The Sprint to December: January & Planning

How to Survive the Sales Kick-Off

Sales Kick-Offs are energizing, noisy, and full of good intentions. Sadly they are rarely the place where real insight happens.

The first rule of SKO... The aim isn’t motivation. It’s clarity.

Before SKO:

1. Look Back and Decide What You’re Listening For

Before you walk into SKO, create a small pocket of space to review last year honestly and prepare intentionally for what’s ahead. Talk with a coach, a trusted colleague or a former boss and use the following questions to reflect:

• What closed last year that genuinely surprised you?

• What didn’t close that you were convinced would?

• Where did your bluebirds fly in from,? referrals, timing, relationships, luck?

• Which deals died quietly, and which died noisily?

• What patterns show up when you strip out the anecdotes?

Take notes. Then

2. Review the SKO agenda in advance.

Plan:

• What topics are most relevant to your territory and accounts?

• Where do you already have strong opinions, and where do you need more data?

• What questions do you want answers to by the end of SKO?

• What assumptions do you want to challenge or pressure-test?

• What are you listening for, beyond the slides?

Finally, be deliberate about who you connect with. Your network is your net worth

• Identify peers, sales leaders, or partners whose perspective would sharpen your thinking

• Compare notes on what’s working, what’s stalled, and what feels different this year

• Use informal conversations to spot patterns you won’t hear on stage

The goal isn’t to collect business cards. It’s to leave SKO with better context than you arrived with.

3. During SKO: Listen for What’s Being Reinforced

SKOs are as much about signals as they are about content.

Notice:

• What behaviors are being praised publicly?

• What gets airtime — pipeline creation, deal size, velocity, heroics?

• What assumptions are being made about how deals are won?

• What’s said about compensation — and what’s not?

This isn’t cynicism. It’s sensemaking. I could add a lot more here - sleep more than you drink, participate in the activities and meet as many of the attendees as you can

4. After SKO: Turn Insight into Forward Motion

Within a week of SKO, move from inspiration to intentional action. This is where your year-end reflection and SKO pre-work start paying dividends.

Use what you’ve already learned to decide what changes now, not later.

Ask:

• Based on last year’s surprises, which sequences are worth repeating, and which need to be redesigned?

• What did SKO reinforce, contradict, or ignore about how your best deals were actually won?

• Which accounts and opportunities deserve increased focus because they align with real momentum, not hope?

• Where does your territory need tightening, fewer bets, clearer bets, better bets?

• What activities looked productive last year but failed to move deals forward, and will be deliberately dropped?

• What one or two concrete changes, made in the next 30–60 days, would leave your pipeline measurably healthier?

The aim isn’t to do more after SKO. It’s to make earlier, clearer choices, so energy turns into progress, not noise.