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Mastering One-on-Ones: A Manager's Guide to Tracking and Planning Employee Development

My sister Jen had this ornery streak in her. As the oldest and Chief Bossy Pants Sister, I delegated (ahem) to the younger siblings. Every week, we had to polish our shoes, and I had the great idea of having Jen polish mine as well as hers. Put a pin in that thought for a sec. 

Meanwhile, we had these chunky lip balms called Lip Smackers that came in fun flavors like strawberry, cherry, and cola. I loved my Buster Brown shoes. And I loved my cherry Lip Smacker. And I loved the idea of getting Jen to polish my shoes! I gave her a task and set her to it. However, when I got my shoes back, they smelled like strawberries. They looked… odd. And when I put them on, I slipped like the floors were made of bananas and eels. Turns out Jen polished my shoes with Lip Smackers. And being a highly motivated "direct report” (DR), she polished the tops and the bottoms. With Lip Smackers. 

Here's my folly: I never set any expectations. I didn't tell her what to polish them with and where. And I certainly didn't tell her how to do it. But, worst of all, she polished her shoes with Lip Smackers. Not only did my attempt at delegation fail, but so did my attempt at management. And she did all of this polishing with my Lip Smackers. Not hers. Fun fact: You can't get lip balm off the bottom of your shoes, no matter how much you walk. And slip. 

As a manager, your role extends beyond overseeing your team's day-to-day tasks. You're responsible for their growth and development and ensuring that they excel in their roles. Even if your agency doesn't set specific employee goals, as a manager, tracking various aspects of your team's progress is crucial. Are they learning? Are they developing new skills? Where are their strengths, and where do they face challenges? One-on-one meetings, often called O3s, can be a powerful tool to facilitate this process.

Establishing Strong Foundations with One-on-Ones

Imagine your one-on-one (O3) meetings as a roadmap to success. I like the way Manager Tools suggests: First, discuss your Direct Report’s (DR’s) needs and aspirations. After that, you can address your needs. And finally,  expectations and explore their career development from there. It seems simple, right? But sometimes, these sessions can take an unexpected turn, veering off into unproductive territory.

The Shift from Productive to Ineffectual

One-on-ones (O3s) always start out awesome. You're talking about stuff, bouncing great ideas, making commitments… SCREECH. Wait, what? What did I just make a… commitment? What did I say I would do? What did they say that they were going to do? Here's a pothole: O3s can quickly transform from productive discussions into time-consuming "jam sessions" or, even worse, venting sessions. It's all too common for commitments to be made without clear accountability. The result? Lost time, lack of progress, and disconnection between you and your DR. So, what's the antidote to this issue? Tracking. But wait! Please don't leave. Hear me out…

The Importance of Tracking and Planning:

Accountability thrives on tracking, and tracking thrives on planning. While it might sound daunting, trust me: planning is a muscle that strengthens over time. Start by using project management software, preferably in a Kanban style. Platforms like Asana or Trello work great for structuring your tracking system.

Creating a Tracking Framework:

Here's a suggested framework of columns to set up in your software:

Reference

  • A place for quick reference items like links to mentoring metrics trackers or other essential documents.

Backlog

  • An area to jot down items that are currently non-actionable but will be actionable at a later date. This is for ideas you don't want to forget.

Individual Tasks

  • A spot for non-project-related items, such as a one-off asks. For example: you request your DR to share a guidance document before your next O3 meeting.

6-Month Goals

  • Record the team workshop goals assigned to your direct report (and even to you - sharing is caring, and you're a part of this team).

  • Could include milestones from larger projects where your DR is involved.

Individual Goals

  • Document mentor metrics bucket goals (will discuss next article) discussed with your direct report.

  • Clearly define plans and have them accessibly documented.

  • Store past plans in the Reference section for future assessments.

  • Example: "Char will focus on QC and Innovation for a set duration, maintaining Project Maintenance, Client Services, and Information Sharing buckets for now."

Example of what a tracking framework could look like. I am using Todoist for this example.

Discuss at Weekly

  • Slot to note topics for weekly discussions, from monthly mentor metrics to challenges needing resolution.

Help Me Now

  • Assign tasks with dates for urgent discussions.

Fostering Ownership and Accountability

Sharing this tracking board with your direct report (DR) helps divide the accountability responsibility. After years of working with direct reports, I realized that the manager often becomes the de facto project manager for their DR's employee goals. This dynamic can breed resentment on both ends. To cultivate leadership skills, now is the time to guide your direct reports to take charge of their future. Encourage them to plan and track their goals. This ownership is an invaluable teaching opportunity.

The Planning Process:

  1. Share the tracking board privately with your DR.

  2. Collaboratively add both team and individual goals.

  3. Invite your DR to list their goals and plan:

    1. Brainstorm milestones for each goal.

      1. Tip: Most people are poor planners, so generally what they consider steps/tasks are actually milestones. For example: "Complete the first draft of the training document" is a milestone, not a task

    2. Break down tasks for the first milestone.

      1. Using the "Complete first draft of training doc" milestone mentioned above, the tasks could be: brainstorm; interview stakeholders for what their needs are; have the document proofed; create a presentation for the document; schedule presentation to top stakeholder

    3. Here's my "smarty-pants" innovation: plans change and must be flexible. I only create tasks for the milestone that I'm currently working on. Once you complete a milestone, then map tasks for the next one.

    4. Set an end date and reverse-engineer the dates for the milestones (and tasks for your active milestone).

Embracing Imperfect Plans

Voila. We have a plan and we have a schedule. But expect that it will be almost entirely "wrong." And that's the beauty: This is another teachable opportunity. Planning is hard, but over time it gets easier. It's a muscle that you develop through practice. Milestones will be challenging to suss out at first. The tasks needed to accomplish each milestone will be a mixture of too many or not enough. And the schedule? That will be a hot mess. But next thing you know, you'll be creating these artifacts in your sleep. And with greater and greater accuracy.

I will let you in on my secret: Nothing ever goes entirely according to a plan. I never expect it will. A plan is an effective device for deeply understanding:

  • What your project is

  • What is needed to complete it

  • And a way to set priorities.

Things change during a plan, but if you know what's needed, what can be shed in an emergency, and when everything is due, a plan gives you the most flexibility. Plans shouldn't be about rigidity. They are about having all the information you need to be flexible and adapt to ever-changing needs.

Becoming an effective manager means getting comfortable with the fact that this is a journey. It’s a brand new step in your career and it may hurt to move from being an awesome individual contributor to what amounts to starting over. But it’s a journey filled with growth and learning. One-on-ones are your gateway to nurturing this growth by focusing on your team's potential. Through tracking and planning, you can ensure accountability and empower your direct reports to take charge of their own development. Embrace the journey of planning, recognizing that while plans may shift, their value lies in enabling flexibility and adaptation to ever-evolving needs. And know it’s inevitable that, at some point during this journey, your shoes will smell like cherry Lip Smackers.

Charlotte Markward