My Seven Step Monthly Kick Off Framework

In today’s issue, I’m going to show you how to use the start of the month as a trigger to set you up for success.

You might be new to your role, or have come off the back of a stressful end of month, and the temptation is to think, “I have plenty of time, the pressure is off, this is the week I can relax a bit.”

But week one is 25% of your month. Give up this week and you put all the pressure on yourself to make it back in weeks 2-4.

Here’s a system to help you get ahead.

Step 1: Clean your calendar

We’ve fallen into a world where our calendar tells us what we are going to do today, instead of us deciding that for ourselves.

As sellers we receive a stream of invites from our managers, our colleagues, our training teams, our product teams, as well as those external invites from the webinar we signed up to or the partner awareness session.

If we wanted to we could be very busy and yet not do anything that put us in front of a customer.

The start of the month is a great opportunity to clean up your calendar and ensure the coming four weeks are focused on high value revenue generating activities.

Go through your calendar week by week and:

  • Colour code any customer facing meetings or calls green (or any colour that will stand out)

  • Ensure your prospecting time blocks are in place and have a clear description of what you need to do in each block.

  • Look for any recurring meetings set by you - can you cancel these? Are they really needed?

  • Look for any recurring meetings set by someone else - can you decline or shorten these?

  • Look for any learning or coaching sessions that are in core prospecting hours - can you ask to move these to the very start or end of the day?

By the end of this step your calendar should be clean and set you up for success this month.

Step 2: Triage your accounts

Depending on the size of your territory you might have anything from 20 - 2000 accounts in your territory.

And regardless of the size, 80% of your bookings will come from 20% of your accounts - so you need to constantly prioritise and re-prioritise who those 20% are.

You should have triaged your territory at the start of the year - based on existing relationships, what you know about the industry, and where you think the best opportunity is.

But things change. Companies get acquired. You might have sold to a key company in that territory. You may have learned that an account has just purchased from a competitor.

Use the start of the month to re-prioritise your territory and ensure that you are confident that your top 20% are still the top 20% to focus on.

Step 3: Check earnings reports

If you are selling into public companies, then every 12 weeks they are required to publish their quarterly earnings for investors.

This normally includes a recorded webcast (normally presented by the CEO and CFO), a PDF of the presentation, and a PDF of the earnings tables - Profit and Loss, Balance Sheet and Cash Flow Statement.

These documents can be a goldmine of information, giving the companies up to date view on their performance, challenges they are facing and their priorities for the future.

For companies that follow a calendar financial year (Jan-Dec) they will normally publish on this schedule:

  • Q1: around 20th April

  • Q2: around 20th July

  • Q3: around 20th October

  • Full Year: Around 20th January

If you sell into private companies, then although they are not required to disclose their quarterly or annual results take a look at their news pages as if things are going well they’ll often publish a “good news” story.

Step 4: Check careers pages

For your priority accounts, careers pages can be another great source of information about the priorities your customer is focused on.

Specifically look for senior leadership and management roles as these will give you an idea of new products, new markets or new teams that are being created.

The job description is where the good stuff is hidden - it will describe the key objectives for this role and may include the metrics that the company will measure this role on.

Step 5: Update your industry knowledge

Your customers want to learn from you - and not about your company or products.

They want to understand your opinion and perspective on the challenges they face in their industry.

This week is a good opportunity to update your knowledge by looking for any recently published analyst reports, podcasts, event presentations or competitor stories.

Block out half a day to research. Note down where you found good content for future months.

Step 6: Share one insight with each account

The start of the month is a great opportunity to share some of your unique perspective with your customers.

Too often it can be tempting to only spend your time with the customers where you have active opportunities - but this leads to feast and famine as you swing between closing deals and urgently requiring new pipeline.

Instead I like to think of a circus act spinning plates.

Every month you want to share one useful piece of insight with contacts at each of the customers in your territory - even if they are your competitor’s happiest customer.

Share an insight that is about the customer or their competitors - not about your own company or products.

A recent analyst report, another company’s earnings report, an upcoming industry event.

You don’t need a call to action - just share for the sake of sharing and keep your name in front of your customer.

Step 7: Ensure your forecast is one you believe in

You should have been working on this month’s forecast last month, but now is a good time to ensure you are confident in the number you are calling and the talk track behind it.

Use a forecast canvas to quickly split out:

  • Deals that have closed (if there are any)

  • Deals that are definitely going to close

  • Deals that might close

Be realistic. It is better to tell your manager today that you have a challenge this month and you would appreciate some coaching on how to bridge the gap, than pushing the pain down the road and teeing up another stressful month end in four week’s time.

So there you have it, my seven step monthly kick off framework that helps me get ahead when other AEs are taking a breather.

Completing all of these activities should take no more than one hour each and I would recommend time blocking your calendar for each of those hours individually so you complete them over a couple of days at the start of each month.

I hope you enjoy putting it to work.

See you again next week,


Whenever you are ready, there are three ways that I can help you:

  1. The SDR to AE Promotion video course. In 90 minutes I’ll help you plan for and execute your AE interview process. My exact process for getting job offers.

  2. Get How To Sell Tech as a paperback, hardback, Kindle or audiobook for a deep dive on how to hit your target in your first sales role.

  3. Become a member of our Research Hub where we publish up to date industry and account analysis to help accelerate your research and personalise your outreach.

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