Ten Things: How to Delegate – The Essentials

It’s 5:30 a.m. and no one is up.  You figure if you get up early you can get ahead of the emails and do some productive work.  It’s lunch time.  You figure if you eat at your desk you can get ahead of the emails and do some productive work.  It’s 6:30 p.m. and you just got home from the office.  You figure if you fire up your laptop for an hour you can get ahead of the emails and do some productive work.  It’s 10:30 p.m., the kids are asleep, your spouse is watching “Game of Thrones” and you figure it’s the perfect time to get ahead of the emails and do some productive work before you go to sleep.  It’s the weekend, you… Okay, I’ll stop.  I know you get it.  Just about any in-house lawyer worth their salt has been/is locked in this cycle.  The problem is you never get ahead of the emails and you never have enough time to do productive work.  If you could delegate some of your work, you might be able to break free of this vicious pattern.  That sounds nice, but a big part of the problem is that most lawyers suck at delegating.  Why is that?  It’s primarily because no one ever taught us how to delegate.  They just told us to delegate, which is about as helpful as telling us to “invent rocket fuel.”

I was an “okay” delegator as an in-house lawyer.  I got better over time because I slowly figured out the “how” of delegation.  Even now, as I look back, I realize I committed most of the classic errors and there was a lot more I could have done to better delegate work (and doing so would have made my team/department stronger and me less stressed).  Simply put, becoming good at delegation will allow you to be more productive and get your work done within a reasonable set of hours every day.  Since I know you also want to watch “Game of Thrones” now and then, this edition of “Ten Things” will discuss “how” to delegate:

1.  Why delegate?  Delegating work is important for two reasons.  First, it frees you up to work on more productive and higher value projects (and to do so within a reasonable set of hours per day or per week).  Second, it helps in the development of the delegatee, i.e., the person to whom you are delegating the work.  When properly done not only are you getting back time (for work or non-work endeavors), you are developing the next generation of leaders for the Legal Department.  One of your most important tasks as General Counsel (or head of group) is to ensure succession if you were to leave.  The best way to do this is to develop the talent you already have.  The way to develop people is to delegate ever growing responsibility and complex work.  Proper delegation will also allow you to figure out whether or not someone can actually do the work, meaning are they someone suited for more responsibility down the road, are they solid but limited in their potential, or – unfortunately – whether they are someone that you may need to manage out of the department.

2.  Why do we avoid delegating?  There is a long list of reasons why we do not delegate.  Near the top are usually “I can get it done faster if I just do it myself” and “I don’t trust the person to do a good job.”  Both of these are absolutely correct – at first.  But, delegation is not about whether you can simply push work off your desk and onto someone else’s desk.  It’s about the long game, i.e., moving less valuable work off of your plate on onto that of someone who can (or needs to) learn how to do that work.  You are already the “expert” so there is little doubt that you can do it faster or better.  That said, get over yourself.  You are not the only person who can do the work.  In fact, if you got hit by the proverbial bus tomorrow someone else would ultimately step up and do the work.  Another reason some people avoid delegating work is because they are afraid someone else might get the credit.  Perhaps.  But wouldn’t you prefer to be a manager who has a team of high performers whose work reflects positively on you?  Moreover, whether or not you are developing your employees/team is something that your manager or the Board is looking at when evaluating you.  No company can afford to have only one person who can handle certain types of work and projects.  That is a recipe for disaster.

3.  Be a good “delegatee.”  If you want to be a good delegator, you must first learn to be a good delegatee.  By learning how to accept delegated projects, by participating in the process of assignment, feedback, check-in, etc. you will learn what works and what doesn’t work in terms of effective delegation.  The first time you get a poorly assigned project, i.e., unclear instructions, no feedback, remember the feeling and understand how important it is that when you are in a position to delegate work that you take the time to properly delegate, train, and follow up.  Likewise, as a delegatee, always remember that while it would be nice if everyone delegating work was the perfect delegator, that is not likely to be the case.  Meaning, you need to be aggressive in asking questions, seeking feedback, setting deadlines, and most importantly asking or reminding the boss to be sure to delegate to you in the first place.   Active beats passive every time.

4.  Decide what you can/want to delegate.   Once you’ve committed to delegating work you need to determine what work you can or want to delegate.  There are some projects that will be too important or time sensitive to delegate at first (but you can begin to plan how to work up to delegating those tasks). In the beginning, the projects you delegate will likely be work you should not be doing in the first place either because you have more important things to work on or you have mastered and it’s time to push the work down.  A good idea for helping determine what work to delegate is to keep track all of the different types of work you do over a two-week period (I know tracking time is a four-letter word to in-house lawyers but trust me it works in this case).  Once you have the data you should be able to see work that is most suitable to delegate, e.g., “repeatable” work that you do over and over.  Do this periodically to make sure you stay on top of work that can be delegated.

5.  Find the right person to delegate to.  You need to be able to identify the right person to delegate the work to.  For example, you cannot delegate a complicated legal analysis to your admin or a paralegal.  Likewise, you need to be cognizant of the different levels of skill and experience among the people on your team.  Ideally, you want to find someone who you think has the skill set and intelligence level to handle the work, but who is also a self-starter and not overly sensitive to constructive criticism and feedback (or even “failure” which is certainly possible the first time out with a project).   Hopefully, the work you are delegating fits into their development plans.  Regardless, you should be able to delegate something to just about everyone on your team, from the most senior attorneys to the administrative staff.  For example, if you find yourself spending time reviewing outside counsel bills for compliance with your outside counsel guidelines, that is certainly a task you can delegate to a paralegal or even an admin. It’s just a matter of training and patience.  But, if you ultimately feel that you cannot delegate work to people on your team, then you might not have the right team working for you.  I know finding the right person can be difficult when you are in a small Legal Department or even a “department of one.” Basically, you’re saying “It’s just me.  Who am I going to delegate to?!”  I’ll admit here that you may be out of luck in this situation or you’re going to have to get really creative.  First, are you the only person or do you have a paralegal or an admin?  If so, there are likely tasks you can delegate to them.  Second, and especially if it’s just you alone, is there work you’re doing that might not necessarily be considered “legal” work, i.e., does it really take a law degree to do the work?  If not, it may be time to push back on the business about whether that work should be coming to you in the first place or, alternatively, can you find someone in the business to partner with and who is willing to help out in terms of doing some work on certain projects (e.g., contracts) in order to allow you to get to the more important stuff.

6.  Invest the time to train.  As noted, delegation is not about pushing work off your desk onto the desk of someone else.  It’s a long term strategy to allow you to be more productive and allow others to learn how to do the work.  No one can learn properly if you don’t take the time to teach them.  Consequently, before you start to delegate work you need to come to terms with the fact that delegating will mean a time commitment from you to teach and train the person you delegate to.  The pay-off from delegation comes later, i.e., after the person learns how to do the work.

7.  Learn the “five keys.”  There are five key things to keep in mind when delegating a project.  If you follow these keys your odds of successful delegation go up dramatically.

  • Give clear instructions.  The single most important thing you can do when delegating work is to give clear instructions about what needs to be done and the results you expect.   Be patient.  Don’t assume they “get it” just because you can rattle through the particulars in a few minutes.  Be sure to take the time to fully explain things including, key documents, key people, and key issues.  Put things in context for them.  Before they leave be sure they can clearly and accurately repeat back to you what the assignment is.   This is also the time to solicit and accept input from the delegatee about the assignment.  Their ideas/thoughts can be very helpful.  Listen and incorporate the good ideas and suggestions.
  • Make sure they have the right resources to do the job.  Before you send them out the door, make sure they have all of the resources/materials they will need to do the job.  This can mean sample/form contracts, key emails, access to online research tools, contact information for people they need to talk to/meet with, etc.  Don’t assume the person necessarily knows “where to go” or “what to get.”  Part of training will be to ensure they know what they need and how to get it.
  • Set deadlines.  Be sure you are clear on when things are due.  Don’t assume their schedule matches up with yours, especially if you don’t give them a deadline.  They likely have other work and they will be doing what they think is right in terms of prioritizing, etc.  Give them the due date but then be open to changes if there are conflicts other priorities that you may need to work around.  Also, if the project is really important, set a deadline a few days before it is actually due.  This way you will have some time to rework things if necessary (and you should plan on having to rework the work product the first or second time you delegate something)
  • Meet during the project.  Establish/set checkpoint meetings.  This will be your opportunity to touch base and see how things are going, if they need help, or if they’ve gotten off track.  Again, this is part of the training process.  At some point, these types of meetings may become less necessary as the delegatee masters the topic but in the beginning these meetings are crucial to ensuring the project stays on track, the delegatee is learning how to do the work, and that you don’t get stuck with something you need to completely redo.
  • Review what you get.  Finally, remember that you are still accountable for any work you delegate.  You need to be sure to build in time to review what you get closely.  If it’s not what you need, you must ask them to rework it – but be prepared to explain “why” it needs to be redone (and to do so in “teaching” mode, not out of anger).  At first, you may want to have several checkpoints to review any written work product.  This will allow you to “teach” them what you need, what it needs to look like, what it needs to say and how it must be structured.  If you have bright and hard-working people working for you, they will “get it” but they probably will not come “out of the box” ready to put together the work exactly the way you want/need it.   This may also mean accepting work that is “good enough” vs. “perfect.”  Depending on the importance of the project and the intended audience, you will have to use good judgment on what gets the job done vs. your “redoing” it.

8.  Learn to let go.  One of the main reasons we avoid delegating is the belief that we can do it better ourselves.  If you want to delegate successfully you need to learn to “let go” and let the delegatee do the work in the manner they want to do it.  Delegation is ultimately about empowerment.  Give them the authority to do what needs to be done.  You should be concerned primarily with the results, not the process.  Everyone does things differently.  If you micro-manage the process of how they work then you really haven’t delegated anything and you’ve probably added to your work load – the exact opposite of what you wanted to happen.  And you’ve probably made the person you delegated the work too feel awful because they are not really getting to learn how to do the work for themselves.  They’re just getting uber-detailed instructions from you on “how” to do it.  Letting go, however, is not an excuse to a) fail to provide clear instructions on what needs to be done and the expected results, or b) avoid training the person via a kick off meeting, regular feedback, editing, etc.

9.  Stop waiting for people to volunteer.  If you’re working late, on weekends, etc. and those people working around you or for you are keeping more “regular” hours then you have an obvious need to delegate some of your work.  That said, if you sit there grumbling about how hard you’re working vs. others in the department or those on your team all you are going to get is a nice big “feel sorry for yourself” sandwich.  With very rare exceptions, no one is going to come to you and volunteer to take work off your plate.  You need to ask for help or, if you’re the boss, start telling people to help you.  Make the delegation happen because it sure enough is not going to magically happen on its own.  And don’t worry about telling those who work for you that you need them to take on some of the work.  The worst trait you can have as a boss is a habit of not wanting to “bother” those that work for you with extra work and so you’ll just keep it for yourself.  You may be surprised to find that most of your reports will welcome the opportunity to do more substantive and engaging work.  They will also like the feeling of helping (and learning from) the boss.  But, it all starts with you deciding that you are going to delegate work and that you will delegate it correctly and strategically as described above.  That’s the way you develop your team and the next generation of “doers” at your company.

10.  Post-assignment feedback.  Almost as important as giving clear instructions to start a project is the discussion you have with the delegatee post-assignment.  Be sure to set up some time to give comprehensive feedback on how they did.  This should generally be a positive and encouraging meeting (especially if this is the first time you have delegated a project to that person) and even if the assignment did not come out quite the way you wanted it to.  The key here is to keep being the “teacher,” pointing out what they did well in addition to helping them understand what they did not do so well.  The goal is to help the person become someone who can do the work so you don’t have to.  There will not be perfection, certainly not at the beginning.  Thank them for the work they did and be sure to give credit to them for the work if the circumstances arise where that’s appropriate.  Additionally, be sure you get feedback from the delegatee on how they feel the process went.  What would have helped them do a better job?  What did they like or dislike about the process?  It’s important for you to be open to feedback too, even if some of it is critical – that is the only way you will learn how to delegate better.  Likewise, think of “lessons learned” on your own, i.e., what do you think worked well or could be done differently next time.  What do you need to work on?  Lastly, be sure to encourage your team to speak up when they see you working on projects that you should probably be delegating.


Delegation can increase your productivity and help you get your life back (or at least make it more manageable).  To do it correctly, however, remember the three “C’s” – Commit, Communicate, and Coach.  That is the only way to develop a long term delegation solution.  Otherwise, you might get something off your plate but odds are good that it’s going to land right back on it.   I failed miserably at times but I always tried to get better at delegation so there’s hope for everyone.  Spend the next few weeks thinking about work you can/should delegate and/or seeking out more interesting and challenging work from your boss.  Over time, you will be a happier and much more productive employee and a much, much better manager.  Only around 30% of companies formally engage in delegation training yet virtually all companies demand and expect their managers to delegate work appropriately.  That is a huge disconnect.  You can help fix it.  Be a leader at your company in terms of developing a delegation training program.

Sterling Miller

August 30, 2016

Follow me on Twitter @10ThingsLegal and LinkedIn where I post short articles of interest to in-house counsel daily.  

 (If you find this blog useful, please click “follow” in the top right so you get all new posts automatically, pass it along to colleagues or friends, and “Tweet” it. “Ten Things” is not legal advice or legal opinion.  It is intended to provide practical tips and references to the busy in-house practitioner and other readers. You can find this blog and all past posts at www.TenThings.net.  If you have questions or comments, please contact me at either sterling.miller@sbcglobal.net or smiller@hilgersgraben.com)

My first book, “The Evolution of Professional Football,” is available for sale on Amazon and at www.SterlingMillerBooks.com.



  1. I sure wish my boss at LANL knew these steps on how to delegate. It would have saved my job and provided a good framework for managing our teams and workloads. Oh well his loss.


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