Become a Delegation Pro – Four Practical Steps

Are you finding that there just aren’t enough hours in the day? Do you get the feeling you're treading water rather than building your business and doing the work that excites you? There are warning signs that it’s time to delegate and some simple steps to get you started.

Fail to Delegate. Fail your Business

One of the toughest things for any small business owner to do is it to loosen the reins. When you start a small business you’re the chief innovator, chief marketer, chief salesperson, chief receptionist and chief accountant but if you want to grow your business then things have to change.

For me this was in 2009 when we suddenly grew from a handful of customers to a few hundred. I hired a small team to help out, but really struggled to properly hand over the work. I was stuck in the mindset of “it will be quicker if I just do this one thing now, rather than put in the time to show someone else how to do it”.

But of course it is never just one thing. It is one thing times a hundred other things every day of the working week!

So how do you stop being all things to all people? Learn to delegate.

“Only 30% of managers think they can delegate well … and only one in three is considered a good delegator by his or her subordinates. This means only 1 in 10 managers really know how to empower subordinates
John Hunt, London Business School Professor and Financial Times columnist

You’ll notice I said learn to delegate – that was deliberate. Being the super-human that I am, I just assumed delegation was an innate skill I was born with. I assumed everyone else just knew what was going on in my head and I’d just have to say “can you do this thing” and somehow, magically, everything would be done properly and on time and I could just move onto the next task and never have to worry about that thing again.

Wrong. So wrong. 

Effective, productive delegation is a skill that must be acquired. It takes so much more time than you’d think to properly design systems and processes to not only ensure work is being delegated, but also completed to a suitable quality.

Unfortunately, from my experience and from talking with our customers, we seem to only ever decide to delegate right at the last minute, “heck, I am never going to get through all these things today, I know, I’ll be super smart and delegate them all away!”.

Hah! If only it worked like that – it never does.

You know it’s time to delegate when…

  • You get the feeling that every day is about treading water rather than building your business or actually doing the work that gets you excited.
  • Right now, I am spending the first 3 hours of my day replying to email or declining the ~10 vendors who each day want to sell me something, when all I want to be doing is designing our next feature or walking through a new release. Obviously I’m going to have to work out how to delegate email ☺
  • You find yourself telling everyone who will listen that “there just aren’t enough hours in the day” or declining weekend fun because you think a few extra hours of work on a Sunday afternoon will get you ahead (they won’t for long, its just a bandaid)
  • You’ve had the exact same 20 items on your daily task list for the past month (and when you look at them, you get that sinking feeling knowing they’re still likely to be on the list next week too)
  • You know you’re neglecting the critical parts of your business. The really, really important stuff like collecting outstanding accounts or sending out that email campaign that you know always brings you in new sales.

Successful Business Owners Required.
Earn $12/hr (wow!)

I’m guessing you didn’t start your business with dreams of putting in a 50-hour week and pulling down $12/hr.

But guess what. If you are continuously doing tasks, that almost anybody else on the planet could be doing, then effectively you are saying your time is only worth $12/hr.

Or to flip this another way. If you’re a consultant who charges your hours out at $150/hr, but still does the book-keeping because it only takes a couple of hours a week, then you are costing your business at least $300 week in lost billables. Think about this for a second, you are costing your business money by not delegating!

My younger brother used to think like this. Mike runs a successful, one-man, web design business and was umming and ahhing about hiring an outsourced developer to help with the day-to-day grunt work.

“But I could just do this work myself and save the money” was what he kept telling me.

It wasn’t until I pulled a crisp $10 note from my wallet and asked him to spend an hour adding an image to this blog that he suddenly twigged that yes, clearly his time was worth more than $10/hr.

Put simply, when looking at the financial benefit of delegating you have to look at both the cost of additional people and the loss in your productivity if you don’t do it.

Make sure you keep on, keeping on delegating.

Delegation takes time and doesn’t happen overnight, so with every new position, you need to start sooner rather than later.

If you are familiar with agile or waterfall development, then you’ll appreciate the similarities to growing a business. Nothing ever happens in a nice clean, linear growth pattern. Like a waterfall, the type and volume of work ebbs and flows and continuously cascades over and on top of itself.

The best way to identify whether you need to delegate or even create an entirely new role in your company is to constantly work through these three simple questions:

  1. Am I the best person to be doing this thing?
  2. If not, then who else could be doing this thing?
  3. If someone else was doing this thing, then what could I be doing instead to grow my business?

As you fall into the routine of second-guessing your work, collect and dump the results into an Evernote notebook. By the end of the week you’ll have a long lists of tasks ready to delegate onto someone else, someone better than you.

Now comes the hard part – 4 Steps to Successful Delegating

Making the time available to properly document and then train up a person is the real challenge. It’s too easy to fall back on the mindset of “I don’t have the time to organize this work right now, its only going to take 10 minutes anyhow so I may as well just do it myself”

But as we’ve already demonstrated, this line of thinking is a total false economy. What’s more, it is also like a drug. Do it once and it becomes easier to do it again. Keep telling yourself this lie, and before you know it, you have a 20-a-day “do it now and it is done” habit to try and kick.

I’m not going to be all business-author naive on you here and flatly tell you that you must take-time-to-make-time in order to delegate. I’m a realist, we all have businesses to run and in reality the work of planning to delegate has to find space in amongst the work you continue to do but you want to delegate.

So here are four very simple methods to actually get some documentation and systems in place with minimal effort and time.

1 ) Screen casting is your friend.

You are doing this work anyhow, so why not record yourself doing the work and run some commentary – you’ll end up with a handy video to pass onto your team. The bonus here is that not only did you get the actual work done, but you created the documentation at the same time so you now have a permanent record that your hire can refer to rather than repeatedly asking questions.

The best tool for this is by far Jing from Techsmith.

2 ) Explain it back to me

Rather than just assigning someone a task and waiting on them to send you back the completed work, have them take an intermediate step of explaining back to you the work they will be doing. Ask them to tell you, in their own words, how they will tackle the work and what the expected outcome is. Aside from catching any misunderstandings right up front, this has the added benefit of clearly setting expectations around delivery times and quality of work.

3 ) Checkpoints, Milestones and Questions

Successful delegation requires a balance of saying “no” to the urges of micro-managing, yet at the same time never walking away completely.

  • Set aside a period of time each day (or week) when you will be available to answer questions. Ask your hire to store all their questions up for this one session, but remember to let them know that of course you are still available if there’s anything urgent. This will provide structure and stop questions trickling in all day every day.
  • Identify checkpoints from the outset to help you avoid the temptation of constantly looking over shoulders
  • Remember to delegate the whole task. By not handing it over 100% you put everyone in a no-man’s land – no one knows who is responsible for doing what and by when. 

4 ) Feedback

Once a task is complete and work submitted, it is all too easy to immediately move onto the next super-urgent task; only giving an obligatory nod to the work that was done.

The danger with this however is that you’re sending the message that “hey – this work wasn’t important enough for me to spend any time taking a look at”. No one wants to think their work isn’t valued!

You need to review the work properly. At the start review every single submission in detail and then over time reduce either the detail or review every second or third submission in detail.

When you do spot an error or issue, resist the urge to simply correct it yourself. Take the time to talk through the error with the person who made it so they can understand what you require and avoid making the same mistake next time. If you simply do the correction for them, then you will be wasting the time you saved by delegating in the first place.

Oh and remember, be a human and not a robot. Give praise and public acknowledgement where it is due

Give us your best delegation tip…best comment wins a prize.


John Arne Løberg Jørgensen
Friday 15, Nov 2013 1:18 PM

What I like about WORKetc is that I can delegate, AND keep track of things – being the closet control freak I am.

    Steve Westrop | WORK[etc]
    Monday 18, Nov 2013 1:25 PM

    Your secret’s safe with us John…. but can’t speak for anyone else reading 🙂

    Tony T
    Thursday 5, Jun 2014 5:06 PM

    Not only is it nice for someone to be able to delegate and oversee the progress done by someone, but for the person who is working on the project it is nice to know that your direct report is always informed of your progress

Heather Young
Friday 15, Nov 2013 11:17 PM

Hi Daniel. You make many good points in this blog. Delegating is a learning experience and just because you delegate doesn’t mean you do it well. From a virtual assistant perspective the clients we have that delegate well have created processes for the tasks that are done repeatedly. Following the same processes makes it much easier to delegate tasks than explaining how it will be done “this time”.

    Daniel Barnett
    Tuesday 26, Nov 2013 3:10 AM

    Thanks Heather – working with VA’s was actually how we first started on the path of recording our computer screens as a means of best capturing a process and making sure that process was properly passed onto an assistant.

James Hartley
Tuesday 19, Nov 2013 7:06 PM

Great info here Dan – Delegation is one of the things I struggle with, and like John Arne, WORKetc has greatly helped me feel things are “under control” without me looking at every last detail. Crucially this has only been possible by WORKetc covering everything so that it IS technically possible for me to check something if I want to – which greatly eases the transition for an entrepreneur that has started from doing everything him or herself.

My tip would be though (from experience when it hasn’t worked!) is that while it is nice having WORKetc as tracking – you MUST TAKE THE PLUNGE.
This means that you allow your co-workers the space to do it on their own, their way and most importantly, you are not “hovering” (physically or virtually) over their shoulder. Doing this makes them unsure of themselves, transfers responsibility back from them and worst – sends completely the wrong signals to everyone involved (namely that you don’t trust them to do it properly etc).

Delegation is a word that everyone bounces around a bit too easily and frequently (“oh – you must learn to delegate…”) – while the reality of learning to do it properly when it matters is really tricky.

I’m getting much better – but I must say – the process of learning to properly delegate has been an interesting path of discovery for me, and a path punctuated by occasional quite pleasantly surprising results.

    Daniel Barnett
    Tuesday 26, Nov 2013 3:07 AM

    Thanks James and you are right – “You must take the plunge” and then keep taking the plunge everyday until it becomes second nature.

Dallas McMillan
Wednesday 20, Nov 2013 11:50 PM

It’s so true that delegation is a skill and it is also work. It takes time, effort and patience to make each step – sometimes rare commodities among frazzled business owners.

    Daniel Barnett
    Tuesday 26, Nov 2013 3:33 AM

    >>rare commodities among frazzled business owners

    It’s always a balancing act between “do i spend time delegating this now” or “if I do it myself right now it’ll be just be done in no time”. Neither option is right all the time either.

      Sunday 2, Feb 2014 6:57 PM

      Situational management and delegation go hand in hand. The trick (I believe) is to spot the trends and get ahead of the game

Joanne Law
Friday 22, Nov 2013 9:21 PM

Good clear overview of delegation Dan and a prompt to pay more attention to what I can be delegating. Thanks!

Robert W. Bowles
Sunday 24, Nov 2013 3:36 AM

Great stuff Daniel. I embraced this idea when I first started Bluewater over 14 years ago. One of my first hires was a Controller, can you imagine the push back I got when the third person in the firm was the finance guy. What I knew is that I could build around him, and I have.

Now, here is the tricky part, over these years, I have had to continually challenge myself to delegate and delegate well. It is a constant reminder to me as people come and go in the firm and before I know it, those tasks that I successfully delegated are back on my plate, like a boomerang.

I think in part because we don’t have any real middle management in our firm…..maybe some delegation is needed on that level. Always learning and love reading your materials as it does challenge me 🙂

    Daniel Barnett
    Tuesday 26, Nov 2013 3:32 AM

    Thanks Robert!
    >>”we don’t have any real middle management in our firm”

    I often wonder about this – all the modern management theory will talk up the virtues of a flat organization structure, but in reality I’m not convinced such a structure is sustainable, esp when you throw different timezones into the equation.

Sunday 24, Nov 2013 10:46 PM

Delegation is always hard, – let me try by implementing checkpoints maybe that will make it easier, ohh and integrate my phone system with workETC as well 🙂

John Belchamber
Sunday 24, Nov 2013 10:59 PM

Great article Daniel, the art of delegation is indeed one all business owners need to learn, especially as their teams grow.
The good news is WORKetc allows them to delegate, but still keep control 🙂

    Daniel Barnett
    Tuesday 26, Nov 2013 3:29 AM

    “WORKetc allows them to delegate, but still keep control :)”

    Exactly! Intentional design as we needed to delegate off tasks but also make it so easy to regularly check for quality.

Alan De Keyrel
Tuesday 3, Dec 2013 4:11 PM

Delegation is key to company growth… just don’t forget to inspect what you expect. If they do well, give them some more rope. If they let you down, take some back.

Tuesday 3, Dec 2013 9:30 PM

Between France and England, it is the English Channel. Delegation is difficult because we need to support our employees and make them understand that crossing the Channel requires just swim and have experience of swimming for several hours.

Our job is to give confidence. Even with young inexperienced employees is possible.

In any case, I agree with Dan, we need to learn …

    Steve Westrop | WORK[etc]
    Friday 6, Dec 2013 6:05 PM

    Pierre, mon ami, I feel it’s important I delegate here…. feel free to swim over and visit the “UK Office” anytime rather than me swim to you 🙂

Wednesday 4, Dec 2013 2:05 PM

Dan the points you raise are very insightful and I agree with the fact that delegating is something you can only learn through practice. Also, not micromanaging but rather “fostering” or “coaching” by providing meaningful and timely feedback is very important (like you mentioned).

Vrm Staff
Wednesday 4, Dec 2013 8:23 PM

Love it! What a great read! Its amazing how our pride thinking we can do it better than anyone else, or thinking we are saving money by doing a mundane task, can actually cost us money!!!

Thursday 5, Dec 2013 11:14 AM

Great post, very good reading indeed.

Deanna Cox
Friday 6, Dec 2013 9:37 PM

Fantastic information here! I’m constantly hearing from clients that they don’t know how to delegate or they wish they could but they aren’t sure where to start…I’ll make sure to reference this article! Also, I really liked the “Explain it Back to Me” section! Great suggestion and one that we can use in several aspects of work and life.

Friday 6, Dec 2013 11:23 PM

Excellent piece. Obviously Dan has figured out a few things if he can lead/manage/grow WorkEtc while still finding time to churn out thoughtful articles such as this one 🙂 One of the most rewarding parts of the delegation process is the increased trust in your relationship with those employees to whom you have given more responsibilities, and who have stepped up to the task. It never happens in 1 go, but there are breakthrough moments when you realize there is something that you no longer have to worry about because someone competent is on top of it in your company.

Wednesday 11, Dec 2013 8:09 PM

Screencasting is easy nowadays. I have started putting some of the good and usable screencasts in my knowledge base articles, which I can simply link to in a ticket response!

Ben Nighswander
Saturday 14, Dec 2013 1:20 PM

This was much needed for me to read…I got back out of my inbox, moved action to work[etc], and began delegating again. Thank you.

Oscar Correa
Wednesday 18, Dec 2013 5:32 AM

This is actually very true I have learnt the hard way that delegating doesn’t mean giving up control. It’s all about how you scope the delegation.

Saturday 21, Dec 2013 4:44 PM

Technology is not going away so organization through delegation is key to future success!

Michael Hill
Tuesday 24, Dec 2013 4:16 PM

This is a great post! Your point on feedback is spot on. It’s key to not having wasted all that time delegating. We been guilty of that and it exasperating to have to repeat things that could have been avoided with a little dialog session and not just about the results but about the process. Work[etc] has allowed us to give feedback not only on the results but our systems. And we have been able to become more efficient and productive. Great blog!

Friday 3, Jan 2014 12:29 AM

Great article – will definitely be coming back to it again to refresh myself on some of it’s points when needed! Also, thanks for the link to Jing!

Jonathan Hickman
Monday 6, Jan 2014 3:23 PM

Excellent article. Everything person, especially when starting a business, seems to encounter a situation where they think, “If you want something done right, do it yourself.” However, the flaw in that thinking is that you will never get anything done with that attitude. You must delegate and trust your employees to succeed.

Ryan Powell
Wednesday 26, Feb 2014 10:24 PM

Thanks for the tips Dan, great reminders. I am working on this myself and it’s a hard thing to peel off those easy “productive avoidance” tasks that give you instant gratification.

Friday 28, Feb 2014 6:00 PM


I thought so much of this article that I shared it with my team. I also printed the article and posted on my wall. Working at a University, there are student employees and interns I can delegate to for certain tasks. The students are very bright and pick things up fast. My next goal is to do a better job with mileposts and feedback.

We’ve begun making great use of screencasting and are creating a user manual for G Suite/WORKetc that makes great use of that tool.

Thomas Lawler
Monday 2, Jun 2014 6:04 PM

Thanks for this blog post! As a new manager I am still learning by application in the workspace. I believe many of the other comments are correct in saying that it just takes experience, and some familiarity with whom your working with. @jameshartley really hit the nail on the head you just have to take the plunge, and see where things end up. You’ll never grow until you experience.

David Jones
Thursday 19, Jun 2014 1:55 AM

Great article. I used to have trouble delegating as well. I had to get past the notion that I could get it done faster myself and give others a chance to prove that there were capable as well.

William Mullane
Monday 18, Aug 2014 11:03 PM

This was one of those pieces that hit so close to home and was so valuable that I shared it with colleagues, family and friends.

This summer, our team at Boise State University, hosted three high school students for a university learn & work experience. In addition to attending daily classes they put in about four hours per day working for us. This was a great opportunity to practice my delegation skills.

The kids spent most of their time in WORKetc cleaning up data, creating/updating projects and completing social media profiles of our clients. I learned quickly that young people pick things up FAST! Before I could finish showing them a feature in WORKetc, they’d be three steps ahead of me.

The most important aspect of delegation for me was to occasionally check in with my young charges, to ask questions about how they were doing, then to listen and respond to their needs.

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