When Should You Start Planning Your Sales Kickoff?

By Patrick Crosson, CMP, DES | Chief Experience Owner, PC Events + Experiences

September. If your sales kickoff lands in January or February, planning starts in September and ramps through the fall. That is the short answer, and most of the pressure in sales kickoff planning comes from teams who find it out in November.

Here is what the calendar actually looks like, what has to be locked first, and what still works if you are reading this late.

WHEN SHOULD PLANNING START?

Four to six months before the event, so September for a kickoff in the new year. An agenda can be built in six weeks. Everything that must be reserved before an agenda exists takes much longer.

Hotel room blocks go first. General session space with the ceiling height and rigging points you need goes next. Then the AV labor, because the crews who do this work are booked by the same companies running their own kickoffs in the same two months. Industry coverage says last-minute sourcing is now the norm, which means the teams who decide in September are booking against teams who decide in December. January and February are the tightest weeks of the corporate year.

Start in September, and you are choosing. Start in November, and you are taking what is left. We have written before about why booking early wins for fall meetings, and the same math applies to a January kickoff.

WHAT HAS TO BE LOCKED FIRST?

Three things, in this order.

• The date. Pick it before the venue. Every other decision moves to fit it.

• A headcount range. A range from senior leadership, not a guess from sales. Plus or minus fifty people changes the hotel, the F&B minimum and the AV spend.

• The room. Room block, general session, breakouts and at least one evening space, booked together rather than one at a time.

Our hotel and venue sourcing work starts here, because a sourcing brief with a soft date and a soft headcount gets soft options back. Before any of it, we run a Brand Immersion Meeting, so the brief carries the purpose of the kickoff and not just the dates.

WHAT CAN WAIT?

More than people think. Theme, swag, entertainment, the awards format, the breakout titles. All of it can be built in November and December without hurting the event.

Teams get this backwards. They spend September arguing about a theme and December discovering there is no ballroom. The theme is the fun part, which is exactly why it is the part that eats the planning window.

WHAT DOES THE KICKOFF HAVE TO DO BY THE TUESDAY AFTER?

This is the test worth running on every agenda item. On the Tuesday after everyone flies home, what should be true that was not true the Friday before?

If the answer is that 300 sales leaders can explain the new pricing to a customer without opening a deck, the agenda builds itself. If the answer is that people felt good about the year, that is a party, and a party is a fine thing to also have.

We ran the G2 Company Kickoff four years running, nine events across that stretch, 300 sales leaders at the two-day program with two evening events. The agenda got sharper every year because the Tuesday test kept getting asked, and the answers came back through our post-event debrief in time to shape the next one.

"The kickoffs that work are the ones where somebody can tell me, in one sentence, what has to be different on Tuesday. That sentence does more for the run of show than any theme."

Patrick Crosson, CMP, DES, Chief Experience Owner, PC Events + Experiences

WHAT IF WE ARE STARTING LATE?

You still have a kickoff. You have fewer choices, and the choices move from the ones you wanted to the ones that are open.

What opens up late: secondary cities, Sunday and Thursday arrivals, hotels outside the convention core, and properties with a gap because somebody else moved. Plenty of planners are moving to secondary markets on purpose now, for cost as much as for space. What does not open up late: the ballroom in the city everyone named in the first meeting.

Late is also when vendor mistakes get expensive, because there is no slack to absorb them. Ask the questions most planners skip with vendors in the first call, not the third.

At Sysdig's sales kickoff in Las Vegas we ran 14 regional dinners across The Cosmopolitan and the Aria, with a registration reception called Badges and Bubbles, six-foot LED letters on the main stage, and a Women Who Inspire panel luncheon with five women tech leaders that we pushed the client to add. More than half the room came, many of them men. That is what a well-run kickoff still looks like when the producer already holds the relationships in the market.

There is still the case for getting people in a room together, even on a compressed timeline. The compressed version just needs somebody who has done it before holding the calendar.

FREQUENTLY ASKED QUESTIONS

How far ahead should we book a hotel room block for a sales kickoff?

Six to nine months out for a January or February kickoff, and earlier if your headcount is over 200 or your dates sit inside a city-wide convention. Room blocks are the first thing to go and the hardest thing to fix late. If you are reading this in the fall for a kickoff in the new year, the block is the call to make this week.

How many breakout sessions does a sales kickoff need?

Fewer than most agendas start with. Two days of programming with 300 sales leaders works better with three or four tracks that people can actually choose between than with eight that split the room thin. Build the tracks around what you want sold differently in Q1, then cut the ones that do not answer that.

Can we include remote and virtual attendees?

Yes, and it changes the room, the AV plan and the run of show, so decide it early rather than bolting it on. A hybrid kickoff needs a camera plan, a dedicated audio feed and someone whose only job is the people who are not in the room. Decide in the first month, not the last.

What does a sales kickoff cost?

It moves with headcount, city, number of nights and how much of the programming is produced. Ask for a range against your headcount and your date before you fall in love with a venue.

What if we are already late?

You still have a kickoff. You have fewer choices. Secondary cities, shoulder dates and hotels outside the convention core open up quickly, and a producer who already holds relationships in those markets can move faster than a fresh RFP can.

Who should own the kickoff internally?

One person with budget authority and one person with calendar authority, and ideally they are the same person. The kickoffs that slip are the ones where the date is owned by sales, the budget by finance and the content by enablement, with nobody holding all three.

WE GET KICKOFFS DONE.

If your kickoff is in January or February and the room is not booked, that is the call to make this week. Our event management team runs these from sourcing through transportation and budget, in Chicago and wherever your people are flying to.

Ask us about a kickoff that moved cities six weeks out. Or just talk to us and bring your date.