Leni is the founder of a small SaaS company that works with clients and customers worldwide.
She thrives on the flexibility of remote work and the ease of running her business online.
But some days — rather than being excellent at managing her schedule — she feels like she’s descended into chaos, and everything is on the brink of collapse.
With a small (but distributed) team and a growing, global customer base — establishing priorities and avoiding scheduling conflicts (both internally and externally) has become tricky territory to navigate.
Not to mention stressful.
That’s why my advice to Leni (and you, if you ever feel the same way) is that with everything there is to do, it pays to have some systems in place.
Because they help:
- relieve pressure,
- create more calm, and
- reduce the scattered feeling of juggling multiple schedules at once.
So today, we’ll introduce you to some powerful systems that work.
You’re a manager of one, first (get used to it!)
It’s perhaps a hard truth for some.
But becoming a decent (if not exceptional) manager of one — is a necessary skill for anyone who works for themselves.
And if one minute you feel on top of everything and ahead of schedule, then the next, you are scrambling to keep a project alive and yourself fed and energized — you can likely do with some system upgrades for managing yourself and your workload.
Not to mention, with some personal system upgrades and stress-relieving processes added to your business operations — managing a team or a full client-roster gets easier too.
The Fast Track to Failure: Disrupting core focus time
Where should my attention be right now?
It’s arguably the most helpful question you can ask yourself at any point of your day.
And if you constantly find yourself not doing what you said you’d be doing — then some systems to help add structure and purpose to your schedule will help you remove any conflicts that keep you from doing the work that matters.
We all have moments when focus feels fleeting. But building habits and practices that protect your focus time is invaluable to ensure you’re not abandoning your intentions.
“Real work and real satisfaction come from the opposite of what the web provides. They come from going deep into something — the books you’re writing, the album, the movie — and staying there for a long, long time.”
— Steven Pressfield.
Of course, there will always be times when you have to handle things that might derail your day.
But with a solid set of systems ready to wield when you genuinely need them, you’ll be able to deal with any disruptions. And get back to your core tasks with a clear head.
The shocking snowball effect of the “last-minute meeting” (and a two-step solution)
Of course, scheduling conflicts happen despite how well you design your day.
And unfortunately, when something comes up that throws your entire plan off — it’s not just that hour you lose.
If you get called in to attend a last-minute meeting, the time cost is often more than the meeting itself:
- There is the initial reaction to the disruption — which has the power to throw off the rest of your day.
- There is a scramble to free up your time — or stress out that you can’t possibly make it.
- There is the time it takes to prepare for the meeting — and make sure you’re ready (both mentally and physically)
- Then there is the meeting itself.
Now, let’s say each of these points takes an hour or so to work through (whether it’s recovering your focus or prepping for the event). That one-hour meeting has now taken up four hours you previously hadn’t accounted for.
The “last-minute meeting” is a drain on time and energy resources.
But two things you can do, especially if you’re overwhelmed, unfocused, or your work feels chaotic, are
#1 — Slow down so you can think clearly.
“Whenever I feel things are moving too quickly, I find the right instinct is almost always to slow down and get my thoughts back in order. “ — Mike Maples Jr.
#2 — Remove something from your plate.
“When I get overwhelmed trying to juggle too many balls simultaneously, I ask myself which one or two I can set down — for the moment — so I get caught up on all the others” — Adam Robinson.
We’ll dive into some powerful systems you can swipe to make these two things easier to accomplish.
Double-booked needn't be the end of the world
Systems help support you on your worst days.
They set you up for repeatable success.
And they save you time — because you have existing, documented solutions for fixing your problems.
- being double-booked,
- having a team member unavailable for an important presentation, or
- dealing with the fallout of having to say “no.”
All become more manageable.
With a few practical systems under your belt, dealing with scheduling conflicts, prioritizing meaningful work, and communicating more effectively (with less need to sync up schedules!) is much easier.
So, let’s take a look at some systems that work.
The Swipe File: 13 systems to avoid scheduling conflicts (and skillfully prioritize work)
1. Meditate: Emotional regulation FTW!
A massive stressor — the result of any kind of conflict — is our (often visceral) emotional reaction.
Frustration and fear breed anxious feelings (which can quickly derail even the best of days.).
But meditation and other calming practices can help shift you back into a relaxed state. They add some space between stimulus and response.
“If you are distressed by anything external, the pain is not due to the thing itself, but to your estimate of it; and this you have power to revoke at any moment.” — Marcus Aurelius.
Developing excellent habits for emotional regulation means you can use them whenever you have to deal with the pressure of conflicts (schedule or otherwise!)
I’m a big fan of using deep breathwork for meditation.
So swipe this practice when you’re under pressure and need to take a breather.
- Breathe in for six seconds
- Breathe out for six seconds
- Repeat five times (or however long is necessary!)
Another simple option is to take a walk (preferably without your phone.)
2. Delegate (do not, what others can do for you)
It’s incredible how quickly you can remove any scheduling conflict when you simply rid yourself of the task.
Swipe these questions when considering what you can delegate:
For meetings (when you can't sync up or are feeling the effects of zoom fatigue)
- Is there someone who can run this meeting from now on?
- Is this meeting even necessary, or has it simply become routine?
- Can you move it to an asynchronous approach (more on this later)?
For projects (when you can’t hit your deadlines)
- What pieces of the project can someone else do, even if you still need to have the final say?
- Have you got a network of contractors to ask when you need a helping hand (and quickly)?
- Alternatively, can you outsource some personal chores and errands instead, if it's work only you can do?
Remember: You can delegate almost any process you can document — so make a habit of tracking and mapping tasks you need to do more than once.
3. Quit the incessant micro-managing
Catching up regularly with key people in your organization is necessary when running a remote team.
But if you’re days are filled with nitpicking and needing to be in control — I’ve got news for you — it’s not just scheduling conflicts you’ll have to worry about.
Micromanaging shows a lack of freedom and trust in the workplace. But it also takes up a considerable chunk of time (for both you and the person you’re terrorizing.)
As Brian Casel (founder of ZipMessage) notes:
“Remote work usually offers less visibility of an employee's day-to-day tasks, so managers often resort to micromanaging their teams or asking for too many updates. While it may seem like a seemingly innocent thing to do, it usually comes across as distrustful and interrupts the focus of productivity of most teams.
Organizations can easily navigate this problem by deploying the right asynchronous communication tools to keep in touch with their teams, without breathing down their necks at every step.”
Here are a few do’s and don’ts to curb any micro-managing tendencies you might have:
- Ask yourself why you micromanage and reflect on your need for control.
- Refine your to-do list by prioritizing the tasks and projects that matter most to you.
- Talk to your team about how you’d like to be kept apprised of their progress.
- Renege on your vote of confidence. Tell your team you trust them and let them do their jobs.
- Overact when things don’t go exactly as you’d like them to. Take a breath and figure out a way to correct the situation if it’s truly necessary.
- Go too far. You don’t want to become a hands-off boss.
4. Get yourself an automated (ego-friendly) scheduling link
No, they’re not evil.
Yes, they save time (and help you avoid painful email back-and-forth.)
Of course, not all scheduling links are created equal. And it’s likely why they get a bad rap.
A big gripe seems to be that sending someone to your calendar makes the transaction feel one-sided (and doesn't consider the other person's schedule.)
But at SavvyCal, we’ve fixed that.
We enable recipients to overlay their calendars on top of yours — to find mutual availability quickly. This makes it the perfect scheduling solution without feeling like an ego-maniac.
- Set up your account. It’s free to get started here.
- Choose a URL where your scheduling links will live (for example, savvycal.com/your-name)
- Connect your calendars to block out busy times and create new events automatically. We integrate with Google Calendar and Microsoft Outlook (Office 365).
- Connect your video conferencing app. We integrate natively with Zoom, Whereby, Google Meet, and Microsoft Teams.
Once the setup wizard is complete, our magical internet minions will create your first scheduling link and take you to your dashboard. Then you can share it with whoever you need to!
5. Never go “full capacity”
We all need wiggle room.
Booking yourself solid and scheduling your calendar down to the last minute is a fast way to feel overwhelmed (and gives you no room for error.)
It’s simply not a smart way to work.
- What if your kid comes home sick?
- What if a client cancels a major meeting and needs to reschedule?
- What if YOU get sick or need to shift your priorities?
Flexibility to adapt to unforeseen changes in your routine and schedule is paramount. And you can’t do that when you’ve wiped out any wiggle room.
Here are a few things you can do to make sure you don’t overfill your schedule:
- Introduce event buffers to all meetings and calls (15-20 minutes on either side will help.)
- Underload your to-dos (i.e., commit to significantly less every day.)
- Leave intentional blank space in your schedule for free time, focus time, or the inevitable last-minute meeting.
6. Skip unnecessary meetings
Gracefully bowing out of meetings that are either unnecessary or irrelevant to you is one of my favorite productivity hacks.
Mainly because, in most cases — you can get the same information asynchronously.
One of the first actions when you begin with an async approach, is to evaluate the meetings you do have and decide whether to keep them or not.
- Is it purposeful?
- Does it have a clear outcome?
- Who does the result of the meeting impact?
- Is it simply a presentation of your thoughts?
These questions can help you evaluate whether a meeting is necessary or if you can change how you collaborate or communicate for this particular project or task.
8. Abolish “behind schedule” from your list of problems
What you tell yourself matters.
And when you’re constantly worrying about being “behind schedule”, it’s significantly harder to feel like you’ll ever catch up.
And sure, having practices in place that allow you to get back “on schedule” are always helpful (like hammering the scope of a project or canceling something off your calendar.)
But what can often work better — is to ensure you start each week fresh.
Instead of bringing last week's “not done” list over into this week — re-establish your priorities and to-dos at the start of each week. This presents the opportunity to recover from mishaps, roadblocks, or unintended distractions.
Essentially you want to reset your schedule each week so that you’re never feeling behind (at least not for too long.)
9. Prioritize like a professional (not a procrastinator)
Even the most successful people struggle with how to prioritize their work.
But thankfully, there are plenty of systems you can try — to help ensure you’re working on the most significant, meaningful, and fulfilling work (you know, the stuff that actually moves the needle for you).
Here are a few of my favorites:
- Warren Buffett’s “2 List” Strategy — You list your top 25 tasks, goals, or projects, then eliminate ~80% of that list by circling your top five. The idea is to focus only on those things to direct your attention and increase focus.
- The Eisenhower Decision Matrix — This visualization tool forces you to differentiate between the urgent and the important. Create your decisions matrix using the following parameters: decide, do now, delegate, and delete. Then allocate your tasks accordingly.
- Factoring in significance — For any task, ask yourself, “how long will this matter?”. If urgency is “how soon will this matter?” and importance is “how much does this matter?” — using significance can help you decide which tasks will have the most impact long-term.
7. Avoid accepting things too far in the future
As Jason Fried (from 37 Signals) notes:
“I’ve simply realized that the further out the yes, the more I regret the moment when it comes due. Because there’s no cost now, it’s simply too easy to say yes about something deep in the future. Further, a future “yes” ultimately means that the past controls your schedule.
By the time you get around to later, your calendar is already filled with prior engagements. That limits what’s possible in the moment. Few things bother me more than wanting to actually say yes to something today but being booked by a previous yes I said weeks or months ago. “
And on that note…
10. How and when to say no (crowdsourced!)
What I’ve found to be most helpful when it comes to declining invitations or opportunities is to take a few notes from others.
In his book Tribe of Mentors, Tim Ferriss asks, “in the last five years, what have you become better at saying no to?”.
Here are a few of my favorite answers (in regards to our topic today):
From Richa Chadha:
“When I am straightforward and sincere about my needs, I find that no one is offended when I say no. Those who are offended perhaps don’t value my needs.”
From Neil Strauss:
“What’s helped with saying no to others is asking myself first if I’m saying yes out of guilt or fear. If so, then it’s a polite no.”
From Esther Dyson:
“Ask yourself: Would you say yes if this were next Tuesday?” It’s so easy to commit to things that are weeks or months out, when your schedule still looks uncluttered.”
From Kevin Kelly:
Whenever I try to decide whether to accept an invitation, I pretend it will happen tomorrow morning. It is easy to say yes to something happening six months from now, but it has to be super fantastic to get me to tomorrow morning.”
Plus, this swipeable email template from Danny Meyer on "how to say no":
Greetings and thanks for writing,
I’m grateful for the invitation to participate in Tim’s next book project, but I’m struggling at this moment to make time ends meet for all we’re doing in USHG. Including my ongoing procrastination with my own writing projects.
I thought carefully about this as it’s clearly a wonderful opportunity, but I’m going to decline — with gratitude.
Know the book will be a big success!
Thanks again, Danny
12. The polite rescheduling prompt
First, if you have to cancel something you’d previously said yes to — please don’t beat yourself about it.
In most cases, good people won’t assume bad intent. And they’ll understand that, sometimes, stuff just comes up!
I recently had to reschedule a podcast appearance (twice!). The first time, my toddler was sick and made me sick. Then when I rescheduled, I forgot my husband's prior engagement and realized he wouldn’t be able to be on toddler duty while I was on the call.
I cringed hard when I had to reschedule again.
Of course, it was totally fine with the host. And he didn’t even mention it. And all I had to do was send a polite rescheduling prompt.
If you use a tool like SavvyCal, you can quickly reschedule meetings and catch-ups. And craft a polite rescheduling prompt with an easy way for recipients to choose a new time.
Don’t overthink or overcomplicate the process just because you feel bad :).
11. A Single Source of Truth (for schedules, tasks, and everything else!)
A single source of truth (SSOT) is a powerful system for staying organized, keeping in sync with anyone you work with, and maintaining a buildable database of everything to do with how your business operates.
It’s not the tool that matters here but the reflex to direct you and your team to one place, where you store all your business information, ideas, and schedules.
To start off, you don’t need much. Just a simple way to track these things:
- What are they doing? What am I doing?
- When are they available? When am I available?
Then you can build it out to whatever you want or need it to be.
13. The mind-blowing magic of an Async-first approach
“Async is the freedom to collaborate on our own timelines, not everyone else’s. It’s the power to protect our best hours for focus and flow. It’s the peace of unplugging, knowing we can pick up where we left off.” — Amir Salihefendic (CEO of Doist)
If you want to avoid scheduling conflicts once and for all, an async-first approach to your communication and collaboration can make that possible.
We go deep into how to use Asynchronous Communication in your business in this article:
So we urge you to have a read of that.
And if you want a sleek solution for scheduling (and rescheduling) with ease — you can get started with SavvyCal for free.