Managing Your Time as a Middle Manager

How to allocate your time when you’re being asked to do it all

👋 Howdy! Claire here, Founder & CEO of Canopy. I’m back writing, after two weeks off (last week I ran a 40-person manager retreat onsite in Georgia, and the week prior I took a day to soak up my birthday — I turned 36!) Thanks for staying patient with me in the interim💛

Eager to now share this brand new piece I wrote below. And, to receive new writings each week in the future, be sure you’re subscribed…

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Went back to my roots as an artist, and had fun with this image.

Imagine squeezing a tube of toothpaste at both ends.

Apply enough pressure, and at some point, the what’s inside is going to explode from the middle. (Yes, not the most pleasant of mental visuals.)

Now, can you hypothesize what it might feel like to be the toothpaste tube, itself ?

As absurd of a question it might be, if you’re a leader — caught in the middle between a layer of direct reports and supervisors — you might relate to the tube of toothpaste more than you’d like to. Squeezed at both ends, with no one concerned that what’s in the middle simply isn’t going to fit.

After working with thousands of leaders, I’ve observed that most leaders feel this way. And as a CEO and small business owner myself, I’m all too familiar with this reality.

What we feel most squeezed on is our time.

Oftentimes, this tension between the two sets of tasks is referred to as being a “player-coach.” On one end, you’re expected to map out team goals, hold 1:1 meetings (the “coach” role). At the other end, you’re being asked to deliver on tactical work such as writing code, designing a feature, or creating a marketing campaign (the “player” role).

This isn’t inherently always a bad thing. Doing some of the “player” work may keep you feeling connected to what you’re passionate about. Or, perhaps, the tactical work keep your knives sharp around the latest industry trends.

What feels bad is the lived experience of it. You’re overwhelmed, never knowing if the priority you’re chasing is the right one. You’re depleted, trying to keep up with requests from all angles.

You are the toothpaste tube, squeezed from both sides. How do we reconcile this?

From my work with leaders over the past decade, here are the do’s and do not’s for how to navigate this tension well, and allocate your time in the best way possible.

First and foremost...

DO NOT: Chase balance, or believe a perfect distribution of time exists.

Balance is an illusion.

There is no magical formula for how to best distribute your time. So don’t beat yourself up that you feel like you’re not striking some “perfect mix.”

What is “best” highly depends on the context of the situation: What is required of you, your team, your organization in that moment in time.

This means...

DO: Figure out what is most high-leverage for your specific context.

Ask what would best serve the current context — and choose your allocation of time based on that context.

Some of these questions to ask yourself to help discern this:

• What is most urgent?

• What is team success most contingent on?

• What is most critical to your team and organization at this moment in time?

You might discover: You need to take a step back and nurture your team so they can adopt new processes better. Or, you may realize you need to double down fiercely on finishing your own personal deliverables first, so that the team then contribute their work around what you created.

Examine what role — “player” or “coach” — would truly be high leverage, and prepare yourself to then...

DO: Choose only 1 focus at a time, for a specific period of time.

Not two focuses, just one. Decide what role you’ll concentrate your energy on, and for what specific period of time. I call this “Fluid Focus.”

For example: Say, you’ll focus on being in the “coach” role to help your team navigate a reorg that’s happened. You set aside 1 month to focus on this. This means you intentionally will place your IC engineering work in the back seat for that 1 month.

You accept the trade and acknowledge that you’re not going to get as much (if any) progress done on coding during that 1 month and — here’s the important part — that’s okay. The “player” role of coding is something you’ll come back to.

In order to perform exceptionally well in one role, rather than subpar in both, you recognize you must pick one role to focus on at a time. And then remember, you can switch your focus later (hence, “Fluid Focus”)!

However, none of this works if you don’t communicate it.

DO NOT: Assume that you can put your head down and just get the job done.

It may seem like a great idea to you to focus on purely the “coach” role for 1 month.

But if your team happens to think that receiving your part of the code was top priority, they’re going to be confused why you haven’t shipped it yet.

And if your supervisor had a deadline for that code in mind, they’re going to believe that you dropped the ball.

This means, you’ll need to...

DO: Communicate exactly the role you’re prioritizing and why — with both your team and supervisor.

While it may seem obvious to you to prioritize a certain role, no one will know unless you tell them.

Specifically, you’ll want to detail:

• The role you’re prioritizing (“player” or “coach”)

• What period of time you’ll be prioritizing that role

• Why you’re prioritizing this role

For instance, to your team, you might say:

“For the next 3 weeks, I’m going to be shifting my priorities to focus on the creation of a new marketing campaign. As a result, we’ll pause our 1:1 meetings we have, and team check-ins. Know that it may feel like I’m more absent than usual, but it’s merely a short phase to serve our company’s overall goals. The company’s growth targets require that I knock this out now, and I’ll need focus deep work time to do so. You can expect me to come out of this phase in 3 weeks, and we’ll pick back up our 1:1 meetings again.”

And to your supervisors, you might say:

“For the next 3 weeks, I’m thinking it makes sense to shift my priorities to focus on completing the creation of the new marketing campaign — that way we can hit the deadline you intended for Q2 growth goals. Are you okay with me prioritizing this? If so, I think some of the managerial updates I usually send to you will be on pause for those 3 weeks, but happy to resume them after this phase is completed. How does that sound to you?”

For the communication to your supervisors in particular, you’re also actively asking for their input on the prioritization of the role. This ensures you’re always aligned with their expectations and not superseding what your supervisor believes to be the most critical priorities.

A few last caveats as well...

DO NOT: Underestimate the cost of context switching.

It’s little wonder we’re so tired as leaders. Context-switching consumers our energy. Studies have found in fact that 40% of productivity is lost when context-switching.

Because of this, accept that the switching of context itself is work. Build in the margin for that energy expenditure. Perhaps, for example, you place a 1 week buffer between modes as “catch up” time, where you don’t have a specific focus on “player” or “coach” role. This then gives you time to evaluate which role might be best to focus on in the next phase. Or maybe you decide to carve out a much needed break and take time off as needed.

DO NOT: Stay in 1 lane for too long... because you like it.

Be wary of your personal preferences for allocating your time as a leader. We all have a bias to a mode that’s more “fun.” For some of us, that’s relishing being a “coach,” helping our team solve problems and coaching them in their careers. For others, we’re most comfortable jamming in the deep work of our “player” role.

Either way, what we personally like is not always what the situation requires. We must be truthful with ourselves to not conflate the two.

Putting it all together

A blog post may feel nice to read on a Thursday at 10AM — but it’s of course an entirely different thing to try to put into practice.

Because of this, to help you hold all these pieces in your mind, you can distill it down into what I call the “4 Steps of Fluid Focus”...

1. Stop chasing “balance.” Commit to making a trade.

2. Choose 1 role to focus on (“player” or “coach”) and the period of time.

3. Communicate this choice to your team and to your supervisor.

4. Readjust and reassess as needed.

As you go through these four steps, you’ll likely discover an inconvenient truth: The choice isn’t obvious. In fact, it’s excruciatingly, almost impossibly hard to decide on just one role. A part of you wishes that you could “cheat” and you could just do both roles at once. Well, sure, you absolutely could!

But remind yourself of the tube of the toothpaste: The reason you’re so exhausted and displeased in the first place is because you’re squeezing yourself from both sides. You’re trying to do too many things at once.

Embrace the trade-off. Relish your freedom to be fluid in your focus. You’ll start to notice some interesting side effects…

The cognitive load of doing two roles at once will slowly be relieved. You’ll find depth in your work, not just surface area covered. And the actual output of your work you’ll find more satisfactory.

After all, you deserve a far better fate than the squeezed tube of toothpaste.

-Claire

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Looking to find more ways to be precise with your time as a leader? Here are few ways we can work together…

• 🚂 Partner with me to roll-out a leadership training program for your managers.

• 📣 Invite me to deliver team keynotes and workshops, remotely or in person.

• 🌿 Use Canopy, our lightweight leadership learning app, in your day-to-day.

• 🤝 Explore 1:1 executive coaching with me personally. (I’ve had a few spots open up for 2025 — I’ve had the privilege of coaching leaders at companies like Apple and Uber, and welcome the opportunity to share those learnings in-depth with folks one-on-one.)

I’d be honored to chat and see what might be the best fit for you. Feel free to reach out to me directly here 💚

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