Your Sales Kickoff Can't Fix What You Never Built
Let me say something that might surprise you coming from a sales leader: I believe in Sales Kickoffs. I have run them, attended them, and watched them work when they were built right. The energy in the room when a team locks in on a strategy, celebrates wins together, and leaves with genuine momentum — that is real, and it matters.
But here is what I have also watched happen, more times than I can count. The team flies home. Monday arrives. The slides are never opened again. The new messaging dies in the first tough call. The process the CEO unveiled on day two is quietly abandoned by day twenty-two. And by Q2, the only proof the SKO happened is a hotel invoice and a few blurry photos from the team dinner.
This is not a coincidence. It is not laziness. It is science — and it has a name.
The Forgetting Curve Is Not a Theory. It's Your Q1 Pipeline.
In the 1880s, German psychologist Hermann Ebbinghaus ran experiments on memory and mapped what became known as the Forgetting Curve. His finding: without reinforcement, people forget roughly 50% of new information within an hour of learning it, 70% within 24 hours, and close to 75% within six days.1
That was discovered 140 years ago. We know it. We cite it in training materials. And then we design a three-day annual event, send everyone home, and wonder why nothing changed.
Organizations that fail to plan deliberate reinforcement sequences after their SKO see 70% skill decay within 30 days of the event.2 Seventy percent. Gone in a month. And yet the average company spends approximately $2,000 per sales rep on their annual kickoff — flights, hotel, venue, speakers, swag, and three days of lost selling time.3
For a 20-person sales team, that is a $40,000 investment with a 30-day half-life.
The SKO is not the problem. The absence of what should surround it is.
What SKO Theatre Looks Like
I want to be precise about something. The issue is not that companies hold kickoffs. The issue is that many of them mistake the event for the strategy.
SKO Theatre is easy to recognize. There is a theme — usually something athletic or cinematic. There are slides with bold fonts and ambitious growth targets. There is a keynote speaker who fires the room up for 90 minutes. There are breakout sessions on the new product, the new messaging, the new territory structure. There is a dinner, probably a team activity, and on the last morning, a motivational send-off before everyone heads to the airport still buzzing.
And then they land. And they go back to the same broken CRM. The same unclear ideal customer profile. The same inconsistent qualification process. The same manager who runs a weekly pipeline review that is really just a forecast extraction disguised as coaching.
The SKO pumped energy into a system that was not built to hold it. The energy dissipated, right on schedule, and no one is quite sure why this keeps happening every year.
An HBR study found that 85% of revenue leaders believe go-to-market initiatives are critical to their business success. Yet more than half — 56% — do not feel they have effective solutions to measure whether those initiatives are actually performing.4 That gap is where SKO investments go to die.
The Measurement Problem
Here is a question I ask every sales leader I work with: what was the measurable impact of your last SKO, 90 days out?
Most cannot answer it. Not because they are not paying attention, but because they never established a baseline before the event. They never defined what behavior change would look like. They never built measurement into what happened after.
RAIN Group research found that only 33% of companies rate their sales training as highly effective.5 That is not an indictment of the training itself — it is an indictment of the system around it. Training without reinforcement is not training. It is a very expensive PowerPoint presentation.
The organizations that break this pattern treat SKOs as the starting gun, not the finish line. They build in 30-60-90 day coaching reinforcement plans. They use pipeline data and call reviews to verify whether the new methodology is actually being applied. They connect SKO themes to weekly cadences — not as a checkbox, but as a genuine feedback loop between what was learned and what is being executed.
CSO Insights research is consistent on this point: organizations with continuous sales enablement outperform those relying on one-time training events on both quota attainment and win rates.6 The difference is not talent. It is system design.
The Infrastructure Problem That No SKO Can Solve
There is something more fundamental underneath the reinforcement gap. And it is the real reason many SKOs fail before anyone boards the plane home.
You cannot train your way out of a structural problem.
If your ICP is unclear, training better discovery questions does not help. If your pipeline stages do not reflect how customers actually buy, coaching reps on forecast accuracy is a losing game. If your compensation plan rewards activity over outcome, all the motivational energy in the world will be directed at the wrong thing. If your sales managers are still operating as super-reps instead of coaches, the skills introduced at the SKO will never be reinforced in the field — because the managers do not know how to reinforce them.
Gartner research shows that effective sales coaching can improve rep performance by up to 19%.7 But the same research notes that most managers lack the structure or bandwidth to coach consistently once kickoff energy fades. They are not bad managers. They are operating without a system that makes good management possible.
I learned something about this early in my athletic career that I have never forgotten.
When I was training with the National Sprint Group in Toronto, I was working with athletes I had watched on television. Three workouts a day. My coach was Charlie Francis — one of the most gifted sprint coaches of his era, whose career later ended in controversy and who was largely forgotten. In those early days, I was desperate to prove myself. Intimidated, determined, and absolutely not going to show weakness.
One afternoon, cooling down on the indoor track, Charlie yelled at me to shut it down. I kept running. I did not realize I was limping. He walked across the track, picked me up by my singlet, and explained — in terms I will not repeat here but which were extremely persuasive — that I could listen to my coach, or I could catch the next plane home and call it a career.
He probably saved me from a serious injury that day. I could not see what he could see. That is the entire point of a coach.
The obligation on sales managers in the 90 days following an SKO is exactly this. Not to inspect pipeline. Not to run forecast calls dressed up as coaching. To watch for the limping — the behaviors quietly reverting, the new methodology quietly abandoned, the rep who has slipped back into old habits and has not noticed. To see what the individual contributor cannot see about themselves. The best SKOs in the world accomplish nothing if the coach walks back to the sideline and never looks at how people are actually running.
This is the trap. Companies invest in the SKO because it is visible, scheduled, and energizing. It feels like leadership. It feels like action. What is harder — and less photogenic — is building the underlying infrastructure that makes the SKO mean something. Territory design. Hiring criteria. A qualification process the team actually uses. A forecast methodology built on facts, not optimism. Managers who coach to outcomes rather than just inspect activity.
An SKO is a multiplier. If the foundation is not there, you are multiplying by zero.
What a Well-Built SKO Actually Looks Like
None of this means you should cancel your kickoff. It means you should build it differently.
The best SKOs I have been part of share a few things in common. They start before the event. Ninety days out, buyer feedback and sales data are analyzed to identify the specific gaps the SKO will address — not the gaps leadership assumes exist, but the ones the data confirms. When reps arrive, the training is credible because it is grounded in what buyers actually say about the team's performance.8
They treat content differently. Instead of a full three days of push — new product, new process, new everything — they build in pull. They create conditions where reps want to take information out of the event, because the material is relevant to their specific territory, their specific challenges, their real pipeline. The most effective SKO structures allocate roughly 40% to skills development, 40% to strategic alignment, and 20% to recognition and team building.9 That ratio matters. It leaves room to connect what is being learned to how people will actually work when they leave.
And critically — they plan the 90 days after before they plan the event itself. What behavior change are we trying to create? How will we know in 30 days whether it is happening? Who is responsible for reinforcing it? What does the manager coaching cadence look like starting the Monday after kickoff?
That 90-day plan is not an afterthought. It is the point of the whole thing.
The CEO's Role in This Equation
If you are the CEO of a $10M–$100M company reading this, I want to speak directly to you for a moment.
Your sales leader is not failing because they run bad SKOs. They are very likely doing the best they can with what exists. The question to ask is whether you have built the conditions in which an SKO can actually work.
Has your team defined who your ideal customer actually is — with enough specificity that your reps can qualify against it? Do your sales managers have a coaching framework, or are they running on instinct and tribal knowledge? Is your revenue forecast built on verifiable data, or on reps telling you what they think you want to hear?
If the answer to any of those questions is uncertain, the SKO will energize the room and change nothing. And you will do it again next January.
Build the track first. Then run the race.
If you are preparing for an SKO and want to make sure the infrastructure underneath it is built to hold the investment, I would be glad to have that conversation.
Andrew Devlin is the founder of ScaleTech CRO Ltd. and a Sales Xceleration Certified Advisor (President's Circle). With 25+ years of sales leadership experience at Cisco, Cloudflare, Splunk, and TELUS — and more than $2B in revenue generated — he works as a fractional VP of Sales for B2B companies between $10M and $100M in revenue who are ready to move beyond founder-led growth. He also teaches B2B Sales at Okanagan College in Kelowna, BC. Learn more at andrewdevlin.co.
Sources
1. Ebbinghaus, H. (1885). Memory: A Contribution to Experimental Psychology. Replicated and reviewed in TalentCards, "What is the Ebbinghaus Forgetting Curve?" (2025).
2. Apollo.io, "What Is A Sales Kickoff? Strategy, Planning, ROI Framework" (2024).
3. 6Connex, "11 Tips to Sustain Your Sales Kickoff Event in 2024" (2024); Showpad, "Measuring Your Sales Kickoff ROI" (2020).
4. Harvard Business Review, cited in Gong, "Get More ROI Out of Your Sales Kickoff" (2024).
5. RAIN Group, "Continuous Learning in Sales" research, cited in RAIN Group, "The ROI of Effective Sales Training" (2025).
6. CSO Insights, cited in Sales Partnerships, "Sales Kickoff Is Just the Start: How Top Teams Sustain Momentum" (2026).
7. Gartner, cited in Sales Partnerships, "Sales Kickoff Is Just the Start: How Top Teams Sustain Momentum" (2026).
8. Corporate Visions, "Rethink Your Sales Kickoff: Stop Pushing and Start Pulling Value" (2025).
9. Science of People, "The Best Sales Kickoff Ideas & Tips in 2025" (2025).