Delegating: Are You Ignoring This Key To Success?


In this week’s issue of the Technology Leadership Newsletter, a particular article from the Harvard Business Review caught my attention: “More Direct Reports Make Life Easier”. This article was interesting to me because I am little enamored with the concept of non-hierarchical leadership.

I love the concept for many reasons; if you hire smart, motivated people they don’t like being managed. All team members become part of the decision-making process, and with less hierarchy employees are empowered giving them a great sense of ownership and improving everyone’s ability to work together.

This article argued that enforcing hierarchy is actually better, because it reduces costs, and improves communication (there is a direct route up the chain of command, and so less information gets changed and confused along the way). And of course there are pros and cons, and no one process and structure will work well in every company and team.   Which leads me to this postas I was thinking about hierarchy it got me thinking about delegation, and while I still am not a fan of hierarchy, I think delegating is incredibly powerful and not necessarily intuitive or easy.



Delegating is a classic example of how a manager can put a hierarchical system to good use. You can prioritize your own set projects and have others completed by your team, thereby getting everything done faster. Delegation is powerful and can benefit everyone involved (the manager, the employee, and the company), successful delegation is one of the most underused leadership skills around.


There are lots of reason we have mental roadblocks that make delegating difficult (here are some of my own personal feelings, but I am sure there plenty of others, too):

  • No one could do this project as well as I can. Chances are, if you’re in a leadership role, you’re driven, successful, and good at your job.  You probably were promoted into that role because you did well, and your first instinct to do most tasks may be that you are the best choice, for every project.
  • It will be faster if I just do it myself. Taking the time to go over a project with someone else when your inbox is already overflowing with reports, your calendar is filled with meetings, and deadlines are looming – can seem like a waste of valuable time.
  • I can’t control a project someone else is doing. Who doesn’t like to do things their way? Giving someone else the opportunity to do it differently means giving up control, and that can be hard.
  • I don’t trust anyone on my team to handle this. It is not always obvious when to delegate tasks, especially large important ones that might be a stretch for someone on your team.   When it comes to important things I still get scared delegating them.
  • I want credit for this success. Few of us are likely to admit this one out loud, but we all like being noticed for doing a good job. Giving the spotlight to someone else doesn’t come easy.  I struggled with this for years when I was first promoted to management.  Completely letting go of praise and finding satisfaction from within was a long journey for me, and I notice there are moments I still struggle with it.
  • I don’t want to be held accountable if someone screws it up. On the flip side, who wants to take credit for something bad? It can be hard to trust someone and then be let down by the results; and then be the one who shoulders the consequences when things go sideways.
  • I tried delegating and it didn’t work. I once tried delegating some recruiting tasks, and ended up getting so frustrated giving instructions and then being disappointed with the results I had to redo all the work itself.  After that it took me working with a new admin 6 months later before I was willing to try again.
  • I don’t know how to delegate. I have talked to so many successful entrepreneurs and managers, who would rather just continue with the status quo than trying to delegate. Some people are just uncomfortable asking for help or assigning tasks.

In the moment, day-to-day, your inner lawyer may leverage some or all of these excuses, leaving you to power through your projects, instead of looking for ways to be more efficient.

But recognizing these reasons is the first step.  Learning to be a great delegator not only saves you time, but also improves your team.

If you are in a management role part of your job description is being a teacher and building up your team.   Your goal should be to seek out ways to train your team out of their current roles. The more they can do, the more you can focus on what you’re really good at (and what you like doing, too).


“Your most important task as a leader is to teach people how to think and ask the right questions so that the world doesn’t go to hell if you take a day off.”  –Jeffrey Pfeffer, Stanford University School of Business


It’s nice to think you have everything under control, and it can even be a bit of an ego boost to be indispensable when you’re the only one who can handle certain tasks.   But it’s not sustainable, and it’s not good for you, your team, or the company.

One of the hardest issues I struggled with when I transitioned from being a software developer to a manager was missing the feeling of satisfaction I got from praise for my work. When you’re delegating (effectively) that little boost of praise goes away when your team produces successful work, and you have to learn to get your satisfaction elsewhere. It’s tempting to hoard projects so you can continue to get that external boost – and this is especially true if you are in a player/coach team lead role (you know, the dev leads that still spend a large portion of their time coding and contributing to core products).  It sounds terrible as I am typing it out, and I am appalled to even admit that this was something I did when I first moved into management. 🙁  [don’t judge – we all have to start somewhere!]


Even if it is possible for you to do everything, nobody can be the best at everything. There’s probably someone on your team who would enjoy doing a task on your plate, or someone who could grow their skills by doing something you’ve done a thousand times.

Things get done faster when you delegate, and your employees become more effective when they can do more. Not only do they learn the particular task they’ve been assigned, but they amass other skills by virtue of doing their new project. Helping create slides for a PowerPoint presentation, for example, isn’t just about learning PowerPoint; it’s about research, formatting, elements of a good presentation, etc.

You also appear as a more effective manager when you are able to task your employees with certain responsibilities. Remember that as a manager it’s actually not your job to complete every little task that enters your realm; in fact, it serves your career and professional image better if you are able to prioritize tasks and distribute work to capable team members. Think quality over quantity.


BUT Delegating actually creates a more egalitarian “flat” structure.


Even though – on the surface – delegating looks like a very traditionally hierarchical part of the workplace, it’s actually a fantastic tool for empowering your employees and creating fluid relationships within your department and organization.

By giving your employees more responsibility, you are communicating to them that their work is valuable and that you trust them to handle their new tasks. When your employees are empowered in this way, it counteracts the hierarchy mindset. Instead, the flow of work between boss and employee is fluid, and you each become integral to the other’s success.


Start Delegating


Ready to start delegating? Here’s my list of guidelines and best practices:

  • Start doing 1:1’s now.

1:1’s are so important, especially if you want to start delegating effectively. In 1:1 meetings, you get to know more about your team members individually, which is important for establishing trust and also for finding out where their interests lie. It’s much easier to hand over a project to someone you know, so use 1:1’s as a chance to see *who* is on your team! 

I always try to give people projects I know will interest them. Not only does it make it a better experience for them, but they’ll also try harder because it’s something they care that aligns with their own personal goals and interest.  Everybody wins. 
  • Track your daily time. 

Do you have tasks that take up big portions of your day? Often we aren’t aware that we’re doing these tasks, or how long they actually take (hello, status mails!  I aspire to be like Larry – the amazing Director of Product at Decide, who is probably the fastest status mail writer I have ever met). Track your time – on paper, with an app on your phone, wherever you’ll do it consistently.  Once you have a record you can examine the list later and identify what available tasks *can* be delegated. 

Identifying what kind of tasks are good for delegating can be tricky when you first start, which is why it’s good to track what you’re really doing all day.
    Qualities of a good task for delegating include:

    • Can be broken down into multiple, track-able steps.
    • Has a set timeline or due date.
    • Is one where your skills do not add particular value (i.e. your time should be spent maximizing your skills; delegate tasks that do not utilize your strengths)
    • Would benefit someone else from learning.
  • Start small. 

Especially if you’re nervous about handing over control to someone else, pick something relatively low stakes to start. Delegating is most effective as a long-term process, where your teammates learn and become increasingly self-sufficient in performing their tasks.
  • Create a plan before delegating.
    • Set expectations and goals for the project including timeline, deliverables, and scheduled check-ins.
    • Consider the employee’s current level of skill and responsibility, and scale the project accordingly – you can always build up over time.
    • Define objectives and consider how success will be measured.
  • Meet to discuss the project.
    • Use the opportunity to explain not just the details of the project, but what impact it will have on their career, skills, goals, etc.
    • Avoid telling them HOW to do the project; instead focus on WHAT needs to be done and WHY. Let them find the solution – after all there are very seldom *right* answers, just different ones.
    • Giving good instructions usually starts with putting yourself in the employee’s shoes.
      • What information is essential for getting started?
      • When are the deadlines, and what deliverables for each deadline? (Be specific and choose tangible milestones.  And if you are really concerned about quality, set the due dates early; that way you have time to give feedback and make adjustments)
      • What is the expected level of communication between you both during the project?
      • What is their level of authority to make decisions, or take liberty with the approach?
      • Will they be collaborating with other people?
    • Go over resources and processes for asking questions during the project.
      • Can they bring questions to you anytime or save them for scheduled check-ins?
      • Where should they go when stuck?
      • Be creative with the resources you provide. Don’t just forward pertinent emails; I find taking a video of myself doing a process is a great tool to give people. They can always refresh their knowledge by watching that rather than getting stuck or stopping to ask questions.
    • Leave time for them to ask their initial questions too.
  • Tell others about your plan and approach.
    • If someone will be accessing information or spending time outside of their normal responsibilities, give their peers and other supervisors a heads up.
    • Making stretch projects public knowledge may spark interest among others, resulting in ready volunteers for other assignments (and hey, you already put together all the instructions!).
  • Do periodic check-ins.
    • No need to go overboard, but do check in on a project (especially the first couple of times) to track progress.  Better to course correct early.
    • Use shared work documents (like Google docs) so you can check in without having to call a meeting.  I do this a lot when I am working with my assistant on writing, proofreading and research.  We can both see and comment on each other’s work while things are still in progress.
    • Keep an open mind. Delegating is about *not* running this project yourself, so bite your tongue when someone tries something you wouldn’t have. If they’re not obviously off course, let them see if through (they’ll learn more, and you might too!).

Never tell people how to do things. Tell them what to do and they will surprise you with their ingenuity.”  –General George Smith Patton, Jr.

  • Give feedback.  Giving feedback is tough.Your employee most likely wants to please you, and if you have to critique their performance, you want to do so in a way that causes improvement but doesn’t damage your relationship.
    • Be direct and timely. Make sure they are aware what’s not working and how to move forward.
    • Match criticisms with compliments. Follow up a negative with a positive; it makes the information easier to absorb and keeps spirits up.  Although be wary – people register negative feedback much more strongly than positive so applaud progress and good work too.
    • Give a personal example. Did you struggle with this project when you were handling it? Relate your experiences to build trust and understanding.
    • Focus on the work, not the person. Focus the conversation on how work can be improved, not how the person doing the work has failed.
  • Resist the urge to tell them how to do the project.
    • A good strategy is to require them to come up with possible solutions before you will advise. Even if you don’t use their solutions, it will be good practice for them being autonomous and resourceful.
    • If they are off track, keep as much of their work as possible.
    • Empower them by not scraping the project (even if you want to).  Instead of eliminating everything they’ve done (even if a lot of it was wrong), offer suggestions to get the project back on course.
    • Never give feedback publicly (i.e. In a meeting with other team members. Feedback should be constructive, not humiliating.
  • Recognize their successes. Be accountable for mistakes.
    “Never take credit, always take the blame.”

    • Delegating is not really about giving up control; it’s about guiding your employee to enhancing his or her own skills. So when a project fails, it is not out of your hands and shouldn’t be treated as such. Stand up as the leader of your team and acknowledge the problems as your responsibility too.
    • Similarly, you can take some of the credit for your part in a successful project done by an employee – but you need to recognize their work too. Publicly acknowledge their good work – it makes them feel good and reflects positively on you too.
    • Even if people make mistakes, don’t stop investing in them.
  • Repeat.
    • Good delegating is never done.
    • Always be teaching others something new. Always be looking for someone who can step up to a challenge.


Delegating can be a bit of work at first. It’s a front-heavy process; though it takes some planning to begin with, the more you delegate to your team, the less and less you’ll need to spend time pre-planning projects and meeting with them to answer questions.

Good delegators make expectations clear to their team, and a good team will learn to predict expected of them, so the flow of work between manager and employee becomes increasingly seamless. In the long run, being a good delegator will repay you again and again.

If you have other tips or tricks – please leave them in the comments.

Source: Michael Lamonsoff of the law offices of Michael S. Lamonsoff.

And since you read this far, here is a big secret:

Learning to delegate is the key to my success. People have asked how to I manage to blog regularly, compile a newsletter, work really hard at my job, speak at conferences, etc. and the truth is I have a lot of help.  There isn’t a task on that list above that I do alone – even writing this blog post.

[December 3, 2012 – also check out this post called Guide to Effective Delegating (For Control Freaks)  which has more helpful advice]
Thank you, Kate S – I honestly couldn’t do everything I do without your help.

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