💙*Why* is it SO freaking hard to delegate?

Hello and Happy Thursday!

Today's newsletter topic is (selfishly) one that I personally wanted to know more about. The business has been growing at an extraordinary rate over the last six months - something I am incredibly grateful for after a slow 2023! That said, such quick growth has put one of my weaknesses front and center: delegation.

I feel fairly confident stating that I'm not alone in this.

So, what makes delegation so freaking hard for so many of us?!

Is it that, culturally, we continue to celebrate overworking?

Or that we continue to fall back on "being too busy" to delegate?

Are we all just collectively working through the same trust issues?!Regardless of why we struggle, today's issue is all about practical, actionable ways to flex your delegation muscle. I'll be putting in the reps myself and look forward to sharing what I learn in a future issue!

Yours (as soon as I hand it off to you),

Jill

Let's delegate!

We’ve all been there.

 There’s a task or responsibility that has been chewing away at your focus, your peace, or your motivation. Perhaps as your role or work has evolved, this task just isn't relevant to the core of what you do anymore. Perhaps it’s something you’ve never been very strong at, and you dread it. Perhaps it’s easy-peasy-lemon-squeezy, but just menial or redundant enough to fully throw off your workflow on the day you have to address it.

Whatever it is, you want it gone. You already know who would be better positioned to take it on. You think through how you can shift the responsibility, and then for whatever reason, you begrudgingly think, “ugh, it would just be easier if I keep doing this one.”

Such is the paradox of delegation. We know that, when done effectively, it’s a tide-riser. But when the rubber meets the road, it just feels like a massive drag. I’ve got some theories as to why that may be.

Here are my 5 theories on why we don’t delegate:

Theory 1: we don’t have time

I know this is a big one for me. If you offered me a dollar to list the tasks that I should be handing off, I’d have enough to treat us both to a fancy dinner in no time flat. But where oh where am I - the busy person saddled with all these tasks - supposed to find the time to map out the upskilling, process handoff, access, training, and follow up support necessary to delegate well? Where are any of us supposed to find the time?

Theory 2: there’s no documented process in place

We all have ‘em. Those beautiful, fully intuitive processes that we’ve honed to a science. They work, they’re efficient, they’re effective…and they live entirely in our own heads. Without documented process in place, even the most well-oiled processes and workflows turn into a complicated communications and training exercise. Think about it: how many times have you thought “it all lives in my head, there’s too much to translate?”

Theory 3: we’re not all executive function rockstars

No two brains are built the same. If we’re stressed, not physically feeling our best, learning or processing a lot, or navigate the world with any one of several flavors of neurodivergence (🙋‍♀️!), executive functioning might not be our strong suit. And - truly - that is okay! But it does mean that calling on working memory, self control, cognitive flexibility, and a whole host of other skill sets necessary to get through certain tasks can be trickier than expected. 

Theory 4: there’s always something more urgent

Oof, this one really hits home for me. I know I’m not the only one with a miles long list of all the important, juicy, meaningful, impactful work I’d like to do - including some serious delegating. Sadly, it feels like there’s always something that has to happen first. Whether it’s timely, easier to crank out first, or needed to mitigate an icky outcome, it seems like there’s always a more urgent task calling me away from what I know is important.

Theory 5: we’ve got some trust stuff to sort through

Whatever the task at hand is, it’s been yours for a while. Even if you’re eager to offload it, you still want it well cared for, and you want the work done well. And maybe - just maybe - you don’t trust another person or team to handle it as well as you have, or in the same way. 

Okay, so how do we get past this?

Perhaps one of my five theories above struck a little close to home. Perhaps more than one of them did, and that’s okay too! In any case, now that we have a handle on why we may struggle to delegate, let’s talk about how to move from there to action.

Step 1. Check in with yourself

In the moment when you stop yourself from moving forward with delegation, take a beat to self-reflect. What is it that's actually stopping you from delegating? Is it a time crunch? A trust deficit? Is maintaining the responsibility a point of pride? Check in with yourself each time you hesitate to delegate and see if it's one of these things. Even if all you learn is your biggest “why” for choosing not to delegate, you’ll have a better understanding of what you need to move past it.

Step 2. Check in with your team

Deeply understanding your team - their strengths, weaknesses, and developmental goals - will only serve you in your capacity to effectively delegate responsibilities to them. Perhaps knowing you could help a teammate move closer to a career goal by means of taking on the task in question is just the thing you need to move past your blockers. Not sure where to start getting a sense of where your team is at? Borrow some questions from us!

• What are your current priorities and workload?

• Which tasks do you feel most confident handling?

• Are there any projects you’d really like to work on if you were given the opportunity?

• Are there any specific areas or skills you’re looking to develop?

• What resources or support do you need to successfully grow in these skills?

• Are there any tasks you feel are not the best use of your time?

Step 3. Document, document, document!

To avoid the “I don’t have time for this” problem, the best time to start documenting your work and processes is on your first day in the role. The good news is that the second best time is today! Having well documented systems and processes means that transitioning knowledge and learning material can be as easy as guiding folks to the right pre-existing resources, which helps democratize information, enable better collaboration, speed up learning and onboarding, and save loads and loads of time. 

It’s a big lift, but the good news is there are loads of awesome resources out there. Tools like Loom and Scribe can help turn you into the training content designer you never knew you could be (bonus: they’re amazing for enabling distributed, asynchronous work!). And between Google Drive, Notion, or a whole host of note-taking apps, anybody can find a place to document and store their sources of truth.

🚨Resource alert!🚨Not sold on the case for documentation? Check out my below shoutout to Podge Thomas in today’s “Stuff We’re Loving!”

Step 4. Get clear on what success looks like.

It could very well be that we don’t fully appreciate the impact of past delegation because we never assessed its success! Create a “definition of success” to define the best outcome for anything you consider delegating - this can include what success looks like for the person taking over the task and for you! Sometimes, seeing the potential reward for the handoff may be just the push we need to make it happen.

The case for prioritizing delegation:

I'm guessing we share a dream for our future life - the one in which we’ve effectively delegated appropriate tasks to the right folks and can now prioritize our most meaningful work. But just in case you’re not yet convinced of the power of delegation, let me remind you what’s on the other side:

• A more manageable workload: this one’s pretty straightforward, but when you offload some of your “timesucks”, you get that time back!

• Development and leadership opportunities: often overlooked, this is such a powerful motivator for managers to learn effective delegation. Your team is hungry for growth and development, and finding some (appropriate) leadership responsibilities for individuals to take on is a great way to increase their confidence while reducing your stress.

• Recognition, acknowledgement, and trust-building: don’t underestimate how much other folks can rise to the occasion when thoughtfully delegated a new responsibility. These opportunities to acknowledge, appreciate, and recognize someone’s growing scope are huge when it comes to the culture on your team. Trust your teammates to do the work, provide the resources they need to understand it, and let yourself be surprised by the outcome.

In closing…Finding the time, space, motivation, process, and wherewithal to set yourself up for effective delegation can be a doozy. Trust me, I know. But when I think of the ROI (return on investment) in all the skills one can master as a people professional, a manager, or a small business owner or leader, solid delegation just about tops every list. Put in the reflection, the time, the team understanding, and the documentation to delegate effectively now, and I promise you’ll see that time and energy granted back to you - and then some (and then some more!!) - in due time. You got this.

STUFF WE'RE LOVING

Documentation ftw: Last June I sat down with Podge Thomas to discuss the power of documentation on my podcast! To date, it's both one of my favorite episodes and one of the most downloaded. Podge does an incredible job of laying out the importance of documentation and providing a great starting point for people, regardless of role or company size.

Pro Tip: If things are moving too fast to do them yourself, hire Podge to help. I just started a four month intensive with her and her team and I'm already feeling like it's the best money I've spent in a long time. Whether for the sake of effective delegation, better process management, asynchronous enablement, Podge's documentation savviness and strategic operations experience brings an instant sense of relief when things feel beyond overwhelming.

People Ops Powerhouse: Jen Bergen knows her stuff. From new employee onboarding to knowledge management, to process and program design, she’s got you covered. Today I want to shout out her process documentation courses (she has a guided one and an on demand one!). Ready to make things easier on yourself? Check her out!

Amber with the (virtual) assist: Ready to delegate like a whiz? Trusty Oak connects you with US-based virtual assistants. It's how I hired my very first VA, who I absolutely adored! Even better? Founder Amber Gray even offers a delegation course to set you up for more meaningful success in partnership with your VA. She’s also wrapping up a free 3-part LinkedIn Live series on delegation next Thursday - take a peek and sign up!