The 6 Step Process That Helped Us Execute On Plans Each Month

Executing on Plans / April 30, 2019 / Kristie

When you set your plans at the start of the month it feels exciting and invigorating. You have a vision of all the things you’re going to accomplish.

Then you start working on those plans and you’re super busy. You’re delegating tasks. You’re helping your team. You’re hustling every day, often putting in extra hours to push through all the work on your plate. You’re getting so much stuff done.

But before you know it… it’s the end of the month. You wonder where all the time went and why you’re not seeing the results you expected.

How could that be? You were so busy. You got so much done. You crushed so many things. You didn’t get everything done that you planned, but you were really busy. Why aren’t you seeing the fruits of your labour?

We’ve experienced this and it’s frustrating. It feels like you’re revving a bunch of engines but not moving the needle.

Here’s a step by step approach to how we solved the problem:

how we're getting better at focusing each month so we can execute on our stop priorities

Step 1: Pinpoint the problem through retrospectives

A major game changer for us was when we started doing retrospectives. A retrospective is a review and dissection of a specific time period, in this case the last month. The goal is to identify what’s working and what needs improvement so you’re better prepared moving forward. Instead of making the same mistakes over and over again, a retrospective brings awareness to issues so you can change behaviour and stop getting the same results.

How to do a retrospective:

At the end of the month we’d meet as a team and go over:

  • What was supposed to happen?
  • What went well?
  • What didn’t go well?
  • What did we learn?

Each team member was asked to come prepared to the meeting with their list of 3 things that went well and 3 things that didn’t go well.

Through doing the retrospective we’d usually uncover a few processes that needed to be tweaked, but more importantly, it became apparent that the root problem was too many things on the go without a clear definition of what success looked like. We didn’t have a clear focus, which made prioritizing a big challenge. 

We needed to be more strategic. 

Step 2: Identify the goal & your WHY

The first step towards being more strategic is to zoom out and identify the main problem you’re trying to solve and/or goal you want to achieve.

Look at the big picture and ask the following questions:

  • Where are you trying to go?
  • What are you trying to achieve?
  • Why is this goal important?
  • What’s the risk of not reaching it?

Asking these questions helps you get clarity on whether or not you’re pursuing the right goal. It also helps drive alignment. To get your team rallied around solving a problem or reaching a goal, be transparent with them about why it’s important and the impact it will have. When everyone understands why a goal is important, they’re more engaged

Step 3: Paint a clear picture of success

Once you’ve identified your goal and why it’s important, paint a clear picture of what success looks like. This way you know when you’ve achieved it. While it can be challenging to identify, having a clear metric to drive success has a big impact. It provides clarity and focus. 

To identify your metric, ask yourself the following questions:

  • How will you know if you’re on track?
  • How can you measure results?

To take it a step further, identify the leading indicators. If your goal doesn’t have an easily measurable metric to track, ask yourself:

  • What are the leading indicators that will tell you if you’re on track so you don’t have to wait until the end of the month to identify if you’ve hit the goal or not? 

For example, our marketing team’s measure of success at the end of the month is the number of trials started. Leading indicators that tell us if we’re on track or not are traffic to the website and the conversion rate from traffic to trial signup. This way we know which lever to pull and where to focus on having an impact. If we’re hitting our goal of traffic to the website but our conversion rate is lower than the goal set, that tells us we need to focus on optimizing the website and making changes to hone in our messaging. 

Step 4: Create your plan of how to get there

Once you have clarity around what success looks like, planning how to get there becomes much simpler.  

Here’s where you want to leverage your team. As a leader, a great way to help grow the intelligence and competence of your team is to identify the problems and what success looks like, then step back and let them figure out how to get there. You can help guide them by asking tough questions and debating decisions.

For example, ask your team the following questions:

  • What are the key/critical things that need to happen?
  • When do these key/critical things need to happen by?
  • What are the smaller things that need to happen and by when?

Have your team identify all the major milestones to reach the goal, then break down each milestone into the smaller steps and action items that need to happen.

Daylite Tip: We use Projects in Daylite to track the main objective that we’re trying to achieve. We then create a Task List for each major milestone and organize all the little “to-dos” by creating tasks and grouping them into the appropriate Task List. This allows us to quickly jot down all the steps and be able to drag and drop to prioritize them in order.

We also use the Daylite calendar to identify milestones. We create all-day appointments in our Daylite calendar for key events. This way, when looking at the month view, it’s easy to get an overview of deadlines and milestones approaching. Each week we can see the major milestones coming up and make sure we’re focusing on the right things to hit those.

This step is where you’ll also want to use the insights from your retrospective. People are creatures of habit so it’s important to identify when you’re about to fall into the trap of an old habit.

For us, a habit is coming up with big, complex solutions. We’ve had to build the habit of thinking in terms of bullets before cannonballs.

To make sure your plan is realistic, ask these types of questions:

  • Is this plan reasonable within the given time frame?
  • Have we made any assumptions that need to first be tested or validated on a smaller scale?

Step 5: Plan ahead for pitfalls and setbacks

This is an important step that’s often missed in planning. Contingency planning helps you and your team be proactive and put out potential fires before they start.

Go through your plan and identify potential pitfalls. Then discuss creative ways to prevent those problems from happening, or a fall-back plan of how to deal with those problems. 

For example, ask your team:

  • What are the potential risks or pitfalls that could throw our plan off track?
  • If we miss our first milestone, what do we need to do to get back on track?
  • If we miss our second milestone, what will we need to cut/do/change to get back on track?
  • What are the nice-to-have’s that can be cut in order to meet the deadline?

By identifying these pitfalls and talking through potential problems, when you run into issues, people are already prepared with how to handle them. It’s like doing a fire drill. When people know what to do in the event of a fire, they’re less likely to panic or make mistakes.

We’ve found this step of contingency planning is what makes projects run much smoother and helps us reach our goals.

Step 6: Setup a meeting rhythm

Once everyone’s clear on the goal, what needs to happen, by when, and who’s responsible, se tup a meeting rhythm. These meetings are opportunities to check in and make sure things are running smoothly.

What’s worked well for us is having:

  • Weekly meetings to identify the priorities for the week, track the metric(s) to make sure we’re on track, and discuss any bottlenecks or issues.
  • Daily 10-15 minute huddles to share whether or not we completed our top priority the day before (along with why not if we didn’t), our top priority for today, and anywhere we’re stuck so we can remove bottlenecks early on.

For a more in-depth look at how to run these meetings, check out my post on Mastering the Weekly Meeting and How Daily Huddles Help Us Execute on Plans.


Following this process and having these checks in place has helped us get better at executing on plans and reaching our goals each month. We’re more strategic and proactive about planning than we’ve ever been before. We’re not perfect, but by sticking to this process we’ve improved our track record of reaching goals month to month.

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