A super thrilling recap of how I work plan in my ever-evolving role

Sarcasm aside, work planning is a necessary evil that has huge impact on my success at work. It's also something I've iterated on over the past few years – read on for some of my tips and tricks.

Hi everyone! I’ve been quiet over the past two weeks while I was on vacation in Europe – I hope that gave those of you who strive to be inbox zero a chance to catch up on prior weeks’ newsletters! This vacation was the first time in a while that I went laptop-less while traveling. It was a bit scary to get out the door but really gave me a chance to fully unplug. I think I got a few days into vacation before remembering that work existed… (I even deleted Slack from my phone and logged out of my work email.)

This vacation blip aside, I’ll be doing newsletters every two weeks going forward now that I’ve gathered some momentum since starting in March!

Without further ado, I’ll dive into this week’s topic. I’m excited to share more about how I work plan in a role with a lot of flexibility in order to set myself up for success. If you’re new to the blog and looking for context, I’ve written a bit about my role before here.

How I work best and how this fits into startup life 

I am someone who enjoys being organized. I thrive when I have a clear to do list and can just sit down, uninterrupted, and tackle that list. When I don’t have that, I can also be efficient but I operate on much more of a last-in-first-out process, where recency bias is strong and I will get distracted by the latest ask and forget everything else I needed to do. In a startup environment, sometimes, this last-in-first-out process works…but for the most part, I have found that to be more stressful and chaotic, and overall typically biased in favour of short-term priorities, which leaves long-term goals out in the cold. 

I’ve gone through periods of just embracing the chaos and doing whatever is thrown my way versus trying to be more intentional and focused with what I’m working on. We just kicked off our Q2 in the beginning of May and for the first two weeks of May, I made it a priority to set myself up for success with my goals for this new quarter with work planning. 

As it happened, I had a lot of travel in early May. I love to use flights for quiet focus time and often opt to go without wifi to preserve the quiet. On one particular flight, I spent half an hour planning out my quarter, going through a process that I’ll outline below.

I started with an intended split of time across my areas of responsibility

Most recently, I have been thinking about my role in three distinct parts:

1. Strategy for TestBox’s Marketplace business

2. Ad hoc support for different business areas. Currently, this is running our Customer Success function 

3. Ops for the company (including finance and my other responsibilities as an exec)

My ideal split is to spend 40% of my time on #1, 35% or so on #2 and 25% or so on #3.

Next, I referred back to my OKRs, quarterly goals, and key projects/initiatives  

At the end of each quarter, each team sets their own goals, which roll up to 1-2 OKRs for the year that each team owns. In addition to setting goals, we also lay out key projects and initiatives that we will take on in the upcoming quarter. Then, we share this out with the rest of the team at a quarterly kickoff. 

As someone who sits across a few teams (and isn’t part of one specific team), I typically focus on projects and initiatives rather than the goals, since they usually roll up nicely into the full team’s broader OKRs. As I reviewed my projects and initiatives, I mapped out the relative priorities for each project/initiative.  

Here is a messy first draft of my plan for the quarter.

I divided the page up by the three distinct parts of my role so that at a glance, I could sense check if I’m going to be well balanced based on how much time I want to spend on each area. 

You can see that there’s a lot in the first section, a good amount in the second, and significantly less in the third. I’m hoping this bodes well for sticking to my desired time allocations. 

To get to this plan:

1. I started by plotting the projects and initiatives that are time sensitive. Examples include hiring someone to join our customer success team (more here if you want to work with me or if you know someone who might be interested!), my AI projects for Marketplace, onboarding new TestBox customers, and kicking off with our DEIB advisor.

2. After that, I tried to space out projects based on if they would be one-and-done (e.g. “Improve xxxx process”) or if they require multiple touchpoints every few weeks (e.g. “podcast blast” and “gather interest data”). Truly ongoing tasks got a full row for the entire quarter meaning I’m doing those things every week. 

A little bit more insight into my ongoing, recurring weekly tasks

Depending on your job role, you may or may not have recurring weekly tasks like I do. Currently, my recurring weekly tasks include:

For Marketplace

• Emailing our users to offer support and answering questions 

• Tracking user stats by product and category 

For Customer Success

• Enabling reps in 1:1 and group sessions 

• Tracking usage stats and sending shout outs to top users and emailing low usage reps to offer enablement 

• Sending weekly kickoff emails to our customers so they know what’s happening as we onboard them 

For Ops 

• Monitoring our bank account

• Paying invoices

• Managing AR 

• Approving expenses 

If I may say so myself, this is quite the list of recurring tasks.

At first, it was really overwhelming because it felt like they could take up the whole week. I quickly figured out to set up dedicated recurring blocks of time on my calendar for sitting down and tackling these, one chunk at a time. Typically I like to do all the Ops tasks on one day in an hour long block. I prefer to offset that with the days when I do the Marketplace and Customer Success tasks since they’re quite different. Setting recurring blocks has made it easy to not forget anything, have dedicated headspace, and avoid the sense of whiplash between tasks. 

I have a page like this that I keep on my desk (and in my backpack with me when I travel…seriously…) for reference if I ever get confused. 

Turning all of this into sprint goals (working on the 1-2 week level)

By the time I’ve laid out my quarter, I also basically have my plan at the every-two-weeks level. This makes it really easy for me to plan my sprints. I usually just quickly transpose my Gantt chart into my goals for the sprint, which we share across the full team. I love having the high level already mapped out, which gives me comfort that I can achieve all my goals for the quarter while also not overwhelming myself at any one point in time. It also means that if I have a particularly busy week outside of work or know I’ll be traveling/OOO, I can frontload more work before that and make sure to stay on track. 

Finally, some scattered other thoughts on work planning:

• I’ve been wondering if I can focus on one of the three areas of my role for a week at a time – at the moment, there are a lot of recurring weekly tasks so this is tricky, but I think there’s a world where I can dedicate 2-3 days per week to one area of work (e.g. marketplace one week and then customer success the next) and leave the other few days for the recurring weekly tasks 

• Alternatively, I’ve been debating if I should have dedicated days to different areas of my work. Unfortunately, so far my experience has been that this isn’t super realistic given that customer needs fall throughout the week at random, but once I transition into managing our new Customer Success hire, this may be possible 

• I’ve also considered mapping my work to my period cycle! There are some fascinating articles (e.g. this and this) on when I’m supposedly going to be better at creative tasks versus more rote work, as one example. I haven’t tried it yet but am very curious to keep reading up on this and see if there are good opportunities to plan my work accordingly