot of the action you took and where you found the information.
💡THIS IS VERY IMPORTANT: At some point, it is inevitable that you will find outdated or stale information. This is actually why reporting your findings to your exec is so important - so they can catch the error and correct you. As you collect updated information, update your records so it’s easy to access in the future, and you don’t have to ask the same thing twice.
Don’t shy away from making these kinds of mistakes. These are easy, fixable mistakes, and they’re not mistakes that were caused by you - it is not unusual for information to age quickly.
Execs should feel fine with correcting this kind of error (and if they’re not, feel free to send them this part of the write-up 😉) - this trade-off is usually preferred because…
- You tried your best to complete the task without bothering them
- You checked in with them before sinking hours into doing something
- You reported your findings at the appropriate time for them to catch your outdated information
- You’re going to be more right than wrong using this process (there will usually be more relevant information than stale information)
- You will now have the chance to store the newest information somewhere searchable for both you and them
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The Last Step
(Don’t forget to include this step to really reach your DOD!)
No matter what, once you’ve identified the relevant information, whether you found it yourself or your exec had to correct it, store that information somewhere.
You are therefore making your exec’s entire life much more accessible and searchable for them, meaning they can move faster (and of course, it goes without saying that that means your job will be way easier too and you can move faster as well.)
Say for example, your exec recently got approved for Global Entry when traveling, but for some reason, you can’t find their global entry number anywhere. You check their email account, and there’s no notice from the government (it turns out, that pesky spam filter accidentally filtered it out and trashed it after 30 days. Bummer!)
You also know you won’t find that information in past itineraries, calendar events, or the accounts of various airlines your exec likes to fly, because this is new information that hasn’t ever been used.
In this case, you log into their Global Entry account and secure the number. At this point, I would heavily suggest:
- Storing the number as a Secure Note in their password management app
- Screenshot the number saved in the app and send it to them to inform that they can access their number at any time
- Add the Global Entry number to their relevant accounts, e.g.: their preferred airline accounts under their profile, Expedia/other travel booking sites, etc. - screenshot that and send it to them too
In this case, everyone wins. You have this information now much more readily at hand, which makes you faster, and your exec now remembers they have it saved in case they’re in a pickle at the airport and can now pull it up quickly in the password management app they use.
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Conclusion
Proactive Resourcefulness makes you the ultimate ally – someone who not only carries out tasks but also anticipates needs and acts on them.
By doing this, you become an indispensable asset who makes life smoother and more efficient.
And when you master this, you're not just a Chief of Staff or an Executive Assistant – you're a strategic partner in the truest sense.
As a friendly summary, here are the steps:
- Determine whether you can sleuth the information you need
- Exhaust your search using common sense, but take no more than 5-10 minutes
- If you find the information, report it to your exec and use screenshots
- If you don’t find the information, be smart about how you ask for it
- No matter what, always update the information if it’s new, or if it’s replacing stale information, and screenshot it to inform your exec about the changes
