Monthly planning

I block out 2hrs in my calendar at the start of every month for a personal review and planning activity. It’s often tempting to skip this recurring appointment task, particular if my calendar is otherwise busy, but it’s always a worthwhile use of my time.

It’s a monthly activity specifically because it forces me to take a broader view of my work than the shorter weekly prioritisation activities, but not as broad as my semi-annual reviews.

In these monthly planning ‘meetings’ with myself, I answer a series of questions. As you will see, there are both reflective questions, and forward-looking planning questions

In the last month…

  • What have I achieved/progressed in my annual performance plan?
  • What have been the biggest highlights, wins, learnings for my team?

In the next month…

  • What will my team be delivering from our product roadmap?
  • What new knowledge or skill will I acquire/develop?
  • How can I develop my team?
  • What one thing can I work on/achieve that will make everything else better/easier going forward?

The last question always fills me with a bit of a thrill, if I can answer it. There is something incredibly inspiring and motivating in knowing that I am planning on working on something in the coming month that will deliver some kind of step change in how my team and/or I operates.

Recently for me, answers to this question have included introducing a new service management system, defining key performance indicators for my team, improving the way we communicate the prioritisation of our projects in our roadmap, and establishing regular check-ins with key stakeholders.

I recommend you try establishing a monthly planning habit.

Weekly 1:1

Do you have a short, sharp weekly check-in with each of your direct reports? I do, and I could not imagine managing others without doing something along these lines. What works for me is; keeping it regular e.g. weekly, following a consistent format i.e. a set structure, process, time, location, and making it a two-way conversation with both I and my direct reports bringing topics to discusss at the meeting.

Specifically, I like to use a Trello board for each of my direct reports to capture discussion topics in an easy format where both parties can prepare in advance, and track conversations over time. See this template –

Within that board, I like to keep a list containing both current priorities that we review each week, and longer term (e.g. annual) objectives that we look at periodically as part of each person’s ongoing development plan.

Whilst I don’t necessarily reference giving feedback as a formal part of the 1:1 structure, I do try to ensure that in each weekly discussion I provide feedback to them in some way, and solicit feedback from them about myself and my performance in my role. Normally I would do this as part of general conversation, or link it to a specific topic we are discussing.

The main benefits of regular 1:1 meetings is that it’s an opportunity to stay aligned with each other on the 3 P’s:

  1. priorities – what is the most important work we are doing
  2. progress – how are we progressing with this work
  3. performance – how are we both going in our roles, in relation to each other

More broadly, it’s also a good forum to gauge other indicators, like motivation, workload, and stress levels, answer any questions, and otherwise just build a healthy working relationship of trust and transparency with each other.

Beyond these practical management reasons, I’ve also found it be to be effective way to manage our time. Rather than a dozen short conversations or email/message threads spread through the week about various non-critical, non-urgent issues, a regular 1:1 provides a forum to discuss all these issues in a batched, focussed way. Batching small conversations together means that we free up more of our time during the week for focussed, deep work. Reserving the weeklyr 1:1 forum for any non-urgent conversations means we avoid distracting each other during the week unnecessarily.