10 Best Practices for Your Next Planning Session

Posted by Jack Derby, Head Coach on Wed, Mar 27, 2019

It's that time of year again...

  • Just a few days away from the end of the quarter and whether the scale is on the positive or the negative side of the measuring stick, it's time to take a quick look back and a three quarter look ahead.
  • It's time to pull the team together for a day or two planning session to reconfirm or change the longer term strategies (primary directions), tactics (quarterly plans), and activities (primary actions)
  • Whether it's for the entire business, for sales and marketing or for engineering and operations, the activity of bringing everyone together is critical to your success as a manager and as a team member.  

    planing dwight-david-eisenhower-quote-in-preparing-for-battle-i-have-always-1Eisenhower reflecting on the ultimate success of the invasion of Normandy, which originally was a disaster during the first few weeks, said it best:
It's the physical act of bringing people together to plan that is the most important responsibility of a manager and critical to activating players as a unified team.

We've now done hundreds and hundreds of these one and two day planning sessions and wanted to share a few Best Practices at the beginning of the most important quarter of the year since there's still plenty of time to enact and execute on any change you want to make and realize the benefits of the change in Q4. 


1. Use two days. With a specific agenda in place, give everyone homework to engage in in advance.  Use the first day to bring ideas, and potential solutions to the table.  Come together at the end of a long day for a non-work dinner...and wine.  Use the next day to refresh, recalibrate and reconfirm the specific decisions going forward for the balance of the year.

MIT Endicott House-12. Go offsite.  The physical activity of going somewhere else provides formality, eliminates interruptions and provides the confidentiality of a location out of the office.  There are plenty of unique and lower cost options such as the MIT Endicott House just outside Boston that are specifically set up for business meetings.  Really, really try to stay out of the standard chain hotels if you can; they just dull down creativity! 

3.  Logistics.  The best sites and most effective meetings are created in part by (1) the most comfortable chairs, (2) instant access to a variety of electronics, (3) lots of physical walking around room during the meeting and (4) food-built-for-meetings (low sugar, high energy, and delivered on time).

No cell phones4.  No Calls, no Text, no Emails. Unless there's an emergency, simply prohibit outside access except during breaks. This is serious stuff, and you want everyone focused.  We always use "The Derby Rule"...Last person into the room after the appointed time, owes everyone else $5, and if you do chose to use your email or phone or if your phone rings, you owe everyone else the same $5.  Works all the time.  The money goes to the company's favorite charity.  And, yes, I have also paid the fine...once $345 at a Fidelity sales planning session a couple of years ago.

meeting facilitation5.  Use a Facilitator.  I really do not want to "sell" you here since strategic planning is one of the activities that Derby Management does.  Sure, we would love to work with you, but much more importantly than using us, use someone outside as a facilitator, who is highly experienced, to take you through the process from concept, to objectives, to agenda, to running the meeting, to taking the official notes and then following up with everyone post-meeting.  By definition, from 25 years of doing this, I do know that if "the boss" tries to run the meeting, open, frank and objective discussion will be limited to some degree.

6.  Preparation.  Be selective about who is at the meeting.  Talk to everyone beforehand to understand their own personal objectives for the meeting.  Send out a draft agenda for comments and refinements at least a full week before the meeting.  Give homework in at least a reading assignment, and consider having everyone send in a limited SWOT beforehand and sharing that with the entire planning team...before the meeting.

Time for breaks 7.  Simplify the time and the breaks.  15 minute email breaks at 10:30 and 2:30. 45 minutes for lunch.  Wrap things up on the first day with a summary of takeaways at 5:30ish. Engage everyone in an early dinner (non-work) together.

8.  People.  Keep the meeting attendance relatively small.  We like to think that that number is around 10 people.  At a company level, it's the entire senior team.  For the senior sales management, it's all the regional managers, or maybe the regional and the field managers. For real team building, make sure that you invite the head of marketing also.

That number of 10ish provides great crosstalk and ensures that no one is left out and also keeps the meeting content manageable.  It is critically important to the success of the meeting that the Facilitator talks individually with everyone prior to the meeting and understands one-on-one everyone's concerns and their own objectives.  "So, at the end of this meeting, what do you want to leave there with?"  is a great question for everyone to answer individually prior to the meeting.

9. Consistency.  One meeting is a total waste of time!  Get into the habit of building these meetings into the rhythm of your business whether that's quarterly, every six months or once a year.  Lock those dates into your company calendar a year in advance.

10.  Have Fun. This planning stuff is really tough work!  It is also extraordinarily rewarding, but the very nature of the process is meant to take people out of their comfort zone and focus 12 to 36 months into the future.  Make the meeting memorable by naming it, provide logo wear, give it a theme...or just do something to make the process fun and remembered.  No, meetings like this do not have either the time or the purpose for ropes courses or walks in the woods!  Those are very different type of meetings although for all or our meetings, and our two day Sales Management Boot Camps, we do provide 7:00 AM jogs for those who want to join in. 

Hope that this helps with a few ideas gathered from 25 years of running planning sessions.  Questions?  Just connect. 
Have a Great Selling Day today !

Sales Management Boot Camp 2017-3.png-3Join us at our upcoming  
Sales Management Productivity Boot Camp in mid-June!

Tons of content, practical takeaways and peer learning between the end-of-the-day working dinner over case studies beginning on June 16th and extending to mid-afternoon on June 18th.

Designed for sales managers at any level, this always-sold-out intense experience is specifically customized to maximize your and your team's performance so that you beat your 2019 Quota!

Too many details to cover here plus most of the outline is on the site so just click on above. Much better to just connect directly with me, at jack@derbymanagement.com, and we can set up a 10-minute call to judge fit and answer all your questions.  After many years of doing this with now more than 1,000 sales managers, presidents and CEO's, we just simply guarantee results!


Jack Derby

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Jack Derby, Director, TEC-Tufts Entrepreneurship Center
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Cell:  617-504-4222 jack.derby@tufts.edu  

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Tags: sales planning meeting, business planning meetings, Making Tough Choices, sales management plans, sales management productivity, sales effectivness