Managing Overwhelm: Part 2 Outside-In

(Calendar Overhaul)

Overwhelm is something we all experience at times, although almost all of my clients experience it acutely at this time of year with the compression of the Holidays, wrapping up their goals for the year, and planning for the new cycle. It is why this two-part series (click here for Part 1) is particularly apropos right now.

Overwhelm comes in many shapes and sizes, and generally falls into two buckets: 

  1. “Inside-out”, which I wrote about in the last post. The metaphor for this is the oxygen mask on the airplane – identifying what you need to be your best self and taking action to put that oxygen mask on yourself before everyone else around you. 
  2. Outside-in”, which is multifaceted and focuses on how you navigate and engage with stakeholders, requests and deliverables outside yourself. The biggest areas that consistently surface are in time management (sounds so rudimentary, right?) and setting clear boundaries (making powerful requests, recontracting commitments, saying no). Today’s post will focus on how we manage our time and priorities.

Most people report feeling they have no “white space” or buffer time. They feel their calendar (and life!) are not their own, they have almost no time or space to think, and incessant distractions from others (Do you have a minute? Can you please look at this in the next five minutes and provide thoughtful input?) or themselves (one word – notifications!) prevent space to think, focus and act strategically. A client just mentioned she was looking forward to vacation so she could “have my brain to myself.”

This is a great time of year for a calendar overhaul.

A client of mine and I were meeting this time last year. She had just received a promotion to lead a team where she no longer had deep expertise and needed to assess, reorg, recruit and build a high performing team and extend her stakeholder impact. 

At that December breakfast, her first obstacle was time. No time to think, create, or focus, resulting in anxiety and overwhelm. 

Identify your “oxygen mask”

We started by identifying her “oxygen mask” or her Inside-Out areas (from Part 1) that needed attention. Within a week she had a Peloton, buy-in from her spouse on her schedule and a personal commitment to do what was necessary to be her best self. One day this year at 3pm she was eating her “dinner” during a call, because she was exercising on the way home and was committed to not skipping dinner, as she might have done in the past.

Calendar Overhaul

Next, we conducted a “Calendar Overhaul.” We looked at her calendar, which felt like a sinking boat. I think of this as “right-sizing her leadership.” 

First, we emptied out all commitments as of Jan 1 and she thoughtfully added back in the “must-haves”. This included stakeholder meetings and other non-negotiable commitments. 

Then, she thoughtfully added in the necessary blocks:

  • Time with herself: Monday morning, Friday afternoon, during the week to focus strategically, etc. 
  • Time with others: direct reports, recruiting interviews, key stakeholders (we made a list of the fewest, critical people), etc.

Lastly, she analyzed her current calendar for clues: 1) She was spending too much time in meetings where she was unclear about her purpose / role of being there or accepting invites that weren’t a priority 2) She was not spending enough time recruiting (her #1 priority) and 3) she had no time allocated with herself. 

Her assistant had no criteria for decision making with her meeting requests and was adding unnecessary meetings or, she was challenging my client not to accept meetings that my client told her assistant to say yes to anyway, thus overriding her.  

(This is very common – notice your FOMO – fear of missing out – not being included, not wanting to say no, or your lack of trust in others.  These are the biggest reasons for accepting requests when they’re not mission critical).

When we recently met (after one year of coaching), she told me – I feel fantastic, I have energy! I’m taking a long break over the holidays and am excited to unplug. And she was having an even bigger impact on her team and the company as a result.  

She called this year’s reflection process her “dynamic prioritization” (brilliant!) and sent a picture of her updated calendar strategy that you can see at the top of this post. She plans to color coordinate her meetings so she can visually see where she is spending time and where to continue to tweak. 

Simple Steps to Make this Happen

You, too, can overhaul your calendar and “right-size your leadership.” Here are 3 simple steps to bailing the water out of the boat and restocking it, thoughtfully.

  1. Set aside reflection time. This can be hard to do alone. This is why many leaders get coaching! If you can’t schedule time with someone to do this, then schedule it with yourself. Start with one focused hour to begin.
  2. Start with a clean slate and add back, with discernment. Pretend your calendar is empty for January. Identify the blocks you need most for yourself (include inside-out elements such as exercise or time to think or do email and block time for yourself during the day). Then, add in the must-haves. You might feel weekly meetings with all directs are critical – challenge those assumptions and get a reality-check from a colleague or coach on what makes the most sense. You might need that with some, but not all, reports, for example.
  3. Renegotiate. This starts with identifying criteria, and then aligning with your assistant on them. You might also need to renegotiate with stakeholders. I had a Finance client who sat in on all of his partners LT meetings and needed to meet one-by-one to renegotiate what partnership would look like. This also includes setting boundaries for yourself! I have heard plenty of leaders without families admit they wish they had the “good excuse” to pick up kids. Make up your own version of your “non-negotiable toddler pickup”! One Colorado client’s reframe – skiing one afternoon a week became his “toddler pickup.”

Remember … we are all in practice. Don’t let perfect be the enemy of the good. 

If you would like to have a conversation about how to manage your overwhelm, or share what you got from this article, I would love to hear from you.

Yours in practice,


If you are interested in exploring whether we are a good fit to help you and your organization, contact us for a complimentary discovery conversation.

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