26 Sales Kick-Off Mistakes and How Experts Avoid Them

Disclaimer: The views and opinions expressed in this article are those of the individual contributors and do not reflect the official policy or position of their current or previous employers. This content is for informational purposes only.

Introduction

This article is a part of a series on the subject of sales kick-offs. Make sure to check out the articles on sales kick-off best practices, sales kick-off themes, and sales kick-off planning as well.

Sales kick-offs are arguably the most complex events under enablement’s purview – especially when you factor in finances and logistics.

Due to this complexity, hiccups happen and range from common mistakes, such as scheduling mixups, to major ones, such as an agenda that is completely misaligned with the company’s GTM goals for the year ahead. 

Luckily, I was able to talk to 16 sales leaders who have led enablement teams at companies like IBM, Salesforce, SAP, Yahoo, and GitLab, just to name a few:

Alicia Avrach  – Head of Sales Enablement

Beverlie Heyman –Director of Revenue Enablement

Eric Mingorance – Sr. Director of Sales & Field Enablement

Ivy Holt – Head of Global Revenue Enablement

Kelley Shirazi – Director, Global Sales and Customer Success Enablement

Lauren Channell – Senior Manager, Enablement Business Partners

Leah Levitte – Director, Revenue Enablement

Liz Chavez – Senior Director of Revenue Enablement

Louisa Morassutti – Senior Director GTM Enablement

Mat Hill – Sr Director, Revenue Enablement

Monti Bray – Director, Sales Enablement

Nina LaRouche – Director, Revenue Enablement

Paul Harvey – Head of Sales Learning and Practices – Global VP

Russell Wurth – Head of Revenue Enablement

Tim Carlson – Director of Sales Enablement

Todd Lienart – Director, Revenue Enablement

I specifically asked them about the most common SKO mistakes they have seen in their career, how they can affect the success of a sales kick-off, and how they avoid such mistakes. 

Once again, the collective knowledge of such an experienced and tuned-in group of leaders has come through in a big way, sharing what they’ve encountered and discovered over the years. 

26 SKO mistakes you should know about

When I said that the contributors came through in a big way, I wasn’t just being nice. 

Namely, once I was finished reading through their insights and organising them in a reader-friendly way, I ended up with 26 distinct SKO mistakes altogether. 

For a more comfortable and intuitive reading experience, I organised the individual mistakes into 6 larger mistake areas. 

The image below offers a quick overview. I recommend reading the full guide, but if you’re short on time, feel free to jump to the section that interests you most.

I structured the article so that the most strategic and impactful mistakes are discussed first, followed by those that, while still important, may have a lesser impact (though it is not always easy to truly predict). 

So, let’s dive in. 

No shared clarity and strategic coherence

When the purpose of your SKO isn’t clearly defined, the entire event risks devolving into a chaotic free-for-all. 

Without well-defined objectives, executive alignment, specific pain points to address, and a designated decision-maker, departments compete for attention, ultimately diluting the event’s impact.

Below are the key mistakes the contributors pointed out in this area, along with advice on how to avoid them.

Mistake #1: Unclear or missing objectives

Liz Chavez, the Senior Director of Revenue enablement at a leading company for identity threat protection, identified the lack of clearly and strictly defined objectives as one of the most common mistakes to steer clear of:

“The most difficult SKOs are when there are no clear objectives and therefore every group feels entitled to time on the agenda. 

Those tend to run long and are tedious. 

SKO needs to align to the business objectives for the year and therefore each session is selected to support those goals.

Unfortunately, this may mean some groups don’t present, but the agenda needs to be a reflection of priority for the sales organization.”

Eric Mingorance, the Senior Director of Sales & Field Enablement at a cloud-based and on-premises software-defined video platform, explained what ends up happening in such situations:

“Randomly planning for ad hoc topics that do not sync with the overall objective and theme.”

How to avoid it:

• Clearly define and communicate the SKO’s objectives before planning begins. 

• Ensure that every session is mapped to these objectives so that all teams know exactly what the event is meant to achieve.

Mistake #2: Lack of executive alignment

Alicia Avrach, the Head of Sales Enablement at a world-renowned full-stack generative AI platform for enterprises, agreed with Liz’s point on the importance of clear goals and outcomes but also emphasised that there must be alignment among executive stakeholders. 

Their inputs can be difficult to ignore by even the most established enablement departments, and by ensuring their alignment at the very start, you can prevent many uncomfortable and politically charged conversations. 

How to avoid it:

Organise alignment meetings with key executives before the SKO planning starts. Achieving consensus among leadership provides a clear, unified vision that guides every part of the agenda and avoids mixed signals on priorities.

Mistake #3: Relying on leadership for the agenda

While leadership alignment and participation are obligatory, you should never go the completely opposite way and think that the leadership will come up with an actual agenda. 

For one, their day-to-day responsibilities don’t give them nearly enough time to think about SKO agenda except for identifying highest-level objectives and taking a big-picture glance every now and then. 

Monti Bray, the Director of Sales Enablement at one of the internet’s OG companies, has a very straightforward advice for evading this mistake:

“Build a skeleton first and give your exec team something to react to.”

This way, they are apprised of how you’re planning to meet the objectives and achieve the agreed-upon outcomes, and they can give their opinions on whether you’re going in the right direction.

How to avoid it:

Do as Monti suggested.

Mistake #4: Misaligned sales and marketing

Kelley Shirazi, the Director of Global Sales and Customer Success Enablement at one of the two DevSecOps platforms that 99% of software development teams choose between, had a specific cross-departmental misalignment in mind – the one between sales and marketing teams:

“Misalignment between sales and marketing. 

This isn’t really on enablement to solve, but can have an extremely detrimental effect on morale and outcomes if not handled correctly. 

Let’s say marketing is pushing heavily on messaging compliance and wants to have a pitch competition as part of SKO. There’s nothing inherently wrong with this, and ensuring messaging resonates with the buyer is critical. 

However, if pitching isn’t the problem, but rather the team’s ability to pivot on the fly and effectively engage with different personas is, then you’ve wasted the opportunity to improve outcomes by misdiagnosing the problem.”

How to avoid it:

Kelley was kind enough to also advise on how to avoid this mistake:

“To bridge this gap, enablement teams should collaborate closely with sales leadership when designing SKO content and breakout sessions, and build WITH them. 

If a pitch competition is necessary, it should be supplemented with sessions that address key skill gaps identified by revenue leaders, like negotiation, objection handling, or closing strategies. 

That way, Field teams will get a more well-rounded experience they can take back and apply in the flow of work.”

Mistake #5: Focusing on entertainment over outcomes

Some sales kick-offs are more extravagant than others – perhaps the company has had a great year, or it’s simply part of the company culture.

While fun and team bonding are important, the primary focus of an SKO should always be on driving outcomes, not just creating a feel-good atmosphere.

As Paul Harvey, the Global VP of Sales Learning and Practises at a leading global wholesale provider of insurance and reinsurance products, puts it:

“Worrying about the entertainment etc… 

You want the teams to leave ready for action not pleased they had free drinks and a great guest speaker.”

How to avoid it:

To strike the right balance, design your SKO with clear, outcome-driven sessions first; then layer in engagement elements that enhance, rather than distract from, your objectives.

Ensure every activity, from keynotes to team-building exercises, ties back to a core business goal. Instead of prioritising entertainment, focus on hands-on workshops, real-deal strategy discussions, and skill-building sessions that prepare your team to take action immediately after the event.

Fun and celebration should be part of the experience, but they should serve as a complement – not the main event.

Mistake #6: No clear decision-maker 

Liz Chavez wrapped up this section perfectly by pointing out an often-ignored-until-far-too-late mistake that usually ends with a death-by-committee outcome: 

“No clear decision-maker. 

There are a lot of opinions so it needs to be clear who makes the final call. Usually, this is the CRO but not always. 

Be clear when communicating to stakeholders you’re happy to take the input, but it’s ultimately their call on what moves forward. 

Otherwise, enablement can feel like an order taker trying to please a wide array of asks across GTM teams.”

How to avoid it:

Appoint (and communicate) a single final decision-maker early in the process. This person should have the authority to make the ultimate call on questions of strategy and agenda, thereby preventing endless debates and ensuring a streamlined planning process.

The next mistake area is closely related to the aforementioned strategic mistakes, most notably because they tend to happen concurrently. 

I am talking about getting too much input from too many people. 

Too many cooks in the kitchen

Closely linked with unclear objectives is the challenge of having too many opinions, too many voices, active participants, and, consequently, an oversized SKO planning team. 

When everyone has a say, the event risks becoming bogged down in endless discussions rather than focused execution. 

Below are the individual mistakes in this area, along with guidance on how to avoid them.

Mistake #7: Too many voices

Mat Hill, the Senior Director of Revenue Enablement at a Healthcare CSPM and MDR services company, was clear about one of the most detrimental mistakes in a sales kick-off: allowing too many people to have input.  

Nina LaRouche, the Director of Revenue Enablement at a leading full-funnel retail platform, echoed his sentiment and actually christened this section:

“Too many ‘cooks’ in the kitchen with regards to session content/facilitation”

How to avoid it:

• Identify and limit input to key stakeholders by designating clear roles. 

• Define a scope for contributions to ensure the agenda remains streamlined and aligned with the overarching objectives. 

Mistake #8: Discussing over doing

Paul Harvey elaborated from a more personal standpoint about how having too many people in the planning committee can derail things:

“We had a large team involved with the planning of the event and spent more time discussing actions and not actually doing stuff! So the event was not as smooth as it could/should have been.”

How to avoid it:

Paul kindly gave his advice on how to avoid this from happening and ensure the team stays agile, saying that since he learned his lesson, he’s always tried and had much smaller teams (max 4) as the organising committee.

Mistake #9: Letting stakeholder creep derail your SKO budget

Liz Chavez had another word of warning of what can happen when an SKO starts attracting too many stakeholders (and you let them). 

More precisely, she shared a cautionary tale of an SKO budget exploding by about 1,400%:

“I had an SKO absolutely explode out of budget due to the 2 mistakes I mentioned above (no clear decision-maker and no clear objective). 

Initially, I was scoped to have a 1/2 day meeting for 50 salespeople, with a budget of $7000 but as more stakeholders got involved, the expectations grew and we ended up having a 350-person, $100,000 event. 

One sales leader kept forwarding the invite to other teams and never asked for approval, so we ran out of food within the first 15 minutes of lunch. 

It was death by committee and since no one person was the decision-maker, they all felt entitled to have their demands met.”

Liz adroitly explains how a combination of too many stakeholders and some of the mistakes we’d covered earlier can turn into a budgetary nightmare.

How to avoid it:

• Set clear boundaries from the outset regarding who is involved in decision-making. 

• Establish strict guidelines to control the scope and budget, ensuring that additional stakeholder input is filtered through a single point of accountability.

Agenda bloat 

Both of the mistake areas I’d covered earlier are almost certainly bound to lead to the kinds of mistakes included in this section. 

Moreover, the mistakes related to overbearing amounts of talks, sessions, and other agenda components were by far the most commonly mentioned by the contributors. 

Mistake #10: Overloading the agenda

Quite a few contributors felt that their warnings about cramming too many sessions, talks, and topics into the agenda could be summed up as overloading the agenda.

These included Eric Mingorance, Lauren Channell, the Senior Manager of Enablement Business Partners at a leading full-funnel retail platform, and Russell Wurth, the Head of Revenue Enablement at a cyber risk detection and response platform. 

Louisa Morassutti, the Senior Director GTM Enablement at a leading provider of talent acquisition technology, noted that in the rush to pack the agenda, many SKOs overlook the need for time to digest information and include sufficient breaks.

Ivy Holt, the Head of Global Revenue Enablement at a world-renowned platform for real-time operations, also warned that:

“An overpacked SKO agenda can overwhelm participants and dilute the impact of the content.”

How to avoid it:

• Streamline your agenda by consolidating similar topics. 

• Stay focused and be merciless when cutting sessions/talks/workshops that don’t align with your core objectives. 

• Ensure ample breaks between sessions so that participants have time to process the information and avoid feeling overwhelmed.

Mistake #11: Assuming the people-pleaser stance

As you’ve probably noticed, I usually preface the contributors’ quotes with a bit of context, but in the case of the following insight from Tim Carlson, the Director of Sales Enablement at a company that builds mathematically accurate network digital twins, I don’t really think it’s necessary. 

His words speak volumes:

“A lot of Enablement folks get stuck in ‘people pleaser’ mode, and lose sight of the needs of the audience.  

Enablement has to ask the tough questions (‘Should preso X be included and why?’), and have the backing of Sales Leader/CRO when disagreements arise.  

This does not mean the sales leader rubber stamps the enablement person’s position but simply ensures a fair discussion on the merits of including/excluding a topic. 

Corporate tends to want to pack every waking moment of SKO with sessions. Not providing some unstructured time for people to connect makes it nothing more than yet another mandatory meeting.”

As enablers, we sometimes fall into a people-pleasing stance—often because driving initiatives without explicit authority requires a fair amount of politicking.

We just need to be mindful not to take it too far.

For everyone’s sake.

How to avoid it:

• Prioritise what the audience truly needs by setting clear, data-driven criteria for session inclusion. 

• Insist on asking the tough questions and secure the backing of the chief revenue officer or someone else from leadership to validate your choices rather than merely pleasing everyone.

Mistake #12: Time-wasting breakouts

Breakouts can be a great way to reinforce key messages and foster interaction among SKO attendees, but they can easily spiral out of control.

A typical tendency is to fill up every gap in the schedule with a breakout “because they keep the reps engaged”.

Todd Lienart, the Director of Revenue Enablement at one of the most popular generative AI platforms for marketing, warns about even the most well-intentioned breakouts being potentially time-wasting:

“Time-wasting breakout sessions. (I have made this mistake a lot) 

There are so many ways that we waste people’s time with well-intentioned group work like “discussing this persona”. 

Your sales and CS teams should have a say in what they do or don’t do in their breakout.  

Don’t decide for them – grab a few of them and tell them what their management is thinking and how we can design something useful for them. 

Take it to heart.”

How to avoid it:

I really couldn’t put it better than Todd did with his last three sentences. Go back and re-read them.

Mistake #13: Bringing the everyday to the SKO

Another way the SKO agenda can become overloaded is by squeezing in training or breakout sessions that could just as easily take place on any other day.

These sessions stand out by adding little unique value or straying from the core focus of the event.

Monti Bray describes this perfectly:

“Running a session or training they can do just as effectively the week before or after getting everyone together. 

Content should feel unique and oftentimes is best received when it doesn’t actually come from enablement”

How to avoid it:

• Ensure that every session, training, or interaction serves a distinct purpose rather than being added just for the sake of it.

• If enablement is leading the charge, ask yourself: “Could this be done next Tuesday instead?” Respect your team’s time.

An overloaded agenda is one of the fastest ways to diminish the SKO experience for the people who matter most: the sales team.

Next, we’ll explore other mistakes that can make an SKO underwhelming for reps.

Neglecting the reps’ perspective

As I mentioned above, the SKO’s main target audience is the front-line sellers. 

Unfortunately, this sometimes feels like an afterthought.  

I’ve observed this myself and it is clear that many of the contributors share my experiences. 

But, what exactly are the mistakes that make SKO’s less salespeople-focused and salespeople-friendly than they should be?

Mistake #14: Not giving reps what they need

Tim Carlson couldn’t have been more direct if he wanted when he spoke about organising SKOs for the reps:

“You have to build SKO with the rep in mind. Not what the Product team wants. Not what the Marketing team wants. But what the reps want and need.”

How to avoid it:

Luckily for us, Tim was also crystal clear on how to avoid this mistake:

“Sales reps CRAVE time to sync with peers beyond their immediate bubble. Compare notes, discuss challenges, discuss sales strategy, share best practices, etc.”

Give them all the opportunity you can to do those things.

Mistake #15: Too much passive content

Once again, I feel that an introduction would just take away from how well Kelley Shirazi explained this particular mistake:

“Too much passive content causes attendees to lose interest and lowers engagement, which in turn causes key concepts to be quickly forgotten. 

SKO should be a time to help prepare teams to execute in the field, not attend your TED Talk. 

Along the same lines, (and this may be an unpopular opinion), I would steer clear of motivational speakers. 

While there are some great speakers out there, as a seller I have little to nothing in common with someone who has summited Mt. Everest, gone into space, or who focuses their entire speech on how your biggest blocker is attitude and mindset. 

I get it, we’re supposed to be inspired – and often these are amazing stories. But at an SKO, I’d rather be setting myself up for success with a keynote speaker teaching me practical strategies for negotiation, as an example. 

If you’re going to spend the money on a speaker, make it count.”

I found Kelley’s point about motivational speakers particularly interesting. 

I think that a little inspiration can be helpful, but only if it supports the broader theme and objectives of the SKO. 

The reality is that while an inspiring story may create a temporary boost in morale, only a small percentage of people will actually take action as a result. 

On the other hand, practical strategies – especially when reinforced with supporting materials and post-SKO follow-ups – have a far greater chance of driving lasting impact. 

If you’re going to bring in a speaker, it’s worth considering whether their message will translate into meaningful change for your sales team long after the event.

Leah Levitte, the Director of Revenue Enablement at a company behind an intelligent auditing and finance automation platform within Excel, also sees the passivity of content as a major missed opportunity:

“Not fully taking advantage of an in-person event, i.e. just presenting straight PowerPoint slides that you could have done virtually.”

And she’s right – nothing loses a sales audience faster than a presentation that feels like it could’ve been an email. 

If reps feel they’re being talked at rather than engaged, you’ll see their attention slip almost instantly.

How to avoid it:

• Shift from passive, lecture-style sessions to dynamic, interactive formats that demand engagement. 

• Focus on activities that encourage participation – like role-plays, group discussions, and live Q&A – so that every session delivers practical, actionable insights. 

Mistake #16: Not allowing enough time for breaks 

Failing to build in sufficient breaks is a common oversight that can significantly impact your reps’ experience and engagement throughout the SKO.

Leah Levitte reminds us that salespeople are people first:

“SKOs are very draining and people really need that extra time to decompress, do work, call their family, etc.”

Eric Mingorance focused more on how a lack of breaks (and poor scheduling) can derail the entire SKO and leave the reps twiddling their thumbs instead of engaging with other attendees:

“Not enough time in between sessions so swapping speakers or laptops or setting up a V is hectic and sessions do not start on time. 

Additionally, people from different geographical areas will never use that time to talk to one another in between sessions. 

So quick and smooth transitions need to be planned and where that’s not possible put in purposeful longer breaks that everybody can take advantage of.”

How to avoid it:

Plan breaks with the same level of intention as your sessions. 

Ensure there is enough time between sessions for smooth transitions, speaker changes, and necessary setup adjustments.

Consider these tips:

• Schedule at least 10-15 minutes between sessions to allow for speaker transitions, equipment setup, and informal conversations.

• Include longer breaks (e.g., 30-45 minutes) after intense sessions or before networking opportunities to let attendees recharge.

• Encourage purposeful breaks by providing spaces for reps to connect, check in with their teams, or simply decompress.

A well-paced agenda prevents fatigue, and keeps reps engaged, aiding in the retention of key takeaways rather than just powering through the day.

Mistake #17: One-size-fits-all content

The challenge of one-size-fits-all content is more nuanced in SKOs than in other enablement initiatives, where the straightforward answer is to personalise as much as possible.

Ivy Holt captures this complexity well:

“A one-size-fits-all approach can leave parts of the sales team feeling disconnected from the content.

You’re not going to please all the teams and everyone. People will always complain that it didn’t apply to me.”

She acknowledges that while some level of generalisation is necessary, post-SKO activities can introduce tailored content where needed:

“Do your best to do content that is one-size-fits-most and then add the regional, role-based enablement throughout Post-SKO events.”

How to avoid it:

• Instead of striving for complete personalisation, aim for one-size-fits-most content that resonates with the majority of your audience.

• Then, reinforce learning with post-SKO sessions tailored to specific roles, regions, or challenges that weren’t covered in-depth during the main event. 

Mistake #18: Scheduling critical content too late

Sales kick-off schedules are difficult. 

There are too many moving parts which require a lot of coordination, and certain scheduling hiccups are bound to happen. 

However, Todd Lienart pointed out one major scheduling faux pas which can have significant consequences for the success of the entire SKO: placing critical content too late in the day or, in the case of multi-day SKOs, delaying it beyond the first day.

This way, you increase the chances that people will be too tired or already overwhelmed with less critical information to properly engage with the most crucial part of the SKO. 

How to avoid it:

I’ll let Todd answer this one himself:

“Front-load the important stuff on Day 1. 

The audience will be in the best frame of mind that day. There is excitement at being together, and a better willingness to do more work.  

After the evening event, a second or third day should be more for topics that don’t require as much critical thinking. 

I wish this weren’t the case, but after 11 SKOs with tech sales – this is now something I’ve learned doesn’t change.”

No reinforcement/follow-through

Even if you manage to avoid the 18 SKO mistakes I’ve covered so far, without post-event and during-event reinforcement and follow-through, the chances of your sales kick-off having a lasting effect on your sales force are virtually nonexistent.

This is why I wasn’t surprised to see a number of the contributors touch upon this topic. 

Mistake #19: No post-SKO reinforcement plan

Lauren Channell and Beverlie Heyman, the Director of Revenue Enablement at a company behind a revolutionary Human Experience healthcare platform, shared their views that not having a post-SKO plan or post-event support resources or activities are some of the biggest mistakes in their books. 

Kelley Shirazi shared about a specific SKO she was involved in and where this mistake was made:

“The enablement roadmap filled up so quickly with company priorities that all of the work we’d done got lost. 

As a result, teams weren’t able to carry through the energy and excitement from what they’d learned and applied SKO but instead had to context switch to yet another priority initiative.”

How to avoid it:

Perhaps the best course of action for avoiding this mistake was given by Kelley in the rest of her story:

“One big lesson learned is that you have to follow through and build a reinforce and sustain motion for the learning and practical skill application provided at SKO. 

A good solution would be to build in a 30-60-90 day post-SKO reinforcement plan and use tools to track progress and adoption.”

Mistake #20: Not reinforcing during the SKO

Reinforcing is not only done after the SKO has finished. 

As Russell Wurth explained, it is just as important to include sessions in your agenda that will help salespeople remember what they’ve just learnt. He emphasised the importance of involving sales managers and leadership in this process:

“I tried to do too much without ensuring the sales leaders were there to not only endorse but reinforce.”

How to avoid it:

Once again, the person who pointed out the mistake also came up with a solution:

“Don’t shy away from repetition between sessions, it helps for remembering and reinforcing. I stepped up my communications to all to ensure alignment.”

Ignoring logistics and practicalities

Up to this point, we’ve focused on the content, as well as the experience of both planners and reps during sales kick-offs.

Now, it’s time to acknowledge the other side of SKOs – the planning and execution that ensure everything runs smoothly and allows those great experiences to happen.

In other words, we’re shifting focus to the mistakes that stem from logistics and the practical aspects of running a sales kick-off.

Mistake #21: Not communicating clearly 

As in all things enablement, good communication is paramount for success, and SKOs are no different. 

With so many moving parts and a large number of people involved – planners, executors, and attendees – unclear communication can quickly become a major issue.

Alicia Avrach warns about the dangers of unclear communication:

“It’s really easy when you have 200 salespeople for then to get confused about where and when to show up during the program.”

How to avoid it:

Establish dedicated, clear communication channels well before the event so every participant knows the schedule and whom to contact if issues arise. 

Louisa Morassutti suggests setting up a war room and a real-time communication channel (Teams, Slack, or WhatsApp) to handle any technical and logistical difficulties quickly and efficiently.

Mistake #22: Doing the hybrid thing

Hybrid SKOs often split focus and resources, leaving neither group properly served. 

Remote attendees miss hallway conversations critical for team bonding, while in-person participants get distracted by virtual logistics.

It is as Nina LaRouche says:  

“Don’t try to do hybrid – it will be a bad experience for someone.” 

I think Nina was actually being gracious here, using someone instead of everyone. 

How to avoid it:

Nina shares a very simple (yet difficult) way to avoid this mistake: 

“Make the difficult decision to either go fully in person or fully remote. If remote, it has to be much shorter, perhaps over more days if required.”

Mistake #23: Overestimating the reps’ motivations

It’s easy to assume that every attendee arrives at SKO eager to absorb new insights, refine their skills, and return to the field as a stronger salesperson. 

In reality, while that may be the organisation’s ideal outcome, it’s not always what reps prioritise.

As Todd Lienart has observed over the years, many attendees see SKO less as a personal development opportunity and more as a chance to reconnect with colleagues, celebrate wins, and get a glimpse of the product roadmap:

“I’ve had to learn that many people want to use the event to have fun, reconnect with colleagues, and find 1 or 2 small motivating things (like product roadmap, or sales process tweaks). They believe their current skill set is fine.”

Todd himself states that finally understanding this was a hard pill to swallow, but that ignoring this is worse. 

How to avoid it:

Rather than fighting against this natural dynamic, work with it.

Todd suggests re-evaluating our own goals and expectations for SKO:

“I have learned to rethink my own goals for the agenda and what the ROI for the event is.”

Instead of assuming a uniform appetite for skill-building, create an agenda that blends learning with what reps naturally seek from the event:

• Tie training sessions directly to tangible improvements in quota attainment, deal velocity, or closing rates – things that matter to reps.

• Reps often trust their colleagues more than structured training. Panels, customer win stories, and top-performer sessions can make learning feel more authentic.

• Instead of overloading the agenda with training, build in purposeful moments for networking and informal discussions.

• Product roadmaps are engaging because they impact how reps sell. The same principle applies to any other content – position it in a way that clearly benefits them in their day-to-day work.

SKOs should be a launchpad for performance, but that starts by aligning with reps’ real motivations rather than imposing an overly rigid vision of what we think they should prioritise.

Mistake #24: Skipping the final run-through

Dry runs may not be the most exciting part of SKO preparation, but skipping them can result in disjointed messaging, awkward transitions, and missed opportunities to fine-tune delivery.

One of the most common pitfalls of inadequate rehearsal is inconsistency across different departments. For example:

• Product might focus on the technical roadmap and new feature enhancements, assuming reps already understand how to position them.

• Marketing might highlight the broader go-to-market strategy, leaning on branding and messaging rather than tactical selling.

• Sales leadership might drill down on aggressive pipeline targets and urgency, without ensuring that reps understand how to bridge the gap between product capabilities and customer pain points.

Without a cohesive narrative, these competing angles can create confusion rather than clarity. 

Additionally, last-minute surprises – like speakers overrunning their allotted time or clunky transitions between sessions – can make an otherwise well-planned event feel unpolished and unprofessional.

How to avoid it:

Louisa Morassutti adroitly points out that preparing for the final checks starts with planning:

“Make sure you have time in your project plan for a walk-through of the content in role dry runs so that you can make sure you are weaving the theme and messaging throughout (this gives you time to update the speakers on what the others are talking about so the handoffs are seamless”

Mistake #25: Waiting too long to start planning

One of the biggest pitfalls in SKO planning is underestimating the time it takes to pull off a well-executed event. 

In my recent article on sales kick-off planning best practices, the majority of contributors agreed that SKO planning should begin at least 6 to 9 months in advance.

Of course, not every detail can be locked in that early – agendas will evolve, speakers will shift, and last-minute adjustments are inevitable. But waiting until December to start planning for an SKO that’s happening on January 5th is a recipe for a rushed, disorganised event that fails to meet its full potential.

How to avoid it:

• Aim to define core objectives, align with leadership, and establish a rough budget at least 6-9 months before the event.

• Break planning into structured phases to avoid last-minute scrambling; begin with defining goals and aligning stakeholders, then move into agenda design, speaker selection, logistics, and reinforcement planning.

• Secure key resources early. If your SKO requires external speakers, venue bookings, or significant cross-functional coordination, early action prevents conflicts and limited availability.

• Schedule regular check-ins such as a monthly planning cadence to maintain momentum and keeps all teams aligned on progress, preventing bottlenecks in the final stretch.

Starting early doesn’t just mean giving yourself more time; it means having the space to make strategic decisions, refine the agenda, and ensure your SKO delivers real impact rather than feeling like a hastily assembled gathering.

Mistake #26: Assuming everything will go according to plan 

Even the most meticulously planned SKOs encounter unexpected hiccups – it’s not a matter of if, but when. 

The key isn’t aiming for perfection but ensuring you’re prepared to adapt when things go sideways.

Beverlie Helman sums it up perfectly:

“Don’t sweat the small stuff. Something will inevitably go wrong, but just make sure the critical components are nailed down.”

Alicia Avrach shared a real-world example:

“We had an SKO in Dallas in February with an outdoor scavenger hunt, and it was very cold, windy and rainy on the day. Luckily, we gave out umbrellas in the swag bag, and they were put to good use.”

How to avoid it:

• Pinpoint 3-5 agenda items (non-negotiables) that must go smoothly and focus your contingency planning around them.

• Have backup plans for logistical challenges such as AV failures, speaker no-shows, or last-minute venue changes.

• Unexpected delays happen, so leave buffer time so that minor disruptions don’t derail the entire agenda.

• Run “roleplays” for common failures (e.g., a speaker’s flight is delayed, the Wi-Fi crashes) so staff know how to pivot smoothly. 

As Alicia wisely noted:

“People loved the SKO despite the weather – but now I always have a backup.” 

Perfection isn’t the goal; resilience and adaptability are what truly make a successful SKO.

Conclusion

Alicia’s rain-soaked Dallas SKO reveals a core truth: the most memorable kick-offs embrace controlled chaos. 

As the 26 mistakes covered in this article demonstrate (together with the leaders’ approach to avoiding them), the solution lies in marrying preparation with flexibility.

These mistakes collectively teach us:

• Agendas breathe when they balance structure with spontaneity 

• Teams thrive through practiced cohesion, not perfect scripts

• The lasting impact comes from shared experiences, not perfectly executed checklists.

Chasing flawless execution can sterilise the very energy that makes SKOs powerful. 

A slightly imperfect event that reps still reference years later (“remember Dallas?”) is far more valuable than a forgettable, polished one that fades by Q2.

Your true measure of success?

When teams leave debating ideas, not complaining about slides.

Once again, a huge thanks to Alicia, Beverlie, Eric, Ivy, Kelley, Lauren, Leah, Liz, Louisa, Mat, Monti, Nina, Paul, Russell, Tim, and Todd for their invaluable contributions to this piece.