Reflecting Strategically to Pivot Inertia

Be Uncomfortably in the Questions

Kathryn Maloney M.A. ABS

Kathryn, an appreciator of contrast and the exquisite beauty found in the spaces between, thrives at the dynamic intersection of system design and applied behavioral science, driving outcome-focused transformation.

With over 25 years of experience, she catalyses change by weaving visionary systems initiatives into strategic priorities. As a trusted advisor, she empowers leaders and teams to build resilient businesses and create profound impact.

Drawing on deep expertise in leadership, communication, and human systems design, Kathryn infuses presence, power, and rigor into evolutionary organisational strategies. Her approach transcends managing complexity – it’s about co-mastering context to unlock strategic potential and elevate value.

Kathryn guides organisations to navigate challenges with unwavering clarity and intent, transforming visions into lasting legacies of co-crafted innovation and evolutionary growth that align with system aspirations.

more about Kathryn

2026-03-10, Chester, MD

Live the compelling and sticky questions if you choose to be meticulously and effectively strategic.

The Commitment to Strategy

Without stopping to interrupt assumptions, disrupt apathy, illuminate bad habits, notice defaults, break the looping, interrogate 'Where are we at?', and question mindless tasking, teams get into a bit of trouble.

You should not expect someone else to do the prioritisation work for you.
Strategy, as opposed to merely operating, is now a universal job accountability.
No imaginary figure is magically delivering to you your strategic framework.
You have to build it in.

Strategy is the most base commitment of teaming and delivering. Your daily accountability and responsibilities have to directly tie to your strategic logic.

Embedding Strategy in Day-to-Day Work

By creating forcing functions to live strategy in the day-to-day, teams own outcomes much better. You want to craft the design of your workflow system to nurture and further your strategy.

Challenge yourselves to build real-time reflection.
Identify and work through what may need to stay, shift, or stop.
Dial up a conversation right now to make smart directional changes.
Confirm verbally that you are all still on the same page.

Appreciate that far tighter frames of time are now necessary to work strategy. Daily accounting for where each project and measurable outcomes lie is a good, not a bad, idea.

Convening to "group-illuminate" adds unending value.
Yes, meetings consume time; however, broken communication consumes whole businesses.

Building alternative workflow mechanics, with the help of AI, to hold the complexity and the constantly moving parts goes without saying.

To parse, distribute, and manage the execution of work amidst the non-stop change is in fact the actual rigor applied – and for elevating potentials.

Personal and Collective Responsibility

Feel more invincible to disrupt your own (complaining, non-verbal, avoidant, offended, defensive, judgmental, holier-than-thou, etc.) behavior. Ways to strategically get out of your own way are:

Say your questions out loud, without fear of judgment
Communicate your thinking so others learn, and bantering can become more comfortable
Participate in productive course-correcting as a group
Become an open and generative collective to pursue being effectively strategic
Ground in being disciplined and committed, rather than performative, operationally.

Reflexive Questions: Rudders for Anti-Inertia

Reflective Question: Counter Reflective Question
Where do we need to be more opportunistic?: Where do we need to be more steadfast?
When is urgent eclipsing important?: When is important eclipsing urgent?
What are we less confident about?: What are we more confident about?
What refreshed outcomes are we naming? For when?: What older outcomes are we letting go of? By when?
When is feedback moving too slowly?: When is feedback moving too quickly?
Where do we need to be more stubborn?: Where do we need to be less stubborn?
When did we act too quickly?: When did we act too slowly?
When are we over indexing on a specific detail?: When are we glossing over a specific detail?
When have we narrowed our focus too much?: When have we narrowed our focus too little?
What changed?: What has remained the same?
When did we get distracted, and regretted it? By what?: When did we stay focused, and regretted it? On what?
What matters less now that mattered more then?: What matters more now, that mattered less then?
Where can we benefit from hearing different perspectives?: Where do we get bogged down in navigating so many different perspectives?
When were we on autopilot, and it helped?: When did we have trouble "snapping out" of our routine(s)?
What do we need to learn on the fly?: What must we unlearn on the fly?

Living the Questions

Use reflective questions like these as some of your strategic rudders. They help with the inevitable inertia and unconscious defaults.

Feel energised by living the questions. Good, compelling questions serve to open the higher individual and group mind.

The field can then meet you in that open, evolutionary space, enabling strategic expansion, innovation, and elevation.

You’ve got this. x

Attribution

No idea where this set of questions came from originally, but they are good ones. I switched a few things around but thank you to whomever packaged them!

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This is Elevating the Game.

Published on 2026-03-10by Kathryn Maloney M.A. ABS