The Hard Part of Doing Less

How to Help Your Team Do More by Doing Less

Quick plug before we jump into the topic today. I recently became a member of the Forbes Technology Council. If you haven’t seen my first article, read it here (it’s all about whether AI is the silver bullet for productivity.)

In my last article, I talked about the “prioritization challenge” and how you can make sense of your priorities when everything feels important.

In this article, I want to unpack a specific aspect of this: the idea that to be great, you must do less. 💪

Doing less sounds simple. We all love to say we’re trying to do less, or that we’ll promise to do less after x, y or z is out the door. But the fact is, doing less is very hard. So hard that dozens of books and countless articles have been written on the topic.

The trouble is, we often assume doing less means we must reduce our actual amount of time spent on work. Sure, we’d all love to work a 4-hour workweek, but this simply isn’t possible for the majority of businesses. Instead, I think we should equate doing less with reducing the number of different things we’re working on. In other words, doing less is about less multitasking, less context switching, and more focused deep work.

Though doing less means you probably can’t go from a 50-hour workweek to a 30-hour workweek 😢... it does mean you can try to eliminate the noise, cut the distractions and focus on the work that will get you the farthest ahead. It means going from a broad set of things to a small set of things and focusing on patterns that are repeatable and scalable.

So, as a leader at a startup, how do you enable your team to do less? Here are some tips from the trenches:

1. Look at software development as a manufacturing process

This might not be a sexy way of viewing it, but it can be useful to draw parallels between software development and manufacturing.🏭 Both need to go through an assembly line of development, QA, and production. And both benefit from process optimization.

As with any assembly line, you will be producing, packaging, and distributing the product when it comes off the line.  It’s critically important to automate the end-to-end processes to keep the team efficient.  I’ve seen a lot of teams talk about the continuous development process, only to stress in the final stretches of getting features out the door.  Even as a young startup, don’t just automate the development process, automate the production lifecycle as well.

You will continuously and frequently build and release product features. The more you can introduce automated workflows and standard operating procedures, the more you can reduce the noise for your team and protect their time for value-added deep work.

2. Try to find patterns that are repeatable and scalable

Along similar lines, look for other areas of opportunities where you can introduce repeatable methods and approaches both in the short term and long term.  This includes repeatable methods for building new features and leveraging existing functionality for new capabilities in the product.

Even manufacturing companies have their “architecture” and build on common parts.  Avoid bespoke development.  It is expensive and leads to significant technical debt.

For instance, at Charli, we’ve recently decided to invest heavily into building our API. On one hand, it won’t have an immediate impact on user experience or delight. However, in the long run, it will result in some fantastic (and scalable) building blocks, as well as save our team tremendous time and cognitive effort.  Sometimes looking to the future can be just as powerful as finding solutions for today.

3. Ensure your senior leaders are providing consistent and persistent support

It’s a scary thought, but it’s critical to remember that you can burn your team out quickly by trying to get them to do too much. It’s been widely acknowledged that multitasking can make you less productive, increase chronic stress and depression, reduce your focus for complex tasks and impair your memory, and contribute to burnout.

All teams have capacity limits and you have to be in tune and aware of these limits.  Be persistent in getting the message across that you need your team to do less (aka less multitasking and more focused work) in order to be excellent. This requires consistent messaging and a strong vision from the leadership team.

4. Get comfy with the possibility of failure and fail fast

Being a startup means being on the bleeding edge of innovation. There are no patterns to follow; no textbooks to open. You must run, fall down, get hurt, bleed, and then pick yourself back up. In other words, bringing something novel to market requires failure, which is hard and scary. 😬

Similarly, if you’re going to encourage your team to do less, it means inherently taking risks. There’s a chance you’re going to get them to do less of the wrong thing. However, the sooner you get comfy with failure, the faster you’ll be able to get back on your feet when things go wrong. Just as you must do less to do more, sometimes you must fail in order to grow. In fact, this is what puts you on the path to being an expert.

One of the keys to doing less is to perform a rapid “lessons learned” exercise and apply those lessons right away--don’t wait.  This means as an entrepreneur, founder, and executive, you have to be intimately involved in the process every single day.

5. Partner and buy instead of build

There can be a tendency in engineering startups to build technology rather than leverage existing products in the market.  This is the typical “build vs buy” that comes up in a lot of discussions.  For a startup to be successful there needs to be more buying and partnering.  Even using open-source products is part of the buy decision.

Ensure that the entire team knows the real value proposition of the company and where the intellectual property resides.  Knowing the value proposition can make the build/buy decisions far easier.  This sounds like a no-brainer at the executive level, but everyone in the company will be making build/buy decisions--and you will rely on engineers to make these decisions on a regular basis.  Don’t get blindsided; communicate frequently with the team and make sure there is a common understanding.

6. Use the right tools to support this mindset shift

Of course, we’re huge fans of our app Charli, and we use it to organize, share and find our content faster. 🎉

There are lots of other tools too that your team can experiment with to help them do less. In fact, we wrote a whole blog post on this topic called 10 Productivity Systems to Try in 2021. The important thing to remember is that not everyone will get value from the same system. It helps to experiment a bit until each person finds one that works for them.

My next few newsletters will be on the topic of Artificial Intelligence, let me know if there are specific questions you have about Charli’s AI in the comments below 👇. I’ll try and address them in my next newsletter.


On burnout and multitasking 

On the software development process

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Prioritization is the linchpin to success.

Here’s how to get it right.

I want to talk to you about prioritization this week. For one it’s been on my mind a lot lately and two we just finished delivering version 1.2 of Charli our biggest release since 1.1 in January. I’m always impressed with what the team can deliver in a short amount of time even if part of me wonders what else we could have squeezed in with a bit of prioritization magic.

If you haven’t checked out what’s new in 1.2 already, go give it a try.  

Ok, shameless plug over...back to prioritization. It’s one of the primary skills that allows teams to stay focused on the right things and execute. 

As a startup leader, do you ever feel like your prioritization skills have gotten worse? Or you get too caught up in the details that you forget to “pull your head out of the sand” and re-prioritize? 😬

The younger version of you was able to march into any interview and confidently answer the staple question: “How do you prioritize a busy workload?” You made a daily to-do list and crossed each item off while still finishing work by 5 pm. You always knew what you should do next and why.

Now, things feel a little different.

For many of us in leadership roles at startups, prioritization has taken on a whole new weight. With increasing daily demands, impossibly squeezed time, and the constant worry of your funding runway ending, choosing the “right” priorities can seem like a near-impossible task.

I’ve been reflecting on this conundrum quite a lot as we move into a new phase of business growth at Charli. My previous entrepreneurial experiences have taught me that 👉 prioritization is the linchpin for success, so I’m trying to be very deliberate and conscious about how we choose our next steps as a company. It’s not an easy process, but it’s crucial.

The thing is, you can’t do it all. You might want to do it all, but you simply can’t. Overstretching your team leads to burnout...and a company is nothing without its team.

On the other hand, it’s unlikely you’ll find the silver bullet to solve all of your prioritization woes. There will always be choices to be made, employees’ time and energy to be protected, and simply “too many” great ideas to choose from. To add further stress to the scenario, startups are on the bleeding edge of innovation. Many times you are the first company to ever do what you’re doing -- and there’s no playbook for that. There’s no proven method or tested approach. You have to carve a path based on a wide range of unknowns.

So, what is a startup leader to do?🙍

Here are some ideas I’ve been mulling over. I think these will help direct your prioritization process and make you feel confident when making decisions. They’re inspired by my past experiences, and we’re living them right now at Charli.

1. Identify what you’re ridiculously good at

You started your company because you’re really good at something. That “something” could be a specific technology, process, skill set, etc. Whatever it is, you probably attracted other people who were good at it and grew your company from that core. Ask yourself: Have I stuck true to that “something”, or did I stray from it somewhere along the way? It’s good to re-evaluate this often to make sure your team isn’t getting distracted by all the shiny new things that pop up. 

For instance, at Charli, we’re really good at AI.💪 That’s what’s at our core. We’ve been tempted to pour our energy into perfecting our web-based UI because to do so is shiny and fun, but we know that too much of that would dilute our AI work. It pays off to know your strengths, be clear on your vision, and stick to it.

2. Look at what’s resonating with your audience

It’s critical for startups to test their ideas with early adopters. Sure, you can make decisions based on a hunch you have, or based on market data or industry trends. But you really don’t know how your product or idea will be received until you test it in the real world with real people. 

By closely assessing how your audience is reacting, you can uncover clues as to what you should prioritize next.🔍 Of course, your audience can’t tell you what needs to be done, but they can sure provide you with hints for success. Listen to them openly to see where your products’ strengths lie. Ask them for honest feedback about the value they’re deriving from it. And then double down on what’s working.  The trick is to pick up on the subtle hints and not get distracted by the noise of constant feedback.

On that note, if you’re using Charli and have some honest feedback I’d love to hear it. 

3. Question if your current audience is the right audience

That being said, be careful about the audience you pick, and don’t think your first choice will be the right choice. At Charli, who we thought would be our ideal user has shifted a few times as we’ve transformed our value proposition and honed in on our AI’s strengths. By asking yourself on a regular basis if your early adopters reflect the right customers, you can gain confidence with the prioritization decisions you make.

4. Balance short and long term goals 

This one is tricky. At Charli, we’ve had to make some tough decisions recently in an attempt to strike the right balance. For instance, we know our API will be useful in the future, but we also know it won’t be the thing that delights our early adopters right now. And right now, we really need adoption more than we need an API. However, if we put all our efforts into delighting users today, we’ll be selling ourselves short in the future. Our API will take some work, so if we’re going to make it part of our roadmap, we need to act on it soon.

Does this tug of war sound familiar?😩 Sometimes scenarios like this feel like a catch-22 and in some ways they are. Prioritizing short-term and long-term goals is a balancing act. While there is no easy answer, it helps to map out a few different scenarios (while acknowledging that you can’t do it all), consider the risks/rewards of each, and then make a decision and stick to it.

5. Keep everyone on the same page

When your window of opportunity is really only a year or two, every week and every day matters. That’s why it’s important to communicate your priorities to your team often and ensure each person is assessing their tasks based on those priorities -- at the beginning and the end of every day.  And right now, it is literally every day that we review, prioritize, balance, and communicate.

Another thing you can do is make ‘growth’ everyone's responsibility. Many companies hire a specific person who is responsible for growing and scaling their business. But in my mind, that’s too narrow. When everyone on the team is empowered to help the company grow, you’ll find better alignment. No one can hide and no one can point fingers. Everyone is involved and working towards the same priorities.

In summary, prioritizing what happens next in a startup is no easy feat, in general prioritizing in any business is challenging because there will always be a trade-off. In fact, some of the decisions you’re faced with could be some of the most difficult decisions of your career. Know that you’re not the first -- and you won’t be the last -- startup leader to be struggling with this. It’s the nature of the beast when you’re navigated uncharted territory.

💬 Want to continue the conversation? Leave a comment below about your experiences with prioritization.

How to Find Your Focus in Today’s Burnout World

It's easier said than done.

Even before the pandemic hit, burnout was spreading through workplaces at an alarming rate. The overworked workforce and especially the overworked small business owner or solopreneur have been on my mind for the better part of the last two years.  

It’s not sustainable for us to juggle so many tasks at once, I’ve been on a personal mission to get more balanced. At least, my own version of balance, where I can work hard and play hard.

It’s not easy, but the downsides of burnout are worse.

Burnout can have wide-ranging impacts on your health, personal life, and professional performance. 

So let’s talk about how you can recover your time, gain control and find your focus again. ⏰ 💪 🔎

The “But I’m Busy” Trap

When you’re working a busy job with plenty on the line (which, let’s face it, describes most high-performing professionals and entrepreneurs), it can be hard to step back and assess the behaviors that are holding you back. I’m guilty of this and so are a lot of the entrepreneurs and busy professionals in my network as well. 

Two common behaviors I’ve noticed among the “I’m busy” crowd are multitasking and context switching. Are you even working if you’re not responding to client emails, while on a video conference with your boss, at the same time as working out on your under-desk treadmill? 🤨

But no matter how productive you may think this makes you, the science shows you’re wrong. Studies have shown that multitasking makes you less productive, lowers your IQ by an average of 15 points, and potentially damages your brain function long-term. We’re just not built to multi-task and context switch so quickly. 

It may feel like if you don’t multitask you’ll fall behind and never meet your goals whether that’s satisfying your clients, scaling your company, or just getting that project over the finish line.

I’m here to tell you, that is bullshit.

We need to let go of this excuse and figure out how to be less busy and get more focused. 

Time to Reclaim Your Focus

Fixing the way we work is a huge interest of mine and is a motivating factor for me as we continue to develop Charli. As I’ve immersed myself in this topic, I’ve learned some things along the way, and personally tested out many approaches. 

Here are some of the ways that have helped me find my focus and I think they’ll help you too. Try them out to avoid burnout and feel better in all areas of your life. 

  • Break up with multitasking 💔 Breaking up might be hard to do, but it’s time to bite the bullet and retrain yourself to work on just one thing at a time. To get started, identify your common multitasking habits: once you’ve learned your bad behaviors, you can begin tackling them. 

  • Kill the context switching 💀 Context switching is the (equally evil) cousin of multitasking. While multitasking involves doing more than one thing at the same time, context switching is jumping between different tasks and projects rapidly, not allowing adequate time to grapple with any task in depth. This is another major productivity killer and path to burnout. 

  • Set your priorities ✅ We often fall back on multi-tasking and context switching when we feel overwhelmed by tasks. In a panic, we try and do everything at once. Instead, take a few minutes at the start of your day to identify your priorities. You can even rank them from “must-do” to “can wait.” While you have to expect the unexpected in business, you can build more control over the tasks you already know about. 

  • Embrace time blocking 🗓 To stop yourself from falling back into bad habits, get granular about how you’re going to spend your time. Time block your calendar with different activities throughout the day: specific times when you’ll check and respond to emails; dedicated time for doing your deep work; and a good amount of time for breaks to recharge. We just recently introduced not one but TWO no internal meeting days at Charli AI. This is to help everyone focus on deep work on those days instead of the constant context switching between slack, meetings, work about work, and finally REAL work. 

There’s a lot of demands on your time and it can be hard to do things differently. But if you can reset your habits and reclaim your focus, you can beat back burnout and feel happier and more productive at work. 

There are lots of other strategies to help you focus, we recently reviewed 10 productivity systems on the Charli blog 👉 Check it out.

Want to stop wasting time searching for the files, links, or other content you need? Try Charli and tell me how it has helped your productivity.

Charli 1.1 Has Landed…

And we are excited about where Charli is heading!

It’s been a little over three weeks since Charli 1.1 landed. #ICYMI, this was a big product release for us and I’m proud of how hard our team worked to make it come together!

The latest version of Charli adds on a suite of exciting new features and capabilities, two of which are standing out as fan favorites:

Charli’s Content Canvas

Designed to make sharing your content easier and more interactive, Charli’s new Content Canvas is a customizable digital canvas that you can use to display and share your documents, images and links. The canvas brings together all of your important digital “stuff” grouped by related key words, hashtags and notes.

When is the Content Canvas useful? Well, let’s say you’re going through a home renovation (like I still am)...

  • As you come across ideas online, send the links to Charli using hashtags and notes that make sense to you, like #homerenovation and #designideas and #doorsamples.

  • When you receive emails from designers with drawings and concepts, forward them to Charli with relevant notes and hashtags.

  • As you’re walking through stores, snap pics of things you like, such as tiles, flooring, or decor, and send them to Charli through your mobile app.

  • When you’re ready to sit down and review everything, simply ask Charli to find your content related to #homerenovation, and Chali will display your links, docs, and pics on a beautiful canvas, which you can then share with your spouse, friends, or general contractor with the click of a button.

The response so far? The content canvas has been a game-changer! The feedback we’re receiving is exciting to see.

For the small business owner…

“I love being able to see all of my content including links in one place. I organize my tags by SKUs so I can share information with my suppliers easily. It’s so convenient being able to share with my team or vendors directly from the canvas without the back and forth between my email, browser, Google Drive, etc.”

Charli can also do double duty as a tool for personal organization…

“Using Charli’s content canvas is so much fun. I'm using it to simplify tracking recipes and plan meals for my busy family of 6. My favourite recipes are tagged #easy #onepot #familyfavorite #30minutes #healthy #ketofriendly. I love that using tags allow me to create content canvasses for any ingredient or theme and share it with friends.”

What are we building next to improve the canvas? 

  1. Sharing the canvas directly with other Charli users 

  2. Sharing the canvas externally to non-Charli users 

  3. Advanced filtering and find options on the canvas

  4. Canvas customization for paid Charli subscribers 

Our brand new Web Clipper (CHROME EXTENSION)

It’s the best way to bookmark your favorite links. We built Charli’s Web Clipper Chrome Extension to help people declutter their digital spaces. Rather than dump important websites or interesting articles in the “Other Bookmarks” folder, the Web Clipper tool lets you simply send links to Charli and never have to worry about losing them again.

When is the Web Clipper useful? Let’s go back again to our home renovation example... 

When you’re renovating your home -- or even simply your bathroom or kitchen -- you’ll probably look at dozens (if not hundreds) of websites, blog posts, Pinterest boards, and image searches over the course of the project. As you come across links you love, you have a choice:

  1. Keep 36 browser tabs open on your desktop so you don’t forget about them 👎

  2. Clutter up your bookmarks with long URLS that have no context 👎

  3. Send them to Charli with hashtags (like #homerenoinspo #kitchensilove or #bathroommoodboard) and let Charli organize them for you 👍

The response so far? People are loving it! Here’s what we’ve heard...

“awesome” “amazing” are just some of the things we’ve heard from our users about our brand new Web Clipper Chrome Extension. People are enjoying the idea of organizing links just like any other content in Charli with #tags and notes.

What are we building next to improve the Charli Web Clipper? 

  1. Clip more than links. Save highlighted text, screenshots, and more

  2. Get a list of your most recent and top links 

User feedback is driving everything we do, and if you have suggestions for what you’d like to see in the Charli Content Canvas or the Chrome Web Clipper; let us know right here. I read through the requests and work closely with the product team on our priorities. 

Our new Content Canvas and Web Clipper (along with the other new features) have made Charli even more useful for people who want to bring their content under control...because, in today’s world of connectivity and cloud, content is scattered everywhere. Charli 1.1 reaffirms our mission to help make it easier than ever to organize content--of all types and from anywhere--all in one place.

Since I’m trying to “build in public” more in 2021 (follow me on Twitter if you haven’t already), I did a personalized tour for you, my newsletter subscribers. You get to see this before anyone else!

How do we fix search?

Find stuff instead

Have you ever stopped to think about the difference between “trying to search for stuff” and “trying to find it”? 😕 If you’re like most people, the answer is probably not – I mean why would you? The phrases sound interchangeable enough.

However, if you’re like me, you’ve thought about these semantics at great lengths. Or, as my wife might say, ad nauseum. 🤢

Though the two sound similar at first glance, there is a whole world of difference between them – especially when it comes to computing.

To make my case, let’s first look at the definitions of the base words themselves…

  • Search is defined as: to “try to find something by looking or otherwise seeking carefully and thoroughly,” or “the act of searching for someone or something”.

  • Find is defined as: to “discover (someone or something) after a deliberate search,” or to “succeed in obtaining (something)”.

When we apply these terms to the digital world, it starts getting interesting.😎


For search to work, everything must be indexed. Search can be likened to a brute force method of making every single detail searchable to a user. The challenge is this puts the burden on you, the user, to craft a query to find what you’re looking for.

The most obvious example that comes to mind is performing a search in Google. When we do this, we’re using a series of keywords that we think will get us closer to discovering the thing that we’re looking for. However, we need to know what keywords to type. And we need to be prepared to sift through the variety of responses to our search query.

This means that search is great for exploring content that’s related to broadly applicable topics (such as “overlanding gear” or “mountain bike repair shop near me”). It's also great when you’re looking for ideas (like “how to achieve a better work-life balance” or “the best productivity tools for SMBs).

Where search falls flat is when you’re looking for something specific. This could be an email you know you received, a file you know you have stored in your Google Drive, or a note you know you have tucked away in Keep. 

Here are some questions from Quora that show email #searchfails:

To make matters worse, the rise of new products aimed at universal search simply compounds the problem. Sure, these apps allow us to search for content across absolutely everything on our computer and cloud, but they still leave users in the same place – but now with a bigger dataset and onus to sift, filter and sort through even more search results.


When you’re looking for something specific within your own content, that’s where find comes into play.

Find – unlike search – it’s all about successfully retrieving the thing you’re looking for. It is much more precise and assumes that the thing you’re looking for exists.

When it comes to the world of computing, find is usually much harder to build. That’s because it doesn't use a brute force method, but is rather far more elegant and targeted. For find to be successful, it must be contextually aware of what you need, how your things are organized and what’s the best way to get that thing back to you when you need it.

At Charli, we have a search function, yes. But what we’re really excited about is our find function. Though I’m a bit biased 😁, I think what we’re on to is pretty damn cool. Charli doesn’t just help users search for their stuff, it uses AI and contextual reasoning to help them find it – and find it fast. Giving you the right information at the right time from anywhere.💥

The next time you’re looking for something, ask yourself: am I trying to search for this, or am I trying to find it?

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