Sep 13, 2025
Joshua Long
Bottleneck Breakthrough Audiobook - Chapter 11 - Delegate, Document & Automate | Ep32
The Bottleneck Breakthrough Podcast
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“Delegation requires the willingness to pay for short-term failures in order to gain long-term competency.” — Dave Ramsey
If you’re like most business owners, you suffer at times from Commonsense-itis. It’s a sneaky disease that labels so much of what you know and believe as common sense, expecting everyone you interact with to make the same decisions you would in any situation. The higher your intelligence, the higher the odds you are afflicted with it.
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Chapter 11 delegate document and Automate Delegation requires the willingness to pay for short term failures in order to gain long term competency from Dave Ramsey if you're like most business owners, you suffer at times from common sensitis.
It's a sneaky disease that labels so much of what you know and believe as common sense, expecting everyone you interact with to make the same decisions you would in any situation. The higher your intelligence, the higher the odds are you're afflicted with it.
One particular client whom I'll keep anonymous to avoid incrimination was extremely bright, but he had the worst case of common sensitis I've ever witnessed. He projected it onto his personal assistant the most since he interacted with her more than anyone else in the company of approximately 45 employees.
This condition always results in significant frustration for the infected person because their common sense decisions are rarely matched by those around them.
My client was frequently losing his cool with his assistant, especially over minor items such as when she asked whether he wanted store credit or to have the balance of a returned product put back on his credit card.
As you can imagine, his short fuse for having to provide extra guidance on such common sense options made his assistant anxious and full of self doubt about whether her decisions were the right ones. It also made her fearful about asking for his input and setting off another outburst.
The result was that he went through three assistants in as many months.
At the beginning of my work with him, I didn't have the experience to offer a solution at the time, so I just watched from the sideline and I heard plenty of his grief from him over the headache of dealing with flaky assistants. He finally lucked out and landed on an assistant who was extremely overqualified for the position.
She was a bored stay at home mom whose husband made plenty of money, so she was just looking for a challenge to tackle.
Even though she was incredibly bright and could preempt many of the client's needs, she still needed guidance from time to time, which triggered his common senseitis outbursts. Because she was self assured and didn't need the job, she laughed off his irrational fits, which she found very entertaining.
She and I had some laughs over them and the few I remember still make me chuckle. Needless to say, the client was quite fortunate to have found her, otherwise the turnover would have continued forever.
I encourage you to get to the root of your commonsensitis instead of relying upon luck to provide someone willing to endure your abuse. Your staff will become much happier and more productive because of it.
The root cause of Common senseitis is the assumption that your judgment is the default used by everyone else. Since you built your business from scratch, you know every miniscule detail about it, just like you do about your kids or pets.
But just as they don't know every nuance or trait of your kids, your employees will never show up fully equipped to do everything you expect them to do in their hired role. The guaranteed instant cure of common senseitis is to adopt the eight year old management perspective I shared with you in chapter seven.
By viewing everyone in your company as an eight year old, you'll stop assuming that they know everything you know. They're a relatively blank canvas in need of direction and encouragement to learn what you know so they can deliver like you expect.
This sets the foundation to systemize your business by first learning how to delegate effectively. Delegate the creed of those afflicted with common senseitis is it takes more effort to tell someone how to do this, so I'll just do it myself.
This creates a self fulfilling prophecy and self inflicted prison in one quick step. Obviously this is not something you want to perpetuate as you grow your business and have more autonomy to invest your time in whatever fulfills you.
To eliminate this self limiting belief, we'll tackle more of these later in chapter 14. We need to replace this belief with something more useful and supportive.
I like shifting the statement to something along the lines of how easily can I give this to someone who would love doing it and do a great job at it? It's a simple question, but I'm sure you see the difference between the problem and solution statements.
The first kills hope and inspiration, piling on frustration and obligation, while the second creates excitement, multiplying hope and inspiration, making the problem that much easier to solve.
The belief that delegating a task to someone else takes more effort than it's worth grows out of the frustration from poor results caused by bad delegation.
In the past, in the case of my client, he would email tasks to his assistants with very little detail or guidance about how to handle the variables that might arise.
In the case of the product return, he couldn't predict the proffered option of store credit or having the balance refunded to his credit card, but it would have taken a mere second to establish a preference for getting the balance refunded as the default rule once his assistant asks for guidance.
That one step of adding a sentence or two stating how to handle similar situations in the future eliminates having to deal with it again like compound interest.
The return on additional clarity when giving directions adds up significantly over time, saving massive amounts of effort when delegating Delegate effectively Here are the guidelines I recommend using as you start building your delegation skills over Define until you are completely in sync with whomever you delegate to and are consistently getting great results, I always recommend specificity.
You'll feel like you're insulting the intelligence of the staffer at first, but as with a pendulum that is out of balance, you're simply adjusting so it swings back to a healthy clarity. I always add this disclaimer when starting with a new staff member. Forgive me if this includes some obvious stuff.
I just don't want to leave you hanging, uncertain of what to do and have you end up waiting on me for more guidance.
Don't worry about asking questions as it's possible I've still left out something critical Deadline Giving a deadline for the task helps prioritize it in relation to the other tasks they already have to complete. If you're like me, you're not always sure how long something might take.
Again, I include disclaimers here to help get the two of you on the same page. I need this by Friday at 3pm, but if that's completely unreasonable, just let me know what you think is reasonable.
If you have other priorities that might conflict with this, let me know and I'll help you reorder them. Scope so many employees have no idea what a particular task is worth to the company.
Pair that with Parkinson's Law, which says that work expands to fill the time available for its completion and you can end up with staff spending insane amounts of time on the most trivial tasks. I've had staff take hours and hours for something that I had done previously in under 30 minutes.
I was dumbfounded at the wasted time, but came to realize it was entirely my fault because I didn't give them any boundaries. Here's what I now include with every task.
I think this should only take one hour, so if you're not making progress with it after 30 minutes, check in with me to see what might need to be adjusted. If I'm way off on my time estimate, just let me know and we can agree how much extra time is needed.
Authority As I discussed in Chapter 7, having responsibility for an outcome but no authority to do what's needed to ensure it happens is a form of torture for anyone in that position. So I try to grant authority as needed during my delegation of a task.
Zappos is famous for giving their customer service staff the authority to keep customers happy. The stories about it are fantastic and Zappos turns their customers into raving fans.
In the process, I suggest extending authority in stages so the employee doesn't end up hanging themselves with too much of it too soon. With these guidelines in mind, here's a sample task I recently assigned to a new Project manager that delivered a great result.
Hi Jessica, Included below are the transcripts for the testimonial booklet. We're visualizing a 5.5 x 8 book with a color cover and black and white interior that we can get printed at CreateSpace as needed.
Please double check their printing options for this format. I imagine it will be 50 to 70 pages in length, so please organize each testimonial as its own chapter.
Now I just gave her specificity with the print source so she can get the print specs as well as figure out what their limitations are.
Next I said please get the first transcript edited and then have the first chapter designed and sent over as a proof so we can get it dialed in as a template for the rest to follow. So here I've given her more specificity, demonstrating how I expect it to be project managed to reduce as much waste as possible.
I continue with Let me know if you can't get it to me by Monday as our target print date is. And I inserted a date 14 days from now and I figure there will be a few rounds of edits to finalize it.
None of this is in stone, so just let me know if it's unreasonable or not and we can adjust. So I've given her a clear deadline broken up into simple stages.
I finish with Also, the budget for this is $850, so please let me know if you need any help breaking this down between the editor, designer and your time. And let me know if you have a hard time getting the tasks to fit the budget since we can likely simplify the design if needed.
So I gave her scope and authority to get it done. Document. Now we've reached the systemization stage.
The sales pitch for it in the previous chapter was pretty pretty compelling, so re read it if you need a refresher. Without documentation, delegation becomes a hamster wheel of repeating the same stuff manually every time you bring on a new team member.
I don't know about you, but I get bored with repeating myself and it is such a waste of time. The first objective is actually not what to write down, but rather where to store it so it doesn't end up lost or out of sight and out of mind.
There's nothing more infuriating than taking the time to document your processes and train your staff on them only to forget where the documentation is and then have to do it all over again.
As much as I'm a big fan of technology, I found that an old school three ring binder that every employee keeps at their desk is the single most effective documentation library available. It starts out meager with very little in it, but over time it grows to become the operation manual for their job.
Obviously, a file server like Google Drive is a great place to save the digital versions of each process outline and checklist, but relying on it as the only reference tends to be forgotten on a day to day basis.
The added benefit of a physical binder for the documentation library is that it makes it easy to add notes and review it with the employee whenever they can't fully execute with it. Once a document is created, I always point the employee back to it when they come to me for guidance on the related tasks.
I also tell them to come back with their binder if they are still stuck so we can figure out what needs to be added to it to keep it useful for them.
This keeps the documentation alive and relevant at all times, increasing the frequency with which the documentation is used and reducing the frequency with which I am used for such guidance. Documentation Template this may seem overly simplistic, but it has helped every client I've worked with to kickstart their documentation.
I find that too many managers overthink the format and become paralyzed trying to perfect it right from the start. The benefits of using this template are many.
It will reduce the frequency that key steps in any processor skip, like when to call clients with unpaid invoices.
It also allows your staff to show where they might be confused trying to follow the steps even with something you assume they'd been doing for correct for years. Onboarding new staff is much faster when documentation exists that they can reference after they are trained on a process.
Finally, documentation increases the value of your company when you go to sell it. Buyers will always pay more for a well documented company. Get a copy of this template in the Resources section at bbg Li.
Documentation Once you have a process well documented and can rely on the documentation to produce a consistent result, then you might want to look at streamlining it with automation.
Be sure to not skip the step of providing consistent results from your documentation since automating a flawed process is a surefire way to create chaos.
Automation this is a very popular topic in many circles right now, from replacing minimum wage jobs as pay is hiked by regulators to using marketing automation now that software and web technology has advanced so much.
The reality is that automation can be a fantastic tool for your business, but it has a very clear point of diminishing returns in most cases that needs to be identified before pursuing it on a grand scale. Just as testing in a small trackable step is prudent, as explained in Chapter three, I recommend doing the same thing when setting up automation.
Since you have the process outlined from above, you can start breaking it down into segments that might be automated. You might find that automation within a process isn't always feasible, but the transition from one process to another could benefit from automation.
To prevent tasks from falling through the cracks, here's a great example that illustrates client onboarding. You've just secured a verbal agreement from a new client that took a few months to close.
Now you need to complete a coordinated series of tasks in order to land them and get their order fulfilled. You follow the steps outlined in your contract creation process, generating the contract with the agreed upon terms.
You send it via email for signature in HelloSign, a secure digital signature application. Within HelloSign, you have reminders set to go out daily to you and the client until they sign the contract.
This is your first step of automation in the process, so you don't have to manually send out the reminders or even remember to do them. Plus, you don't have to deal with the multiple versions of partially signed contracts since HelloSign organizes it all into one file.
Once the contract is signed, you need to send the invoice as well as an intro email to your client manager who will interact with the client during their fulfillment. Upon signature, HelloSign triggers a notification through a connector app named Zapier.
It uses APIs to connect different software, which creates a task in your project management software for your bookkeeper or sends an email as the task. It also creates a task for the client manager to send the welcome email.
This very simple automation example removes hours of manual effort by multiple staff and reduces the chance that a critical step will be missed, possibly risking the entire contract.
It costs a total of $30 a month $15 each for HelloSign and Zapier, and you can add as many intermediate triggers to it as you see the need, such as a task to call the client if they haven't signed the contract by the third reminder.
As with any new technology, you should double check that it's actually delivering as expected a handful of times in the early stages before you trust it fully.
An actual four hour work week the best example of systemizing a business and delegating it to capable Staff that I've ever seen was in a grocery distribution business owned by a friend of mine, Dale Rainey. Dale got his start in the grocery world early on as his dad owned a discount grocery store in a small mountain town in California.
Dale given the small community, this private store was the go to market in the area. While studying architecture in college, Dale started researching the buying side of the grocery business and found a whole world of opportunity.
Most smart people with entrepreneurial traits find ways to improve a system. To them, it's like an Easter egg hunt with treasures hidden all over the place.
Since groceries are a perishable commodity, except for Twinkies, of course, there is a constant activity behind the scenes to keep food moving and avoid spillage. The store that Dale's dad owned was privately held, so he wasn't bound by the buying agreements of a larger chain the way Vons or Safeway might be.
This gave Dale free rein to research any number of opportunities to improve their buying process.
As he was digging into this world, he stumbled across the segment known as dry goods, which includes items like boxes of cereal, bags of beans, canned food, etc. What was unique about this segment was that it lasted much longer than other goods, especially compared to fruits and vegetables.
It also had fewer distributors because it could be shipped farther across the US Meaning there were greater opportunities to discover with fewer players involved.
Finally, he found that the large chain grocers had strict requirements that resulted in their rejection of a lot of inventory, such as items nearing their expiration date or when there was damage to part of a pallet of goods.
Dale tried out some of this rejected inventory from the larger chains and found that not only was it perfectly good food, but but also, and more importantly, the customers of his dad's store had no objection to it either. He ended up finding more and more of this inventory far exceeding what they could move through their mountain store.
So he reached out to some of the other private grocers in the area and was pleasantly surprised at their eagerness to buy it from him. As you can imagine, this grew into a distribution business on its own and ended up creating a very nice cash flow business for Dale in the process.
Once he negotiated the contracts with the distributors, the rest of the business was entirely focused on receiving and moving the goods to the local grocers he serviced. The logistics of food distribution from multiple sources to many retail stores was complex.
Thankfully, he had a process expert in house and his wife was successfully running her retail furnishing store that he could model after they were both even more motivated to systemize his business during this time. As their first child came along while out jet skiing one afternoon, Dale shared his best delegation hack with me that is yet to be topped.
He told me that whenever he would go on vacation, whatever was on his desk to resolve when he got back would be documented and delegated so he wouldn't be the bottleneck for it in the future. After doing this repeatedly, he had a business that could run almost completely without him.
He would come into the office every Monday for half a day just to review the reports, connect with staff, and keep his finger on the pulse of the company. In the end, Dale simply delegated tasks and had the systems documented for his staff.
Also, little to no automation was needed since the staff could manage the process efficiently. So don't think you need a ton of automation to systemize your business and have it run flawlessly without you in the middle of it.
Action Steps Getting the first system documentation completed is often the hardest step for most of my clients. Here's how to get an easy win and build momentum from there. First, download the documentation template at BBG LI Documentation.
Second, ask your employees to see if someone is interested in documenting the systems in the company. You'll be surprised how many might love doing it.
Third, pick a part of your business that you both agree will be easy to document and get a quick win. If you want to get some real gains, pick an area of the business where you've been irritated by inconsistency and document it.
This is the beginning of the Frustration Fix framework coming in chapter 13. Fourth, once the process is documented, give it to another employee and see if they can complete the tasks following only the instructions provided.
Add more details as necessary. Fifth, rinse and repeat for the critical functions in your business that you noted at the end of chapter 10.
Sixth, create binders for each employee and put the processes they are responsible for inside for easy reference. After documenting many of the processes, brainstorm answers to the following questions with your team to keep getting more efficiency out of them.
The first question is what tasks and responsibilities can be delegated to lower level employees or outsourced completely? And the second question is what tasks can be automated?
You want to reduce manual re entry and eliminate delays waiting on someone that can be handled by software. Trigger.
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