90 Day Training Wheels: Establishing a Routine on Day One
Me, by me.

90 Day Training Wheels: Establishing a Routine on Day One

When entering a new company or role with new teams, technologies, organizational structures, and systems, I have found that the deluge of information can be crippling without a process to manage the intake and iterate an understanding of the bigger picture. I developed this process for myself and have organically refined it over the last decade of my?#career .?

The result serves as a set of "training wheels" that has helped me get up to speed in an unfamiliar situation to pivot from "fish out of water" into strategic execution in under 90 days, chosen to align with most?#90days ?onboarding objectives.

As with literal training wheels, once a level of comfort and competency is achieved, the wheels slowly fade away, allowing a person to pedal without the need for deliberate focus. The elements that prove valuable in day-to-day work get absorbed into a routine, while the rest can be discarded when no longer needed.

In Part 1 here, I focus on getting through the very first day with intent while building the concepts of?#ProgressiveElaboration ?as a core routine.

Objectives of the Process

For simplicity's sake, the center of this process is an intentional system of progressive elaboration targeted at establishing foundational knowledge and objective planning.?

For those unfamiliar with the concept of progressive elaboration, it is a core element of project management that seeks to continuously improve a plan as information becomes more detailed and accurate over time. In straightforward terms, progressive elaboration is the art of building and refining over time by continuously revisiting and iterating something. In this process, progressive elaboration establishes and continuously refines the most important project of all - You.

Under this structured routine, an individual increases the horizons of capability at the same rate knowledge increases, thereby ensuring a solid foundation to pivot from tactical to strategic execution.

Core Rules of the 90-Day Training Wheels

  1. Plan:?Start every cycle with planning
  2. Document:?Write everything down
  3. Reflect:?End every cycle with retrospection
  4. Iterate Your Horizons:?Maintain focus on the now and the next while expanding your scope

Of these rules, number 4 is the most transformational once you realize that "now" and "next" are definitions of scope that increase proportionally with comfort. Your comfort in understanding what needs to be done next is a very different concept on day 1 of a new situation compared to day 90. The way to make that leap intentional is through structured, progressive elaboration.?

Day 1

With a healthy measure of apprehension, your first day at any new company or role can alternate between terrifying and exciting from moment to moment. You may be enrolling in benefits, struggling to learn where documents are stored, fighting with new IT systems, and stumbling through new organizational hierarchies all before lunchtime. So take a breath, and start with Rule 1.

Rule 1 - Plan: Start every cycle with planning

For Day 1, your only objective is to get to the end of the day while gathering as much information as possible; therefore, surviving the day is your only plan. You may have been hired to learn a new function, transform a team, implement a new tool or process, or lead a whole organization. Still, those objectives are unlikely to be obtainable on your first day, so temper your expectations for accomplishments. Don't fret; we will revisit this rule in detail in the second part of this series. For now, you only need to focus on what you can learn, which brings us to:

Rule 2 - Document: Write everything down

You may be the type of person with a photographic memory, have the worst handwriting imaginable, or prefer to type, but it's essential at the start to have a pad of paper and a handful of working pens.?

Tony Fadell ?strongly suggested sticking with paper in his book "Build ", and I couldn't agree more. Using traditional paper and pen encourages you to focus on context and conversation over the distraction of technology.

If the person doing your onboarding introduces themselves, write their name down. If they mention how long they've been with the company, write it down. If they casually drop some acronym you don't recognize, write it down. You don't need complete sentences, fully contextualized with an understanding of the big picture; your only goal is to capture as much information as possible so you may digest it later. If you need to learn what something means, write it down. If you completely understand what something means, write that down too. Again, you are working to build a habit.

Naturally, your documentation may be robust and verbose, only to become disjointed and halting as the day progresses, but this is all part of your mind calibrating to a new environment. Your information capture should be unfiltered and judgment-free, as we will be using a process to digest and refine these notes at the end of the day.

Once you make it to the end of that first day, you might be ready to kick off with a cocktail or celebratory dinner, but it's essential to reserve at least 20 minutes at the end of the day for Rule 3.

Rule 3 - Reflect: End every cycle with retrospection

You started Day 1 knowing almost nothing, but you ended with a pile of notes and some knowledge. Congratulations! Now you need to document those unstructured notes with some organization and context.

Ideally, you have a computer and a productivity suite such as Google Docs or Microsoft Word. The flavor of software is not important, but the process of translating your notes into a structured information system is critical.

Start a blank document. If your software supports a table of contents, insert it at the top of the page and get familiar with using headings and sub-headings to keep the table of contents structured and logical. Leverage headings to group knowledge into appropriate categories, with subheadings, further refining broad categories into smaller sections. The specific heading titles are yours to define as they align with your role but broadly can be organized into technology, process, and people.?

As an example, the table of contents for my 90-Day Book of Knowledge that I created when onboarding at?Medallia ?looked something like this after my first 90 days:

  • Technology and Market
  • Platform
  • Team Notes
  • General Wisdom
  • Sales Processes
  • Professional Services
  • All Things Tech Stack
  • Who's Who in the Zoo
  • Open Questions
  • Appendix of Useful Links

The structure you choose and how it evolves is only important to you, so feel free to organize it according to the way your role demands.

Once you have your document established, take the time to re-read your notes one by one and transfer them into your document. They can become bulleted lists or narrative paragraphs. Still, you want to translate every piece of information you wrote down into an appropriate section and any additional context you've gathered.?

People you met and details about them can go into "Who's Who." Technology systems can go into "Technology" at first, intending to subdivide and expand them as you learn more. Finally, information that is unclear or necessitates further understanding can go into a "Things to Learn" section. These will be items you will regularly revisit to reconsider, contextualize, and refine over time. You will discover many "Ah Ha!" moments where a disjointed or unclear piece of information is suddenly illuminated with context and meaning, so don't skip any of them unless you're sure they are garbage.

Follow this until you've digested, transcribed, and translated all the notes into your document. You are implementing a personal retrospective or lessons-learned exercise, but instead of focusing on a project or team effort, you're performing this retrospective on yourself. What did you learn today? What does that information tell you about how you need to adjust tomorrow and in the future? As you shape up the puzzle in front of you, where are the giant holes in your information that you need to explore further? Take the time to ponder the big picture and accept that you may not have revelations at this very moment, but you're establishing the framework to discover them later.

As a final step, remember to save that document, then throw your notes away. Yes, toss them into your recycling bin and enjoy that dinner or cocktail. This step is a crucial part of what makes this process successful. The notes you capture during this process's early phases should only be a holding tank until you have time to translate and contextualize them into your book of knowledge. Once that is done, they have served their purpose and can be discarded.

You may be tempted to jump right into planning your second day, brimming with excitement, but that would get you ahead of your skis and violate Rule 4 - "Iterate your Horizons". As stated before, your plan for Day 1 was to make it to the end of Day 1, so go ahead and enjoy that dinner or cocktail and celebrate success.

In the second part of this series, I will focus on Day 2 ?where you create your first plan and reiterate the entire cycle. We are incrementally building towards expanding the horizons of what is needed now and next, so I hope to see you in the next installment.


If you have a process for ramping up quickly in unfamiliar situations, share a comment or link, as I'm always looking to refine my own tactics and assumptions. The beauty of progressive elaboration is that it never ends!

This seems too good. Will await for upcoming posts

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