Learn by Doing

Learn by DoingWhile people learn different things in different ways, business is one activity that I firmly believe is best learned while engaging in the activity. In fact I feel that most people learn more in one year on the job than they do in multiple years of school as so many facets and nuances of business really cannot be taught in books or a classroom setting with fictional stakes. The rubber meets the road when working with real people (who have real families), real clients, a real balance sheet, and a real income statement.

It is with that in mind that I picked Learn by Doing as the title of my latest (10th!) collection of notes from Entrepreneurial Thought Leaders lectures.

The book contains a wealth of insight from startup founders and business owners such as Ben Horowitz (Andreessen Horowitz), John Collison (Stripe), and Joshua Reeves (ZenPayroll). While it is free do not let that influence your thoughts on the value. These lectures have provided me tons of inspiration as well as great career advice. I urge you to give it a read and then follow up by listening to any lectures that strike you for even more insight.

Best of luck.

The End of Jobs

The End of JobsWhen I first heard about Taylor Pearson’s new book, The End of Jobs, I was worried that he had written the book that I have been researching. What I found was instead a practical book that outlines how the employment equation is changing, gives examples of people that are at the front of the wave of change, and provides a framework to adapt to the new job paradigm.

Two books that The End of Jobs reminded me of are Escape from Cubicle Nation and The $100 Startup. One of the people interviewed in The End of Jobs was Dan Norris who recently released a book titled The 7-Day Startup. This book is a good supplement to those but with more of a focus on the digital nomad aspect of the new world of business.

The overarching point the book makes is that now, more than ever before, you have the ability to design the lifestyle you want and that entrepreneurship is the avenue to do that. Increasingly it will be the only avenue to do that due to advances in technology and a changing business landscape.

I like his definition of entrepreneurship and a job:

“Entrepreneurship is connecting, creating, and inventing systems–be they businesses, people, ideas, or processes.

A job is the act of following the operating system someone else created.”

He goes on to lay out many of the skills (sales and marketing among them) needed to succeed in the world without jobs that he is envisioning.

There is a particular argument that Taylor laid out that struct me as very insightful if it turns out to be true. He said:

“We aren’t going through a global recession–we’re transitioning between two distinct economic periods.”

I really cannot say that theory is true or not but I am in absolute agreement that we all should prepare as if it is. I have seen a lot of the examples he has laid out with my own eyes as I think most people have. Jobs are less secure and entrepreneurial skills will help you survive.

If I had one complaint about the book is that I think some of his arguments seemed to jump from point to point and could have been fleshed out a bit more (while I’m a big fan of Warren Buffett I was lost about how value investing tied in) or benefited from better examples. In particular the example involving Morgan Stanley and IBM and a bond sale felt a bit tenuous. However he quickly bounced back with a wonderful thought exercise about your local community out of which I readily understood that: entrepreneurship > knowledge > capital.

One other quirk, and I don’t know if this is due to his subjects choosing to be anonymous or the writing style, but I would have liked to hear more detail about the people and their businesses that he used as examples.

One reason this book was particularly interesting to me, and might not necessarily be a factor for others, is that I feel like I know Taylor and many of the people featured in the book due to having listened to each episode of the Tropical MBA podcast over the past five years.

Even without that background I think many people yearning for more freedom or dreaming of making the jump from job to entrepreneur will enjoy the The End of Jobs. It is a quick and inspirational read.

Join the Conversation

You might, like many of us, have some goals or dreams, personally or professionally, that you have yet to fulfill. Sometimes you feel stuck in a rut and wanting more. Often the feeling is one that is self-perpetuating as you lose enthusiasm and the energy to get out of it. Sometimes without taking action to dig yourself out you can end up burnt out or depressed.

Action is the key.

One action that I’m advocating for today is to join into the local, national, or global conversation that it happening around the goals you have both personally and professionally. I believe that participating in, rather than listening in, is a sure fire way to pull out of a rut, reenergize yourself, and getting your brain to work creatively again.

Conversations happen in many ways and in many places: in the open, behind closed doors, in meetings, over the phone, email, on message boards, and in the media. Some of those are available to you and some of those you have to force your way in.

I have an example of the latter from my job. Our company had started working on a web portal for our clients which is an idea I had long advocated for. For reasons I do not know (I was the only person at the company with a technical background) I was not included in almost any of the discussions leading up to the development nor any of the discussions during the development process. The development was outsourced and, while there technically was one person leading the project, in reality there were eight different people who were trying to control the project.

If the project was a human I imagine it felt like this:

I have eight bosses, Bob.

When the portal was finally launched it was something that neither our internal people nor our clients wanted to use. In fact, only one person logged in and interacted with the software in the first four or five months it was live. Obviously there was a problem.

I took this problem to be an opportunity and forced myself into the conversation. The first step was to write up nine pages on what I thought the issues were and ways to improve them (basically it all boiled down to vision and software being a tool that people use to solve a problem). I followed that up coding a different vision of the portal (in 1/20 of the time and for 1/1000 of the cost of the original). I demoed that and also created a forty slide presentation that highlighted the ways it would streamline things for our staff and would scale as we grew.

It was some of the best work I had done in a long time. It had dragged me out of the rut I had been in at the job and got my brain firing on all cylinders. New ideas were popping up as I was trying to sleep and I even had two dreams about it.

What brought me to that point was that I felt that you can only be ignored for so long. I responded by taking voicing my opinions and taking a lot of action. I did not see a downside. By forcing yourself into the conversation the worst case scenario is that you build up a body of work that you can repurpose into a blog, book, podcast, product, or company.

On that project, while I think I did get some people to ask the questions that should have been asked at the beginning, all of my efforts and suggestions were generally acknowledged but not acted upon. For whatever reasons the powers that be decided to continue down the path they were on.

It was not the wasted effort it seems to be. Out of it I have come up with a great idea for a company, an idea for a book, learned Ruby on Rails, and had some amazing discussions with some of my colleagues about the future of the industry.

This blog is another way that I am joining in a conversation. I am using it as a way to reach out to potential customers for StartOpz. I believe those people to be either entrepreneurs or employees at startups or small businesses. They are interested in starting and scaling their efforts to build a successful business. Hopefully some of my posts help them do that in some way. I know I have already learned a lot from them.

When things settle down a bit I also hope to get further engaged in the conversations around the various issues that are important to me and to find ways to help whether that be through charity or more hands-on efforts.

Words can be leveraged more than money can ever be. They are powerful in that they can incite action in others and that other people can pass them on thus reaching more people that you have ever met in your life.

The conversation is happening right now on the web on sites like Twitter and Reddit. It is happening on blogs (write posts and leave comments), in books (write one and self-publish), and in emails (find people in your field of interest and just write to them). It is happening at conferences around the world and at your local coffee shop.

Talking about what you do and what you want to do will get you excited and keep you excited about the efforts you are making to reach your goals. It will incite the action you need to get out of a rut or avoid it completely. It will keep you feeling alive.

The ONE Thing

(This is one of a series of posts about productivity books and the lessons I took from them. The series is: Getting Things Done, A Sense of Urgency, and The ONE Thing.)

The ONE ThingExtraordinary.

If there is one word to use to describe The ONE Thing it is that. The book’s premise is to figure out the one thing you can do that will make everything else easier or unnecessary and focus on that. The premise is simple enough but learning how to apply it, and then actually doing so, is a powerful change in the way you use your time.

(The other reason “extraordinary” is the one word is that the author uses it 115 times in the book. You can tell he is a true believer in what he preaches.)

I am in the middle of trying to start a business. It seems as if there is a never ending lists of things that need to be done. Often it feels like I am treading water and not making any progress. For a while now I have asked myself the question, “What is one thing I can do today to push the business forward?” After reading the book I realized the better question is, “What is the best thing I can do today to push the business forward?”

While I had expected the book’s message of concentrating on one, important thing, I was surprised at the emphasis on thinking big. In retrospect they should go hand in hand but often the big things are not achieved because they have not been broken down into smaller, actionable steps.

At the largest scale the steps are:

One passion -> one skill -> one person -> one life

And they all come back to the book’s central question:

“What’s the ONE Thing you can do such that by doing it everything else would be easier or unnecessary?”

Productivity in all situations

Everybody has the same number of hours in a day but some people seem to get so much more done than others. Obviously circumstances play a big part of that. A childless man in his 20s (the stereotypical startup guy or digital nomad) obviously has more hours to work with than a single mother of two.

I have heard many people say that when they have children they actually achieve more because they learned to focus on the really, really important things in their limited hours.

“When you want the absolute best chance to succeed at anything you want, your approach should always be the same. Go Small.”

Defer the busy work. Find the thing that matters most and concentrate your efforts on that.

When you let your inbox dictate your day, your calendar dictate your week, and have a to do list that would not be finished in months then likely you feel overwhelmed and that the success you strive for it out of reach.

That describe the demands on many of us but success does not come from busy work nor is success correlated with time or effort. Keller does a great job laying out that the results you are striving to achieve can be traced back to smaller, specific actions.


Throughout many conversations I have found that defining what you are passionate about is easier for some people than others. When I ask people I often get a response of “uhh…” followed by the generic responses of “my family” or “my job”. I then try to rephrase the question to, “if you had no other responsibilities what would you spend your day doing?”

Not every passion is something that you can build a business or career around. Nor do they have to be. Simply being able to indulge them is often enough to bring happiness into your life. If a business or career is your goal then Keller lays out a path to which to achieve it.

When you are passionate about something you spend more time on it which leads to developing skills. It is those skills that are what you will be able to build a business or career around.


This might be my favorite chapter of the book as it covers some of my biggest criticisms about the business world as it is practiced (by companies more than five years old). I will not go into those in depth here (you can find some of my rants elsewhere on the site).

One big lie that he covers, and perhaps the one most relevant to the topic, is that everything is equal. Most workers feel that all tasks need to be done and rank them by importance. Not all tasks need to be done. Importance cannot be defined by arbitrary things such as oldest item in inbox or even by anybody but you.

Breaking free from that lie allows you to truly focus on moving forward.

Big Ideas

While thinking big is an amazing exercise, and he encourages you to take your goal and make it larger so if you fall short you still achieve a lot, it can be hard to figure out how to get from where you stand today to where you want to be.

Keller presents a series of four practices you should explore:

  1. Go Small.
  2. Go Extreme.
  3. Say no.
  4. Don’t get trapped in the “check off” game.

Reading the book will provide you more color on those but all are powerful concepts to utilize on your quest to achieve big things.


Keller makes a case that multitasking, instead of getting two things done, results in getting nothing done.

“People can actually do two or more things at once, such as walk and talk, or chew gum and read a map; but, like computers, what we can’t do is focus on two things at once.”

When you are switching back and forth from task to task or project to project you are not finishing anything that is a priority (which I define as things that generate value to you or your business).

Indeed, if you finish one project prior to starting the next, the first project will be creating value while you work on the second. If you are multitasking then you are getting no value from either.

Keller also makes an interesting point in the book that the word priority has been sapped of its meaning be people talking about “priorities”. It is a word that should not be pluralized. The definition of priority means that it should be the ONE Thing and that everything else takes a back seat.


“Willpower is so important that using it effectively should be a high priority.”

The insight that I took from this section of the book is that willpower is a finite resource that must be recharged. One simply cannot ALWAYS be in control of their willpower. A long day of meetings, fires, and difficult decisions wears you and your willpower down thus making it easier for you to decide to skip the gym that night.

He goes into how your blood sugar level and the foods you eat contribute to your willpower.

“If you want to get the most out of your day, do your most important work–your ONE Thing–early, before your willpower is drawn down.”

Work-life balance

When you are focusing on doing one thing other things you view as priorities are going to suffer. It will be a constant balancing act. It is important to realize and accept that if have any hope of achieving the success you strive for.

“Time waits for no one.”

In order to make sure that you are doing your One Thing as well as not letting your family, job, or anything else important to you fall through the cracks Keller recommends time blocking which involves blocking out time on your calendar in advance. Switch tasks when your calendar tells you it is time. This way you will be constantly focused on whatever your one thing for that block of time is.

Other insights

There are many more insights in the book on topics such as happiness, responsibility, goals, fear, and success. All of them end up tying back to the book’s suggestion to focus on doing One Thing in order to get extraordinary results.

Set business goals based on industry outlook

The last thirteen years of my working life have been spent in the financial services industry. A good deal of the last two or three years of that has been spent vainly trying to convince the management of the firm that software is the future. For a few reasons I have been met with resistance.

  1. Complacent
  2. Time frame
  3. Risk

I do not intend to be dismissive at all by using the word complacent. The firm is full of people who are very smart and have been very successful. They do business face-to-face and they way they service clients has not changed in a long time. The adage, “If it ain’t broke don’t fix it”, applies.

The second reason I believe I have struggled convincing them to invest in developing software to service clients is due to time frame. The partners in the firm are all somewhere in the second half of their careers. While they all want a firm that lasts well beyond them, looking out twenty years and they will all be retired.

The last reason is that developing software is a big investment and not just monetarily. It also is an investment in time and focus. A new product is no guarantee of success. It has to be executed at the standard of the firm and of the clients. And it has to be something that clients want and will actually use.

This story has a somewhat happy ending. The firm has decided to move forward with creating a software product. I hope that the vision is strong enough that a great product is the result.

The reason I am telling this story is that I think all businesses really need to stop and ask themselves the following questions:

  1. What is our industry going to look like in one year?
  2. What is our industry going to look like in five years?
  3. What is our industry going to look like in ten to twenty years?

What your industry looks like today is irrelevant. If you work for today you are going to be behind tomorrow.

Over the past ten to twenty years many industries have been changed by technology. Over the next ten to twenty years I expect the rate of change to only increase as technology matures and new ones are developed (AI will be a game changer for a lot of professional services).

A lot of times you are so focused on your business and industry that you effectively have blinders on to what is taking place in the world at large. I have heard it theorized that you cannot revolutionize an industry from within–that it takes something or somebody coming from outside an industry, someone who can bring in different experiences and bridge industries, to revolutionize it.

WIth that in mind it might be a good idea to have lunch or some drinks with a friend or someone you respect and ask them those questions about your industry. Listen to their answers with an open mind and you might end up with a new outlook and a revitalized excitement about your business.

Answering those three questions is critical to setting goals. You need to execute in the short term (one year) while you work on your long term goals. It is the long term goals for your business that, if you execute them, will make you an industry leader rather than an industry follower.

In Wayne Gretzky’s words, “I skate to where the puck is going to be, not where it has been.”

One you have done that then all that is left is to plan your work and work your plan.

We Can All Change the World

We Can All Change the WorldChanging the world is something that should be a goal for all but not all set out to do it. It sounds like the dreams of a college student that people either politely nod at or not so politely scoff at. But it is something that is attainable for all of us.

The world can be changed at a personal, local, national, or global level. The thing about change is that it begets more change and thus ripples of it spread near and far. You can build a business, start a charity, be a big brother or sister, or smile to somebody at the grocery store. All can make at least one person’s day a bit better.

We Can All Change the World is the ninth volume of my notes on Stanford’s Entrepreneurial Thought Leaders series. You can download it here for free. Hopefully it will inspire you to listen to the talks that have inspired me so much.

Reduce busy work. Increase luck surface area.

There is a concept known as luck surface area that suggests that the more you do, and the more you tell people about it, the greater your chance for success. Spend your time creating and communicating with your peers and you will be recognized for it.

The idea that being busy lowers your chances for success seems counterintuitive to that. After all if you are busy then you are by default having more interactions than someone who is not.

Busy work such as emails, Twitter, phone calls, etc. only increase your luck surface area if they are a part of a concentrated effort to network and move your efforts forward.

Being busy does not create the body of work that others will take notice of. Serendipity will not occur from paper pushing but, rather, will occur by setting goals and continually working to achieve them.

But first you must free yourself from the chains of bureaucracy and inefficiency that plague most organizations.

Paper pile - April 2011 - 2 by Sebastien Wiertz used under CC License

Combatting Busy Work

The best way to combat busy work is to implement systems that decrease the amount of time the work takes and, just as importantly, the amount of brain power devoted to it. For most people the place to start is in the inbox.

To start with do not spend all day inside your inbox. Check your email no more than a handful of times a day. You might be under the impression that your customers and coworkers would think the world is ending if you do not quickly respond to their emails but you would be wrong. If people needed immediate responses they would not use asynchronous communication and would instead pick up the phone to call you.

(I am aware that some people inexplicably expect email responses to be no more delayed than the speed of light allows. They often do funny things such as using words such as urgent or ASAP in the body of the email instead of using the high importance flags (and often on things that are not urgent at all). Those people need to be coached and it is up to you to do it or else you will never be able to fully focus on the things that really make a business successful.)

The second step is to turn off email notifications. Disable the new email pop-ups in Outlook and turn off the beeping on your phone. Those take you out of your train of thought and, as a knowledge worker, nothing is more important.

Now you are ready to tackle your emails at your own schedule rather than somebody else’s. Getting Things Done presents a very effective system that can be applied to your inbox. The system is:

“Do It, Delegate It, or Defer It.”

The premise is that if an email only takes a couple of minutes to act on or respond to then do it right then. If it can be delegated then forward it on. If neither of those can happen (it needs more than two minutes of your attention) then you defer it by putting it on your to do list or your calendar and then filing the email away out of your inbox.

(A pro-tip on your to do lists: You can drag an email to your tasks in Outlook or you can forward emails to services such as Asana, Evernote, or Trello to automatically add them. Just like with your emails address your to do list in your own time frame.)

By applying that system to each item in your inbox a few times a day you will arrive at the fantasy state know as Inbox Zero. It is much easier to achieve focus when diving into a project with no emails to address.

To lessen the number of emails you have to address each day setup filters so that certain emails are automatically filed away or added to your to do list.

Once you have tamed your inbox and created a single proper to do list (rather than writing tasks on whatever scraps of paper you have on your desk at the time) you are ready to tackle the busy work.

Start by documenting step-by-step each thing you do for one day. The next day spend some time going over that list (might help to include the boss on this) and identify anything that no longer needs to be done due to changes in the business. You would be surprised at the number of things that people do because they have always been done and nobody has bothered to stop and question it. Stop doing the things that do not need to be done.

Continue looking at the list and figure out where steps can be automated with a little technology. Investing a little bit of time and money automating processes will pay off in spades later.

Now you should have some systems in place to serve as defenses against busy work so that you can work on building the kingdom.

Startup Stock Photos

Capitalizing on Real Work

Begin by taking the time to identify things that are truly urgent which are the activities that are central to your business’ success or survival. That is where you want to concentrate your efforts.

Prioritize the activities and then set goals with actionable steps and timelines for each activity that you are going to create a project out of.

Those projects vary from business to business but could be a product launch, developing a new feature, a marketing campaign, or hiring. The bottom line is that you are trading busy work for the work that pushes your business forward.

That is the type of work that will increase your luck surface area and make others take notice of you both inside and outside of the company.

Four areas you can improve your workflows

Recently at work I’ve been pushing us to do something that none of us do often enough. That is to take a step back and examine the workflows that we go through every day without really thinking about them.

As your business changes, and the technology you use changes, there might be many things that you do currently that do not need to be done anymore, can be done differently and more efficiently, or can be automated.

Documenting workflows is the first step here and, as an added bonus, also the first step for establishing the standard operating procedures that your business should be creating anyway. So this exercise is one that should hopefully pay for itself many times over in the long run as your company grows.

These are four common places where your current workflows might need some work. It is in no way an exhaustive list as every business, and every individual that makes it up, has its own unique characteristics.

Death to the Stock Photo

You find yourself doing repetitive things in spreadsheets

When I first started my job at a financial services firm I spent the first week being shown the ropes. One of my jobs was to track all trades and make sure we got paid on them. This all happened in one big spreadsheet. Every day trade files were copied in followed by lots of sorting and copying and pasting data across many columns. Once a week commission files were received and were manually cross referenced to the spreadsheet.

I made the comment that a database would streamline this process and received the response, “Why don’t you wait until after your first week to make suggestions on how we do things?” (Lesson is that people rarely want to be told they are doing something inefficiently.)

As soon as I was done training and let loose I immediately built a database in Access that trimmed eight hours of work a week down to about eighty minutes. A couple of years later I developed a PHP/MySQL app that trimmed that eighty minutes a week down to about eight.

I love Excel and spend a lot of time in it but if you find yourself revisiting the same spreadsheet a lot, or do a lot of copying and pasting, then there might be better software for that task or a better system you can put in place to manage it.

You find yourself sharing documents via email

Email is great for communications but terrible for collaboration.I find email to be great for communication but terrible for collaboration. It is poor for collaboration for these reasons:

  • Two parties cannot work on a document simultaneously.
    • Once sent you have to wait for another party to send you their revisions before you can continue work on it.
  • Comments live separately from the document.
    • While most office software has the capability to include comments in practice nobody uses that. Instead they include their comments in the body of the email and reference the attachment.
  • Projects lose priority in an inbox
    • For better or worse many people still live their business lives in their inbox. While the project you are collaborating with somebody on might have priority over anything else subconsciously it is losing priority every time your collaborator receives an email that diverts their attention, (One of my big pet peeves is talking to somebody who gets distracted by the new email popup message.) They always read it to see if it is an emergency, maybe respond, but always take at least a few minutes to get their mind back into project mode.

We have just started sharing documents and gathering comments in Slack so it is a little too early to tell if it is a greatly better solution but I suspect it is for collaboration. Dropbox also just implemented comments on documents (I believe last week).

Personally I have found that I greatly prefer collaborating with people on files in Google Drive over files on a shared drive. Even then sometimes people make changes themselves or send comments back via email (less than optimal). Google Docs does has commenting built in that I just need to convince people to start using.

Whatever you are doing currently you should make sure that the software you are using to collaborate is something the compliments your workflow rather than trying to fit your workflow to software. (When all you have is a hammer you treat every problem as a nail.)

Great collaboration unleashes people and creates something that is more than the sum of its parts.

You find the data or documents you need exist in many different places

Most organizations have official ways of storing things. Many organizations also have unofficial ways of storing things as employees have found creative ways around bad software, decades old policies, and bureaucracy. That coupled with the explosion of SaaS in the workplace has companies having their data spread across many applications and servers.

  • Some documents for a project existing as attachments in emails, files on a shared drive, attachments to cards in Trello.
  • Feature requests and/or bug reports being put in both Trello and Github.
  • You have tasks in Outlook, in Asana, and on post-its on your monitor.
  • Multiple databases or web apps house your client data.

I have found that often Enterprise level software does a lot of jobs but it rarely is the best tool for each job. One great thing about the current generation of web apps is that you can often find and use the best tool for a job and it can communicate with your other tools via an API thus pulling all of your data into one place no matter where it is stored.

Tools such as Zapier or IFTTT can help you automatically get the data into the systems you need.

Startup Stock Photos

You need a system to keep track of all of your systems

If you are documenting all of your workflows and creating systems based on those then eventually you might reach what I’m referring to as protocol overload. At our company that is evidenced by having more tracking spreadsheets than you can count. Unless you are intimately involved with a process you might not know that a process already exists or where to find it documented.

Putting all of your systems in one, searchable, place is a great place to start. Excel documents that exist throughout a shared drive (and where you cannot search the contents across multiple files) is a terrible way to store protocols. Instead you could put them inside a company wiki, put them as different worksheets in the same Excel document, or, my favorite, create them all as templates in Asana so you can store the processes as well as implement them in the same place.

Every protocol or standard operation procedure should be periodically reviewed for steps that can be automated or are no longer needed.


Examining and optimizing workflows is a task that takes time but one that will be ultimately worth it. Eliminating busy work and increasing efficiencies will allow your organization to spend more resources on the projects that will continue to fuel your growth.

Office Pet Peeves

Everybody has pet peeves about their office and coworkers. I’m sure even the SI swimsuit crew can’t stand it when the models constantly leave half full juice cleanse bottles all around the set. HASN’T ANYBODY HEARD OF A GARBAGE CAN?

Here are five of my pet peeves from the past fifteen years of work.

Complaining about how busy you are or how many emails you have in your inbox

You say, “I have so many emails.”

I heard, “I’m poor at inbox management.”

Everybody is busy. Everybody has lots of email. In the time you spent complaining about it you could have addressed one of them. Learn zero inbox skills and reap the rewards of better focus and feeling less overwhelmed.

On the other hand, as much as it causes your coworkers to roll their eyes, I am actually convinced that constantly talking about how busy you are is a good strategy for pay raises and career advancement. Your boss likely has no idea what your day-to-day looks like so they will take cues from what you say–particularly if a lot of your work does not pass their desk.

Protocols for one-offs

I’m a huge fan of systems. In fact Startopz was built with them in mind. Implementing them effectively has many benefits including streamlining processes, less dependency on any one individual’s knowledge, and allowing a business to focus efforts on larger projects that move the needle.

However, not every single thing that ever happens in a business needs a protocol. Sometimes there are unique situations or sets of circumstances that are not likely to be repeated and do not need an official company protocol created. If it is the first time it has happened in the past five or ten years then it is a pretty unique occurrence. Wait for it to happen a second time before creating a protocol. Systems are for situations that repeat.

Too many systems will lead to needing systems to manage all of the systems (a dangerous rabbit hole to be sure). You can only abstract away from actual work so much.

Solutions in search of problems

To be fair on this one the issue is that people who present solutions sometimes perceive a problem that nobody else sees. Sometimes it exists and sometimes it is just in their heads. Every solution should be questioned and examined before implementing in order to not waste time and money (potentially lots of like when management wants to use a big name CRM as a backend to a website that receives less than a hundred logins a month when the feature set could be implemented in LAMP in under a week).

One time somebody in our office hilariously asked us to include the work “pink” in the subject line of any email we sent her that was urgent. Her thought was that if she then searched her inbox for pink (a word that does not appear often in our business emails) she would get a list of the emails that required her immediate attention. I did not have the heart to tell her that Outlook has a “High Importance” flag already built in.

Dates in file names

On the shared drive at our office we have dates written out in the following formats:

  • Common Document yyyymmdd.pdf (hard to read at a glance)
  • Common Document mm-dd-yy.pdf (dates starting with months are poor if you have a lot of them that span years)
  • Common Document mmddyy.pdf (one vendor provides us these)
  • Common Document yyyy-mm-dd.pdf

Only the last one is “one correct way.” No room for argument.

This also applies to emails (particularly with Europeans) where dates are written mm/dd/yy or dd/mm/yy.

Refusal to hit F1, RTFM, or use Google

When you do not first try to help yourself you are wasting somebody else’s time. It is very easy to look up answers to most questions that you might have about the software you use day to day. In Window there is a special key for it. In almost any program you can hit F1 and it will bring up the help system for that software.

The delivery of software on CDs was the beginning of the demise of the printed manual. Now that so much of the software used every day is cloud based the manual is instead the documentation on the site. Even more easily accessible than a shelf or a box in the basement where you kept manuals “just in case”. Just look for the world “Help” written on your screen. Or search Google. It has crawled it already.

Speaking of Google. Use it. Love it. It has the answer you are looking for.

if you are on good terms with somebody who constantly asks you easily Googleable questions then you can enter the search term in Let Me Google That For Your and send them back the link. Not recommended for bosses.

Any others?

Drop an email to me (info at this domain) and let me know what pet peeves you have about your office. Or hit us up on Twitter and tell the world about your coworker who never refills the pot after taking the last cup of coffee (#officepetpeeve).

Office Hero: The Office Manager

For a small or medium-sized business the office manager is the glue that holds everything together. They need two racks for all of the hats they wear. They are the owner’s representative to the employees and the employees’ representative to ownership. Having eyes and ears in the back of the head is critical as the owners depend on the office manager to know and and understand all of the nuances and underlying issues that are happening at any given time.

In short, in a small business the office manager has to be everything to everyone.

Trying to write a job description for them is a difficult task that could span pages. Things they do (depending on the office):

Bookkeeping (Account Payable)

Corporate Accounts Payable Nina SpeakingAn office generates a lot of bills. Rent, insurance, vendors for everything, and countless credit card charges. Employees are also going to be submitting expense reports that they appreciate being addressed in a timely fashion so that they are not accruing interest on their personal cards for business expenses.

Being consistent with bookkeeping is important to be able to stay on top of the business rather than being buried under it.

Billing (Accounts Receivable)

Getting invoices to the clients (and getting them paid) is hugely important. Without cash the business can’t run.

“It’s All About the Benjamins” – Puff Daddy

There is a surprising amount of finesse required when billing and following up. A lot depends on things that were not included in a contract but were spoken of, alluded to, and expected. That is why it is so important to have a relationship with your clients.

Client Relations

Clients are the lifeblood of a business. If you do not have people paying you money to do what you do then you do not have a business. While the office manager usually does not provide the product or service you are selling they are one of the faces of the company and probably interact with more levels of the client’s organization that anybody. They keep the pulse of the relationship and are the frontline on fires.

Vendor Relations

Pretty much every business requires the services of other businesses in some capacity. If your core product or service requires that then it is important to cultivate a good relationship with that vendor from both a pricing and service standpoint.

Hiring and Firing

Finding job candidates and screening them might fall to different people depending on the department where the opening is. Doing all of the paperwork once somebody is found usually falls to one person.

We find it is always better to fire people on a Friday.

Firing is unpleasant, needs to be handled carefully, and also involves paperwork. When it happens it is probably best handled by the office manager as the department head might be too close to the person or problem and could complicate the situation.

Payroll and Benefits

I have yet to meet the person that enjoys doing payroll (though maybe firms like ZenPayroll will change that). The same can be said about dealing with insurance companies (I haven’t tried it but have heard good things about Zenefits). Those frustrating tasks will inevitably fall to the office manager at a small company.

Vacation Time (Coverage)

There are a few reasons why most companies track vacation time. Accrued vacation time creates a liability on the balance sheet (needs to be paid out when somebody leaves), to make sure people are not taking more than their benefits specify, and finally to make sure that too many people are not taking time off at once and thus leaving the office short staffed. In larger companies that might be handled by a department manager but in small businesses it falls to the office manager.


Red stapler

Every office needs supplies from coffee to pens to the two types of paper (printer and toilet). A business usually needs to grow pretty big before a dedicated supply person is hired. Until that happens the task is usually delegated to the office manager.

Office Lunches

Everybody loves when the office provides lunch (except the person that has to organize it). While not a thankless task it is usually the person paying for it (the boss or owner) that gets the credit.

Office Parties


Office parties, like office lunches, are often taken for granted by both employees and ownership. If you have ever planned a wedding or other large event then you know how much work goes into it. All of it is above and beyond the day to day work you are doing.


Unfortunately after those office lunches and parties there is usually some cleanup that needs to be done. Often employees do not give it a second thought as it is not part of their job description. When the last person has had their piece of birthday cake it will be the office manager who cleans up.


As we have said the office manager fulfills a lot roles so good psychology is important. You have to be a mother/father, sister/brother, wife/husband, cheerleader, good guy, bad guy, indifferent, etc. depending on the situation. Understanding how people will react to your words helps you shape what you are going to say so that you are fulfilling objectives while sparing feelings.

These are all tasks that an entrepreneur does when they start a business and makes their first few hires. It would often be in their interest to make an office manager one of those hires in order to free up their time to build the business rather than run the business. (And in the meantime check out StartOpz to help manage all of this.)

So, hire a good office manager and treat them right! You will be glad you did.